My guest today is Graham Duncan. This conversation will make you think about your life in new ways. This is a two-hour segment of a 4.5-hour interview I did with Graham last year. It stands alone as remarkable, but those who subscribe to Colossus Review will gain access to the full conversation. This will be true in future issues, too.
In 2006, in his early 30s, Graham convinced Stuart Miller, CEO of home construction company Lennar, to let him manage $50 million of his family's wealth. A year later, Miller gave him the rest of his capital outside of Lennar. That investment turned into East Rock, where Graham built an incredible investing track record managing billions for a select group of families by focusing on people.
Our conversation explores a wide range of topics—from what makes a great investment partnership to the power of positive feedback loops to starting a restaurant.
I’m thankful to Graham for showing me the way so many times and for being willing to be so incredibly open in this conversation. Please enjoy this discussion with Graham Duncan.
Subscribe to Colossus Review.
For the full show notes, transcript, and links to mentioned content, check out the episode page here.
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Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com).
Show Notes:
(00:00:00) Learn about Ramp, Ridgeline, & Alphasense
(00:05:12) Intro to Graham
(00:05:54) Launching Colossus Review
(00:08:05) The Principal-Agent Dynamic
(00:10:47) Navigating Financial Crises
(00:13:22) The Right Grip in Investing
(00:17:32) Seeding and Investment Strategies
(00:21:37) Defining 'Commercial' and Its Implications
(00:26:31) The Role of Laziness and Prolific Output
(00:28:20) Finding the Right People and Positive Feedback Loops
(00:37:21) Navigating Career Transitions and Motivations
(00:43:05) Understanding Source Dynamics
(00:50:07) Key Criteria for a Great CIO
(00:59:43) Structuring Relationships with CIOs
(01:03:40) Managing Ambiguity and Protecting Mental Clarity
(01:15:09) The Importance of Source in Business
(01:17:49) Designing Physical Spaces for Success
(01:22:46) Launching a Restaurant: A Casting Exercise
(01:30:17) Taking Over and Transforming Existing Ventures
(01:33:08) Macro Investing and Adaptability
(01:36:06) Hierarchy of Investment Mastery
(01:44:10) The Art of Referencing
(01:52:08) Formative Experiences and Personal Growth
(02:00:12) Building a Business and Taking Risks
(02:07:46) The Origin of East Rock
Invest Like the Best with Patrick O'Shaughnessy 
