My Favorite Mistake — 214: Entrepreneur Zak Waddell on Startup Mistakes and The Bachelorette

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My guest for Episode #214 of the My Favorite Mistake podcast is Zak Waddell. He’s a college success manager at Woolf — the first global, collegiate higher education institution allowing membership for qualified new colleges through their software platform.

A previous guest, Anthony Trucks, (Episode 97) was a contestant on American Ninja Warrior. Zak was a contestant on a show that might be even more grueling (at least mentally): The Bachelorette (Season 9)

In this episode, Zak shares his favorite mistake story about, as an entrepreneur, falling in love with a business idea instead of starting with the “voice of the customer” and their needs. In this startup, why was it so difficult to challenge the traditional commission-based real estate model? What assumptions turned out not to be true? What did Zak learn? How does the experience with that failed startup help him now?

We also discuss his experience as a contestant on The Bachelorette. Did he ever think it was a mistake to start that journey? What mistakes do contestants make? What mistakes might viewers make when watching a “reality” show? We talk about that and more in this most dramatic episode of My Favorite Mistake yet.

Questions and Topics:

  • Falling in love with an idea
  • Need to take a Iterative approach and listening to customers
  • What assumptions did you have to test?
  • What did you learn through cycles of learning…
  • Pivot or Pull the Plug??
  • Not vetting individuals… not stopping to think if it was the RIGHT team…
  • How to manage in less hierarchical ways?
  • Failed startup — really helped him for what he’s doing now
  • Rigorous iteration — failing fast, failing forward
  • Applying those lessons to future ventures or Woolf?
  • The Bachelorette — Was there any point when you felt like it was a mistake to sign up for this — before or during?
  • Do you try to learn from previous seasons or just do your own thing?
  • Why does it backfire when a contestant tries to report bad behavior to the Bachelorette?
  • A mistake as a viewer to think what you see is naturally occurring vs. stirred up by producers? And editors?
  • Is it by design that more couples from the show are getting married now?
  • Tried to apply entrepreneurship concepts on the show? Fall fast, fail often?
  • If asked to write a book about the lessons from the show for business?

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