Jason Lemkin

570 statements across 97 episodes · 152 bullish · 239 bearish · 15 people on the record · first statement Jul 1, 2015 by Jason Lemkin · said 324 times in 146 episodes since 2016 · across every show →

On the record as a speaker too: Jason Lemkin's record, appearances and statements → this page counts the times other people say the name.

Mentions by year

brought up most by Harry Stebbings (243), Eran Zinman (15), Ivan Mazour (6), Sam Blond (5), Nicolas Dessaigne (5), Garry Tan (5), Ishan Mukherjee (4), Byron Deeter (4)

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2026 73 mentions in 24 episodes 3 per episode
2025 49 mentions in 22 episodes 2 per episode
2024 39 mentions in 18 episodes 2 per episode
2023 22 mentions in 14 episodes 2 per episode
2022 7 mentions in 5 episodes 1 per episode
2021 4 mentions in 3 episodes 1 per episode
2020 2 mentions in 1 episode
2019 7 mentions in 2 episodes 4 per episode
2018 7 mentions in 4 episodes 2 per episode
2017 32 mentions in 18 episodes 2 per episode
2016 82 mentions in 35 episodes 2 per episode

every mention, scene by scene, with the transcript →

Everything said about Jason Lemkin, oldest first

Jul 1, 2015 positive
Assertion Not checkable as stated
Lemkin prepared 100 SaaStr blog posts before leaving Adobe
“And then the day I left Adobe was the day of the first blog post on SaaS. I already had a hundred in the queue, so.”
Jason Lemkin Jul 1, 2015 ▶ 3:48 20 VC 050: Starting, Building and Selling in SaaS with the King of SaaS, Jason Lemkin, Managing Director @ Storm Ventures
Jul 1, 2015 bullish
Insight
Lemkin: One enterprise customer signals repeatable SaaS growth, not an outlier
“If you have one, I'll bet that you can get 10 and then a hundred. As a founder, this is a bet that I'll make that other VCs won't. I will bet that one is not an outlier, that one is the future. But if it's zero, I'm not sure I'll take the bet.”
Jason Lemkin Jul 1, 2015 ▶ 18:47 20 VC 050: Starting, Building and Selling in SaaS with the King of SaaS, Jason Lemkin, Managing Director @ Storm Ventures
Jul 1, 2015 positive
Disclosure
Lemkin invested in Algolia at $5K MRR before Accel's $18M round
“I did, I invested in a search as a service company called Algolia about a year ago that Excel just put eighteen million into, and I did it, and I did a session with the CEO at Heavybit a couple weeks ago, and I invested I think at like five KMR, so pretty earl…”
Jason Lemkin Jul 1, 2015 ▶ 18:23 20 VC 050: Starting, Building and Selling in SaaS with the King of SaaS, Jason Lemkin, Managing Director @ Storm Ventures
Jul 1, 2015 negative
Opinion
Lemkin: The 40% rule in SaaS exists to justify slow growth
“I think it's I think it's fine, but I think it's too clever. I think it's trying to justify slow growth, medium growth, high growth businesses and different burn rates.”
Jason Lemkin Jul 1, 2015 ▶ 12:16 20 VC 050: Starting, Building and Selling in SaaS with the King of SaaS, Jason Lemkin, Managing Director @ Storm Ventures
Jul 1, 2015
Assertion Not checkable as stated
Lemkin limits his schedule to one founder pitch meeting per week
“By the time I actually meet, I only do one founder meeting a week.”
Jason Lemkin Jul 1, 2015 ▶ 15:02 20 VC 050: Starting, Building and Selling in SaaS with the King of SaaS, Jason Lemkin, Managing Director @ Storm Ventures
Jul 1, 2015 positive
Disclosure
Lemkin's SaaS investment thesis focuses on hiring VPs and standardized playbooks
“My investment thesis on all my investments is I'll help you find great VPs for these roles, sales, marketing, customer success, and even products sometimes, and then we'll just run the playbook. We're just going to run the same playbook.”
Jason Lemkin Jul 1, 2015 ▶ 17:05 20 VC 050: Starting, Building and Selling in SaaS with the King of SaaS, Jason Lemkin, Managing Director @ Storm Ventures
Jul 1, 2015
Assertion Not checkable as stated
Lemkin: His only investment with an inferior CEO was his worst performer
“I've made eight institutional investments and 12 as a seed investor, 20. Only one of them was the CEO not as good as me, and it's my worst investment.”
Jason Lemkin Jul 1, 2015 ▶ 12:59 20 VC 050: Starting, Building and Selling in SaaS with the King of SaaS, Jason Lemkin, Managing Director @ Storm Ventures
Jul 22, 2015 negative
Opinion
Turner: B2B First Sales Do Not Guarantee Scalability
“I think in business-to-business software, that, that would be kind of a tough rule because we do see a lot of situations where a specific piece of software is developed for one customer with a pretty specific need, and that getting beyond that one customer to …”
Guy Turner Jul 22, 2015 ▶ 6:25 20 VC 056: The Life Cycle of Startups with Guy Turner, Partner @ Hyde Park Venture Partners
Jan 8, 2016 positive
Opinion
Mazour: Jason Lemkin's SaaStr is the definitive SaaS guidebook
“It's basically a guidebook for how to run a SaaS company. There's very little that I do that I didn't learn from his blog.”
Ivan Mazour Jan 8, 2016 ▶ 22:39 20 VC FF 029: VC vs Angel Funding & The Future of E-Commerce with Ivan Mazour, Founder @ Ometria
Apr 22, 2016 positive
Disclosure
Algolia Delayed Post-YC Series A to Take Small Investment From Jason Lemkin
“And so we finally decided not to raise any series A after weight combinator, but to take the risk to just raise a very small round to onboard new investors that we thought could provide a lot of value. That's when Jason Lemkin joined, joined us as an investor.”
Nicolas Dessaigne Apr 22, 2016 ▶ 13:34 20VC: Fundraising Is Also Business Development with Nicolas Dessaigne, Co-Founder & CEO @ Algolia
Aug 8, 2016
Disclosure
Data Collective passes on standard SaaS deals favored by Jason Lemkin
“We regretfully either say no up front or don't follow on in the kind of companies that somebody like Jason Lempton is going to make a fortune in.”
Matt Ocko Aug 8, 2016 ▶ 16:30 20VC: Data Collective's Matt Ocko on Why "All Fund Size Models Are Wrong" and The Lifecycle of Current Venture Funds Is Inefficient?
Oct 24, 2016 bullish
Prediction Not checkable as stated
The SaaStr Community Will Drive Significant Deal Flow for Jason Lemkin
“SASTR to me is a great example of that because the community he built, that's just really hard to replicate, and it will deliver a significant amount of deal flow to him”
Beezer Clarkson Oct 24, 2016 ▶ 26:21 20VC: More $ Raised This Year Than The Past 15, War Chests Being Built & Decline In First Time Funds: So What The Heck Is Happening In Venture with Beezer Clarkson, Managing Director @ Sapphire Ventures
Mar 20, 2017 neutral
Disclosure
Lemkin: SaaStr manages a $70M fund targeting 10-15% ownership
“So we have a seventy million dollar fund. We try to buy ownership stakes in the 10 to 15% range, sometimes a little higher.”
Jason Lemkin Mar 20, 2017 ▶ 5:10 20VC: SaaStr's Jason Lemkin on The 3 Things You Want From Your LPs, Why Most VCs Do Not Add Value & Why The Best VCs Know How To Package Startups For The Next Round
Mar 20, 2017 positive
Insight
Lemkin: VCs committing 1%+ of their fund will do whatever it takes to help
“Someone that puts in one, two, three percent of their fund into the investment is going to do whatever it takes to help the company and to help you raise the next round.”
Jason Lemkin Mar 20, 2017 ▶ 9:34 20VC: SaaStr's Jason Lemkin on The 3 Things You Want From Your LPs, Why Most VCs Do Not Add Value & Why The Best VCs Know How To Package Startups For The Next Round
Mar 20, 2017
Disclosure
Lemkin: SaaStr Has Never Invested in Pre-Revenue Companies
“As a VC, I've never done a pre-revenue investment, and I'm not sure that I will.”
Jason Lemkin Mar 20, 2017 ▶ 19:38 20VC: SaaStr's Jason Lemkin on The 3 Things You Want From Your LPs, Why Most VCs Do Not Add Value & Why The Best VCs Know How To Package Startups For The Next Round
Mar 20, 2017 positive
Disclosure
Jason Lemkin gets 100% of his deal flow from SaaStr
“I've learned that the blog and the Saster community is all of my deal flow. It's a hundred percent of it, but it's 10 times bigger than it was two and a half years ago.”
Jason Lemkin Mar 20, 2017 ▶ 27:37 20VC: SaaStr's Jason Lemkin on The 3 Things You Want From Your LPs, Why Most VCs Do Not Add Value & Why The Best VCs Know How To Package Startups For The Next Round
Mar 20, 2017
Assertion Partly supported
Adobe Document Services ARR Doubled From $50M to $100M in 2012–2013
“He oversaw the growth of Adobe Document Services ARR from fifty million dollars in 2012 to a staggering one hundred million dollars in 2013.”
Harry Stebbings Mar 20, 2017 ▶ 0:56 20VC: SaaStr's Jason Lemkin on The 3 Things You Want From Your LPs, Why Most VCs Do Not Add Value & Why The Best VCs Know How To Package Startups For The Next Round
Mar 20, 2017 neutral
Insight
Lemkin: Solo GPs are more conservative than partners at multi-partner VC firms
“The learning is when you're on your own in a solo GP fund, you're actually, you're more conservative. I say no to deals that I would have done in another firm, and I'm not remotely convinced that's the right decision.”
Jason Lemkin Mar 20, 2017 ▶ 6:13 20VC: SaaStr's Jason Lemkin on The 3 Things You Want From Your LPs, Why Most VCs Do Not Add Value & Why The Best VCs Know How To Package Startups For The Next Round
Mar 20, 2017 negative
Insight
Lemkin: Mega-funds leading $700k seed rounds is suboptimal for founders
“In an ideal world, a ten billion dollar fund leading your 700,000 dollar round is suboptimal because that's nickels and dimes. It's pocket change. No one putting in a tiny amount of money is going to remotely care if they write off the investment.”
Jason Lemkin Mar 20, 2017 ▶ 9:15 20VC: SaaStr's Jason Lemkin on The 3 Things You Want From Your LPs, Why Most VCs Do Not Add Value & Why The Best VCs Know How To Package Startups For The Next Round
Mar 20, 2017 positive
Disclosure
Lemkin: All but one portfolio company raised eight-figure follow-on checks
“All but one of my deals so far has been followed with an eight figure check from a top SAS VC.”
Jason Lemkin Mar 20, 2017 ▶ 17:04 20VC: SaaStr's Jason Lemkin on The 3 Things You Want From Your LPs, Why Most VCs Do Not Add Value & Why The Best VCs Know How To Package Startups For The Next Round
Mar 20, 2017 neutral
Insight
Lemkin: Every SaaStr investment must have $700M valuation potential
“So if you kind of back into that math with a little dilution, that means every single time that we invest, I have to believe the company will be worth at least seven hundred million dollars.”
Jason Lemkin Mar 20, 2017 ▶ 5:18 20VC: SaaStr's Jason Lemkin on The 3 Things You Want From Your LPs, Why Most VCs Do Not Add Value & Why The Best VCs Know How To Package Startups For The Next Round
Mar 20, 2017
Disclosure
Lemkin's first startup raised $9M on $2M pre-money with 5x liquidation preference
“In my first startup before Echo sign, there was so much drama the first time I raised money. But at the end of the day, I got the world's worst term sheet with the world's worst terms. It was nine, a nine million round on a two pre with a five X liquidation pr…”
Jason Lemkin Mar 20, 2017 ▶ 8:30 20VC: SaaStr's Jason Lemkin on The 3 Things You Want From Your LPs, Why Most VCs Do Not Add Value & Why The Best VCs Know How To Package Startups For The Next Round
Apr 3, 2017
Insight
Hunter Walk: Early-stage investors must back misunderstood companies
“So I'd say Lemkin is totally correct when you're playing in a space where the goalposts are well documented. But I think as an early stage investor, you also need to be willing to back companies that are going to be misunderstood for a long period of time and …”
Hunter Walk Apr 3, 2017 ▶ 11:52 20VC: Homebrew's Hunter Walk on Why There Is No Series A Crunch, How To Package Portfolio Companies For The Next Round & Why The Bridge Round Is Not Always A Negative Sign?
May 1, 2017 neutral
Insight
Stebbings: Creators should choose immortal content platforms over ephemeral ones like Snapchat
“And then just with the content, fundamental to choose immortal content platforms, so Snapchat for content isn't really great unless you're looking to create connections. It dies and is not searchable. The likes of Jason Lemkin have done incredibly well with Qu…”
Harry Stebbings May 1, 2017 ▶ 21:56 20VC: Explosion of First Time Funds, Only 1 Mega Fund Raised: What The Heck Happened in Q1 Venture Markets with Beezer Clarkson, Managing Director @ Sapphire Ventures
May 15, 2017
Insight
Rabois: Replace executives whose personal growth lags company velocity
“When the individual's propensity to grow falls below the company's growth rate, I think you need to make a change.”
Keith Rabois May 15, 2017 ▶ 11:12 20VC: Khosla's Keith Rabois on How To Create Sustainability Behind Growth, How To Assess The Potential Of Individuals & Teams & The Biggest Takeaways from LinkedIn, Paypal & Square
Apr 30, 2018 negative
Opinion
Neumann rejects Jason Lemkin's view that VC is just packaging startups
“I don't look at it that way. If you say it that way, it makes it sound like you're trying to gild the lily, right? You're trying to sell them something that's not actually true. I do think that you need to know what the company needs to look like to raise more…”
Jerry Neumann Apr 30, 2018 ▶ 19:34 20VC: Why Follow-On Investments Are Always A Better Investment, Why Spray and Pray Investing Is Like The Stock Market & Why Startups Need A Board From Day One with Jerry Neumann
Apr 20, 2020 bearish
Insight
M&A prices drop in downturns as acquirers prioritize cost-cutting
“Yeah, no question. Because if there's a limited set of buyers and a whole bunch of companies that want to be acquired and remember my mindset at the start of the podcast was people right now are not paid to innovate. They're not paid to innovate. They're paid …”
Mark Suster Apr 20, 2020 ▶ 20:25 20VC: Upfront's Mark Suster on COVID Redefining What A Great Company Looks Like and What Valuations Look Like, Why Pay-To-Play Is Back On The Table & Why We Will See The Death of Party Rounds
May 6, 2022 positive
Disclosure
Lemkin: All core portfolio positions maintain double-digit ownership
“When I look over my eight year history of investing, it's the ones with the double digit ownership that moved the needle. And for better or worse, when I've had my own fund, when I look at what the companies I'm sitting on today, obviously you regret ones you …”
Jason Lemkin May 6, 2022 ▶ 6:15 20VC: Why the Traditional Seed Fund Model No Longer Works, Why Multi-Stage Funds Investing at Seed Bring Signaling Risk but also Less Pressure, The One Criteria All Potential Sales Hires Need to Have and The Clear Signs of 10x Sales Hires with Jason Lemki
May 6, 2022 neutral
Assertion Not checkable as stated
Lemkin: Most founder-led funds succeed via a single decacorn hit
“Most of these funds like this, they have one great Decacorn in their portfolio and it just works.”
Jason Lemkin May 6, 2022 ▶ 49:28 20VC: Why the Traditional Seed Fund Model No Longer Works, Why Multi-Stage Funds Investing at Seed Bring Signaling Risk but also Less Pressure, The One Criteria All Potential Sales Hires Need to Have and The Clear Signs of 10x Sales Hires with Jason Lemki
May 6, 2022 negative
Insight
Lemkin: Pass on Founders Lacking 20-Year Commitment
“My rule is, and I've made this mistake since, don't invest. No matter how much you love, you can love them as humans. They can be doing very well. But if you don't have this crazy 20 year commitment to building something huge, it's hard to make money in ventur…”
Jason Lemkin May 6, 2022 ▶ 5:40 20VC: Why the Traditional Seed Fund Model No Longer Works, Why Multi-Stage Funds Investing at Seed Bring Signaling Risk but also Less Pressure, The One Criteria All Potential Sales Hires Need to Have and The Clear Signs of 10x Sales Hires with Jason Lemki
May 6, 2022 bearish
Opinion
Lemkin: The traditional $50M–$60M seed fund model no longer works
“Does the traditional 50, sixty million dollar seed fund work. I think it doesn't work unless you go with anything that has any proof, any social proof, anything privileged, it doesn't work. So you either have to find the less privileged where I think it works,…”
Jason Lemkin May 6, 2022 ▶ 29:09 20VC: Why the Traditional Seed Fund Model No Longer Works, Why Multi-Stage Funds Investing at Seed Bring Signaling Risk but also Less Pressure, The One Criteria All Potential Sales Hires Need to Have and The Clear Signs of 10x Sales Hires with Jason Lemki
May 6, 2022
Insight
Lemkin: Board Meetings Serve as Essential Management Forcing Functions
“I think you can really only be so upset with them once or twice a year. Otherwise it's demoralizing and people quit. But if every six weeks your VP of sales, that's a little bit behind has to report, Harry, my plan for Q one was ten million. I'm at 8.4. Here's…”
Jason Lemkin May 6, 2022 ▶ 38:51 20VC: Why the Traditional Seed Fund Model No Longer Works, Why Multi-Stage Funds Investing at Seed Bring Signaling Risk but also Less Pressure, The One Criteria All Potential Sales Hires Need to Have and The Clear Signs of 10x Sales Hires with Jason Lemki
May 6, 2022
Disclosure
Lemkin: Most of my top investments lacked blue-chip tech pedigree
“I would say most of my best investments did not, and those have not seen the same level of pre-seed inflation, but they have seen enough that can break the seed model.”
Jason Lemkin May 6, 2022 ▶ 28:02 20VC: Why the Traditional Seed Fund Model No Longer Works, Why Multi-Stage Funds Investing at Seed Bring Signaling Risk but also Less Pressure, The One Criteria All Potential Sales Hires Need to Have and The Clear Signs of 10x Sales Hires with Jason Lemki
May 6, 2022 bullish
Insight
Lemkin: Investing in A+ CEO-CTO pairings with traction never loses money
“When I see both as an A plus and any traction at all, like any traction at all, I feel like I literally cannot lose money on that combination.”
Jason Lemkin May 6, 2022 ▶ 50:26 20VC: Why the Traditional Seed Fund Model No Longer Works, Why Multi-Stage Funds Investing at Seed Bring Signaling Risk but also Less Pressure, The One Criteria All Potential Sales Hires Need to Have and The Clear Signs of 10x Sales Hires with Jason Lemki
May 6, 2022 neutral
Prediction Open · timeframe May 2027
Lemkin: 50 active startup founders will raise nine-figure venture funds
“There's too many founders that are going to raise nine-figure funds, While they're running their own startups, and it used to be a bad sign for the startup. How could you do anything other than run your own startup? But it doesn't matter what you and I think, …”
Jason Lemkin May 6, 2022 ▶ 48:07 20VC: Why the Traditional Seed Fund Model No Longer Works, Why Multi-Stage Funds Investing at Seed Bring Signaling Risk but also Less Pressure, The One Criteria All Potential Sales Hires Need to Have and The Clear Signs of 10x Sales Hires with Jason Lemki
May 6, 2022
Insight
Lemkin: Long enterprise sales cycles become predictable at $20M–$30M ARR
“North of 20, thirty million in revenue, you're lining up so many deals at the same time that long sales cycles don't matter because if you have a hundred deals in flight, it actually starts to happen very predictably, right?”
Jason Lemkin May 6, 2022 ▶ 17:58 20VC: Why the Traditional Seed Fund Model No Longer Works, Why Multi-Stage Funds Investing at Seed Bring Signaling Risk but also Less Pressure, The One Criteria All Potential Sales Hires Need to Have and The Clear Signs of 10x Sales Hires with Jason Lemki
May 6, 2022
Insight
Lemkin: Enterprise SaaS founders remain head of sales until $10M ARR
“In true enterprise, like real enterprise, the founder is often the VP of sales until ten million.”
Jason Lemkin May 6, 2022 ▶ 18:27 20VC: Why the Traditional Seed Fund Model No Longer Works, Why Multi-Stage Funds Investing at Seed Bring Signaling Risk but also Less Pressure, The One Criteria All Potential Sales Hires Need to Have and The Clear Signs of 10x Sales Hires with Jason Lemki
May 6, 2022
Insight
Lemkin: At scale, SaaS quotas should be 3x to 5x OTE
“And then at scale, we end up at these three X, four X, five X numbers, right? Which is quotas are an SMB. Usually three X, you're fully burdened comp. You're on target earnings, you're OT up to five X in the enterprise. That's the way it works.”
Jason Lemkin May 6, 2022 ▶ 16:38 20VC: Why the Traditional Seed Fund Model No Longer Works, Why Multi-Stage Funds Investing at Seed Bring Signaling Risk but also Less Pressure, The One Criteria All Potential Sales Hires Need to Have and The Clear Signs of 10x Sales Hires with Jason Lemki
May 6, 2022
Assertion Not checkable as stated
Lemkin: Most successful B2B founders serve as first head of sales
“I would say the majority of B to B companies That are successful that you and I have worked with, Harry, the majority, but not all. The founder has been the first head of sales.”
Jason Lemkin May 6, 2022 ▶ 10:41 20VC: Why the Traditional Seed Fund Model No Longer Works, Why Multi-Stage Funds Investing at Seed Bring Signaling Risk but also Less Pressure, The One Criteria All Potential Sales Hires Need to Have and The Clear Signs of 10x Sales Hires with Jason Lemki
May 6, 2022 positive
Disclosure
Lemkin: Five of First Six Venture Investments Became Unicorns
“The first four investments eventually became unicorns, five out of the first six”
Jason Lemkin May 6, 2022 ▶ 4:06 20VC: Why the Traditional Seed Fund Model No Longer Works, Why Multi-Stage Funds Investing at Seed Bring Signaling Risk but also Less Pressure, The One Criteria All Potential Sales Hires Need to Have and The Clear Signs of 10x Sales Hires with Jason Lemki
May 6, 2022 negative
Insight
Lemkin: Founders Should Require Board Slides Instead of Notion Docs
“That's why I beg founders not to use notion and board meetings. I begged them to force everyone to make slides to spend the time because we all love notion and Coda. We just put our stuff in our Google docs. It's so efficient, isn't it? But not only did I thin…”
Jason Lemkin May 6, 2022 ▶ 39:20 20VC: Why the Traditional Seed Fund Model No Longer Works, Why Multi-Stage Funds Investing at Seed Bring Signaling Risk but also Less Pressure, The One Criteria All Potential Sales Hires Need to Have and The Clear Signs of 10x Sales Hires with Jason Lemki
May 6, 2022 positive
Insight
Lemkin: When investors identify a winner, buy maximum available allocation
“When you meet a winner, you buy all the shares. Now, if you can buy a quarter of the company, you buy a quarter of the company. If you can buy two percent of the company, you buy two percent of the company. But you either buy all of them or none.”
Jason Lemkin May 6, 2022 ▶ 6:48 20VC: Why the Traditional Seed Fund Model No Longer Works, Why Multi-Stage Funds Investing at Seed Bring Signaling Risk but also Less Pressure, The One Criteria All Potential Sales Hires Need to Have and The Clear Signs of 10x Sales Hires with Jason Lemki
May 25, 2022 negative
Insight
Early sales teams need collaboration over manufactured internal competition
“I think if you really need to rely on sort of like having people with the same cohort to drive competition, I think you may have hired the wrong people in my opinion, right? Because in that early stage, I'm actually trying to foster more than anything, a cultu…”
Oliver Jay May 25, 2022 ▶ 15:16 Oliver Jay: How To Create and Execute a World-Class Sales Playbook | 20VC #889 · 20VC with Harry Stebbings
Nov 30, 2022 positive
Insight
Lemkin: Operator-VCs Should Only Invest in CEOs Better Than Themselves
“You have to invest in CEOs that were better than you. If you know the problem, if I know, if I'm a podcaster and I know Riverside or whatever the other versions are, and I look, Riverside's great. We're on it today. And you meet the CEO who I don't know, and h…”
Jason Lemkin Nov 30, 2022 ▶ 19:58 Jason Lemkin: Cold Email Tips; Why Only 15% of Founders Listen to their VCs | 20VC #954 · 20VC with Harry Stebbings
Nov 30, 2022 positive
Insight
Lemkin: Early traction against free open source is the ultimate signal
“There's probably no better signal than when you compete with a free open source platform and your product is exploding, even at an early day, because it's gotta be magical.”
Jason Lemkin Nov 30, 2022 ▶ 22:06 Jason Lemkin: Cold Email Tips; Why Only 15% of Founders Listen to their VCs | 20VC #954 · 20VC with Harry Stebbings
Nov 30, 2022 bullish
Disclosure
Lemkin: Invested in Salesloft pre-revenue before $2.5B acquisition
“I was involved, invested in sales loft pre-revenue, right? We sold for two and a half billion last year.”
Jason Lemkin Nov 30, 2022 ▶ 27:23 Jason Lemkin: Cold Email Tips; Why Only 15% of Founders Listen to their VCs | 20VC #954 · 20VC with Harry Stebbings
Nov 30, 2022 positive
Insight
Lemkin: New Operator-VCs Should Ignore Advice to Slow Down and Invest Aggressively
“Don't listen to the advice to slow it down, right? If you join a larger fund, their incentives are different than yours, right? You're new, the ball is set. They're just hoping, a large fund is hoping in the next two years you find one notion, that's all they …”
Jason Lemkin Nov 30, 2022 ▶ 18:59 Jason Lemkin: Cold Email Tips; Why Only 15% of Founders Listen to their VCs | 20VC #954 · 20VC with Harry Stebbings
Nov 30, 2022 negative
Insight
Lemkin: Only 15% of venture-backed founders can handle critical VC feedback
“Even of this Ivy League of venture-backed founders, I would say only maybe 15% really can take the feedback. And 25% will tolerate it, and then 60% will hate you for it. They hate you for it.”
Jason Lemkin Nov 30, 2022 ▶ 43:40 Jason Lemkin: Cold Email Tips; Why Only 15% of Founders Listen to their VCs | 20VC #954 · 20VC with Harry Stebbings
Nov 30, 2022
Assertion Contradicted
Lemkin: SaaStr Still Generates 500,000 Monthly Views on Quora
“And I'm still there by myself getting a half a million views a month”
Jason Lemkin Nov 30, 2022 ▶ 1:05:55 Jason Lemkin: Cold Email Tips; Why Only 15% of Founders Listen to their VCs | 20VC #954 · 20VC with Harry Stebbings
Nov 30, 2022
What-if
Lemkin: Would pass on early Algolia deal today over ownership
“First of all, I would have done the million at 15 in a heartbeat, right? And that would have been my bare minimum of investment, right? Because then I would have owned eight percent or something in the company. And no, I would have passed on it.”
Jason Lemkin Nov 30, 2022 ▶ 9:35 Jason Lemkin: Cold Email Tips; Why Only 15% of Founders Listen to their VCs | 20VC #954 · 20VC with Harry Stebbings
Nov 30, 2022 negative
What-if
Lemkin: Would have built legendary funds with a co-founding partner
“I would have been a much better investor with a partner than as a solo GP. I'll say it with a hundred percent certainty, a hundred percent. Sorry. I would have been better. I'm going to do fine. Don't get me wrong. No, no, I will do well, but I could have had …”
Jason Lemkin Nov 30, 2022 ▶ 50:01 Jason Lemkin: Cold Email Tips; Why Only 15% of Founders Listen to their VCs | 20VC #954 · 20VC with Harry Stebbings
Nov 30, 2022
Disclosure
Lemkin: Went five to six years in venture without losing money
“I didn't even lose any money for five or six years.”
Jason Lemkin Nov 30, 2022 ▶ 8:12 Jason Lemkin: Cold Email Tips; Why Only 15% of Founders Listen to their VCs | 20VC #954 · 20VC with Harry Stebbings
Nov 30, 2022 positive
Assertion Supported
Lemkin: Talkdesk was his third investment and reached a $10B valuation
“My third investment was talk desk, which is worth ten billion today.”
Jason Lemkin Nov 30, 2022 ▶ 47:40 Jason Lemkin: Cold Email Tips; Why Only 15% of Founders Listen to their VCs | 20VC #954 · 20VC with Harry Stebbings
Nov 30, 2022 neutral
Prediction Not checkable as stated
Lemkin: Commits to never cutting due diligence corners again
“I will never cut a corner. I will never cut a corner again. And even though there are minor corners, I won't, I just won't do it. And it will impact investment velocity.”
Jason Lemkin Nov 30, 2022 ▶ 59:39 Jason Lemkin: Cold Email Tips; Why Only 15% of Founders Listen to their VCs | 20VC #954 · 20VC with Harry Stebbings
Nov 30, 2022
Insight
Lemkin: Small VC funds need one real unicorn annually with high ownership
“If your fund size isn't huge to win in venture, like you need a real unicorn a year with large ownership and the math is magical.”
Jason Lemkin Nov 30, 2022 ▶ 12:27 Jason Lemkin: Cold Email Tips; Why Only 15% of Founders Listen to their VCs | 20VC #954 · 20VC with Harry Stebbings
Nov 30, 2022 bullish
Disclosure
Lemkin: Decided to invest in all initial unicorns before meeting them
“I already wanted to invest before I met all of my initial unicorns.”
Jason Lemkin Nov 30, 2022 ▶ 3:48 Jason Lemkin: Cold Email Tips; Why Only 15% of Founders Listen to their VCs | 20VC #954 · 20VC with Harry Stebbings
Nov 30, 2022
Assertion Contradicted
Lemkin: Majority of his portfolio companies have female CEOs
“The majority of the companies I've invested in have a woman CEO”
Jason Lemkin Nov 30, 2022 ▶ 10:08 Jason Lemkin: Cold Email Tips; Why Only 15% of Founders Listen to their VCs | 20VC #954 · 20VC with Harry Stebbings
Nov 30, 2022
Assertion Supported
Lemkin: 100% of SaaStr's unicorn portfolio companies experienced a plateau year
“Every single The company I've invested in every unit, true unicorn, a hundred million more revenue or billion more cash exit. All of them have had a plateau year all a hundred percent”
Jason Lemkin Nov 30, 2022 ▶ 38:30 Jason Lemkin: Cold Email Tips; Why Only 15% of Founders Listen to their VCs | 20VC #954 · 20VC with Harry Stebbings
Nov 30, 2022
Disclosure
Lemkin: Half of Early SaaStr Deal Flow Came From Quora
“Half of my, probably my deal flow came from Quora in the early days.”
Jason Lemkin Nov 30, 2022 ▶ 1:05:30 Jason Lemkin: Cold Email Tips; Why Only 15% of Founders Listen to their VCs | 20VC #954 · 20VC with Harry Stebbings
Nov 30, 2022 negative
Insight
Lemkin: Pitch deck two-by-two competitive matrix slides waste time
“Most of those two by two matrices are throwaway slides. Don't have a throwaway slide. Don't have, it's a, it not only is it a waste of everyone's time, but it makes you look less than great if you have a throwaway slide.”
Jason Lemkin Nov 30, 2022 ▶ 22:59 Jason Lemkin: Cold Email Tips; Why Only 15% of Founders Listen to their VCs | 20VC #954 · 20VC with Harry Stebbings
Nov 30, 2022 bullish
Disclosure
Lemkin: Algolia Investment Was Made Despite Unanimous Rejection From Partners
“Algolia, and again, this was the first venture investment I did when it was unanimously no, and I still did it, but the founders were clearly better than me. The traction was better than I had. The understanding of the problem was better than I had as a founde…”
Jason Lemkin Nov 30, 2022 ▶ 20:25 Jason Lemkin: Cold Email Tips; Why Only 15% of Founders Listen to their VCs | 20VC #954 · 20VC with Harry Stebbings
Nov 30, 2022 positive
Insight
Lemkin: A founder's capability can be evaluated solely from their cold email
“The best founders are great communicators one way or the other. Right. And so if you can write an incredible cold email, like an incredible inbound email you can judge a human being and a company just from that email.”
Jason Lemkin Nov 30, 2022 ▶ 2:35 Jason Lemkin: Cold Email Tips; Why Only 15% of Founders Listen to their VCs | 20VC #954 · 20VC with Harry Stebbings
Nov 30, 2022 neutral
Disclosure
Lemkin: Every successful venture investment came from inbound emails
“I only invest from inbound Saster super fans. Every deal I've tried to go out and get, I've failed. I do nothing outbound. Every warm referral doesn't work out. Nothing works out except the high velocity inbound email.”
Jason Lemkin Nov 30, 2022 ▶ 0:58 Jason Lemkin: Cold Email Tips; Why Only 15% of Founders Listen to their VCs | 20VC #954 · 20VC with Harry Stebbings
Nov 30, 2022
Disclosure
Lemkin: Invested $500K in Algolia's Seed at $12M Pre and $3.5M in Series A
“I did only 500 K in the first round and I bought up in the next. I did three and a half million in the A. So I did 500 K in the seed at 12 pre.”
Jason Lemkin Nov 30, 2022 ▶ 6:57 Jason Lemkin: Cold Email Tips; Why Only 15% of Founders Listen to their VCs | 20VC #954 · 20VC with Harry Stebbings
Nov 30, 2022 bearish
Prediction Open · timeframe Nov 2027
Lemkin: Overfunded pre-PMF SaaS startups will all fail
“I don't see any way any of them succeed.”
Jason Lemkin Nov 30, 2022 ▶ 32:47 Jason Lemkin: Cold Email Tips; Why Only 15% of Founders Listen to their VCs | 20VC #954 · 20VC with Harry Stebbings
Jan 13, 2023
Disclosure
Lemkin invested in Pipedrive, Talkdesk, Algolia, Greenhouse, and Salesloft in 12 months
“I did pipe drive, talk desk, Algolia, greenhouse, and sales loft all within 12 months.”
