StockX Co-Founder Chris Kaufman on Why Empathy Isn't Soft (It's Just Smart Business)

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 advantageThe true cost of constant layoffs (it's way more than severance)What happens when "efficiency" becomes the enemy of innovationWhy vulnerability isn't weakness in leadershipThe Kanye visit, the first trades, and what it felt like when things started workingChris'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/3NL54K3Subscribe to The Sneaker Newsletter for Deep Dives on Sneaker Lore, Business Analysis, and Industry Insider Insight.Chapters00:00 Introduction to Chris Kaufman and StockX01:41 The Birth of StockX: From UpTo to Sneakers04:54 Understanding the Sneaker Market and Culture10:16 Challenges and Doubts in the Early Days13:58 The Impact of Timing on StockX's Success16:30 Personal Reflections on Sneakers and Self-Expression20:05 Building a Team and Culture at StockX24:17 The Power of Diverse Opinions and Collaboration29:37 Learning from Feedback and User Experience35:27 The Importance of Passion and Engagement38:35 Celebrating Team Achievements39:26 The Value of Open Conversations40:56 Nostalgia and Personal Connections in Sneakers42:09 The Evolution of Fashion in the Workplace43:45 Empathy in Leadership45:54 Creating a Psychologically Safe Workplace48:44 The Importance of Vulnerability in Leadership50:36 Encouraging Risk-Taking and Innovation52:42 The Role of Humor in the Workplace57:03 Balancing Work and Creativity59:54 The Creative Process and Iteration01:02:42 Long-Term Thinking in Leadership01:07:24 The Importance of Process in Creativity01:14:23 Creative Iterations and Team Culture01:17:59 The Importance of Listening to Employees01:20:45 Leadership and Employee Engagement01:23:12 Memorable Moments at StockX01:29:25 Current Projects and Future Aspirations01:35:28 The Journey of Writing a Book[Links contain affiliate links; we may receive a small commission if you purchase after clicking a link. A great way to support the pod!]—––––—––––—––––—––––—––––—––––—––––—––––Our podcast is proudly...Recorded on Riverside: http://www.riverside.fm/?via=sneakerhistoryHosted & Distributed By Captivate: https://bit.ly/3j2muPbMy Other Shows...For the Formula 1 Fans - Exhaust Notes: https://exhaustnotes.fmFor the Fitted Hat Fans - Crown and Stitch: https://crownandstitch.comFor the Cars & Sneakers Fans - Cars & Kicks: https://carsxkicks.comFor the Sneakerheads - Sneaker History: https://podcasts.apple.com/id/podcast/outside-the-box-convos-with-creators/id1050172106Disclaimer: 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.