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.