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Chris Kaufman co-founded StockX and helped build it from the very beginning in a Detroit office to a global marketplace. But this conversation isn't all about that origin story... it's about what he learned watching companies choose short-term profits over long-term culture, and why he wrote a book about empathy at work.

We talk about the early StockX days when disagreement was productive, not destructive. About why firing people every 18 months to hit quarterly targets actually costs more than just keeping your best people. About the difference between being a CEO and being a leader. And about why the most powerful thing you can say as a leader might be "I dropped the ball on this."

Chris has seen both sides... the scrappy startup that valued every voice, and the scaled company where efficiency replaced humanity. He's worked with founders who get it and founders who don't. And his take on what actually makes teams work is refreshingly honest.

If you've ever felt like workplace culture is just corporate speak for "free snacks and ping pong tables," this conversation will change your mind. If you've ever wondered why your company keeps restructuring instead of just... building something, you'll recognize the patterns Chris calls out.

And if you've ever tried to lead people while also being a human being yourself, you'll appreciate how real this gets.

Topics:

1. Why StockX's early chaos was actually its competitive advantage
2. The true cost of constant layoffs (it's way more than severance)
3. What happens when "efficiency" becomes the enemy of innovation
4. Why vulnerability isn't weakness in leadership
5. The Kanye visit, the first trades, and what it felt like when things started working

Chris's book is "Empathy at Work," and yes, it's actually good. Not corporate handbook good... actually useful good.

This is the first episode of whatever I'm calling this show. Outside The Box, Pursuit of Something, The Nick Engvall Podcast, Unplanned Entrepreneur... still figuring it out. Let me know what you think it should be called.

Links:

1. Chris Kaufman: https://www.christopherkaufman.com/
2. Empathy at Work (book): https://fave.co/3NL54K3

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Chapters

00:00 Introduction to Chris Kaufman and StockX

01:41 The Birth of StockX: From UpTo to Sneakers

04:54 Understanding the Sneaker Market and Culture

10:16 Challenges and Doubts in the Early Days

13:58 The Impact of Timing on StockX's Success

16:30 Personal Reflections on Sneakers and Self-Expression

20:05 Building a Team and Culture at StockX

24:17 The Power of Diverse Opinions and Collaboration

29:37 Learning from Feedback and User Experience

35:27 The Importance of Passion and Engagement

38:35 Celebrating Team Achievements

39:26 The Value of Open Conversations

40:56 Nostalgia and Personal Connections in Sneakers

42:09 The Evolution of Fashion in the...

Outside The Box is back. I'm talking with people who are in the pursuit of something... building brands, chasing dreams, navigating the gap between passion and paying bills. This episode explains why I'm bringing the show back, what's changed, and how it connects to going full-time as a creator in 2026. If you're pursuing a passion that matters to you, these conversations are for you.

Subscribe to The Sneaker Newsletter for industry deep dives and vault stories from 20 years in the business: https://www.TheSneakerNewsletter.com