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 107 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
Assaraf: Coralogix would have shut down under a top US VC
“If our seed round was with like an American top VC, we would have shut down for sure. Like they shut us down. They won't even ask.”
Booth: Real estate would be deflationary without central bank easing
“It would look deflationary just like everything else. If you didn't have this, if you didn't have if you didn't have this, and then your savings would be going up and you would be able to buy more for everything would look like that. You would follow the natur…”
Jentzsch: I Wish I Had Known How to Avoid The DAO Bug
“So, I wish I would have known how to avoid the bug in the DAO.”
White: Fathom would have failed if transcription AI arrived later
“If transcription engines or like whisper and things come out a year later, we're probably dead.”
Martin: Raising venture capital would have eliminated founder lifestyle flexibility
“If I had raised venture money, I would have never been able to do the cool and fun stuff that I currently do now, me and my co-founder, because we can't just go fuck off to, you know, Fifi Islands for two months.”
Daneshgar: Modern Tools Make Early Marketplace Venture Capital Unnecessary
“The cardinal sin there is none of the three founders were technical, which by the way, like 10 years ago when I came out of the University of Chicago and we started out of there and like Grubhub or Etsy were just starting and you're building a marketplace busi…”
Singh: PAR Turnaround Would Not Have Been Easier Taking Company Private
“So I thought about that a lot, and I actually think the answer would be no, and I'll tell you why. The operational changes were extreme. We replaced almost the entire management team, you know, we shipped a bunch of jobs offshore, did a lot of crazy stuff, but…”
Reynolds: BriteCore would have scaled faster by raising venture capital earlier
“What I learned at the end of it, by the time I went and raised money was boy, I could have got a lot done a lot faster. Had I just gone out and raised money to begin with.”
Woodside claims MedStack's valuation suffered from being based in Canada
“And then the other thing is, you know, we're a Canadian company, so we don't get the Silicon Valley. If we were a Silicon Valley company, yeah, we would have it would be a different story, but you know what?”
Sheetgo founder regrets not raising significantly more capital in the US
“I think we should have raised money in the U S I live in Europe and I'm American, so we should have raised in the U S and a lot more capital for the kind of market we're going after.”
vFairs turned away business that could have doubled revenue to $60M
“We, in fact, had to turn away tons of business. You know, this thirty million could have easily been sixty million. I've been not caring about customer support.”
Early Square contractor rejected an equity offer now worth nearly $1B
“And what we offered him was a very generous offer. It would be close to a billion dollars today. You know, if he accepted our offer, he'd probably be a billionaire. And he didn't want it.”
Steer: Mode would have found product-market fit faster if super lean
“I wish we had gone super, super lean in the early days because I think we would have found the market faster.”
Supermetrics lost up to $100M in valuation due to COVID-19
“I think we lost at least fifty million, if not a hundred million in valuation.”
Santens: Bailing out homeowners in 2008 would have prevented mortgage securities from failing
“Like, we already know that buying up all these assets was something that vastly increased inequality and vastly Disproportionately, positively impacted, you know, asset holders. And we could have just bailed out the people, made sure that people could afford t…”
Latka: Without Federal Bailout, American Airlines Would Have Sold to Warren Buffett
“If the government passed, American Airlines would have ended up in the hands of someone like Warren Buffett, which I would argue is potentially a better situation for American taxpayers.”
Narowski says early VC funding could have made Karma CRM mainstream
“Had I done that early on, like, you know, kind of the typical rounds, not necessarily a small angel round we took and was able to really add gas to the fire five years ago, I think we could easily be one of the, you know, the common household names and people …”
Cushman: Kira Talent should have bootstrapped instead of raising venture capital
“Oh, never to raise VC money. I would have bootstrapped this from the start.”
Edgeless Could Never Have Raised $3 Million From Traditional VCs
“They would have never got that, that three million that it was at the time in February, March, March when they closed it, they would have never got that money from traditional VC.”
Bosworth: Duetto Would Not Exist Without Harvard MBA
“I don't think the company would exist without it.”
Zitoun: Submagic would need 40 to 50 employees without AI tools
“Like without AI, we should have been maybe 40 in the company or 50 people to do what we do.”
Hyrkin: Issuu would have fetched 2x-3x higher price in 2022 market
“Given the stage of where issue was when we sold it in July, if we had sold it two years prior in 22, we would have gotten two to three X what we got.”
Hyrkin: Raising equity in 2021 would have required a $1B exit
“So instead of raising, we would have had to raise thirty million on a two hundred and fifty million dollar valuation, which meant that For everyone to feel successful, we would have had to have a billion dollar exit, which may have happened, but I wanted to ma…”
Ganni: Venture-backed culture would have made retaining bootstrapped founders harder
“Had we been a massive venture-backed business that acquired a bootstrapped business, culturally, I think it would have been a bit more challenging to have the founders stick around, right?”
