Our teacher today is Will Thorndike, co-founder of Compounding Labs and author of the acclaimed book, “The Outsiders.” In our opinion, Will has emerged as one of the most influential and innovative investor minds of the past few decades. And if you care about long-term value creation and the art of capital allocation, chances are you've also benefited from some of his ideas.

In 1994, he founded Housatonic Partners, a pioneering private equity firm known for its unusually long holding periods and its leadership in the search fund space alongside his mentor and Stanford professor Irv Grousbeck. Will helped to originate the modern search fund model, backing early career CEOs to buy and grow businesses with long-term horizons and radically aligned incentives.

Since then, he has invested in the majority of the top 20 search fund outcomes to date, including Asurion, which he recently profiled on his podcast 50X.

We explore Will's full arc from the research that led to “The Outsiders” to his decades as an investor to the new frontier he's now helping to shape. We talk about what makes a business truly enduring, why great leadership and resource allocation remain so misunderstood, and how the right people, structure, and alignment enable companies to compound over time. Please enjoy this class with Will Thorndike.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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Joys of Compounding is a property of Pine Grove Studios in collaboration with Colossus, LLC. For more episodes of Joys of Compounding, visit joincolossus.com/episodes.

Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com).

Show Notes

(00:00:00) Welcome to The Joys of Compounding

(00:00:57) Introducing Will Thorndike

(00:03:35) The Rise of Long Duration Serial Acquisition Holding Companies

(00:07:25) The 50X Podcast Journey

(00:16:29) The Origins of Will's Investing Career

(00:18:11) Stanford's Influence and Key Mentors

(00:23:48) The Search Fund Model Explained

(00:39:18) The Outsiders: From Concept to Acclaim

(00:46:33) The Influence of Leverage and Share Buybacks

(00:47:30) Personal Reflections on the Book's Impact

(00:52:54) Experiments in Public Markets: CNX and Perimeter

(00:58:35) The Evolution of Inorganic Growth Models

(01:02:52) The Power of Long-Term Ownership

(01:14:52) The Importance of Relationships and Learning

Will Thorndike - Lessons from the Eternal Outsider - [Joys of Compounding, EP.28]