How Orlando Bravo Built One of the Most Successful Firms in Private Equity
(0:00) Introducing Orlando Bravo
(1:53) Orlando's history, Puerto Rico origins, how he got into private equity
(7:10) How he runs Thoma Bravo: small team, outward facing, mentorship, patience in fundraising
(9:01) Role of PE in the American economy, public perception, underwriting AI risks
(15:23) Deal pricing philosophy, acquiring Boeing's avionics business
(19:24) Thoma Bravo's operating playbook after acquiring a company
(26:16) Thoughts on taking Thoma Bravo public
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20VC: What are the World's Tech Leaders Running From? Fear? Insecurity? Poverty? What Drives the Best with Orlando Bravo, Bill Ackman, Dara Khosrowshahi, Parker Conrad, Tobi Luttke, Brian Armstrong and more..
Orlando Bravo is a Founder and Managing Partner of Thoma Bravo. He led Thoma Bravo's early entry into software buyouts and built the firm into one of the top private equity firms in the world.
Tobi Lütke is the CEO and Co-Founder of Shopify, the powerhouse company allowing anyone to start and grow their e-commerce business.
Dara Khosrowshahi is the CEO of Uber, where he has managed the company's business in more than 70 countries around the world since 2017.
Parker Conrad is the Founder & CEO @ Rippling, the company that lets you easily manage your employees' payroll, benefits, expenses, devices, apps & more—in one place.
Jamie Siminoff is the Founder and Chief Inventor @ Ring, with Ring Jamie, created the world's first Wi-Fi video doorbell while working in his garage in 2011. The company sold to Amazon for $1BN.
Martín Escobari is Co-President, Managing Director and Head of General Atlantic's business in Latin America. Martín is Chairman of the firm's Investment Committee and also serves on the Management and Portfolio Committees.
Ariel Cohen is the Co-Founder and CEO @ Navan (formerly TripActions), the #1 travel management super-app used by over 8,000 companies.
Tarek Mansour is the Founder and CEO @ Kalshi, the first regulated exchange where you can trade directly on the outcome of events.
Brian Armstrong is the Co-Founder and CEO @ Coinbase, the easiest place to buy and sell cryptocurrency. Over the last 10 years, Brian has led Coinbase to today, a public company with over 3,500 employees and revenues of over $7.5BN in 2021.
Question of the Day:
What are the world's tech leaders running from?
20VC: Thoma Bravo's Orlando Bravo on Why Now is The New Normal, Why Every Company in the World is Worth its Future Cashflows, The Three Core Elements Thoma Bravo Need to See in Any Potential Deal & Orlando's Relationship to Risk, Wealth and Parenting
Orlando Bravo is a Founder and Managing Partner of Thoma Bravo. He led Thoma Bravo's early entry into software buyouts and built the firm into one of the top private equity firms in the world. Today, Orlando directs the firm's strategy and investment decisions. Orlando has overseen over 420 software acquisitions conducted by the firm, representing more than $235 billion in transaction value. Forbes named him "Wall Street's best dealmaker" in 2019, and he was dubbed "Private equity's king of SaaS" by the Financial Times in 2021.
In Today's Episode with Orlando Bravo We Discuss:
1.) From Puerto Rico Roots to Wall Street's Best Dealmaker:
How did Orlando come to co-found Thoma Bravo? What was that a-ha moment for him?
Orlando mentioned 2 mentors that shaped how he thinks, who were they? What are his single biggest lessons from those mentors?
What does Orlando know now that he wishes he had known when he started his career?
Why does Orlando disagree with setting timelines in life? Why does it not help?
2.) The Secret to Success in Value Investing:
What is good value investing today? What is it not?
What three things does Orlando look for when doing a deal and acquiring a company?
Why is every company in the world worth its future cash flows?
How important is price today? How does Orlando reflect on his own price sensitivity?
Many suggest Coupa and Anaplan were extremely expensive. How does Orlando respond and defend the prices he paid for companies in 2020-2022?
3.) WTF is Happening In Markets Today:
How does Orlando reflect on where the market is today?
Is this the new normal? How does Orlando expect the market to change over the next 12 months?
Why does Orlando believe that the best companies win in the worst times?
Is this the result of quantitative easing on behalf of central banks? Who is to blame?
How does Orlando balance the mindset of his team between risk on and taking advantage of lower prices in market but also not catching a falling knife?
4.) Orlando Bravo: The Leader, Father and Husband:
What is Orlando's biggest fear in investing? How has this changed over time?
How does Orlando reflect on his own relationship to money today? How has that changed?
What are Orlando's biggest parenting lessons from his mother?
Why does Orlando believe that for most people, their late twenties are their toughest?
How does Orlando instill the same drive and ambition in his children that he had, despite very different financial profiles growing up?
How does Orlando maintain being at the top of his game in his profession but also being a great husband? What is the secret to a happy marriage?
Items Mentioned in Today's Episode:
Orlando's Fave Book: The Power of Now: A Guide to Spiritual Enlightenment
Orlando Bravo explains $100bn private equity giant Thoma Bravo's move into crypto
After decades of experience working with software companies, Thoma Bravo, a private equity firm with over $100 billion in assets under management, announced its plans to move into crypto last fall.
