Our guest today is Chris Tsakalakis. He's led some of the internet’s most recognizable platforms as CEO: StubHub, Vivino, and Kiva, after his stint in consulting at Bain. But his path to the top wasn’t a straight line, and it wasn’t always smooth.

The son of Greek immigrants, he spent his early years working for his father, learning the rhythms of labor before the language of business. He made his way through an Ivy League school, into Bain, and eventually into the upper ranks of eBay. Along the way, he learned how to lead through growth, through crisis, and through reinvention.

In this episode, we talk less about the milestones and more about what it took to get through them. Chris reflects on how his relationship with ambition changed over time, why identity can so easily get tied to a job title, and how personal setbacks - including major surgery and moments of professional doubt - reshaped how he thinks about success.

This isn’t a story about the rise of a CEO. It’s about what happens before the title comes and after it goes away.

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Samana is a term for people in ancient times who stepped away from the mainstream to pursue an ideal higher than themselves. On this podcast, we get to know modern-day samanas: ambitious professionals who carved a unique path, not because they failed, but because they were brave enough to ask better questions.

Brought to you by Vijay Wealth. Production and marketing by AQ Productions.

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(00:00) Opening

(00:22) Introduction to Samana

(01:14) Early Career and Identity at Bain

(05:10) Feedback, Insecurity, and Performance

(08:52) Imposter Syndrome and Growth

(13:00) Leadership and Vulnerability

(15:23) Redefining Success Beyond Titles

(22:49) Money, Parenting, and Values

(27:30) Separating Identity from Career

(31:39) Career Pivots and Following Curiosity

(37:40) Lessons from Vivino and Moving On

(40:39) Operating Principles and Daily Structure

(44:25) Investment Wins and Losses

(49:33) Legacy, Priorities, and Perspective

(51:13) Closing Reflections

Welcome to Samana - where we unpack the titles, the exits, and what comes after traditional success with the world's most successful people. We speak with trailblazers who’ve built and sold unicorns, are tackling humanitarian challenges, and are pushing the frontier of tech. People who’ve achieved what most only chase - and then asked, “Is this it?”"

Samana is named after people in ancient times who stepped away from the mainstream to pursue an ideal higher than themselves. On this podcast, we get to know modern-day samanas - ambitious professionals who carved their own path, not because they failed, but because they were brave enough to ask better questions.

Production and marketing by AQ Productions.