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Orlando Bravo

Founder & Managing Partner, Thoma Bravo · 1 appearance on the record, plus 2 compilation re-airs.

computed by AI from the episodes · how this works → · full disclaimer →

investorfounderexecutive@OrlandoBravoTB ↗LinkedIn ↗thomabravo.com/team/orlando-bravo ↗Wikipedia ↗Instagram ↗

Orlando Bravo is a Founder and Managing Partner of Thoma Bravo. He directs the firm's investment strategy, pioneering software-focused private equity buyouts and overseeing more than 420 software acquisitions.

23statements → 7claims → 4claims resolved → 100%fully supported → 4.27/5average certainty → 2.27/5average debate potential → 4.4/5argument clarity · the sources → 12said about them ↓

4 supported 0 partly supported 0 contradicted 1 not yet assessed 2 not checkable as stated how the 7 claims stand · each chip opens the sources

2 predictions · 5 assertions · 1 opinion · 10 insights · 5 disclosures · every statement was checked. The predictions and assertions are the 7 claims: statements the public record can support or contradict. 4 are resolved, 1 is not yet assessed, and 2 name no date, number or outcome precise enough to check. Everything else (opinions, insights, what ifs, disclosures) can never be settled by the record, so it carries no assessment.

The record, in short

What the tape says about how Orlando argues and how the claims held up. Everything they said, and everything said about them, is in the tabs below.

Their most notable supported claim

Prediction Held up
Bravo: Lower tech market valuations represent the new normal for years
“So if I, if you really push me, I would say, yes, this is the new normal, because I don't see investors jumping in in mass To do the same thing that in the last 18 months lost them 80% of their money. At least not in the next few years.”
Orlando Bravo Feb 6, 2023 ▶ 16:51 Orlando Bravo: Raising Kids as a Billionaire; VC vs PE; Is Warren Buffet Wrong? | 20VC #974 · 20VC with Harry Stebbings

Expressed certainty vs assessment result

none yet certainty 1
none yet certainty 2
100% certainty 3
100% certainty 4
100% certainty 5

weighted support: a fully supported claim counts one, a partly supported claim counts half. Each filled bar is clickable and opens exactly those claims; "none yet" means nothing said at that certainty level has resolved yet

Argument clarity: do they answer the question? how? →

4.4 / 5 directness 4.6 · coherence 4.7 · precision 4 · compression 3.9

redirected or did not address 2 of 41 assessed questions (5%). Watch them ▸

This is a score against a rubric. It is not a rank. Every host question → answer exchange is scored with names hidden on directness, coherence, precision and compression, 1–5 each, on meaning alone: disfluencies are ignored, and only raw unedited episodes count. This is the score that measures thought. Every scored exchange, scores shown → · The rubric and its checks →

How they sound: speaking style how? →

237 words/min while actually speaking · 8.5 um and uh per 1k words · 20.6 false starts per 1k · 26.7% of pauses land inside a clause

English is their second language (first language: Spanish). These numbers measure fluency in English. They do not measure thought; the argument clarity score above is read from substance alone.

Measured by listening to the audio itself: 7,507 words across 1 episode of raw-level tape, transcribed verbatim with every um and uh kept, each one attributed only where the alignment onto our timed stream is unambiguous. These are measurements of speaking style. We do not rank them: across this corpus, fluency and argument quality are nearly uncorrelated (ρ≈0.2), and smooth talking does not signal clear thinking. How it's measured →

How the interview went all their pushback → series average →

Across 3 rated episodes:

host pushback ▾ 2.7/10
pushed back at the host ▾ 1.7/10
setup questions received 63%

Everything Orlando Bravo said on 20VC that made the record, most notable first. Filter by type, assessment or year in the ledger →

