In this episode, Sean Mooney, Doug McCormick, and Lloyd Metz are joined by Carl Press of Thoma Bravo and Kevin MacDonald, CEO of Bluesight, to share a behind-the-scenes look at scaling a software company from a bootstrap startup to a private equity-backed category leader. Kevin reflects on his fourteen-year journey, from self-funding and navigating tough markets to leveraging venture capital and eventually partnering with private equity to drive growth and achieve ambitious goals. Carl provides insights from Thoma Bravo’s perspective, highlighting the power of strategic M&A, operational constraints, and value creation planning.

Together, they discuss the importance of alignment between CEOs and private equity partners, integrating acquisitions, and managing growth with clarity and focus. Whether you’re a founder, an executive, or a private equity professional, this episode dives deep into the challenges and successes of scaling a business for long-term impact.

Episode Highlights

1:01: Sean introduces Carl Press (Thoma Bravo) and Kevin MacDonald (Bluesight), setting the stage for a discussion on scaling software companies.

3:13: Kevin shares Bluesight’s origin as a self-funded startup and the challenges of selling to hospitals in its early days.

9:38: The transition to venture capital funding and the mindset shift toward speculative, growth-oriented investments.

13:23: Carl explains how Thoma Bravo recognized Bluesight’s potential and invested, merging it with Metasys on day one to kickstart its M&A strategy.

23:03: How Kevin and Carl aligned on a four-year value creation plan, identifying where to focus and doubling down on proven opportunities.

30:45: The operating cadence for Bluesight and Thoma Bravo, including structured board meetings and continuous collaborative interactions.

41:40: Advice for CEOs and private equity partners on setting clear expectations, establishing cultural alignment, and navigating growth together.

For more information on Thoma Bravo, go to https://www.thomabravo.com/

For more information on Bluesight, go to https://bluesight.com/

For more information on Carl Press, go to https://www.linkedin.com/in/carlpress

For more information on Kevin MacDonald, go to https://www.linkedin.com/in/kitcheckkevinmacdonald

For more information on the podcast, visit bestbutneverfinal.buzzsprout.com and embark on your journey to private equity excellence today.
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