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.
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
Emergence Missed Out on $2 Billion by Not Selling Stocks at Peak
“What's interesting, and this just is like totally coincidental, if we had sold all of our shares at peak price of whatever, whenever the peak price proposed for that stock, we would have made two billion dollars more for our LPs.”
Teixeira regrets 1Password didn't invest more aggressively in product and M&A
“I think we had the opportunity to be a lot more aggressive investing in Product and engineering, whether that's sort of like a build or buy scenario. Again, I think we had the benefit of being a profitable business with a lot of cash at a time when many compan…”
Lime Would Not Lead Micromobility if Unvetted VC Funding Had Continued
“If the funding continued to flow without real assessment of whether or not a company is doing a good job or bad job, I think Lime would not be the global leader right now because it would allow our kind of worst managed competitors to continue to scale and gro…”
Lime Would Not Have Survived the Pandemic Without Acquiring Jump
“Line wouldn't have survived if we did not do that deal.”
Navan Would Have Failed Without Its Pandemic Strategy Pivot
“And so by going up market and by building a second product that company didn't die and it would've.”
Kanji: Hoxton Would Have Been a 10X Net Fund on Darktrace at Peak
“We, that would have been, we would have been a 10 X net fund on, on, on, on Darktrace at the, at its peak.”
Riparbelli: Denmark would have been an impossible place to build Synthesia
“I come from Denmark, right? That would have been a terrible place to build a company. That would have been impossible, basically.”
Stebbings: 20VC passed on ElevenLabs at a $25M valuation
“We could have done 11 Labs, which is a three billion dollar company, probably the best company coming out of Europe now. Could have done it at 25.”
Sertoglu: Doubling UiPath's seed valuation would not have impacted fund returns
“For UiPath, if we'd done the seed round at twice the valuation, it wouldn't have really, you know, made a, made any difference. It would have still been a fantastic outcome.”
Stebbings: Passing on a 2% stake in ElevenLabs was a major mistake
“My biggest mistakes, most recently, 11 Labs in particular, is where I was like, you got like two percent, and I was like, it's just not enough. And actually two percent would have been great in hindsight.”
Sertoglu: Earlybird should have participated in Sequoia's $3B UiPath round
“In hindsight, we should have participated in that three billion dollar round by Sequoia.”
Khachab: Choco should have tripled its burn rate in its first years
“I wish you would have, you know, spent double the amount of money, have tripled the amount of burn probably in the first 24 months of our company.”
Wang: SCGE should have trimmed portfolio positions more aggressively in 2022
“I think 2022 was a period where a lot of these stocks got ahead of themselves and we should have, we had to trim, we trimmed a bunch, but we should have trimmed more.”
Vishria: I should have broken comp rules to hire key talent
“There were a couple times or two people and specifically that I think about where like what they wanted in comp and what I was like willing to give were separate. Like they were just off and they were so far out of market in terms of what their ask was. And I …”
Stebbings: I should have sold secondary positions in Clubhouse, Hopin, and BeReal
“Truth be told, honestly, Nick, I've been in some rockets that then turned out to not be rockets. Your clubhouse to your hop in to your be real. And they are portfolios with assets in, whether you like it or not in terms of naming. And I should have been much m…”
Khan: Box and Dropbox margin expansion required public market discipline
“Like, I don't think the margins that Box and Dropbox is generating, if they could have generated, if they would just stay private. Because the growth was slowing, they were forced to look at the business and run the business better.”
Alexis Ohanian: Initialized could have returned Fund I by selling Zenefits
“I should have sold, we got, we could have returned the fund once over in whenever the fidelity markdown was, like literally putting an SPV together to sell Zenefits and then the markdown, the fidelity markdown happened and it killed the SPV. That was one, that…”
Alexis Ohanian regrets doubling down on Clubhouse instead of selling
“Oh, Clubhouse. That's when I should have sold. Should have sold Clubhouse. I had like the series A and I remember when that multi-billion dollar round came up, I actually put more money in because I'm an idiot.”
Hartz regrets turning down Peter Thiel's invitation to join Palantir at inception
“The day that acquisition of PayPal by eBay was announced Peter had resigned, and I met him up at the Sundeck restaurant in up on Sand Hill Road, and he said, you know, Kevin, I'm working on this business, and, you know, we're taking kind of the fraud algorithm…”
Ara Mahdessian: ServiceTitan Should Have Launched Payments Earlier
“Yeah, I would say that was an example of us not seeing the opportunity to build a great payment solution. And we should have done it earlier.”
Grady: Sequoia missed a $30B gain by distributing ServiceNow stock early
“If we'd held ServiceNow through to today, it'd be a, I don't know, a thirty billion dollar gain, right? But we didn't. We distributed it a year or so after the IPO because it was the first billion dollar gain over time, not all at once, but it was within the f…”
Blomfield: Profitable $1M ARR YC startup accepted lower valuation due to fundraising anxiety
“And this happened to a couple of my companies, this batch, where a phenomenal, like, crazy all-star team, like, ridiculous, like, every sort of pedigree you'd want amazing product, profitable, like, more than a million in revenue, and that just, the founder wa…”
Lazy due diligence caused Bending Spoons to misjudge an acquired app's growth
“Had we done our homework more thoroughly, I think we would have spotted that some of the underlying factors were waning and dropping quickly, and that consequently the rate of user acquisition was likely to shrink faster than we had anticipated.”
