Orlando Bravo’s second-biggest deal ever started with him writing a letter. Last year, the co-founder of private equity firm Thoma Bravo wrote to Boeing Co.’s top executives with a proposal: if they started a process to sell the company’s flight navigation unit, Thoma Bravo would be ready with a bid.
Making the first move worked out. Last week, Boeing announced the sale of its Jeppesen unit and other digital assets for $10.6 billion. The winning bidder among at least a dozen suitors? Thoma Bravo.
“Our philosophy is that the best time to buy a leading software company is when you can,” says Bravo, 54, in an interview. “For us, periods of dislocation have provided the best opportunities to buy.”
The dislocation he’s referring to — the market chaos sparked by US President Donald Trump’s global trade war — has brought much of the market for mergers and acquisitions to a standstill. While Bravo’s letter was sent before the US presidential election, final negotiations took place over the past few weeks.
At least one detail of the transaction reflected the tense environment: Thoma Bravo turned to private lenders to fund $4 billion of the deal’s value, according to people familiar with the matter, opting for more fixed terms than traditional bank lending would ordinarily allow.
Thoma Bravo newly completed Miami offices in the Brickell neighborhood of Miami. Photographer: Scott McIntyre/Bloomberg
Speaking at his Miami office a few weeks before the deal was announced, Bravo — who has a net worth of $13.7 billion according to the Bloomberg Billionaires Index — acknowledges that dealmaking has gotten harder.
“Exits and investments are certainly tougher now,” he says, echoing others in his industry who’ve been waiting on a Trump-fueled M&A boom that’s yet to materialize. While the Boeing assets are expected to be mostly tariff-proof, Bravo has other worries on his mind — not least regulatory uncertainty. Even after a deal is reached, the risk of capital being tied up for a year or more by a protracted antitrust fight is high, he says.
“It keeps me up at night because we have some control over some of these things,” he says, referring to in-house analysis that Thoma Bravo does to determine whether a deal might attract extra scrutiny. But under the Biden administration, even deals they’d expected to be straightforward were likely to be looked at, and it’s not yet clear whether Trump’s antitrust picks will change that approach.
Relentless research into a business is one way that Bravo addresses the uncertainty.
“If you cannot predict it, you cannot buy it,” he says, repeating the phrase like a sort of mantra. “You’re staring at that business again, and again, and again.”
Flagship Fund
In the next few weeks, Thoma Bravo is expected to announce that it has raised at least $22 billion for its 16th flagship fund, according to people familiar with the matter, as well as at least $7 billion for a separate fund focused on buying smaller companies.
Thoma Bravo’s two previous flagship funds were among the most active buyers during the post-pandemic dealmaking boom, striking multibillion-dollar deals for companies like Proofpoint Inc. and Anaplan Inc. Based on their internal rates of return, both funds are in the second quartile of comparable funds, according to data compiled by Bloomberg.
During the same period — as markets stabilized and interest rates sat near zero — Thoma Bravo also offloaded huge businesses, including selling mortgage software giant Ellie Mae Inc. to Intercontinental Exchange Inc. for $11 billion.
[Bravo, meanwhile, was making his own investments: In 2021, he and his wife Katy bought a $39 million Miami Beach mansion from singer Phil Collins.]
Even before Trump’s tariff plans sent markets spinning, the firm — like its rivals — was grappling with a very different dealmaking environment.
Tech valuations have tumbled, and pockets of distress for longer-held investments have some questioning whether private equity has learned the lessons of its overleveraged past. Interest rates remain stubbornly high.
The state of the market for initial public offerings tells the story of how quickly things can change. When Thoma Bravo took Sailpoint Inc. public in mid-February, shares in the already expanded listing priced at the top of their marketed range. Since then, they’re down more than 20%, and billions of dollars worth of other IPOs are on hold.
“On the exit front, the phone is certainly not ringing,” Bravo admits.
