Orlando Bravo’s Approach to Mentorship

Authored by Orlando Bravo

Over the course of my life and career, I’m fortunate to have had the support and guidance of so many people. My first mentors were my father and grandfathers in my hometown of Mayagüez, Puerto Rico, who taught me the importance of work ethic, organization and helping those in need. Then I met coaches who guided me through the countless practices, matches and tournaments typical of a junior tennis career. They taught me early on to listen, perfect my approach, and learn to love the competitive dance with each opponent I faced. Later in life, Carl Thoma stepped in to show me the ropes of private equity, teaching me professional lessons that continue to shape my career to this day. As I reflect on my personal and professional life, it’s impossible to understate the impact each one of these individuals has had – their influence is everywhere.

Perhaps most importantly, my mentors have inspired what I consider my life’s work: to provide meaningful opportunities for young, talented adults - from the SEO (Sponsors for Educational Opportunity) college students exploring summer internships across Thoma Bravo portfolio companies to recent university grads launching startup companies in Puerto Rico (Bravo Family Foundation and the Rising Entrepreneurs Program). I know from my own experience that sometimes all it takes for your life to change is for someone to take a chance on you.

That same culture of mentorship is one of my favorite parts of showing up to work at Thoma Bravo every day. I believe it is one of the reasons we’re able to attract and retain the very best people, which is the most important part of delivering long-term results for our investors. Because the biggest entry point for investment talent at Thoma Bravo is at the Associate level, we take care to retain and develop junior team members and prefer to promote from within whenever we can. In fact, many of our Partners, like Andrew Almeida, Chip Virnig and Robert Sayle, started out as Associates. These success stories are only made possible when senior members of our team, Principals and Vice Presidents, take the time to mentor new Associates – just like Carl Thoma did for me all those years ago.

Being an effective mentor can be both fulfilling and challenging. Over the years I’ve learned five lessons helpful for anyone interested in serving as a mentor to someone new: 

1. Lead by example: As a mentor, assume your mentee is watching you even more carefully than they’re listening to you. In other words, “do as I say, not as I do” won’t work in a healthy mentor/mentee relationship. When you come across an opportunity to take action, at work or outside of it, ask yourself what advice you would give your mentee if they were in your position. If you would encourage them to do it, so should you! When Hurricane Maria devastated Puerto Rico in 2017, I watched and waited for government agencies, nonprofits, and politicians to take action. When I realized that help wasn’t coming, I did what I often encourage my mentees to do – I rolled up my sleeves and figured out how I could make it happen myself, which ultimately led to the start of the Bravo Family Foundation.
2. Understand motivation: When I first started out in banking, I found I was frequently assigned to the LatAm desk because of my Puerto Rican background, even though what I was passionate about was software. Carl Thoma was the first person to give me the chance to focus on software investing, an opportunity that changed my career. The only way to get to know your mentee’s true ambitions and motivations is to ask – so ask, even when the answer seems obvious based on their current team or prior experiences. 
3. Empower through delegation: I’ve found that when you give talented people real responsibility and a chance to prove themselves, they usually exceed expectations. We’ve kept the investment team at Thoma Bravo relatively small over the years for one reason: we believe in giving even our newest Associates ample opportunity to step up and contribute meaningfully to investment decisions.
4. Give second chances: As a mentee, it’s inevitable: your mentor gave you all that responsibility and authority, and now you’ve made a mistake. When you’re a mentor, it’s important not only to expect those slipups, but to be generous with offering second chances in response. As Carl Thoma used to say to me, it’s okay to make a mistake, as long as you don’t make the same one again.
5. Learn from your mentee: It’s not just mid-level professionals who benefit from the mentoring process! I am always amazed by how much I can learn from listening to my younger colleagues. Never underestimate the talent and potential of younger people and what they can teach you.

I’m so grateful for all the advice, support and guidance the mentors in my life have given me. I’m excited to do the same for the next generation of talent by continuing to always look for opportunities to open doors for others.

Thoma Bravo Managing Partners and Co-Founders, Orlando Bravo and Carl Thoma.