Ehrenberg: Holding The Trade Desk Longer Would Have Added 5x-10x Fund Return
“We could have held onto TTD and returned another five to 10 X of the fund.”
Gonto: Amazon would never have launched AWS without trying the Fire phone
“And if they weren't willing to try Kindle phone, they would never be willing to try AWS.”
Procore survived 2008 because one investor kept injecting capital
“Honestly, if we didn't have the wherewithal to survive the great financial crisis thanks primarily to one of our investors who kept pumping money into Procore we wouldn't have survived”
Richter: HelloFresh could not have IPO'd at any other time
“I think the way that our category traded would have not allowed us to IPO the business at any other point in time.”
Sim: Snyk Would Have Failed Without Continuous Internal Funding Prior to Series A
“If Guy went out trying to raise capital from someone else and I didn't have enough capital to give to him, he would have gone out of business.”
Prince: Cloudflare would have failed by targeting a narrow startup niche
“If we had really said, we're going to focus on this and start there and, you know, constrain, like, and our marketing copy said, you know, Cloudflare is a service for startups and small businesses and did all those things. You know, if we'd started with the na…”
Velez: Full-time RTO would cost Nubank top global tech talent
“And so, if we were to say everybody has to be in the office, we would gain a bit in terms of faster decision making, faster ability to innovate. I believe in all the pros of being in the office, but we will lose a lot of the incredible valuable talent that we …”
Threads Would Not Have Succeeded Without Instagram Graph Bootstrapping
“And I think that's, it is no way it would have been as successful if you had to bootstrap the graph from scratch.”
Paik: TikTok could not exist before Twitter due to bandwidth constraints
“There's a very clear reason why the order of founding went from Twitter first, to Instagram, to Snapchat, to TikTok. And it is because mobile as infrastructure and bandwidth in its earliest stages, supported the lowest packet size, text. And then next compress…”
Tobi Lütke: Shopify would have gone fully remote even without COVID-19
“I think within a year or two, I would have transferred Shopify to remote entirely.”
Systrom would not work 16-hour days if he were in an office
“And if I were working this hard elsewhere, first of all, I wouldn't work this hard in an office. It just wouldn't happen.”
Firing Doc Rivers and Danny Ainge in 2007 Would Have Ruined Celtics
“Had we fired those guys, we'd be nowhere and those guys went on to be in the conference finals, and they, they're two of the best people in, in the business.”
Walk: Raising a $200M-$300M fund would have sacrificed team happiness
“Raising 203 hundred million dollars, you know, like some of our peers and going to market in a model where we brought on another GP, we expanded our team, we brought on another platform person. Like, I actually think we could, you know, Hit exceed our benchmar…”
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.”
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 …”
Katzenberg: DreamWorks' survival depended on pivoting to computer animation
“And for me, having lived through the disruption of hand-drawn animation to computer animation I would say was, you know, probably one of the greatest challenges, and our survival literally depended on our ability to make a pivot. It was brutal. We lost a lot o…”
Katzenberg: DreamWorks would have gone bankrupt without computer animation pivot
“Having lived through the disruption of hand-drawn animation to computer animation, I would say was Probably one of the greatest challenges, and our survival literally depended on our ability to make a pivot. It was brutal. We lost a lot of very talented people…”
Singerman regrets not putting $500M into Airbnb's $1.5 billion valuation round
“I wish I had written 500, I wish we had written a five hundred million dollar check into Airbnb at the, you know, one and a half billion dollar round instead of a, whatever, a hundred and fifty million dollar check.”
Weil: Directly plopping Snapchat Stories into Instagram would have failed
“But I think if you had just taken stories and like plopped it in the middle of Instagram, it wouldn't have worked.”
Battery missed Snowflake by over-indexing on early customer complaints
“If we had looked at the founding team and the infrastructure they built, I think we would have looked past the individual customer feedback, a data point here, a data point there, that said, hey, this is still not quite ready for prime time, and instead focuse…”
Deep-Tech Startups Should Raise Maximum Early Capital to Offset Risk
“And so I think for businesses that have that ambition where they're trying to build something that's never existed before, And frankly, it has a lot of existential technology risk, which our business certainly did early on. I do think raising a lot of capital …”
Reber: Wunderlist could have reached hundreds of millions of users independently
“I think Wunderlist had a very unique character and could have grown to hundreds of millions of users and could have had a successful business process”
Boufarhat: Hopin Could Not Have Scaled Rapidly Without Being Fully Remote
“I don't think it would have been possible two to three years ago, and if we were not a remote business.”
McCabe: Intercom would be 10x larger if started with bigger ambition
“I'm pretty sure that all other things being equal, if I was able to go back in time and start Intercom again, by this stage, it probably would be 10 exercise only because I now know that I can think bigger, and that simply doing so gives you just so many more …”