Jason Lemkin Jan 13, 2023 ▶ 1:04 Jason Lemkin: WTF is Going On in VC? Are LPs Investing in New Funds? | 20VC #965 · 20VC with Harry Stebbings
Jan 13, 2023 bullish
Prediction Not checkable as stated
Lemkin: Startups over-cutting today will face severe pipeline shortages by year-end
“We're cutting too much and it's going to hurt everybody, not this week or even this quarter, but it's going to hurt. Everyone's going to not going to have enough pipeline at the end of the year when I think things will be better. I think things will be better …”
Jason Lemkin Jan 13, 2023 ▶ 12:46 Jason Lemkin: WTF is Going On in VC? Are LPs Investing in New Funds? | 20VC #965 · 20VC with Harry Stebbings
Jan 13, 2023 negative
Disclosure
Lemkin admits to wasting investment shots during the recent venture boom
“I think we all wasted a few shots the last couple years. I know I wasted one or two. I wish I could get them back. I didn't waste 20, but times were so good I wasted shots.”
Jason Lemkin Jan 13, 2023 ▶ 42:50 Jason Lemkin: WTF is Going On in VC? Are LPs Investing in New Funds? | 20VC #965 · 20VC with Harry Stebbings
Jan 13, 2023 bearish
Insight
Lemkin: Startups that raise massive early capital become un-acquirable and "dead"
“When you raise massive amounts of money early, how are you going to sell for 10 X what you raise? Who's going to buy you for five hundred million dollars? You're dead.”
Jason Lemkin Jan 13, 2023 ▶ 29:13 Jason Lemkin: WTF is Going On in VC? Are LPs Investing in New Funds? | 20VC #965 · 20VC with Harry Stebbings
Jan 13, 2023 negative
Opinion
Lemkin: VCs boasting about high deal volume on Twitter are dishonest
“I do think it's harder to find good deals, and I think it is true, and I think people are a little bit full of it on the Twitter, right, and on the social media”
Jason Lemkin Jan 13, 2023 ▶ 1:18 Jason Lemkin: WTF is Going On in VC? Are LPs Investing in New Funds? | 20VC #965 · 20VC with Harry Stebbings
Jan 13, 2023 bullish
Prediction Didn’t hold up
Lemkin: SaaS multiples will rise 20% to 40% by end of 2023
“And so I'm pretty bullish at the end of this year. I'm bullish that multiples will be Up somewhere between 20 and 40%, and I believe that will lead to a rush to deploy capital, but for founders, you have to understand that will never lead to a return of 2021.”
Jason Lemkin Jan 13, 2023 ▶ 52:59 Jason Lemkin: WTF is Going On in VC? Are LPs Investing in New Funds? | 20VC #965 · 20VC with Harry Stebbings
Jan 13, 2023 negative
Insight
Lemkin: Early-stage VCs waste time adjusting markups on growing startups
“If you're not growing, I think it makes sense to mark it down. If it's growing at a decent rate, I think if you're not Fidelity or a late stage investor, I think it's a waste of your time to mark up or mark down because I asked all my LPs this question. They s…”
Jason Lemkin Jan 13, 2023 ▶ 28:17 Jason Lemkin: WTF is Going On in VC? Are LPs Investing in New Funds? | 20VC #965 · 20VC with Harry Stebbings
Jan 13, 2023 bearish
Prediction Not checkable as stated
Lemkin: The Series B fundraising bar will remain very high long-term
“The bar is going to remain high to be fundable for a very long period of time, especially Series B and B and later, it's going to remain very high.”
Jason Lemkin Jan 13, 2023 ▶ 54:58 Jason Lemkin: WTF is Going On in VC? Are LPs Investing in New Funds? | 20VC #965 · 20VC with Harry Stebbings
Jan 13, 2023 bearish
Disclosure
Lemkin made almost no venture investments in 2022 due to macro shifts
“I did almost no investing the last 12 months, and some of it's certainly the macro”
Jason Lemkin Jan 13, 2023 ▶ 1:09 Jason Lemkin: WTF is Going On in VC? Are LPs Investing in New Funds? | 20VC #965 · 20VC with Harry Stebbings
Jan 13, 2023 bearish
Prediction Open · timeframe Jan 2028
Lemkin: Boom-era micro-funds are already decimated and don't know it yet
“I think they're going to be decimated. I think they already are decimated and they don't know it.”
Jason Lemkin Jan 13, 2023 ▶ 41:45 Jason Lemkin: WTF is Going On in VC? Are LPs Investing in New Funds? | 20VC #965 · 20VC with Harry Stebbings
Jan 13, 2023 bearish
Prediction Didn’t hold up
Lemkin: Venture funding and valuations will never return to 2021 peaks
“For founders, you have to understand that will never lead to a return of 2021. Never.”
Jason Lemkin Jan 13, 2023 ▶ 53:11 Jason Lemkin: WTF is Going On in VC? Are LPs Investing in New Funds? | 20VC #965 · 20VC with Harry Stebbings
Jan 13, 2023 negative
Opinion
Lemkin: No sympathy for founders who cry about market conditions
“When I see like a founder cry, I have no sympathy.”
Jason Lemkin Jan 13, 2023 ▶ 56:11 Jason Lemkin: WTF is Going On in VC? Are LPs Investing in New Funds? | 20VC #965 · 20VC with Harry Stebbings
Jan 13, 2023 negative
Opinion
Lemkin: 90% of VCs haven't built products and cannot talk to CTOs
“90% of VCs make is they haven't built product themselves. They don't even know how to talk to a CTO or a technical co-founder.”
Jason Lemkin Jan 13, 2023 ▶ 33:56 Jason Lemkin: WTF is Going On in VC? Are LPs Investing in New Funds? | 20VC #965 · 20VC with Harry Stebbings
Jan 13, 2023 negative
Prediction Not checkable as stated
Lemkin: Startups unfundable today won't become fundable in a year-end recovery
“If you can'range any money at all today, like if you're unfundable, I don't think you're going to be fundable at the end of the year. Okay. If you're fundable today, but you don't like the metrics, you don't like the valuation, you double the end of this year …”
Jason Lemkin Jan 13, 2023 ▶ 54:25 Jason Lemkin: WTF is Going On in VC? Are LPs Investing in New Funds? | 20VC #965 · 20VC with Harry Stebbings
Jan 13, 2023 negative
Opinion
Lemkin: VCs tweeting about buying public Shopify shares are "losers"
“And so when I see VCs on Twitter talking about how they're looking at buying some shares of Shopify, honestly, I think they're losers.”
Jason Lemkin Jan 13, 2023 ▶ 26:21 Jason Lemkin: WTF is Going On in VC? Are LPs Investing in New Funds? | 20VC #965 · 20VC with Harry Stebbings
Jan 13, 2023 negative
Disclosure
Lemkin spent 24 months relearning that sociopath CEOs can build unicorns
“I've spent the last 24 months relearning the unicorn lessons. Re-learning that companies I thought would never be unicorns became unicorns. That sociopath CEOs became unicorns. That bullshit artists became unicorns. That folks that did not have an extremely st…”
Jason Lemkin Jan 13, 2023 ▶ 55:09 Jason Lemkin: WTF is Going On in VC? Are LPs Investing in New Funds? | 20VC #965 · 20VC with Harry Stebbings
Jan 13, 2023 negative
Opinion
Lemkin: Tech workforce quality plummeted as companies hired "mainstream normal people"
“The quality plummeted as we hired mainstream normal people, the quality plummeted. Any leader will tell you this quietly. Any VP, Mark Benioff said it last week. Like they'll tell you the quality went down the last three years. Way down.”
Jason Lemkin Jan 13, 2023 ▶ 32:42 Jason Lemkin: WTF is Going On in VC? Are LPs Investing in New Funds? | 20VC #965 · 20VC with Harry Stebbings
Jan 13, 2023 bullish
Assertion Partly supported
Lemkin: Talkdesk scaled from $1M to $15M ARR in a single year
“Going from, you know, one to fifteen million with so few employees in a year was so much product market fit in there that you're like, okay, well, this is going to be worth a billion, but not more, right?”
Jason Lemkin Jan 13, 2023 ▶ 43:57 Jason Lemkin: WTF is Going On in VC? Are LPs Investing in New Funds? | 20VC #965 · 20VC with Harry Stebbings
Jan 13, 2023 negative
Prediction Not checkable as stated
Lemkin: Laid-off tech workers won't build Figma, they want easy jobs
“I don't think any of those people are going to go off and start the next Figma. I think they're going to continue to look for a job. They can kind of phone it in and make a lot of money.”
Jason Lemkin Jan 13, 2023 ▶ 31:50 Jason Lemkin: WTF is Going On in VC? Are LPs Investing in New Funds? | 20VC #965 · 20VC with Harry Stebbings
Mar 22, 2023 negative
Opinion
Fillmann: Founders Should Hire Sales Reps Individually, Not in Competing Pairs
“If you want the environment where people perform at their best, you need safety. If you want safety, they have to know that you're trusting them, that you've got their back. And if you have two different people kind of competing in the same environment, I don'…”
Frank Fillmann Mar 22, 2023 ▶ 10:27 Frank Fillmann: How I Boosted Revenue by $500M at Salesforce; Tips for Hiring Salespeople | E992 · 20VC with Harry Stebbings
Aug 9, 2023
Disclosure
Lemkin: Valuation does not matter if target ownership percentage is secured
“Within a range, I simply don't care about valuation. I want to have a fair valuation where I can hit the ownership target, and I don't care.”
Jason Lemkin Aug 9, 2023 ▶ 9:04 Jason Lemkin: Every VC has a FRAUD in their portfolio; The IPO market is about to EXPLODE | E1046 · 20VC with Harry Stebbings
Aug 9, 2023 bullish
Assertion Partly supported
Lemkin: Talkdesk reached $10B valuation despite $150M public comps at investment
“When I invested in talk desk, the best comp was five, nine, which is public today. They were worth a stunning hundred and fifty million dollars as a public company. So the comp was horrific, right? It was terrible. You know, we can look at, I think five nines …”
Jason Lemkin Aug 9, 2023 ▶ 7:06 Jason Lemkin: Every VC has a FRAUD in their portfolio; The IPO market is about to EXPLODE | E1046 · 20VC with Harry Stebbings
Aug 9, 2023 bullish
Opinion
Lemkin: Series A is the best stage to invest in cloud software
“Series A is the best place to invest today in cloud and SaaS, right?”
Jason Lemkin Aug 9, 2023 ▶ 47:38 Jason Lemkin: Every VC has a FRAUD in their portfolio; The IPO market is about to EXPLODE | E1046 · 20VC with Harry Stebbings
Aug 9, 2023 negative
What-if
Lemkin: Not building a large team at SaaStr was my biggest mistake
“I think my biggest mistake, and you're not making it, Harry I think the biggest mistake I've made, and this is just me, because, again, everyone's different. This is the complicated thing about ventures. Everyone has different strengths and sweetnesses. I thin…”
Jason Lemkin Aug 9, 2023 ▶ 45:06 Jason Lemkin: Every VC has a FRAUD in their portfolio; The IPO market is about to EXPLODE | E1046 · 20VC with Harry Stebbings
Aug 9, 2023 bearish
Prediction Not checkable as stated
Lemkin: Current generation of tech knowledge workers will never work hard again
“I've changed my mind on the distributed world and distributed knowledge workers and everything, and I've just gotten a little jaded, and I just don't think most of the current generation of folks will ever work hard again.”
Jason Lemkin Aug 9, 2023 ▶ 1:11:08 Jason Lemkin: Every VC has a FRAUD in their portfolio; The IPO market is about to EXPLODE | E1046 · 20VC with Harry Stebbings
Aug 9, 2023
Insight
Lemkin: Investors never lose money backing great founders at $1M ARR
“If you get, if you're able to invest in a million and the founders are great, you'll never lose money. If the founders are graded a million in revenue”
Jason Lemkin Aug 9, 2023 ▶ 8:18 Jason Lemkin: Every VC has a FRAUD in their portfolio; The IPO market is about to EXPLODE | E1046 · 20VC with Harry Stebbings
Aug 9, 2023 positive
Assertion Not checkable as stated
Lemkin: I have achieved a 10x lifetime return on venture investments
“And listen, he's a better investor than I, but I'm 10 X lifetime. So I'm not bad.”
Jason Lemkin Aug 9, 2023 ▶ 40:41 Jason Lemkin: Every VC has a FRAUD in their portfolio; The IPO market is about to EXPLODE | E1046 · 20VC with Harry Stebbings
Aug 9, 2023 bullish
Assertion Supported
Lemkin: Enterprise IT spend has hit bottom and is recovering
“We are bouncing off the bottom. We are bouncing off these lows that we went through this period the last 18 months where not, not Failing unicorns. Big successful companies retrench their IT and spend budgets, right?”
Jason Lemkin Aug 9, 2023 ▶ 27:12 Jason Lemkin: Every VC has a FRAUD in their portfolio; The IPO market is about to EXPLODE | E1046 · 20VC with Harry Stebbings
Aug 9, 2023 negative
Opinion
Lemkin: Startups should not hire tech workers who lack pre-boom experience
“I almost think We shouldn't hire any of these people in startups today. You have to have had some adversity or have worked before the boom or have, or you just need to flush through this and have a fresh perspective.”
Jason Lemkin Aug 9, 2023 ▶ 1:12:39 Jason Lemkin: Every VC has a FRAUD in their portfolio; The IPO market is about to EXPLODE | E1046 · 20VC with Harry Stebbings
Aug 9, 2023 positive
Assertion Not checkable as stated
Lemkin: 90% of my investments over 10 years make money
“The average investment I make makes money. 90% of the time. Okay. Over 10 years.”
Jason Lemkin Aug 9, 2023 ▶ 43:36 Jason Lemkin: Every VC has a FRAUD in their portfolio; The IPO market is about to EXPLODE | E1046 · 20VC with Harry Stebbings
Aug 9, 2023
Disclosure
Lemkin asked a portfolio founder with 10 years runway to return money
“That one founder, the only one I did that had 10 years of runway, I asked him to give the money back.”
Jason Lemkin Aug 9, 2023 ▶ 37:43 Jason Lemkin: Every VC has a FRAUD in their portfolio; The IPO market is about to EXPLODE | E1046 · 20VC with Harry Stebbings
Aug 9, 2023 bullish
Disclosure
Lemkin: I deployed all my personal cash into public markets in 2023
“I deployed all my cash at the beginning of the year. Like I feel smart in the public markets. If I deployed it all at the peak, I would feel dumb, but I happen to have a lot of cash at the beginning of the year. I put it all in”
Jason Lemkin Aug 9, 2023 ▶ 48:42 Jason Lemkin: Every VC has a FRAUD in their portfolio; The IPO market is about to EXPLODE | E1046 · 20VC with Harry Stebbings
Aug 9, 2023
Disclosure
Lemkin rejected a 10-figure secondary offer for his SaaStr fund holdings
“I recently had a conversation with one of my LPs last week about a secondary offer. You know, that was 10 figures, a 10 figure secondary offer, ok? And we both agreed no was the answer.”
Jason Lemkin Aug 9, 2023 ▶ 59:54 Jason Lemkin: Every VC has a FRAUD in their portfolio; The IPO market is about to EXPLODE | E1046 · 20VC with Harry Stebbings
Aug 9, 2023 negative
Disclosure
Lemkin: Only 50% of my pre-revenue repeat founder investments make money
“The only pre revenue ones I've done are these repeat founders. These two X that had big exits that I know personally. So I know them personally. There's no ethics issues. I don't have to do any diligence. Only half of them are, have are going to make money.”
Jason Lemkin Aug 9, 2023 ▶ 43:46 Jason Lemkin: Every VC has a FRAUD in their portfolio; The IPO market is about to EXPLODE | E1046 · 20VC with Harry Stebbings
Aug 11, 2023 positive
Opinion
Lemkin: 2008 financial crisis was vastly worse for founders than 2023
“I think 08 09 as a founder was like 50 trillion times worse than today. 50. The world was ending in, you know, eight, oh nine.”
Jason Lemkin Aug 11, 2023 ▶ 54:41 DEBATE: State of Seed Investing w/ Jason Lemkin, Sam Lessin, Frank Rotman & Harry Stebbings | E1047 · 20VC with Harry Stebbings
Aug 11, 2023 negative
Opinion
Lemkin: Mega-Cap Tech CEOs Give Founders Better Feedback Than VCs
“That, that, you know, a 10 or a hundred billion dollar company CEO will actually respond thoughtfully. More than many VCs, frankly, who's just saying, good job.”
Jason Lemkin Aug 11, 2023 ▶ 43:15 DEBATE: State of Seed Investing w/ Jason Lemkin, Sam Lessin, Frank Rotman & Harry Stebbings | E1047 · 20VC with Harry Stebbings
Aug 11, 2023 negative
Opinion
Lemkin: All venture firm talent arms have failed
“See, in fact, I think that, like, all venture firms have failed with their talent arms.”
Jason Lemkin Aug 11, 2023 ▶ 46:54 DEBATE: State of Seed Investing w/ Jason Lemkin, Sam Lessin, Frank Rotman & Harry Stebbings | E1047 · 20VC with Harry Stebbings
Aug 11, 2023 positive
Disclosure
Lemkin: SaaStr fund has five portfolio companies exceeding $200M in revenue
“And I have, even me, I have five investments I've made North of two hundred million in revenue growing 30% or faster that are now efficient.”
Jason Lemkin Aug 11, 2023 ▶ 50:10 DEBATE: State of Seed Investing w/ Jason Lemkin, Sam Lessin, Frank Rotman & Harry Stebbings | E1047 · 20VC with Harry Stebbings
Aug 11, 2023 neutral
Disclosure
Lemkin: My Talkdesk investment memo capped its potential valuation at $150M
“I remember my first Decacorn talk desk, I wrote in the investment memo, this will never be worth more than a hundred and fifty million.”
Jason Lemkin Aug 11, 2023 ▶ 33:12 DEBATE: State of Seed Investing w/ Jason Lemkin, Sam Lessin, Frank Rotman & Harry Stebbings | E1047 · 20VC with Harry Stebbings
Aug 11, 2023 bullish
Prediction Partly held up
Lemkin: Tech companies will absorb $400M per IPO when markets recover
“When the engine revolves, we will absorb four hundred million again per IPO.”
Jason Lemkin Aug 11, 2023 ▶ 58:35 DEBATE: State of Seed Investing w/ Jason Lemkin, Sam Lessin, Frank Rotman & Harry Stebbings | E1047 · 20VC with Harry Stebbings
Aug 11, 2023 bearish
Opinion
Lemkin: Seed investors cannot make money without achieving 10%+ ownership
“That's my biggest stumbling block to investing is, like, there's so, like, I have to wait on too many deals where I can't get double digit ownerships. And I just don't believe I can make any money without it.”
Jason Lemkin Aug 11, 2023 ▶ 1:02:43 DEBATE: State of Seed Investing w/ Jason Lemkin, Sam Lessin, Frank Rotman & Harry Stebbings | E1047 · 20VC with Harry Stebbings
Aug 11, 2023 negative
Opinion
Lemkin: Seed founders are ignoring VC warnings and maintaining high valuation expectations
“I don't think any founders are listening to these terrific insights on Twitter, and I don't think that they are ratcheting back their valuation expectations, and I think very few are worried that when they do their seed at 30 post, that that will impact an A, …”
Jason Lemkin Aug 11, 2023 ▶ 12:11 DEBATE: State of Seed Investing w/ Jason Lemkin, Sam Lessin, Frank Rotman & Harry Stebbings | E1047 · 20VC with Harry Stebbings
Aug 11, 2023 bearish
Prediction Not checkable as stated
Lemkin: I am giving up on investing in Y Combinator startups
“I kind of have to give up on YC, not because I won't pay or don't love the signal, If there's 84 people in the round, there's no point in me putting a hundred grand in a 20 post.”
Jason Lemkin Aug 11, 2023 ▶ 41:13 DEBATE: State of Seed Investing w/ Jason Lemkin, Sam Lessin, Frank Rotman & Harry Stebbings | E1047 · 20VC with Harry Stebbings
Aug 11, 2023 bullish
Assertion Contradicted
Lemkin: Atlassian and MongoDB are bouncing off business bottoms
“When I look at what Atlassian is saying, like, they're bouncing off the bottom, and Mongo's bouncing off the bottom, and other folks are seeing things improve.”
Jason Lemkin Aug 11, 2023 ▶ 54:55 DEBATE: State of Seed Investing w/ Jason Lemkin, Sam Lessin, Frank Rotman & Harry Stebbings | E1047 · 20VC with Harry Stebbings
Aug 11, 2023 bearish
Opinion
Lemkin: Classic high-ownership seed deals yielding multi-billion outcomes are dead
“And my bigger concern is that I think those are deadish in seed. Right. Owning one percent is, is still good. One percent of forty billion is good, but that's the classic seed that I think we're griping about. Like, can we do trade desks today?”
Jason Lemkin Aug 11, 2023 ▶ 20:43 DEBATE: State of Seed Investing w/ Jason Lemkin, Sam Lessin, Frank Rotman & Harry Stebbings | E1047 · 20VC with Harry Stebbings
Aug 11, 2023 neutral
Assertion Contradicted
Lemkin: SaaS companies going public in 2019 absorbed $390M on average
“In 2019, the average SaaS company that went public absorbed just shy of four hundred million in capital, three hundred ninety million in capital before they went public.”
Jason Lemkin Aug 11, 2023 ▶ 58:21 DEBATE: State of Seed Investing w/ Jason Lemkin, Sam Lessin, Frank Rotman & Harry Stebbings | E1047 · 20VC with Harry Stebbings
Aug 11, 2023 negative
Opinion
Lemkin: Seed capital overabundance permanently ruined modern founders' respect for capital
“This farmification has changed the mentality of founders forever. Whether we're going back to forums or not, I don't think founders think the same way they used to. I don't think there's respect for capital.”
Jason Lemkin Aug 11, 2023 ▶ 29:56 DEBATE: State of Seed Investing w/ Jason Lemkin, Sam Lessin, Frank Rotman & Harry Stebbings | E1047 · 20VC with Harry Stebbings
Aug 23, 2023
Disclosure
Jason Lemkin limits founder pitch meetings to one per week
“And I have, I only actually, I'll read a 50 emails a week, but I only want to do one pitch a week. I only, if I can, that's my dream. And I find when I do two, three or four, the other three aren't worth it.”
Jason Lemkin Aug 23, 2023 ▶ 46:52 Jason Lemkin & Rick Zullo: How "Mark to Market" Corrupted Venture Capital | E1052 · 20VC with Harry Stebbings
Aug 23, 2023 negative
Prediction Not checkable as stated
Lemkin: Founders and Boards Will Regret Delaying Burn Rate Conversations
“In the end, people will have wished that conversation happened six to eight months ago, but ever the tenors changed. Everything's changed.”
Jason Lemkin Aug 23, 2023 ▶ 16:04 Jason Lemkin & Rick Zullo: How "Mark to Market" Corrupted Venture Capital | E1052 · 20VC with Harry Stebbings
Aug 23, 2023 negative
Disclosure
Jason Lemkin Refused Initial Pitch Meeting with monday.com Founders
“And I was on, you know, I did this catch up with the monday.com founders the other day and they showed me the pitch email they sent me. It was the worst ever when they were starting. It had a different name. It was terrible. It's like, We're thinking about doi…”
Jason Lemkin Aug 23, 2023 ▶ 41:35 Jason Lemkin & Rick Zullo: How "Mark to Market" Corrupted Venture Capital | E1052 · 20VC with Harry Stebbings
Aug 23, 2023 negative
Assertion Not checkable as stated
Lemkin: Raising a $20M round after a $50M seed is extremely difficult
“If your seed's at 50, it's really hard to raise the next round at 20.”
Jason Lemkin Aug 23, 2023 ▶ 8:37 Jason Lemkin & Rick Zullo: How "Mark to Market" Corrupted Venture Capital | E1052 · 20VC with Harry Stebbings
Aug 23, 2023 neutral
Assertion Not checkable as stated
Lemkin: Mega-funds displacing seed investors at inflated valuations is not new
“I actually don't think it's new. At least it's not new for second time founders, right? It's not new.”
Jason Lemkin Aug 23, 2023 ▶ 8:11 Jason Lemkin & Rick Zullo: How "Mark to Market" Corrupted Venture Capital | E1052 · 20VC with Harry Stebbings
Aug 23, 2023 negative
Assertion Not checkable as stated
Lemkin: 95% of founders ignore investor relations until needing bridge capital
“I think that that dynamic is lost on 95%, not all, but 95% of founders.”
Jason Lemkin Aug 23, 2023 ▶ 19:42 Jason Lemkin & Rick Zullo: How "Mark to Market" Corrupted Venture Capital | E1052 · 20VC with Harry Stebbings
Aug 23, 2023
Assertion Not checkable as stated
Lemkin took zero salary for 18 months to avoid company layoffs
“No, I took no salary for 18 months. Okay. I invested my own limited money from my first startup in my second.”
Jason Lemkin Aug 23, 2023 ▶ 11:28 Jason Lemkin & Rick Zullo: How "Mark to Market" Corrupted Venture Capital | E1052 · 20VC with Harry Stebbings
Aug 23, 2023 bullish
Prediction Not checkable as stated
Lemkin: SaaStr Will Return to 'Stair-Stepping' Investments Needing 3x Markups
“And that's what I'm going to get back to, right? A stair stepping deals, just stair stepping them, right? Twenty million post fine, but I got to know it's going to be 60.”
Jason Lemkin Aug 23, 2023 ▶ 56:52 Jason Lemkin & Rick Zullo: How "Mark to Market" Corrupted Venture Capital | E1052 · 20VC with Harry Stebbings
Aug 23, 2023
Insight
Lemkin: B2B Startups Cannot Skip 'Triple, Triple, Double, Double' Growth
“You can't have, whether the venture outcome is three hundred million or a billion or ten billion, you can't avoid triple, triple, double, double, at least in B to B. You can't avoid it. You can have a year gap. You literally can take a year off, but you can go…”
Jason Lemkin Aug 23, 2023 ▶ 26:33 Jason Lemkin & Rick Zullo: How "Mark to Market" Corrupted Venture Capital | E1052 · 20VC with Harry Stebbings
Aug 23, 2023 negative
Assertion Not checkable as stated
Lemkin: VCs cannot do real work taking 50 founder meetings weekly
“I mean, you can't do 50 meetings a week, no matter what they say on the internet. You can't, you can show up with no work. You can show up with a cup of coffee. You can't really do the work for 50 founders a week, right? You can't really do 2000 meetings a yea…”
Jason Lemkin Aug 23, 2023 ▶ 1:00:36 Jason Lemkin & Rick Zullo: How "Mark to Market" Corrupted Venture Capital | E1052 · 20VC with Harry Stebbings
Aug 23, 2023 bullish
Insight
Lemkin: Saturated Software Markets Require Founders to Force Entry Through Salesmanship
“In B to B, you got to sell, man. No one needs another SAS product. We already have 11 payroll companies and 88 CRMs and 96 mark. We don't need one. So if you can't force your way into a market and Selling stock is sales.”
Jason Lemkin Aug 23, 2023 ▶ 41:55 Jason Lemkin & Rick Zullo: How "Mark to Market" Corrupted Venture Capital | E1052 · 20VC with Harry Stebbings
Sep 20, 2023 neutral
Disclosure
Lemkin: Investing at $30M seed valuations requires a 50% hit rate
“Half of mine, at least half have to be winners, real winners, at least half. That's the insane, to make that, I'll do the 30 post, right, the 20 post, I'll do it, but I have to believe there that with a relatively high degree of certainty, it will be successfu…”
Jason Lemkin Sep 20, 2023 ▶ 33:57 Is the VC Model Broken? Jason Lemkin, Mike Maples, Eric Paley & Harry Stebbings Debate | E1062 · 20VC with Harry Stebbings
Sep 20, 2023
Disclosure
Lemkin: Had Three $1B Cash Exits and Zero IPOs Over 10 Years
“Well, look, I've only had, I've had three billion dollar cash exits and zero IPOs in 10 years.”
Jason Lemkin Sep 20, 2023 ▶ 1:22:20 Is the VC Model Broken? Jason Lemkin, Mike Maples, Eric Paley & Harry Stebbings Debate | E1062 · 20VC with Harry Stebbings
Sep 20, 2023
Disclosure
Lemkin: VP Candidates Frequently Do Not Know Their Startup's Operational Metrics
“I can't tell you how many VPs I interview all the time from my own portfolio companies, like ethical founders. And I asked them, well, what do you think of the metrics? They don't know them.”
Jason Lemkin Sep 20, 2023 ▶ 47:49 Is the VC Model Broken? Jason Lemkin, Mike Maples, Eric Paley & Harry Stebbings Debate | E1062 · 20VC with Harry Stebbings
Sep 20, 2023 negative
Disclosure
Lemkin: Multi-Billion Fund Refused 28 Board Meeting Requests for Top Startup
“I have one of my top investments right now, like, I mean, there's a few asterisks and downgrades, but there's nothing not to love, ok? Double digits in ARR, growing triple digits, A very multi-billion dollar fund led the pre-seed, right? Owns 15% of the compan…”
Jason Lemkin Sep 20, 2023 ▶ 55:27 Is the VC Model Broken? Jason Lemkin, Mike Maples, Eric Paley & Harry Stebbings Debate | E1062 · 20VC with Harry Stebbings
Sep 20, 2023 negative
Opinion
Lemkin: Founders lost perspective on next-round risk as VC gamified
“I don't think, I think founders have lost all perspective on the risk they're taking in the next round. Venture has been so gamified the last five years, and everyone's to blame.”
Jason Lemkin Sep 20, 2023 ▶ 41:54 Is the VC Model Broken? Jason Lemkin, Mike Maples, Eric Paley & Harry Stebbings Debate | E1062 · 20VC with Harry Stebbings
Sep 20, 2023 bearish
Prediction Not checkable as stated
Lemkin: Many unicorn founders will quiet quit under crushing valuations
“I, I'm, I think a lot of them will quiet quit. Like, I raised three hundred million and a billion. I can't see it, Eric. Like, I could see, great, there's a two hundred million dollar exit, and yeah, I'll get a carve out, and I'll make some money, but I can't …”
Jason Lemkin Sep 20, 2023 ▶ 51:03 Is the VC Model Broken? Jason Lemkin, Mike Maples, Eric Paley & Harry Stebbings Debate | E1062 · 20VC with Harry Stebbings
Sep 20, 2023 bullish
Prediction Partly held up
Lemkin: Tech Market Will See an IPO Week in H2 2024
“I have a lot of money with Harry that it's an IPO week in the second half of twenty-twenty-four.”
Jason Lemkin Sep 20, 2023 ▶ 1:10:41 Is the VC Model Broken? Jason Lemkin, Mike Maples, Eric Paley & Harry Stebbings Debate | E1062 · 20VC with Harry Stebbings
Sep 20, 2023 bullish
Prediction Didn’t hold up
Lemkin: Public tech leaders will increase headcount 20%+ next year
“I think average hiring will be like, 20% in public leaders next year. I think they'll be hiring 20% or more. I think layoffs are so far behind us. 20% or more I think the average public company will hire next year.”
Jason Lemkin Sep 20, 2023 ▶ 1:15:30 Is the VC Model Broken? Jason Lemkin, Mike Maples, Eric Paley & Harry Stebbings Debate | E1062 · 20VC with Harry Stebbings
Sep 20, 2023 neutral
Assertion Supported
Lemkin: Stuart Butterfield Offered to Return His Series A Capital
“I offered to give money back as a founder, right, for my Series A when I wasn't sure. They said keep it, right? Stuart Butterfield offered to give his back.”
Jason Lemkin Sep 20, 2023 ▶ 52:57 Is the VC Model Broken? Jason Lemkin, Mike Maples, Eric Paley & Harry Stebbings Debate | E1062 · 20VC with Harry Stebbings
Sep 20, 2023 negative
Opinion
Lemkin: Venture Capital Model Does Not Fully Work in B2B
“I actually don't think venture fully makes sense in B to B. I generally don't think it works”
Jason Lemkin Sep 20, 2023 ▶ 1:14:44 Is the VC Model Broken? Jason Lemkin, Mike Maples, Eric Paley & Harry Stebbings Debate | E1062 · 20VC with Harry Stebbings
Sep 20, 2023
Insight
Lemkin: Great founders accept max 20% valuation discount for preferred investors
“I think a great founder will take a 20%, will take a 20% lower or delta term sheet to work with a high, someone they really want to work with. Beyond 20, I think it may be mythical.”
Jason Lemkin Sep 20, 2023 ▶ 44:40 Is the VC Model Broken? Jason Lemkin, Mike Maples, Eric Paley & Harry Stebbings Debate | E1062 · 20VC with Harry Stebbings
Sep 20, 2023 bullish
Prediction Held up
Lemkin: Klaviyo will be worth close to $10 billion
“Klaviyo is going to be worth, I think, close to ten billion.”
Jason Lemkin Sep 20, 2023 ▶ 1:09:42 Is the VC Model Broken? Jason Lemkin, Mike Maples, Eric Paley & Harry Stebbings Debate | E1062 · 20VC with Harry Stebbings
Oct 11, 2023 bullish
Prediction Didn’t hold up
Jason Lemkin bets $10,000 that Klaviyo stock will rise 20% within 12 months
“I'll bet 10 grand to anyone that takes it that Klaviyo, 12 months from when this episode goes out or today, whatever Harry says, trades at 20% or higher from where it is today. I'll bet 10 grand it's 20% or higher.”
Jason Lemkin Oct 11, 2023 ▶ 52:53 Roundtable #4 with Jason Lemkin, Woody Marshall, Deven Parekh, Harry Stebbings | E1071 · 20VC with Harry Stebbings
Nov 3, 2023
Assertion Supported
Lemkin: 88% of SaaS companies have their founder as CEO at IPO
“88% of SaaS companies that have IPO'd have the founder as CEO at IPO.”
