The Investor Who Left the Rat Race to Build a $100M Fund | Ep 225 with Sam Chipkin the Founder & CIO of 5AM Capital
Description
Sam Chipkin, after nearly a decade in the high-stress world of New York finance, moved to Bondi Beach and rewired his approach to investing. In this episode, he shares how quiet mornings, long walks, and deep research shaped his investment strategy—and why 5AM Capital is betting on patient capital, enduring businesses, and disciplined risk.
Key Discussion Points:
Leaving Wall Street: Why chaos isn’t required to create value
Building a boutique fund that caps growth at $750M
The power of investing in monopolistic businesses with durable moats
Why the best investors act like long-term owners, not traders
Founder vs. hired CEO mindset—and how it affects outcomes
How stress and stillness each played a role in shaping his success
What most people get wrong about investing returns
The underestimated mental load of wearing every hat as a founder
Takeaways:
Slower, focused growth often outlasts fast, flashy scale
The best investments are deeply researched, not broadly scattered
Building something meaningful requires clarity, conviction, and capacity to think long-term
Culture and alignment are assets—don’t outgrow them
Closing Thoughts:
Sam Chipkin proves that high returns don’t require chaos. With a boutique, conviction-driven strategy and a firm belief in doing fewer things better, he’s showing why simplicity and discipline are the ultimate edge in business and investing.
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