702: Blake Mycoskie (Founder of TOMS) - Hitting Every Goal & Still Feeling Worthless... Gratitude, Mantras, and Hiring Like a Champion

The Learning Leader Show with Ryan Hawk

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Blake Mycoskie founded TOMS Shoes in 2006 after a trip to Argentina, where he saw children without shoes and built a company around giving away a pair for every pair sold. TOMS went on to donate more than 100 million pairs of shoes and became one of the most copied business models in the world. What most people don't know is what happened after he sold it, and I'm grateful that he was open to talking about that on this episode of The Learning Leader Show.

Key Learnings

Make your gratitude specific. Not "I'm grateful for my family." Name the exact thing. Blake's example from that morning: the photos the camp posted of his daughter laughing in the lake, and knowing his stoic kid does not smile like that unless she is genuinely happy.

He kept the practice going for five years when he couldn't feel any of it. Blake could not name five things he was grateful for, and he had all the same things in his life he has now. He did it anyway. He credits it as one of the things that kept him going.

Surfing is a great thinking practice. Surfing is mostly just sitting on the board. Three hours in the water, ten waves, maybe five minutes standing. The rest is paddling and sitting. That's why it works as a thinking practice.

Capture the idea in the moment or lose it. Blake programmed the side button on his Apple Watch to open a voice memo. Every idea he has sitting on the board, he records. They're all waiting when he gets out.

He hit every marker and still felt worthless. "I did everything, and I still, deep down in my soul, had this feeling like I'm not worthy, I'm not enough, and I never will be."