Thoma Bravo's Behind the Deal

In this special re-release of Behind the Deal—now brought to life in video—Orlando Bravo sits down with Thoma Bravo co-founder Carl Thoma for a conversation on the origins of modern private equity. Widely regarded as one of the pioneers of the industry, Carl shares how he developed the “buy and build” strategy, why discipline around risk and valuation matters more than ever and how mentorship shaped the trajectory of Thoma Bravo’s software investing strategy. This episode traces the early missteps, hard-earned lessons, and defining principles — around partnership, performance and integrity — that helped build one of the most enduring firms in private equity. Whether you're an investor, operator, or early in your career, this conversation is a reminder that great outcomes are built on fundamentals, trust and learning from mistakes. For more information on Thoma Bravo's Behind the Deal, visit https://www.thomabravo.com/behindthedeal Learn more about Thoma Bravo: https://www.thomabravo.com/ Disclaimer: This podcast is for informational purposes only and does not constitute an advertisement. Views expressed are those of the individuals and not necessarily the views of Thoma Bravo or its affiliates. Thoma Bravo funds generally hold interest in the companies discussed. This podcast should not be construed as an offer to solicit the purchase of any interest in any Thoma Bravo fund. Certain statements about Thoma Bravo made by portfolio company executives are intended to illustrate Thoma Bravo's business relationship with such persons rather than Thoma Bravo's capabilities or expertise with respect to investment advisory services. Portfolio company executives were not compensated in connection with their podcast participation, although they generally received compensation and investment opportunities in connection with their portfolio company roles and in certain cases are also owners of portfolio company securities and or investors in Thoma Bravo funds. Such compensation and investments subject podcast participants to potential conflicts of interest. In addition, this podcast includes forward-looking statements. These statements are based on current expectations and assumptions and involve significant risks and uncertainties that could cause actual results to differ materially.

In this episode of Beyond the Deal, Thoma Bravo Partner Carl Press is joined by Adam Kinalski and Sam Yules to tell the inside story of building the Explore platform from the ground up. What started as a blank slate in 2019 has grown into a high-velocity investment platform focused on emerging enterprise software leaders. The team shares how Explore was created to stay true to Thoma Bravo’s middle-market roots, the early challenges of building a pipeline from scratch, and the lessons learned from sourcing, mentorship and long-term relationship building. From cold starts and conference room pitches to navigating deals with imperfect data, this conversation offers a candid look at what it takes to build a platform—and a team—inside the world’s largest software-focused investment firm. For more information on Thoma Bravo's Behind the Deal, visit https://www.thomabravo.com/behindthedeal Learn more about Thoma Bravo: https://www.thomabravo.com/ Disclaimer: This podcast is for informational purposes only and does not constitute an advertisement. Views expressed are those of the individuals and not necessarily the views of Thoma Bravo or its affiliates. Thoma Bravo funds generally hold interest in the companies discussed. This podcast should not be construed as an offer to solicit the purchase of any interest in any Thoma Bravo fund. Certain statements about Thoma Bravo made by portfolio company executives are intended to illustrate Thoma Bravo's business relationship with such persons rather than Thoma Bravo's capabilities or expertise with respect to investment advisory services. Portfolio company executives were not compensated in connection with their podcast participation, although they generally received compensation and investment opportunities in connection with their portfolio company roles and in certain cases are also owners of portfolio company securities and or investors in Thoma Bravo funds. Such compensation and investments subject podcast participants to potential conflicts of interest. In addition, this podcast includes forward-looking statements. These statements are based on current expectations and assumptions and involve significant risks and uncertainties that could cause actual results to differ materially.

