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49. What's Your Million-Dollar Blindspot?

One year ago today, we launched this podcast with a simple message: Dream Big. In this anniversary episode, we explore why the mythology of the solo entrepreneur is holding you back and how blind spots shape every founder's journey.

I share the story of a tech founder who lost everything in the dotcom crash and rebuilt his company with a radically different approach, ultimately selling for millions. This time around, he hired four advisors to help him see what he couldn't see alone. His coach's observation that he was "spending his own money," being too emotionally enmeshed with his business to make strategic decisions, transformed how he approached risk and investment.

We cover why "figuring it out on your own" becomes the exact bottleneck preventing growth and discuss the hidden costs of independence beyond just money: time spent learning expensive lessons, energy drained by invisible patterns, missed opportunities, and strained relationships.

Through examples from Diana Nyad's "solo" swim from Cuba to Florida and the support teams behind elite athletes, we see how no significant achievement is truly solo.

The key insight is that your blind spots aren't character flaws but the inevitable result of being inside your own psychology. The founders who accelerate past their limitations invest in outside perspectives and build teams of advisors who see what they cannot.

As the tech founder told me, "Experience is a great teacher, but it's damn expensive."

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