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Opinion
Stebbings: 20VC hires mostly immigrants because British people lack strong work ethic
“Pretty much only hire immigrants. British people don't work very hard.”
Harry Stebbings Jul 20, 2026 ▶ 1:19:57 The Open-Source AI Reality | How Token Costs Will Fall 10X & Usage Will Explode 100X | Lin Qiao
Prediction Open · timeframe Feb 2029
Stebbings: 20VC will not invest in per-seat software pricing models
“If they sell per seat, we're not doing it. We need to replace jobs. Like labor displacement is what we're investing into. And that's the only way that we can actually return the amount of money that we need to now to make funds worth it.”
Harry Stebbings Feb 16, 2026 ▶ 19:06 Klarna CEO: SaaS is Dead: Why Systems of Record Will Die in an Agentic World · 20VC with Harry Stebbings
Disclosure
Harry Stebbings: Sweet spot for hiring is under-24 Asians and Eastern Europeans
“So I hire, bluntly, Asians or Eastern Europeans, and very young, sub-twenty-three, 24. That is a sweet spot for us.”
Harry Stebbings Jan 9, 2026 ▶ 11:48 20Sales: Why the Best Sales People are F**** in the Head | Why Remote Work is BS | Why Europe is a Nightmare for Recruiting Sales Teams | How to Build a Sales Machine | What Everyone Gets Wrong Today in Sales with Chad Peets
Disclosure
Stebbings: 20VC hires candidates with extreme trauma or extreme masochism
“For us, I look for people who have either extreme trauma or extreme masochism.”
Harry Stebbings Aug 18, 2025 ▶ 3:24 Lovable CEO, Anton Osika: The State of Foundation Models, Grok vs OpenAI, and Replit vs Bolt · 20VC with Harry Stebbings
Assertion Not checkable as stated
Stebbings: Two VC funds carried the same startup at $800M vs $10.2B
“I was looking at one today and one was valued at eight hundred million and the other person had it at 10.2 billion.”
Harry Stebbings Mar 25, 2024 ▶ 1:06:36 David Clark: Lessons from 32 Years of Fund Investing - Why Exits Will Be Larger | E1131 · 20VC with Harry Stebbings
Assertion Not checkable as stated
Higher Founder NPS Inversely Correlates With VC DPI Returns
“There is an inverse correlation between the NPS of the manager and the DPI provided. Most often, the higher the NPS, the lower the DPI, and vice versa.”
Harry Stebbings Oct 20, 2023 ▶ 9:23 20VC: NEW FORMAT: Harry Stebbings on Why Seed Pricing is as High as Ever, Why Series A is the Best Place to Invest Today, Why Growth Founders Need to Reshape Expectations, Why M&A Windows Remain Shut and When Will IPO Windows Crack Open
Assertion Not checkable as stated
Stebbings: High-valuation pre-seed rounds by former VPs are my worst investments
“But like, my worst performing, and I've done a 150 investments now, the worst performing ones are always the stellar VP that comes out of the stellar company and raises 10 on 40 as the pre-seed. They are always the ones which slowly meander to either a bad hac…”
Harry Stebbings Sep 6, 2023 ▶ 11:54 Nikhil Basu Trivedi: Why 99% of AI Investments Will Go Bust | E1057 · 20VC with Harry Stebbings
Insight
Stebbings: Market dynamics matter more than founder quality in startup success
“I lost money recently because I invested in a company And the founder was world class. Fantastic founder. But in a market that, hell or high water, you could not make money, and then the business was no longer able to exist. And I learned, actually, market win…”
Harry Stebbings Sep 12, 2022 ▶ 25:25 Will Quist: Why 95% of Venture Capital is Not Really “Venture Capital” | 20VC #924 · 20VC with Harry Stebbings
Disclosure
Stebbings: 20VC Lost Hundreds of Millions Passing on Deel Over Ownership Targets
“I look at ours, and our biggest mistake, and I can look at Deal, 11 Labs, I can look at Granola, and Starcloud, Fractile, could have done them all, but would have had one to two percent, and all of them we turned down purely for ownership, and that is hundreds…”
Harry Stebbings Aug 7, 2026 ▶ 28:56 The AI Boom Will Create Enormous Roadkill: Who Wins & Loses? | David Frankel
Assertion Not checkable as stated
Stebbings: 90% of young founders pitch traits he publicly values
“I would say nine out of 10 young founders that we meet pitch those three exactly, and you're like, wow, this is very aligned.”
