Can Money Buy Happiness? with Blake Mycoskie

Alive with Steve Burns

Lemonada Media

Society & Culture

5.0 • 588 Ratings

🗓️ 15 April 2026

⏱️ 55 minutes

🔗️ Recording | iTunes | RSS

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Summary

Blake Mycoskie opens up about building TOMS Shoes, chasing success, and still feeling empty. He unpacks the hidden cost of validation, the crash that followed, and how he’s redefining purpose, connection, and what it actually means to feel like enough. Together, Steve and Blake dig into the quiet pressure of chasing validation, how identity gets tangled up in achievement, and the crash that can follow when external rewards stop delivering. Blake talks candidly about the crushing toll it took on his mental health, and his long path to finding a greater sense of inner peace. --------------------------------------------------------------------- ** if you like this episode, then check out these ** Rainn Wilson on Faith https://youtu.be/8Vid5ZHaBlg Depression with Jessi Gold https://youtu.be/U4KGIjd9LY0 --------------------------------------------------------------------- Exclusive Offers For Our Listeners: Get 15% off your first order plus free shipping at BollAndBranch.com/alive with code “alive”. Sign up and get 10% off at betterhelp.com/stevealive. --------------------------------------------------------------------- Alive with Steve Burns - Season One Episode 26 | Blake Mycoskie Instagram: @alivewithsteveburns TikTok: @alivewithsteveburns --------------------------------------------------------------------- There are a thousand podcasts you can listen to. This one listens back. Alive with Steve Burns continues the conversation you began all those years ago. Back then it was letters and numbers and graham crackers. Now it’s death, sex, taxes, and all the big, messy questions of being alive. Why does money stress us out? Is the American dream dead? What’s the future of truth? Each week, a new guest drops by Steve’s window for a genuine and respectful dialogue between two people just trying to figure it out, together. Funny, tender, and just a little weird, this show invites you to sit down and think with Steve once again and wonder… what it really means to be Alive. --------------------------------------------------------------------- You are not alone. You are cared for. If you need someone to listen: National Suicide and Crisis Hotline: https://988lifeline.org/ NAMI Helpline: https://www.nami.org/nami-helpline/ Crisis Text Line: https://www.crisistextline.org/ Keywords: Blake Mycoskie, TOMS Shoes, entrepreneurship, startup founder, purpose-driven business, feeling enough, depression, success vs fulfillment, identity and success, burnout, mental health, imposter syndrome, validation, meaning and purpose, redefining success, personal growth, self-worth, authenticity, life after success, finding purpose in life, feel fulfilled, Steve Burns, Blues Clues #BlakeMycoskie #Entrepreneurship #MentalHealth #Success #Purpose Watch full episodes of Alive on YouTube. Stay up to date with Lemonada on Twitter, Facebook, and Instagram at @LemonadaMedia. If you haven’t yet, now is a great time to subscribe to Lemonada Premium. You’ll get ad-free episodes and bonus content from Steve. Just hit the 'subscribe' button on Apple Podcasts, or, for all other podcast apps head to lemonadapremium.com to subscribe. Click this link for a list of current sponsors and discount codes for this show and all Lemonada shows: lemonadamedia.com/sponsors

Transcript

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0:00.0	When I sold Tom's and I thought I had accomplished everything, I'd done everything I can, I helped a hundred million children get a pair of shoes.
0:13.9	Like I should have felt enough. And when I didn't, that's when things really started to come crashing down.
0:30.5	Okay. That's when things really started to come crashing down. Hey, there you are. Come on in.
0:33.9	Great to see you.
0:37.2	Welcome to live
0:39.5	so
0:41.4	of course I have a question for you today
0:44.6	and it's a heavy one but if you've
0:46.2	been with this pod for a while
0:49.0	you know that's what we do so I'm just going to jump in
0:51.5	do you ever feel like you're not enough?
1:07.8	Yeah, I mean, even just asking that question feels like you know because I have definitely felt
1:13.9	that way in my life you know feeling like I'm not enough was a defining feature in my life for a little
1:20.0	while it's a yucky feeling and I think it's one that a lot of people share I made tea by the way
1:24.6	do you want tea there's some. And lately I've been wondering
1:30.0	what we even mean by that, right? Like enough to who? Enough to ourselves, enough to each other.
1:39.1	Enough to the one bazillion people that we seem obsessed with on the internet um and so i had this amazing
1:47.9	conversation with someone who has placed this concept of being enough at the very center of his
1:55.9	life the center of his work of his purpose and have to say, it was a really inspiring conversation.
2:03.6	And I think you should check it out.
2:06.5	So here's your tea.
2:09.0	Give it a listen.
	...

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