Volpini: WordLift would command $35M in SF versus €20M in Rome
“You know, in Europe, the evaluation are slightly lower. If we would be in San Francisco, that would be maybe a 35, but we are in Rome.”
Venture Funding Would Have Prevented Backblaze From Building Custom Hardware
“If we had raised a whole bunch of venture funding, we probably would have done it and said, we'll figure it out later. Somehow we'll figure out how to make the math work. But we didn't have any money. So we had to start from first principles and figure out how…”
Kagan: Hirize would have higher MRR if pricing was pre-negotiated in beta
“I started negotiating after after I launched, which I think we would have more MRR if we did it, if we, you know, yeah, you can't do everything perfect.”
Hurt: CoreMetrics Could Have IPO'd Instead of Selling Early to IBM
“Now, I will tell you that I wish that the CEO that took it forward didn't sell it so early. But you know, it had gone through some trauma. I mean, honestly, it could have been an IPO just a couple of years later.”
Brown: Remote could not maintain velocity if relying on meetings
“And if we had to have meetings to get something done or to make a decision, we would never be able to move at the pace that we need to move at.”
Ingram: Spending a year building Distro's initial product would have killed it
“In the first few months we started building product, within, I don't know, six weeks or so, we learned that what we had already built needed to be deleted. What if we had built that for a year? We would be done. We would have already missed the boat.”
Allouche: Delaying layoffs two months would have cost eight more jobs
“If I waited two months, like I was advised to, by pretty much everyone, then I would have had to lay off eight more people, seven to eight more people, because that's how the burn works, right?”
Ghibli regrets selling roughly 30% equity in friends and family round
“I do think that I've been a tiny bit generous
at my friends and family round, I think I should have given away less equity from the company when I did it.”
BloomTrack's founders would have accepted just $20,000 for the acquisition
“Honestly, they would have taken 20,000 for the deal.”
Osgood: Building point tools traps startups into local maxima via customer demand
“Cause like, for example, if we built Just the project management component of it. We would get sucked into building purely a project management tool for most of the life cycle of the company, because that's just where customer demand would end up pulling us. A…”
Andy Cook: I probably would have only raised $300K starting out
“If I were to start over again, I probably would have raised like 300 K maybe enough just to fund like, you know, life, maybe one other engineer, and they just kept it small and scrappy until we got to the point where we're making enough money just to fund it o…”
Jovtenko: RedTrack would have hit $1M ARR without Ukraine war
“And I mean, I'll be honest, if not, the one Ukraine would be there last three months were a bit rough for us.”
Baker: Holding previous startup 5 more years would have 10xed valuation
“I exited my last company way too early. And I think if, and it haunts me a little bit, I think if I'd held on for another four or five years, I would have probably 10 X the valuation I got out of my last company.”
Campbell: ProfitWell lost a year of growth by not raising a seed round
“We should have raised money right there, at least a small seed fund or seed round or something like that in order to like, you know, accelerate that probably by a year. Like we probably lost a year by not raising a small round for that.”
Owens: Paddle might have raised at a $3.5B valuation two months earlier
“Two months earlier and we might have raised it like a three and a half billion dollar valuation.”
Owens: The ProfitWell acquisition likely wouldn't have happened two months later
“Two months later, I think the deal might not have happened like at all.”
Extra VC Funding Cannot Replace 20 Years of Industry Experience
“So as the agency, I'd lived that problem for 20 years, and more funding wasn't going to help me You know, define the problem any better.”
Kellogg: Madwire Would Be at $120M-$130M ARR Without COVID-19
“If last year didn't happen, we'd probably be in the one 20, the 30 range right now.”
Earl: If starting over, he might raise venture capital early on
“And if I had to do it again, maybe I'd raise capital at the beginning.”
Smith: Delaying his September 2000 exit would have reduced value by two-thirds
“Honestly, if we had waited another year, probably would have got a third of that.”
Shaw: Better Agency could have achieved a higher valuation in a frothy market
“We could have totally have driven it higher. I mean, the market, you know, better than I do, the market's pretty frothy right now, and we could have driven it higher, but we were really, my biggest problem with fundraising was telling people no, and the reason…”
Teo Töpper admits Facelift sold too early and missed VC growth
“And I mean, if I look back, I think we sold too early.
Yeah.
Or we could have raised more to a fairly good valuation at that time.
And back then in 2017.
And I think we have grown much, we could have grown faster with more VC money inside.”