The Wound Behind Success
Success did not protect Blake from depression.
Aug 25, 2026 · 54 min · 12 segments
Blake Mycoskie, founder of TOMS Shoes, joins Stan to discuss his entrepreneurial journey through the lens of negotiation, from losing The Amazing Race due to wrong assumptions to building TOMS’…
For listeners, um, that don't know your whole story, your first business was in college doing laundry at multiple universities.
I was the youngest person next to Ted Turner, who started CNN, to ever start a cable network.
And this I think is relevant 'cause I've been having to do a lot more negotiating in the past two years than maybe in the last ten.
Because in the last eighteen months, I've co-founded four companies and started a podcast.
It's like I went from nothing for seven years to, like, busier than I've ever been in my life, and, uh, and I'm loving it.
But it has had me to start, you know, thinking about negotiations and business and you know, how I think about doing things maybe differently than I did when I started Toms.
Um, you were on a trip down in Argentina, and one of the things I say to my students when they ask me, "How do I figure out what I'm passionate about? How do I figure out what my career should be?" I say, "Do the things that you care about and you're gonna meet people, you might find co-founders, you might get an idea." You were down in Argentina, um, I think, you know, at a polo camp of all things.
For listeners, um, that don't know your whole story, your first business was in college doing laundry at multiple universities.
I was the youngest person next to Ted Turner, who started CNN, to ever start a cable network.
And this I think is relevant 'cause I've been having to do a lot more negotiating in the past two years than maybe in the last ten.
Because in the last eighteen months, I've co-founded four companies and started a podcast.
It's like I went from nothing for seven years to, like, busier than I've ever been in my life, and, uh, and I'm loving it.
But it has had me to start, you know, thinking about negotiations and business and you know, how I think about doing things maybe differently than I did when I started Toms.
Um, you were on a trip down in Argentina, and one of the things I say to my students when they ask me, "How do I figure out what I'm passionate about? How do I figure out what my career should be?" I say, "Do the things that you care about and you're gonna meet people, you might find co-founders, you might get an idea." You were down in Argentina, um, I think, you know, at a polo camp of all things.
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3 of 14
The Wound Behind Success
Success did not protect Blake from depression.
Community That Kept Blake Alive
Community became Blake's lifeline during darkness.
The Dream Failed To Heal
The life he wanted still left him empty.
+11 more clips · 11 min 45 sec of audio in all
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