Orlando Bravo
Founder & Managing Partner, Thoma Bravo. On 3 shows, 4 appearances, plus 2 compilation re-airs not counted. The Shows tab opens the full record on each.
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.
3shows
4appearances
69statements
12resolved
9supported
1contradicted
75%fully supported
16said about them ↓ Everything Orlando Bravo said on any show that made the record, most notable first. Each card names its show and opens the statement there.
Bravo: Puerto Rico would be better off becoming a U.S. state
“I'm gonna say something I've never said before, and I do believe it'll be better for Puerto Rico to be a state if the U.S. Would allow that.”
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 …”
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 …”
Bravo: Modern PE software returns derive from terminal growth, not yield
“About two thirds or more is terminal value appreciation, and you make very little. On your yield.”
Bravo: AI poses a major disruption risk to many software verticals
“There is a big risk of AI in this business. I mean, in a big, big way. There's so many verticals that are going to get disrupted.”
Bravo: Any company can cut 10% of costs, but 20% is difficult
“No matter how profitable you are, you can always cut 10%. No matter how unprofitable you are, it's difficult to cut more than 20%.”
Bravo: Low customer support gross margins reveal a flawed software product
“Like, for example, a company cannot say that it has really, really good product if its gross margins on support are very low.”
Bravo: Thoma Bravo makes more money backing internal successors than going public
“And we actually feel we'll make more money by investing behind the next generation when that time comes than by going public and having a great day and a great multiple.”
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.”
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 …”
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…”
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.”
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…”
Missing Targets Opens the Door for PE Sponsors to Guide Management
“So sometimes it's good that they miss numbers because it gives us an opening to have them listen to us and become more open-minded.”
Thoma Bravo Now Operates as a Growth Investor in SaaS
“We are really growth investors in companies where you can add significant value to your product ongoing because you have to. If not, you'll be displaced by another SaaS solution.”
SaaS Is Less Sticky Because Customers Avoid Upfront Capital Expenditures
“It's not as sticky as maintenance was because the customer hasn't made the capital expenditure.”
Thoma Bravo Would Be Larger Than SAP If It Never Sold Companies
“Now, in hindsight, based on where software has gone, we should have held all the companies. And if we would have done that, we would have been much larger than SAP.”
Sell When Strategic Buyers Approach Because They Will Not Ask Twice
“When a strategic approaches you, look to sell, because they won't approach you again. They'll either build the product internally or buy somebody else.”
High Software Valuations Act as a Barrier to Entry for Generalist Buyouts
“The fact that valuations have been high, some claim too high, Actually, it's a barrier to entry. It keeps big players that could be new players or new entrants out of this market. There should be 20 or 30 private equity firms doing large buyouts and software. …”
Bravo: Software companies should not be held long-term by one group
“These software companies are not meant to be owned by the same group for 30 or 40 years.”
Bravo: Enterprise AI adoption will take time because enterprise tech is evolutionary
“In the enterprise, it's going to take a while, because we always say technology is evolutionary, not revolutionary, because our customers are buying this stuff for cost.”
Bravo: Thoma Bravo must exit $10B deals at $25B to make money
“But now we're doing ten billion dollar deals. We have to sell those for 25 to make money.”
Bravo: Thoma Bravo cuts costs once then focuses on growth and add-ons
“So the reason we like to take out the cost once is the rest is about bookings, growth and add ons. We don't want to revisit margin too much. We want profitable growth going forward.”
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…”
The other half of the tape: Orlando Bravo's own voice is left out of every number here. Other people bring the name up 14 times in 8 episodes across the shows. 2 statements on the record name them. every mention, with the transcript →
Who brings them up most Harry Stebbings 10Jason Lemkin 2Jennifer Prosek 1Jason Calacanis 1
Statements about Orlando Bravo, by other people (2)
Palihapitiya: Thoma Bravo raised $34.4B across fund vehicles in June
“In June, you raised 34.4 billion dollars in basically like a set of fun vehicles”
Every mention by year
tap a year for its mentions
20VC 12
Capital Allocators 1
All-In 1
2026 6 mentions in 4 episodes 2 per episode
- Anthropic Raises $45B but Falls Short on Compute & Thoma Bravo Hand Back Medallia Keys to Creditors · 20VC with Harry Stebbings
- The SaaS Apocalypse: Who Lives & Who Dies | Insight Partners Co-Founder, Jerry Murdock · 20VC with Harry Stebbings
- The AI Bubble WILL Burst | Should we be fearful of Chinese Open-Source | Jerry Murdock
- Marc Andreessen: Will a16z Go Public & Why Labour Displacement with AI is Wrong? · 20VC with Harry Stebbings
- every mention in 2026, scene by scene →
2025 5 mentions in 2 episodes 3 per episode
2024 1 mention in 1 episode
One line per show, most statements first. The link opens Orlando's full record on that show: the calibration, argument clarity, speaking style and every statement made there.
| Show | Role there | Eps | Statements | Record | |
|---|---|---|---|---|---|
| CAPITAL ALLOCATORSLEDGER | Founder & Managing Partner, Thoma Bravo | 2 | 31 | 100% 5/5 | full record on Capital Allocators → |
| 20VCLEDGER | Founder & Managing Partner, Thoma Bravo | 1 +2 | 23 | 100% 4/4 | full record on 20VC → |
| ALL-INLEDGER | Founder & Managing Partner, Thoma Bravo | 1 | 15 | 0% 0/3 | full record on All-In → |