Jason Lemkin Nov 3, 2023 ▶ 10:03 Roundtable #5 with Jack Altman, Auren Hoffman, Jason Lemkin, Harry Stebbings | E1077 · 20VC with Harry Stebbings
Nov 3, 2023 neutral
Assertion Not checkable as stated
Jason Lemkin: Employees work the same amount today but are present less often
“I think sometimes I think people work less than they used to. I think they work the same. It's just, they're not present nearly as often.”
Jason Lemkin Nov 3, 2023 ▶ 40:49 Roundtable #5 with Jack Altman, Auren Hoffman, Jason Lemkin, Harry Stebbings | E1077 · 20VC with Harry Stebbings
Nov 3, 2023
Prediction Not checkable as stated
Jason Lemkin: Drops support when founder commitment drops below 100%
“As soon as it's less than a hundred, I decided I'm out. I'm immediate. I'm either quietly out or I'm introducing you to my board partner, Harry.”
Jason Lemkin Nov 3, 2023 ▶ 54:45 Roundtable #5 with Jack Altman, Auren Hoffman, Jason Lemkin, Harry Stebbings | E1077 · 20VC with Harry Stebbings
Nov 3, 2023 bullish
Prediction Held up
Lemkin wagers $2,000 that recent tech IPOs stay above IPO price
“I'll say all three are up. I'll go two grand on this one.”
Jason Lemkin Nov 3, 2023 ▶ 56:28 Roundtable #5 with Jack Altman, Auren Hoffman, Jason Lemkin, Harry Stebbings | E1077 · 20VC with Harry Stebbings
Nov 3, 2023 neutral
Assertion Supported
Lemkin: Data shows operator VCs do not outperform professional venture investors
“I remember a few years ago, I forget whose analysis was, there was no advantage, like, to being an operators were no better than professional. That may not include pre-seed, right, or other things. But it wasn't, when I wrote this up a few years ago, that what…”
Jason Lemkin Nov 3, 2023 ▶ 13:20 Roundtable #5 with Jack Altman, Auren Hoffman, Jason Lemkin, Harry Stebbings | E1077 · 20VC with Harry Stebbings
Nov 3, 2023
Insight
Lemkin: Founder-investors possess an innate ability to recognize superior talent
“That's the superpower that everyone on this on, on this podcast has, which is everyone knows who's better than them, right? That is one superpower that successful founders have that, that money investors, when I say they had, they don't even know what it means…”
Jason Lemkin Nov 3, 2023 ▶ 17:21 Roundtable #5 with Jack Altman, Auren Hoffman, Jason Lemkin, Harry Stebbings | E1077 · 20VC with Harry Stebbings
Nov 3, 2023 bearish
Insight
Lemkin: Operating as a full-stack solo VC is not optimal for scaling
“I started off completely full stack, right? I started off working at a third party VC firm all on my own loan guy, no help, right? Doing everything. And I've done that. And now I've seen after 10 years, it's not optimal, right?”
Jason Lemkin Nov 3, 2023 ▶ 20:39 Roundtable #5 with Jack Altman, Auren Hoffman, Jason Lemkin, Harry Stebbings | E1077 · 20VC with Harry Stebbings
Nov 3, 2023
Assertion Not checkable as stated
Jason Lemkin: Startups with committed founders and customers never fail
“If the founders are truly still giving it a hundred percent for real. I mean, a real 100%. I'm I'll never be out for a variety of reasons. Also, I've never seen those ones actually fail if they're a hundred percent committed and they have any customers.”
Jason Lemkin Nov 3, 2023 ▶ 54:08 Roundtable #5 with Jack Altman, Auren Hoffman, Jason Lemkin, Harry Stebbings | E1077 · 20VC with Harry Stebbings
Nov 3, 2023 neutral
Assertion Not checkable as stated
Lemkin: Sequoia and Kleiner Perkins historically demanded 20% valuation discounts
“When I started in the old, old days, there were only two brands in venture. I knew of there was Sequoia and Kleiner, right? And you had to take a discount for both of them, right? You'd go out and you'd get your term sheet from somebody else, and then Kleiner …”
Jason Lemkin Nov 3, 2023 ▶ 3:59 Roundtable #5 with Jack Altman, Auren Hoffman, Jason Lemkin, Harry Stebbings | E1077 · 20VC with Harry Stebbings
Jan 4, 2024 bearish
Opinion
Every crypto company offering an Earn program is a fraud
“I believe every crypto company that has an EARN program is a fraud.”
Jason Lemkin Jan 4, 2024 ▶ 14:24 Jason Lemkin: Predictions for 2024 - What Does a Trump Administration do for Startups? | E1099 · 20VC with Harry Stebbings
Jan 4, 2024 negative
Prediction Not checkable as stated
Lemkin: SaaStr will never again invest in 'pretty good' founders
“I have changed my mind that there is any chance on planet Earth, any chance That a pretty good founder can produce good venture returns. I will never again invest. I only invest in founders that are much better than me. I will never invest in pretty good found…”
Jason Lemkin Jan 4, 2024 ▶ 1:11:45 Jason Lemkin: Predictions for 2024 - What Does a Trump Administration do for Startups? | E1099 · 20VC with Harry Stebbings
Jan 4, 2024 bearish
Opinion
Lemkin: Coinbase's 10% high-yield crypto program is a pyramid scheme
“And even, I know Coinbase is the good one, but where are they getting this 10%? It's a pyramid scheme. It's fraud.”
Jason Lemkin Jan 4, 2024 ▶ 14:56 Jason Lemkin: Predictions for 2024 - What Does a Trump Administration do for Startups? | E1099 · 20VC with Harry Stebbings
Jan 4, 2024
Assertion Open
Sequoia still uses the lobby-waiting strategy to win competitive deals
“The classic Sequoia playbook, which literally happened to one of my portfolio companies a couple months ago, where they sit in the lobby and just wait, you know, with the term sheet. Sequoia still does it.”
Jason Lemkin Jan 4, 2024 ▶ 1:17:01 Jason Lemkin: Predictions for 2024 - What Does a Trump Administration do for Startups? | E1099 · 20VC with Harry Stebbings
Jan 4, 2024 negative
Assertion Not checkable as stated
Box CEO Aaron Levie says enterprise customers have zero AI budget
“I asked Aaron Levy when I talked to him, when you talk with your biggest customers, what's their AI budget? He's like, their AI budget is zero. There's no AI line.”
Jason Lemkin Jan 4, 2024 ▶ 48:35 Jason Lemkin: Predictions for 2024 - What Does a Trump Administration do for Startups? | E1099 · 20VC with Harry Stebbings
Jan 4, 2024 bullish
Prediction Not checkable as stated
Lemkin: Seed SaaS investing will stay vibrant with yearly 1,000x outcomes
“I think the vibrancy of seed is here to stay. There's too many folks that made money. There's too many folks that enjoy investing. There are too many LPs that are still going to search for that alpha. And there will, every year there's going to be thousand X o…”
Jason Lemkin Jan 4, 2024 ▶ 51:00 Jason Lemkin: Predictions for 2024 - What Does a Trump Administration do for Startups? | E1099 · 20VC with Harry Stebbings
Jan 4, 2024
Insight
Lemkin: Usually only one investor will step up to catalyze a round
“What I have seen in my, especially the last 24 months, but across my whole career of investing for 11 years, is there's usually only one investor that will stand up for you.”
Jason Lemkin Jan 4, 2024 ▶ 37:32 Jason Lemkin: Predictions for 2024 - What Does a Trump Administration do for Startups? | E1099 · 20VC with Harry Stebbings
Jan 4, 2024
Disclosure
Lemkin: Invested in six pre-seed startups now exceeding $200M revenue
“I think I've invested in six companies at the pre-seed states that are now north of two hundred million, ok? And so they're IPO candidates, ok?”
Jason Lemkin Jan 4, 2024 ▶ 17:28 Jason Lemkin: Predictions for 2024 - What Does a Trump Administration do for Startups? | E1099 · 20VC with Harry Stebbings
Jan 4, 2024 neutral
Disclosure
Lemkin: Pipedrive was my first venture investment and sold for $1.5B
“Pipedrive, which was my first venture investment, right? Which eventually sold for a billion and a half, but lost to HubSpot.”
Jason Lemkin Jan 4, 2024 ▶ 5:54 Jason Lemkin: Predictions for 2024 - What Does a Trump Administration do for Startups? | E1099 · 20VC with Harry Stebbings
Jan 4, 2024
Disclosure
SaaStr generated approximately $27 million in revenue in 2023
“Like twenty seven million the year before.”
Jason Lemkin Jan 4, 2024 ▶ 1:29:09 Jason Lemkin: Predictions for 2024 - What Does a Trump Administration do for Startups? | E1099 · 20VC with Harry Stebbings
Jan 4, 2024 neutral
Insight
Lemkin: VCs shouldn't invest unless convinced within 20 minutes
“If you don't know in 20 minutes that this is one of the best founders you've ever met with, don't do the investment.”
Jason Lemkin Jan 4, 2024 ▶ 1:14:13 Jason Lemkin: Predictions for 2024 - What Does a Trump Administration do for Startups? | E1099 · 20VC with Harry Stebbings
Jan 4, 2024 positive
Insight
Lemkin: The Best Venture Capital Investors Are Persistent Nudges
“The best investors are nudges.”
Jason Lemkin Jan 4, 2024 ▶ 1:16:59 Jason Lemkin: Predictions for 2024 - What Does a Trump Administration do for Startups? | E1099 · 20VC with Harry Stebbings
Jan 4, 2024 negative
Disclosure
Lemkin wrote off all non-performing investments in latest LP report
“So I took every write off in my last LP report. There was, I just wrote it off to the max. Anything that wasn't good for my first time, I just wrote it. I just, I aggressively put the red pen or whatever to it.”
Jason Lemkin Jan 4, 2024 ▶ 1:12:20 Jason Lemkin: Predictions for 2024 - What Does a Trump Administration do for Startups? | E1099 · 20VC with Harry Stebbings
Jan 4, 2024 negative
Insight
Lemkin: Venture capitalists shouldn't be overly involved as advisors
“I think you can, you shouldn't be too involved with portfolio companies. It's you have a portfolio. I shouldn't be an advisor.”
Jason Lemkin Jan 4, 2024 ▶ 1:21:20 Jason Lemkin: Predictions for 2024 - What Does a Trump Administration do for Startups? | E1099 · 20VC with Harry Stebbings
Jan 4, 2024 bullish
Disclosure
Lemkin: PE-owned tech companies are actively seeking $20M+ ARR bolt-on acquisitions
“I have seen lots of tire kicking across my portfolio in the last six months. A lot of it, not just from public companies, but a lot of it from ex-public companies that are acquired by PE. They're all looking to bolt stuff on. They're all looking to bolt stuff …”
Jason Lemkin Jan 4, 2024 ▶ 1:00:52 Jason Lemkin: Predictions for 2024 - What Does a Trump Administration do for Startups? | E1099 · 20VC with Harry Stebbings
Jan 4, 2024
Insight
Lemkin: Founders must evaluate growth relative to competitors, not in isolation
“You gotta judge your growth, not on an app, just on an absolute basis, but compared to your competitors.”
Jason Lemkin Jan 4, 2024 ▶ 1:31:06 Jason Lemkin: Predictions for 2024 - What Does a Trump Administration do for Startups? | E1099 · 20VC with Harry Stebbings
Jan 4, 2024 negative
Prediction Open · timeframe Jan 2029
Lemkin: Will not interview founders with under $20M in revenue
“This is why I won't even talk or interview a founder below 20 or thirty million in revenue because they're not honest enough. They don't have enough life experience, right?”
Jason Lemkin Jan 4, 2024 ▶ 12:07 Jason Lemkin: Predictions for 2024 - What Does a Trump Administration do for Startups? | E1099 · 20VC with Harry Stebbings
Jan 4, 2024
Disclosure
Lemkin: All $200M+ revenue portfolio startups reached cash flow positivity
“And most of them, not all, I mean, I'm not talking about hundreds, so maybe most of the wrong word, I would say a bunch of them are on the bubble, and what I mean is, they're all cash flow positive now, all of them, everyone got cash flow positive, ok?”
Jason Lemkin Jan 4, 2024 ▶ 17:38 Jason Lemkin: Predictions for 2024 - What Does a Trump Administration do for Startups? | E1099 · 20VC with Harry Stebbings
Jan 4, 2024 bearish
Disclosure
Lemkin: Expects to lose $70K bet on 2024 tech IPO resurgence
“And I have, you know, I've got 70,000 dollars with you that there'll be 26 IPOs next year. I think my, I think I may have been off by six months, so I'm going to lose.”
Jason Lemkin Jan 4, 2024 ▶ 18:05 Jason Lemkin: Predictions for 2024 - What Does a Trump Administration do for Startups? | E1099 · 20VC with Harry Stebbings
Jan 4, 2024 positive
Disclosure
Lemkin reveals 2013 Pipedrive seed terms and $1.5B exit outcome
“When I invested in pipe drive in 2013, my first investment It was 16 pre at 1.2 million ARR. Okay. Growing nine percent a month. Okay. And we argued over the price. Now, pros and cons, but it did exit for a billion and a half.”
Jason Lemkin Jan 4, 2024 ▶ 20:40 Jason Lemkin: Predictions for 2024 - What Does a Trump Administration do for Startups? | E1099 · 20VC with Harry Stebbings
Jan 4, 2024 bearish
Prediction Not checkable as stated
Lemkin: Another 2021-level venture boom could take a decade
“I think we're going to see 2021 again, and maybe AI will bring it back faster but it could be a decade until we see another boom of that level.”
Jason Lemkin Jan 4, 2024 ▶ 22:37 Jason Lemkin: Predictions for 2024 - What Does a Trump Administration do for Startups? | E1099 · 20VC with Harry Stebbings
Jan 4, 2024 positive
Insight
Lemkin: Founders should accept preemptive inside rounds most of the time
“And I think founders should take inside, like, good inside rounds very seriously now because of the reason you said. This is different than a bridge, but if one of your investors really wants to step up at a higher price, Right? Just eight, six times out of 10…”
Jason Lemkin Jan 4, 2024 ▶ 1:23:16 Jason Lemkin: Predictions for 2024 - What Does a Trump Administration do for Startups? | E1099 · 20VC with Harry Stebbings
Jan 4, 2024 bearish
Prediction Not checkable as stated
Lemkin will sell all seed shares if founders take huge secondaries
“And I would, if I, if I'm in that situation again, I will sell my shares as a seed investor. If I'm allowed, I would sell all of my shares. All of them. A hundred percent of my shares in that situation.”
Jason Lemkin Jan 4, 2024 ▶ 43:09 Jason Lemkin: Predictions for 2024 - What Does a Trump Administration do for Startups? | E1099 · 20VC with Harry Stebbings
Jan 4, 2024 negative
Assertion Not checkable as stated
Lemkin: Personal tax bill increased 15% under Donald Trump's presidency
“My taxes went up, whatever, 15% under Trump.”
Jason Lemkin Jan 4, 2024 ▶ 1:04:15 Jason Lemkin: Predictions for 2024 - What Does a Trump Administration do for Startups? | E1099 · 20VC with Harry Stebbings
Jan 4, 2024 bearish
Insight
Lemkin: Founder secondaries over $10 million are a bad sign
“If you're putting the rest first, I think taking out more than ten million is a bad sign, even in the hottest round.”
Jason Lemkin Jan 4, 2024 ▶ 41:57 Jason Lemkin: Predictions for 2024 - What Does a Trump Administration do for Startups? | E1099 · 20VC with Harry Stebbings
Jan 4, 2024 negative
Opinion
Lemkin: Hopin founder's $140M secondary cash-out was abusive and unethical
“The hop in story is abusive. I'll take a hundred and forty million out for myself. F you VCs. That's Writer. I know a lot of folks think that's a hero story. I think it's abusive.”
Jason Lemkin Jan 4, 2024 ▶ 39:40 Jason Lemkin: Predictions for 2024 - What Does a Trump Administration do for Startups? | E1099 · 20VC with Harry Stebbings
Jan 4, 2024
Disclosure
Lemkin: Byron Dieter Sat on My Steps With Term Sheet
“Byron Dieter did it with me back in the day at Bessemer of just sitting on your steps with the term sheet.”
Jason Lemkin Jan 4, 2024 ▶ 1:17:18 Jason Lemkin: Predictions for 2024 - What Does a Trump Administration do for Startups? | E1099 · 20VC with Harry Stebbings
May 27, 2024
Disclosure
Lemkin Has Never Seen an Enterprise SaaS Company at $1M ARR Below 100% NRR
“I've never not seen triple digit NRR at that scale. I've never not seen it, never in my career. My own experience as a founder or any company I've invested in, it's always triple digits in the enterprise.”
Jason Lemkin May 27, 2024 ▶ 53:04 Jason Lemkin: Why Pricing is Worse Than Ever and There is More Funding Than Ever | E1157 · 20VC with Harry Stebbings
May 27, 2024
Insight
Lemkin: Seed CEOs are better than CTOs 80% of the time
“Overall, I would say, 80% of the time, the CEO is better than the CTO, especially at the seed or early seed stage”
Jason Lemkin May 27, 2024 ▶ 11:50 Jason Lemkin: Why Pricing is Worse Than Ever and There is More Funding Than Ever | E1157 · 20VC with Harry Stebbings
May 27, 2024
Prediction Not checkable as stated
Jason Lemkin Pledges Never to Treat End-of-Fund Deals Differently Again
“So this was an end of fund thinking, and I will never approach an end of fund investment treating it any differently than the start of fund investment. I will never do that again.”
Jason Lemkin May 27, 2024 ▶ 1:11:00 Jason Lemkin: Why Pricing is Worse Than Ever and There is More Funding Than Ever | E1157 · 20VC with Harry Stebbings
May 27, 2024 neutral
Disclosure
Lemkin: Zero overlap between top investments by cash vs NAV
“My best by cash and best by NAV are not, there's no overlap yet.”
Jason Lemkin May 27, 2024 ▶ 2:10 Jason Lemkin: Why Pricing is Worse Than Ever and There is More Funding Than Ever | E1157 · 20VC with Harry Stebbings
May 27, 2024 neutral
Insight
Lemkin: Customer calls should only confirm VC conviction, not fix marginal deals
“I'm not looking for a customer call To turn a frown upside down. I'm not looking at to take a marginal investment. This is, I think what VCs used to do in the old days is they'd hope, right? I'm looking only for confirmation with customers.”
Jason Lemkin May 27, 2024 ▶ 42:25 Jason Lemkin: Why Pricing is Worse Than Ever and There is More Funding Than Ever | E1157 · 20VC with Harry Stebbings
May 27, 2024 negative
Disclosure
Jason Lemkin Lost $5M on Startup That Fired Sales Team with $15M Banked
“And then this five million dollar company, one day they came into work and they fired their entire sales and marketing team. With fifteen million dollars in the bank, they fired everyone, just like Elon, but Elon's a better founder, fired a supercharger team. …”
Jason Lemkin May 27, 2024 ▶ 1:09:43 Jason Lemkin: Why Pricing is Worse Than Ever and There is More Funding Than Ever | E1157 · 20VC with Harry Stebbings
May 27, 2024
Disclosure
Lemkin Passes on 100% of SaaS Startups with Abnormally High Churn
“I have passed on every single company that had For their segment, abnormally high churn, a hundred percent.”
Jason Lemkin May 27, 2024 ▶ 54:24 Jason Lemkin: Why Pricing is Worse Than Ever and There is More Funding Than Ever | E1157 · 20VC with Harry Stebbings
May 27, 2024
Insight
Lemkin: Seed investments face 50% dilution before IPO
“Really in today's world, you're going to suffer 50% dilution on the way to IPO. That core seed fund that you struggled to get 12% of, you know, it could be six by the IPO.”
Jason Lemkin May 27, 2024 ▶ 13:15 Jason Lemkin: Why Pricing is Worse Than Ever and There is More Funding Than Ever | E1157 · 20VC with Harry Stebbings
May 27, 2024 negative
Insight
Lemkin: Software quality issues at $1M ARR get worse by $10M ARR
“When I see these signs that the software isn't good at a million, it rarely gets better at 10. It gets worse. The load goes up. The workflows go up.”
Jason Lemkin May 27, 2024 ▶ 19:08 Jason Lemkin: Why Pricing is Worse Than Ever and There is More Funding Than Ever | E1157 · 20VC with Harry Stebbings
May 27, 2024
Disclosure
Lemkin Shifts CTO Due Diligence Call to Second Meeting
“In the old days, I would do it late in the process. I would get to know the CO would talk to the customers, right? I would go deep and then at the very end, I'd be like, okay, I gotta talk to your CTO Harry to make sure that this is real. Now I immediately ski…”
Jason Lemkin May 27, 2024 ▶ 7:42 Jason Lemkin: Why Pricing is Worse Than Ever and There is More Funding Than Ever | E1157 · 20VC with Harry Stebbings
May 27, 2024 neutral
Disclosure
Lemkin Confused RevenueCat's GMV With ARR When Investing
“I misunderstood. I confused their, basically their GMV with their ARR. I got it wrong. So I thought they were doing like 10,000 dollars a month in MRR, but they were doing managing 10,000 dollars a month in subscriptions and making like 30 dollars.”
Jason Lemkin May 27, 2024 ▶ 1:07:18 Jason Lemkin: Why Pricing is Worse Than Ever and There is More Funding Than Ever | E1157 · 20VC with Harry Stebbings
May 27, 2024 negative
Opinion
Lemkin: You can build a unicorn bullshitting, but the best founders don't
“I think you can build a unicorn bullshitting, but I don't think the best founders bullshit.”
Jason Lemkin May 27, 2024 ▶ 40:28 Jason Lemkin: Why Pricing is Worse Than Ever and There is More Funding Than Ever | E1157 · 20VC with Harry Stebbings
May 27, 2024
Prediction Not checkable as stated
Lemkin Will Never Invest Without Two Deeply Committed Co-Founders
“Finding what I will never sacrifice again is two great co-founders. Two great co-founders, and not great numbers are great, but insane level commitment.”
Jason Lemkin May 27, 2024 ▶ 6:37 Jason Lemkin: Why Pricing is Worse Than Ever and There is More Funding Than Ever | E1157 · 20VC with Harry Stebbings
May 27, 2024 positive
Disclosure
Lemkin: First five investments all reached billion-dollar valuations
“Even though my first five investments all worth a billion or more for real, real billions”
Jason Lemkin May 27, 2024 ▶ 13:39 Jason Lemkin: Why Pricing is Worse Than Ever and There is More Funding Than Ever | E1157 · 20VC with Harry Stebbings
May 27, 2024 negative
Disclosure
Lemkin: Lost $5 million on startup that improperly recognized annual revenue upfront
“This five million dollar loss when you take 12 months of revenue and you recognize it all in one month, that's at the edge of fraud, isn't it?”
Jason Lemkin May 27, 2024 ▶ 40:39 Jason Lemkin: Why Pricing is Worse Than Ever and There is More Funding Than Ever | E1157 · 20VC with Harry Stebbings
May 27, 2024
Insight
Lemkin: Great CTOs Instantly Identify Their Product's Weaknesses
“Asking the CTO what they, what frustrates them and their product is very telling. The great CTOs will answer in 60 seconds.”
Jason Lemkin May 27, 2024 ▶ 10:07 Jason Lemkin: Why Pricing is Worse Than Ever and There is More Funding Than Ever | E1157 · 20VC with Harry Stebbings
May 27, 2024 negative
Prediction Not checkable as stated
Lemkin Will Liquidate Positions as Soon as Founders Depart
“For now, for me, right or wrong, if the founders leave, I will liquidate my position as soon as it's significant, right?”
Jason Lemkin May 27, 2024 ▶ 25:58 Jason Lemkin: Why Pricing is Worse Than Ever and There is More Funding Than Ever | E1157 · 20VC with Harry Stebbings
May 27, 2024 neutral
Insight
Lemkin: Seed investors should only evaluate CEO and CTO quality
“If I'm invested in someone with 10 employees or less, I don't care anymore what the management is, but I do care what the CTO is the one I care about.”
Jason Lemkin May 27, 2024 ▶ 15:43 Jason Lemkin: Why Pricing is Worse Than Ever and There is More Funding Than Ever | E1157 · 20VC with Harry Stebbings
May 27, 2024
Insight
Lemkin attributes all VC losses to founders lacking multi-decade commitment
“Those are the investments where I just don't think you can lose, and when I've, my losses, to tie this all into the theme, my losses are when the founders weren't that way.”
Jason Lemkin May 27, 2024 ▶ 1:09:15 Jason Lemkin: Why Pricing is Worse Than Ever and There is More Funding Than Ever | E1157 · 20VC with Harry Stebbings
May 27, 2024 negative
What-if
Lemkin Regrets Distributing $100M Exit Instead of Recycling Into Seed Fund
“I should have recycled all that money instead of distribute it. It was impactful to a seed fund, right? Cause it was a significant return. But it was so, it was early in the life cycle of the fund. And now I wish I had those tens of millions to put into the po…”
Jason Lemkin May 27, 2024 ▶ 1:11:22 Jason Lemkin: Why Pricing is Worse Than Ever and There is More Funding Than Ever | E1157 · 20VC with Harry Stebbings
Jun 3, 2024 negative
Disclosure
Lemkin: SaaStr will generate around $25 million in revenue in 2024
“This will be our first crappy year, but like twenty five million.”
Jason Lemkin Jun 3, 2024 ▶ 1:03:25 Jason Lemkin: PluralSight S*** the Bed & The Next IPO Candidates | E1160 · 20VC with Harry Stebbings
Jun 3, 2024 neutral
Disclosure
Lemkin: 2024 Brings His First-Ever Venture Investment Write-Offs
“This will be the first year I've ever had any investments that I had to write off was this year, but the funds will still do fine, right?”
Jason Lemkin Jun 3, 2024 ▶ 12:05 Jason Lemkin: PluralSight S*** the Bed & The Next IPO Candidates | E1160 · 20VC with Harry Stebbings
Jun 3, 2024 bullish
Prediction Didn’t hold up
Lemkin bets $20k that public SaaS multiples reach 8x by end of 2025
“Yeah, I'll do 20 grand at 12:31. At the end of 2025, we're back to an eight X world.”
Jason Lemkin Jun 3, 2024 ▶ 1:19:52 Jason Lemkin: PluralSight S*** the Bed & The Next IPO Candidates | E1160 · 20VC with Harry Stebbings
Jun 3, 2024 positive
Opinion
Lemkin: Shopify's Tobi Lütke is the ideal board member over founder-friendly VCs
“I think I'd pick Toby from Shopify. Cause I think he'd frigging kick my ass. We have too many founder friendly Yahoo. Great job. Harry's on boards. I I'm just so sick of it. Toby just seems like he just doesn't suffer fools. And maybe you don't want to work. M…”
Jason Lemkin Jun 3, 2024 ▶ 1:16:55 Jason Lemkin: PluralSight S*** the Bed & The Next IPO Candidates | E1160 · 20VC with Harry Stebbings
Jun 3, 2024 bearish
Assertion Supported
Lemkin: SaaS incumbents see no revenue boost from AI features yet
“So far the evidence is no. So far it says the incumbents are gonna, they're gonna do great things with AI, great, great things. The product's gonna be much better, but it's not clear they're gonna get any revenue boost from it. No one's saying that none of the…”
Jason Lemkin Jun 3, 2024 ▶ 24:36 Jason Lemkin: PluralSight S*** the Bed & The Next IPO Candidates | E1160 · 20VC with Harry Stebbings
Jun 3, 2024 negative
Opinion
Lemkin: I have become a worse CEO over time due to impatience
“Because I'm not, I care much more. I care like 20 times more about my team than I used to. But I can't bullshit anymore. I can't tell people it's great. Great job. Great. I know we showed up on a Saturday and no one was here, but great job team. I can't, I'm t…”
Jason Lemkin Jun 3, 2024 ▶ 1:14:01 Jason Lemkin: PluralSight S*** the Bed & The Next IPO Candidates | E1160 · 20VC with Harry Stebbings
Jun 3, 2024 negative
Disclosure
Lemkin: I have never made a successful investment from a cold email
“No, but that might be my flaw.”
Jason Lemkin Jun 3, 2024 ▶ 1:01:46 Jason Lemkin: PluralSight S*** the Bed & The Next IPO Candidates | E1160 · 20VC with Harry Stebbings
Jun 3, 2024
Insight
Lemkin: SaaS micro-brands get 50% free leads by $2M revenue
“Well, I actually find it happens by a couple million in revenue. You often will get half of your deals from not just inbound deals, but folks that heard about you. Folks that in your little niche that have not, not in the grand scheme of things, no one's heard…”
Jason Lemkin Jun 3, 2024 ▶ 49:09 Jason Lemkin: PluralSight S*** the Bed & The Next IPO Candidates | E1160 · 20VC with Harry Stebbings
Jun 3, 2024 negative
Insight
Lemkin: SaaS founders who ignore AI are on a path to destruction
“If you resist this, you are going to get steamrolled because the customers expect it. They're looking for it. How they pay for it is a different question, but I see too many founders still hiding or running from AI or mocking it or making fun of it. And I thin…”
Jason Lemkin Jun 3, 2024 ▶ 25:29 Jason Lemkin: PluralSight S*** the Bed & The Next IPO Candidates | E1160 · 20VC with Harry Stebbings
Jun 3, 2024 negative
Insight
Lemkin: Seed investors should not sell secondary shares before a $1B valuation
“I think that there's no point in even as a seed investor selling before a billion. It's not enough money.”
Jason Lemkin Jun 3, 2024 ▶ 40:49 Jason Lemkin: PluralSight S*** the Bed & The Next IPO Candidates | E1160 · 20VC with Harry Stebbings
Jun 3, 2024 negative
Assertion Partly supported
Lemkin: AI enterprise spending is entirely taken from traditional SaaS budgets
“It is all being taken. There is no net new. There is no net new.”
Jason Lemkin Jun 3, 2024 ▶ 9:02 Jason Lemkin: PluralSight S*** the Bed & The Next IPO Candidates | E1160 · 20VC with Harry Stebbings
Jun 3, 2024 negative
Insight
Lemkin: Individual Investors Should Never Invest in VC Funds
“This is why I tell almost every individual do not invest in venture funds. It's dumb for individuals.”
Jason Lemkin Jun 3, 2024 ▶ 35:14 Jason Lemkin: PluralSight S*** the Bed & The Next IPO Candidates | E1160 · 20VC with Harry Stebbings
Jun 3, 2024 neutral
Disclosure
Lemkin aggressively cut his venture portfolio valuations at year-end 2023
“At the end of 1231, I marked, I took a Big red marker, and I went overboard. I cut everything that needed to be cut. In fact, I just had a liquidity, I mean, an extremely minor liquidity event, and it's, you know, it's three times what I marked it down to in D…”
Jason Lemkin Jun 3, 2024 ▶ 45:39 Jason Lemkin: PluralSight S*** the Bed & The Next IPO Candidates | E1160 · 20VC with Harry Stebbings
Jun 3, 2024 negative
Insight
Lemkin: Founders covering for mediocre VP performance in board meetings have quiet quit
“When you've acquiesced to having a mediocre management team, it's over. How are you ever going to regrow if you're with a mediocre management team? So when you start covering for a mediocre management team, I'm not saying fire them. That's a more nuanced topic…”
Jason Lemkin Jun 3, 2024 ▶ 1:17:31 Jason Lemkin: PluralSight S*** the Bed & The Next IPO Candidates | E1160 · 20VC with Harry Stebbings
Jun 3, 2024
Insight
Lemkin: VCs Only See One Exceptional Startup Deal Per Month
“Two good ones, really good ones a week, and if you're lucky if you get an insane one a month.”
Jason Lemkin Jun 3, 2024 ▶ 1:01:31 Jason Lemkin: PluralSight S*** the Bed & The Next IPO Candidates | E1160 · 20VC with Harry Stebbings
Jun 3, 2024 bullish
Opinion
Lemkin: I would buy ZoomInfo stock because of founder Henry Schuck's commitment
“Generally speaking, when you have great founders that are committed, I'm a buyer, so I would buy. There's negative things, but like Henry's a great founder who's done this from scratch, basically bootstrapped all the way here, totally committed to the space, w…”
Jason Lemkin Jun 3, 2024 ▶ 55:28 Jason Lemkin: PluralSight S*** the Bed & The Next IPO Candidates | E1160 · 20VC with Harry Stebbings
Jun 3, 2024 negative
Insight
Lemkin: VCs should never invest unless they can see the future through the founder
“You should never do anyone where you can't see the future through the founders.”
Jason Lemkin Jun 3, 2024 ▶ 1:16:39 Jason Lemkin: PluralSight S*** the Bed & The Next IPO Candidates | E1160 · 20VC with Harry Stebbings
Jun 3, 2024 positive
Assertion Not checkable as stated
Lemkin: There Are More Good Startups Than Ever Before
“There's more good startups than ever”
Jason Lemkin Jun 3, 2024 ▶ 1:01:17 Jason Lemkin: PluralSight S*** the Bed & The Next IPO Candidates | E1160 · 20VC with Harry Stebbings
Jun 3, 2024
Insight
Lemkin: Top enterprise salespeople ask if software purchases are budgeted on first call
“All the best salespeople ask that question. On a first discovery call, Harry, when I'm meeting an enterprise customer, so tell me, is, is this purchase budgeted for this year?”
Jason Lemkin Jun 3, 2024 ▶ 10:36 Jason Lemkin: PluralSight S*** the Bed & The Next IPO Candidates | E1160 · 20VC with Harry Stebbings
Jun 3, 2024 neutral
Prediction Not checkable as stated
Lemkin: AI revenue impact on SaaS will take 24-36 months to clarify
“So it is where it is worrisome and there is an experiment budget and it is a substitution budget. And I think it's going to take us another 24 to 36 months to figure it out.”
Jason Lemkin Jun 3, 2024 ▶ 24:57 Jason Lemkin: PluralSight S*** the Bed & The Next IPO Candidates | E1160 · 20VC with Harry Stebbings
Jul 24, 2024
Disclosure
Lemkin says product outages were the main reason he sold his startup
“You know, Harry, it was the number one thing, reason I wanted to sell my startup was for these issues.”
