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 34 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
Reina: ElevenLabs would have neared $1B ARR with earlier senior sales hiring
“And I think those two items, if we had done it much sooner, then for instance, we would have already passed a billion dollars in revenue, for instance, right? Or like getting close to that billion dollars in revenues.”
Perplexity Would Have Failed If Founded Six Months Earlier or Later
“If we had, you know, we got lucky with timing. If we had founded the company six months before we did, GPT-III would not have been good enough, the equivalent of it, at that point in time, and we wouldn't have been able to create that initial magical experienc…”
Eventbrite would never have IPO'd without its Nashville engineering hub
“Without the work happening in Nashville, IPO never happens for us. Just full stop. We never have an IPO if we didn't get ourselves to a place where our books could close regularly and consistently.”
Smith: Venture funding would have prevented Qualtrics from pivoting to XM
“If we would have just bought our way through, I don't think we would have had that confidence or DNA to pivot the whole company and create this new category of experience management, which is really what SAP wanted.”
Lemkin: HubSpot would be stuck at $1B growing single digits without CRM
“Where would it be without CRM? Where would it be? Right? This would be a niche product at a billion and something growing single digits.”
Yung: Chorus Won Early Deals Over Gong by Giving Equity to Advisors
“One thing that, that chorus did. Did better than us. Is they did a really good job of getting advisors pretty early. They, I think they got through giving them some equity, but they insert these like champions inside of decent sized organizations that would bl…”
Schuck: Acquiring RainKing and ZoomInfo earlier would have saved $700M
“We had looks at those businesses a year or a year and a half before, and if we had done the acquisitions earlier, we would have saved, I think, seven hundred million dollars in acquisition M&A costs.”
Blindly trusting conversion data would have trapped Lucidchart with a poor homepage
“If we had trusted, just purely trusted the data on all of those homepage experiments, We would still be stuck with that really crappy homepage as opposed to something that I think resonates more as we evolve as a company.”
Avalos: Keeping GitHub manager-free would have required far more bureaucracy
“If we had wanted to, and I'm not sure that we wanted to, we would have needed way more process, and way more bureaucracy than what we thought, ah, we had an appetite for. And that in some way, the lack of process, the lack of structure, leads to confusion with…”
Tucker: BlackLine would be dead if she took early bad VC advice
“Had I taken that advice, I doubt, and money, I doubt that Blackline would be here today.”
Siroker: Optimizely would have benefited early on from vertical focus
“If I had to give myself advice to a past version of myself, I think a lot about that, and I think about optimization. I think that it would have actually served us better to be more narrowly focused on a set of customers and deeply empathize with their biggest…”
Levie: Box would be a $25M business if it remained a departmental app
“We would be, I don't know, we'd be a twenty-five million dollar business. I mean, it would be a productivity app, and which is, like, completely nothing wrong with a productivity app, believe me but it would not have been able to be in a strategic conversation…”
Choi: HubSpot generated $11B in market cap from post-IPO new products
“And they had added essentially eleven billion dollars of additional market cap value that wouldn't exist if it weren't for these new products.”
Gabrisko: Databricks could have grown even faster with heavier early investment
“And if I had to give myself advice would have been invest even more early when you, I think we could have grew even faster.”
Divvy could have added billions to its $2.5B exit with earlier lessons
“If I could go back to that moment in, in 2018, with everything that, that we've learned along the way, we could have added more, we could have added a couple billion more dollars, I believe, to that eventual exit.”
Thomas: Loom probably should have verticalized its product in year five
“I think that we could have started going vertical sooner. I think we probably could have started doing that at year five or six versus year seven”
Lenta: VMware, AWS, and Databricks were destined to succeed inevitably
“All of the companies I've worked at, VMware, Amazon Web Services, and now I hope Databricks, they would have been successful with or without me. There was an inevitability. Customers were going to virtualize their data centers. People were going to consume tec…”
Atlassian regrets waiting until 2020 to switch from trials to freemium
“We went from a trial-based model to a free model, right?
Yeah, we did that in 2020.
It's like, actually, Matt, actually, we believe this has been a massive success for us.
We probably, knowing what we know now, we probably would have done that in like 2017.”
Patterson: Samsara would have failed in Mexico without localized GTM
“We really saw how we would have failed if we had just assumed that what we were doing here in the U S would work in Mexico.”
Liu: Launching Airtable directly against ServiceNow would have failed
“Had we launched out of the gates talking about, you know, taking on, let's say service now, it would have been a little bit ludicrous, right? Like it would have, you know just con completely I think over our customers or reporters or, you know, investors heads…”
Briggs: Firefly would have fared better focusing on UK product-market fit first
“And I think if we had really, really focused on, okay, what is our playbook in the UK to, you know, reach true product market fit and really, really figure that out, I think it would have been better.”
De la Nuez: UserZoom should have raised capital after three years
“Honestly, I think that if I could go back and do it again, the lesson I learned is that I, we could have raised maybe three to four years in, rather than seven years in. Because the problem with not raising is that you potentially miss opportunities, right?”
Stone: Grammarly should have documented why enterprise strategy could fail
“I think it's probably in retrospect probably would have been better if we'd even taken a stronger stance to write down the reasons why our current strategy to go into B to B and to go into enterprise would not work rather than allowing ourselves To be over opt…”
Awotona: Calendly would not have reached unicorn scale without PLG
“There's no doubt that I would not be sitting on this stage if Calendar did not, ah, you know, ah, use the PLG model. There's no doubt about that. I mean, we're, we've grown really fast because of that.”
Howie Liu: Airtable might have sold early under different investors
“I mean, I think with a different set of investors, we may not have made it right to where we are today. I think we might've gotten pressured to either sell out early or go down a more narrow path, compete more directly with project management tools.”
Liu: Airtable might have sold early under different investors
“With a different set of investors, we may not have made it right to where we are today. I think we might've gotten pressured to either sell out early or go down a more narrow path, compete more directly with project management tools.”
A $1M seed check in Podium would be worth over $200M
“The irony of that story is if that firm would have invested a million dollars into Podium at that time, today it would be worth over two hundred million dollars.”
Smith: Qualtrics wouldn't have targeted academia if it had venture capital
“If we would have had capital, we would have never gone after the academic market.”
Simons: Atlassian could have gone public two to four years earlier
“So I think we had the profile of a company that could've gone public two or three or four years earlier.”
Okta should have focused on its developer identity product much sooner
“Getting our product that was getting our product a plus to work perfectly for the developer was something if I had to do the last 10 years over and I would have done much sooner.”
De la Nuez: UserZoom should have invested in product marketing earlier
“Doing things simple when you're already at a hundred million, trust me, is a lot harder than doing it at the beginning. So my lesson, I guess, in this case is I wish I had done this earlier. I really wish I had done product marketing a little earlier, would ha…”
Schuck: ZoomInfo should have made bigger upfront bets on brand and content
“Along the way we didn't invest enough in brand awareness and content creation to have a voice. Those were longterm things that would pay off and we didn't invest in them upfront. And so we should, you know, we should have taken bigger bets along the way here.”
Porter regrets not expanding SalesLoft to enterprise and international markets sooner.
“One of the things is I didn't never expect that it would grow as the category would grow as fast as it has. And so I would have invested more money into it. I would have moved in enterprise sooner. I would have moved international sooner. I would have moved in…”
Brescia: Centralizing COVID decisions would have crippled GitHub's response time
“If I had made every single one of the decisions on how to respond across every aspect of our business, it would have taken far too long to execute, and our customers and employees would have been left wondering where we were and what we were doing. We could ha…”