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.”
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…”
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.”
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…”
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, …”
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 …”
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.”
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”
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…”
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.”
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.”
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.”
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…”
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.”
What-if
Fred Turner: Curative Could Not Have Been Built In The UK
“No, definitely not.”
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.”
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 …”
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.”
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.”
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…”
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.”
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?”
What-if
Peet: Couldn't achieve career success without wife as full-time mom
“No chance. None.”
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.”
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…”
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.”
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.”
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.”
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.”
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.”
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.”
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.”
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.”
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.”
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.”
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.”
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.”
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.”
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.”
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…”
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?”
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.”
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.”
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.”
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.”
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.”