The Ledger

Every statement that passed quotation and attribution checks. Mix any filter with any other: certainty 1/5, debate potential 5/5, or both at once.

clear all ✕

why aren't all 395 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 0 checkable ones are still open, waiting for their date. predictions held up or didn't; assertions are supported or contradicted. on every card: ▮▮▮▮▮ certainty · ▮▮▮▮▮ debate potential. speakers are clickable

What-if
Twitter would not exist as a company without co-founder Evan Williams
“Evan basically made the company what it is. Without Evan, there would be no Twitter as a company.”
George Zachary Oct 12, 2020 ▶ 33:40 20VC: CRV's George Zachary on His Relationship To Money and How it has Changed Over Time, Why The Best Founders Have Often Experienced Parental or Home Instability and The Stories Behind Investing in Unicorns; PillPack, Yammer and Udacity
What-if
Parse sold to Facebook too early and would have survived independently
“Yeah, we sold early. I think we had a lot of momentum, something great going. One thing I think people don't realize is the venture market actually really didn't appreciate the type of thing we were doing in the same way that it appreciates it now. You look at…”
Ilya Sukhar Sep 9, 2019 ▶ 28:35 20VC: Matrix's Ilya Sukhar on How The Seed Ecosystem Could Be Optimised, Why The Bar For The Break-Out Series A Has Risen & The Art of Effective Referencing
What-if
Gurley: Benchmark should have accepted Google's $100M valuation offer
“So I had a meeting or my firm benchmark had a meeting with Larry and Sergey where they said, will you invest at a hundred pre? And we should have said, yes, I would tell myself that.”
Bill Gurley Jun 24, 2019 ▶ 28:42 20VC: Benchmark's Bill Gurley on 5 Traits Benchmark Look For When Adding To The Partnership, Why The Abundance of Capital Is Today's Biggest Challenge in VC & The Right Way To Think About Market Size When Assessing Opportunities
What-if
Destin: Requiring Proven Unit Economics Would Have Killed Deliveroo and PillPack
“We would never have funded Deliveroo. We would never have funded PillPack. You know, in fact, Kareem probably would never have taken in any capital because you have to project yourself into sometimes a three or four year cycle before these unit economics reall…”
Fred Destin Jan 15, 2019 ▶ 7:50 20VC: Stride's Fred Destin on The Acceptable vs Non-Acceptable Risks When Investing, How Startup Founders Can Improve The Quality of Their Decision-Making and Must Play for Batting Average & Why Plans Do Not Matter and No Board Member Should Bash An Entre
What-if
Sanwal: VC funding would have locked CB Insights into 1000x smaller TAM
“And I think if we were not revenue funded, we'd have not seen that opportunity. I'm pretty sure that we'd have raised a bunch of money. We'd have burned time and effort on that. It's ultimately a total addressable market. For that first segment of dealmakers, …”
Anand Sanwal Dec 7, 2018 ▶ 8:28 20VC: CB Insights' Anand Sanwal on The Most Dangerous Myth Some Investors Have Promoted, Why Most B2B Content Is Crap and How To Make It Successful & Why Predigree Is Overrated and The Right Way To Scale Teams
What-if
Danny Rimer: Nasty Gal Could Have Succeeded With Co-Investor Board Support
“And I often think that what I should have done was share the workload with Someone else who's super competent and who would have been really helpful in the journey, because there were a lot of reasons why nasty gal could have been a phenomenal investment, but …”
Danny Rimer Dec 3, 2018 ▶ 33:04 20VC: Index's Danny Rimer on His Biggest Lessons On Price, Ownership, Board Dynamics & Building Consumer Businesses from Backing The Likes of King, Skype, Farfetch, Glossier and more...
What-if
Leore Avidar regrets raising venture capital because Lob could self-fund
“And so for Lobb, I mean, I wish I hadn't raised money because we keep doing well and we're able to self-fund through sales.”
