Chris Kaufman is a Detroit-based creative leader, entrepreneur, investor, and author. As co-founder and former Chief Creative Officer of StockX, he helped scale the platform to a $3.8 billion valuation, serving customers in over 200 countries and facilitating billions in gross merchandise volume. Chris is also the bestselling author of 'Empathy at Work', where he breaks down how practical empathy drives innovation, retention, and long-term business success. In this episode, Chris shares how a paper route sparked his entrepreneurial mindset, the bold decision to walk away from a Yahoo acquisition, and how applying stock market mechanics to sneakers changed an entire industry.

On this episode we talk about:

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  The early entrepreneurial lessons Chris learned delivering newspapers in Detroit

  
  


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  Turning design into a business discipline

  
  


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  Walking away from a Yahoo acquisition to build something bigger

  
  


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  The core mechanics that made StockX explode globally

  
  


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  Why removing friction is the fastest path to scalable growth

  
  


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  How empathy fuels high-trust, high-performance teams

  
  

Top 3 Takeaways:

1. There’s always a better way to make money.

Manual labor teaches discipline — but entrepreneurship starts when you ask how to make income scalable.

2. Remove friction to unlock growth.

StockX succeeded because it eliminated guesswork: transparency, anonymity, and authenticity allowed buyers and sellers to transact with confidence.

3. Empathy is a competitive advantage.

Leaders who build with empathy see stronger innovation, better retention, and more sustainable growth over time.

Notable Quotes:

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  “There has to be a better way to make money than this.”

  
  


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  “Transparency changes behavior.”

  
  


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  “Empathy isn’t soft — it’s strategic.”

  
  

  
  

  
  

  Connect with Chris:

  
  

  Company: StockX

  
  

  Book: Empathy at Work

  
  

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