In this episode of Behind the Deal, Thoma Bravo Partner Carl Press and Principal Adam Kinalski are joined by Exostar CEO Richard Addi to tell the story behind one of the firm’s most hard-fought investments. Exostar, a mission-critical platform serving the aerospace and defense industry, wasn’t for sale. What followed was a multi-year effort to build trust with six joint venture shareholders, navigate complex stakeholder dynamics and ultimately get the deal across the finish line. Together, Carl, Adam and Richard unpack the full lifecycle of the investment—from sourcing and diligence to transformation and exit—and reflect on what it took to transition Exostar from a shared-service joint venture into a high-growth, profitable enterprise software company. In just three years, the business accelerated growth, expanded margins and positioned itself for a successful exit, making Exostar a defining deal for Thoma Bravo’s Explore platform. For more information on Thoma Bravo's Behind the Deal, visit https://www.thomabravo.com/behindthedeal Learn more about Thoma Bravo: https://www.thomabravo.com/ Learn more about Exostar: https://www.exostar.com/ Disclaimer: This podcast is for informational purposes only and does not constitute an advertisement. Views expressed are those of the individuals and not necessarily the views of Thoma Bravo or its affiliates. Thoma Bravo funds generally hold interest in the companies discussed. This podcast should not be construed as an offer to solicit the purchase of any interest in any Thoma Bravo fund. Certain statements about Thoma Bravo made by portfolio company executives are intended to illustrate Thoma Bravo's business relationship with such persons rather than Thoma Bravo's capabilities or expertise with respect to investment advisory services. Portfolio company executives were not compensated in connection with their podcast participation, although they generally received compensation and investment opportunities in connection with their portfolio company roles and in certain cases are also owners of portfolio company securities and or investors in Thoma Bravo funds. Such compensation and investments subject podcast participants to potential conflicts of interest. In addition, this podcast includes forward-looking statements. These statements are based on current expectations and assumptions and involve significant risks and uncertainties that could cause actual results to differ materially.

At Thoma Bravo’s 2025 AI Summit, Partner Hudson Smith sits down with Olo Founder and CEO Noah Glass to unpack one of the firm’s most compelling recent investments. From its early days as a text-based ordering tool to becoming a category leader powering digital experiences for over 750 restaurant brands, Olo has spent two decades shaping how consumers interact with restaurants. In this conversation, Noah shares the origin story behind the company, the strategic thinking behind taking Olo private in 2025, and how data, network effects and AI are redefining hospitality at scale. They also explore what makes restaurant technology uniquely complex, why structured data helps create a durable moat, and how AI is expected tol transform both the guest experience and restaurant operations in the years ahead. For more information on Thoma Bravo's Behind the Deal, visit https://www.thomabravo.com/behindthedeal Learn more about Thoma Bravo: https://www.thomabravo.com/ Learn more about Olo: https://www.olo.com/ Disclaimer: This podcast may contain forward looking statements reflecting current views regarding market conditions, technological evolution, and anticipated developments, which are based on current expectations and assumptions, involve risks and uncertainties that could cause actual results to differ materially, and speak only as of the date of recording with no obligation to update. This podcast is for informational purposes only and does not constitute an advertisement. Views expressed are those of the individuals and not necessarily the views of Thoma Bravo or its affiliates. Thoma Bravo funds generally hold interest in the companies discussed. This podcast should not be construed as an offer to solicit the purchase of any interest in any Thoma Bravo fund. Certain statements about Thoma Bravo made by portfolio company executives are intended to illustrate Thoma Bravo's business relationship with such persons rather than Thoma Bravo's capabilities or expertise with respect to investment advisory services. Portfolio company executives were not compensated in connection with their podcast participation, although they generally received compensation and investment opportunities in connection with their portfolio company roles and in certain cases are also owners of portfolio company securities and or investors in Thoma Bravo funds. Such compensation and investments subject podcast participants to potential conflicts of interest. In addition, this podcast includes forward-looking statements. These statements are based on current expectations and assumptions and involve significant risks and uncertainties that could cause actual results to differ materially.

