Good Bad Billionaire: Orlando Bravo - Tech Dealmaker

Podcast: Good Bad Billionaire
Host: Simon Jack & Zing Tsjeng
Episode: Orlando Bravo: Tech Dealmaker
Release Date: April 21, 2025

Introduction

In this episode of Good Bad Billionaire, Simon Jack and Zing Tsjeng delve into the life and career of Orlando Bravo, the first Puerto Rican-born billionaire. They explore how Bravo amassed his fortune through private equity, particularly focusing on technology acquisitions, and assess his impact on the industry and philanthropy.

Early Life and Background ([03:22] - [04:25])

Orlando Bravo was born in Mayaguez, Puerto Rico, in 1970, into a family that had already achieved considerable wealth through the tuna canning industry. His grandfather founded Bravo Shipping, a significant player in the local industry, and his father continued the legacy. Growing up in a gated community, Bravo had access to private education and enjoyed extracurricular activities like sailing on the family motorboat.

A pivotal moment in Bravo's early life was his introduction to tennis at the age of eight, sparked by watching a match featuring American professional Vitus Garrilitis. This passion led him to train at the elite Nick Bollettieri Tennis Academy in Florida, where he competed alongside future stars like Jim Courier and Andre Agassi. Despite his dedication and reaching the top 40 in U.S. junior rankings, Bravo realized that a career in professional tennis was not feasible.

Education and Early Career ([05:19] - [09:13])

Bravo's athletic endeavors earned him a spot at Brown University as a sports scholar, where he excelled academically, graduating in the top 2% of his class and becoming a member of the prestigious Phi Beta Kappa fraternity. Initially planning to pursue a law doctorate at Stanford, Bravo deferred his studies to work on Wall Street at Morgan Stanley in their mergers and acquisitions department. Here, his bilingual skills in Spanish provided an edge, allowing him to work with affluent clients and participate in significant deals, including assisting a Venezuelan billionaire in acquiring a Puerto Rican supermarket chain.

However, the demanding culture of investment banking and a slowing U.S. economy led Bravo to reconsider his career path. He returned to Stanford and ambitiously pursued both a law degree and an MBA simultaneously, a demanding endeavor that underscores his strong work ethic and determination.

Rise in Private Equity ([09:13] - [15:07])

Upon completing his dual degrees in 1997, Bravo transitioned into private equity—a sector he had only briefly encountered. Private equity involves investing pooled funds from wealthy investors to acquire and manage companies, with the aim of increasing their value before selling them for a profit. Bravo's entry into this field was marked by his recruitment by Kao Thoma, a seasoned private equity veteran known as the "OG of private equity."

At Cressy Thoma in San Francisco, Bravo navigated the volatile tech landscape of the late '90s. He made substantial investments in software and technology startups, but faced significant setbacks during the dot-com bubble burst, losing a majority of his $100 million investment. Despite the financial loss, Thoma respected Bravo's resilience, allowing him another chance.

Learning from his failures, Bravo shifted his focus from risky startups to more established enterprise software companies—business-critical software solutions that, while seen as "old news," offered stability and essential services to large corporations. This strategic pivot capitalized on the enduring need for reliable enterprise software, making these companies less susceptible to market fluctuations.

Thoma Bravo and Investment Strategy ([15:07] - [27:42])

Under Thoma Bravo, Orlando implemented a "buy and build" strategy—acquiring a primary company and then strategically purchasing complementary businesses to enhance and expand the original entity. This approach proved successful with the acquisition and subsequent sale of Profit 21, a company supplying software to medical and manufacturing sectors. By enhancing operational efficiencies and making strategic acquisitions, Bravo increased the company's value by five times within three years.

In 2005, Bravo was named Managing Partner of Thoma Cressy, later rebranded to Thoma Bravo, focusing exclusively on software investments. The firm's expertise in finding niche, established tech companies positioned them uniquely in the market. Even during economic downturns, such as the 2008 financial crash, Thoma Bravo thrived by adopting a contrarian investment approach, capitalizing on opportunities when others retreated.

By 2019, Thoma Bravo had closed a $10 billion buyout fund, underscoring their significant influence and trust within the investment community. The year also marked the successful IPO of Dynatrace, a key investment that propelled Bravo to billionaire status with a net worth of approximately $3 billion, as reported by Forbes.

Philanthropy and Hurricane Maria ([31:05] - [33:48])

Orlando Bravo's philanthropic endeavors were significantly highlighted by his response to Hurricane Maria in 2017. As Puerto Rico faced widespread devastation, Bravo mobilized resources to provide critical supplies, including water, food, and satellite phones. He established the Bravo Family Foundation, which focuses on rebuilding efforts and supports education, healthcare, and entrepreneurship for young adults in Puerto Rico. By 2019, Bravo had donated over $100 million to his foundation, demonstrating a strong commitment to his homeland's recovery and development.

