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Success and Mental Well-Being in Entrepreneurship — A Sit Down with Blake Mycoskie

October 20, 2026 Guest: Blake Mycoskie, Founder of TOMS Shoes

Show Notes

In this conversation, Doug sits down with Blake Mycoskie, the founder of TOMS Shoes, to talk about what it means to succeed and what can happen to a person's sense of self afterward.

Mycoskie reflects on rebuilding after selling his company, including losing his sense of purpose and his self-esteem along the way, and the mental health work he has taken on since.

He also talks about his latest project, Morning Water, a creatine-based hydration product.

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