Leore Avidar Mar 9, 2018 ▶ 12:33 20VC: 2 Levers To Fundraising: FOMO & Leverage and How To Use Them, How To Implement "A Sustainable Growth Mindset" & How To Put VCs To Work For You with Leore Avidar @ Lob
What-if
Gross: Airbnb likely would not exist without Michael Seibel and YC
“It is less likely that Airbnb would have been created had Michael Seibel not recruited the founders to Y Combinator, introduced them to Paul Graham, the program had been set up in place, the investment been available, demo day being available”
Daniel Gross Aug 21, 2017 ▶ 17:32 20VC: YC's Daniel Gross on How YC Can Democratise AI & Reduce Incumbency Advantages, Why ML Enabled Software Will Eat The Software That Ate The World & Whether AI Will Produce Independent Companies or Be Technology within Incumbents
What-if
Hamid: VCs Return More by Holding Winners for Decades
“And in many cases, you don't even want to distribute in those eight years because think about how much you would have made if you would have stayed in, in, in Amazon or Facebook or Google over the course of time it probably would have been much better for thos…”
Mamoon Hamid Oct 31, 2016 ▶ 8:14 20VC: Social Capital's Mamoon Hamid on Disrupting The Venture Model & Advancing Humanity By Solving The World's Toughest Problems
What-if
Cohen: Techstars returns would be 5x lower if using uncapped notes
“Had all the investments we've done been uncapped notes, it's something like a five X, you know, lower return.”
David Cohen Jun 27, 2016 ▶ 15:39 20VC: Techstars Founder, David Cohen on Scaling Techstars Ventures and Investing In Uber, Twilio and Sendgrid
What-if
Mah: inDinero would be half as successful if she had self-funded
“This is incredibly valuable, I believe, and I'm a hundred percent certain my business would not be half as well off if I had the money just sitting right there ready for me.”
Jessica Mah Jun 3, 2016 ▶ 8:34 20VC: inDinero's Jessica Mah on Why Angel Money Is Better Than Institutional Money and Boards Should Work For Founders
What-if
Following on in every Uber round wouldn't double Founder Collective's returns
“If we had invested in every single round we still wouldn't, I don't think, come close to doubling what our current value is.”
Eric Paley Nov 18, 2015 ▶ 18:05 20 VC 089: Eric Paley @ Founder Collective on Outliers, Inspirational Founders and Pro Rata
What-if
Beim: Gilt Groupe could not have succeeded equally on the West Coast
“Having vested in guilt when it was just three people, I can promise you could not have built that company to the same degree of success in the West Coast, because, you know, all of the fashion brands are in New York, all of the great merchandising talent, desi…”
Nick Beim Aug 19, 2015 ▶ 22:24 20 VC 064: Finding Exceptional People with Big Ideas with Nick Beim, Partner @ Venrock
What-if
Frankel: Following On in Every Round Boosts Absolute Returns, Not Multiples
“If we follow, our view would be we'd had, we would have had to have followed on in everything, and I think that the absolute return would be better. I don't think that the multiple would necessarily be better on the fund.”
David Frankel Aug 7, 2026 ▶ 33:32 The AI Boom Will Create Enormous Roadkill: Who Wins & Loses? | David Frankel
What-if
Fred Turner: Curative Could Not Have Been Built In The UK
“No, definitely not.”
Fred Turner Jul 18, 2026 ▶ 5:10 We Built Our Own Salesforce in Months. Here's Why We're Cancelling the $600K Contract | Curative CEO
What-if
O'Driscoll: Anthropic could not have been founded in Massachusetts due to non-competes
“I wonder if Anthropa could have been started in Massachusetts. Probably not, right? No, you're exactly right.”
Rory O'Driscoll Jul 16, 2026 ▶ 7:17 Zuckerberg Back on X Challenging Codex & Claude Code | SK Hynix’s $26BN IPO · 20VC with Harry Stebbings
What-if
Grinberg: Nuclear power would have given Europe an AI energy advantage
“In Europe, I mean, it's a, it's tough. I think that there were some, there was some good positioning that Europe had, you know, a few years ago, a few decades ago with nuclear that I think hasn't been, you know, delivered on as much as of late, but that would …”
Matan Grinberg Jun 13, 2026 ▶ 1:12:38 OpenAI vs Anthropic vs Open-Source | Token Maxing, AI Hangovers & The Coming ROI Reckoning · 20VC with Harry Stebbings
What-if
Laqua: High-ambition founders would have been military generals 200 years ago
“If we were alive you know, 200 years ago, we'd probably be generals, like fighting some sort of wars or something.”