Jason Lemkin Jul 24, 2024 ▶ 31:29 Jason Lemkin: Crowdstrike, WTF Happens From Here? Wiz Rejects Google’s $23BN Acquisition Offer|E1181 · 20VC with Harry Stebbings
Jul 24, 2024 neutral
Prediction Not checkable as stated
Lemkin: 2025 will be the year of SaaS AI feature parity
“I think 2025 will be the year of SaaS AI parity. Everything's gonna be parity in 2025. Not total parity, but close to parity, right?”
Jason Lemkin Jul 24, 2024 ▶ 38:31 Jason Lemkin: Crowdstrike, WTF Happens From Here? Wiz Rejects Google’s $23BN Acquisition Offer|E1181 · 20VC with Harry Stebbings
Jul 24, 2024 positive
Insight
Lemkin: Startup founders should accept any decent exit offer immediately
“Since 2021. Every founder with a decent exit, I tell them to take it now. A hundred percent. I tell them to take it for this reason.”
Jason Lemkin Jul 24, 2024 ▶ 11:14 Jason Lemkin: Crowdstrike, WTF Happens From Here? Wiz Rejects Google’s $23BN Acquisition Offer|E1181 · 20VC with Harry Stebbings
Jul 24, 2024 bearish
Prediction Not checkable as stated
Lemkin: B2B AI market hype will calm down within a year
“And that's why I think in B to B AI is going to really calm down in a year, right?”
Jason Lemkin Jul 24, 2024 ▶ 40:14 Jason Lemkin: Crowdstrike, WTF Happens From Here? Wiz Rejects Google’s $23BN Acquisition Offer|E1181 · 20VC with Harry Stebbings
Jul 24, 2024 negative
Disclosure
Lemkin says his biggest tech regret is not being a better recruiter
“It's my number one regret in life, in tech, is not being a better recruiter.”
Jason Lemkin Jul 24, 2024 ▶ 48:23 Jason Lemkin: Crowdstrike, WTF Happens From Here? Wiz Rejects Google’s $23BN Acquisition Offer|E1181 · 20VC with Harry Stebbings
Jul 24, 2024 bullish
Disclosure
Lemkin says Wiz and ServiceTitan are the top private investments he missed
“I would take whiz and service Titan.”
Jason Lemkin Jul 24, 2024 ▶ 46:42 Jason Lemkin: Crowdstrike, WTF Happens From Here? Wiz Rejects Google’s $23BN Acquisition Offer|E1181 · 20VC with Harry Stebbings
Feb 3, 2025 negative
Opinion
Hyatt: Treating venture capital as a packaging industry is a losing strategy
“I hate that analogy deeply. Well, I to a certain extent- I understand it. I don't think it's good for startups and I don't think it's good for founders. And I also, maybe more importantly than just some kind of value judgment, I think it's a losing strategy wh…”
Nabeel Hyatt Feb 3, 2025 ▶ 9:08 Nabeel Hyatt, GP @ Spark Capital: To Win in AI, Investors Need to Change Their Approach | E1255 · 20VC with Harry Stebbings
Apr 3, 2025 negative
Assertion Not checkable as stated
Lemkin: 80% of B2B VCs reject traditional SaaS growth deals today
“For B to B investors that you and I know well, I mean, you know, everybody, Harry, but I would say 80% of them won't touch a triple, triple, double, double deal today.”
Jason Lemkin Apr 3, 2025 ▶ 15:02 20VC: The Daily Deal: Coreweave IPO | Scale Hits $25BN on $2BN EOY Revenue | Sequoia's 25x Return on Wiz | Tech Stocks Tank with Tariffs | Cursor: Defensible or Dangerous Example of Lost Moats in Tech
Apr 3, 2025 neutral
Assertion Contradicted
Lemkin: Public B2B SaaS companies averaged 70% growth in 2021
“The average public B to B stock was growing 70% in 2021. Public. I'm not talking about Cursor, or I'm talking about moldy oldies. The moldy oldies of SaaS were growing 70% in twenty-twenty-one.”
Jason Lemkin Apr 3, 2025 ▶ 4:40 20VC: The Daily Deal: Coreweave IPO | Scale Hits $25BN on $2BN EOY Revenue | Sequoia's 25x Return on Wiz | Tech Stocks Tank with Tariffs | Cursor: Defensible or Dangerous Example of Lost Moats in Tech
Apr 3, 2025 bullish
Prediction Not checkable as stated
Lemkin: Software expanding to 4% GDP will create 100+ decacorns
“I do believe if this trend of software going from two percent to four percent of GDP that they point out, that, that's going to birth a hundred decacorns, a hundred or more, and it is the golden age of software.”
Jason Lemkin Apr 3, 2025 ▶ 5:12 20VC: The Daily Deal: Coreweave IPO | Scale Hits $25BN on $2BN EOY Revenue | Sequoia's 25x Return on Wiz | Tech Stocks Tank with Tariffs | Cursor: Defensible or Dangerous Example of Lost Moats in Tech
Apr 3, 2025 negative
Assertion Partly supported
Lemkin: CoreWeave's late investors hold a 70% two-year stock buyback put option
“The last round investors. Obviously they weren't fully aligned on the price, right? And so there's structure and I don't think this is a bad thing. It's okay for late stage investors to be more conservative on price than founders. Like, and so they agreed on a…”
Jason Lemkin Apr 3, 2025 ▶ 1:06:23 20VC: The Daily Deal: Coreweave IPO | Scale Hits $25BN on $2BN EOY Revenue | Sequoia's 25x Return on Wiz | Tech Stocks Tank with Tariffs | Cursor: Defensible or Dangerous Example of Lost Moats in Tech
Apr 3, 2025
Disclosure
Lemkin: Nearly all his venture liquidity occurred in 2021
“So all, as an investor, all my liquidity was basically in twenty-twenty-one.”
Jason Lemkin Apr 3, 2025 ▶ 13:33 20VC: The Daily Deal: Coreweave IPO | Scale Hits $25BN on $2BN EOY Revenue | Sequoia's 25x Return on Wiz | Tech Stocks Tank with Tariffs | Cursor: Defensible or Dangerous Example of Lost Moats in Tech
Apr 3, 2025 bearish
Prediction Open · timeframe Apr 2030
Lemkin: Public B2B SaaS growth will never reach 2021 levels again
“We'll never see that again.”
Jason Lemkin Apr 3, 2025 ▶ 4:55 20VC: The Daily Deal: Coreweave IPO | Scale Hits $25BN on $2BN EOY Revenue | Sequoia's 25x Return on Wiz | Tech Stocks Tank with Tariffs | Cursor: Defensible or Dangerous Example of Lost Moats in Tech
Apr 3, 2025 negative
Opinion
Lemkin: YC advising founders to run tight fundraising processes is terrible advice
“I think it's some of the worst advice founders get. And I love Y Combinator, but I think it's some of the worst advice Y Combinator gives their founders too, which is run a tight process.”
Jason Lemkin Apr 3, 2025 ▶ 19:24 20VC: The Daily Deal: Coreweave IPO | Scale Hits $25BN on $2BN EOY Revenue | Sequoia's 25x Return on Wiz | Tech Stocks Tank with Tariffs | Cursor: Defensible or Dangerous Example of Lost Moats in Tech
Apr 17, 2025 negative
Assertion Not checkable as stated
Lemkin: Acquirers in nine-figure deals aggressively circumvent VC preferences
“My limited visibility recently in M&A is that every acquirer is looking for ways to get around all the VC preference. It's aggressive. Like it was always true, but now it's like super aggressive. It's like, we just don't Even give a rat's ass in corp dev how t…”
Jason Lemkin Apr 17, 2025 ▶ 1:13:03 a16z's $20BN Fund & Founders Fund's $4.6BN & Why Josh Kushner Has Mastered the Game · 20VC with Harry Stebbings
Apr 17, 2025 neutral
Disclosure
O'Driscoll: Scale's portfolio companies bypass VC preferences in acqui-hires
“When I'm on the other side of the table and my late stage companies are trying to buy early stage companies, I do exactly the same thing. I don't give a shit about Jason and his bloody preference. I want to hire those five great engineers. Let's just give them…”
Rory O'Driscoll Apr 17, 2025 ▶ 1:14:26 a16z's $20BN Fund & Founders Fund's $4.6BN & Why Josh Kushner Has Mastered the Game · 20VC with Harry Stebbings
Apr 17, 2025 bullish
Disclosure
Lemkin: Will invest in triple-triple-double-double SaaS if CEO is exceptional
“For me, the triple triple double double, I'm totally into it if the CEO is amazing.”
Jason Lemkin Apr 17, 2025 ▶ 14:57 a16z's $20BN Fund & Founders Fund's $4.6BN & Why Josh Kushner Has Mastered the Game · 20VC with Harry Stebbings
Apr 17, 2025 bearish
Assertion Not checkable as stated
Lemkin: 80% of legacy SaaS VCs now exclusively invest in AI
“I would say 70 to 80% of the folks I grew up with that were SaaS investors are not, won't do those normal triple triple double doubles. You would, and you're, you are a top tier performer, but they're just, they're momentum investors. And they want to put two …”
Jason Lemkin Apr 17, 2025 ▶ 15:30 a16z's $20BN Fund & Founders Fund's $4.6BN & Why Josh Kushner Has Mastered the Game · 20VC with Harry Stebbings
Apr 17, 2025
Insight
Lemkin: Startup product-market fit duration compressed from five years to five weeks
“It used to take you five years to follow the product market fit. Now it can be five weeks.”
Jason Lemkin Apr 17, 2025 ▶ 6:01 a16z's $20BN Fund & Founders Fund's $4.6BN & Why Josh Kushner Has Mastered the Game · 20VC with Harry Stebbings
Apr 17, 2025 neutral
Disclosure
Lemkin: Late-stage fund matched my seed stake with nine-figure unicorn check
“I just have a company that's just become a unicorn and a late stage fund just put in almost nine figures. Okay. And they own as much as me.”
Jason Lemkin Apr 17, 2025 ▶ 39:30 a16z's $20BN Fund & Founders Fund's $4.6BN & Why Josh Kushner Has Mastered the Game · 20VC with Harry Stebbings
Apr 17, 2025 positive
Disclosure
Lemkin: Top portfolio startups work 12-hour days, seven days a week in-office
“All the best startups I've invested in are working seven days a week, 12 hours a day in the office, seven days a week, 12 hours a day.”
Jason Lemkin Apr 17, 2025 ▶ 8:10 a16z's $20BN Fund & Founders Fund's $4.6BN & Why Josh Kushner Has Mastered the Game · 20VC with Harry Stebbings
Apr 17, 2025 negative
Disclosure
Lemkin: All my venture investments above $100M valuation have performed poorly
“I recently took a look at my investments. I just, I can't make any decision well north of a hundred, so I'm out. All of my decisions are bad. North of a hundred, they're just all bad for a variety of reasons.”
Jason Lemkin Apr 17, 2025 ▶ 1:31:44 a16z's $20BN Fund & Founders Fund's $4.6BN & Why Josh Kushner Has Mastered the Game · 20VC with Harry Stebbings
Apr 17, 2025 bearish
Prediction Not checkable as stated
Lemkin: A hundred corporate espionage and founder fraud cases will surface
“I think you're going to hear a hundred, just like fraud. Like every day now we pull up the media and there's another founder that stole thirty million from the investors and we shrug it off. Right. There's going to be a hundred of these in this environment.”
Jason Lemkin Apr 17, 2025 ▶ 1:23:24 a16z's $20BN Fund & Founders Fund's $4.6BN & Why Josh Kushner Has Mastered the Game · 20VC with Harry Stebbings
Apr 17, 2025 negative
Disclosure
Lemkin: Cloud VC offered nine-figure term sheets without speaking to founders
“Literally, I had two startups in my portfolio, two of them that a VC, all three of us know really about, one of the best cloud VCs, he offered them, I remember term sheets at high nine-figure valuations without talking to the founders, just immediately in late…”
Jason Lemkin Apr 17, 2025 ▶ 3:28 a16z's $20BN Fund & Founders Fund's $4.6BN & Why Josh Kushner Has Mastered the Game · 20VC with Harry Stebbings
Apr 17, 2025 positive
Insight
O'Driscoll: Megafunds with forgiving LPs should pursue late-stage investing over seed
“If you have access to capital that's large and forgiving, which is what these mega funds have, then you should play the big balls game. Cause you're exactly right. You don't do it. You have to do less work. If it works great, you make out the same as Jason who…”
Rory O'Driscoll Apr 17, 2025 ▶ 41:11 a16z's $20BN Fund & Founders Fund's $4.6BN & Why Josh Kushner Has Mastered the Game · 20VC with Harry Stebbings
Apr 24, 2025 negative
Opinion
Lemkin: AI roll-up revenue is financial engineering rather than durable growth
“They're not going to, it's not durable revenue in any way, shape or form, right? So it's financial engineering is all in most cases.”
Jason Lemkin Apr 24, 2025 ▶ 55:12 How LP Deployment to Venture Will Change in 2025 & Are Endowment Funds in Trouble? · 20VC with Harry Stebbings
Apr 24, 2025 bearish
Opinion
Lemkin: Enterprise plays in SMB markets like Olo lack fundable TAM
“Olo is trying to do an, basically an enterprise play in an SMB market. That's really brutal, right? It's the same problem in anything in B to B e-commerce. If you're doing, if you're not doing some SMB in e-commerce, like, yeah, there's a few niche players, bu…”
Jason Lemkin Apr 24, 2025 ▶ 1:24:34 How LP Deployment to Venture Will Change in 2025 & Are Endowment Funds in Trouble? · 20VC with Harry Stebbings
Apr 24, 2025
Disclosure
Lemkin: SaaStr Has Never Done Competitive Diligence Since First Investment
“I only did it once on my first investment in pipe drive and I give up. I've never done it. I've never reached out to a competitor. I've never done any competitive diligence, right? Not once.”
Jason Lemkin Apr 24, 2025 ▶ 1:16:14 How LP Deployment to Venture Will Change in 2025 & Are Endowment Funds in Trouble? · 20VC with Harry Stebbings
Apr 24, 2025
Assertion Not checkable as stated
Lemkin: Always knows if he wants to invest prior to meeting founders
“90, 90, I'll, every single time I've known I wanted to invest before the first meeting. A hundred percent.”
Jason Lemkin Apr 24, 2025 ▶ 1:22:28 How LP Deployment to Venture Will Change in 2025 & Are Endowment Funds in Trouble? · 20VC with Harry Stebbings
Apr 24, 2025
Insight
Lemkin: Private equity illiquidity causes far more strain for LPs than VC
“PE is the big problem. They're really the same thing. I mean, venture is a subset of PE, right? And the PE is so much bigger. And the fact that these deals are, did not go public in two to three years is the bigger stressor. Venture, venture, they don't love i…”
Jason Lemkin Apr 24, 2025 ▶ 42:21 How LP Deployment to Venture Will Change in 2025 & Are Endowment Funds in Trouble? · 20VC with Harry Stebbings
Apr 24, 2025
Insight
Lemkin: Venture capital is just a rounding error used to juice endowment returns
“Venture's a rounding error in most of most endowments, right? It's a subset, just like seed is a subset of venture. Venture's a subset of PE. It's not that important. It's just juice, right? It's just a way to juice your returns. P.E. Is where you put, deploy …”
Jason Lemkin Apr 24, 2025 ▶ 42:55 How LP Deployment to Venture Will Change in 2025 & Are Endowment Funds in Trouble? · 20VC with Harry Stebbings
Apr 24, 2025 negative
Assertion Not checkable as stated
Lemkin: LPs miscalculated distribution planning during prolonged tech liquidity drought
“One, everyone got their distribution planning wrong, their cash planning wrong. That's what happened in the industry. This is even pre Trump, pre everything. This is conversations I had late last year with LPs is we just, we, we're cool with our paper returns.…”
Jason Lemkin Apr 24, 2025 ▶ 41:48 How LP Deployment to Venture Will Change in 2025 & Are Endowment Funds in Trouble? · 20VC with Harry Stebbings
Apr 24, 2025
Insight
Lemkin: Investors Should Do Any Deal With 100% Conviction to 5x
“Any deal where you have a hundred percent conviction to Vivex, you should do it.”
Jason Lemkin Apr 24, 2025 ▶ 0:20 How LP Deployment to Venture Will Change in 2025 & Are Endowment Funds in Trouble? · 20VC with Harry Stebbings
Apr 24, 2025 neutral
Disclosure
Lemkin: Owner faces more competition than any company he has backed
“I don't think I've actually invested in a company with more competition than owner, not a single one. They direct competitors, adjacent competitors, virtually identical competitors.”
Jason Lemkin Apr 24, 2025 ▶ 1:23:48 How LP Deployment to Venture Will Change in 2025 & Are Endowment Funds in Trouble? · 20VC with Harry Stebbings
Apr 24, 2025 neutral
Assertion Supported
Lemkin: Cursor, Bolt, and Windsurf struggled for years before exploding
“I mean, I know Cursor almost died, right? Bolt almost died, right? And then finally it hit for Cursor. I don't know the whole story of Windsurf. Even Windsurf was Codium before it, right? It wasn't even the same, like everyone talks about Windsurf. 90 days ago…”
Jason Lemkin Apr 24, 2025 ▶ 18:53 How LP Deployment to Venture Will Change in 2025 & Are Endowment Funds in Trouble? · 20VC with Harry Stebbings
Apr 24, 2025 bullish
Prediction Not checkable as stated
Lemkin: Solely focused on finding one massive $8B+ outlier outcome
“At a business model, I'm only in it for one big massive win. That's it. Everything I'm going to do for the next, next years. It's just for a wizard better. I don't care about anything else from a business model. I don't care. So I'm going to do the best I can …”
Jason Lemkin Apr 24, 2025 ▶ 1:21:34 How LP Deployment to Venture Will Change in 2025 & Are Endowment Funds in Trouble? · 20VC with Harry Stebbings
Apr 24, 2025
Assertion Not checkable as stated
Lemkin generated a 10x return at prior VC firm before leaving
“When I worked for someone else's venture fund, I was told what my salary was. I mean, F you, I did 10 X in that fund and you're going to tell me what my salary is.”
Jason Lemkin Apr 24, 2025 ▶ 25:21 How LP Deployment to Venture Will Change in 2025 & Are Endowment Funds in Trouble? · 20VC with Harry Stebbings
Apr 24, 2025
Disclosure
Lemkin: All his billion-dollar exits were in competitive oligopolistic markets
“When I look at the billion dollar exits I've had, they're all in brutally competitive markets that were oligopical or similar.”
Jason Lemkin Apr 24, 2025 ▶ 1:03:54 How LP Deployment to Venture Will Change in 2025 & Are Endowment Funds in Trouble? · 20VC with Harry Stebbings
Apr 24, 2025 positive
Opinion
Lemkin: AI deal screening tool is better than a VC associate
“So now it's better than an associate. Honestly, it's better than an associate.”
Jason Lemkin Apr 24, 2025 ▶ 1:26:12 How LP Deployment to Venture Will Change in 2025 & Are Endowment Funds in Trouble? · 20VC with Harry Stebbings
Apr 24, 2025 neutral
Prediction Not checkable as stated
Lemkin will never invest in a startup without an S-tier CTO
“I no longer will give on CTO. We've talked about that in the past. That's when I will never give on again S tier CTO, or I'm off the, I'm off it”
Jason Lemkin Apr 24, 2025 ▶ 1:19:34 How LP Deployment to Venture Will Change in 2025 & Are Endowment Funds in Trouble? · 20VC with Harry Stebbings
Apr 24, 2025 negative
Insight
Lemkin: Founders uncertain of IPO should cap valuations at $100M
“I tell every founder to stop at a hundred million valuation. If you're not sure you're gonna IPO, now you may get it wrong, right? But if your gut says, I don't, IPO, man, 50% of five hundred million, that's not me, don't raise that north of a hundred.”
Jason Lemkin Apr 24, 2025 ▶ 51:02 How LP Deployment to Venture Will Change in 2025 & Are Endowment Funds in Trouble? · 20VC with Harry Stebbings
May 1, 2025 bullish
Opinion
Lemkin: Current AI boom is a bigger gold rush than 2021
“I think we can talk about liquidity and all this, but I honestly think that today is a much bigger gold rush than 20, 21 or other times we get like, I've never seen such a goal because this gold rush goes all the way down to high school kids.”
Jason Lemkin May 1, 2025 ▶ 5:25 What Does it Take to Be Good at Series A and B Today? · 20VC with Harry Stebbings
May 1, 2025 positive
Disclosure
Lemkin: 2017 fund performance stands at 4.31x return and 32.56% IRR
“I was looking at my 20 17 fund, and it is at, here, here's the question to, maybe especially to Rory, my virtual mentor here. It's at 4.31 X. With a 32.56 IRR, ok?”
Jason Lemkin May 1, 2025 ▶ 14:42 What Does it Take to Be Good at Series A and B Today? · 20VC with Harry Stebbings
May 1, 2025 bullish
Prediction Not checkable as stated
Lemkin: 1x venture fund returns are no longer worth the effort
“One X is not good enough for me anymore at this point in life. It's not worth it. I want three X the fund.”
Jason Lemkin May 1, 2025 ▶ 0:00 What Does it Take to Be Good at Series A and B Today? · 20VC with Harry Stebbings
May 8, 2025 positive
Insight
O'Driscoll: Doubling late-stage winners beats grinding early ARR growth
“That double from there. So, so much easier than grunting it out from a million to five million in ARR. Jason, because you did it as a CEO to ten million in ARR. Then the shitty year where you only go to 16. Then you re-accelerate a little. Oh my God. And now y…”
Rory O'Driscoll May 8, 2025 ▶ 10:16 Benchmark vs a16z: Why Stage Specific Firms Win · 20VC with Harry Stebbings
May 8, 2025 negative
Disclosure
Lemkin: Refuses meetings with seed-stage founders seeking $100M valuations
“Whenever I get an email from a founder that has what appears to be those metrics, right? That on their seed, they're going to get ten million at a hundred, right? 1015. I just email them back. I'm like, I can't compete. I don't take the meeting.”
Jason Lemkin May 8, 2025 ▶ 15:28 Benchmark vs a16z: Why Stage Specific Firms Win · 20VC with Harry Stebbings
May 8, 2025 bearish
Prediction Not checkable as stated
Lemkin: Hands-off tech middle managers will be eliminated within a year
“That in our industry, it's going to lead to massive human disruption. Just as many founders, just as many VCs, but man, if you're a hands-off keyboard middle manager, you're going to be gone in a year.”
Jason Lemkin May 8, 2025 ▶ 41:24 Benchmark vs a16z: Why Stage Specific Firms Win · 20VC with Harry Stebbings
May 8, 2025 neutral
Disclosure
Lemkin: SaaStr eliminated five jobs in 90 days due to AI
“Literally, we, even at Sastra, we've gotten rid of five people in our team in the last 90 days due to AI.”
Jason Lemkin May 8, 2025 ▶ 33:05 Benchmark vs a16z: Why Stage Specific Firms Win · 20VC with Harry Stebbings
May 8, 2025 bearish
Assertion Not checkable as stated
Lemkin: Virtually all growth-scale tech CEOs currently have hiring freezes
“Every CI CEO I know that's at growth scale has that isn't windsurf has some version of a hiring freeze going on, right? Even no matter unless the growth is insane and it's all you can hire, but you got to get rid of somebody, right? It's all AI first. And so i…”
Jason Lemkin May 8, 2025 ▶ 43:04 Benchmark vs a16z: Why Stage Specific Firms Win · 20VC with Harry Stebbings
May 15, 2025 positive
Insight
Lemkin: 99% of People Should Stay Liquid in VTI Rather Than VC
“I think 99% of folks should only be in liquid investments, including people in tech. You should be as liquid as possible. It's just too stressful for the, like VTI is the perfect product for 99% of people. It's the perfect product. You cannot beat it.”
Jason Lemkin May 15, 2025 ▶ 30:17 OpenAI, SBF & Perplexity: What VCs Know That You Don’t · 20VC with Harry Stebbings
May 15, 2025
Disclosure
Lemkin Admits He Only Works in the Office Two Days a Week
“To be honest, we have a beautiful office in Palo Alto. I only go two days a week, so I represent, acknowledge it's hypocritical.”
Jason Lemkin May 15, 2025 ▶ 43:27 OpenAI, SBF & Perplexity: What VCs Know That You Don’t · 20VC with Harry Stebbings
May 15, 2025 neutral
Assertion Partly supported
Lemkin: Gorgias AI Customer Support Automation Averages 20% Across 20,000 SMBs
“If you go into an app like gorgeous, where I'm on the board, where there's 20,000 customers using AI for SMB support, there's literally a slider and you can dial how much support AI you want from zero to a hundred. Okay. No matter what anybody says on X, And L…”
Jason Lemkin May 15, 2025 ▶ 33:46 OpenAI, SBF & Perplexity: What VCs Know That You Don’t · 20VC with Harry Stebbings
May 15, 2025 bullish
Prediction Not checkable as stated
Lemkin: A Top VC Firm Will Give Sam Bankman-Fried $100M
“I don't think Rory or I would, I'll defer to Rory, but I think someone will fund him. He's smart as Rory, Rory said, like he showed the upside as well as the downside. I don't know if there's a lot of morality in the business. I think someone will give them ju…”
Jason Lemkin May 15, 2025 ▶ 20:47 OpenAI, SBF & Perplexity: What VCs Know That You Don’t · 20VC with Harry Stebbings
May 22, 2025
Disclosure
Lemkin: Two portfolio companies recently received $500M acquisition offers
“I've had two portfolio companies recently that got offers to buy them at five hundred million. Okay, now in isolation, that sounds great, okay? But these are very good companies, okay? This is not open AI. These are very good companies. One was just a smidge a…”
Jason Lemkin May 22, 2025 ▶ 23:44 Rippling vs. Deel Lawsuit: WTF Happens Now? The Future of the Late Stage Private Market · 20VC with Harry Stebbings
May 22, 2025 neutral
Assertion Not checkable as stated
Lemkin: Tech executives are eager to replace bottom 30% of headcount with AI
“The basic vibe was everyone recognized 20 to 30% of their team's gonna be replaced with AI, and they're happy for it.”
Jason Lemkin May 22, 2025 ▶ 1:03:19 Rippling vs. Deel Lawsuit: WTF Happens Now? The Future of the Late Stage Private Market · 20VC with Harry Stebbings
May 22, 2025
Insight
Lemkin: Seed investors should sell at $2B valuation unless 100% certain
“When I was looking at this on a spreadsheet, my new role is at two billion, sell unless you're a hundred percent sure you shouldn't as a seed manager at two billion.”
Jason Lemkin May 22, 2025 ▶ 37:32 Rippling vs. Deel Lawsuit: WTF Happens Now? The Future of the Late Stage Private Market · 20VC with Harry Stebbings
May 22, 2025 positive
Assertion Supported
Lemkin: Otter.ai has crossed $100 million in revenue
“Otter AI just announced across a hundred million in revenue, right?”
Jason Lemkin May 22, 2025 ▶ 1:08:21 Rippling vs. Deel Lawsuit: WTF Happens Now? The Future of the Late Stage Private Market · 20VC with Harry Stebbings
May 22, 2025 neutral
Disclosure
Lemkin: I no longer read seed deal documents and just sign them
“But I'm not grumpy about it anymore. I just signed the documents. I don't even read them anymore. Cause it don't matter what's in them. I just sign them, and it doesn't matter what I think.”
Jason Lemkin May 22, 2025 ▶ 13:30 Rippling vs. Deel Lawsuit: WTF Happens Now? The Future of the Late Stage Private Market · 20VC with Harry Stebbings
May 29, 2025 negative
Assertion Supported
Lemkin: OpenAI has a 67% two-year employee retention rate
“67% retention rate employees after two years.”
Jason Lemkin May 29, 2025 ▶ 13:48 OpenAI’s $6BN Jony Ive Deal & YC Is Both Chanel and Walmart, and Has Officially Won! · 20VC with Harry Stebbings
May 29, 2025 bullish
Prediction Not checkable as stated
Lemkin: AI will feel like AGI by 2026, expert consensus by 2028
“What I think is it will feel like AGI in twenty-twenty-six, and the really smart guys will agree we're there around twenty-twenty-eight.”
Jason Lemkin May 29, 2025 ▶ 1:09:26 OpenAI’s $6BN Jony Ive Deal & YC Is Both Chanel and Walmart, and Has Officially Won! · 20VC with Harry Stebbings
May 29, 2025 bearish
Prediction Not checkable as stated
Lemkin predicts mass tech layoffs within 24 months despite flat headcount
“I think we're going to see mass layoffs in the next 24 months, but I don't think the net headcount is, I think the net headcount is going to stay flat, right?”
Jason Lemkin May 29, 2025 ▶ 1:04:32 OpenAI’s $6BN Jony Ive Deal & YC Is Both Chanel and Walmart, and Has Officially Won! · 20VC with Harry Stebbings
May 29, 2025
Disclosure
Lemkin: I have not had a billion-dollar portfolio exit since 2021
“I haven't had a billion dollar exit since 2021. It may be quite a while until I have one.”
Jason Lemkin May 29, 2025 ▶ 38:27 OpenAI’s $6BN Jony Ive Deal & YC Is Both Chanel and Walmart, and Has Officially Won! · 20VC with Harry Stebbings
May 29, 2025 positive
Insight
Lemkin: The constant feeling of failure in San Francisco drives success
“That's the special part of the, of being an SF. You feel like you're failing every day compared to everybody around.”
Jason Lemkin May 29, 2025 ▶ 59:09 OpenAI’s $6BN Jony Ive Deal & YC Is Both Chanel and Walmart, and Has Officially Won! · 20VC with Harry Stebbings
Jun 5, 2025 negative
Disclosure
Lemkin: Ownership in YC Companies Is Less Than Half Normal Target
“All I can tell you, my little analysis of YC is I've ended up owning about a little less than half of what I would have.”
Jason Lemkin Jun 5, 2025 ▶ 1:11:14 Is DPI The Only Thing That Matters? with Sam Lessin, Jason Lemkin & Rory O’Driscoll · 20VC with Harry Stebbings
Jun 5, 2025 bullish
Prediction Partly held up
Lemkin: Menlo Ventures will 10x to 15x its investment in Chime
“They said they did the Series B, right? So they did the Series B at 203 hundred. Maybe we can figure it out on the fly. They're going to, this will be a nine. There'll be some dilution. They'll 10 or 15 X their money, right? That'll be a fun returner or more t…”
Jason Lemkin Jun 5, 2025 ▶ 23:36 Is DPI The Only Thing That Matters? with Sam Lessin, Jason Lemkin & Rory O’Driscoll · 20VC with Harry Stebbings
Jun 5, 2025 neutral
Prediction Not checkable as stated
Lemkin: The next generation will not use files or traditional software interfaces
“I think what I do know is that this generation will not use the Internet remotely like we do. They will not use lead contacts and opportunities. They will not use files. Files are disappearing overnight. Kids do not know what a file is. It does not matter. And…”
Jason Lemkin Jun 5, 2025 ▶ 55:20 Is DPI The Only Thing That Matters? with Sam Lessin, Jason Lemkin & Rory O’Driscoll · 20VC with Harry Stebbings
Jun 5, 2025 neutral
Opinion
Lemkin: Modern Series A rounds are $20M to $30M
“Every founder wants to raise 20 or thirty million in their A now. No one wants to raise an eight, the eight million dollar series A is now three safe notes, right?”
Jason Lemkin Jun 5, 2025 ▶ 10:54 Is DPI The Only Thing That Matters? with Sam Lessin, Jason Lemkin & Rory O’Driscoll · 20VC with Harry Stebbings
Jun 5, 2025 bearish
Opinion
Lemkin: Model Context Protocol is an existential threat to SaaS applications
“I think that it's early, but it's, I think MCP is an existential threat to almost every SaaS app.”
Jason Lemkin Jun 5, 2025 ▶ 58:05 Is DPI The Only Thing That Matters? with Sam Lessin, Jason Lemkin & Rory O’Driscoll · 20VC with Harry Stebbings
Jun 5, 2025 positive
Assertion Partly supported
Jason Lemkin: Thoma Bravo raised $35B fund for B2B acquisitions
“I know we glossed over it in the beginning, but I do think Tom O'Bravo raising a record fund this week is a good sign too. That's thirty-five billion dollars to buy B to B companies, almost entirely B to B, right?”
Jason Lemkin Jun 5, 2025 ▶ 1:16:56 Is DPI The Only Thing That Matters? with Sam Lessin, Jason Lemkin & Rory O’Driscoll · 20VC with Harry Stebbings
Jun 12, 2025 negative
Assertion Not checkable as stated
Lemkin: AI spending is actively cannibalizing legacy SaaS budgets
“If cursor did almost half a million, half a billion dollars in revenue in the same time, It sucked up an enormous amount of that dollar that would have gone to Okta and Salesforce, right? Five hundred million. That's a lot in that period of time, right? So AI …”
Jason Lemkin Jun 12, 2025 ▶ 49:50 Elon’s Empire: SpaceX, Tesla, Neuralink After the Storm & Anduril’s $2.6BN Power Move · 20VC with Harry Stebbings
Jun 12, 2025
Insight
Jason Lemkin: Big venture returns require TAM explosions for top players
“I think the venture lesson, be visionary, but relentlessly honest about TAM. Because it's a TAM story at the end of the day. If you have a number one or number two player in the space and you see a TAM explosion happening, that's where you get a big lift, righ…”
Jason Lemkin Jun 12, 2025 ▶ 39:34 Elon’s Empire: SpaceX, Tesla, Neuralink After the Storm & Anduril’s $2.6BN Power Move · 20VC with Harry Stebbings
Jun 12, 2025 neutral
Prediction Not checkable as stated
Lemkin: Public outrage over Elon Musk's politics will fade within a year
“I think in a year we will not have forgotten about it, but maybe no one cares.”
Jason Lemkin Jun 12, 2025 ▶ 1:07:23 Elon’s Empire: SpaceX, Tesla, Neuralink After the Storm & Anduril’s $2.6BN Power Move · 20VC with Harry Stebbings
Jun 12, 2025 positive
Disclosure
Lemkin: Invested in Pipedrive at a $16M Valuation
“When I did that bet in pipe drive, ok? And that was, and I, Did it at sixteen million, right?”