In this episode of Beyond the Deal, Thoma Bravo Senior Partner A.J. Rohde and Principal Peter Hernandez sit down with Nearmap CEO Andy Watt for a candid conversation about leadership, culture and building a global technology company from Australia. Andy shares the story of how a move from Scotland to Sydney turned into a decades-long journey with a leading Australian technology company. The group reflects on Nearmap’s growth, the experience of scaling a global company from Australia and the behind-the-scenes moments that helped Thoma Bravo win the trust of the Nearmap team. The episode closes with A.J.’s lightning round — covering everything from Scottish traditions and Australian sports to rock bands and Vegemite. It’s a lighter look at the relationships, personalities and moments that happen beyond the deal. For more information on Thoma Bravo's Behind the Deal, visit https://www.thomabravo.com/behindthedeal Learn more about Thoma Bravo: https://www.thomabravo.com/ Learn more about Nearmap: https://www.nearmap.com/ Disclaimer: This podcast is for informational purposes only and does not constitute an advertisement. Views expressed are those of the individuals and not necessarily the views of Thoma Bravo or its affiliates. Thoma Bravo funds generally hold interest in the companies discussed. This podcast should not be construed as an offer to solicit the purchase of any interest in any Thoma Bravo fund. Certain statements about Thoma Bravo made by portfolio company executives are intended to illustrate Thoma Bravo's business relationship with such persons rather than Thoma Bravo's capabilities or expertise with respect to investment advisory services. Portfolio company executives were not compensated in connection with their podcast participation, although they generally received compensation and investment opportunities in connection with their portfolio company roles and in certain cases are also owners of portfolio company securities and or investors in Thoma Bravo funds. Such compensation and investments subject podcast participants to potential conflicts of interest. In addition, this podcast includes forward-looking statements. These statements are based on current expectations and assumptions and involve significant risks and uncertainties that could cause actual results to differ materially.

In this episode of Thoma Bravo’s Behind the Deal, Senior Partner A.J. Rohde and Principal Peter Hernandez sit down with Nearmap CEO Andy Watt to unpack Thoma Bravo’s investment in Nearmap and the company’s evolution from an aerial imagery provider into a global property intelligence platform. They discuss how the deal originated, what made Nearmap stand out, the complexities of taking an Australian public company private and how the business has expanded through AI, software and strategic acquisitions. Andy also shares his journey from Scotland to Australia, how Nearmap scaled from roughly $40 million in revenue to more than $300 million and why the company sees a long runway ahead across insurance, construction, government and beyond. For more information on Thoma Bravo's Behind the Deal, visit https://www.thomabravo.com/behindthedeal Learn more about Thoma Bravo: https://www.thomabravo.com/ Learn more about Nearmap: https://www.nearmap.com/ Disclaimer: This podcast is for informational purposes only and does not constitute an advertisement. Views expressed are those of the individuals and not necessarily the views of Thoma Bravo or its affiliates. Thoma Bravo funds generally hold interest in the companies discussed. This podcast should not be construed as an offer to solicit the purchase of any interest in any Thoma Bravo fund. Certain statements about Thoma Bravo made by portfolio company executives are intended to illustrate Thoma Bravo's business relationship with such persons rather than Thoma Bravo's capabilities or expertise with respect to investment advisory services. Portfolio company executives were not compensated in connection with their podcast participation, although they generally received compensation and investment opportunities in connection with their portfolio company roles and in certain cases are also owners of portfolio company securities and or investors in Thoma Bravo funds. Such compensation and investments subject podcast participants to potential conflicts of interest. In addition, this podcast includes forward-looking statements. These statements are based on current expectations and assumptions and involve significant risks and uncertainties that could cause actual results to differ materially.

This week on Thoma Bravo's Beyond the Deal, the spotlight turns inward. Managing Partner Holden Spaht and Partner Brian Jaffee share their origin stories at Thoma Bravo — what the firm looked like in its early days, how responsibility comes fast, and why mentorship and entrepreneurialism sit at the center of the culture. From cold outreach and the firm’s early focus on software to leading exits and mentoring the next generation, this episode offers an inside look at how performance is built — and sustained — over decades. For more information on Thoma Bravo's Behind the Deal, visit https://www.thomabravo.com/behindthedeal Learn more about Thoma Bravo: https://www.thomabravo.com/ Disclaimer: This podcast is for informational purposes only and does not constitute an advertisement. Views expressed are those of the individuals and not necessarily the views of Thoma Bravo or its affiliates. Thoma Bravo funds generally hold interest in the companies discussed. This podcast should not be construed as an offer to solicit the purchase of any interest in any Thoma Bravo fund. Certain statements about Thoma Bravo made by portfolio company executives are intended to illustrate Thoma Bravo's business relationship with such persons rather than Thoma Bravo's capabilities or expertise with respect to investment advisory services. Portfolio company executives were not compensated in connection with their podcast participation, although they generally received compensation and investment opportunities in connection with their portfolio company roles and in certain cases are also owners of portfolio company securities and or investors in Thoma Bravo funds. Such compensation and investments subject podcast participants to potential conflicts of interest. In addition, this podcast includes forward-looking statements. These statements are based on current expectations and assumptions and involve significant risks and uncertainties that could cause actual results to differ materially.

