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.

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why aren't all 19 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 1 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

Insight
Bravo: Every company is worth only its future cash flows
“Look, we believe every company in the world, Is worth its future cash flows. We just come from that world. We don't believe in multiples of revenue. We don't believe in, ah, a technology may be worth a trillion dollars or a billion dollars because it might do …”
Orlando Bravo Feb 6, 2023 ▶ 3:36 Orlando Bravo: Raising Kids as a Billionaire; VC vs PE; Is Warren Buffet Wrong? | 20VC #974 · 20VC with Harry Stebbings
Prediction Not checkable as stated
Clements: Private equity firms will acquire overvalued 2021 tech startups
“I think it's probably a good time to be in the LBO business. I think it's probably a good time to be in the Toma Bravo Vista Blackstone KKR business. There will be homes for a lot of those companies, you know, who get themselves to a sustainable place and they…”
Miles Clements Mar 9, 2026 ▶ 41:02 "Cursor is Dead" is Total BS: Here is Why | Miles Clements · 20VC with Harry Stebbings
Insight
O'Driscoll: 8% of an IPO-bound company beats 20% of a non-public startup
“Yeah, 20% of something that's not going public is not nearly as interesting as 20, as eight percent of something that is going public, right? And if you believe that it's not a continuum of value, you know, a sliding scale of value, but rather it's a, it's lik…”
Rory O'Driscoll Oct 2, 2025 ▶ 1:03:48 Are Burn Multiples BS in an AI World? & Sam Altman Needs $1TRN of Energy · 20VC with Harry Stebbings
Prediction Not checkable as stated
Lemkin: Software expanding to 4% GDP will create 100+ decacorns
“I do believe if this trend of software going from two percent to four percent of GDP that they point out, that, that's going to birth a hundred decacorns, a hundred or more, and it is the golden age of software.”
Jason Lemkin Apr 3, 2025 ▶ 5:12 20VC: The Daily Deal: Coreweave IPO | Scale Hits $25BN on $2BN EOY Revenue | Sequoia's 25x Return on Wiz | Tech Stocks Tank with Tariffs | Cursor: Defensible or Dangerous Example of Lost Moats in Tech
Disclosure
Bravo: Thoma Bravo requires 100% unanimous consensus on all deals
“We don't do any controversial deals. We are. 100%. Everybody consents. If somebody really has a problem with that deal, there's something really wrong. Once again, we've worked together, all of us, for almost 20 years. We're looking at the same industry. We ha…”
Orlando Bravo Feb 6, 2023 ▶ 41:58 Orlando Bravo: Raising Kids as a Billionaire; VC vs PE; Is Warren Buffet Wrong? | 20VC #974 · 20VC with Harry Stebbings
Disclosure
Bravo: Thoma Bravo avoids IPOs because cash-generative companies avoid dilution
“I mean, in our history, we have mainly exited to strategics and other financial buyers. And there's a reason for that is the IPO for our companies doesn't give us that much in itself because our companies generate the cashflow that is needed to fund their inve…”
Orlando Bravo Feb 6, 2023 ▶ 31:43 Orlando Bravo: Raising Kids as a Billionaire; VC vs PE; Is Warren Buffet Wrong? | 20VC #974 · 20VC with Harry Stebbings
Assertion Supported
Bravo: Increased fund size directly correlates with reduced investment performance
“The LP community is really, really smart. And there is a direct correlation between that, that we cannot argue with. And it is there.”
Orlando Bravo Feb 6, 2023 ▶ 34:56 Orlando Bravo: Raising Kids as a Billionaire; VC vs PE; Is Warren Buffet Wrong? | 20VC #974 · 20VC with Harry Stebbings
Insight
Bravo: PE firms cannot triage underperforming portfolio investments like VCs
“There's no such thing in buyouts and private equity as triaging your portfolio and deciding what you throw away and when you keep going, which in another way to put it is, is actually a big motivator to management teams to partner with you because you have no …”
Orlando Bravo Feb 6, 2023 ▶ 28:49 Orlando Bravo: Raising Kids as a Billionaire; VC vs PE; Is Warren Buffet Wrong? | 20VC #974 · 20VC with Harry Stebbings
Insight
O'Driscoll: LPs will forgive PE firms for one bad fund, but not two
“I don't think someone's going to say, you know, Tomo Bravo, one of these guys, you're an idiot forevermore. Because you did that dumb thing, right? They're probably not. They're going to say, Ooh, that funds up. Now you put two funds back for our conversation.…”
Rory O'Driscoll Apr 17, 2025 ▶ 22:47 a16z's $20BN Fund & Founders Fund's $4.6BN & Why Josh Kushner Has Mastered the Game · 20VC with Harry Stebbings
Insight
Bravo: A $10B buyout mistake is fatal, unlike early VC checks
“In a buyout, you could be writing a ten billion dollar equity check with your partners, and you cannot get that wrong. That would be really fatal, making a mistake on something that big, which is an interesting disconnect sometimes between the technology world…”
Orlando Bravo Feb 9, 2024 ▶ 15:50 20VC: Doug Leone, Bill Ackman, Bill Gurley and Orlando Bravo on "Does Price Matter"; When to Pay Up vs When to Stay Disciplined, The Biggest Lessons on Price Discipline from 8 of the World's Best Investors
Disclosure
Bravo: Thoma Bravo requires target company inefficiency to drive excess returns
“Give us enough inefficiency so we can earn a differentiated return. If you have a perfectly run business, then it's going to sell for a retail value on that cash flow, and we may not have enough delta to create an additional return from our efforts and from ou…”
Orlando Bravo Feb 6, 2023 ▶ 23:37 Orlando Bravo: Raising Kids as a Billionaire; VC vs PE; Is Warren Buffet Wrong? | 20VC #974 · 20VC with Harry Stebbings
Assertion Contradicted
Lemkin: Thoma Bravo generated $30 billion in distributions last year
“Tom O'Bravo had, had thirty billion dollars in distributions last year. Thirty billion dollars. I think that exceeds most guests, right? Thirty billion in distributions, not paper markups, but distributions.”