Jason Lemkin Jun 12, 2025 ▶ 44:33 Elon’s Empire: SpaceX, Tesla, Neuralink After the Storm & Anduril’s $2.6BN Power Move · 20VC with Harry Stebbings
Jun 12, 2025 negative
Assertion Not checkable as stated
Lemkin: Private secondary liquidity instantly vanishes when company growth slows
“I think if your growth struggles, it's, it instantly evaporates.”
Jason Lemkin Jun 12, 2025 ▶ 24:04 Elon’s Empire: SpaceX, Tesla, Neuralink After the Storm & Anduril’s $2.6BN Power Move · 20VC with Harry Stebbings
Jun 12, 2025
Insight
Lemkin: 10x IPO oversubscription is not enough for a strong stock pop
“In my limited experience, like 10 X actually isn't enough because those are soft commitments and people put in over allocations to make sure they can get it, and you really want to be like, 30 X oversubscribed to pop hard, which I don't know if that's your, wh…”
Jason Lemkin Jun 12, 2025 ▶ 7:22 Elon’s Empire: SpaceX, Tesla, Neuralink After the Storm & Anduril’s $2.6BN Power Move · 20VC with Harry Stebbings
Jun 12, 2025 bullish
Opinion
Lemkin: Tech talent should only join late-stage startups with tender offers
“If I was a top tier engineer or almost any, anyone that wanted to kind of have the comfort of a later stage company, I might only join someone with a perfected tender offer program. I mean, I wouldn't even bother for anything else.”
Jason Lemkin Jun 12, 2025 ▶ 24:10 Elon’s Empire: SpaceX, Tesla, Neuralink After the Storm & Anduril’s $2.6BN Power Move · 20VC with Harry Stebbings
Jun 12, 2025 positive
What-if
Lemkin: VCs should fund every round up to $1B valuation in top seed winners
“What I personally would do would be to do every dollar up to a billion. That would be my version of it. In every winner. Ah, so if you do a seed investment and it turns out to be a winner, right? A top five percent deal, you do every round, A, B, C, D, E, unti…”
Jason Lemkin Jun 12, 2025 ▶ 34:06 Elon’s Empire: SpaceX, Tesla, Neuralink After the Storm & Anduril’s $2.6BN Power Move · 20VC with Harry Stebbings
Jun 12, 2025 neutral
Assertion Not checkable as stated
Lemkin: Deep-pocketed VCs are oversubscribing rounds to monopolize follow-on allocation
“Currently in like in my little portfolio, the two hottest companies, and I put hot in quotes, That's what investors on the cap table with access to unlimited capital are based, like, wildly oversubscribed because they're trying to just put every single dollar …”
Jason Lemkin Jun 12, 2025 ▶ 34:39 Elon’s Empire: SpaceX, Tesla, Neuralink After the Storm & Anduril’s $2.6BN Power Move · 20VC with Harry Stebbings
Jun 12, 2025
Disclosure
Lemkin discloses earning $3,000-$4,000 monthly from X/Twitter creator payouts
“I get like three or four grand from Twitter a month.”
Jason Lemkin Jun 12, 2025 ▶ 1:19:43 Elon’s Empire: SpaceX, Tesla, Neuralink After the Storm & Anduril’s $2.6BN Power Move · 20VC with Harry Stebbings
Jun 19, 2025
Insight
Lemkin: Investors should challenge founders to sell to test their conviction
“I tell all founders to sell now, by the way. I just, I, only as a challenge. I'm not saying you shouldn't take this fake offer, but this is my, this is what I, my life lesson. I tell you to take it. And then if you come back the next day and say what you just …”
Jason Lemkin Jun 19, 2025 ▶ 13:44 Chime IPO: Are IPOs Hotter Than Ever? · 20VC with Harry Stebbings
Jun 19, 2025 negative
Opinion
Lemkin: Dismissing Chinese AI progress stems from Bay Area hubris
“This is a Bay Area, there's a lot of Bay Area hubris and this is one of them. We can't access, they can't access our internet. It's a different world out over there. But man, the power when everyone's aligned.”
Jason Lemkin Jun 19, 2025 ▶ 1:07:15 Chime IPO: Are IPOs Hotter Than Ever? · 20VC with Harry Stebbings
Jun 19, 2025 bullish
Disclosure
Lemkin: Personal financial position is 100% allocated to equities
“No, I'm back where I was in 2008, a hundred percent equity in my personal position, a hundred percent.”
Jason Lemkin Jun 19, 2025 ▶ 1:05:36 Chime IPO: Are IPOs Hotter Than Ever? · 20VC with Harry Stebbings
Jun 19, 2025 bullish
Assertion Supported
Lemkin: Databricks recently held an analyst summit and is IPO-ready
“Literally the fact that this last week they had an analyst summit where they went through all their metrics, their revenue, their growth rate through through an entire group of investors and analysts says to me, they will decide one data file and it will just …”
Jason Lemkin Jun 19, 2025 ▶ 49:30 Chime IPO: Are IPOs Hotter Than Ever? · 20VC with Harry Stebbings
Jun 26, 2025 bullish
Assertion Partly supported
Lemkin: Tech IPO volume is up 62.5% this year
“IPOs by number are up 62 and a half percent this year, apparently, based on data I saw today, right?”
Jason Lemkin Jun 26, 2025 ▶ 36:07 Navan Files to Go Public and Canva Pulls the Brakes: Why and What Happens? · 20VC with Harry Stebbings
Jun 26, 2025 bearish
Prediction Held up
Lemkin: Trump Mobile smartphone will not release before September 2025
“It's impossible. There's no supply chain evidence of any phone in production. There haven't been any leaks of an actual phone in production. And there haven't been any leaks to sites of true product development other than a mock-up of a golden phone.”
Jason Lemkin Jun 26, 2025 ▶ 1:13:07 Navan Files to Go Public and Canva Pulls the Brakes: Why and What Happens? · 20VC with Harry Stebbings
Jun 26, 2025 neutral
What-if
Lemkin: Harvey was indistinguishable from 11 other AI wrappers at seed
“If I'd met Harvey at the seed stage, I would have said this is great, but I don't know that I could have told the difference from the 11 other ones that were doing this amazingly as essentially, I hate the term, but as wrappers.”
Jason Lemkin Jun 26, 2025 ▶ 18:27 Navan Files to Go Public and Canva Pulls the Brakes: Why and What Happens? · 20VC with Harry Stebbings
Jun 26, 2025 bullish
Prediction Not checkable as stated
Lemkin: Every tech startup with strong metrics will IPO within 12 months
“Anyone that's got the numbers is gonna go public, right? In the next 12 months, they're all gonna go public.”
Jason Lemkin Jun 26, 2025 ▶ 36:35 Navan Files to Go Public and Canva Pulls the Brakes: Why and What Happens? · 20VC with Harry Stebbings
Jul 3, 2025 positive
Disclosure
Lemkin: Bailed out a struggling startup now generating over $300M ARR
“I remember a founder I had to completely bail out from fumes with more money than I had and that company's doing over three hundred million today.”
Jason Lemkin Jul 3, 2025 ▶ 18:28 Figma’s IPO: The Full Breakdown & Why Melio’s $2.5BN Acquisition is “Discouraging” · 20VC with Harry Stebbings
Jul 3, 2025 negative
Assertion Not checkable as stated
Lemkin: Founders buying Atherton mansions correlates almost 100% with revenue decline
“The massive patent Atherton is like almost a hundred percent correlation to decline in revenue. It's like, it's almost a one-to-one, I can't prove causation, but I can prove correlation almost one-to-one.”
Jason Lemkin Jul 3, 2025 ▶ 36:12 Figma’s IPO: The Full Breakdown & Why Melio’s $2.5BN Acquisition is “Discouraging” · 20VC with Harry Stebbings
Jul 3, 2025 bearish
Disclosure
Lemkin: Portfolio companies in PE acquisition range receive zero PE inbound
“This is such a small number, it's barely useful, other than anecdotally, but I have two portfolio companies That are kind of in that intersection where, where a tech company and a PE buyer might buy them. Right. And they both got mediocre M&A offers recently. …”
Jason Lemkin Jul 3, 2025 ▶ 45:50 Figma’s IPO: The Full Breakdown & Why Melio’s $2.5BN Acquisition is “Discouraging” · 20VC with Harry Stebbings
Jul 3, 2025 negative
Assertion Not checkable as stated
Lemkin: Public CEOs Privately Expect AI to Cut Half Their Staff
“That's what every CEO talks about behind closed doors of a public company. I, they say, I don't know, I need to reskill 20 to 30% of my people, but they really think I might not even need half.”
Jason Lemkin Jul 3, 2025 ▶ 1:07:28 Figma’s IPO: The Full Breakdown & Why Melio’s $2.5BN Acquisition is “Discouraging” · 20VC with Harry Stebbings
Jul 3, 2025 negative
Insight
Lemkin: Startups failing to grow through AI have already failed
“My rule is if you haven't grown because of AI, you've failed.”
Jason Lemkin Jul 3, 2025 ▶ 0:00 Figma’s IPO: The Full Breakdown & Why Melio’s $2.5BN Acquisition is “Discouraging” · 20VC with Harry Stebbings
Jul 3, 2025 bearish
Opinion
Lemkin: Melio's $2.5B acquisition multiple is intimidating for venture expectations
“I thought it was discouraging. What I mean is that Melio gets acquired for 2.5 billion... This is not the greatest multiple of all time, is it? That that that intimidates me that it's not a great multiple. I find it intimidating as an investor, actually, becau…”
Jason Lemkin Jul 3, 2025 ▶ 24:47 Figma’s IPO: The Full Breakdown & Why Melio’s $2.5BN Acquisition is “Discouraging” · 20VC with Harry Stebbings
Jul 3, 2025 neutral
Assertion Supported
Lemkin: 50% of Unicorn Capital Goes to $5B+ Companies
“Crunchbase did an article this week. There's no such thing as unicorns anymore, because forget about AI. Only the money goes to five billion and up. It's got to be five billion corns. Like, 50% of all the unicorn money is north of five billion.”
Jason Lemkin Jul 3, 2025 ▶ 1:06:51 Figma’s IPO: The Full Breakdown & Why Melio’s $2.5BN Acquisition is “Discouraging” · 20VC with Harry Stebbings
Jul 10, 2025
Disclosure
Lemkin: Stacking trusts shields up to $50M per exit from federal taxes
“And frankly, you can stack it with trusts, like for me, it's probably 40 to fifty million per, because I have five trusts on this, so that means for each exit I get, fifty million has no taxes.”
Jason Lemkin Jul 10, 2025 ▶ 52:23 Daniel Gross and Nat Friedman: Acquired by Meta | Microsoft Layoff 9000 People | OpenAI's Bombshell · 20VC with Harry Stebbings
Jul 10, 2025 bearish
Prediction Not checkable as stated
Lemkin: AI will replace 30% to 40% of short-cycle sales reps
“My rough sense is it's 30 to 40% of, like, one to two call sales reps are gonna be replaced by AI. It won't be the same as with support, but it'll approach it. It'll be relatively small in the enterprise, ok?”
Jason Lemkin Jul 10, 2025 ▶ 53:35 Daniel Gross and Nat Friedman: Acquired by Meta | Microsoft Layoff 9000 People | OpenAI's Bombshell · 20VC with Harry Stebbings
Jul 10, 2025 negative
Insight
Lemkin: Corporate employee re-skilling programs do not work
“I think re-skilling doesn't work, and I think Canva's basically saying, shit or get off the can, guys.”
Jason Lemkin Jul 10, 2025 ▶ 55:46 Daniel Gross and Nat Friedman: Acquired by Meta | Microsoft Layoff 9000 People | OpenAI's Bombshell · 20VC with Harry Stebbings
Jul 10, 2025
Insight
Lemkin: Unprofitable high-multiple public companies must aggressively buy assets with stock
“If you have a public company trading at a crazy high, high multiple, right? 20 X revenues that has existential losses. You got to use your stock as your currency ASAP. You gotta buy everything you can that can address the bottom line or other challenges you ha…”
Jason Lemkin Jul 10, 2025 ▶ 26:42 Daniel Gross and Nat Friedman: Acquired by Meta | Microsoft Layoff 9000 People | OpenAI's Bombshell · 20VC with Harry Stebbings
Jul 10, 2025 positive
Assertion Supported
Lemkin: Circle generated $156 million in net income last year
“Circle had net income of a hundred and fifty six million last year.”
Jason Lemkin Jul 10, 2025 ▶ 28:33 Daniel Gross and Nat Friedman: Acquired by Meta | Microsoft Layoff 9000 People | OpenAI's Bombshell · 20VC with Harry Stebbings
Jul 10, 2025 bullish
Disclosure
Lemkin: QSBS tax exemption is key motivator for early-stage investing
“For me, this is my quiet motivator to do early stage investing. At least I can avoid, you know, fifteen million of taxes per deal.”
Jason Lemkin Jul 10, 2025 ▶ 52:55 Daniel Gross and Nat Friedman: Acquired by Meta | Microsoft Layoff 9000 People | OpenAI's Bombshell · 20VC with Harry Stebbings
Jul 10, 2025 bearish
Opinion
Lemkin: Retail investors should not have exposure to private assets
“To Terry's point, if Vanguard has 10 trillion, putting 10% of that into venture would move the needle, but I just don't think ordinary investors should be doing this stuff. I don't know. There's just I just, I, it's just part of greed. Too much greed.”
Jason Lemkin Jul 10, 2025 ▶ 46:59 Daniel Gross and Nat Friedman: Acquired by Meta | Microsoft Layoff 9000 People | OpenAI's Bombshell · 20VC with Harry Stebbings
Jul 17, 2025 negative
Disclosure
Lemkin spent $600 in six days attempting to vibe code an app
“If I've already burned 600 dollars in credits in six days, ok, to get 10% of the way there. So you can't do it for 20 bucks a month, ok?”
Jason Lemkin Jul 17, 2025 ▶ 36:15 Windsurf x Google x Cognition: Full Breakdown: Who Made Money, Who Did Not · 20VC with Harry Stebbings
Jul 17, 2025 neutral
Prediction Not checkable as stated
Lemkin: $3.5B AI deals won't make top news within 24 months
“Three and a half billion may not mean anything in the next 24 months in AI. Like it may not make the above the fold news in AI.”
Jason Lemkin Jul 17, 2025 ▶ 1:15:04 Windsurf x Google x Cognition: Full Breakdown: Who Made Money, Who Did Not · 20VC with Harry Stebbings
Jul 17, 2025 negative
Opinion
Lemkin calls 'roll your own' SaaS trend dumbest in his career
“The idea that the roll your own initiative, I think is the dumbest thing I've seen in SAS in my career.”
Jason Lemkin Jul 17, 2025 ▶ 35:38 Windsurf x Google x Cognition: Full Breakdown: Who Made Money, Who Did Not · 20VC with Harry Stebbings
Jul 17, 2025 negative
Opinion
Lemkin: Tech publication The Information is no longer important or meaningful
“It's, this is, I mean, it had its moment, Harry, but it's not one of the important companies today. It's not a meaningful company.”
Jason Lemkin Jul 17, 2025 ▶ 1:16:09 Windsurf x Google x Cognition: Full Breakdown: Who Made Money, Who Did Not · 20VC with Harry Stebbings
Jul 17, 2025 bullish
Assertion Supported
Lemkin: RevenueCat powers 40% of mobile subscription apps
“On Revenue Cat or Harry and I Investors, they power 40% of mobile subscription apps. I think the average app across all mobile paid apps is like six percent a month churn.”
Jason Lemkin Jul 17, 2025 ▶ 50:11 Windsurf x Google x Cognition: Full Breakdown: Who Made Money, Who Did Not · 20VC with Harry Stebbings
Jul 17, 2025 bearish
Opinion
Lemkin: Windsurf was hopeless before recent deal
“Windsurf was hopeless before this deal.”
Jason Lemkin Jul 17, 2025 ▶ 22:25 Windsurf x Google x Cognition: Full Breakdown: Who Made Money, Who Did Not · 20VC with Harry Stebbings
Jul 17, 2025 negative
Opinion
Lemkin: Anthropic and OpenAI face harsher safety backlash than Elon Musk
“Elon Musk can get away with this the most. Just because of who he is. Like, it's unacceptable to have a race, to release a racist model to the, like, there's, this is as unacceptable as it gets. But Sam Altman's going to be fried. Anthropic's going to be fried…”
Jason Lemkin Jul 17, 2025 ▶ 34:39 Windsurf x Google x Cognition: Full Breakdown: Who Made Money, Who Did Not · 20VC with Harry Stebbings
Jul 17, 2025 bullish
Opinion
Lemkin: Vibe coding TAM is 50x to 100x bigger than developer tools
“The TAM really is much bigger than cursor. It's much bigger than cursor or windsurf. It could be like 50 or a hundred times bigger.”
Jason Lemkin Jul 17, 2025 ▶ 39:13 Windsurf x Google x Cognition: Full Breakdown: Who Made Money, Who Did Not · 20VC with Harry Stebbings
Jul 24, 2025
Disclosure
Lemkin: VCs now meet fund-returning founders once a quarter at best
“When I started, I met everybody in the industry cause it was small, right? So it was once a month. Now I would say I'm lucky if it's once a quarter to your point, right?”
Jason Lemkin Jul 24, 2025 ▶ 56:38 How Do All Providers Deal with Anthropic Dependency Risk & Figma IPO Breakdown: Where Does it Price? · 20VC with Harry Stebbings
Jul 24, 2025 neutral
Disclosure
Lemkin: One seed investment spawned two $100M+ venture funds
“I have one investment that has not IPO'd, ok? That is only, I would say, reasonably hot, but very good, ok? It is our, that investment, where I was a seed, has already spawned two nine-figure funds out of it. Two.”
Jason Lemkin Jul 24, 2025 ▶ 1:15:10 How Do All Providers Deal with Anthropic Dependency Risk & Figma IPO Breakdown: Where Does it Price? · 20VC with Harry Stebbings
Jul 24, 2025 negative
Opinion
Jason Lemkin: Fund managers who return no capital deserve no sympathy
“This idea that, oh, woe is me. I can't raise a third fund. I've never returned any capital. Tough luck, right?”
Jason Lemkin Jul 24, 2025 ▶ 0:00 How Do All Providers Deal with Anthropic Dependency Risk & Figma IPO Breakdown: Where Does it Price? · 20VC with Harry Stebbings
Jul 24, 2025 neutral
Disclosure
Lemkin caps seed entry valuations at $30 million max
“Even if you beat Andreessen, and Andreessen's offering 50, and you say, listen, the best I can do is 30, and I've done this multiple times, because 30 is the highest price I pay. It is, it's on my website, so there's multiple deals I've done where the price ha…”
Jason Lemkin Jul 24, 2025 ▶ 46:25 How Do All Providers Deal with Anthropic Dependency Risk & Figma IPO Breakdown: Where Does it Price? · 20VC with Harry Stebbings
Jul 31, 2025
Insight
Lemkin: Mature public tech companies are trapped by high margin expectations
“It is almost impossible for most public companies to actually spend the cash there they're generating. So Zuck's got a triple down here because he's getting also a hall pass. The market's saying it's okay to spend everything, right?”
Jason Lemkin Jul 31, 2025 ▶ 1:03:03 Why Apple Needs a Management Overhaul & Why Google is Catching Up with Hyperscalers · 20VC with Harry Stebbings
Aug 7, 2025 bearish
Prediction Not checkable as stated
Lemkin: VCs Will Not Waive Unearned Stock Compensation Triggers
“I'll bet you nickels to dollars that doesn't happen because founders are just signing up. I don't know what Brian you see at Sequoia, but founders are signing up for crazy stuff these days. They're signing up for massive stuff. And I don't think a lot of grouc…”
Jason Lemkin Aug 7, 2025 ▶ 32:33 Figma's 250% Pop - The Greatest IPO Mispricing Ever? Meta & Microsoft Blowout Quarters: Broken Down · 20VC with Harry Stebbings
Aug 7, 2025 negative
Disclosure
Lemkin: Opportunity funds were not worth the extra effort for 15% returns
“Wasn't worth it For me to do the opportunity funds. It's not enough. Like I'll make like 15% more money. It's not enough money, right?”
Jason Lemkin Aug 7, 2025 ▶ 1:21:06 Figma's 250% Pop - The Greatest IPO Mispricing Ever? Meta & Microsoft Blowout Quarters: Broken Down · 20VC with Harry Stebbings
Aug 7, 2025 positive
Insight
Lemkin: VCs should size funds smaller to enter carry mode faster
“Normal times you want to optimize your fund size to achieve the maximum carry you can in a given time, right? And then just go raise another, right? In an ideal world, you might even raise the fund a year, right? So you can get into carry mode as quickly as po…”
Jason Lemkin Aug 7, 2025 ▶ 1:20:43 Figma's 250% Pop - The Greatest IPO Mispricing Ever? Meta & Microsoft Blowout Quarters: Broken Down · 20VC with Harry Stebbings
Aug 14, 2025 positive
Disclosure
Lemkin: Two portfolio companies use AI software engineer Devin
“Two of my portfolio companies use Devin, like their AI tool, and they love it for niche use cases, but we never talk about it.”
Jason Lemkin Aug 14, 2025 ▶ 22:02 Sam Altman's Masterplan or a Gift to Anthropic? Palantir & Shopify Crush Earnings · 20VC with Harry Stebbings
Aug 14, 2025 bullish
Prediction Not checkable as stated
Lemkin: SaaStr Will Generate $20 Million in Revenue With Two Employees
“If we're lucky, Saster Inc. Will do twenty million this calendar year with two people. Two people, and depending on how you count them, like two, two, two employees.”
Jason Lemkin Aug 14, 2025 ▶ 1:24:09 Sam Altman's Masterplan or a Gift to Anthropic? Palantir & Shopify Crush Earnings · 20VC with Harry Stebbings
Aug 14, 2025 bullish
Prediction Held up
Lemkin: AI will enable 20-to-40-person teams to build billion-dollar companies
“If you allow for some outsourcing agencies resources that come and go, I think we will see a bunch of 20, 30, 40 person, billion dollar companies because a core of engineers, a bunch of AIs making, and people are going to be like, you know what, dude, not, I d…”
Jason Lemkin Aug 14, 2025 ▶ 1:22:03 Sam Altman's Masterplan or a Gift to Anthropic? Palantir & Shopify Crush Earnings · 20VC with Harry Stebbings
Aug 14, 2025 bearish
Disclosure
Lemkin: Success Rate Placing Veteran B2B Executives Dropped to 10%
“Listen, until maybe 18 months ago, if any seasoned B to B executive that I knew needed a job, ok, that I knew reasonably well, I'd get him a job by an email. I could reach out to someone, not even in my portfolio, extended network founders I met that I knew me…”
Jason Lemkin Aug 14, 2025 ▶ 1:06:38 Sam Altman's Masterplan or a Gift to Anthropic? Palantir & Shopify Crush Earnings · 20VC with Harry Stebbings
Aug 21, 2025 negative
Opinion
Lemkin: SPACs are at the edge of grift
“Why, why not do something more meaningful with the world rather than do something like a SPAC, which is at the edge of grift?”
Jason Lemkin Aug 21, 2025 ▶ 23:08 Databricks at $100BN, CoreWeave’s $11B Debt Bet & Nubank’s $2.5B Profit Shocker - Ep.19 · 20VC with Harry Stebbings
Aug 21, 2025 neutral
Disclosure
Lemkin: SaaStr spends $500K in list price on 10 AI tools
“We added up the nominal list price of our 10 tools, right? 500,000 dollars.”
Jason Lemkin Aug 21, 2025 ▶ 1:15:24 Databricks at $100BN, CoreWeave’s $11B Debt Bet & Nubank’s $2.5B Profit Shocker - Ep.19 · 20VC with Harry Stebbings
Aug 21, 2025 bearish
Prediction Not checkable as stated
Lemkin: Buyers will demand AI software from single vendors within 12 months
“We're already seeing this consolidation in e-commerce if we want to chat about where they're becoming one tool already. I think it's a real risk for all these cool ones. Like we just don't need five of them going to Rory's point. We may, Rippling's a good exam…”
Jason Lemkin Aug 21, 2025 ▶ 1:17:26 Databricks at $100BN, CoreWeave’s $11B Debt Bet & Nubank’s $2.5B Profit Shocker - Ep.19 · 20VC with Harry Stebbings
Aug 21, 2025
Assertion Not checkable as stated
Lemkin: Hot venture capital deals are now exclusively done on Saturdays
“And it's a cost of doing deals over the, I find all hot deals now are done on Saturdays. They're all, this is the new founder vibe.”
Jason Lemkin Aug 21, 2025 ▶ 36:40 Databricks at $100BN, CoreWeave’s $11B Debt Bet & Nubank’s $2.5B Profit Shocker - Ep.19 · 20VC with Harry Stebbings
Aug 21, 2025
Prediction Not checkable as stated
Lemkin: Current tech era will see 20+ nine-figure founder cash-outs
“But it makes sense there should be double digits in this era, right? There should be 10, 20 founders who walk away with nine figures whether they're WeWorks or Hoppins, there's gotta be 20 or more of them.”
Jason Lemkin Aug 21, 2025 ▶ 36:27 Databricks at $100BN, CoreWeave’s $11B Debt Bet & Nubank’s $2.5B Profit Shocker - Ep.19 · 20VC with Harry Stebbings
Aug 21, 2025 positive
Disclosure
Lemkin: SaaStr replaced five human employees with 10 AI agents
“We have 10 AI agents at our little team that have replaced five humans and it's going to go up.”
Jason Lemkin Aug 21, 2025 ▶ 1:13:04 Databricks at $100BN, CoreWeave’s $11B Debt Bet & Nubank’s $2.5B Profit Shocker - Ep.19 · 20VC with Harry Stebbings
Aug 28, 2025 neutral
Prediction Not checkable as stated
Lemkin: Salesforce will redeploy 70% of SDR headcount into higher-value roles
“I think we'll redeploy. He'll, I think Salesforce, I don't know how many like entry-level SDR Salesforce has, but I bet you redeploy 70% of that headcount into enterprise reps or forward deployed engineers. That headcount just becomes more valued with agent fo…”
Jason Lemkin Aug 28, 2025 ▶ 22:40 Anthropic's $10B Round, Klarna's IPO, Inside a16z's 72 Deal Seed Investment Machine ft. Marc Benioff · 20VC with Harry Stebbings
Aug 28, 2025 negative
Assertion Partly supported
Lemkin: Top 10 deals consume 40% of venture capital
“You know, the 10 deals are consuming 40% of venture capital.”
Jason Lemkin Aug 28, 2025 ▶ 1:04:56 Anthropic's $10B Round, Klarna's IPO, Inside a16z's 72 Deal Seed Investment Machine ft. Marc Benioff · 20VC with Harry Stebbings
Sep 11, 2025
Opinion
Lemkin: Jailing Fraudulent Founders Is the Best Startup Governance Control
“I think the best control today would be if more founders that committed fraud went to jail. I just think if every month someone went to jail that completely lied, I know Roy disagrees, completely lied in a round, sent financials where they aggregated all their…”
Jason Lemkin Sep 11, 2025 ▶ 1:27:13 OpenAI’s $10BN Secondary Sale, Ramp Hits $1BN ARR & Brex Hits $700M · 20VC with Harry Stebbings
Sep 11, 2025 neutral
Disclosure
Lemkin: Founders Control the Board in Almost All Portfolio Companies
“Almost all my portfolio companies, the founders control the board, not just from a cap table perspective, but from a relationship perspective, they control it.”
Jason Lemkin Sep 11, 2025 ▶ 6:17 OpenAI’s $10BN Secondary Sale, Ramp Hits $1BN ARR & Brex Hits $700M · 20VC with Harry Stebbings
Sep 11, 2025 bearish
Prediction Held up
Lemkin: Canva has zero percent chance of Q4 IPO
“No, no. Zero percent.”
Jason Lemkin Sep 11, 2025 ▶ 1:25:10 OpenAI’s $10BN Secondary Sale, Ramp Hits $1BN ARR & Brex Hits $700M · 20VC with Harry Stebbings
Sep 18, 2025 neutral
Disclosure
Lemkin: Telling 100% of founders with strong M&A offers to sell in 2025
“Every single founder. That I, this year that has had a strong M&A offer. I've told them to take it a hundred percent of the time.”
Jason Lemkin Sep 18, 2025 ▶ 40:42 Opendoor CEO, Kaz Nejatian: OpenAI and Oracle, How Can Either Afford to Do This · 20VC with Harry Stebbings
Sep 18, 2025 negative
Assertion Not checkable as stated
Lemkin: Salesforce gets the majority of its growth from price increases
“At 11% growth, like Salesforce is probably getting the majority of its growth from price increases today.”
Jason Lemkin Sep 18, 2025 ▶ 1:29:45 Opendoor CEO, Kaz Nejatian: OpenAI and Oracle, How Can Either Afford to Do This · 20VC with Harry Stebbings
Sep 25, 2025 bullish
Assertion Supported
Lemkin: Nvidia free cash flow surged from $3.8B in FY23 to $60B in FY25
“NVIDIA fiscal year, 2023, 3.8 billion dollars in free cash flow fiscal 2023. Pretty good, right? 3.8 billion. Fiscal 2024, twenty seven billion. Fiscal 2025, sixty billion”
Jason Lemkin Sep 25, 2025 ▶ 16:07 The Impact of H1B Visas on Startups in the US & NVIDIA Invests $100BN Into OpenAI · 20VC with Harry Stebbings
Sep 25, 2025
Assertion Not checkable as stated
Lemkin: 100%+ growing startups face harder funding market than 2 years ago
“It's a lot more work to get funded growing a hundred percent at Twenty million, or a 110% of ten million than it was 24 months ago. It's just a lot more work, because you can't get the meeting.”
Jason Lemkin Sep 25, 2025 ▶ 27:04 The Impact of H1B Visas on Startups in the US & NVIDIA Invests $100BN Into OpenAI · 20VC with Harry Stebbings
Sep 25, 2025 neutral
Disclosure
Jason Lemkin is 0% cash, mirroring his 2008 fund allocation
“Well I'm excited because just like 2008 at the moment, I'm zero percent cash.”
Jason Lemkin Sep 25, 2025 ▶ 20:18 The Impact of H1B Visas on Startups in the US & NVIDIA Invests $100BN Into OpenAI · 20VC with Harry Stebbings
Sep 25, 2025 neutral
Insight
Jason Lemkin: Real founder-friendliness means writing checks when others won't
“Founder friendly is writing the check when no one else does. That's founder friendly. That founder friendly is when no one else is there at the board meeting anymore and you're there and you still have a W on the other side of it. That's founder friendly. Foun…”
Jason Lemkin Sep 25, 2025 ▶ 1:18:02 The Impact of H1B Visas on Startups in the US & NVIDIA Invests $100BN Into OpenAI · 20VC with Harry Stebbings
Sep 25, 2025 neutral
Disclosure
Lemkin: Wrote down all frothy portfolio holdings except one $300M ARR deal
“I wrote down everything. I guess a year and a half ago, whatever I get that I wrote every, everything that had a hint of froth. I have one deal. I'm still carrying myself, right? Because it's over three hundred million in revenue and growing. I'm holding it as…”
Jason Lemkin Sep 25, 2025 ▶ 1:12:42 The Impact of H1B Visas on Startups in the US & NVIDIA Invests $100BN Into OpenAI · 20VC with Harry Stebbings
Sep 25, 2025 negative
Insight
Jason Lemkin: LPs bragging on LinkedIn signals peak market froth
“The frothiest sign is now LinkedIn LPs are bragging about their returns on LinkedIn LPs. When LPs are start bragging about their returns to me that that's the most, 20, 21 moment I've seen when LPs are LPs who are usually hide behind the wizard of Oz curtain a…”
Jason Lemkin Sep 25, 2025 ▶ 21:57 The Impact of H1B Visas on Startups in the US & NVIDIA Invests $100BN Into OpenAI · 20VC with Harry Stebbings
Sep 25, 2025
Disclosure
Jason Lemkin invests nearly 10% per company across two checks
“I'm a pretty concentrated investor, so I'm gonna get to 10% almost in two checks into any deal”
Jason Lemkin Sep 25, 2025 ▶ 43:52 The Impact of H1B Visas on Startups in the US & NVIDIA Invests $100BN Into OpenAI · 20VC with Harry Stebbings
Sep 25, 2025 positive
What-if
Lemkin: First Startup Would Have Failed Without H-1B Visa Holders
“My especially my first startup, which was hard. It had a material science component. It wouldn't have been possible without H-one B at least on its surface. Okay. I had H-one B. I ate two folks with H-one Bs on my, They were transfers, right? I didn't sponsor …”
Jason Lemkin Sep 25, 2025 ▶ 1:05:06 The Impact of H1B Visas on Startups in the US & NVIDIA Invests $100BN Into OpenAI · 20VC with Harry Stebbings
Sep 25, 2025 positive
Assertion Not checkable as stated
Lemkin: Sam Altman fulfills predictions much faster than Elon Musk
“Elon Musk will say something, and it happens. He's just like a couple of years off, right? But it always happens. The self-driving cars and the rockets, right? Sam says something, and it happens, like, kind of soon”
Jason Lemkin Sep 25, 2025 ▶ 2:58 The Impact of H1B Visas on Startups in the US & NVIDIA Invests $100BN Into OpenAI · 20VC with Harry Stebbings
Sep 25, 2025 positive
Insight
Lemkin: Wealthy investors should hold winning public stocks indefinitely
“When you're up enough personally, it makes sense to hold your, all your winners in the public markets for taxes and other reasons. There's just no reason if you're personally up enough to sell any winner, right?”
Jason Lemkin Sep 25, 2025 ▶ 1:01:40 The Impact of H1B Visas on Startups in the US & NVIDIA Invests $100BN Into OpenAI · 20VC with Harry Stebbings
Oct 2, 2025 positive
Disclosure
Lemkin: SaaStr team replaced 11 human employees with AI agents
“I live it that we've replaced 11 people on our team with AI agents.”
