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
Garcia: Underpricing Carvana's IPO for a pop would have risked failure
“If we would have, you know, priced it at 10 or eight or whatever to try to get some magical bump, we would have gotten a lot less money and would have been more likely to not make it across the line. And we would have, you know, taken more dilution for all of …”
Garcia: Taking on massive debt saved Carvana from catastrophic equity dilution
“Had we raised equity in the same dollars at the same time that we took out debt we would have taken a lot more dilution than let's say that we just like raised equity today and paid it off just to like, you know, allow you to do that math. We would have taken …”
Torres claims Drift would be public without executive equity concessions
“I would have a public company right now if I, if it wasn't for like all those carrots that I gave and candy bars and trophies.”
Opening Odoo's San Francisco office was a mistake
“Retrospectively, if I would have opened it elsewhere, I would have preferred, yes.”
Riparbelli: Synthesia would have considered selling early without founder secondary liquidity
“I think it, I'm 100% certain that they have to take no seconders at all. We would definitely have thought about selling much earlier.”
Plank: Rippling couldn't compete in niche verticals without specialized reps
“Had we not done that, We never would have been able to compete in these kind of, like, hyper-competitive, like, vertical spaces like finance and global payroll”
Hoffman: Ukraine's initial defense would have failed without Starlink
“And by the way, the initial defense of Ukraine would not have worked without Starlink.”
Markus Villig: Bolt's success was nearly 100% luck from finding key co-founder
“Without Oliver, the company would have never be where it is, so I'd say it's even close to a hundred percent of luck.”
Villig: Listening to external advice in 2019 slowed Bolt's global expansion
“Probably we should have been even more aggressive in our expansion. So if I look back at this period that we had from 2015 to 19, where we launched all of these markets remotely, it was a fantastic time. I think what we did back in 2019 was that we started rai…”
Kothari: Reinventing Notion's sales machine cost the company three years
“If I had to do it one function all over again, I would do sales. And the way I would do it is to not try to like overthink it, just do it the way it is run, like a proper sales machine. I think it would have saved three years in that journey.”
Nejatian: Shopify might not have gone remote if leadership foresaw the difficulty
“So if, I think if we knew how painful it would be, I don't know if we would have done it.”
Nejatian: Internet commerce is weirder than if Yahoo Stores had won
“Commerce on the internet is slightly more weird than it would be if Yahoo had won. Yahoo Stores had won, which is like the Paul Graham product. I like Paul Graham a lot, but I'm very glad that his software at Yahoo did not win.”
Grady: My venture success came from Sequoia's platform and 2007 timing
“Let's say you'd picked any random person off the street in March of. And plop them down into Sequoia where they have one, the greatest business card you could possibly hope for to the beginning of the cloud mobile transition. And three, you're about to head in…”
Grady: Sequoia should have split from India and China branches earlier
“In 2005, when we got into India and China, we did so with the thesis that the world is getting smaller. When we parted ways in 20, 23, it was because that thesis in some ways had been invalidated. And so I think maybe we could have done that a few years sooner…”
Matt Clifford: Europe and India Would Rival Silicon Valley With Top Talent
“Like, why does Silicon Valley work? Because the most ambitious and talented people in that area become founders. If the same thing happened, In the UK, in Europe, in India, we'd have very similar outcomes.”
Mario Schlosser: Oscar Health would not exist today without its IPO
“And frankly also Oscar wouldn't be around having not gone public.”
Lonsdale: The Russia-Ukraine War Was Unnecessary Under Savvier US Leadership
“And I think that this conflict was unnecessary if we'd had a president who was savvier about how to handle it”
Duolingo's viral TikTok strategy would not have succeeded with remote work
“I don't think so. And I say that as someone who is a homebody and loves being remote, but like, it's honestly like having even, I mean, if you have a suit, maybe, but having the suit and just the random quirkiness and the thing, like the things around our work…”
Stebbings: Reserving capital would have caused bad investments in Hopin and Clubhouse
“If I had done reserves, I would have put money into Hopin, Clubhouse, and be real. That would not have been a good set of events.”
Sim: Meta's acquisition of Kustomer would not be approved by regulators today
“Fuck no. No way. And by the way, it had nothing to do with anything other than they hated Zuckerberg, right?”
Courtemanche: Procore would never have succeeded with per-seat pricing
“I realized that I couldn't go with a per seat model because that was going to actually make it so we were never going to be successful.”
Prince: Without Cloudflare, Ukrainian Defense and Global Communications Would Have Struggled
“Had we not done that, it would have been much harder for President Zelenskyy to get, get the message out on what was happening. It would be much harder to see what was happening on the front. It would be much harder to see the atrocities that the Russians Cont…”
Sheikha Regrets $3.1B Uber Deal Didn't Financially Benefit Careem's Drivers
“I wish we could have done more for our captains. As a part of the exit process. You know, Kareem was built by these captains and we are close to many of them. And if I look at them today, they're still doing what they were doing 10 years ago. And that saddens …”
Douwe Kiela: Current AI breakthroughs would not happen without Meta's PyTorch
“So PyTorch really without PyTorch, none of this stuff would be happening right now. And so it's really like fundamental for all of the AI breakthroughs.”
Douwe Kiela: The open-source AI ecosystem exists solely due to Meta's LLaMA
“This whole flourishing that you see right now of open source models that basically comes from Meta's generosity in giving Lama away for free. And if they hadn't done that, then you wouldn't see that.”
