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:
- Why StockX's early chaos was actually its competitive advantage
- The true cost of constant layoffs (it's way more than severance)
- What happens when "efficiency" becomes the enemy of innovation
- Why vulnerability isn't weakness in leadership
- 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:
- Chris Kaufman: https://www.christopherkaufman.com/
- 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 Workplace
43:45 Empathy in Leadership
45:54 Creating a Psychologically Safe Workplace
48:44 The Importance of Vulnerability in Leadership
50:36 Encouraging Risk-Taking and Innovation
52:42 The Role of Humor in the Workplace
57:03 Balancing Work and Creativity
59:54 The Creative Process and Iteration
01:02:42 Long-Term Thinking in Leadership
01:07:24 The Importance of Process in Creativity
01:14:23 Creative Iterations and Team Culture
01:17:59 The Importance of Listening to Employees
01:20:45 Leadership and Employee Engagement
01:23:12 Memorable Moments at StockX
01:29:25 Current Projects and Future Aspirations
01:35:28 The Journey of Writing a Book
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Disclaimer: The views and opinions expressed in this program are those of the speakers and do not necessarily reflect the views or positions of any entities they represent.