Jason Lemkin Oct 2, 2025 ▶ 29:50 Are Burn Multiples BS in an AI World? & Sam Altman Needs $1TRN of Energy · 20VC with Harry Stebbings
Oct 2, 2025 neutral
Assertion Partly supported
Lemkin: 94% of public software companies call themselves AI companies
“94% of public software companies call themselves AI companies.”
Jason Lemkin Oct 2, 2025 ▶ 20:27 Are Burn Multiples BS in an AI World? & Sam Altman Needs $1TRN of Energy · 20VC with Harry Stebbings
Oct 9, 2025 positive
Disclosure
Lemkin: Built eight production apps in 200 hours on Replit
“I'm 200 hours in. I've gotten eight apps into production.”
Jason Lemkin Oct 9, 2025 ▶ 1:30:27 OpenAI's Multi-Billion Deal with AMD & Polymarket, Vercel and Supabase Raise Mega Rounds · 20VC with Harry Stebbings
Oct 9, 2025
Disclosure
Lemkin: SaaStr fund LPs have no legal rights to sell their stakes
“My LPs have no rights to sell at all. Like literally nothing. There's no exceptions for, you If you're struggling or if you're, or, it's just, I'm shocked because a lot of the stuff is LP friend. This one is absolute. You have no rights to sell.”
Jason Lemkin Oct 9, 2025 ▶ 38:58 OpenAI's Multi-Billion Deal with AMD & Polymarket, Vercel and Supabase Raise Mega Rounds · 20VC with Harry Stebbings
Oct 9, 2025 negative
Disclosure
Lemkin: Zero late-stage SaaS portfolio companies have received PE offers
“I have three companies that I would say are, I mean, different ARRs, but are in the same bucket that you're talking about, ok? What I'm worried about is zero have had PE offers.”
Jason Lemkin Oct 9, 2025 ▶ 48:24 OpenAI's Multi-Billion Deal with AMD & Polymarket, Vercel and Supabase Raise Mega Rounds · 20VC with Harry Stebbings
Oct 9, 2025 negative
Prediction Held up
Lemkin: Tim Cook will not step down as Apple CEO this year
“So it's their job, but there's no way it's this year. Unless it's a health issue, there's no way it's going to be this year.”
Jason Lemkin Oct 9, 2025 ▶ 1:27:56 OpenAI's Multi-Billion Deal with AMD & Polymarket, Vercel and Supabase Raise Mega Rounds · 20VC with Harry Stebbings
Oct 9, 2025 neutral
Disclosure
Lemkin: One top portfolio company burns heavily while another has 60-year runway
“I've got, I think two of my best current portfolio companies, one will consume an infinite amount of capital. The other has 60 years of runway.”
Jason Lemkin Oct 9, 2025 ▶ 1:17:59 OpenAI's Multi-Billion Deal with AMD & Polymarket, Vercel and Supabase Raise Mega Rounds · 20VC with Harry Stebbings
Oct 9, 2025 bullish
Prediction Held up
Lemkin: Replit and Lovable will surpass $250M combined ARR
“I would say over, over two 50, but barely.”
Jason Lemkin Oct 9, 2025 ▶ 1:29:34 OpenAI's Multi-Billion Deal with AMD & Polymarket, Vercel and Supabase Raise Mega Rounds · 20VC with Harry Stebbings
Oct 16, 2025 bullish
Assertion Not checkable as stated
Lemkin: Current AI Infrastructure Cannot Service Existing Market Demand
“I really do think we are not, I can see it myself. We're not remotely servicing the demand that exists today. Right? So how it gets paid for is a different question, but I think this is so different than the prior waves, where we just can't even service this d…”
Jason Lemkin Oct 16, 2025 ▶ 37:52 Thinking Machines Co-Founder Joins Meta for $3.5BN, Industry Venture's $665M Acquisition · 20VC with Harry Stebbings
Oct 16, 2025
Disclosure
Lemkin: Invests 8% of Fund per Seed Deal, Forcing High Hit Rate
“I'm doing eight percent of my fund into almost every deal, right? So I have to have such a high hit rate at seed.”
Jason Lemkin Oct 16, 2025 ▶ 1:12:02 Thinking Machines Co-Founder Joins Meta for $3.5BN, Industry Venture's $665M Acquisition · 20VC with Harry Stebbings
Oct 16, 2025 bullish
Prediction Not checkable as stated
Lemkin: Demand Will Absorb Every Available AI Token Produced
“Everyone will consume every available token.”
Jason Lemkin Oct 16, 2025 ▶ 37:12 Thinking Machines Co-Founder Joins Meta for $3.5BN, Industry Venture's $665M Acquisition · 20VC with Harry Stebbings
Oct 16, 2025 negative
Prediction Not checkable as stated
Lemkin: AI Developer Efficiency Will Increase Token Consumption, Not Reduce It
“The better that gets, the more tokens you'll consume. I don't think there's this, Great efficiency coming. I think it's, I think we'll get fat. We'll just build more and more stuff faster and faster.”
Jason Lemkin Oct 16, 2025 ▶ 40:53 Thinking Machines Co-Founder Joins Meta for $3.5BN, Industry Venture's $665M Acquisition · 20VC with Harry Stebbings
Oct 16, 2025 positive
Assertion Partly supported
Lemkin: AI Agents Replaced Almost All SaaStr Sales and Content Teams
“I Vibe Coded eight apps in a hundred days, and we have 12 AI agents working at Sastra now. Replaced all, almost all of our sales team and our whole content team.”
Jason Lemkin Oct 16, 2025 ▶ 36:56 Thinking Machines Co-Founder Joins Meta for $3.5BN, Industry Venture's $665M Acquisition · 20VC with Harry Stebbings
Oct 16, 2025
Insight
Lemkin: VCs With Double-Digit Ownership Must Serve on Boards Until Exit
“I think if you're going to own double digits, my view ethically is you got to be there till the end. Otherwise, you're dead weight on the cap table.”
Jason Lemkin Oct 16, 2025 ▶ 1:20:52 Thinking Machines Co-Founder Joins Meta for $3.5BN, Industry Venture's $665M Acquisition · 20VC with Harry Stebbings
Oct 30, 2025 positive
Disclosure
Lemkin: Salesloft exit at $2.5B in December 2021 was market peak
“My last deal sales off December, 20, 21, you know, two and a half billion.”
Jason Lemkin Oct 30, 2025 ▶ 1:16:23 OpenAI Restructuring: Who Wins and Who Loses & Mercor Raises $350M at a $10BN Valuation · 20VC with Harry Stebbings
Oct 30, 2025 negative
Opinion
Lemkin: $23B to $30B valuation bump is not a real up-round
“Going from twenty three billion to thirty billion, I don't even consider it an up round. It's not enough. It's not enough.”
Jason Lemkin Oct 30, 2025 ▶ 38:47 OpenAI Restructuring: Who Wins and Who Loses & Mercor Raises $350M at a $10BN Valuation · 20VC with Harry Stebbings
Nov 6, 2025 positive
Opinion
Lemkin: Kalshi is a safer long-term bet than Polymarket
“So based on my limited knowledge, I'm going Kalshi because I feel like it is a safer long-term bet than someone that is writing the current political vibes, which are all in favor of everything here. It just could, it was a lot different a couple of years ago,…”
Jason Lemkin Nov 6, 2025 ▶ 1:16:08 Is a $4.5BN Exit Enough in VC? & Harvey Raises $150M & Why Google is a Buy and Amazon is a Sell · 20VC with Harry Stebbings
Nov 6, 2025
Disclosure
Lemkin: Recently closed an early-stage deal at a $50M post-money valuation
“I just did a deal with some founders I love and it was very expensive for me. I did a deal at 50 post.”
Jason Lemkin Nov 6, 2025 ▶ 10:57 Is a $4.5BN Exit Enough in VC? & Harvey Raises $150M & Why Google is a Buy and Amazon is a Sell · 20VC with Harry Stebbings
Nov 6, 2025 negative
Opinion
Jason Lemkin: Seed stage venture investing is currently at its worst
“And I think it's the worst for seed because Everyone each year wants to be a seed investor even more. It's the, everyone, you know, what, you know, Jake Paul, Jake Logan, whatever, which are the Jake's you know, it's not just the chain smokers anymore, and Jar…”
Jason Lemkin Nov 6, 2025 ▶ 1:11:00 Is a $4.5BN Exit Enough in VC? & Harvey Raises $150M & Why Google is a Buy and Amazon is a Sell · 20VC with Harry Stebbings
Nov 6, 2025 bullish
Prediction Not checkable as stated
Lemkin: Harvey will improve next year and replace more legal associates
“Whatever Harvey is today, it's going to get better. And I guarantee you it's a better piece of software next year than it is at eight billion. Right. And it will replace more mediocre associates”
Jason Lemkin Nov 6, 2025 ▶ 1:01:50 Is a $4.5BN Exit Enough in VC? & Harvey Raises $150M & Why Google is a Buy and Amazon is a Sell · 20VC with Harry Stebbings
Nov 6, 2025 positive
Opinion
Jason Lemkin: Series A is experiencing its best-ever deal funnel
“This is a, the best of times to be a Series A investor because there is just an explosion of seed AI startups. There's so many and they can't all get funded. And I know it's stressful. I know it's hard, but it is a gift that thousands of founders are in San Fr…”
Jason Lemkin Nov 6, 2025 ▶ 1:10:17 Is a $4.5BN Exit Enough in VC? & Harvey Raises $150M & Why Google is a Buy and Amazon is a Sell · 20VC with Harry Stebbings
Nov 6, 2025 negative
Opinion
Lemkin Refuses to Take Meetings With 'Mortal Founders'
“For me, it's like, I don't even want to take meetings with mortal founders.”
Jason Lemkin Nov 6, 2025 ▶ 0:00 Is a $4.5BN Exit Enough in VC? & Harvey Raises $150M & Why Google is a Buy and Amazon is a Sell · 20VC with Harry Stebbings
Nov 6, 2025
Disclosure
Lemkin says his last three VC investments yielded 6-8% ownership
“And the last three investments I've done are in the six to eight percent range, even though that's my rule.”
Jason Lemkin Nov 6, 2025 ▶ 26:15 Is a $4.5BN Exit Enough in VC? & Harvey Raises $150M & Why Google is a Buy and Amazon is a Sell · 20VC with Harry Stebbings
Nov 13, 2025 negative
Prediction Open · timeframe Nov 2030
Lemkin: I Will Never Hold 18% Ownership at IPO Again
“And that's, I'm just obsessed with ownership now. It took me a long time to be obsessed with it, and now I've given up, but I don't see how I'll ever own 18% of something at IPO ever again, right?”
Jason Lemkin Nov 13, 2025 ▶ 1:13:26 Michael Burry Shorts NVIDIA and Palantir & Has Defensibility Died in a World of AI? · 20VC with Harry Stebbings
Nov 13, 2025
Disclosure
Lemkin: Founders Should Send Detailed Pitch Decks Before Requesting Meetings
“Don't get in the door with me. Just send me a great deck and a great email. I will read it. I will slow down. I will spend time. And if it looks good, I'll take the meeting, but don't, no need to get in the door with me.”
Jason Lemkin Nov 13, 2025 ▶ 49:16 Michael Burry Shorts NVIDIA and Palantir & Has Defensibility Died in a World of AI? · 20VC with Harry Stebbings
Nov 13, 2025 bullish
Assertion Supported
Lemkin: I Launched 10 Apps in 125 Days Without an Engineer
“So I've been vibe coding for a 126 days. Feels like a lot of change. So I did this presentation, all hands at Replit, 125 days and 10 apps. I launched 10 apps in 125 days without an engineer.”
Jason Lemkin Nov 13, 2025 ▶ 18:48 Michael Burry Shorts NVIDIA and Palantir & Has Defensibility Died in a World of AI? · 20VC with Harry Stebbings
Nov 13, 2025 negative
Insight
Lemkin: Early First-Month Growth Spikes Are No Longer Defensible
“You just can't take that early first month explosion as seriously as you used to. It's not as defensible.”
Jason Lemkin Nov 13, 2025 ▶ 0:12 Michael Burry Shorts NVIDIA and Palantir & Has Defensibility Died in a World of AI? · 20VC with Harry Stebbings
Nov 13, 2025 negative
Insight
Lemkin: The Best Fundraising Processes Do Not Require Traditional Data Rooms
“The optimal way to run it is for everyone already to want to invest for real without games before you open your data room. And the super optimal way doesn't even require a data room because they already, you don't even need a data room because they already wan…”
Jason Lemkin Nov 13, 2025 ▶ 55:05 Michael Burry Shorts NVIDIA and Palantir & Has Defensibility Died in a World of AI? · 20VC with Harry Stebbings
Nov 13, 2025
Disclosure
Lemkin: One Portfolio Startup Faced Five Clones Within 30 Days of Launch
“I can think of one investment I've made that has had five clones, like in the first 30 days, including one from a cloud leader.”
Jason Lemkin Nov 13, 2025 ▶ 25:44 Michael Burry Shorts NVIDIA and Palantir & Has Defensibility Died in a World of AI? · 20VC with Harry Stebbings
Nov 13, 2025 negative
Opinion
Lemkin: Current Startup Fundraising Market Is the Most Binary in Our Lifetimes
“It's the most binary fundraising environment in our lifetimes, isn't it? You're either, you know, you're either YC, Neo, South Park Commons, got something, get funded, or who the hell's gonna find you in your pre-seed round, right? You either got, you know, yo…”
Jason Lemkin Nov 13, 2025 ▶ 56:27 Michael Burry Shorts NVIDIA and Palantir & Has Defensibility Died in a World of AI? · 20VC with Harry Stebbings
Nov 13, 2025 negative
Insight
Lemkin: VC Partnerships Are Dysfunctional Due to Misaligned Carry Economics
“One of the reasons just partnerships are dysfunctional, and maybe it does, maybe we could move on, is that it's almost impossible for performance to tie to economics.”
Jason Lemkin Nov 13, 2025 ▶ 6:31 Michael Burry Shorts NVIDIA and Palantir & Has Defensibility Died in a World of AI? · 20VC with Harry Stebbings
Nov 20, 2025 neutral
Assertion Partly supported
Lemkin: Half of the $184B invested in VC in 2025 went to four companies
“They're estimated in a hundred eighty four billion in venture capital invested this year by their definition. Okay. The peak was 20, 21 of a hundred eighty three billion. So one more billion this year. Okay. But four of those half of the hundred eighty four bi…”
Jason Lemkin Nov 20, 2025 ▶ 55:01 Peter Thiel and Softbank Sell NVIDIA - Why? & Why VC Will Hit $1TRN and The Opening of Retail · 20VC with Harry Stebbings
Nov 20, 2025 bearish
Opinion
Lemkin: 900 late-stage unicorn startups generating nine-figure revenues will never go public
“And then we've got 900 unicorns that are never going to IPO. Poor guys. We have nine, we all have one or two in our portfolio that are at nine figures in revenue that are still growing and will never IPO. And there is no PE buyer for them.”
Jason Lemkin Nov 20, 2025 ▶ 56:02 Peter Thiel and Softbank Sell NVIDIA - Why? & Why VC Will Hit $1TRN and The Opening of Retail · 20VC with Harry Stebbings
Nov 20, 2025 bullish
Prediction Open · timeframe Dec 2030
Lemkin: 100% chance the US venture market hits $500B by 2030
“A hundred percent chance. So maybe more than a hundred.”
Jason Lemkin Nov 20, 2025 ▶ 53:42 Peter Thiel and Softbank Sell NVIDIA - Why? & Why VC Will Hit $1TRN and The Opening of Retail · 20VC with Harry Stebbings
Nov 20, 2025 bullish
Disclosure
Lemkin: Built 12 Replit apps used 700,000 times without knowing how to code
“Tomas, I've shipped 12 apps since June on Replit. 12 apps used 700,000 times since June, and I can ship, I built product, but I don't code, right?”
Jason Lemkin Nov 20, 2025 ▶ 7:05 Peter Thiel and Softbank Sell NVIDIA - Why? & Why VC Will Hit $1TRN and The Opening of Retail · 20VC with Harry Stebbings
Nov 27, 2025
Disclosure
Jason Lemkin: Hedge fund backed my VC fund solely for startup data
“I mean, I remember my first fund, I had a hedge fund invest. The only reason they invested was to get that data from the portfolio.”
Jason Lemkin Nov 27, 2025 ▶ 21:01 Anthropic Raises $30B from Microsoft & NVIDIA & NVIDIA’s Core Business Faces TPU Threat · 20VC with Harry Stebbings
Nov 27, 2025
Assertion Supported
Jason Lemkin: Public software multiples jump sharply above 20% and 30% growth
“If you're growing less than 20% of a cherry pick basket, 5.1 X AR, Wix is lower. It's not in my basket. 20 to 30, 11.8 X AR. And then the 30% plus, which is Rubrik, Palantir and Figma, average 23.7 X AR, but Palantir and Rubrik push that up.”
Jason Lemkin Nov 27, 2025 ▶ 1:04:20 Anthropic Raises $30B from Microsoft & NVIDIA & NVIDIA’s Core Business Faces TPU Threat · 20VC with Harry Stebbings
Nov 27, 2025
Insight
Jason Lemkin: Startup leaders cannot push their teams too hard
“I do not think you can push your team too hard. I think you should push them as hard as the business needs to go, and if they leave, it's great.”
Jason Lemkin Nov 27, 2025 ▶ 33:04 Anthropic Raises $30B from Microsoft & NVIDIA & NVIDIA’s Core Business Faces TPU Threat · 20VC with Harry Stebbings
Nov 27, 2025
Disclosure
Jason Lemkin: Portfolio firm sees 100% AI growth alongside flat legacy revenue
“And I was literally with a portfolio company. It's got. Forty-five million of AI revenue growing about a hundred percent. Okay. Now listen, that's not a lawful or, but it's pretty good. Okay. And then it's got fifty million of pre AI revenue growing zero.”
Jason Lemkin Nov 27, 2025 ▶ 47:13 Anthropic Raises $30B from Microsoft & NVIDIA & NVIDIA’s Core Business Faces TPU Threat · 20VC with Harry Stebbings
Nov 27, 2025 neutral
Insight
Jason Lemkin: Tech companies accomplish nothing unless operating in hyper-aggressive mode
“Across every professional experience I've had from startup to scale up to VP at a fortune, 500 tech company, nothing happens when you're not in hyper aggressive mode.”
Jason Lemkin Nov 27, 2025 ▶ 23:31 Anthropic Raises $30B from Microsoft & NVIDIA & NVIDIA’s Core Business Faces TPU Threat · 20VC with Harry Stebbings
Nov 27, 2025
Insight
Jason Lemkin: Low-growth software companies are worth only 3x to 5x ARR
“Generally, once you descend into low growth and that's different for public companies and private companies, you're worth, I mean, if you're worth anything, you might be worth nothing as a startup, you're worth in the three to five X ARR range”
Jason Lemkin Nov 27, 2025 ▶ 59:44 Anthropic Raises $30B from Microsoft & NVIDIA & NVIDIA’s Core Business Faces TPU Threat · 20VC with Harry Stebbings
Dec 4, 2025 positive
Insight
Lemkin: Databases Possess High Defensibility Due to Customer Switching Costs
“Databases are a hard problem. Like you can only lose so much data. You can only have so many issues. You have to figure this out. And five years of investing in a database that everybody uses, it's, it ain't so easy to turn and leave your database.”
Jason Lemkin Dec 4, 2025 ▶ 1:10:05 Eventbrite Sold for $500M, Databricks $5B Raise at $134B Valuation & Why SaaS is Like Japan · 20VC with Harry Stebbings
Dec 4, 2025 negative
Opinion
Lemkin: Goldman Sachs and Morgan Stanley Offer the World's Worst Products
“There's the world's crappiest product, which are Goldman Sachs and Morgan Stanley, which take one percent of your assets and do nothing.”
Jason Lemkin Dec 4, 2025 ▶ 52:33 Eventbrite Sold for $500M, Databricks $5B Raise at $134B Valuation & Why SaaS is Like Japan · 20VC with Harry Stebbings
Dec 4, 2025 negative
Opinion
Lemkin: Most Private SaaS Companies Are Caught in a TAM Trap
“The majority of the private tax companies, I think, are in a TAM trap.”
Jason Lemkin Dec 4, 2025 ▶ 0:10 Eventbrite Sold for $500M, Databricks $5B Raise at $134B Valuation & Why SaaS is Like Japan · 20VC with Harry Stebbings
Dec 4, 2025 neutral
Disclosure
Lemkin: Fastest-Growing Portfolio Companies Do Not Care About Profitability
“I think in the fastest growing companies that I've invested in, no one gives a rat's ass about the bottom line.”
Jason Lemkin Dec 4, 2025 ▶ 38:50 Eventbrite Sold for $500M, Databricks $5B Raise at $134B Valuation & Why SaaS is Like Japan · 20VC with Harry Stebbings
Dec 4, 2025 bearish
Opinion
Lemkin: SaaS Growth Has Stagnated Like Japan's Population
“SAS has become like Japan. It's a great economy, but if everyone only has .9 kids. I mean, there's only, only so many seats to go around.”
Jason Lemkin Dec 4, 2025 ▶ 0:20 Eventbrite Sold for $500M, Databricks $5B Raise at $134B Valuation & Why SaaS is Like Japan · 20VC with Harry Stebbings
Dec 4, 2025 negative
Disclosure
Lemkin: Startups Are Barely Discussing AI Security in Board Meetings
“I don't know how many board meetings you guys have been in where the first half of this presentation was how we're going to be more secure in the age of AI, but for me, it's been close to zero.”
Jason Lemkin Dec 4, 2025 ▶ 20:25 Eventbrite Sold for $500M, Databricks $5B Raise at $134B Valuation & Why SaaS is Like Japan · 20VC with Harry Stebbings
Dec 11, 2025 bullish
Insight
Lemkin: VCs Must Bet on Software Companies Tripling ARR to $150M
“If this growth is durable, ok, if we're seeing signs that it's durable, if it has, if it really has a 170% NRR and 98% logo retention, And it's accelerating at one 50. This is just the bet you do. You don't pull your hair out or have to have lengthy dinners ab…”
Jason Lemkin Dec 11, 2025 ▶ 45:07 SpaceX Valued at $800BN & Harvey Raises $160M at an $8BN Price & Netflix Acquires Warner Brothers · 20VC with Harry Stebbings
Dec 11, 2025 negative
Opinion
Lemkin: AI customer agents remain slow, setup-heavy, and prone to hallucinations
“I could, if you've used these products in the field, you can see on the one hand, they're amazing. On the other hand, they are slow. Okay. On the other hand, they are complicated to set up and ingest data. On the other hand, hallucinations are a minor issue, b…”
Jason Lemkin Dec 11, 2025 ▶ 54:47 SpaceX Valued at $800BN & Harvey Raises $160M at an $8BN Price & Netflix Acquires Warner Brothers · 20VC with Harry Stebbings
Dec 11, 2025 positive
Disclosure
Lemkin: Salesforce Agentforce takes 30 days to deploy and outperforms rivals
“We use Asian Force ourselves. It is great. I can talk to you how it really works. It takes about 30 days to train and deploy, and then you've got to keep going and upgrade and it's great. And it works just as well as the other agents. And in one way it works b…”
Jason Lemkin Dec 11, 2025 ▶ 1:01:32 SpaceX Valued at $800BN & Harvey Raises $160M at an $8BN Price & Netflix Acquires Warner Brothers · 20VC with Harry Stebbings
Dec 11, 2025 positive
Insight
Lemkin: Stair-Stepping Valuations in Hot Deals Efficiently Filters Oversubscribed VCs
“But it is, it does work in my limited experience because even if you do three rounds at the same day at 306 109 hundred or whatever it is, when you're oversubscribed, it's just a message to the new investors. The price is 900. It might be, the price might even…”
Jason Lemkin Dec 11, 2025 ▶ 39:12 SpaceX Valued at $800BN & Harvey Raises $160M at an $8BN Price & Netflix Acquires Warner Brothers · 20VC with Harry Stebbings
Dec 11, 2025
Insight
Lemkin: Being Too Negative on B2B TAM Always Bites VCs
“And at my entire life in B to B as a founder or investor, every time we try to be too negative on TAM, it bites us.”
Jason Lemkin Dec 11, 2025 ▶ 44:22 SpaceX Valued at $800BN & Harvey Raises $160M at an $8BN Price & Netflix Acquires Warner Brothers · 20VC with Harry Stebbings
Dec 22, 2025 negative
Opinion
Lemkin: Paid standalone AI co-pilots were B2B software's biggest 2025 failure
“The biggest failing of this year, we talked about, I want to say in twenties, going to Rory's point, it was the co-pilot. The co-pilot was the worst of all worlds. We're not going to put it in our base product. We're not going to make the core product better, …”
Jason Lemkin Dec 22, 2025 ▶ 53:48 Predictions for 2026: Top Buy & Biggest Short | Why Salesforce Could Win & NVIDIA’s Challenges · 20VC with Harry Stebbings
Dec 22, 2025 bullish
Prediction Held up
Lemkin: 2026 will see one or two trillion-dollar tech IPOs
“The idea that we will have a trillion dollar IPO next year, maybe two, we might have two trillion dollar IPOs”
Jason Lemkin Dec 22, 2025 ▶ 30:28 Predictions for 2026: Top Buy & Biggest Short | Why Salesforce Could Win & NVIDIA’s Challenges · 20VC with Harry Stebbings
Dec 22, 2025 negative
Opinion
Lemkin: Adobe's $5B 'AI-influenced revenue' metric is misleading vanity reporting
“The worst offender is Adobe, okay? Because Adobe announced they had five billion of quote, AI influenced revenue this year. That, listen, let, Let's be kind. It's, I'm sure it's true. I'm sure they're using Firefly and generating images with AI, but to me, it …”
Jason Lemkin Dec 22, 2025 ▶ 49:19 Predictions for 2026: Top Buy & Biggest Short | Why Salesforce Could Win & NVIDIA’s Challenges · 20VC with Harry Stebbings
Dec 22, 2025 bullish
Prediction Not checkable as stated
Lemkin: Salesforce will be the biggest public tech stock beneficiary in 2026
“I think Salesforce might be the biggest beneficiary next year, and I'll tell you why, because it has, it is, like, you have to also, we go through the ones that declined the most this year, and you have to be honest, are they at least tapping into AI tailwinds…”
Jason Lemkin Dec 22, 2025 ▶ 41:50 Predictions for 2026: Top Buy & Biggest Short | Why Salesforce Could Win & NVIDIA’s Challenges · 20VC with Harry Stebbings
Jan 8, 2026 bearish
Prediction Not checkable as stated
Lemkin: Invisible tech unemployment will grow significantly throughout 2026
“I call it invisible unemployment, and it's all around us, and it's gonna grow this year. It doesn't show up in the government numbers yet but it's everywhere.”
Jason Lemkin Jan 8, 2026 ▶ 1:15:59 Groq’s $20BN NVIDIA Deal | Why Sam Altman Doesn’t Care About Dilution & Invisible Unemployment 2026 · 20VC with Harry Stebbings
Jan 8, 2026
Insight
Lemkin: VCs can identify top 0.1% founders without speaking to them
“You can identify a point, a top, oh.1% founder Without talking to them. I don't think you can do it without any interactions, but without talk, I do, I a hundred percent believe it's possible.”
Jason Lemkin Jan 8, 2026 ▶ 59:37 Groq’s $20BN NVIDIA Deal | Why Sam Altman Doesn’t Care About Dilution & Invisible Unemployment 2026 · 20VC with Harry Stebbings
Jan 8, 2026 positive
Disclosure
Lemkin: Most of my best deals originated from cold emails
“Most of my best deals have been from cold inbounds and I have begun that journey by analyzing the in inbound, analyzing the intelligence and the quality of the founder, analyzing this. It's not an, and I've done multiple billion dollar exits from cold inbound.”
Jason Lemkin Jan 8, 2026 ▶ 59:49 Groq’s $20BN NVIDIA Deal | Why Sam Altman Doesn’t Care About Dilution & Invisible Unemployment 2026 · 20VC with Harry Stebbings
Jan 8, 2026 bearish
Prediction Partly held up
Lemkin: 2026 will mark the end of entry-level sales jobs
“There'll be, this is the year where we will see the end of so many entry-level sales jobs. We still need AEs. We still need people knocking on doors. We do not need two-year-old kids sending emails. Those jobs will disappear.”
Jason Lemkin Jan 8, 2026 ▶ 1:18:01 Groq’s $20BN NVIDIA Deal | Why Sam Altman Doesn’t Care About Dilution & Invisible Unemployment 2026 · 20VC with Harry Stebbings
Jan 8, 2026 bullish
Prediction Open · timeframe Jan 2027
Lemkin: Aims to invest in one AI agent startup per quarter
“I've got to work on AI agents. That's where I get so much because of all this SaaS stuff, I get so much inbound on AI agents, whether it's GTM or otherwise, I got to pick the best thing I can once a quarter and just do that deal and just try to do a 50 X or a …”
Jason Lemkin Jan 8, 2026 ▶ 56:30 Groq’s $20BN NVIDIA Deal | Why Sam Altman Doesn’t Care About Dilution & Invisible Unemployment 2026 · 20VC with Harry Stebbings
Jan 8, 2026 negative
Insight
Lemkin: Workforce reskilling is a total delusion that never succeeds
“Reskill is a delusion. Reskill is something we say to make everybody feel better. Reskilling is like when you get, when you, they do layoffs and they bring you in the room and they give you a packet of jobs potentially. It's just to make people feel better. No…”
Jason Lemkin Jan 8, 2026 ▶ 1:16:47 Groq’s $20BN NVIDIA Deal | Why Sam Altman Doesn’t Care About Dilution & Invisible Unemployment 2026 · 20VC with Harry Stebbings
Jan 8, 2026 bearish
Insight
Lemkin: Investing in part-time, non-executive chairman founders is flushing money
“I believe, and don't get me wrong, this particular deal may work, but in my life experience, You're just flushing your money down the toilet. When a great seat founder reaches out to you, I've got this one I want to do. And then you dig a little deeper. I'm th…”
Jason Lemkin Jan 8, 2026 ▶ 33:01 Groq’s $20BN NVIDIA Deal | Why Sam Altman Doesn’t Care About Dilution & Invisible Unemployment 2026 · 20VC with Harry Stebbings
Jan 8, 2026
Prediction Not checkable as stated
Lemkin: I will never lower my investment standards again
“I'm no longer ever going to lower the bar. If it means I do one deal every two years, don't care. Never gonna lower the bar again, not once.”
Jason Lemkin Jan 8, 2026 ▶ 58:37 Groq’s $20BN NVIDIA Deal | Why Sam Altman Doesn’t Care About Dilution & Invisible Unemployment 2026 · 20VC with Harry Stebbings
Jan 8, 2026 positive
Disclosure
Lemkin: Startup founders should always sell when offered an acquisition
“I tell all founders to sell. That's my advice.”
Jason Lemkin Jan 8, 2026 ▶ 27:21 Groq’s $20BN NVIDIA Deal | Why Sam Altman Doesn’t Care About Dilution & Invisible Unemployment 2026 · 20VC with Harry Stebbings
Jan 8, 2026 positive
Prediction Not checkable as stated
Lemkin: Longevity will be the dominant tech theme of 2027
“This will be the year of twenty-four-seven AI, but I think longevity will be the theme of twenty-twenty-seven.”
Jason Lemkin Jan 8, 2026 ▶ 37:21 Groq’s $20BN NVIDIA Deal | Why Sam Altman Doesn’t Care About Dilution & Invisible Unemployment 2026 · 20VC with Harry Stebbings
Jan 8, 2026 positive
Disclosure
Lemkin: Completed a VC investment recommended by an AI VC tool
“I've done one deal cause my AI VC recommended it, which is, that's exactly it. So that's one, and that's just a start. That was just 20, 25.”
Jason Lemkin Jan 8, 2026 ▶ 57:46 Groq’s $20BN NVIDIA Deal | Why Sam Altman Doesn’t Care About Dilution & Invisible Unemployment 2026 · 20VC with Harry Stebbings
Jan 15, 2026 positive
Assertion Not publicly verifiable
Lemkin: One in three Nvidia employees is worth $20M or more
“One in three employees in NVIDIA is now worth twenty million or more. One in three. Okay. 18,000 folks in NVIDIA are worth twenty-five million or more.”
Jason Lemkin Jan 15, 2026 ▶ 1:28:26 Anthropic’s $10B Raise | a16z’s $15B Fund: Is the Middle Dead in VC? | How OpenAI Could Go to Zero? · 20VC with Harry Stebbings
Jan 15, 2026 neutral
Prediction Open · timeframe Jan 2031
Lemkin: B2B SaaS will normalize around $1M-$2M revenue per employee
“I think for, even for B to B grounded in what we do, I think we're going to normalize around a million dollars to two million dollars per employee.”
Jason Lemkin Jan 15, 2026 ▶ 1:27:17 Anthropic’s $10B Raise | a16z’s $15B Fund: Is the Middle Dead in VC? | How OpenAI Could Go to Zero? · 20VC with Harry Stebbings
Jan 15, 2026 bearish
Disclosure
Lemkin: I would not invest in ElevenLabs at an $11B valuation
“At eleven billion, no.”
Jason Lemkin Jan 15, 2026 ▶ 1:03:49 Anthropic’s $10B Raise | a16z’s $15B Fund: Is the Middle Dead in VC? | How OpenAI Could Go to Zero? · 20VC with Harry Stebbings
Jan 15, 2026 bearish
Prediction Not checkable as stated
Lemkin: AI substitution risk will become critical in H2 2026
“This will be the year. It'll probably be the back half of the year where we have to take substitution risks seriously in AI.”
Jason Lemkin Jan 15, 2026 ▶ 1:05:47 Anthropic’s $10B Raise | a16z’s $15B Fund: Is the Middle Dead in VC? | How OpenAI Could Go to Zero? · 20VC with Harry Stebbings
Jan 15, 2026 negative
Prediction Not checkable as stated
Lemkin: AI wealth disparity will drive growing social unrest
“I do think there is a level of social unrest that will grow over the coming years.”