Nico Laqua May 30, 2026 ▶ 12:12 The Hardest Working Startup in America | Nico Laqua, Co-founder & CEO @ Corgi · 20VC with Harry Stebbings
What-if
Laqua: Public markets fail to properly value high-growth companies like Corgi
“If we were a public company, we'd probably be worth less because the public markets don't know how to evaluate high growth or potential.”
Nico Laqua May 30, 2026 ▶ 42:12 The Hardest Working Startup in America | Nico Laqua, Co-founder & CEO @ Corgi · 20VC with Harry Stebbings
What-if
Siemiatkowski: Klarna should have exercised greater caution on hiring before layoffs
“I could have been, you know, more careful, specifically on the hiring side, because it was very sad and difficult to me to, like, a few quarters earlier be hiring at a high pace, and then a few quarters later have to announce layoffs. That, that I felt that, l…”
Sebastian Siemiatkowski Feb 16, 2026 ▶ 41:10 Klarna CEO: SaaS is Dead: Why Systems of Record Will Die in an Agentic World · 20VC with Harry Stebbings
What-if
Ariel Cohen: Building Navan required sacrificing early family time
“It wouldn't. It wouldn't. That's the price. That's the price.”
Ariel Cohen Feb 7, 2026 ▶ 49:24 20VC: From $6.2BN Market Cap to $2.8BN: What Is Not Translating About Navan's Public Story | Are Any Public Company CEOs Actually Happy? | Why Navan Built It's Own Customer Service AI and What it Could Mean For Customer Service AI with Ariel Cohen
What-if
Zeev regrets deploying capital too quickly in 2021
“And then, by the way, sometimes looking back, you know, if I look at 2021, I would say I did, I invested too fast. You know, I wish I didn't, ok?”
Oren Zeev Feb 2, 2026 ▶ 29:09 Oren Zeev: Why AI Growth Expectations Are BS & Won't Last? Why GPs Shouldn't Tell LPs Their Strategy
What-if
Peet: Couldn't achieve career success without wife as full-time mom
“No chance. None.”
Chad Peets Jan 9, 2026 ▶ 50:34 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
What-if
Alan Chang: Shell would be worth more if listed in the US
“I think if they were listed in the US, they'd probably be worth more.”
Alan Chang Jan 5, 2026 ▶ 1:04:14 Fuse CEO Alan Chang: The Revolut Playbook of Speed & Ownership, Why Founders Aren’t Ambitious Enough · 20VC with Harry Stebbings
What-if
Marolf: On would have explored non-vegan tennis shoe materials earlier
“We probably would have explored different materials earlier, whereas I think we took a very conscious decision to make that a vegan product for all the sustainability reasons behind it, where then durability is sort of the other side of the equation. And we pr…”
Gérald Marolf Dec 19, 2025 ▶ 16:28 20Product: On Running's CPO on How to Create Emotion Through Product | Why 99% of Products Fail and How to Create Cults Around Products | The Biggest Product Mistakes On Have Made & Lessons Learned with Gérald Marolf
What-if
Recent a16z portfolio startups would access cheaper capital in public markets
“I can say in our portfolio, the companies that we have invested in over the last year or so, I'm pretty confident that if they were in the public markets, they'd probably have access to capital at a cheaper cost.”
David George Dec 15, 2025 ▶ 9:27 a16z's David George on the Most Controversial Bet at a16z & Do Margins and Revenue Matter in AI? · 20VC with Harry Stebbings
What-if
Mansour: Kalshi and Polymarket pushed each other's product and marketing harder
“Without Polymarket, we wouldn't have I think like, Pushed our marketing and pushed our product as hard. And without us, they wouldn't have pushed their marketing and their product.”
Tarek Mansour Dec 8, 2025 ▶ 12:05 Kalshi CEO Tarek Mansour on Raising $1BN, CNN and CNBC Deals & the Polymarket Feud · 20VC with Harry Stebbings
What-if
Carl Rivera: Start in person and go fully remote at 150 employees
“If I started a new company, I believe I would start it in person, and I would have an agreement that at some level, say, a 150 people were all going to turn remote.”