In this episode of Thoma Bravo’s Behind the Deal, Managing Partner Holden Spaht and Partner Brian Jaffee revisit the take-private and sale of Ellie Mae — a leading U.S. mortgage loan origination system — and how a $3.7B investment became an $11B exit to Intercontinental Exchange (ICE) just over a year later. They break down the original investment thesis, the operational playbook, pricing and packaging strategy, and the M&A decisions that drove one of the firm’s landmark exits — including the rare “reverse re-trade” that moved the final agreement from $10B to $11B. For more information on Thoma Bravo's Behind the Deal, visit https://www.thomabravo.com/behindthedeal Learn more about Thoma Bravo: https://www.thomabravo.com/ Learn more about Ellie Mae now operating as ICE Mortgage Technology here: https://mortgagetech.ice.com/ Disclaimer: This podcast is for informational purposes only and does not constitute an advertisement. Views expressed are those of the individuals and not necessarily the views of Thoma Bravo or its affiliates. Thoma Bravo funds generally hold interest in the companies discussed. This podcast should not be construed as an offer to solicit the purchase of any interest in any Thoma Bravo fund. Certain statements about Thoma Bravo made by portfolio company executives are intended to illustrate Thoma Bravo's business relationship with such persons rather than Thoma Bravo's capabilities or expertise with respect to investment advisory services. Portfolio company executives were not compensated in connection with their podcast participation, although they generally received compensation and investment opportunities in connection with their portfolio company roles and in certain cases are also owners of portfolio company securities and or investors in Thoma Bravo funds. Such compensation and investments subject podcast participants to potential conflicts of interest. In addition, this podcast includes forward-looking statements. These statements are based on current expectations and assumptions and involve significant risks and uncertainties that could cause actual results to differ materially.

In this episode of Beyond the Deal, Intel 471 CEO and Co-Founder Jason Passwaters joins Thoma Bravo Partner Adam Solomon for a candid conversation about the experiences that shaped him as a leader. Passwaters reflects on his early years in the U.S. Marines — from infantry to counterintelligence — and the lessons he carried into building a global cybersecurity company. He shares how resourcefulness, team camaraderie, and mission-first thinking became foundational to Intel 471’s culture, as well as the personal commitment required to bootstrap a business while raising a family. The discussion also explores leadership beyond titles: earning trust through action, building aligned teams across borders, and why humility and self-awareness may be the most underrated traits of a CEO. For more information on Thoma Bravo's Behind the Deal, visit https://www.thomabravo.com/behindthedeal Learn more about Thoma Bravo: https://www.thomabravo.com/ Learn more about Intel 471: https://www.intel471.com Disclaimer: This podcast is for informational purposes only and does not constitute an advertisement. Views expressed are those of the individuals and not necessarily the views of Thoma Bravo or its affiliates. Thoma Bravo funds generally hold interest in the companies discussed. This podcast should not be construed as an offer to solicit the purchase of any interest in any Thoma Bravo fund. Certain statements about Thoma Bravo made by portfolio company executives are intended to illustrate Thoma Bravo's business relationship with such persons rather than Thoma Bravo's capabilities or expertise with respect to investment advisory services. Portfolio company executives were not compensated in connection with their podcast participation, although they generally received compensation and investment opportunities in connection with their portfolio company roles and in certain cases are also owners of portfolio company securities and or investors in Thoma Bravo funds. Such compensation and investments subject podcast participants to potential conflicts of interest. In addition, this podcast includes forward-looking statements. These statements are based on current expectations and assumptions and involve significant risks and uncertainties that could cause actual results to differ materially.