Jason Lemkin Jan 15, 2026 ▶ 1:29:39 Anthropic’s $10B Raise | a16z’s $15B Fund: Is the Middle Dead in VC? | How OpenAI Could Go to Zero? · 20VC with Harry Stebbings
Jan 22, 2026 negative
Prediction Not checkable as stated
Lemkin: Will Never Invest in Technical Startups Lacking Technical CEOs
“I'm super skeptical of technical companies where the CEO isn't One of the greatest technical visionaries in the industry. I'm just, I'll never do that investment again. I'll never do an investment again where, where, where it's not like Databricks are better a…”
Jason Lemkin Jan 22, 2026 ▶ 16:35 Elon Musk vs Sam Altman | The Implosion of Thinking Machines | Can VC Survive Public Pricing? · 20VC with Harry Stebbings
Jan 22, 2026 bullish
Disclosure
Lemkin: Conducts Vendor Discovery on Claude Rather Than Google
“I do my vendor discovery on Claude and a little bit on Google. That's when I want to find a new tool or a new product, that's where I start. I start with LLMs”
Jason Lemkin Jan 22, 2026 ▶ 46:37 Elon Musk vs Sam Altman | The Implosion of Thinking Machines | Can VC Survive Public Pricing? · 20VC with Harry Stebbings
Jan 22, 2026
Disclosure
Lemkin: Has Not Acquired a 20% Startup Ownership Stake in Seven Years
“I haven't bought 20% of a startup in like seven years. So, and I haven't done around at a million in revenue growing quickly in the teens in a decade.”
Jason Lemkin Jan 22, 2026 ▶ 9:05 Elon Musk vs Sam Altman | The Implosion of Thinking Machines | Can VC Survive Public Pricing? · 20VC with Harry Stebbings
Jan 29, 2026 neutral
Insight
Lemkin: Companies of any scale only need two or three key leaders
“You only need two or three leaders, a company of any scale. The best ones will find two or three.”
Jason Lemkin Jan 29, 2026 ▶ 1:03:01 Anthropic Inference Costs Skyrocket |TikTok Deal Closes |The IPO Market:Wealthfront & EquipmentShare · 20VC with Harry Stebbings
Jan 29, 2026 positive
Opinion
Lemkin: Failed founders are currently the hottest tech recruiting category
“They may be failed founders themselves, which is like the hottest recruiting category in tech right now, right?”
Jason Lemkin Jan 29, 2026 ▶ 1:02:50 Anthropic Inference Costs Skyrocket |TikTok Deal Closes |The IPO Market:Wealthfront & EquipmentShare · 20VC with Harry Stebbings
Jan 29, 2026 bearish
Prediction Not checkable as stated
Lemkin: High inference costs will ruin mature mid-tier SaaS companies
“I worry this is the next final act is that you checked out, you did all the right things, right? You're not growing zero percent. Your customers don't hate you. You built an agent and the final nail in the coffin is we just can't afford the inference. We just …”
Jason Lemkin Jan 29, 2026 ▶ 28:31 Anthropic Inference Costs Skyrocket |TikTok Deal Closes |The IPO Market:Wealthfront & EquipmentShare · 20VC with Harry Stebbings
Jan 29, 2026 negative
Insight
Lemkin: B2B startups cannot cut AI inference costs and stay competitive
“The idea that you can use. Cheap models and cut back on your inference and still be competitive? That's the thing. Still be competitive with the hot Andreessen-funded company? Like, no chance you can be competitive without that inference.”
Jason Lemkin Jan 29, 2026 ▶ 19:56 Anthropic Inference Costs Skyrocket |TikTok Deal Closes |The IPO Market:Wealthfront & EquipmentShare · 20VC with Harry Stebbings
Jan 29, 2026 bullish
Insight
Lemkin: AI inference costs are replacing traditional sales and marketing budgets
“The other advantage that the new entrants have is that if you have the best agent and you have the kind of market demand we see, right, then you're for you, your inference costs are a marketing cost. The established players don't have that luxury. They're alre…”
Jason Lemkin Jan 29, 2026 ▶ 31:12 Anthropic Inference Costs Skyrocket |TikTok Deal Closes |The IPO Market:Wealthfront & EquipmentShare · 20VC with Harry Stebbings
Jan 29, 2026 bearish
Prediction Open · timeframe Jan 2027
Lemkin: AI startups must model inference costs rising in 2026
“You need to model in your inference costs are going up this year, not down.”
Jason Lemkin Jan 29, 2026 ▶ 23:45 Anthropic Inference Costs Skyrocket |TikTok Deal Closes |The IPO Market:Wealthfront & EquipmentShare · 20VC with Harry Stebbings
Jan 29, 2026 negative
Insight
Lemkin: Venture capital is not an asset class because the bottom 75% underperforms
“The classic take in ventures, it's not really an asset class. It's a weird niche of PE. Yes, the top Your quartile, certainly the top decile perform, but the rest is a disaster. So it's not an asset class. If the bottom 75% isn't even worth getting out of bed …”
Jason Lemkin Jan 29, 2026 ▶ 48:33 Anthropic Inference Costs Skyrocket |TikTok Deal Closes |The IPO Market:Wealthfront & EquipmentShare · 20VC with Harry Stebbings
Jan 29, 2026 bearish
Opinion
Lemkin: Current market pressures are the final nail for traditional SaaS
“When we talk about is SaaS dead, or what's going on, I worry this is the next final act. I think it's the final nail.”
Jason Lemkin Jan 29, 2026 ▶ 0:25 Anthropic Inference Costs Skyrocket |TikTok Deal Closes |The IPO Market:Wealthfront & EquipmentShare · 20VC with Harry Stebbings
Jan 29, 2026 negative
Opinion
Lemkin: 80% of employees at top companies do not add value
“The reality is even at the best, 80% of folks are not contributing significant value mathematically, but.”
Jason Lemkin Jan 29, 2026 ▶ 1:05:15 Anthropic Inference Costs Skyrocket |TikTok Deal Closes |The IPO Market:Wealthfront & EquipmentShare · 20VC with Harry Stebbings
Jan 29, 2026 bullish
Prediction Not checkable as stated
Lemkin: No upside for founders in betting AI slows in 24 months
“There's no upside in, in, in, in betting this is gonna slow in the next 24 months. There's literally, at least for 99.9% of us, there's no upside.”
Jason Lemkin Jan 29, 2026 ▶ 38:28 Anthropic Inference Costs Skyrocket |TikTok Deal Closes |The IPO Market:Wealthfront & EquipmentShare · 20VC with Harry Stebbings
Jan 29, 2026 bearish
Assertion Supported
Lemkin: Wealthfront's IPO is deeply broken and trading down 30-40%
“It's a deeply broken IPO. You know, it's trading down what? 30 or 40% from its IPO and it's subscale. Like it's worse. It's subscale, right?”
Jason Lemkin Jan 29, 2026 ▶ 1:00:09 Anthropic Inference Costs Skyrocket |TikTok Deal Closes |The IPO Market:Wealthfront & EquipmentShare · 20VC with Harry Stebbings
Jan 29, 2026 negative
Assertion Not checkable as stated
Lemkin: Salesforce employees call current AI era most stressful in company history
“And I don't see how even Salesforce is one of the few that can do it with its resources. And even there, it's stressful. If you talk to folks at Salesforce today, they'll tell you this is the most stressful time they've ever worked at Salesforce in history of …”
Jason Lemkin Jan 29, 2026 ▶ 32:00 Anthropic Inference Costs Skyrocket |TikTok Deal Closes |The IPO Market:Wealthfront & EquipmentShare · 20VC with Harry Stebbings
Feb 5, 2026 bearish
Prediction Not checkable as stated
Lemkin: Agent-to-agent AI communication will disrupt massive amounts of B2B software
“I think it will disrupt massive amounts of B to B in software when agents can communicate with each other.”
Jason Lemkin Feb 5, 2026 ▶ 1:28:17 The SaaS Massacre: Public Market Collapse |Microsoft Lost $360B & NVIDIA’s $100B Dispute with OpenAI
Feb 5, 2026 neutral
Prediction Not checkable as stated
Lemkin: New venture capital investors have only 22 months to prove themselves
“I think you got 22 months to prove yourself in venture. I think you get 22 months.”
Jason Lemkin Feb 5, 2026 ▶ 26:05 The SaaS Massacre: Public Market Collapse |Microsoft Lost $360B & NVIDIA’s $100B Dispute with OpenAI
Feb 5, 2026 bearish
Insight
Lemkin: Non-hypergrowth private software startups are now completely unfundable
“I think there are only two types of companies for private companies. They're growing at insane rates or they're unfundable.”
Jason Lemkin Feb 5, 2026 ▶ 21:27 The SaaS Massacre: Public Market Collapse |Microsoft Lost $360B & NVIDIA’s $100B Dispute with OpenAI
Feb 5, 2026 neutral
Assertion Not checkable as stated
Lemkin: Software companies need a $4B valuation and 50% growth to IPO
“No, I think four billion growing 50% or more is the new IPO to have a good IPO. That's where we're at today. Four billion growing 50% or more.”
Jason Lemkin Feb 5, 2026 ▶ 10:55 The SaaS Massacre: Public Market Collapse |Microsoft Lost $360B & NVIDIA’s $100B Dispute with OpenAI
Feb 12, 2026 bearish
Assertion Not checkable as stated
Lemkin: Non-engineering software categories face existential seat shrinking
“Every category that I know of outside of engineering and product is at existential risk of shrinking seats.”
Jason Lemkin Feb 12, 2026 ▶ 41:06 Anthropic's Super Bowl Ad: Who Won & Lost? | Sierra Hits $150M ARR: Is Customer Support Too Crowded? · 20VC with Harry Stebbings
Feb 12, 2026 negative
Insight
Lemkin: Investors must abandon traditional TAM calculations for revenue trajectory
“I just think we have to give up on TAM. We just have to let the revenue show us the path to TAM.”
Jason Lemkin Feb 12, 2026 ▶ 0:14 Anthropic's Super Bowl Ad: Who Won & Lost? | Sierra Hits $150M ARR: Is Customer Support Too Crowded? · 20VC with Harry Stebbings
Feb 12, 2026 neutral
Assertion Supported
Lemkin: Replit hits $300M revenue with 300 employees and 11 GTM staff
“I was at Replit the other day at three hundred million in revenue, 300 people. It's, there's like 11 people in go to market.”
Jason Lemkin Feb 12, 2026 ▶ 14:00 Anthropic's Super Bowl Ad: Who Won & Lost? | Sierra Hits $150M ARR: Is Customer Support Too Crowded? · 20VC with Harry Stebbings
Feb 12, 2026 bullish
Assertion Open
Lemkin: No software companies are reducing their engineering teams
“We are building more software than ever, and we need the humans and no one is reducing their engineering team.”
Jason Lemkin Feb 12, 2026 ▶ 40:29 Anthropic's Super Bowl Ad: Who Won & Lost? | Sierra Hits $150M ARR: Is Customer Support Too Crowded? · 20VC with Harry Stebbings
Feb 19, 2026 bearish
Opinion
Lemkin: Distressed SaaS companies in 'hospice care' never recover
“If you've gone on to hospice care, does it really matter how long you stay in hospice? I mean, to the kid, to the employees, it does to the family, but everybody pretty much knows when that SAS company goes into hospice, it ain't coming out.”
Jason Lemkin Feb 19, 2026 ▶ 43:12 Thrive Raises New $10B Fund | OpenAI Buys OpenClaw | Stripe at $140B: Is Adyen Wildly Undervalued? · 20VC with Harry Stebbings
Feb 19, 2026 bearish
Disclosure
Lemkin: Fund sits at 4.5x, but non-AI startups are struggling
“When I look at my last fund, right, you know, and I see what's happening and it, the funds in good shape, whatever, 4.5 X. But honestly, like two companies are like, Massively benefiting from the current world and B to B massively benefit in accelerating. One …”
Jason Lemkin Feb 19, 2026 ▶ 27:28 Thrive Raises New $10B Fund | OpenAI Buys OpenClaw | Stripe at $140B: Is Adyen Wildly Undervalued? · 20VC with Harry Stebbings
Feb 19, 2026 bearish
Opinion
Jason Lemkin Sees No Valuation Floor for Shopify Stock
“And I love Shopify. It's because I just, I don't see the floor.”
Jason Lemkin Feb 19, 2026 ▶ 1:34:13 Thrive Raises New $10B Fund | OpenAI Buys OpenClaw | Stripe at $140B: Is Adyen Wildly Undervalued? · 20VC with Harry Stebbings
Feb 19, 2026 neutral
Disclosure
Lemkin hasn't logged into Salesforce in six months; AI agents run it
“I haven't logged into Salesforce in six months. But we use it every, every minute. Our agents use it every minute.”
Jason Lemkin Feb 19, 2026 ▶ 24:40 Thrive Raises New $10B Fund | OpenAI Buys OpenClaw | Stripe at $140B: Is Adyen Wildly Undervalued? · 20VC with Harry Stebbings
Feb 19, 2026 positive
Insight
Lemkin: Traditional 2022 SaaS playbooks still work at top AI companies
“The 2023, 20 22 toolkit works perfectly well at the hottest AI companies. It really does. It really does.”
Jason Lemkin Feb 19, 2026 ▶ 1:23:48 Thrive Raises New $10B Fund | OpenAI Buys OpenClaw | Stripe at $140B: Is Adyen Wildly Undervalued? · 20VC with Harry Stebbings
Feb 19, 2026 bearish
Insight
Lemkin: AI agent vendors lack defensibility because customers rapidly switch products
“I'd actually don't think any of the agent vendors are safe from disruption because we will, even us, like everyone's promiscuous with agents. We will switch it. Like, this is so much better than what we had two weeks ago. We'll switch to the next one.”
Jason Lemkin Feb 19, 2026 ▶ 41:36 Thrive Raises New $10B Fund | OpenAI Buys OpenClaw | Stripe at $140B: Is Adyen Wildly Undervalued? · 20VC with Harry Stebbings
Feb 26, 2026 bearish
Prediction Not checkable as stated
Lemkin: Software firms failing to own category AI agents will be maimed
“No, I think just people are going to be maimed even more than they think if they don't own the agents in your category. You've got to own the agents in your category. And whether those agents are owned by a startup, or whether some version of that agent can be…”
Jason Lemkin Feb 26, 2026 ▶ 18:06 Citrini Research Breakdown: Agents, "Ghost GDP", Consumer Spend | Figma Earnings Beat · 20VC with Harry Stebbings
Feb 26, 2026 bullish
Disclosure
Lemkin: Portfolio data from 10,000 restaurants proves AI food ordering adoption
“I have an investment in this space. I already know the answer is yes. It's not my opinion. I have data from over 10,000 restaurants.”
Jason Lemkin Feb 26, 2026 ▶ 33:51 Citrini Research Breakdown: Agents, "Ghost GDP", Consumer Spend | Figma Earnings Beat · 20VC with Harry Stebbings
Feb 26, 2026 negative
Disclosure
Lemkin: Two of my portfolio investments from last year are now obsolete
“I have two investments I made last year. I love them. Those products no longer have a reason to exist today because of Claude.”
Jason Lemkin Feb 26, 2026 ▶ 20:13 Citrini Research Breakdown: Agents, "Ghost GDP", Consumer Spend | Figma Earnings Beat · 20VC with Harry Stebbings
Feb 26, 2026
Prediction Open · timeframe Feb 2028
Lemkin: AI agents will stop requiring custom setup within two years
“Every agent, here's the problem today, and this will change in the next two years. It is not true today. Every agent is essentially custom, ok? Every agent needs to be trained. Every agent needs to be onboarded. If you want it to be great, ok? Every agent need…”
Jason Lemkin Feb 26, 2026 ▶ 14:57 Citrini Research Breakdown: Agents, "Ghost GDP", Consumer Spend | Figma Earnings Beat · 20VC with Harry Stebbings
Feb 26, 2026 bearish
Opinion
Lemkin: AI-generated YouTube videos are utterly disruptive to Netflix
“And as of the last 45 days, you can watch an incredible short on YouTube that was entirely AI generated where you can watch Star Wars stories that are better than the crappy last three movies that are AI generated. That's utterly disruptive to Netflix.”
Jason Lemkin Feb 26, 2026 ▶ 31:22 Citrini Research Breakdown: Agents, "Ghost GDP", Consumer Spend | Figma Earnings Beat · 20VC with Harry Stebbings
Feb 26, 2026 positive
Disclosure
Lemkin: SaaStr team shrank to two while generating eight-figure revenue
“We have gone from 12 people to two people on my little team. Okay. That not only does investment, it generates eight figures a year in revenue, okay?”
Jason Lemkin Feb 26, 2026 ▶ 35:38 Citrini Research Breakdown: Agents, "Ghost GDP", Consumer Spend | Figma Earnings Beat · 20VC with Harry Stebbings
Feb 26, 2026 negative
Prediction Open · timeframe Feb 2031
Lemkin: I will never host another LP Annual General Meeting
“I told my LPs and COVID I'm not doing this. I'm not doing any more AGMs. I'm not standing up there with like, here's the numbers. I'll go talk to you. Like I'll drop by your office, but I'm done with this performative. All day circus of an AGM. It's not that I…”
Jason Lemkin Feb 26, 2026 ▶ 1:20:05 Citrini Research Breakdown: Agents, "Ghost GDP", Consumer Spend | Figma Earnings Beat · 20VC with Harry Stebbings
Feb 26, 2026 bullish
Prediction Not checkable as stated
Jason Lemkin shifts strategy to focus exclusively on momentum tech stocks
“I'm gonna be a momentum better investor here. There's just so much and so much uncertainty. I'm gonna bet on the ones that are winning because I believe success will beget success, that the best people will continue to go.”
Jason Lemkin Feb 26, 2026 ▶ 1:07:16 Citrini Research Breakdown: Agents, "Ghost GDP", Consumer Spend | Figma Earnings Beat · 20VC with Harry Stebbings
Mar 5, 2026 negative
Assertion Not checkable as stated
Lemkin: Every tech CEO believes they can cut 40% of staff
“Every single CEO I talked to doesn't think they need 40% of their team.”
Jason Lemkin Mar 5, 2026 ▶ 0:30 Anthropic vs The Pentagon: Who Wins? | OpenAI's $110BN Mega Round | Cursor Hits $2BN in ARR · 20VC with Harry Stebbings
Mar 9, 2026 negative
Opinion
Stebbings: Jason Lemkin says SaaS VC investing is exhausting compared to AI
“I was talking to my dear friend Jason Lemkin the other day, and he's like, fuck this. I've had enough of this. I just want to do an anthropic SPV and go home. I don't want to pick the winner in a SaaS company.”
Harry Stebbings Mar 9, 2026 ▶ 25:39 "Cursor is Dead" is Total BS: Here is Why | Miles Clements · 20VC with Harry Stebbings
Mar 12, 2026 negative
Prediction Open · timeframe Dec 2027
Lemkin: Junior role elimination will spread to sales by 2027
“This is my big worry for 20, 27 is it happens. It's going to be true in sales. It's already true in support.”
Jason Lemkin Mar 12, 2026 ▶ 32:38 Anthropic vs The Pentagon: Who Wins? | The Data Center Arms Race | The Ultimate Stock Picks · 20VC with Harry Stebbings
Mar 12, 2026 negative
Prediction Not checkable as stated
Lemkin: AI Boom Will Lead Tech Leaders to Abandon Moral Standards
“I think we're gonna discard more and more of our previous moral standards, and maybe it's, that's the AI life, but I have a little bit of anxiety here.”
Jason Lemkin Mar 12, 2026 ▶ 15:25 Anthropic vs The Pentagon: Who Wins? | The Data Center Arms Race | The Ultimate Stock Picks · 20VC with Harry Stebbings
Mar 12, 2026 bearish
Disclosure
Lemkin: Refuses to invest in Snowflake or MongoDB because they lack founders
“The only reason I ding Snowflake is, and this is no, I couldn't do better is it's not founder led. And it's just, that's my thesis today. Like I can't pick Mongo or I killed Mongo or Snowflake just on not being founder led.”
Jason Lemkin Mar 12, 2026 ▶ 1:16:15 Anthropic vs The Pentagon: Who Wins? | The Data Center Arms Race | The Ultimate Stock Picks · 20VC with Harry Stebbings
Mar 12, 2026 negative
Insight
Lemkin: Next-Gen AI CRMs Cannot Function With Workplace Privacy
“App is, this is becoming necessary core CRM functionality to record and manage every keystroke, every interaction, everything you type, everything you do, because otherwise you can't automate a CRM. Like, the next generation CRM just does not work if you have …”
Jason Lemkin Mar 12, 2026 ▶ 14:45 Anthropic vs The Pentagon: Who Wins? | The Data Center Arms Race | The Ultimate Stock Picks · 20VC with Harry Stebbings
Mar 12, 2026 bearish
Assertion Not checkable as stated
Lemkin: Oracle lacks the cash to keep up in AI compute race
“Oracle doesn't have the cash to keep up, going to Harry's point. It just doesn't have the cash.”
Jason Lemkin Mar 12, 2026 ▶ 21:27 Anthropic vs The Pentagon: Who Wins? | The Data Center Arms Race | The Ultimate Stock Picks · 20VC with Harry Stebbings
Mar 19, 2026 positive
Insight
Lemkin: Prompt engineering is dead; ADE is the vital modern role
“The job today is not to screw around on ChatGPT and to be a prompt engineer. The job today is to bring the best AI and agent, agentic products into your organization and leverage all the hard work that the engineers have done building those products. That's yo…”
Jason Lemkin Mar 19, 2026 ▶ 23:33 NVIDIA Predicts $1TRN in Revenue: Everything You Need to Know From GTC & Anduril Lands $20B Contract · 20VC with Harry Stebbings
Mar 19, 2026 neutral
Opinion
Lemkin: Meta and Atlassian layoffs are voluntary, not financially forced
“Neither of these companies has to lay off anybody. Okay. Atlassian has substantial free cashflow meta. I don't know. They're in the, their free cashflow is dip, but it's still like in the mid forties, right? They don't have to do this.”
Jason Lemkin Mar 19, 2026 ▶ 10:27 NVIDIA Predicts $1TRN in Revenue: Everything You Need to Know From GTC & Anduril Lands $20B Contract · 20VC with Harry Stebbings
Mar 19, 2026 bullish
Opinion
Lemkin: Tech startups were not overstaffed or bloated in 2021
“Everyone talks about how bloated teams got in 2021. I don't agree with that. I think they got as big as they needed to be when growth was high and you needed humans to do everything.”
Jason Lemkin Mar 19, 2026 ▶ 20:00 NVIDIA Predicts $1TRN in Revenue: Everything You Need to Know From GTC & Anduril Lands $20B Contract · 20VC with Harry Stebbings
Mar 19, 2026 positive
Insight
Lemkin: Top candidates must introduce one new AI tool monthly
“The answer in 2026 is what commercial AI tool have you brought into your organization this month? That's the test. Anyone that is on the bleeding edge that you would want to hire. Now there are so many great products in the market. Okay. There is no excuse in …”
Jason Lemkin Mar 19, 2026 ▶ 21:21 NVIDIA Predicts $1TRN in Revenue: Everything You Need to Know From GTC & Anduril Lands $20B Contract · 20VC with Harry Stebbings
Mar 19, 2026 bearish
Opinion
Lemkin: High gross retention does not guarantee future growth for Adobe
“Just because your GAR stays high, just because your nominal churn is low, does not mean you're going to grow. And I see no evidence Adobe will grow. I see no, no products that show they'll grow.”
Jason Lemkin Mar 19, 2026 ▶ 1:14:44 NVIDIA Predicts $1TRN in Revenue: Everything You Need to Know From GTC & Anduril Lands $20B Contract · 20VC with Harry Stebbings
Mar 19, 2026 bearish
Opinion
Lemkin refuses to invest in Travis Kalanick's new venture Atoms
“Would I invest based on the interview? No, I wouldn't.”
Jason Lemkin Mar 19, 2026 ▶ 1:02:13 NVIDIA Predicts $1TRN in Revenue: Everything You Need to Know From GTC & Anduril Lands $20B Contract · 20VC with Harry Stebbings
Mar 19, 2026 positive
Prediction Not checkable as stated
Lemkin: Winning with AI agents in Q2 2026 requires zero technical skill
“You do not need to be technical to win with AI agents in Q two of 26. You do not need to be even one percent technical.”
Jason Lemkin Mar 19, 2026 ▶ 29:44 NVIDIA Predicts $1TRN in Revenue: Everything You Need to Know From GTC & Anduril Lands $20B Contract · 20VC with Harry Stebbings
Mar 19, 2026 negative
Disclosure
Lemkin: Under 30% of startup executives are genuinely AI fluent
“Even of the best startups I've invested in, maybe 30% of the management team meets the standard at best. 30%, maybe less. And of the interviews I do in general, it's single digit percents.”
Jason Lemkin Mar 19, 2026 ▶ 18:51 NVIDIA Predicts $1TRN in Revenue: Everything You Need to Know From GTC & Anduril Lands $20B Contract · 20VC with Harry Stebbings
Mar 19, 2026 positive
What-if
Lemkin: Uber would be worth $1 trillion today under Travis Kalanick
“I think Travis Uber would be a trillion dollar company today because it would be five years ahead of where it is today.”
Jason Lemkin Mar 19, 2026 ▶ 0:21 NVIDIA Predicts $1TRN in Revenue: Everything You Need to Know From GTC & Anduril Lands $20B Contract · 20VC with Harry Stebbings
Mar 19, 2026 positive
Insight
Lemkin: Anyone who deployed enterprise software can deploy AI agents
“If in the last three to five years, you have successfully deployed a piece of enterprise software of any sort, you yourself, not some agency you hired, but if you have deployed it, you can deploy any agentic tool, any, and you can become the hero in your compa…”
Jason Lemkin Mar 19, 2026 ▶ 28:10 NVIDIA Predicts $1TRN in Revenue: Everything You Need to Know From GTC & Anduril Lands $20B Contract · 20VC with Harry Stebbings
Mar 19, 2026 bearish
Prediction Not checkable as stated
Lemkin: Existing SaaS and tech products will be obsolete in 12 months
“They, in 12 months, their current products will be obsolete.”
Jason Lemkin Mar 19, 2026 ▶ 13:32 NVIDIA Predicts $1TRN in Revenue: Everything You Need to Know From GTC & Anduril Lands $20B Contract · 20VC with Harry Stebbings
Mar 26, 2026 bearish
Disclosure
Lemkin: Refuses to buy Figma stock at $12B valuation
“No, I don't see any evidence of turning, of these agentic investments working. I would rather miss, miss out on the bounce right off the hard deck than invest in something that may fall below it.”
Jason Lemkin Mar 26, 2026 ▶ 53:18 Why You Need a $1B Fund To Do Series A | SpaceX at $2TRN & Data Centers in Space | Groq's $20BN Deal · 20VC with Harry Stebbings
Mar 26, 2026 bearish
Prediction Open · timeframe Mar 2031
Lemkin: Seed ownership will increasingly dilute to 3-4% at exit
“I think we're going to see more and more of those. Right. Dilution in time. We'll see more and more seed investments eroded to three, four percent.”
Jason Lemkin Mar 26, 2026 ▶ 1:05:34 Why You Need a $1B Fund To Do Series A | SpaceX at $2TRN & Data Centers in Space | Groq's $20BN Deal · 20VC with Harry Stebbings
Apr 2, 2026 neutral
Assertion Not checkable as stated
Lemkin: Y Combinator startup valuations jump 20% to 30% post-Demo Day
“It's been true of YC since I started investing. There was always a cheaper price before demo day. If you're reasonably hot, a higher price at demo day, and then a 20% or 30% after demo day.”
Jason Lemkin Apr 2, 2026 ▶ 41:20 OpenAI Kills Sora & Hits $100M ARR on Ads | Oura Going Public & Whoop Raises at $10BN · 20VC with Harry Stebbings
Apr 9, 2026 bearish
Disclosure
Lemkin: Portfolio company with $100M+ revenue faces severe AI competition
“For example, I'm a, I'm an investor in a company that's crossed nine figures in revenue, but it is hitting massive AI competition and issues.”
Jason Lemkin Apr 9, 2026 ▶ 1:11:07 OpenAI Buys TBPN & Their Management Team Reboot | Mercor Hack & Why Now is the Time for Cyber · 20VC with Harry Stebbings
Apr 9, 2026 bearish
Prediction Not checkable as stated
Lemkin: Most B2B Startups Will Suffer Worse Cybersecurity Breaches Than Mercor
“I genuinely think that most B to B companies are going to get hit worse than Merkur.”
Jason Lemkin Apr 9, 2026 ▶ 1:19:20 OpenAI Buys TBPN & Their Management Team Reboot | Mercor Hack & Why Now is the Time for Cyber · 20VC with Harry Stebbings
Apr 9, 2026 bearish
Prediction Not checkable as stated
Lemkin: Recent security breach could be fatal for AI startup Mercor
“I just don't see how you would come back from this. If you've crossed, there's just no, unless you have to, I think it's potentially death.”
Jason Lemkin Apr 9, 2026 ▶ 1:16:43 OpenAI Buys TBPN & Their Management Team Reboot | Mercor Hack & Why Now is the Time for Cyber · 20VC with Harry Stebbings
Apr 9, 2026 neutral
Assertion Not checkable as stated
Lemkin: Enterprise buyers historically gave software vendors one pass on security breaches
“In the old days, like through 20, 23 in our lifetimes, you always got to pass once as a vendor. Even for the worst breaches, the worst issues, unless your app was down for weeks, you'd get called into the CISO's office. You'd get yelled at. It was brutal, but …”
Jason Lemkin Apr 9, 2026 ▶ 1:16:51 OpenAI Buys TBPN & Their Management Team Reboot | Mercor Hack & Why Now is the Time for Cyber · 20VC with Harry Stebbings
Apr 9, 2026 neutral
Insight
Lemkin: Low-ACV AI startups must build 5 distinct products to hit $1B ARR
“The reality is you have to go truly multi-product earlier in this type of situation. Not, not just a little feature, right? Not just a little enhancement. But you literally probably have to build five distinct products to get to that billion and not you know, …”
Jason Lemkin Apr 9, 2026 ▶ 1:00:31 OpenAI Buys TBPN & Their Management Team Reboot | Mercor Hack & Why Now is the Time for Cyber · 20VC with Harry Stebbings
Apr 9, 2026 negative
Opinion
Lemkin: VCs are acting as pre-AI enablers instead of declaring code red
“I just see too many VCs running a pre AI enabler playbook. Where, where, where when folks do fall behind a tick or two, the, you see kumbaya activity instead of code red activity.”
Jason Lemkin Apr 9, 2026 ▶ 1:10:32 OpenAI Buys TBPN & Their Management Team Reboot | Mercor Hack & Why Now is the Time for Cyber · 20VC with Harry Stebbings
Apr 16, 2026 bearish
Prediction Not checkable as stated
Lemkin is ready to write off portfolio startups failing to adopt AI
“Like you know, I'm ready to move on to the new world and I'm almost, and I'm frankly ready to write off a lot of portfolio companies and a lot of public companies. It's time to move on guys. If you're not going to get there in April of 20, 26, then so be it. S…”
Jason Lemkin Apr 16, 2026 ▶ 16:15 SpaceX's Financials Leaked: Is it Worth $2TN | Meta Debuts Muse Spark: Are They Back in the AI Race? · 20VC with Harry Stebbings
Apr 16, 2026 bearish
Insight
Lemkin: Incumbent SaaS cannot monetize mediocre check-the-box AI agent features
“You checking the box does not work with agents. The check the box feature cannot be monetized in the AI era.”
Jason Lemkin Apr 16, 2026 ▶ 28:56 SpaceX's Financials Leaked: Is it Worth $2TN | Meta Debuts Muse Spark: Are They Back in the AI Race? · 20VC with Harry Stebbings
Apr 16, 2026 positive
Prediction Not checkable as stated
Jason Lemkin: Building AI agents will become accessible to everyone in 18 months
“Everyone in 18 months will figure out how to build an AA, because they'll get easier and easier to train.”
Jason Lemkin Apr 16, 2026 ▶ 1:09:41 SpaceX's Financials Leaked: Is it Worth $2TN | Meta Debuts Muse Spark: Are They Back in the AI Race? · 20VC with Harry Stebbings
Apr 16, 2026 negative
Opinion
Lemkin is burnt out on Anthropic CEO Dario Amodei crying wolf
“I don't buy Dario anymore. He may well be the second greatest founder of all time behind Elon, but I am just so burnt out of the boy who cries wolf.”
Jason Lemkin Apr 16, 2026 ▶ 0:00 SpaceX's Financials Leaked: Is it Worth $2TN | Meta Debuts Muse Spark: Are They Back in the AI Race? · 20VC with Harry Stebbings
Apr 16, 2026 bearish
Disclosure
Lemkin refuses to buy public SaaS stocks with sub-par AI solutions
“No, I wouldn't buy any of them. I wouldn't buy, because I'm looking for products that are more than a 60% solution.”
Jason Lemkin Apr 16, 2026 ▶ 33:16 SpaceX's Financials Leaked: Is it Worth $2TN | Meta Debuts Muse Spark: Are They Back in the AI Race? · 20VC with Harry Stebbings
Apr 23, 2026 bearish
Prediction Not checkable as stated
Lemkin: Claude Design will maim Figma's growth within 4 to 8 quarters
“Those both can be true that we won't see it in Figma's numbers next quarter. And that over four, six, eight quarters, it will maim its growth.”
Jason Lemkin Apr 23, 2026 ▶ 57:23 Cursor Acquired for $60BN | Anthropic Hits $1TRN in Secondary Markets & Figma, Adobe, Canva Dead? · 20VC with Harry Stebbings
Apr 23, 2026 bearish
Prediction Open · timeframe Apr 2031
Lemkin: Anthropic will never build direct Figma or Adobe competitors
“But I do not believe Anthropic will ever build a direct Figma or Illustrator or Adobe competitor. They don't have to maim them.”
