Jim McKelvey co-founded Square with Jack Dorsey and built a billion dollar company.
Then Amazon came after them.
They survived.
In this episode Jim breaks down the Innovation Stack — the strategy that made Square uncopyable even by the world’s most powerful company.
This conversation will change how you think about building something that lasts.

Christopher Zook — Author of The Holy Grail of Investing (with Tony Robbins) — joins The Bigger Why to explore the future of alternative investing, enduring advantage, and long-term value creation.

Zook is one of the world’s leading thinkers on strategy and growth, best known for his work on enduring companies and his collaboration with Tony Robbins on The Holy Grail of Investing. In this conversation, we go deep on how alternative investing is evolving, what separates enduring businesses from the rest, and how investors and founders should think about the next decade of capital.

Topics we cover:

-The future of alternative investing
-What creates enduring advantage over decades
-Lessons from The Holy Grail of Investing
-Strategy, focus, and long-term decision-making
-Why most growth strategies fail—and what actually works
-Lesson from Tony Robbins
-Lessons from his Childhood
-Asset classes such as GP Stakes, private credit, private equity, venture capital, defense investing, sports investing and other niche asset classes

🎧 Listen to the full audio episode:

https://thebiggerwhywithsam.com

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About the Show

The Bigger Why is a long-form interview podcast hosted by Sam Weber, exploring meaning, purpose, strategy, and the stories behind enduring success—across investing, business, creativity, and life.

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