Finding Your Niche | Orlando Bravo | E16

From a small town in Mayagüez, Puerto Rico to leading Thoma Bravo—one of the world’s largest software investors with $130B+ AUM—this is the extraordinary journey of Orlando Bravo. In this exclusive conversation, host Randall Kaplan unpacks the mindset, operating system, and playbook that made Bravo a billionaire investor, visionary leader, and philanthropist.
If you’re searching for how private equity really works, how to evaluate software companies, deal discipline, leadership under pressure, and what excellence looks like at scale, this episode is a masterclass.

What You’ll Learn
Origin → operating system: How Puerto Rico shaped Orlando’s values, drive, and judgment.
Athlete to investor: From junior tennis champion to Wall Street dealmaker.
Thoma Bravo playbook: Sourcing, underwriting, and scaling high-growth software businesses.
Winning advantages: Discipline, patience, focus, and repeatable value-creation.

Founder mistakes: The biggest traps entrepreneurs fall into—and how to avoid them.
Leadership & culture: Building teams that execute, learn, and compound results.
Success & meaning: Orlando’s definition of happiness, legacy, and giving back.

Chapters
00:00 – Intro & Orlando’s origin story
02:35 – Growing up in Puerto Rico
08:12 – From tennis to finance: the turning point
14:45 – Breaking into private equity
20:30 – Founding Thoma Bravo & early wins
28:55 – How to evaluate billion-dollar opportunities
37:10 – Overcoming challenges & staying resilient
44:25 – Defining success beyond money
51:05 – Advice for young entrepreneurs
57:30 – Final thoughts on excellence

About Orlando Bravo
Orlando Bravo is the Co-Founder and Managing Partner of Thoma Bravo, one of the world’s largest private equity firms with more than $130 billion in assets under management. Recognized by Forbes as the most successful private equity investor in history, he’s renowned for revolutionizing software investing, leading transformational acquisitions, and making significant philanthropic contributions in education, healthcare, and disaster relief.

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