In this episode, Thoma Bravo Partner Adam Solomon and SVP Chandler Gay break down the firm’s investment in Intel 471, a bootstrapped, founder-led cyber threat intelligence company trusted by many of the world’s largest enterprises. They revisit the rigorous diligence process — including moments when the deal nearly fell apart — and explain what ultimately set the business apart: proprietary, highly actionable intelligence, exceptional retention, and disciplined, profitable growth. Adam then sits down with CEO and Co-Founder Jason Passwaters, a former Marine and FBI cybercrime investigator, to discuss building Intel 471 without outside capital, partnering with Thoma Bravo to strengthen and expand the company, executing its first acquisitions, and how AI is reshaping the cyber threat landscape. For more information on Thoma Bravo's Behind the Deal, visit https://www.thomabravo.com/behindthedeal Learn more about Thoma Bravo: https://www.thomabravo.com/ Learn more about Intel 471: https://www.intel471.com/ Disclaimer: This podcast is for informational purposes only and does not constitute an advertisement. Views expressed are those of the individuals and not necessarily the views of Thoma Bravo or its affiliates. Thoma Bravo funds generally hold interest in the companies discussed. This podcast should not be construed as an offer to solicit the purchase of any interest in any Thoma Bravo fund. Certain statements about Thoma Bravo made by portfolio company executives are intended to illustrate Thoma Bravo's business relationship with such persons rather than Thoma Bravo's capabilities or expertise with respect to investment advisory services. Portfolio company executives were not compensated in connection with their podcast participation, although they generally received compensation and investment opportunities in connection with their portfolio company roles and in certain cases are also owners of portfolio company securities and or investors in Thoma Bravo funds. Such compensation and investments subject podcast participants to potential conflicts of interest. In addition, this podcast includes forward-looking statements. These statements are based on current expectations and assumptions and involve significant risks and uncertainties that could cause actual results to differ materially.

In this episode of Thoma Bravo’s Behind the Deal, Managing Partner Holden Spaht sits down with Charles Gottdiener, CEO of Anaplan, and Leagh Turner, CEO of Coupa, to discuss how enterprise software leaders are turning AI innovation into real business impact. Drawing on their experience as both builders and users of AI, they share how AI is driving productivity, reshaping operating models, and expanding operating leverage—while highlighting the importance of governance, disciplined pricing, and domain expertise as AI adoption accelerates. For more information on Thoma Bravo's Behind the Deal, visit https://www.thomabravo.com/behindthedeal Learn more about Thoma Bravo: https://www.thomabravo.com/ Learn more about Anaplan: https://www.anaplan.com/ Learn more about Coupa: https://www.coupa.com/ Disclaimer: This podcast is for informational purposes only and does not constitute an advertisement. Views expressed are those of the individuals and not necessarily the views of Thoma Bravo or its affiliates. Thoma Bravo funds generally hold interest in the companies discussed. This podcast should not be construed as an offer to solicit the purchase of any interest in any Thoma Bravo fund. Certain statements about Thoma Bravo made by portfolio company executives are intended to illustrate Thoma Bravo's business relationship with such persons rather than Thoma Bravo's capabilities or expertise with respect to investment advisory services. Portfolio company executives were not compensated in connection with their podcast participation, although they generally received compensation and investment opportunities in connection with their portfolio company roles and in certain cases are also owners of portfolio company securities and or investors in Thoma Bravo funds. Such compensation and investments subject podcast participants to potential conflicts of interest. In addition, this podcast includes forward-looking statements. These statements are based on current expectations and assumptions and involve significant risks and uncertainties that could cause actual results to differ materially.

