Software Buyout King Orlando Bravo Attempts an AI-Era Reboot

Orlando Bravo was quick to see the disruptive potential of software, making a series of lucrative bets on the sector that turned him into a billionaire and transformed the buyout shop he leads, Thoma Bravo, into an industry powerhouse. Now, the disruption is coming for his own firm.

The Miami-based financier is confronting it head-on, seeking to ensure his empire is ready for the era of artificial intelligence — and reassure investors that a debt-laden bet on online customer surveys, which lost more than $5 billion, is a one-off. The fund that held the investment is lagging behind rivals, and investors are on ...