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 20 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
Better execution on Dropbox Paper could have prevented Notion's rise
“One can argue there if Dropbox paper Had, you know, maybe launched at a different time or a different way, there would be no notion, potentially.”
Oliver Jay: Dropbox could have eliminated Box with better enterprise execution
“I would say, there's a scenario where there is no box, and I think that was, Dropbox could have made that happen”
Jeff Shiner believes 1Password should have raised venture capital earlier
“Hindsight being twenty-twenty, I would have raised capital earlier.”
Notion would not exist if Evernote had executed on team-level value
“One can argue if they executed better, there would be no notion as well, right? But they just got stuck on the individual user value, and the team user value, like, they didn't really, it doesn't really, it didn't really resonate, right? The product didn't rea…”
Narkhede: Confluent probably would have failed if it started as SaaS-only
“Would it have just been feasible if we started with a SaaS only offering? And the answer is probably not because, you know, one of the most important things an open source company needs to do is quickly establish yourself as the market leader, quickly establis…”
Noronha: Gamma is 10x larger due to international expansion
“Going international has been huge for us. The AI app layer opportunity is so much broader than just a narrow segment of people, like, say, in the United States and the people right next to you. I think especially for a horizontal prosumer product like ours, it…”
Asthana: Open-sourcing Postman's UI would have bloated it with toggles
“So if we had open source, you would have a product with like You know, 30 buttons 70 toggles with, you know, 500 configuration options, and that just becomes a product not worth using.”
Younis: Applied Intuition would not be profitable with three well-funded competitors
“If we had three super well-funded competitors, you bet your bottom dollar, we're not a profitable company.”
Pivoting to enterprise B2B is significantly harder with consumer-focused venture funding
“But I do think going B to B would have been very challenging in an environment where we had had funding based on a consumer experience.”
Foster: Scaling from 10 to 100 employees would have ruined early Zapier
“As a first time founder, like if I tried to go 10 to a hundred, I think we would have ruined a lot of stuff inside the business.”
Shiebler: Waiting six months longer would likely have made Artemis too late
“I think that in, in retrospect, if we'd waited An extra six months or so, as we were originally discussing, then probably we may have ended up being too late, given the shape of the market, given the speed in which things are developing.”
Sekar: Single-Industry Feedback Would Have Confined Samsara to Compliance Apps
“Had we just focused on feedback from one industry, we would have ended up with a compliance app. Now we've got this, you know, really broad set of tools for frontline workers.”
Cramer: Sentry would never have reached current scale staying strictly open-source
“I think the problem is if we had waited years and we had just say worked on the open source version of Sentry, which is still exists roughly. It's self-hosted. I don't know. I don't think we ever would have gotten here.”
Busque: TaskRabbit launched five years too early for the market
“If you look about, you know, look at TaskRabbit, we were too early. Like we should have waited five years, followed on Uber or something like that. Like we could have done that a totally different way, but definitely some timing, right time, right place, solvi…”
Winters: Rover would have failed if it had not copied Wag
“Rover copied the model and wag ran into some operational execution issues at scale and Rover eventually took the lead on dog walking as well. But if they hadn't, we'd forget they even existed.”
Reshef: Webcollage would have fared better with founder-led sales for 5 to 10 customers
“So I wish we had said at a time like more founder led for the first five, 10 customers probably would have been in a much better shape because sellers are not as successful. They're not as knowledgeable, and then you don't get enough feedback.”
Blank: SpaceX would be out of business without intermediate steps
“If he said, I was just building a giant moon Mars rocket, I think he'd be out of business.”
Zima: Looker could have taken bigger risks aligning with dbt or acquiring
“And I think that we actually made some of those mistakes, even like, I think that we could have taken some big risks to align more closely with DBT or to acquire possibly, or to like move into different areas of the stack that we didn't do. Because we were com…”
Zapier launched in a narrow window between API availability and high competition
“If you tried to build a company like ours before, I don't think you have like all these APIs that you can go connect and do this stuff. Like most companies aren't building and doing stuff in this way. If you try and build it, you know, a year later, there's al…”
Siroker: Optimizely would have been far more successful picking one customer profile
“And had I chosen one or the other, it didn't even matter which one it was, we would have been massively successful one or the other. I mean, there's now huge companies that are, have been built and been successful by doing that. So I know we would have been mu…”