My Favorite Mistake — 193: Why CEO and Investor Kurt Wilkin is a “Proud Mistake Maker”

CEO of HireBetter and managing partner of Bee Cave Capital.

Episode page with video, transcript, and more

My guest for Episode #193 of the My Favorite Mistake podcast is Kurt Wilkin, a co-founder and CEO of HireBetter and managing partner of Bee Cave Capital. His bio says he’s “coach, mentor, entrepreneur… and proud mistake-maker.”

Prior to founding HireBetter, Kurt founded and led The Controller Group (TCG), a professional services firm focused on accounting, technology and recruiting, which was acquired by Tatum in 2006.

He’s the author of a new book, Who’s Your Mike?: A No-Bullshit Guide to the People You’ll Meet on Your Entrepreneurial Journey. You can learn more at

In this episode, Kurt tells his favorite mistake story about not having a complementary “execution partner” to help him run a business. How (and why) did he adjust? Why did he step aside from the CEO role and what did he learn from this entire experience that serves him well today?

We also talk about questions and topics, including:

  • What does it mean to you to be a “proud mistake maker”??”
  • How do you try to create a culture where people can also be proud mistake makers? Leading by example?
  • Investing in people who are humble enough to learn…
  • Learning from mistakes vs. avoiding company-killing mistakes?
  • You’ve said that you saw your dad struggle as an entrepreneur. Were you able to learn from any of his mistakes?
  • You joined a failed startup in the dot-com bubble… any lessons learned from that?
  • Mistake to try to swing for the fences vs. lifestyle cashflow positive business
  • TELL US ABOUT THE BOOK: A business book for people who hate business books?

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