Jason Lemkin Jun 5, 2025 ▶ 1:43 Is DPI The Only Thing That Matters? with Sam Lessin, Jason Lemkin & Rory O’Driscoll · 20VC with Harry Stebbings
Assertion Partly supported
Jason Lemkin: Thoma Bravo raised $35B fund for B2B acquisitions
“I know we glossed over it in the beginning, but I do think Tom O'Bravo raising a record fund this week is a good sign too. That's thirty-five billion dollars to buy B to B companies, almost entirely B to B, right?”
Jason Lemkin Jun 5, 2025 ▶ 1:16:56 Is DPI The Only Thing That Matters? with Sam Lessin, Jason Lemkin & Rory O’Driscoll · 20VC with Harry Stebbings
Disclosure
Bravo: One-third of management committee works directly on each deal
“And we try, what we try to do is, actually what we do is we have at least a third of the management committee Be involved in that deal day to day. And therefore you have two leaders and two senior partners that can talk about it and are living that journey whi…”
Orlando Bravo Feb 6, 2023 ▶ 41:30 Orlando Bravo: Raising Kids as a Billionaire; VC vs PE; Is Warren Buffet Wrong? | 20VC #974 · 20VC with Harry Stebbings
Assertion Not checkable as stated
Bravo: Critics claim Thoma Bravo overpaid on almost every deal
“And I almost cannot tell you of a deal where a peer or competitor or an outsider, I cannot almost say one single deal where they haven't criticized us for paying too much. It's truly, truly amazing. So Coupa Anaplan and whatever other investments are no except…”
Orlando Bravo Feb 6, 2023 ▶ 30:14 Orlando Bravo: Raising Kids as a Billionaire; VC vs PE; Is Warren Buffet Wrong? | 20VC #974 · 20VC with Harry Stebbings
Prediction Open · timeframe Feb 2028
Bravo: Thoma Bravo targets 12 to 15 portfolio companies per fund
“Per fund, we'd like to have 12 companies, maybe 15.”
Orlando Bravo Feb 6, 2023 ▶ 36:34 Orlando Bravo: Raising Kids as a Billionaire; VC vs PE; Is Warren Buffet Wrong? | 20VC #974 · 20VC with Harry Stebbings
Insight
Bravo: Competitive deals are never over even if trailing on price
“I tell myself when working on a competitive investment situation in which there is another suitor for the company or many, the deal isn't over. You could be losing. You could be behind on price. You could be losing something. Maybe your operating plan is not y…”
Orlando Bravo Feb 6, 2023 ▶ 10:56 Orlando Bravo: Raising Kids as a Billionaire; VC vs PE; Is Warren Buffet Wrong? | 20VC #974 · 20VC with Harry Stebbings
Assertion Not checkable as stated
Bravo: Thoma Bravo holds four-hour monthly board meetings for all companies
“We meet with our companies monthly. Our board meetings are monthly from eight to noon on every one of these entities.”
Orlando Bravo Feb 6, 2023 ▶ 37:26 Orlando Bravo: Raising Kids as a Billionaire; VC vs PE; Is Warren Buffet Wrong? | 20VC #974 · 20VC with Harry Stebbings
Insight
Bravo: Turnarounds require breaking problems down, measuring, and delegating
“What we would do, and what he would always tell us to do, is measure. Take a big problem and divide it into many component parts. Prioritize which parts are more important And then within those parts, measure where you are and begin the journey towards improvi…”
Orlando Bravo Feb 6, 2023 ▶ 5:53 Orlando Bravo: Raising Kids as a Billionaire; VC vs PE; Is Warren Buffet Wrong? | 20VC #974 · 20VC with Harry Stebbings
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