Apart from an early stint as an analyst in Morgan Stanley’s M&A department, where he worked under legendary banker Joseph Perella, Bravo has spent his whole career in private equity. His first job in the industry was working with Carl Thoma and Bryan Cressey — the T and the C in Chicago-based firm GTCR — when they struck out on their own with Thoma Cressey Equity Partners.
Bravo’s first deal there, for software provider Prophet 21, returned five times the firm’s money. That early success wasn’t immediately replicated.
“I was investing in venture-type deals that were leading to losses for the fund, including three back-to-back bad deals that would have otherwise ended my short career,” Bravo says. “Carl Thoma gave me another chance.”
Some 200 acquisitions later, Bravo’s firm has become a mainstay in software investing. Since the current iteration of the company was founded in 2008, it’s been involved in roughly a fifth of all private equity buyouts in the sector as measured by value, according to data compiled by Bloomberg. Over the same period, the wider software investing universe has boomed.
Thoma Bravo Deals Make Up About 20% of Software Buyouts
“We did our first software deal by training for it. It’s like tennis,” he says. “We played the little junior circuit, then the college circuit. And then we went up so many matches.”
Miami Move
The metaphor is apt for a man who, as a teenager, trained at a top tennis academy on the Gulf Coast alongside future pros like Jim Courier and Andre Agassi, and still starts most days with a few games. The training was what first brought Bravo to Florida from his hometown of Mayagüez, Puerto Rico, and means his move back to the Sunshine State was a sort of homecoming.
Bravo relocated to Miami from San Francisco in 2020, an early pacesetter for the great finance migration that also attracted Citadel’s Ken Griffin and activist investor Carl Icahn. He has a different perspective on the city that finance transplants have dubbed Wall Street South.
“I don’t see Miami as the next New York, the next Silicon Valley, the next London,” says Bravo. “I see Miami as Miami: a real, new center of commerce. It was definitely a big decision for us to open here and for me to move over, but I am convinced it was the right one.”
Now, with five offices across the US and one in London, Thoma Bravo manages about $179 billion in assets. Bravo’s stake in the firm, including his share of fund assets, is worth about $11 billion, according to Bloomberg’s wealth index.
Though the firm has grown, much about the way it operates has stayed the same. Bravo frequently refers to the value of mentorship and openly admits that he rarely does anything on his own. At Thoma Cressey he became “tied at the hip” to Scott Crabill, with the pair travelling together to every monthly board meeting.
It’s the same now, Bravo says, with investment professionals at Thoma Bravo always working in teams of two and relying on constant collaboration and communication. Bravo’s own squad is even bigger: in addition to Crabill, he’s close to partners Seth Boro, Holden Spaht and Lee Mitchell, creating a group that one private equity executive likened to a pack of wolves.
Bravo frequently refers to the value of mentorship. Photographer: Scott McIntyre/Bloomberg
The same executive recounted getting a call from Bravo about a deal — a business that Thoma Bravo was interested in buying. “Within the minute,” Bravo’s partners were calling both the company’s chief executive officer and the banker advising on the sale, the executive said.
It was Spaht who first introduced Bravo to Adena Friedman, the CEO of Nasdaq Inc., over a three-hour dinner at NYC mainstay Per Se in early 2023. Friedman says that even while Bravo exudes an “aura of optimism,” he clearly cares deeply about returns. Months after the dinner, Nasdaq agreed to buy Adenza Group Inc. from Thoma Bravo for $10 billion.
Now, with fundraising taking longer and getting harder, keeping limited partners — the investors that provide capital to a fund — onside is a crucial part of the battle for capital. Returning their money helps: Since the start of 2023, Thoma Bravo has sent $21.3 billion to investors, according to people familiar with the firm’s performance.
“The last 18 months has been time to sell,” Bravo says. “We couldn’t predict the market, but we were lucky that we got that much liquidity.”
“We appreciate the consistency of Thoma Bravo’s performance across cycles and their deep expertise in enterprise software,” says Hamad Shahwan Aldhaheri, executive director of the private equities department at the Abu Dhabi Investment Authority.