Harry Stebbings May 18, 2026 ▶ 13:36 Turning Peter Thiel's $100K into $10M Angel Portfolio & Why VCs Can Be Sharks | Josh Browder · 20VC with Harry Stebbings
Disclosure
Stebbings: 20VC's biggest regret was not playing momentum in hot AI rounds
“My biggest regret with our Series A fund is not being more elastic, disregarding the Series A mandate, and just saying I'm going to leverage the brand and the access that I have, arrogantly, forgive me for that, to get into super hot companies like your 11 Lab…”
Harry Stebbings Mar 26, 2026 ▶ 1:15:27 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
Disclosure
Stebbings: 20VC lost seed deal to mega fund's $100M valuation offer
“We lost a deal recently to a large mega fund, and we did three on 15, and they did 10 on a hundred with no lick pref pre-anything.”
Harry Stebbings Feb 23, 2026 ▶ 37:24 Insights from Coatue's Growth Investor Lucas Swisher · 20VC with Harry Stebbings
Opinion
Stebbings: Proprietary Media Distribution Drives 20VC Fund Outperformance
“Well, this is why our venture funds are doing so well right now, which is because everyone has a venture capital fund today, sadly, but not everyone has distribution.”
Harry Stebbings Jan 24, 2026 ▶ 17:17 20VC: Raising $400M for 20VC: Fundraising Lessons | Getting Marc Benioff Through 53 Cold Emails: How to Master Cold Outbound | 7 Lessons from 101 Decacorn Founders with Harry Stebbings (Simon Squibb Edition)
Insight
Stebbings: Hires Family and Friends to Bypass Work-Life Balance Trade-Offs
“My business partner always tells me very correctly, life is like a cooker in a kitchen. There's four hobs, you know, that you turn on. There's family, there's friends, there's work, and there's fitness, ok? Family, friends, work, and fitness. And the trouble i…”
Harry Stebbings Jan 24, 2026 ▶ 32:38 20VC: Raising $400M for 20VC: Fundraising Lessons | Getting Marc Benioff Through 53 Cold Emails: How to Master Cold Outbound | 7 Lessons from 101 Decacorn Founders with Harry Stebbings (Simon Squibb Edition)
Disclosure
Stebbings: 20VC portfolio company will surpass Superhuman's 8-year revenue in 9 months
“We are in a company that is similar to superhuman that will be at More than their revenue in nine months for what it took them eight years to go to.”
Harry Stebbings Jul 3, 2025 ▶ 54:04 Figma’s IPO: The Full Breakdown & Why Melio’s $2.5BN Acquisition is “Discouraging” · 20VC with Harry Stebbings
Disclosure
Stebbings: 20VC lost a $5M ARR Series A deal valued at $600M
“We lost to Series A, actually last 10 days, and it was doing five million in ARR and it was, yeah, started at like, two, twenty-five million ended up at 600.”
Harry Stebbings Jul 3, 2025 ▶ 1:11:48 Figma’s IPO: The Full Breakdown & Why Melio’s $2.5BN Acquisition is “Discouraging” · 20VC with Harry Stebbings
Disclosure
Stebbings: Lost seed deal to $8M on $100M uncapped offer
“I did three on 15. Handshake was the founder. It was pre-product, pre-revenue, pre-everything, but amazing founder. And he called me up and said, I would never walk out on a handshake. But I got offered eight on a hundred, and it's uncapped.”
Harry Stebbings Mar 26, 2025 ▶ 55:10 Mitchell Green, Founder @ Lead Edge Capital: Why Traditional VC is Broken · 20VC with Harry Stebbings
Prediction Not checkable as stated
Lemkin: VCs will regret low ownership stakes over the next decade
“I think the other hubris that a whole generation of folks on 20 VC and otherwise are, we're all gonna slowly regret over the next decade. And it's tough one to solve is just these low ownership stakes.”
Jason Lemkin May 27, 2024 ▶ 1:04:16 Jason Lemkin: Why Pricing is Worse Than Ever and There is More Funding Than Ever | E1157 · 20VC with Harry Stebbings
Insight
Stebbings: Early investors should take secondary liquidity when valuations peak
“Actually, regardless of how well the company's doing, regardless of trajectory, who's joining rounds, if you are in early enough, and the prices get high enough, just take some off the table. And actually be much more active around it. Like, you know, be a rea…”
Harry Stebbings Nov 15, 2023 ▶ 1:30:37 Des Traynor: How to Survive and Thrive in a World of OpenAI | E1082 · 20VC with Harry Stebbings
Assertion Not checkable as stated
Exit Timing Yields 3x Return Spread on Identical VC Positions
“Proprietary 20 VC data shows managers with the same positions, but three X different returns due to timing and size of exiting a position.”