Recorded live at Thoma Bravo’s 2025 AI Summit, this episode features a fireside chat between Thoma Bravo Founder and Managing Partner Orlando Bravo and IBM CEO Arvind Krishna. Krishna shares an operator’s view on why AI is unequivocally good for software—boosting developer productivity, expanding entry-level hiring, and unlocking billions in back-office automation that IBM has reinvested into software R&D and growth. The conversation also explores IBM’s $34 billion acquisition of Red Hat, including the strategic investment on hybrid cloud and OpenShift, how the deal scaled beyond expectations, and why conviction was critical despite initial market skepticism. Looking ahead, Krishna outlines what’s next for enterprise AI: agents layered on systems of record, smaller purpose-built models, and why companies that scale AI deliberately will pull ahead. For more information on Thoma Bravo's Behind the Deal, visit https://www.thomabravo.com/behindthedeal Learn more about Thoma Bravo: https://www.thomabravo.com/ Learn more about IBM: https://www.ibm.com/case-studies/ibm-client-zero?lnk=hpls1us Disclaimer: This podcast is for informational purposes only and does not constitute an advertisement. Views expressed are those of the individuals and not necessarily the views of Thoma Bravo or its affiliates. Thoma Bravo funds generally hold interest in the companies discussed. This podcast should not be construed as an offer to solicit the purchase of any interest in any Thoma Bravo fund. Certain statements about Thoma Bravo made by portfolio company executives are intended to illustrate Thoma Bravo's business relationship with such persons rather than Thoma Bravo's capabilities or expertise with respect to investment advisory services. Portfolio company executives were not compensated in connection with their podcast participation, although they generally received compensation and investment opportunities in connection with their portfolio company roles and in certain cases are also owners of portfolio company securities and or investors in Thoma Bravo funds. Such compensation and investments subject podcast participants to potential conflicts of interest. In addition, this podcast includes forward-looking statements. These statements are based on current expectations and assumptions and involve significant risks and uncertainties that could cause actual results to differ materially.

What separates good CEOs from great ones? According to Proofpoint CEO Sumit Dhawan, it’s the ability to build belief. In this episode of Beyond the Deal, Thoma Bravo Managing Partner Seth Boro sits down with Sumit to discuss the leadership principles behind scaling a high-performing, human-centric cybersecurity company. From growing up in Delhi and learning the value of hard work and ownership, to leading a global public company, Sumit reflects on how transparency, storytelling, discipline, and mentorship build trust and unlock the best work from teams—and why building belief may be the most underrated skill in leadership today. For more information on Thoma Bravo's Behind the Deal, visit https://www.thomabravo.com/behindthedeal Learn more about Thoma Bravo: https://www.thomabravo.com/ Learn more about Proofpoint: https://www.proofpoint.com/us Disclaimer: This podcast is for informational purposes only and does not constitute an advertisement. Views expressed are those of the individuals and not necessarily the views of Thoma Bravo or its affiliates. Thoma Bravo funds generally hold interest in the companies discussed. This podcast should not be construed as an offer to solicit the purchase of any interest in any Thoma Bravo fund. Certain statements about Thoma Bravo made by portfolio company executives are intended to illustrate Thoma Bravo's business relationship with such persons rather than Thoma Bravo's capabilities or expertise with respect to investment advisory services. Portfolio company executives were not compensated in connection with their podcast participation, although they generally received compensation and investment opportunities in connection with their portfolio company roles and in certain cases are also owners of portfolio company securities and or investors in Thoma Bravo funds. Such compensation and investments subject podcast participants to potential conflicts of interest. In addition, this podcast includes forward-looking statements. These statements are based on current expectations and assumptions and involve significant risks and uncertainties that could cause actual results to differ materially.

Season 4 of Behind the Deal kicks off with a deep dive into Proofpoint, a key investment within Thoma Bravo’s cybersecurity portfolio. Seth Boro and Andrew Almeida reflect on the conviction behind the firm’s largest software buyout at the time, while Proofpoint CEO Sumit Dhawan shares how the company has scaled, evolved its platform, and stayed ahead of rapidly growing cyber threats in an AI-driven world. For more information on Thoma Bravo's Behind the Deal, visit https://www.thomabravo.com/behindthedeal Learn more about Thoma Bravo: https://www.thomabravo.com/ Learn more about Proofpoint: https://www.proofpoint.com/us Disclaimer: This podcast is for informational purposes only and does not constitute an advertisement. Views expressed are those of the individuals and not necessarily the views of Thoma Bravo or its affiliates. Thoma Bravo funds generally hold interest in the companies discussed. This podcast should not be construed as an offer to solicit the purchase of any interest in any Thoma Bravo fund. Certain statements about Thoma Bravo made by portfolio company executives are intended to illustrate Thoma Bravo's business relationship with such persons rather than Thoma Bravo's capabilities or expertise with respect to investment advisory services. Portfolio company executives were not compensated in connection with their podcast participation, although they generally received compensation and investment opportunities in connection with their portfolio company roles and in certain cases are also owners of portfolio company securities and or investors in Thoma Bravo funds. Such compensation and investments subject podcast participants to potential conflicts of interest. In addition, this podcast includes forward-looking statements. These statements are based on current expectations and assumptions and involve significant risks and uncertainties that could cause actual results to differ materially.

