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20VC Opinion
Lemkin: Benchmark's flat partnership model is optimized for profit, not discipline
“This is one of these things we manufacture, like how wonderful it is. Benchmark has a flat partnership. I mean, who cares, right? It's not disciplined. It's optimized to make the most money.”
Jason Lemkin Jul 16, 2026 ▶ 1:23:29 Zuckerberg Back on X Challenging Codex & Claude Code | SK Hynix’s $26BN IPO · 20VC with Harry Stebbings
20VC Opinion
Lemkin: when a late $100M check can 10x, why did I bother getting in early
“And when everything can exit north of twenty billion, you know, it's I, even me, like I have an investment with a hundred million dollar position that took me years and years and years to get to right now. And then just watching a growth round where someone co…”
Jason Lemkin Jul 16, 2026 ▶ 43:05 Zuckerberg Back on X Challenging Codex & Claude Code | SK Hynix’s $26BN IPO · 20VC with Harry Stebbings
20VC Assertion Supported
Lemkin: OpenAI and Anthropic Lied About Books and YouTube Training Data
“Open AI, an anthropic, Kind of lied about the books, and they definitely lied about training on YouTube”
Jason Lemkin Jul 9, 2026 ▶ 31:42 Enterprises Fear Frontier Models | Sam Altman Offers Trump 5% of OpenAI | DeepSeek Builds Own Chips · 20VC with Harry Stebbings
20VC Prediction Not checkable as stated
Lemkin: Microsoft's enterprise AI deployment strategy will fail
“I think this is going to fail because I don't think there is enough talent To do what we want to do in the enterprise. The idea makes sense to on a spreadsheet. It makes sense. Sad is smarter than me, but I, my today, my experience is it's going to fail with a…”
Jason Lemkin Jul 9, 2026 ▶ 1:07:56 Enterprises Fear Frontier Models | Sam Altman Offers Trump 5% of OpenAI | DeepSeek Builds Own Chips · 20VC with Harry Stebbings
20VC Opinion
Lemkin: round-trip revenue is suddenly cool again, so everyone will do it everywhere
“I love it. Now that round trip revenue is like totally cool and not something you go to jail for, like, let's, let's do it every single place we can find it, right? Let's just do it. And I'm not saying there's anything literally wrong with it, but go for it, r…”
Jason Lemkin Jul 9, 2026 ▶ 42:55 Enterprises Fear Frontier Models | Sam Altman Offers Trump 5% of OpenAI | DeepSeek Builds Own Chips · 20VC with Harry Stebbings
SAASTR Opinion
Lemkin: The job market for average computer science graduates has been devastated
“There's no need for the most part, for a B tier. B level grade CS engineer. It's been devastated, right?”
Jason Lemkin Jul 8, 2026 ▶ 35:16 Agents Didn't Kill Sales. They Just Exposed It with SaaStrAI CEO and Founder Jason Lemkin
SAASTR Assertion Supported
Lemkin: Cerebras is going public at $40B with two Middle Eastern customers
“Like Cerebus is going public, I think today at like a forty billion dollar market cap. It has some interesting customers, but basically it only has two customers today in the Middle East that you've never heard of.”
Jason Lemkin Jul 8, 2026 ▶ 44:55 Agents Didn't Kill Sales. They Just Exposed It with SaaStrAI CEO and Founder Jason Lemkin
20VC 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
20VC 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
20VC Insight
Lemkin: Autonomous AI agents could reduce Salesforce and HubSpot to dumb databases
“If the agent can run 24 seven autonomously, take all your data and build all the analytics, build all the dashboards, run autonomously out of it then your data can flow between apps and you won't even care where it lives and all the fears about headless become…”
Jason Lemkin Jul 2, 2026 ▶ 1:12:27 Coinbase Cuts AI Spend by 50% | Kalshi's $40B Valuation & Impending IPO | The Year for SaaS Roll-Ups · 20VC with Harry Stebbings
20VC Opinion
Lemkin: Modern open-source AI is fake because China subsidizes training costs
“Open source is a bit of a fake because China's paying for all the trading, okay? It's not open source like a generation ago.”
Jason Lemkin Jun 25, 2026 ▶ 0:00 DeepSeek Raises at $50B | The Rise of Open Source vs OpenAI & Anthropic | OpenAI Builds Own Chip · 20VC with Harry Stebbings
20VC Assertion Supported
Lemkin: OpenAI and Anthropic yield 40-70% gross margins on enterprise inference
“They have an enterprise base, which is, it has, you know, between 40 and 70% in, you know, gross margin just on inference.”
