Why Stillness Beats Hustle (and Other Lessons from a $400 Million Rise and Fall) with James Beshara

What happens when you build a $400 million startup and then lose it all?

For James Beshara, the answer wasn’t another company. It was a complete rewiring of how to live.

In this episode, Healey Cypher sits down with the founder of Tilt (acquired by Airbnb) and Magic Mind to talk about the unseen side of ambition: the waves you catch, the ones you miss, and the peace that comes when you stop fighting the current.

James shares how public failure became the best thing that ever happened to him, why stillness is the ultimate competitive advantage, and how a decade of studying philosophy (Advaita Vedanta) reshaped his definition of success.

You’ll hear:

- How to build mental wealth the same way you build physical health

- Why “we don’t see the world as it is; we see it as we are”

- The founder trap of external validation and how to escape it

- The 90-minute morning ritual that keeps him calm in chaos

- Why work without attachment is a form of worship

- The story behind my $100 million mistake and what it taught him about ego

- The simple, radical truth that changed his life: “It’s not out there.”

This conversation is a rare blend of practicality and philosophy. It’s about ambition without anxiety, growth without ego, and finding meaning in the middle of the mess.

🎧 Listen now to this episode of “Don’t Be a Jerk” on your favorite podcast platform.