Additionally, Bravo made notable donations to institutions like Brown University, Stanford Healthcare, UCSF Health, and Mount Sinai Hospital, further solidifying his philanthropic legacy.

Controversies and Scandals ([34:10] - [40:23])

Despite his successes, Bravo's career has not been without controversy. Notably, SolarWinds, a company taken private by Thoma Bravo in 2016, suffered a significant cyberattack in 2020. Hackers inserted a backdoor into SolarWinds' software, affecting approximately 18,000 customers, including U.S. government agencies. The Cybersecurity and Infrastructure Security Agency (CISA) responded with an emergency directive to disconnect SolarWinds products.

Subsequently, it was revealed that Thoma Bravo and a partner had sold $286 million of SolarWinds stock days before the cyberattack became public, reducing their financial exposure. This action led to criticism and a class-action lawsuit alleging deceptive practices. Additionally, Bravo's investment in FTX, a cryptocurrency exchange founded by Sam Bankman-Fried, resulted in a total loss of $125 million when FTX declared bankruptcy in 2022. Bravo publicly stated that Thoma Bravo would no longer invest in crypto, reinforcing his commitment to avoiding past mistakes.

These incidents raised questions about Bravo's investment strategies and the broader practices within private equity, though no direct legal wrongdoing was attributed solely to him.

Philanthropy and Giving Back ([42:12] - [45:48])

Bravo's philanthropic efforts, particularly in the wake of Hurricane Maria, reflect a significant commitment to social responsibility. His Bravo Family Foundation not only provided immediate disaster relief but also invested in long-term initiatives to foster entrepreneurship and education in Puerto Rico. Additionally, his donations to medical institutions and his alma mater underscore a dedication to advancing healthcare and education.

Notable Quote:

"It's like cold calling for deals. But this time, it wasn't for investments. It was to raise money and for more supplies."
– Orlando Bravo ([32:19])

Power and Legacy ([45:50] - [47:18])

While Bravo commands substantial influence within the private equity sector, especially in software investments, his involvement in political contributions remains minimal. In 2023, he donated $500,000 to a Republican mayoral campaign in Miami but has largely maintained a stealthy presence in politics, avoiding significant endorsements or active political engagement.

Despite the scandals, Bravo's legacy is marked by his strategic acumen in private equity and his philanthropic initiatives, particularly those benefiting Puerto Rico.

Final Assessment: Good, Bad, or Just Another Billionaire? ([40:34] - [48:13])

Wealth (6/10):
Orlando Bravo's net worth of approximately $10 billion places him within the top 300 richest individuals globally. While his wealth is substantial, it is somewhat tempered by his inherited family fortune from the tuna shipping business.

Villainy (3/10):
Bravo's controversies, including the SolarWinds cyberattack and the FTX investment loss, draw partial scrutiny. However, these issues are often attributed to broader industry practices rather than personal malfeasance.

Philanthropy (7/10):
His proactive and substantial philanthropic efforts, especially in response to Hurricane Maria, significantly enhance his reputation as a benefactor.

Power and Legacy (4/10):
While influential within private equity, Bravo's understated role in politics and absence of a dominant legacy outside his investments limit his overall legacy impact.

Overall Verdict: Just Another Billionaire
Orlando Bravo exemplifies the archetype of a modern billionaire: highly successful with significant influence in his industry, embroiled in typical sector controversies, and making meaningful philanthropic contributions. His unique background as the first Puerto Rican-born billionaire adds a distinctive facet to his persona, but he fundamentally aligns with the broader billionaire narrative.

Notable Quotes:

• Orlando Bravo on Private Equity:
  "We at Thoma Bravo saw the massive disruption that cloud infrastructure was going to have on software as a service and the tech sector as a whole."
  ([28:31])

• Orlando Bravo on Failing Forward:
  "Once you make a mistake and once you get burned on something, our philosophy, and my philosophy is you never touch it again."
  ([39:55])

Conclusion

Orlando Bravo's journey from a young tennis enthusiast in Puerto Rico to a powerhouse in private equity underscores the complexities and challenges of scaling vast fortunes in the tech industry. While his strategies and business maneuvers have garnered both acclaim and criticism, his philanthropic endeavors provide a balanced perspective on his role as a billionaire in today's world.

Produced by Mark Ward with additional production by Tamsin Curry. Paul Smith is the editor, and it's a BBC Studios audio production for the BBC World Service.