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How Leaders Lead with David Novak

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

How Leaders Lead with David Novak

David Novak Leadership

Entrepreneurship, Business, Management

4.8596 Ratings

🗓️ 26 February 2026

⏱️ 65 minutes

🧾️ Download transcript

Summary

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.

Transcript

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0:00.0

Hello everyone and welcome to another episode of How Leaders Lead with David Novak.

0:04.9

Today's guest is Blake Mikoski. And you might remember Blake as the founder of Tom's Shoes,

0:10.6

which is a brand that really helped redefine how people think about business and impact.

0:16.4

Blake grew Tom's shoes to a $700 million business based on a simple idea, sell a pair of shoes

0:23.2

and give a pair of shoes away to a child in need. Now that success didn't protect Blake from

0:29.0

a seven-year battle with depression. And after he sold Tom's, he really lost his sense of purpose

0:35.4

and nearly lost himself.

0:40.0

Today, Blake is back with a new mission.

0:43.4

He's tackling the mental health crisis through his brand, Enough,

0:46.8

which seeks to empower people to talk about how they're really doing so that everyone in this world feels a little less alone,

0:50.4

and everybody knows that they are enough.

0:53.4

For Blake, staying connected to your why

0:55.8

is absolutely critical in business,

0:58.5

and it is essential in life.

1:01.3

Enjoyed this conversation between David and Blake,

1:03.4

and I will see you at the very end of the episode

1:06.0

for the debrief.

1:19.5

Before we get into Tom's, you know, and what you're doing with enough, both fantastic causes, you know, I want to take you back a little bit. What's the story from your childhood

1:25.9

that shaped the kind of leader you are today?

1:28.5

I mean, I think it really was just having amazing parents.

1:32.5

You know, my dad was a doctor and a great leader in his community and the hospitals that he helped, you know, run.

1:41.1

And my mom wrote a cookbook and sold millions of copies of it and helped people with

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