Orlando Bravo

As a teenager, Orlando Bravo aspired to play professional tennis, training with future stars Andre Agassi and Jim Courier. Wall Street wasn’t part of the original plan. The journey from his native Mayaguez, Puerto Rico, to become one of the world’s leading private equity investors was far from preordained. “It took a lot of luck, help, and opportunities,” Bravo says.

But once there, Bravo brought an entrepreneurial mindset — inspired by his time at Stanford — and set out applying private equity principles to software companies. For his prowess in the software as a service sector, the Financial Times has called him “The King of SaaS” and Forbes named him “Wall Street’s best dealmaker” in 2019.

His journey shows how two different passions can harmoniously shape one’s career, as Bravo holds dear two people who had major influence on his life: Antonio Ortiz, his tennis coach growing up, and Carl Thoma, founder of the private equity firm that would later become Thoma Bravo.

Today, as founder and managing partner of Thoma Bravo, Bravo splits his time between Miami, where he lives, and Puerto Rico, where he runs the Bravo Family Foundation. Started in 2017 to spearhead relief efforts after Hurricane Maria hit the island, the foundation has become an accelerator for young entrepreneurs with startups focused on local development. This endeavor, he says, has taught him that the power of philanthropy is not so much about giving money, but dedicating time.

You took an interesting route to investment banking. Can you tell us about it?

As I was graduating from Brown, I was accepted into Stanford Law School and another school on the East Coast. During that decision-making process, a friend suggested that I check out career opportunities in investment banking since he had already recommended me. So, I decided to take an interview with Morgan Stanley, which went great. Just as I am about to make my decision on law schools, they [Morgan Stanley] made me an offer. I was now seriously considering the chance to live in New York City and work on Wall Street, but when I called the East Coast school, deferral wasn’t an option. Stanford, on the other hand, told me they would hold my spot, which was inspiring, so I went with Stanford and into investment banking.

How did your first experience go?

I worked on a deal where private equity firms were looking to buy a company. I found it fascinating to see diverse groups of investors across sectors come together to raise enough capital to buy a large corporation. Then there’s the creativity that one could put into place in owning and operating these companies. It became my passion.

When you started in private equity, conditions weren’t ideal, yet you saw some upside.

I was in investment banking from 1992 to 1994, which was not a good time for the economy or on Wall Street. I advise people starting their career to not worry about timing and instead turn negatives into positives. Look at the environment today, with tech stocks crashing. This creates a much better environment to be an incredible leader at a tech company. If you can be innovative with fewer resources, you will learn things about operations that you may never have considered. I had the opportunity to learn a lot during these early years and that is a gift. If the economy had still been roaring, things may have moved faster and I would have missed part of that journey.

What sets Thoma Bravo’s deal-making apart?

All our deals have the same mission, philosophy, strategy, and process. We have a very entrepreneurial Stanford GSB style in our business. Our mission is to turn great innovators into great companies. In our philosophy, the more profitable these mature companies are, the faster they will grow. We believe that you should never dip operating margins, and — if you do — you have to measure it separately. In our strategy, we seek recurring revenues that grow alongside ongoing innovation. We help these companies make big changes and improve operations, striving to work with existing management in an open-minded and collaborative way. That has been quite unique in private equity, and leads to a successful journey. We meet with our companies monthly, which is a lot, but it allows us to keep up with the measurement and operating progress step by step.

What was it about the Stanford GSB culture that made you want to emulate it in your company?

One of the cultural traits from Stanford GSB that we share is that you can be the highest performing individual, but you can stay humble, have fun, and be a real person. When we have successful deals, nobody levitates, thinking that they’re better than anyone. That keeps you grounded and allows you to do good work. Stanford GSB also teaches you to move very quickly and to focus on what matters. At Thoma Bravo, we try to avoid spending too much time on things that are not important to our business. And in private equity, that means three things: you need to raise capital, convince the best companies to transact with you, and improve those companies’ performances. Finally, in our business we think deeply about having a big mission, which is that software is the future of every industry. If we can help those companies become long-term innovators without requiring others to fund them, then they’re in control of their own destiny, which we feel is of great value.

How did you get involved in philanthropy?

About 13 years ago, my wife, Katy, and I were looking to do a project together with an organization that didn’t have access to external funding. While visiting Kenya, Katy had found an orphanage in a village called Mathare, about six hours drive from Nairobi. We started spending a week there each year to help take care of the children, buying concrete and cement to build the schools, or setting up irrigation infrastructure for agriculture. It was the Nairobi experience that set the foundation for my involvement in responding to Hurricane Maria, but we still maintained our commitment to the Kenyan orphanage. We continued going there until the pandemic hit, and are looking forward to going back soon.

What has philanthropic work taught you?

That the amount of work you dedicate to philanthropy is more valuable than the money. Once, I was trying to convince an extremely successful individual to join me in a philanthropic endeavor. The person told me, “I have the money but not the time.” Yes, our foundation will do great with that capital, but I would have rather had their personal commitment. I always tell young people in similar paths to mine that the time to start in philanthropy is now by dedicating time. We are very hands-on in our philanthropic activities in Puerto Rico. It energizes me to see that this is just the beginning of great things. Another key learning is just how lucky we are to have been given opportunity. We once had a big community event in a San German neighborhood about 30 minutes from Mayaguez. A man, whose wife just had a baby, came up to me [to talk]. He was an incredibly talented salesperson, but there hadn’t been electricity for weeks, so he wasn’t able to sell anything. It reminded me how local circumstances and access to opportunity play such a pivotal role in one’s ability to succeed.

Photos by Joe Budd