Carl Rivera Nov 14, 2025 ▶ 41:25 20Product: How AI Changes Product Design | Does the Design Phase Become Irrelevant in a World of Vibe Coding | The Five Pillars of Truly Great Product Design with Carl Rivera, Chief Design Officer at Shopify
What-if
Ferriss: The Tim Ferriss Show wouldn't exist without his book's commercial hurdles
“The podcast wouldn't have happened if all that hadn't happened.”
Tim Ferriss Oct 31, 2025 ▶ 35:13 20VC: Tim Ferriss: Why I Walked Away From Angel Investing After Uber | How I Accidentally Lost $150 Million | Money Fixed My Problems—Then Made Me Miserable
What-if
Bouaziz claims Deel turned down a higher valuation to pick ideal investors
“We could have raised even more and at a higher price too.”
Alex Bouaziz Oct 20, 2025 ▶ 58:03 Deel CEO, Alex Bouaziz on Raising $300M+ at a $17BN Valuation · 20VC with Harry Stebbings
What-if
Lemkin: xAI would not exist without Elon Musk's grudge against Sam Altman
“I don't know if XAI would exist if it wasn't for his bone to pick with Sam Altman. He might not have bothered. He might have just gotten to Mars faster.”
Jason Lemkin Oct 9, 2025 ▶ 11:45 OpenAI's Multi-Billion Deal with AMD & Polymarket, Vercel and Supabase Raise Mega Rounds · 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
What-if
Nejatian: Would not have taken Opendoor CEO role without Rabois and Wu
“Wouldn't have taken a job, would not have taken a job without them. Like a strip wouldn't have done it. In fact, I said I won't do it without them.”
Kaz Nejatian Sep 18, 2025 ▶ 19:51 Opendoor CEO, Kaz Nejatian: OpenAI and Oracle, How Can Either Afford to Do This · 20VC with Harry Stebbings
What-if
Stebbings: European tech founders sold early due to lack of secondary liquidity
“The thing I often think is how many great European companies of the last 20 years would have not sold had we had secondary and liquidity options available at the time, because so many did sell, because we didn't have that and it was so meaningful.”
Harry Stebbings Sep 8, 2025 ▶ 1:14:18 ElevenLabs CEO/Co-Founder, Mati Staniszewski:The Untold Story of Europe’s Fastest Growing AI Startup · 20VC with Harry Stebbings
What-if
Junestrand: Legora would not have connected with Benchmark without YC
“And so by being in YC, we raised money from Benchmark, who we would have not been introduced to if we weren't in YC.”
Max Junestrand Aug 15, 2025 ▶ 28:43 20VC: 15 Term Sheets in 7 Days and Choosing Benchmark | Harvey vs Legora: Who Wins Legal and How to Play When You Have $600M Less Funding | Are AI Models Plateauing Today | Building a 9-9-6 Culture From Stockholm with Max Junestrand
What-if
Martin Mignot: Index Ventures missed out on Qonto due to Revolut bias
“We could have invested in any, you know, in a lot of other neobanks you know, you think, I mean, Qonto would be a really good example of that. A lot of, you know, remittance and certain corridors, and so there's a lot of players.”
Martin Mignot Aug 11, 2025 ▶ 17:16 Index Ventures Partner, Martin Mignot: Figma, Scale, Wiz: Inside Index’s Decacorn Factory · 20VC with Harry Stebbings
What-if
Brent Hoberman regrets passing on acquiring Booking.com at the seed stage
“I made one pivotal mistake at last minute.com. I had the opportunity to buy booking.com at the time as a seed stage company. I still regret that to the present day.”
Johannes Reck Jun 23, 2025 ▶ 12:58 GetYourGuide CEO & Founder, Johannes Reck: The Wild Story Raising $450M From Masa and Softbank · 20VC with Harry Stebbings
What-if
GetYourGuide would have gone bankrupt during COVID without its $450M round
“For us it was the decision that ultimately made Get Your Guide into what it is today, because just six months after we raised that money, COVID hit. So we would be bankrupt without that round.”
