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
Conrad: Zenefits' outcome would differ if A16Z and Sacks hadn't ousted him
“If I had fought at my last company, being forced out by A-sixteen Z and David Sachs, and had stayed in place, like, if we could replay the videotape, what would the outcome for that company have been? I believe that it would have been very different”
Stebbings: Investing in every met founder would yield 17x greater success
“If I'd invest in every founder that I'd met, every founder that I've met, I'd be 17 X more successful. One seven X more successful. I would have had two and a half percent of deal. I would have had two percent of 11 Labs. I'd have a seed check in Flettersport,…”
Jake Paul Claims He Would Be the Best Boxer With Lifelong Training
“If I had been doing it my whole life, I'd be the best boxer in the world for sure.”
Lemkin: Uber would be worth $1 trillion today under Travis Kalanick
“I think Travis Uber would be a trillion dollar company today because it would be five years ahead of where it is today.”
O'Driscoll: Musk's death would cut Tesla 80%, Altman's cuts OpenAI 25%
“Tesla trades at a trillion today. I think if Elon died tomorrow, they traded two hundred billion. OpenAI trades at eight hundred billion today. I think if Sam Altman died tomorrow morning, we traded six hundred billion.”
Jerry Murdock: Twitter would have been far better without VC politics
“Twitter could have been infinitely a more interesting company, but VCs got involved and created politics, and they fired Jack Dorsey early, and I don't know if that was right or wrong, but they created issues, and the company was pretty messed up.”
Snowflake could have killed Databricks by building a notebook and Spark connector
“I would just would have hired more salespeople and focused on new logo acquisition and pounded on product to give me a notebook and a spark connector, and we would have kicked the shit out of Databricks and they would be dead.”
Hacker: Duolingo could not have raised any funding in Europe
“But I can guarantee you Duolingo would not have been able to raise any money in Europe.”
Hacker: Strict US immigration rules would benefit European tech
“In a way, the best thing that could happen to Europe is if the U.S. Made it really hard to immigrate for founders. You know, if they made it really hard, if they restricted immigration such that you know, people like me couldn't, couldn't move there anymore, t…”
Hoggett: London market would have valued Arm's AI growth equally
“AI trade, which I'm utterly convinced would have happened in London as much as it happened anywhere else. I don't think, I think it's a, you can't prove a negative, but I think it's a falsity to say a London market wouldn't have valued that the same way.”
Green: A Benchmark-backed Silicon Valley version of SafeSend would've fetched $500M
“Had that deal, been backed by Benchmark, like Vishra or Fett, Peter Fett, and one of those guys, backed a Benchmark, doing a minority deal based in Silicon Valley, it would have been five hundred million dollars.”
Pishevar: Uber would be worth $1T if Travis Kalanick stayed
“I believe if Travis and Emil had stayed at Uber, Uber would be a trillion-dollar company by now.”
Pishevar: Uber allies should have staged OpenAI-style employee revolt for Kalanick
“What I wish I had done or had the wisdom to know to do was what, you know, Sam and his allies did in getting the employees at OpenAI to back Sam and say, if he doesn't come back, we're gonna leave. . It was very powerful, and if we had done that at Uber, becau…”
McCabe: If starting over, Intercom would require five days in-office
“If I started all again, I would definitely do five days a week. I think just being a person is just far superior.”
Chirls: Coinbase would have succeeded without Andreessen Horowitz and USV
“Would Coinbase not have been successful? If they hadn't take money from Andreessen Horowitz and USV. No, I think they would have been just as successful.”
Asparouhov: Uber would be a $1T company if Travis Kalanick remained CEO
“But perhaps those benchmark LPs would have made even more money if Travis was still CEO, And the future of self-driving cars lived within Uber rather than living within Google. And maybe Uber becomes a one trillion dollar company over the course of the 20 twen…”
Alex Wang: China or Russia would use AGI to conquer if developed first
“Let's say China or Russia had AGI today and the United States didn't, I would imagine they would use that to conquer.”
Ehrenberg: I Would Spend Almost No Time Investing in Pure AI
“I'm not in pure tech anymore, but if I was, I would literally be spending almost no time in pure AI.”
Rabois: LinkedIn should have been more valuable than Facebook
“LinkedIn by any measure was Yeah, pretty successful. Certainly impact, you know, acquisition, twenty four billion or so. Truthfully, probably hit somewhere between five and 20% of its, you know, potential because it didn't do some of these things. Like, I, in …”
Tomaino: Incumbent VCs would lose prestige if judged on fund performance
“If you know, everyone viewed Fund performance as the, you know, the metric of success, these, the big, you know, incumbents wouldn't have the prestige that they have.”
Ackman: Lack of SVB Guarantee Would Have Caused Regional Bank Runs
“Woke up Saturday morning after the events of the week, pretty convinced that if the government didn't, at a minimum, guarantee deposits at Silicon Valley Bank, we'd have a massive run at pretty much every regional bank on Monday.”
Jason Fried would ban workplace political discussions again despite the employee backlash
“If I had to make it again today, I would make the same decision.”
Immelt: No other leadership team on earth could have saved GE in 2008
“We made it to shore, we saved the company, we preserved the businesses, and I would say to people, look, no other team on earth could have done what we did.”
Sahil Lavingia regrets taking Accel's $400K seed check over super angels
“Frankly, if I could go back in time, I would have said no to them. I would have given that 400 K a hundred K to four different people, super angels or angels, or even split it further.”
