Blake Mycoskie Built TOMS, Gave It All Away, and Almost Didn't Make It. episode artwork

EPISODE · Apr 20, 2026 · 35 MIN

Blake Mycoskie Built TOMS, Gave It All Away, and Almost Didn't Make It.

from The Steve Weiss Journey · host Steve Weiss

Blake Mycoskie built TOMS Shoes from a vacation idea into a global movement — 100 million pairs of shoes given away, a company worth hundreds of millions, and a name that redefined what business could be. Then he sold it. And nearly lost everything inside. For almost seven years after the exit, Blake quietly fell apart. No company. No community. No identity. What looked like freedom was actually entrepreneur burnout in slow motion — until he hit a moment where he thought about taking his life. What rebuilt him wasn't a new startup. It wasn't another exit. It was two words on a bracelet. This is the story of what success actually costs — and what one of the most recognized entrepreneurs of his generation is building now that he's finally stopped running from himself.⸻⸻⸻⸻⸻⸻⸻⸻⸻Connect With Me!⸻⸻⸻⸻⸻⸻⸻⸻⸻🎙️ Subscribe for weekly conversations with entrepreneurs who've done it the real way.📩 Newsletter: the-next-chapter-today.beehiiv.com💼 LinkedIn: linkedin.com/in/stevejweiss📱 TikTok: @thesteveweissjourney0⸻⸻⸻⸻⸻⸻⸻⸻⸻Chapters⸻⸻⸻⸻⸻⸻⸻⸻⸻0:00 Intro4:33 The moment that almost broke him: Blake on hitting rock bottom after the exit5:29 "You are enough" — the bracelet, the wound, and the movement7:06 When vulnerability goes both ways11:50 Advice for post-exit founders who've lost their purpose21:47 How to build something that actually matters: purpose + profit23:28 Life as a video game: Blake's daily growth mindset26:05 Why empowering your competitors makes you stronger27:12 The case for vulnerability in business and in life29:33 The people behind the mission: Blake on Jill and the Enough org31:31 Blake's #1 concern about the world today: screen time

Episode metadata supplied by the publisher feed · Published Apr 20, 2026

Blake Mycoskie built TOMS Shoes from a vacation idea into a global movement — 100 million pairs of shoes given away, a company worth hundreds of millions, and a name that redefined what business could be. Then he sold it. And nearly lost everything inside. For almost seven years after the exit, Blake quietly fell apart. No company. No community. No identity. What looked like freedom was actually entrepreneur burnout in slow motion — until he hit a moment where he thought about taking his life. What rebuilt him wasn't a new startup. It wasn't another exit. It was two words on a bracelet. This is the story of what success actually costs — and what one of the most recognized entrepreneurs of his generation is building now that he's finally stopped running from himself.⸻⸻⸻⸻⸻⸻⸻⸻⸻Connect With Me!⸻⸻⸻⸻⸻⸻⸻⸻⸻🎙️ Subscribe for weekly conversations with entrepreneurs who've done it the real way.📩 Newsletter: the-next-chapter-today.beehiiv.com💼 LinkedIn: linkedin.com/in/stevejweiss📱 TikTok: @thesteveweissjourney0⸻⸻⸻⸻⸻⸻⸻⸻⸻Chapters⸻⸻⸻⸻⸻⸻⸻⸻⸻0:00 Intro4:33 The moment that almost broke him: Blake on hitting rock bottom after the exit5:29 "You are enough" — the bracelet, the wound, and the movement7:06 When vulnerability goes both ways11:50 Advice for post-exit founders who've lost their purpose21:47 How to build something that actually matters: purpose + profit23:28 Life as a video game: Blake's daily growth mindset26:05 Why empowering your competitors makes you stronger27:12 The case for vulnerability in business and in life29:33 The people behind the mission: Blake on Jill and the Enough org31:31 Blake's #1 concern about the world today: screen time

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Blake Mycoskie Built TOMS, Gave It All Away, and Almost Didn't Make It.

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Blake Mycoskie built TOMS Shoes from a vacation idea into a global movement — 100 million pairs of shoes given away, a company worth hundreds of millions, and a name that redefined what business could be. Then he sold it. And nearly lost everything...

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