Value Investing with Legends

In this episode, host Tano Santos sits down with Richard Brekka, founder and managing partner of Second Alpha, to examine the lesser-known world of secondary investing in private technology companies. With decades of experience—from venture capital to secondary transactions—Richard shares his journey through private equity at Chase and CIBC, his role in building and reviving companies like Gomez Inc., and how that led him to identify a unique investment niche. He explains the mechanics of sourcing deals in illiquid markets, using data and AI to surface hidden gems, and the psychology of getting deals done. The discussion also explores valuations, exits, and policy implications of private market access for 401(k) investors, plus the impact of AI on business fundamentals and much more! Key Topics: ● Richard's early exposure to entrepreneurship and finance (3:29) ● Lessons from Arthur Laffer and University of Chicago MBA experience (6:15) ● Early career in private equity at Chase and learning value investing