Thoma Bravo returns with Season 4 of Behind the Deal—the chart-topping, award-winning podcast that goes inside the strategy, leadership, and conviction behind the world’s largest software-focused investment firm. This season brings listeners to the forefront of the software and AI landscape. Hear from Proofpoint’s CEO on how AI is reshaping cybersecurity and what it takes to lead at scale in an increasingly complex threat environment; gain a rare perspective on the future of AI in a candid conversation between Thoma Bravo Founder and Managing Partner Orlando Bravo and IBM CEO Arvind Krishna; and learn how the CEOs of Anaplan and Coupa are navigating AI-driven transformation. Season 4 also features in-depth examinations of major acquisitions, including Intel 471 and Ellie Mae, unpacking the strategic thinking, decision-making, and execution behind each deal. Featuring some of Thoma Bravo’s most senior voices and most timely insights yet, Thoma Bravo’s Behind the Deal offers a look at how leading software companies are built. For more information on Thoma Bravo's Behind the Deal, visit https://www.thomabravo.com/behindthedeal Learn more about Thoma Bravo: https://www.thomabravo.com/

In this bonus episode, Thoma Bravo founder and managing partner, Orlando Bravo joins View From The Top from Stanford GSB for a candid conversation on his nonlinear journey—from leaving a small town in Puerto Rico to building one of the world’s leading software investment firms. Orlando opens up about early career setbacks—including rejection, failed deals, and the mentors who shaped his investing and leadership philosophy. He shares why discipline, humility, strong partnerships, and “doing your own thing” became the foundation of Thoma Bravo’s approach, as well as his long-term commitment to entrepreneurship and impact in Puerto Rico. This conversation offers rare insights on leadership, resilience, mentorship, and what it really takes to build enduring software companies. For more information on Thoma Bravo's Behind the Deal, visit https://www.thomabravo.com/behindthedeal Learn more about Thoma Bravo: https://www.thomabravo.com/ Learn more about View From the Top: https://www.gsb.stanford.edu/business-podcasts/view-top-podcast

Inspired by the book Getting Real, HubSync Founder and CEO John McGowan explains to Thoma Bravo Partner Ross Devor how operating under tight timelines and budgets with a lean team forced HubSync to focus on an engineer-first approach, providing a foundation for a company that was able to scale.

HubSync started as a bootstrapped idea from John McGowan, a former Big Four tax professional who saw the tech gap in mid-sized CPA firms. In this episode of ‘Behind the Deal,’ Thoma Bravo Partner Ross Devor talks with John about how he turned early consulting work into a profitable SaaS business, the strategy behind landing over 40% of the top 25 accounting firms, and how product market fit shaped every decision.

In the Beyond the Deal mini-sode with Thoma Bravo’s A.J. Rohde and Peter Hernandez, hear NextGen Healthcare CEO David Sides explain his approach to leadership, inspired by his family’s medical roots, and how NextGen Healthcare grew into one of the most trustworthy companies in America. For more information on Thoma Bravo's Behind the Deal, visit https://www.thomabravo.com/behindthedealLearn more about Thoma Bravo: https://www.thomabravo.com/Visit NextGen Healthcare's website: https://bit.ly/3TN6i7s

In this episode, Thoma Bravo Senior Partner A.J. Rohde sits down with Peter Hernandez, a Senior Vice President on our Discover team, to detail the strategic take-private of NextGen Healthcare, a leading provider of innovative, cloud-based healthcare technology solutions. They are joined in the studio by NextGen Healthcare CEO David Sides and discuss their bold vision for the future of healthcare IT. Hear perspectives on NextGen Healthcare’s exciting new chapter, marked by a recent investment by Madison Dearborn Partners, to further accelerate the company’s growth. For more information on Thoma Bravo's Behind the Deal, visit https://www.thomabravo.com/behindthedealLearn more about Thoma Bravo: https://www.thomabravo.com/Visit NextGen Healthcare's website: https://bit.ly/3TN6i7s