Weiss: Launching Slack Connect earlier would have driven massive network adoption
“And I think frankly, especially given the competitive backdrop there, I think if we had not rushed it, but expedited into market back before there were more products that, you know, people were starting to use or get for free as defaults. And back when I think…”
Summers: Fed should have raised rates earlier and stopped buying mortgages
“I would have recognized that Very substantially excess demand was developing. I would have moved to signal my awareness of that and to start putting my foot on the brakes much sooner than they did, and certainly as inflation was rising, as we were having a rec…”
TJ Parker: A decade in corporate pharmacy would have prevented founding PillPack
“If I had been working in pharmacy for a decade as an adult, there's no way I would have started a pill pack, because there were very specific reasons it shouldn't have worked, and I think that's where the naivety is really powerful.”
Delangue: Open Source Accelerated AI Progress by 30 to 50 Years
“Without open science, without open source, without Google sharing their attention is all you need paper, sharing their birth paper the latent diffusion paper. Maybe we would be 3040, 50 years away from where we are today.”
Carney: Delayed Federal Reserve Rate Hikes Allowed Financial Sector Excesses
“And that meant that You know, they lost six to nine months probably of tightening, ah, time that could have been spent initiating a more gradual tightening, squeezing out some of the excess which built up, you know, in these late stages of a cycle, you get the…”
Guo: Conviction capped debut fund at $100M despite $500M demand
“I could have raised half a billion dollars, and I thought that doing this was, if I believe constraints breed discipline and creativity for founders, like, They also do for investors.”
Salguero: ButcherBox would be out of business if it raised venture capital
“Actually, I think we'd be out of business if we raised money because we would have raised money in 2015 when it was hot with big valuations, we probably would have raised again. And then when all the money like would not had had to build a profitable business …”
Schultz: Meta Moved Too Slowly on Product Rollouts and It Was My Fault
“Personally, I think we took too long, and if I went back and did it again, I would have moved a lot faster, which is weird for a meta executive to say, but I actually think we moved too slowly, and in many ways it was my fault.”
Liquid Death would never have survived a Coca-Cola focus group
“Like Liquid Death would have never made it through a focus group at Coca-Cola.”
Jordan: Incredible Health could have gone from Series A to IPO
“Iman at Incredible had the just had this dream of, she called it A to IPO. She arguably could have never raised a B round and gone public. The business has that kind of momentum. And because she was quote unquote accidentally profitable, the bookings came in w…”
Emil Michael would have told Travis Kalanick to reject Benchmark's coercion
“Had I talked to him that day, I would have said, Travis, walk out of the room. If you want to rip up the papers in front of them and we'll get, you know, get a lawyer and whatever. This is ridiculous. You know, there's, this is unfair. This is coercive. And we…”
Emil Michael: Uber Eats would have beaten DoorDash under original leadership
“So I would have beaten door, we would have beaten DoorDash, guaranteed. We were ahead by 30 points when Travis Night left, so letting that atrophy was not an option.”
Emil Michael: Uber should have forced scared early investors to take liquidity
“And so more, the thing we, I wish we did more of Uber is give more investors liquidity when they get scared. I would be like Venturex sell. Like, I'll find you someone to sell to sell, go get the second G six and the, you know, the whatever. The discovery prop…”
Weil: Instagram Stories would have failed with a timid, experimental rollout
“If instead we'd done the timid thing and put it like in the back of a third tab and like, well, if people find it, we'll do a one percent experiment and maybe it'll work. Like it never would have taken off.”
Stebbings Missed $25M in Liquidity by Following Sequoia's Advice to Hold Winners
“My biggest regret and my biggest lesson is that I didn't, because I believed in Sequoia's, hold on to your winners, never sell your winners, and I didn't, and I probably could have taken off about twenty five million dollars for an eight million dollar fund.”
Zeev: Audible would be worth $50B to $100B today if independent
“Today, I believe that Audible would probably be worth 50, a hundred billion.”
Friedberg: DoorDash succeeded because Travis Kalanick left Uber
“They do not think they would have as successful as they were if Travis was still CEO of Uber.”
Kurtz wishes he took loans to buy more early CrowdStrike equity
“I probably would have took out as many loans as I could have and put as much money of my own money in the deal as early as possible.”
Sacca: Uber's IPO would have gone differently without SoftBank's DoorDash funding
“Uber's IPO would have gone very differently if they hadn't funded DoorDash.”
Immelt: GE should have partnered with Salesforce or Microsoft for software
“Here's what I would have done differently, you know, Harry, in all honesty, I've had four years to think about it, is I would have either bought a part of a startup company or done a joint venture with maybe salesforce.com or Microsoft and created a new co, cr…”
Levine: Bessemer Would Have Missed Pinterest Without Partner Sarah Tavel
“Had we not had, at least on a gender basis, A diverse duo of people looking at the investment. I think we would have missed it, too.”
Lightspeed Passed on a Snapchat Follow-On Investment at a $13M Valuation
“If we'd invested, I think that if we'd done that round, I think the terms were three on 13 or something like that. It would have been a great outcome for the company and for Lightspeed.”
Howard Marks: Central bank interventions prevented a 2020 global depression
“With that disclaimer out of the way, first of all, nine months ago, a global depression was absolutely a possibility. With the, most of the developed countries Certainly outside of Asia, shutting down their whole economies in order to limit contacts and bend t…”