Jason Lemkin Apr 23, 2026 ▶ 55:24 Cursor Acquired for $60BN | Anthropic Hits $1TRN in Secondary Markets & Figma, Adobe, Canva Dead? · 20VC with Harry Stebbings
Apr 23, 2026 bullish
Assertion Supported
Lemkin: Rippling reached $1B ARR while accelerating growth past 70%
“So if they were at less than 511 months ago, which I do know. Right. And they're at a billion growing 70 something percent. Do the math with me, Rory. They're accelerating. It's not just 70, which is enough. They're accelerating.”
Jason Lemkin Apr 23, 2026 ▶ 1:10:56 Cursor Acquired for $60BN | Anthropic Hits $1TRN in Secondary Markets & Figma, Adobe, Canva Dead? · 20VC with Harry Stebbings
Apr 30, 2026 bullish
Assertion Not checkable as stated
Lemkin: Agent benchmark ranked Anthropic ahead of OpenAI and Gemini
“In fact, the order is Anthropic. And so the greater it graded Anthropic just above OpenAI and then Gemini was just down here.”
Jason Lemkin Apr 30, 2026 ▶ 7:58 Anthropic Raises $45B but Falls Short on Compute & Thoma Bravo Hand Back Medallia Keys to Creditors · 20VC with Harry Stebbings
Apr 30, 2026 positive
Assertion Partly supported
Lemkin: Ryan Smith's Utah Jazz investment quadrupled, outpacing software returns
“When Ryan Smith sold Qualtrics, I think he made about a billion dollars. After 20 years or so and I believe that billion, most of it went back into the jazz, and it has quadrupled... He's up three billion on the jazz or something like that versus the 20 years …”
Jason Lemkin Apr 30, 2026 ▶ 1:15:38 Anthropic Raises $45B but Falls Short on Compute & Thoma Bravo Hand Back Medallia Keys to Creditors · 20VC with Harry Stebbings
Apr 30, 2026 bearish
Prediction Held up
Lemkin: AI agents render Marketo, Outreach, and Salesloft worthless
“They're not going to recommend Marketo for your agent to do marketing automation, ok? In fact, it mocked Marketo outreach and sales loft as tools useless to agents. Ok, this API grid. They said there is no place in the, an agent will never send an email throug…”
Jason Lemkin Apr 30, 2026 ▶ 7:26 Anthropic Raises $45B but Falls Short on Compute & Thoma Bravo Hand Back Medallia Keys to Creditors · 20VC with Harry Stebbings
Apr 30, 2026 negative
Disclosure
Lemkin: $100M+ startup reports three different ARR metrics monthly
“And for example, I've got one investment I made that's north of nine figures in revenue. I get three different ARR numbers each month. Three different definitions.”
Jason Lemkin Apr 30, 2026 ▶ 1:07:19 Anthropic Raises $45B but Falls Short on Compute & Thoma Bravo Hand Back Medallia Keys to Creditors · 20VC with Harry Stebbings
Apr 30, 2026 bullish
Assertion Not checkable as stated
Lemkin: Stripe received sole A+ grade in agentic API benchmark
“Over, over the weekend my nine nine six project was I built an agentic API grader where we went, I just had Claude, OpenAI, and Gemini together take the top 120 APIs and grade which ones they thought were the best, which tools I thought, 11 Labs everything on …”
Jason Lemkin Apr 30, 2026 ▶ 6:54 Anthropic Raises $45B but Falls Short on Compute & Thoma Bravo Hand Back Medallia Keys to Creditors · 20VC with Harry Stebbings
Apr 30, 2026 neutral
Disclosure
Lemkin: Salesforce bill jumped to $22,000 while seats dropped to three
“Our Salesforce bill went up from 12,000 to 22,000 dollars a year, and our seats went down from 10 to two plus one.”
Jason Lemkin Apr 30, 2026 ▶ 25:54 Anthropic Raises $45B but Falls Short on Compute & Thoma Bravo Hand Back Medallia Keys to Creditors · 20VC with Harry Stebbings
Apr 30, 2026 bearish
Opinion
Lemkin: Atlassian and Monday threatened as AI agents bypass project tools
“The public markets have the right idea, but the wrong direction. The public markets think vibe coding and Claude are their threat. No, the threat is what the agents pick. And actually, if you look at overall, the markets are, they almost get it right. They're …”
Jason Lemkin Apr 30, 2026 ▶ 9:00 Anthropic Raises $45B but Falls Short on Compute & Thoma Bravo Hand Back Medallia Keys to Creditors · 20VC with Harry Stebbings
May 7, 2026
Insight
Lemkin: VCs consistently overstate downside protection and the number of potential acquirers
“Downside protection is real. We just overstate it. Right. And the number of potential acquirers is real. We actually overstate that too.”
Jason Lemkin May 7, 2026 ▶ 1:18:48 Anthropic's Raise & What It Means for Potential IPO? Mag7: Google & Amazon Up, Meta & Microsoft Down · 20VC with Harry Stebbings
May 7, 2026 bullish
Prediction Not checkable as stated
Lemkin: Markets will soon laugh at the predicted 'SaaS apocalypse'
“But I think in a couple of years, we'll look back and we'll laugh at the SAS apocalypse and say, my God, the explosion of B to B applications were like nothing we've seen before.”
Jason Lemkin May 7, 2026 ▶ 27:38 Anthropic's Raise & What It Means for Potential IPO? Mag7: Google & Amazon Up, Meta & Microsoft Down · 20VC with Harry Stebbings
May 7, 2026
Disclosure
Lemkin: SaaStr spends $254 monthly on two full-time autonomous AI agents
“Two of them full-time, two full-time human equivalents, 254 dollars a month.”
Jason Lemkin May 7, 2026 ▶ 58:50 Anthropic's Raise & What It Means for Potential IPO? Mag7: Google & Amazon Up, Meta & Microsoft Down · 20VC with Harry Stebbings
May 7, 2026 bullish
Opinion
Lemkin: Tech is experiencing the greatest application boom in history
“There is an application boom. This is the greatest boom in application building in the history of our lives. The amount has exploded.”
Jason Lemkin May 7, 2026 ▶ 26:59 Anthropic's Raise & What It Means for Potential IPO? Mag7: Google & Amazon Up, Meta & Microsoft Down · 20VC with Harry Stebbings
May 7, 2026 negative
Opinion
Lemkin: AI has expanded the customer experience TAM by 50%, not 10x
“I'm not just a hundred percent convinced the CX market, as big as it is, four hundred billion, whatever you want to call it. I'm not convinced it's grown 10 X because of AI. I believe it's grown a bit. I believe it might've grown 50%.”
Jason Lemkin May 7, 2026 ▶ 1:11:38 Anthropic's Raise & What It Means for Potential IPO? Mag7: Google & Amazon Up, Meta & Microsoft Down · 20VC with Harry Stebbings
May 14, 2026 positive
Disclosure
Lemkin: Founders should accept buyouts unless they refuse $1 billion
“That's why I tell all founders to take the offer. I tell all founders to take it. The opposite of VCs, take it. It's, it is an intensity test. And if they push back and say, no, a billion is not enough. Great. Then go for it. But if they're not sure you may no…”
Jason Lemkin May 14, 2026 ▶ 1:16:22 Anthropic Buys Compute From Elon & Commits $200BN to Google | Cerebras IPO | Ramp Raises at $40BN · 20VC with Harry Stebbings
May 14, 2026 negative
Insight
Lemkin: Fireside chats and speakers are dead at tech conferences
“So I'll have to see, but we won't do, we'll never do Unless I'm forced to, I mean, if, you know, I do it for Sam Altman, but otherwise I'm not gonna do, there's, the firesides are dead and speakers are dead. There's just no point when podcasts are better.”
Jason Lemkin May 14, 2026 ▶ 1:06:02 Anthropic Buys Compute From Elon & Commits $200BN to Google | Cerebras IPO | Ramp Raises at $40BN · 20VC with Harry Stebbings
May 14, 2026 bearish
Assertion Not checkable as stated
Lemkin: Public markets fear terminal value is zero for decelerating SaaS
“But I think even though the SaaS apocalypse is behind us I think for many, there is still a worry, the terminal value is zero. I don't think that fear has gone away. If you're, if you keep decelerating, While budget is accelerating everywhere around you.”
Jason Lemkin May 14, 2026 ▶ 38:45 Anthropic Buys Compute From Elon & Commits $200BN to Google | Cerebras IPO | Ramp Raises at $40BN · 20VC with Harry Stebbings
May 14, 2026 negative
Opinion
Lemkin: Anthropic secondary sales restriction is an overblown social media non-issue
“To me, this story seems like a nothing burger made up on social media.”
Jason Lemkin May 14, 2026 ▶ 5:23 Anthropic Buys Compute From Elon & Commits $200BN to Google | Cerebras IPO | Ramp Raises at $40BN · 20VC with Harry Stebbings
May 14, 2026 negative
Insight
Lemkin: VCs never make real money investing in 'nice' founders
“Yeah, and every time you cut a corner, every time you invest in a founder that's really nice and really hardworking and really good guy, you never make any real money.”
Jason Lemkin May 14, 2026 ▶ 1:15:10 Anthropic Buys Compute From Elon & Commits $200BN to Google | Cerebras IPO | Ramp Raises at $40BN · 20VC with Harry Stebbings
May 21, 2026 bullish
Assertion Not checkable as stated
Lemkin: No Signs of an Impending Short-Term Market Crash
“We see no signs that there's a short-term crash coming.”
Jason Lemkin May 21, 2026 ▶ 42:10 Anthropic Raises $30BN at $900BN Price | SpaceX Files S1: How Does it Trade | Cerebras Smashes Day 1 · 20VC with Harry Stebbings
May 21, 2026
Prediction Not checkable as stated
Lemkin: Tech Leaders Must Hire Thousands to Avoid Social Unrest
“We're gonna have to reflate and hire thousands and thousands of people per tech leader to avoid social unrest.”
Jason Lemkin May 21, 2026 ▶ 0:56 Anthropic Raises $30BN at $900BN Price | SpaceX Files S1: How Does it Trade | Cerebras Smashes Day 1 · 20VC with Harry Stebbings
May 21, 2026 neutral
Disclosure
Lemkin: SaaStr spends $2k monthly on tokens across 21 AI agents
“At SAS for itself, Amelia and I have, now we have 21 agents of which three are autonomous, okay? And The direct token costs that we spend, the direct AI altogether for both of us is about two grand a month.”
Jason Lemkin May 21, 2026 ▶ 14:39 Anthropic Raises $30BN at $900BN Price | SpaceX Files S1: How Does it Trade | Cerebras Smashes Day 1 · 20VC with Harry Stebbings
May 28, 2026 bullish
Prediction Not checkable as stated
Lemkin: $2M Revenue Per Employee Is New Normal For Scaling Startups
“I think two million per employee is going to become the new normal as you scale. And that will mean that your high performers can make two to three times what they used to make, just like an anthropic because you just don't need as many people and you're going…”
Jason Lemkin May 28, 2026 ▶ 31:53 OpenAI & SpaceX S1 Drops | Layoffs at Cloudflare & ClickUp | OpenRouter & Polsia Raise Mega Rounds · 20VC with Harry Stebbings
May 28, 2026 bearish
Insight
Lemkin: In AI Venture, Seed Investing Is for Suckers
“And I just think this going back to seed is for suckers. Like you want to invest the hour it blows up. The minute it blows up, you want to get the DM and just wire the money in AI. That's the play.”
Jason Lemkin May 28, 2026 ▶ 1:14:23 OpenAI & SpaceX S1 Drops | Layoffs at Cloudflare & ClickUp | OpenRouter & Polsia Raise Mega Rounds · 20VC with Harry Stebbings
Jun 11, 2026 bearish
Prediction Didn’t hold up
Lemkin: SpaceX IPO will be a dud and will not trade up
“I think the IPO nominally will be a dud. I don't think it will trade up dramatically.”
Jason Lemkin Jun 11, 2026 ▶ 6:45 SpaceX Launches Largest Ever IPO | OpenAI Files to Go Public | Uber Cuts 23% of HR · 20VC with Harry Stebbings
Jun 11, 2026 bearish
Opinion
Lemkin: Skeptical of Suno's path to a $20 billion outcome
“You know, the rate at which that valuation doubled and you know, the twenty billion dollar outcome for it, I'm not smart enough to see it yet. So it feels a little bit to me like risk on, right?”
Jason Lemkin Jun 11, 2026 ▶ 56:12 SpaceX Launches Largest Ever IPO | OpenAI Files to Go Public | Uber Cuts 23% of HR · 20VC with Harry Stebbings
Jun 25, 2026 negative
Insight
Lemkin: LLM-driven migration tools are destroying traditional B2B software moats
“It's a moat destroyer when LLMs will lift you from one vendor to the other, and I, you know, I don't even, like, I literally was doing a pitch this week, and the founder was going on and on about their moats, and I immediately didn't want to invest. Like, I ju…”
Jason Lemkin Jun 25, 2026 ▶ 1:10:00 DeepSeek Raises at $50B | The Rise of Open Source vs OpenAI & Anthropic | OpenAI Builds Own Chip · 20VC with Harry Stebbings
Jun 25, 2026 bearish
Insight
Lemkin: Seat-based software companies are getting crushed by variable pricing models
“Everyone selling seats for the most part is getting crushed. Everyone selling variably one way or the other is winning.”
Jason Lemkin Jun 25, 2026 ▶ 1:08:08 DeepSeek Raises at $50B | The Rise of Open Source vs OpenAI & Anthropic | OpenAI Builds Own Chip · 20VC with Harry Stebbings
Jun 25, 2026 negative
Prediction Open · timeframe Jun 2031
Lemkin: Will only invest in startups working in-office six days weekly
“I want small high paid teams that work in the office over six days a week. That's I'm not interested in investing in anything else. I'm just not interested. And it's not because I don't have empathy. It's because they're gonna fail.”
Jason Lemkin Jun 25, 2026 ▶ 1:14:55 DeepSeek Raises at $50B | The Rise of Open Source vs OpenAI & Anthropic | OpenAI Builds Own Chip · 20VC with Harry Stebbings
Jul 2, 2026 negative
Opinion
Lemkin: Struggling non-AI CEOs post performative AI metrics on Twitter
“I am getting burnout on struggling CEOs on Twitter sharing performative AI data when they're not AI companies. Like, show me the money.”
Jason Lemkin Jul 2, 2026 ▶ 5:15 Coinbase Cuts AI Spend by 50% | Kalshi's $40B Valuation & Impending IPO | The Year for SaaS Roll-Ups · 20VC with Harry Stebbings
Jul 2, 2026 bearish
Disclosure
Lemkin refuses to invest in Chamath's 8090 without full-time commitment
“So I, I'm out. If literally Chamath drops everything, but 80, 90, everything. And I see the sweat from his brow and I see all, and I see that cause the dude's fit and he's looking good. Right. He just had, A massive, the massive largest win of his career as an…”
Jason Lemkin Jul 2, 2026 ▶ 1:01:04 Coinbase Cuts AI Spend by 50% | Kalshi's $40B Valuation & Impending IPO | The Year for SaaS Roll-Ups · 20VC with Harry Stebbings
Jul 2, 2026 bearish
Insight
Lemkin: Leaving oligopolies triggers massive price erosion in AI models
“When you leave oligopolical stages, there's massive price erosion because you're no longer competing on features, you're competing on price, and that's exactly what we're seeing.”
Jason Lemkin Jul 2, 2026 ▶ 31:49 Coinbase Cuts AI Spend by 50% | Kalshi's $40B Valuation & Impending IPO | The Year for SaaS Roll-Ups · 20VC with Harry Stebbings
Jul 2, 2026 negative
Disclosure
Lemkin: Investments in multi-project founders yielded zero financial returns
“I've written small checks into successful founders doing multiple things just for fun, and they're all zeros.”
Jason Lemkin Jul 2, 2026 ▶ 1:00:44 Coinbase Cuts AI Spend by 50% | Kalshi's $40B Valuation & Impending IPO | The Year for SaaS Roll-Ups · 20VC with Harry Stebbings
Jul 2, 2026 positive
Assertion Supported
Lemkin: AI features helped Box return to double-digit growth
“It has led to a boost at Box. It hasn't turned Box into a hundred percent grower. It's gotten it back to double digit growths.”
Jason Lemkin Jul 2, 2026 ▶ 16:12 Coinbase Cuts AI Spend by 50% | Kalshi's $40B Valuation & Impending IPO | The Year for SaaS Roll-Ups · 20VC with Harry Stebbings
Jul 2, 2026 bearish
Opinion
Lemkin: Asana product feels terminal and fits roll-up target criteria
“This is easy for me to, I don't want to be too much of an armchair quarterback from a product that feels terminal, but it's probably a good one. I think it's a good candidate, right?”
Jason Lemkin Jul 2, 2026 ▶ 57:44 Coinbase Cuts AI Spend by 50% | Kalshi's $40B Valuation & Impending IPO | The Year for SaaS Roll-Ups · 20VC with Harry Stebbings
Jul 9, 2026
Insight
Lemkin: Tech workers should only join startups with 24-month tender visibility
“Why is a, why would you join anything that you don't have high certainty, not just they're going to be a unicorn because it's not good enough, that they're going to have tender offers, right, in the next 24 months.”
Jason Lemkin Jul 9, 2026 ▶ 1:23:55 Enterprises Fear Frontier Models | Sam Altman Offers Trump 5% of OpenAI | DeepSeek Builds Own Chips · 20VC with Harry Stebbings
Jul 9, 2026 negative
Opinion
Lemkin: Founders No Longer Care About Making Late-Stage Investors Money
“No one's worried about making their last round high-priced investors money anymore. Literally no one is.”
Jason Lemkin Jul 9, 2026 ▶ 25:27 Enterprises Fear Frontier Models | Sam Altman Offers Trump 5% of OpenAI | DeepSeek Builds Own Chips · 20VC with Harry Stebbings
Jul 9, 2026 positive
Insight
Lemkin: Selling 5% Equity to Corporate Partners Creates Disproportionate Alignment
“What I've learned from my portfolio and I think you guys will agree is it creates an out an unexpectedly large amount of alignment. You get, you sell five percent of your company to a hundred billion dollar partner. It don't matter to Rory's point. It just don…”
Jason Lemkin Jul 9, 2026 ▶ 7:53 Enterprises Fear Frontier Models | Sam Altman Offers Trump 5% of OpenAI | DeepSeek Builds Own Chips · 20VC with Harry Stebbings
Jul 9, 2026 positive
Assertion Partly supported
Lemkin: OpenAI and Anthropic have eliminated equity vesting cliffs
“Well, now that they're, now that there aren't even vesting schedules at Open Ananthropic, those issues have been solved. Right? A lot of startups don't have vesting schedules for top employees, right? It doesn't mean you vest into all your stock, right? Sorry,…”
Jason Lemkin Jul 9, 2026 ▶ 1:25:54 Enterprises Fear Frontier Models | Sam Altman Offers Trump 5% of OpenAI | DeepSeek Builds Own Chips · 20VC with Harry Stebbings
Jul 16, 2026 negative
Opinion
Lemkin: GoDaddy relies on tricking customers into unwanted add-on purchases
“I don't think GoDaddy could exist if it hadn't perfected getting you to stick stuff when you buy a domain name you never knew.”
Jason Lemkin Jul 16, 2026 ▶ 56:55 Zuckerberg Back on X Challenging Codex & Claude Code | SK Hynix’s $26BN IPO · 20VC with Harry Stebbings
Jul 16, 2026 negative
Assertion Not checkable as stated
Lemkin: Faking affiliate attribution is standard practice across startups
“Doing basically what everyone in your industry does, doing scammy affiliate marketing when it's basically part of your thing. I mean, startups cut corners, right? It's not, this isn't Delvesque, but everyone cuts a corner. When everyone in your industry is sli…”
Jason Lemkin Jul 16, 2026 ▶ 55:59 Zuckerberg Back on X Challenging Codex & Claude Code | SK Hynix’s $26BN IPO · 20VC with Harry Stebbings
Jul 16, 2026 bearish
Prediction Not checkable as stated
Lemkin: More Stalled SaaS Unicorns Will Be Wiped Out By Debt
“There's going to be a lot more of these stories coming in the coming years.”
Jason Lemkin Jul 16, 2026 ▶ 1:15:07 Zuckerberg Back on X Challenging Codex & Claude Code | SK Hynix’s $26BN IPO · 20VC with Harry Stebbings
Jul 16, 2026 negative
Insight
Lemkin: Startups with talent momentum shouldn't announce hot funding rounds
“The most in my career today, there are the most reasons to not announce, if you can get away with it, to not announce a hot round. Right. If you've already got enough, if you've already got enough going on to attract talent, right, for recruiting especially if…”
Jason Lemkin Jul 16, 2026 ▶ 1:08:53 Zuckerberg Back on X Challenging Codex & Claude Code | SK Hynix’s $26BN IPO · 20VC with Harry Stebbings
Jul 16, 2026
Insight
Lemkin: Multi-billion funds raise seed valuations to meet 20% ownership targets
“If you see an S tier team, and it's in the right space, and you want to hit your number, your 20% ownership, and your fund is in billions, the math just makes sense. It's a bet. It's just a bet.”
Jason Lemkin Jul 16, 2026 ▶ 1:04:08 Zuckerberg Back on X Challenging Codex & Claude Code | SK Hynix’s $26BN IPO · 20VC with Harry Stebbings
Jul 16, 2026 neutral
Prediction Not checkable as stated
Lemkin: Enterprise budget caps will force adoption of cheaper AI models
“As every organization goes from burn all the tokens you want, baby, to budgets, However you do it, whether it's automated, whether it's manual, whether it's picking a dropdown, everyone's going to have to have a cheaper model.”
Jason Lemkin Jul 16, 2026 ▶ 14:15 Zuckerberg Back on X Challenging Codex & Claude Code | SK Hynix’s $26BN IPO · 20VC with Harry Stebbings
Jul 16, 2026 bearish
Insight
Lemkin: Stalled $70M ARR SaaS companies are now worth only 1x revenue
“It's a clean look of what's eight percent, six percent growth with deteriorating market share at seventy million ARR, where you're not reigning cash worth, it's worth one X.”
Jason Lemkin Jul 16, 2026 ▶ 1:16:00 Zuckerberg Back on X Challenging Codex & Claude Code | SK Hynix’s $26BN IPO · 20VC with Harry Stebbings
Jul 16, 2026 negative
Insight
Lemkin: Raising venture debt instead of equity is a sucker bet
“Certainly don't do debt instead of an equity round. That's the sucker bet, right? It's just, you better be the hottest thing on planet earth or it's gonna kill you.”
Jason Lemkin Jul 16, 2026 ▶ 1:15:15 Zuckerberg Back on X Challenging Codex & Claude Code | SK Hynix’s $26BN IPO · 20VC with Harry Stebbings
Jul 23, 2026
Insight
Lemkin: Founders shouldn't reject major buyout offers unless 10x upside exists
“I think for a founder, when you start to get into nosebleed offers in absolute terms, it has to be 10 X to go for it. It's not worth it for three X. It is not.”
Jason Lemkin Jul 23, 2026 ▶ 26:00 Should the US Ban Chinese Open-Source Models | OpenRouter's Chance To Sell | Stripe Buying PayPal
Jul 23, 2026 negative
Insight
Lemkin: Series B VCs now need seed-level picking skills to survive
“I think the real pressure is, it means anything below that growth stage, you better be a damn good picker. Because it used to be when Rory and I met, Series B, even into Series A, you actually didn't have to be a good picker. You just had to be good at math an…”
Jason Lemkin Jul 23, 2026 ▶ 1:07:45 Should the US Ban Chinese Open-Source Models | OpenRouter's Chance To Sell | Stripe Buying PayPal
Jul 23, 2026
Insight
Lemkin: Ideal startup sale timing is right before market recognizes commoditization
“And the perfect outcome is to sell the moment it becomes commoditized, but before everyone fully realizes it, that's when they'll give you the money, but that's before the value decrease rather than it creates in it.”
Jason Lemkin Jul 23, 2026 ▶ 30:32 Should the US Ban Chinese Open-Source Models | OpenRouter's Chance To Sell | Stripe Buying PayPal
Jul 29, 2026 bearish
Assertion Not checkable as stated
Lemkin: Founders quitting solid startups for shiny trends always regret it
“Most of the founders I've worked with over my career that have done that, that have quit something pretty good to do the shiny penny they're not all Ilya. They've all, it's all been a net negative. All, all the times I've seen it, the ones that quit with somet…”
Jason Lemkin Jul 29, 2026 ▶ 1:05:15 Jensen's Open-Weights Letter | Google Cloud Grows 82% But The Market Tanks
Jul 29, 2026 negative
Disclosure
Lemkin: Churned from Marketo after price jumped from $22K to $80K
“We just turned off Marketo. They raised our prices from 22,000 to 80,000 dollars since 2020. We left.”
Jason Lemkin Jul 29, 2026 ▶ 59:44 Jensen's Open-Weights Letter | Google Cloud Grows 82% But The Market Tanks
Jul 29, 2026 negative
Opinion
Lemkin: Stripe offers acceptable but mediocre acquisition prices to VC startups
“I've been on the other side of Stripe deals. They do what you would expect. They offer an acceptable but mediocre price from a venture perspective, right?”
Jason Lemkin Jul 29, 2026 ▶ 1:14:28 Jensen's Open-Weights Letter | Google Cloud Grows 82% But The Market Tanks
Jul 29, 2026 positive
Assertion Partly supported
Lemkin: I have never returned less than 5x to my investors
“I've never made my investors less than five X.”
Jason Lemkin Jul 29, 2026 ▶ 1:09:36 Jensen's Open-Weights Letter | Google Cloud Grows 82% But The Market Tanks
Aug 12, 2026 bearish
Disclosure
Lemkin's team churned off Canva and Notion due to AI agents
“My, me having churned, and Amelia having churned, we churned just not because, this is a tough one, Canva and Notion, both we churned, not because they're not great apps, we just no longer had any need for them in the agentic area, just no need. Canva and Noti…”
Jason Lemkin Aug 12, 2026 ▶ 4:33 Canva Slashes Growth | Talent Exodus at Google | Revolut's $50B CEO Package | Musk's $55B Terrafab
Aug 12, 2026 neutral
Disclosure
Lemkin's lifetime exits split evenly on holding versus taking early secondaries
“And I literally just did this analysis across my whole lifetime of all the things I've been involved with, personal, angel, venture, who should have sold, and who should have sold early or taken than secondary. And for me, it broke roughly fifty-fifty.”
Jason Lemkin Aug 12, 2026 ▶ 32:30 Canva Slashes Growth | Talent Exodus at Google | Revolut's $50B CEO Package | Musk's $55B Terrafab
Aug 12, 2026 negative
Disclosure
Seed models must assume 75% dilution and 4x effective entry prices
“When I started, my model was I'm actually paying twice my entry price. That's how I model. Now it's four X. Now I'm playing, now I'm paying, I'm going to suffer 75% dilution, and it's not, and that really means my entry price is four X what it looks like on, b…”
Jason Lemkin Aug 12, 2026 ▶ 1:12:58 Canva Slashes Growth | Talent Exodus at Google | Revolut's $50B CEO Package | Musk's $55B Terrafab
Aug 12, 2026 bearish
Prediction Not checkable as stated
Any startup investment not run by a founder will be a zero
“Any investment I've made that is not run by a founder is a zero. It's going to be a zero in this age. It's going to be a zero. I look across, now you, we have different portfolios, but the ones I have that are not run by founders, whether they're at twenty mil…”
Jason Lemkin Aug 12, 2026 ▶ 1:09:24 Canva Slashes Growth | Talent Exodus at Google | Revolut's $50B CEO Package | Musk's $55B Terrafab
Aug 12, 2026 negative
Opinion
Vibe coding a custom CRM makes no sense for most companies
“This makes no sense for 99.9% of the world, ok? You can't maintain it, you can't build the integrations, it's more complicated. Most of the folks that say that have never used a CRM”
Jason Lemkin Aug 12, 2026 ▶ 28:41 Canva Slashes Growth | Talent Exodus at Google | Revolut's $50B CEO Package | Musk's $55B Terrafab
Aug 12, 2026 bearish
Opinion
Canva is currently worth only $12 billion in public market value
“I'd say it's probably worth twelve billion right now. 20% growth at four billion ARR in the current public markets and not decelerating. There's some sort of rule of 40 number that's better, but I'd say it's worth about twelve billion.”
Jason Lemkin Aug 12, 2026 ▶ 25:28 Canva Slashes Growth | Talent Exodus at Google | Revolut's $50B CEO Package | Musk's $55B Terrafab
Aug 20, 2026 positive
Disclosure
Lemkin: SaaStr runs Salesforce headless using an internal AI revenue agent
“So we run Salesforce entirely headless. Yeah. Okay. So we have our own agent, our own AI VP of revenue. It runs Salesforce under the hood. Pro is it makes Salesforce much more powerful than it ever was. Like I didn't log into Salesforce for seven years. Now I …”
Jason Lemkin Aug 20, 2026 ▶ 58:13 Stripe's $8B OpenRouter Bet | Anthropic's First Profit & The Math Behind Reaching $600B in Revenue?
Aug 27, 2026 bullish
Prediction Not checkable as stated
Lemkin: Workers Will Threaten to Quit Without Continuous AI Agents
“Next year, there's going to be backlash. I can see it in my best portfolio companies where we can't go back anymore. We can't live. We can't go back in time. And I need my 10 sub agents running 24 hours a day to do my job or I quit.”
Jason Lemkin Aug 27, 2026 ▶ 58:44 Anthropic's $30T Assumption & OpenAI Confirms IPO | Why Customer Service & Robotics are Overinflated
Aug 27, 2026 bearish
Opinion
Lemkin: VC funding accounting and law firms will not produce tech-scale outcomes
“I just don't believe you can throw a bunch of venture money into accounting firms or law firms. And magically turn them into the next Mercur or hugging face or any of these things.”
Jason Lemkin Aug 27, 2026 ▶ 1:24:05 Anthropic's $30T Assumption & OpenAI Confirms IPO | Why Customer Service & Robotics are Overinflated
Aug 27, 2026 bearish
Prediction Not checkable as stated
Lemkin: Classic CS and CX software won't exist in 24 months
“Classic CS and CX won't even exist in 24 months. There's really no, there'll be commodity cheap products But we won't even need it. It's already dying and merging into marketing, sales, every, everything's becoming one agent.”
Jason Lemkin Aug 27, 2026 ▶ 1:23:32 Anthropic's $30T Assumption & OpenAI Confirms IPO | Why Customer Service & Robotics are Overinflated
Sep 3, 2026 bearish
Prediction Not checkable as stated
Most European Point-Solution Startups Will Fail in the US Market
“And that's why your European startups, most of them are going to fail at least in the U S because they can't do much more with more, right? They're going to fail. Their little point solutions are just going to disappear in six months. We don't need those littl…”
Jason Lemkin Sep 3, 2026 ▶ 52:22 NVIDIA Crushes Quarter | OpenAI Cuts Off Cursor | Instinct Hits $2.5B Valuation
Sep 3, 2026 bullish
Assertion Supported
Restaurant AI Platform Owner Raised Capital at $2.3B Valuation
“I remember last week I was at a board meeting for owner, which just raised at 2.3 billion, right? It's sort of a next gen, next dish generation, AI infused restaurant platform.”
Jason Lemkin Sep 3, 2026 ▶ 45:30 NVIDIA Crushes Quarter | OpenAI Cuts Off Cursor | Instinct Hits $2.5B Valuation
Sep 3, 2026 neutral
Assertion Supported
Lemkin: Founders Fund previously cut its fund size due to deployment constraints
“Founders fund cut their, you know, N minus two funds ago, they cut them because they couldn't think they could deploy enough fund in the, in that window.”
Jason Lemkin Sep 3, 2026 ▶ 53:19 NVIDIA Crushes Quarter | OpenAI Cuts Off Cursor | Instinct Hits $2.5B Valuation
Sep 10, 2026 bullish
Opinion
Lemkin: Fable 5.1 is a step function comparable to an S-tier CTO
“Fable five for me was that for just for me was that step function where all of a sudden we could solve big problems together the way you'd like to with like your best CTO, like if you've ever worked with a five out of five or like an S tier CTO where you could…”
Jason Lemkin Sep 10, 2026 ▶ 27:12 Jensen Huang Declares AGI Has Arrived | Tesla Launches Cybercabs | Index Pulls Out of Town
Sep 10, 2026 bullish
Disclosure
Lemkin discloses his team runs Replit 20 hours a day
“Even for me, and again, I know folks sometimes mock me, but the biggest change for our little tiny team of two and a half humans is we run Replit between me and Amelia. We run it 20 hours a day now.”
Jason Lemkin Sep 10, 2026 ▶ 19:08 Jensen Huang Declares AGI Has Arrived | Tesla Launches Cybercabs | Index Pulls Out of Town
Sep 10, 2026 negative
Opinion
Lemkin: CEO AI benchmarks on X are essentially worthless
“And you look on X and all the CEOs are sharing their benchmarks, which are essentially worthless, right? There's no cost or time in them and it's all performative AI, like vibe coding your own CRM.”
Jason Lemkin Sep 10, 2026 ▶ 25:23 Jensen Huang Declares AGI Has Arrived | Tesla Launches Cybercabs | Index Pulls Out of Town
Sep 10, 2026 bearish
Disclosure
Lemkin: Passing on Instinct at a $2.5B valuation
“The last round was two and a half, Jason. Jason Lemkin: I know. That's why we're going to have to pass on the round.”
Jason Lemkin Sep 10, 2026 ▶ 7:08 Jensen Huang Declares AGI Has Arrived | Tesla Launches Cybercabs | Index Pulls Out of Town
Sep 10, 2026 positive
Disclosure
Lemkin: I sold my car and rely solely on Waymo and Uber Black
“In the Bay Area, I got rid of my car, so I only do Waymo and autonomous driving. Yeah. I don't drive. I'm done with it. if there is an issue, I take a Uber black, but I don't have a car anymore in the bear. I just don't have one.”
Jason Lemkin Sep 10, 2026 ▶ 44:33 Jensen Huang Declares AGI Has Arrived | Tesla Launches Cybercabs | Index Pulls Out of Town
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