Harry Stebbings Oct 20, 2023 ▶ 10:37 20VC: NEW FORMAT: Harry Stebbings on Why Seed Pricing is as High as Ever, Why Series A is the Best Place to Invest Today, Why Growth Founders Need to Reshape Expectations, Why M&A Windows Remain Shut and When Will IPO Windows Crack Open
Disclosure
Stebbings: 20VC has shifted into a purely competitive fund model
“Truth is, and it's the hard truth and it's the ugly truth. We are just competitive now. We have to build a better product that competes with these firms.”
Harry Stebbings Aug 23, 2023 ▶ 1:02:45 Jason Lemkin & Rick Zullo: How "Mark to Market" Corrupted Venture Capital | E1052 · 20VC with Harry Stebbings
Disclosure
20VC enforces a three-hour WhatsApp response rule to drive urgency
“It's three hours long. Everyone should be able to go to a cinema with their families. But if you were asked a question on what's apps like, You need to respond within three fucking hours. It drives efficiency and urgency.”
Harry Stebbings May 16, 2026 ▶ 51:07 The Five Year Desert to Product Market Fit & a $5.3BN Valuation with Shiv Rao, Founder @ Abridge · 20VC with Harry Stebbings
Disclosure
Stebbings: Lovable's ARR jumped from $3M to $20M during Series A legals
“When we did Lovables A, it was like at three million in revenue. By the time the legals were done, it was at 20. And so the multiple had gone from 70 x to 10 x.”
Harry Stebbings Feb 23, 2026 ▶ 9:39 Insights from Coatue's Growth Investor Lucas Swisher · 20VC with Harry Stebbings
Assertion Not checkable as stated
Stebbings: Raised 20VC Capital via WhatsApp Between Gym Sets
“When we fundraise, we raise from very rich individuals, we raise from, you know, institutions, and I would, in between sets in the gym, walk around in my two-minute breaks, and I would message individuals, this was, and say, hey, I'm going out to raise the new…”
Harry Stebbings Jan 24, 2026 ▶ 8:15 20VC: Raising $400M for 20VC: Fundraising Lessons | Getting Marc Benioff Through 53 Cold Emails: How to Master Cold Outbound | 7 Lessons from 101 Decacorn Founders with Harry Stebbings (Simon Squibb Edition)
Assertion Not checkable as stated
Stebbings: SaaS Startup Needed 120 Meetings for One Term Sheet Despite 10x Growth
“We had a company that went from 400 K to three million Naira, classic enterprise SaaS business, bread and butter enterprise SaaS that would have had five term sheets from five good firms, 120 meetings, one term sheet and it was ten million round on a 40 post.”
Harry Stebbings Nov 13, 2025 ▶ 59:38 Michael Burry Shorts NVIDIA and Palantir & Has Defensibility Died in a World of AI? · 20VC with Harry Stebbings
What-if
Stebbings: 20VC missed ElevenLabs' seed round by rushing for efficiency
“It was 250 K at twenty five million. We're a big fund. It's like one percent, but I should have done it and I would have done it if I'd spent more time on it and I hadn't tried to focus on efficiency and clock speed.”
Harry Stebbings Sep 19, 2025 ▶ 42:01 20VC: Why 90% of Founders Build Startups Wrong | Why AI Growth Rates are Sustainable & Remote Work is BS and the AI Talent War | Competing with Brett Taylor and Sierra: Who Wins the Customer Service War with Jesse Zhang, Decagon
Assertion Not checkable as stated
Harry Stebbings: 20VC's $2M-$3M high-valuation 'Yolo' fund pool is up 7x
“Do you know, the funny thing is we have a like Yolo segment of our fund, which is like, yeah, which is a tiny pool of cash, whatever, like two million or three million, whatever. But it's basically, we have amazing access because of the shows and people will g…”
Harry Stebbings Aug 14, 2025 ▶ 34:52 Sam Altman's Masterplan or a Gift to Anthropic? Palantir & Shopify Crush Earnings · 20VC with Harry Stebbings
Disclosure
Stebbings: 20VC German AI startup grew from $200k to $1M in weeks
“We just did one in Germany peak when we did it. Two, 200 K when we did it is now at a million, like three weeks, but fucking nuts. The customer adoption that one of the fastest polls that I've seen in terms of consumer demand or customer demand,”
Harry Stebbings Jul 17, 2025 ▶ 48:20 Windsurf x Google x Cognition: Full Breakdown: Who Made Money, Who Did Not · 20VC with Harry Stebbings
Disclosure
Stebbings: 20VC Has Three Companies Scaling $0-100M ARR in One Year
“We have three companies that have gone from zero to a hundred million there in a year.”
