Inside Orlando Bravo’s Private Equity Playbook: How to Build a Top Firm

Bravo says Carl Thoma nearly fired him after his 1997–2000 mistakes; the second chance pushed him toward established software with recurring revenue, then unusually cheap. That niche evolved into growth-style buyouts, typically about 70% equity and 30% debt, where most returns now come from terminal-value appreciation rather than cash yield.

AI is already shrinking Thoma Bravo’s investable software universe, not merely creating upside. Bravo says many verticals are too disrupted or confusing to underwrite, even as long-time institutional investors still want consistency and predictability from the firm.

Scale is becoming Thoma Bravo’s harder problem: a $10 billion acquisition may need to become worth roughly $25 billion to generate the desired return. Bravo says an IPO exit can begin at a major disadvantage because the firm may buy at a 30% premium yet have to float at a discount.

Thoma Bravo’s $10.5 billion Boeing carve-out centers on Jeppesen, a flight-navigation business Bravo describes as indispensable to airlines; roughly 15 private-equity groups competed. The thesis is operational: lift margins from about 25% toward 50%+ by running it more like a software company.

Thoma Bravo often plans roughly 15% cost cuts at closing, then shifts attention to bookings growth and add-on acquisitions. Bravo’s model is to turn a 6–7× revenue purchase into an EBITDA-valued business by year four, ideally with 20% growth and 50% margins.

Thoma Bravo’s information edge often comes from following targets for years and already owning a competitor or partner before bidding. For the $12.5 billion Dayforce deal, partner Holden Spade first met the CEO in 2008, giving the firm a long history with the company before the transaction.

Despite managing $179 billion, Bravo says Thoma Bravo has no reason to go public because listing does not help it raise capital, buy companies, or improve them. Carl Thoma gave the firm to Bravo and his partners, and Bravo wants to repeat that succession model rather than cash out.

Bravo publicly endorsed Puerto Rican statehood for the first time in the conversation. He said statehood would be better for Puerto Rico if the United States allows it, noting that the pro-statehood party has grown while some commonwealth tax advantages have disappeared.