Invest Like the Best

Key Takeaways

“My appetite for finding the best person in the world to do the thing instead of me doing it is almost infinite.” – Graham Duncan
Desire wants what it wants; get in tune with your desire
Leverage your comparative advantage: Most investing strategies are downstream of the simple goal of (1) making money and (2) not losing too much
- In investing, the goal is to make money – not be right or feed the go
Navigating the Principal-Agent Dynamic: The principal should set the condition that tells the agent that it is okay to make mistakes; if the agent feels that he cannot make mistakes, then he probably won’t take sufficient risks
Peter Keonig on Source Dynamics: All organizational dysfunction can be traced back to disagreements about the Source; messing with the origin in any subtle way can affect the entire trajectory of the thing in ways that you wouldn’t think
Mastery involves “becoming source” of your own style of investing – it involves coming into your own and not playing the game as others have played it, but truly playing it in your own idiosyncratic way
Traits of the best investors: (1) Decisiveness (2) Open-mindedness with a point of view
- Be opportunistic and flexible so that you can flow with emergent market dynamics instead of getting stuck in them
Be Like Toranaga: When everybody else is losing their minds, hold – just hold
Follow Your Bliss: Trust the universe that if you get in touch with the thing that you are compulsive about and love, the world will come to you
Quiet Ego as a Superpower: The principal should focus on making money and be less concerned about making the idea their own
On wandering during a wilderness period in your life: Have patience and don’t overweight any one thing; don’t over-index on “where you are in the system” or become too concerned with being “relevant”
“My appetite for finding the best person in the world to do the thing instead of me doing it is almost infinite.” – Graham Duncan
Focus on the intersection of what the world wants from you and what you actually want

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.

-----
This episode is brought to you by Ramp. Ramp’s mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Ramp is the fastest-growing FinTech company in history, and it’s backed by more of my favorite past guests (at least 16 of them!) than probably any other company I’m aware of. Go to Ramp.com/invest to sign up for free and get a $250 welcome bonus.
–
This episode is brought to you by Ridgeline. Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. I think this platform will become the standard for investment managers, and if you run an investing firm, I highly recommend you find time to speak with them. Head to ridgelineapps.com to learn more about the platform.
–
This episode is brought to you by Alphasense. AlphaSense has completely transformed the research process with cutting-edge AI technology and a vast collection of top-tier, reliable business content. Imagine completing your research five to ten times faster with search that delivers the most relevant results, helping you make high-conviction decisions with confidence. Invest Like the Best listeners can get a free trial now at Alpha-Sense.com/Invest and experience firsthand how AlphaSense and Tegus help you make smarter decisions faster.
-----

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
(00:09:40) Intro to Graham
(00:10:24) Launching Colossus Review
(00:12:25) The Principal-Agent Dynamic
(00:15:17) Navigating Financial Crises
(00:17:52) The Right Grip in Investing
(00:22:02) Seeding and Investment Strategies
(00:26:07) Defining 'Commercial' and Its Implications
(00:31:01) The Role of Laziness and Prolific Output
(00:32:50) Finding the Right People and Positive Feedback Loops
(00:41:51) Navigating Career Transitions and Motivations
(00:47:35) Understanding Source Dynamics
(00:54:37) Key Criteria for a Great CIO
(01:04:13) Structuring Relationships with CIOs
(01:08:10) Managing Ambiguity and Protecting Mental Clarity
(01:19:39) The Importance of Source in Business
(01:22:19) Designing Physical Spaces for Success
(01:27:18) Launching a Restaurant: A Casting Exercise
(01:34:47) Taking Over and Transforming Existing Ventures
(01:37:38) Macro Investing and Adaptability
(01:40:36) Hierarchy of Investment Mastery
(01:48:40) The Art of Referencing
(01:56:38) Formative Experiences and Personal Growth
(02:04:44) Building a Business and Taking Risks
(02:12:16) The Origin of East Rock