Cuban claims Uber and Twitter would be more successful outside Silicon Valley
“I think if you take some of the companies, Twitter, or almost any of them, Uber in particular, Lyft, and you move those to Kansas City, Dallas, Pittsburgh, Buffalo, New York, they would have been so much more successful, so much more quickly.”
Petersen: Flexport Would Have Succeeded Without Investor Operational Support
“Most of them have been amazing, like connecting, making connections and stuff, but we would have pretty much had the same company without any given thing that any of them did besides give us lots of money.”
Clavier: Fitbit Would Have Died Without Brad Feld's Series A Investment
“Every single round of financing was either close to impossible, To raise, I had to beg Brad failed to invest in the Series A saving Fitbit, because without that investment from Brad, they would be dead, and even the Series B or the Series C were not easy, desp…”
Weitzman: Meta would be ripping without GDPR and US data regulations
“If GDPR didn't exist and the other laws in the US didn't exist, Meta would be ripping. They just can't train on their data properly.”
Mac: Uber Could Run Today's Scope in Five Years with Fewer People
“If you took everything Uber does today and held it static and said, you know, in five years you're going to need more or less people, I'd say, well, we could do everything we do today with less people in five years because of the power of AI, but we're going t…”
Figma missed market share later captured by Replit and Lovable
“I firmly believe a big chunk of Replit and Lovable could have been Figma's if they'd done it.”
Rejecting 1% allocations in Deel and ElevenLabs cost Stebbings massive returns
“There have been several companies where we've had, like, one percent offered to us, Deal, 11 Labs, Starcloud, where we were like, one percent, we can't be doing that, and now I look back and all of them would have returned huge amounts of money.”
O'Driscoll: Without open source, Coinbase's AI costs would have sextupled
“The counter counterfactual is if those open source product didn't exist, the Brian Armstrong quote would tweet would have been, We were paying ten million dollars six months ago for our AI intelligence. Now we're paying 60.”
Chris Degnan: Slowing sales hiring at Snowflake for IPO was a mistake
“We, and I mean, we said it earlier and I said on your last podcast, we should have kept hiring. We slowed down. Because we optimized to be public. And that was a mistake, my opinion. And by the way, I, I'm, I w my hand was on that wheel.”
Weitzman: LLMs provided confidence to challenge doctor and locate specialized scanner
“I would have never had the confidence to push on the doctor so hard to get the scan if I didn't have LLMs open during the conversation with the doctor. I definitely would not have found another machine, got my dad scanned, and then figured out.”
Steckman: Anduril missed offensive cyber warfare seven years ago but will enter
“We should have moved into that seven years ago and been the first in it. We weren't big enough probably to really even understand it seven years ago, but like in hindsight, it was kind of obvious. You know, we'll, we'll probably try and play some catch up here…”
O'Driscoll: Uber should have re-hired Travis Kalanick in 2022 for autonomy
“Actually, it turns out, in retrospect, they should have done the Steve Jobs thing. They should have swapped them out, got it public, got a cash flow like crazy, and sometime in 22 should have gotten back and said, now, Now is the time to do autonomy”
Clements: Breaking VC rules for Rippling would have been worthwhile
“And I think like, I don't regret not breaking the rules in general, but you know, this would have been a time when it could have been worthwhile.”
Junestrand: Legora would have churned all customers without sales freeze
“Because I think if we had continued to push, we would have just churned everything.”
Ross: OpenAI and Anthropic revenues would double with double compute
“If OpenAI were given twice the inference compute that they have today. If Anthropic was given twice the inference compute that they have today, within one month from now, their revenue would almost double.”
Deeter: Tesla wouldn't have survived without DOE loan
“Without the, you know, the DOE bailout loan and things, Tesla wouldn't have existed, but what I missed was that Elon's a force of nature, a generational entrepreneur, and he put that company on his back and powered through so many subsequent layers that the ne…”
Mignot: Auto-investing in every pitch would have yielded better returns
“We ran the same analysis, where if you had said yes to every single company that had come to present at the partnership, we'd have done a lot better than we have. Simply because it goes back to the power law.”
O'Driscoll: Figma's $98 IPO pop only happened because it priced at $38
“The 98 price only happened because the IPO happened at 38.”
Lemkin: Adobe's $20B Figma acquisition would look like a great deal today
“You know, it also, you know, I mean, Scott Belsky was right. They should have bought him. People made fun of them for overpaying, right? Twenty billion, right? But I think the beauty is if you're Adobe, you can be a little patient. It's okay if you pay two yea…”
O'Driscoll: A perfect product wouldn't win Dropbox new enterprise customers over Glean
“Even if Dropbox had shipped a perfect, hear me out, even if Dropbox had pitched a perfect functionally equivalent product to Glean, it would mean that for their existing business customers, which is a smallish percentage of their total business, they would win…”
Lemkin: Clay Should Raise $100M and Go Scorched Earth
“So I would armor up if I were Clay. I would hire everybody. I would raise another hundred million and I would just scorch earth everyone in the space.”
Stebbings: Anthropic and Cursor Venture Investments Would Have Saved FTX
“When you look at FTX, their positions in Anthropic and Cursor actually would have saved them if they had the time to prove that out and they hadn't done the commingling. That would have saved their financial performance with those two investments alone.”
Hinrikus: Wise would not have received a pricing premium in the US
“I don't believe Wise would have a pricing premium in the US.”
Wilk: Going Public 9 Months Earlier Would Have Prevented Dave's Crash
“Had I gone public nine months earlier, we would have had the chance to raise potentially more capital. We would have been able to Turn over our earlier shareholders, bring more longer term capital. And like, we never would have gone to a five billion dollar va…”