Jason Lemkin Jun 25, 2026 ▶ 36:08 DeepSeek Raises at $50B | The Rise of Open Source vs OpenAI & Anthropic | OpenAI Builds Own Chip · 20VC with Harry Stebbings
20VC Assertion Partly supported
Lemkin: Prompt engineering skills that once paid $150,000 are now worthless
“When we started this show, you need to be a fucking prompt it. They would joke this was the highest paying job out of college was prompt engineers were making a 150,000 dollars out of college because they knew how to write a prompt. That skill's worthless toda…”
Jason Lemkin Jun 25, 2026 ▶ 48:06 DeepSeek Raises at $50B | The Rise of Open Source vs OpenAI & Anthropic | OpenAI Builds Own Chip · 20VC with Harry Stebbings
20VC 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
SAASTR Prediction Not checkable as stated
Lemkin: A Generation of Operations Roles Will Never Be Hired
“I mean, for us there, so there'll be a whole generation of these people that are just never hired. There may be some folks that are laid off. I, and I think more commonly they'll just be slowly managed out and just replaced with agents.”
Jason Lemkin Jun 16, 2026 ▶ 46:14 Our Agent Negotiated a Vendor Renewal, Became a CFO and a Better SDR .. but has too many guardrails
20VC Opinion
Lemkin: Uber Leaders Are Justified in Hating Benchmark Capital
“I think the folks that hate benchmark from Uber, I think they deserve to hate benchmark.”
Jason Lemkin Jun 11, 2026 ▶ 33:25 SpaceX Launches Largest Ever IPO | OpenAI Files to Go Public | Uber Cuts 23% of HR · 20VC with Harry Stebbings
SAASTR Prediction Not checkable as stated
Lemkin: Idle Capacity Will Be the Biggest Issue With AI Agents
“The biggest issue we're going to have going forward is our agents are going to get so good. They sit idle all day long. They don't have enough work.”
Jason Lemkin Jun 11, 2026 ▶ 3:48 $4 Trillion in IPOs, $100B in M&A, and Why B2B Spend is Booming
SAASTR Disclosure
Lemkin: SaaStr Replaced $500K in Staff With $257 in AI Agents
“We replaced 500,000 dollars worth of employees with 257 dollars worth of agents, but the productivity is higher.”
Jason Lemkin Jun 11, 2026 ▶ 9:57 $4 Trillion in IPOs, $100B in M&A, and Why B2B Spend is Booming
SAASTR Prediction Not checkable as stated
Lemkin: Companies Will Abandon Employee AI Reskilling by Year-End
“To be direct, I think by the end of this year, we're going to give up on reskilling. I think folks are going to stop pretending they can reskill folks that are not going to be able to make the jump to the agentic age.”
Jason Lemkin Jun 11, 2026 ▶ 10:22 $4 Trillion in IPOs, $100B in M&A, and Why B2B Spend is Booming
SAASTR Insight
Lemkin: Customers Prefer High-Performing AI to Mediocre Human Account Managers
“Customers will prefer, prefer a great eye to a mediocre human. They'll prefer a great eye that solves their problem today, that knows the answer, to someone that has to get an engineer and an appointment to you next week, that doesn't know, that says I'm just …”
Jason Lemkin Jun 11, 2026 ▶ 25:55 $4 Trillion in IPOs, $100B in M&A, and Why B2B Spend is Booming
SAASTR Disclosure
Lemkin: SaaStr wants to hire a human reporting to its AI agent
“We want to hire a human. To report to our AI VP of marketing.”
Jason Lemkin Jun 9, 2026 ▶ 28:31 What Agents That Actually Work Look Like Right Now with Replit's CEO and Founder
20VC Prediction Not checkable as stated
Calacanis: Companies will choose spending on AI tokens over humans by year-end
“I really do think by the end of the year, we're going to choose tokens over humans.”
Jason Lemkin Jun 4, 2026 ▶ 42:33 Anthropic Files to Go Public | Cognition Raises $1BN at $26BN Valuation | The 996 Work Ethic · 20VC with Harry Stebbings
20VC Prediction Open · timeframe Jan 2027
Calacanis: Software QA departments will be destroyed by 2027 due to AI
“I think what will happen going into 2027 is an engineering QA departments will get destroyed because you'll be like, I got six QA engineers.”
