#280: Blake Mycoskie, Founder, TOMS Shoes and ENOUGH – Stay connected to your why episode artwork

EPISODE · Feb 26, 2026 · 1H 5M

#280: Blake Mycoskie, Founder, TOMS Shoes and ENOUGH – Stay connected to your why

from How Leaders Lead with David Novak · host David Novak

Content Warning: This episode includes a candid conversation about depression and suicide.  If you or someone you know is struggling, you can call or text 988 to reach the Suicide & Crisis Lifeline. It’s free, confidential, and available 24/7. You’re not alone. — Blake Mycoskie built TOMS into a $700 million business with a simple idea: sell a pair of shoes, give a pair away to a child in need. But that success didn’t protect him from a seven-year battle with depression. And after selling TOMS, he lost his sense of purpose – and nearly lost himself. Today, Blake is back with a new mission: tackling the mental health crisis through his brand ENOUGH. And for him, staying connected to your “why” is important in business. But in life, it’s essential.  In this episode, Blake shares how to stay connected to a sense of purpose and galvanize a team around it, too. You’ll also learn: The marketing strategy that propelled TOMS faster than any traditional approach Why starting a business with zero experience might be your biggest advantage How to recognize the warning signs of depression (even if you “shouldn’t” be struggling) The daily mantra that’s guiding everything Blake does now Take your learning further. Get proven leadership advice from these (free!) resources: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠The How Leaders Lead App⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠: A vast library of 90-second leadership lessons to stay sharp on the go  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Daily Insight Emails⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠: One small (but powerful!) leadership principle to focus on each day Whichever you choose, you can be sure you’ll get the trusted leadership advice you need to advance your career, develop your team, and grow your business.

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#280: Blake Mycoskie, Founder, TOMS Shoes and ENOUGH – Stay connected to your why

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