Johannes Reck Jun 23, 2025 ▶ 35:04 GetYourGuide CEO & Founder, Johannes Reck: The Wild Story Raising $450M From Masa and Softbank · 20VC with Harry Stebbings
What-if
The venture downturn allowed G Squared to build a large Wiz position
“Normalized scenario, we would have never been able to build this position in Wiz because it would, it was a hockey stick from day one, but the capital availability, even to the best assets in the world, wasn't great for 18 months.”
Larry Aschebrook Jun 16, 2025 ▶ 1:21:21 Larry Aschebrook, Founder & MP @GSquared: How We Lost Money on Uber and Made Millions on Lyft · 20VC with Harry Stebbings
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
What-if
Jack Zhang would have made $3B accepting Stripe's acquisition offer
“If I know Stripe gonna get to a hundred billion, I mean, I will probably make, like, at least three billion dollars.”
Jack Zhang May 26, 2025 ▶ 1:02:35 Airwallex CEO & Co-Founder, Jack Zhang: The Angel That Turned $1M into $1BN · 20VC with Harry Stebbings
What-if
Airwallex would have died without raising $400M in 2021
“I think air wallets will be dead without twenty-twenty-one. Right. We raised four hundred million dollars.”
Jack Zhang May 26, 2025 ▶ 1:19:52 Airwallex CEO & Co-Founder, Jack Zhang: The Angel That Turned $1M into $1BN · 20VC with Harry Stebbings
What-if
O'Driscoll: Deel CEO should pay whatever it takes to settle lawsuit immediately
“If I was, my ass was on the line, and I was the CEO of Deal, I'd be like, how much money does it take to settle this thing by Friday?”
Rory O'Driscoll May 22, 2025 ▶ 58:18 Rippling vs. Deel Lawsuit: WTF Happens Now? The Future of the Late Stage Private Market · 20VC with Harry Stebbings
What-if
O'Driscoll: Ivy League CFOs Must Overhaul Cash Planning This Year
“If I was the CFO of an Ivy League university, let's just say my cash Planning for this year would be dramatically different than my cash planning normally.”
Rory O'Driscoll Apr 24, 2025 ▶ 0:24 How LP Deployment to Venture Will Change in 2025 & Are Endowment Funds in Trouble? · 20VC with Harry Stebbings
What-if
Stebbings: Passed on ElevenLabs at $25M valuation, missing a fund return
“11 labs at twenty five million. I could have had one percent of the company. And I was like, one percent. And like, no way. It was a twenty five million dollar fund. It's a three billion dollar company now. I would have been a fund return.”
Harry Stebbings Apr 24, 2025 ▶ 1:08:58 How LP Deployment to Venture Will Change in 2025 & Are Endowment Funds in Trouble? · 20VC with Harry Stebbings
What-if
Garcia: He wouldn't build Carvana again in a thousand lifetimes without luck
“If I got to live a thousand lifetimes, I don't think that I would be likely to be part of something as big as Carvana in very many of those lifetimes. Because I think that there is luck in the world.”
Ernest Garcia Apr 7, 2025 ▶ 28:59 Carvana CEO & Co-Founder, Ernest Garcia: Building a $50B Company, Losing 99% and Coming Back · 20VC with Harry Stebbings
What-if
Singlehurst: Passing on Stripe's down round was a mistake
“I think that was a mistake. I think we should have put more in them.”
Peter Singlehurst Mar 19, 2025 ▶ 52:11 Peter Singlehurst: Lessons from Turning Down Stripe, Coinbase and Losing Money on Northvalt · 20VC with Harry Stebbings
What-if
Selling Stocks at Lockup Would Have Lost LPs $2 Billion
“If we had sold them all at lockup, we would have returned two billion dollars less to our LPs.”
Jake Saper Mar 10, 2025 ▶ 1:13:18 Jake Saper, GP @ Emergence Capital: "We Sold Salesforce Early and Lost Out on Billions" · 20VC with Harry Stebbings
Made with StarZero

Turn any episode into a week of clips.

This entire site, over 1,200 episodes transcribed, diarized, checked and made playable, runs on the StarZero media pipeline. Drop in your own episode and the podcast clipper finds the moments worth sharing, cuts them, captions them, and reframes them for every feed.