Jason Lemkin Jun 4, 2026 ▶ 44:39 Anthropic Files to Go Public | Cognition Raises $1BN at $26BN Valuation | The 996 Work Ethic · 20VC with Harry Stebbings
20VC Prediction Not checkable as stated
Calacanis: AI Startups Will Eventually Re-Bloat to Historic Headcounts
“And so even, and so our startups that we're excited about, I think ultimately they will achieve the same historic level of bloat, maybe half the size, but they will get as bloated as they can because they will have much larger, broader product lines.”
Jason Lemkin Jun 4, 2026 ▶ 58:55 Anthropic Files to Go Public | Cognition Raises $1BN at $26BN Valuation | The 996 Work Ethic · 20VC with Harry Stebbings
20VC Opinion
Lemkin: High-Flyer AI Valuations Are 'SolarCity on Steroids'
“It's solar city on steroids, and we're all here for it because we love AI, but it makes no sense.”
Jason Lemkin May 28, 2026 ▶ 53:11 OpenAI & SpaceX S1 Drops | Layoffs at Cloudflare & ClickUp | OpenRouter & Polsia Raise Mega Rounds · 20VC with Harry Stebbings
20VC Opinion
Lemkin: Blaming Tech Layoffs on COVID Overhiring Is Mathematically False
“I'm saying there is already more natural attrition since Twenty-twenty than these numbers. So blaming it directly on overhiring is clickbait. It's clickbait because it's not mathematically true.”
Jason Lemkin May 28, 2026 ▶ 25:05 OpenAI & SpaceX S1 Drops | Layoffs at Cloudflare & ClickUp | OpenRouter & Polsia Raise Mega Rounds · 20VC with Harry Stebbings
20VC Opinion
Lemkin: CoreWeave and Nebius Have No Special Technology
“I mean, Corweave has nothing. What do Nebius and Corweave have? Nothing, no special technology, right?”
Jason Lemkin May 28, 2026 ▶ 59:52 OpenAI & SpaceX S1 Drops | Layoffs at Cloudflare & ClickUp | OpenRouter & Polsia Raise Mega Rounds · 20VC with Harry Stebbings
20VC 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
20VC 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
20VC Opinion
Lemkin: Figma lost $500M+ failing to launch design-to-code natively
“What Figma missed is I create this design. It's beautiful. I loop in the product team to approve it. And then I click a button, which it says push into full production prototype. And it just works. It works like, and you can, and the irony is Replit and Lovabl…”
Jason Lemkin May 21, 2026 ▶ 26:48 Anthropic Raises $30BN at $900BN Price | SpaceX Files S1: How Does it Trade | Cerebras Smashes Day 1 · 20VC with Harry Stebbings
20VC Prediction Not checkable as stated
Lemkin: Current tech layoffs will be worse than any in our lifetimes
“I actually think It's worse than that Rory, because I think these are going to be by far the layoffs that Harry just rattled off and the ones for this year, I believe are going to be far worse than any layoffs in our lifetimes. And I'll tell you why. And I kno…”
Jason Lemkin May 21, 2026 ▶ 1:25:31 Anthropic Raises $30BN at $900BN Price | SpaceX Files S1: How Does it Trade | Cerebras Smashes Day 1 · 20VC with Harry Stebbings
20VC Prediction Open · timeframe May 2027
Lemkin: Traditional marketing automation software obsolete within one year
“I don't think in a year we're going to need any traditional marketing automation software. It's too dated. It doesn't work for agents marketing.”
Jason Lemkin May 14, 2026 ▶ 35:09 Anthropic Buys Compute From Elon & Commits $200BN to Google | Cerebras IPO | Ramp Raises at $40BN · 20VC with Harry Stebbings
20VC 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
20VC 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
20VC 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
SAASTR Disclosure
Lemkin: SaaStr no longer needs junior marketers due to AI agent
“Is it a partial replacement for junior marketers? Yeah, we don't need any.”