Harry Stebbings Jun 30, 2025 ▶ 20:48 KKR's Head of European PE, Philipp Freise: Do Andreessen & General Catalyst Scare KKR? · 20VC with Harry Stebbings
Disclosure
Stebbings: 20VC Invested in Lovable at a 10x Revenue Multiple
“When we did Lovable, I think it trebled its revenue by the time the round had completed, and I was like, I would want to retrade on price. Like, it literally was only a 10 X revenue multiple when we did it.”
Harry Stebbings May 23, 2025 ▶ 57:58 20VC: ElevenLabs Head of Growth on Why You Do Not Need PMs | The 7-Part Launch Playbook That Gets 700K+ Views Per Product | The Truth About CAC, Payback & Performance Marketing in AI with Luke Harries
Disclosure
Stebbings: $5M checks at $25M valuations were 20VC Fund 1's worst performers
“The worst performing segment of our seed portfolio on our farm one was five on 25, because they had too much money too soon, there was a lack of focus, a lack of urgency, and actually they struggled to raise their next round because it was already at too high …”
Harry Stebbings Nov 20, 2024 ▶ 29:22 Cem Sertoglu: Lessons from the Greatest Venture Investment in European History | E1228 · 20VC with Harry Stebbings
Disclosure
Stebbings: 20VC's worst investments raised $5M on $25M valuations
“My worst performing companies are the five on 25 or bigger.”
Harry Stebbings Jul 15, 2024 ▶ 29:51 Saam Motamedi: Why Series B Won’t Make Money & Why $1M ARR is a BS Milestone for Series A | E1177 · 20VC with Harry Stebbings
Disclosure
Stebbings: My demanding leadership style created a culture of fear
“I'm very demanding. And do you know what it's led to? Honestly, ARA has created a culture of fear. People are like genuinely scared, which I don't want.”
Harry Stebbings Jul 10, 2024 ▶ 36:42 Ara Mahdessian: ServiceTitan Would Not Be the Success if We Raised VC Earlier | E1175 · 20VC with Harry Stebbings
Disclosure
Stebbings: 20VC holds a $60M stake in a $3B foundation model startup
“I was laughing with our CFO this morning, because we've got a company where we did the first round for when it was a SaaS company, pivoted to a foundation model, and now it's worth three billion. You can't get fucking liquidity on it, Jason. So like, we own tw…”
Harry Stebbings Jun 3, 2024 ▶ 43:19 Jason Lemkin: PluralSight S*** the Bed & The Next IPO Candidates | E1160 · 20VC with Harry Stebbings
Disclosure
Stebbings: Pay job candidates for a one-week stealth trial before hiring
“I always think, actually in most roles, it's about a week, which is why I try and pay people to take a week off their job beforehand. I say, hey Matt, it's a big decision for you. Let's pay you for a week, join for a week in, in kind of quiet, and we'll see if…”
Harry Stebbings May 31, 2024 ▶ 44:34 Matt Lerner: How to Hire Growth Leaders and Teams and Why in a World of AI | E1159 · 20VC with Harry Stebbings
Assertion Not publicly verifiable
Stebbings: 20VC Entry Prices Are 43% Lower Than 18 Months Ago
“When we compare our entry price now versus 18 months ago, it's 43% lower. And, like, of the last nine companies we've done, that is held true.”
Harry Stebbings Jan 29, 2024 ▶ 25:02 Ryan Akkina: How MIT Builds Their Venture Fund Portfolio & How MIT Approach Direct Investing | E1109 · 20VC with Harry Stebbings
Disclosure
20VC spends $25,000 per month on short-form video content
“We spend 25,000 dollars a month on short form video.”
Harry Stebbings Jan 19, 2024 ▶ 32:24 Zaria Parvez: How Duolingo Scaled to 8M TikTok Followers & How to Create Viral Content | E1105 · 20VC with Harry Stebbings
Disclosure
Stebbings: No 20VC portfolio companies will run out of cash in 2024
“I don't have any companies running out of cash this year. I think the closest one to running out of cash is 18 months. Everyone's just kicking it down the road, so I don't think this is the year of mortality, and I push back strongly.”