In this episode of The Scoop, Thoma Bravo founder of Orlando Bravo unpacked the similarities between early software companies and today's crypto landscape, and discussed the thought process behind Thoma Bravo's decision to begin investing in the crypto ecosystem.
As Bravo shared during the interview:
“At Thoma Bravo, the way to think about how we make strategic decisions is actually quite simple: we’re very ‘micro.’ We focus on what are the best deals that are right in front of us that fit our strategy. Our strategy, if you had to define it very briefly, would be: how do you turn great innovators into great companies, and how do you do that while working and empowering existing management teams?”
While Bravo cited many similarities between the software industry from the early 2000s and the crypto industry today, he also thinks crypto companies have an edge.
Crypto companies have “better business models,” Bravo notes. "You can build a huge business here with very little capital.”
Indeed, Thoma Bravo isn’t the only private equity firm from traditional finance to recognize the fact that crypto founders have unique needs. Sequoia Capital and Bain Capital have recently launched their own crypto-specific funds catered toward crypto-native founders.
Episode 28 of Season 4 of The Scoop was recorded remotely with The Block’s Frank Chaparro and Greg Lim, Company Intelligence Research Director, and Orlando Bravo, founder and managing partner at Thoma Bravo.
Listen below, and subscribe to The Scoop on Apple, Spotify, Google Podcasts, Stitcher or wherever you listen to podcasts. Email feedback and revision requests to podcast@theblockcrypto.com.
This episode is brought to you by our sponsors Fireblocks, Coinbase Prime & Cross River
Fireblocks is an enterprise-grade platform delivering a secure infrastructure for moving, storing, and issuing digital assets. Fireblocks enables exchanges, lending desks, custodians, banks, trading desks, and hedge funds to securely scale digital asset operations through the Fireblocks Network and MPC-based Wallet Infrastructure. Fireblocks serves over 725 financial institutions, has secured the transfer of over $1.5 trillion in digital assets, and has a unique insurance policy that covers assets in storage & transit. For more information, please visit www.fireblocks.com.
About Coinbase Prime
Coinbase Prime is an integrated solution that provides institutional investors with an advanced trading platform, secure custody, and prime services to manage all their crypto assets in one place. Coinbase Prime fully integrates crypto trading and custody on a single platform, and gives clients the best all-in pricing in their network using their proprietary Smart Order Router and algorithmic execution. For more information, visit www.coinbase.com/prime.
About Cross River
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Orlando Bravo - The Art of Software Buyouts - [Invest Like the Best, EP. 257]
My guest today is Orlando Bravo, co-founder and Managing Partner of leading private equity firm, Thoma Bravo. Thoma Bravo manages over $90bn of assets and is best known for investing in software and technology businesses. It was Orlando who led the firm’s early entry into software buyouts some twenty years ago, and he has overseen more than 350 software acquisitions since. There are few, if any, people better placed to discuss private equity and software investing. Please enjoy this excellent discussion with Orlando Bravo.
For the full show notes, transcript, and links to the best content to learn more, check out the episode page here.
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Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes.
Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.
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Show Notes
[00:02:36] - [First question] - His belief about an opportunity/capital mismatch in private equity
[00:04:26] - Adjusting his own approach to take advantage of seemingly niche opportunities
[00:06:13] - Differences between software businesses they invest in versus traditional ones
[00:08:25] - Outline of how he runs their four-hour portfolio meetings
[00:09:53] - Overview of the very first deal he ever made in the software sector
[00:14:01] - The dissonance between the average SaaS company and the ones they try to manage
[00:18:22] - Major contributors that allow for their higher margins
[00:20:16] - Common mistakes of companies that mis-invest capital for growth only
[00:22:28] - Defining what market leader means writ large
[00:23:45] - Why the subsector of cyber security is such a good opportunity set
[00:26:25] - The evolving nature of the private equity world in general
[00:28:41] - Where returns will come from going forward
[00:31:47] - How good the opportunity for returns in this style of investing today is
[00:35:32] - Lessons learned on knowing when to exit or sell a position
[00:37:59] - How short their holding periods can be and how much influence they can have in such a short time
[00:40:04] - Surprising things about deal-making that he’s learned over his career
[00:41:20] - Difficulties and points of frictions in deals that still exist for him today
[00:43:11] - What part of the deal-making process he loves the most
[00:44:30] - If your job title has a C in it you’re not allowed to complain about it
[00:46:27] - Deeply held beliefs about operating excellence
[00:47:33] - What the word service means to him given everything we’ve talked about
[00:50:27] - How we do a better job of inviting talent into this space
[00:52:51] - How decentralization will define the 2020s and beyond
[00:55:48] - What is most interesting about Web3 that might affect cyber security
[00:57:42] - Where there is a lack in innovation in private equity today
[01:00:45] - Advice for young talent for building their careers
[01:03:16] - The kindest thing that anyone has ever done for him