Jason Lemkin May 12, 2026 ▶ 17:40 Our AI is Hiring! Would You Work for One? And Are Autonomous Agents ... Safe? The Agents #005
20VC Insight
Lemkin: Modern CMOs should run marketing campaigns directly using AI agents
“A CMO today should be able to run their own campaigns, and this is why. I'm not saying you have to spin up Marketo or HubSpot. I'm saying you should be able to tell your agent, and our agent, our AIVP marketing started running its own campaigns the last two we…”
Jason Lemkin May 7, 2026 ▶ 1:32:07 Anthropic's Raise & What It Means for Potential IPO? Mag7: Google & Amazon Up, Meta & Microsoft Down · 20VC with Harry Stebbings
SAASTR Opinion
Lemkin: Pre-AI B2B SaaS companies are becoming "tragedy apps"
“And it just, I think most of the old SAS companies, the pre AIB to be players have become tragedy apps.”
Jason Lemkin May 6, 2026 ▶ 34:31 Why Your Next Hire Should Report to an AI, Tragedy Apps, and Too Many AI SDRs? | The Agents #004
20VC Opinion
Lemkin: Anthropic's Claude holds no competitive advantage for most workflows
“As workflows expand to do everything, as agents do more, they will pick the LLM, and I see no competitive advantage to Claude for most workflows.”
Jason Lemkin Apr 30, 2026 ▶ 4:21 Anthropic Raises $45B but Falls Short on Compute & Thoma Bravo Hand Back Medallia Keys to Creditors · 20VC with Harry Stebbings
20VC 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
20VC Assertion Not checkable as stated
Lemkin: Coupa, Zendesk, and Anaplan may fail to repay their debt
“Coupa, New Relic, Anaplan, even Zendesk, Avalara, Smartsheet they all look like they may not be able to fully repay their debt”
Jason Lemkin Apr 30, 2026 ▶ 47:05 Anthropic Raises $45B but Falls Short on Compute & Thoma Bravo Hand Back Medallia Keys to Creditors · 20VC with Harry Stebbings
20VC Prediction Not checkable as stated
Lemkin: Blocked SaaS founders will increasingly pass company control to peer CEOs
“This is a micro trend that I think is going to accelerate this year is founders giving the keys to their friends, not completely quitting, like eight months after an accelerator that didn't work out, but I mean, it's just, I'm at 40,000,050 1,000,020 million, …”
Jason Lemkin Apr 30, 2026 ▶ 58:37 Anthropic Raises $45B but Falls Short on Compute & Thoma Bravo Hand Back Medallia Keys to Creditors · 20VC with Harry Stebbings
20VC Opinion
Lemkin: Most pre-AI CEOs cannot handle AI-era operational demands
“Cause I think most CEOs I work with are not up for it is the truth. Cause most pre AI CEOs are not, they're not up. You guys know this too, from your portfolio, not all, but most are not actually up for the massive amount of, what's more than nine, nine, six, …”
Jason Lemkin Apr 23, 2026 ▶ 36:31 Cursor Acquired for $60BN | Anthropic Hits $1TRN in Secondary Markets & Figma, Adobe, Canva Dead? · 20VC with Harry Stebbings
SAASTR Opinion
Lemkin: Figma feels like 'grandpa software' despite top-decile revenue growth
“This is why now Figma feels like grandpa software. That's the thing. It feels like grandpa software. It feels like grandpa software and you don't, the NRR is still high. The company is still growing at top decile rates, but who wants to buy new stuff from gran…”
Jason Lemkin Apr 22, 2026 ▶ 19:58 Managing 20+ AI Agents: Lazy Agents, Our $500K AI Bill, Stealth Churn & the Death of 60% Solutions
SAASTR Opinion
Lemkin: Clerk Is 'Mind-Numbingly Hard to Use' and Most Frustrating App
“Probably the most frustrating app I've used is clerk, right? For authentication on replica. It's just. Mind-numbingly hard to use.”
Jason Lemkin Apr 22, 2026 ▶ 46:13 Managing 20+ AI Agents: Lazy Agents, Our $500K AI Bill, Stealth Churn & the Death of 60% Solutions
20VC 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
20VC Opinion
Lemkin: Dario Amodei is the second-greatest founder behind Elon Musk
“What I mean is listen, he may well be the second greatest founder of all time behind Elon. Look what he's done in five years, right? Five years to thirty billion, the grit, the greatest grudge startup of all time.”
Jason Lemkin Apr 16, 2026 ▶ 7:51 SpaceX's Financials Leaked: Is it Worth $2TN | Meta Debuts Muse Spark: Are They Back in the AI Race? · 20VC with Harry Stebbings
20VC 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
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