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
Insight
Bravo: Supporting 40 to 50 portfolio companies operationally is impossible
“If you have an investor, private equity or venture firm, that claims that they make a big difference in their companies, that they're there with those companies operationally, that they change them in a positive way. And you have 40 or 50, there is no way you …”
Orlando Bravo Feb 6, 2023 ▶ 36:39 Orlando Bravo: Raising Kids as a Billionaire; VC vs PE; Is Warren Buffet Wrong? | 20VC #974 · 20VC with Harry Stebbings
Prediction Held up
Bravo: Lower tech market valuations represent the new normal for years
“So if I, if you really push me, I would say, yes, this is the new normal, because I don't see investors jumping in in mass To do the same thing that in the last 18 months lost them 80% of their money. At least not in the next few years.”
Orlando Bravo Feb 6, 2023 ▶ 16:51 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
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
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
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
Assertion Supported
Bravo: Unprofitable software forward revenue multiples dropped from 17x to 3.5x
“The revenue multiples on those have gone from an average of 17 times forward to 3.5 today.”
Orlando Bravo Feb 6, 2023 ▶ 16:00 Orlando Bravo: Raising Kids as a Billionaire; VC vs PE; Is Warren Buffet Wrong? | 20VC #974 · 20VC with Harry Stebbings
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
Insight
Bravo: Greater operational efficiency accelerates software business growth
“In our world, the more efficient you are, the faster you should grow.”
Orlando Bravo Feb 6, 2023 ▶ 24:39 Orlando Bravo: Raising Kids as a Billionaire; VC vs PE; Is Warren Buffet Wrong? | 20VC #974 · 20VC with Harry Stebbings
Insight
Bravo: The best-run tech companies with 40% cash flow margins win
“What we can control is having the best run company in that field. And when times get really bad, the best run company always wins. Because then you'll have 40% cash flow margins. You're very well put together. You're budgeting conservatively. You're not missin…”
Orlando Bravo Feb 6, 2023 ▶ 33:45 Orlando Bravo: Raising Kids as a Billionaire; VC vs PE; Is Warren Buffet Wrong? | 20VC #974 · 20VC with Harry Stebbings
Insight
Bravo: High-margin, unprofitable software companies make prime buyout targets
“The more we studied these companies, the more we realized the recurring revenues are really strong, but none of them were making money. So we developed an approach that said, no, with 90, 80% gross margins, like today, these companies can be buyout candidates …”
Orlando Bravo Feb 6, 2023 ▶ 1:11 Orlando Bravo: Raising Kids as a Billionaire; VC vs PE; Is Warren Buffet Wrong? | 20VC #974 · 20VC with Harry Stebbings
Opinion
Bravo: Most software companies fail to segment costs for profitable growth
“We see even today the world of software, which are much better innovators today than they were 10 years ago, than they were 20 years ago, but these businesses mainly have a big bucket of revenue and a big bucket of cost, and they don't really separate their ac…”
Orlando Bravo Feb 6, 2023 ▶ 6:23 Orlando Bravo: Raising Kids as a Billionaire; VC vs PE; Is Warren Buffet Wrong? | 20VC #974 · 20VC with Harry Stebbings
Disclosure
Orlando Bravo was almost fired from his PE firm in 1999
“I felt that my career was a failure in 1999. I had come out of Stanford Business School and Law School. With what I thought was this like blue chip, pristine, right? Education and resume. And I had very high expectations of myself and a timeline for which I ne…”
Orlando Bravo Feb 6, 2023 ▶ 8:44 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: 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
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
Insight
Bravo: Philanthropy is hard because foundation budgets contain only costs
“When I go through the budget of a company, you see this hopefully wonderful earnings coming out from all the work, and you have revenue and cost, and you can measure that. When you do a budget for your foundation, you only have cost.”
Orlando Bravo Feb 6, 2023 ▶ 58:46 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
Assertion Supported
Bravo: Profitable software trades at 25x forward P/E versus S&P's 16.5x
“If you look at the public market as a benchmark for the world, and you take an index of the profitable software companies, those companies that have margins in excess of 20%, and you put them all together, on average, They trade for around a 25 forward PE, whi…”
Orlando Bravo Feb 6, 2023 ▶ 14:41 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

The other half of the tape: Orlando Bravo's own voice is left out of every number here. Other people bring the name up 12 times in 6 episodes on 20VC. every mention, with the transcript →

Who brings them up most Harry Stebbings 10Jason Lemkin 2

Every mention by year

tap a year for its mentions
0032642023202420252026episodesmentions
0242023202420252026episodes it came up in
0022442023202420252026episodesmentions per episode
2026 6 mentions in 4 episodes 2 per episode
2025 4 mentions in 1 episode
2023 2 mentions in 1 episode

Appearances (3)

EpisodeDateSpeaking time
20VC: Doug Leone, Bill Ackman, Bill Gurley and Orlando Bravo on "Does Price Matter"; When compilation Feb 9, 2024 54s
20VC: What are the World's Tech Leaders Running From? Fear? Insecurity? Poverty? What Driv compilation Jun 9, 2023 1m
Orlando Bravo: Raising Kids as a Billionaire; VC vs PE; Is Warren Buffet Wrong? | 20VC #97 Feb 6, 2023 41m
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