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 (8:12)

● Starting Dolphin Equity Partners after CIBC and early challenges (14:06)

● The rise and fall—and rebirth—of Gomez Inc. (17:18)

● Discovering secondary investing through Gomez's cap table (23:58)

● The founding and investment strategy of Second Alpha (26:29)

● Understanding the structure and dynamics of the secondary market (30:21)

● How Second Alpha sources deals and builds its data pipeline (35:49)

● The process of deal execution and managing rights of refusal (41:11)

● Case study: Prove Identity and growth through secondaries (52:29)

● Thoughts on liquidity, valuation, and 401(k) access to private markets (55:35)

● AI's impact on private companies and investment strategies (59:19)

● Book and podcast recommendations (1:01:34)

● And much more!

Mentioned in this Episode:

● Second Alpha

● Chase

● CIBC

● Gomez Inc.

● Prove Identity

● TouchCommerce

● Arthur Laffer

● Acquired (podcast)

● Warren Buffett – Berkshire Hathaway Annual Letters

● Berkshire Hathaway Annual Shareholder Letters

Thanks for Listening!

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Richard Brekka - From Venture to Secondaries: Richard Brekka on Illiquid Market Advantages

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