Stanford GSB: View From The Top S8E1: Orlando Bravo on Doing the Work, One Deal at a Time
Nov 19, 2025
Orlando Bravo, founder of Thoma Bravo and Stanford JD/MBA alum, shares his inspiring journey from setbacks in private equity to leading one of the industry's giants. He discusses pivotal moments, such as a near-career-ending dot-com bust and his transition to software buyouts. Orlando emphasizes the value of mentorship, hinting at the importance of persistence and humility in achieving success. He also explores the impact of generative AI on software investments and advocates for focus and authenticity in fundraising. A compelling blend of lessons and insights!
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From Dot‑Com Disaster To A Second Chance
- Orlando described early dot-com deals where two of three investments went to zero and one returned half the capital.
- Carl Thoma gave him one more chance, which led to proposing software buyouts and a career turnaround.
Keep Applying Until The Right Fit Appears
- When you face rejection, keep applying and cold‑reach until you find the right fit.
- Orlando sent hundreds of resumes and emphasizes you only need one right offer, not many.
Test Big Ideas With Small, Fundable Bets
- Pitch contrarian, high‑conviction ideas if existing approaches fail.
- Orlando pitched software buyouts as a small, low‑cost experiment and scaled from a $50M first deal.