Harry Stebbings Jan 10, 2024 ▶ 9:59 Ed Sim & Jamin Ball: Did Figma Kill M&A Markets & 3 Requirements to IPO in 2024 | E1101 · 20VC with Harry Stebbings
Opinion
Stebbings: Celebrating wins creates complacency while 20VC remains behind competitors
“I find wins quite uncomfortable. I don't want everyone to get complacent. We haven't won shit. We're still behind other people in media and funds.”
Harry Stebbings Dec 11, 2023 ▶ 13:44 Sam Corcos: Why Founders Should Take as Many VC Meetings as Possible | E1093 · 20VC with Harry Stebbings
Insight
Stebbings: Candidates staying 1.5–2 years only deliver six months of actual work
“I hate bouncers, I call them, which is, as you said a couple of times, five, six jobs. I'm like, if you're somewhere for a year and a half, and another for two years, and another for a year and a half, with ramp time and leaving time, You basically did six mon…”
Harry Stebbings Nov 20, 2023 ▶ 56:48 Matteo Franceschetti: The Ultimate Hiring Playbook: Five Questions to Ask Every New Hire | E1084 · 20VC with Harry Stebbings
Disclosure
Stebbings: All 20VC Portfolio Companies Work Five Days In-Office
“All my companies, five days a week.”
Harry Stebbings Nov 6, 2023 ▶ 37:41 Joey Zwillinger: From $4.1BN to $142M Market Cap;Why Public Markets Have Written Allbirds Off |E1078 · 20VC with Harry Stebbings
Disclosure
Harry Stebbings opposes his employees having outside side projects or activities
“Yeah. Yeah, I would actually.”
Harry Stebbings Nov 3, 2023 ▶ 38:09 Roundtable #5 with Jack Altman, Auren Hoffman, Jason Lemkin, Harry Stebbings | E1077 · 20VC with Harry Stebbings
Assertion Not checkable as stated
2021 12-Month Deployment Funds Paid 41% Higher Entry Prices
“For those that deployed funds in 12 months in twenty-twenty-one, their average entry price is 41% higher than those that deployed over a three-year period.”
Harry Stebbings Oct 20, 2023 ▶ 9:54 20VC: NEW FORMAT: Harry Stebbings on Why Seed Pricing is as High as Ever, Why Series A is the Best Place to Invest Today, Why Growth Founders Need to Reshape Expectations, Why M&A Windows Remain Shut and When Will IPO Windows Crack Open
Disclosure
Stebbings: Implemented a mandatory five-day in-office requirement for all employees
“I actually made it five days a week for everyone in this, in our companies, and actually, it's so much better.”
Harry Stebbings Sep 4, 2023 ▶ 51:49 Mudassir Sheikha: The Meeting that Led to $3.1BN Buyout: The Battle Between Uber and Careem | E1056 · 20VC with Harry Stebbings
Opinion
Stebbings: Winning at modern content is purely a game of volume
“Volume is everything today. It is purely a game of output. You need YouTube shorts, you need Instagram reels, you need TikToks, you need podcast episodes, you need blog posts, you need Twitter threads, you need to be everywhere because attention is currency, a…”
Harry Stebbings Aug 14, 2023 ▶ 43:16 Tim Urban: How "Wait But Why" Grew to 600k Readers; AI's Revolutionary Impact on Media | E1048 · 20VC with Harry Stebbings
Insight
Stebbings: Follow-on investing fails because early winner prediction is impossible
“I think follow on is actually just an inherently hard strategy, because it assumes that you can essentially predict your winners so much sooner than I think you actually can.”
Harry Stebbings Jul 17, 2023 ▶ 9:35 Sheel Mohnot: How I Got Married in the Metaverse; Founder vs Product vs Market | E1035 · 20VC with Harry Stebbings
Assertion Not checkable as stated
Harry Stebbings: Six founding team members left 20VC portfolio companies in one month
“From our portfolios, which are quite broad and diverse now we've had six founding people from founding teams leave in the last month.”
Harry Stebbings Jun 5, 2023 ▶ 10:56 TJ Parker: Building PillPack, The First E-Commerce Pharmacy, to Amazon's $1B Acquisition | E1022 · 20VC with Harry Stebbings
Disclosure
Stebbings: 20VC $50k checks are brand-only and come with minimal time
“I've written 50 K checks from my fund, and I say very clearly, I'm just going to be honest, this is like a brand check, and use my name, but time wise, you chose that, not the 500 K offering, and so you don't have as much of my time.”
Harry Stebbings May 29, 2023 ▶ 53:29 Adam Besnivick: How to Invest in Pre-Seed & Seed Stage Companies; Looking Glass Capital | E1020 · 20VC with Harry Stebbings
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