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Habits and Hustle

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NEW Episode 398 · Season 1 Nov 3, 2026 · 1 hr 15 min

Blake Mycoskie: What Happened After the $650 Million Success Story

Blake Mycoskie built one of the most recognizable purpose-driven brands in the world.Before TOMS, he was already a serial entrepreneur, launching businesses ranging from a college laundry service to online driver’s education. Then a trip to Argentina inspired an idea that would change his life: sell one pair of shoes and give another pair to someone who needed them.TOMS started with just $3,000 and grew into a global phenomenon, eventually giving away more than 100 million pairs of shoes.But while the company was exploding, Blake says he was quietly struggling.In this deeply personal conversation with Rachel Uchitel, Blake opens up about the pressure to constantly achieve, the external validation that never made him feel like he was enough, the effect that struggle had on his marriage, and the depression that followed the sale of TOMS.He also shares his experience being diagnosed with bipolar disorder, why he believes that diagnosis was incorrect, what happened after he began taking medication, and how close he came to ending his life before finding a psychiatrist who helped him begin rebuilding.Blake explains how confronting his own core wounds changed the way he approaches business, relationships and fatherhood, including the emotional conversation he eventually had with his children about the pressure he believes he unintentionally passed down to them.Today, Blake is still building companies, but he says success no longer determines his worth.He also talks about the Enough movement, his mental-health work, his podcast No Magic Pill, and a new business created alongside his daughter Charlie.This is the story behind the success story.Blake Mycoskie:https://blakemycoskie.com/Official site for Blake’s latest work, projects and writing.ENOUGH:https://blakemycoskie.com/enoughLearn more about Blake’s ENOUGH movement and bracelets supporting mental-health organizations.No Magic Pill Podcast:https://nomagicpill.com/Blake’s podcast featuring candid conversations about mental health, purpose and healing.Listen / Watch No Magic Pill:https://nomagicpill.com/subscribeLinks to Apple Podcasts, Spotify and YouTube.Morning Water:https://blakemycoskie.com/morning-waterLearn more about Morning Water, the daily wellness product Blake discusses in the episode.Blake’s Socials & Contact:https://blakemycoskie.com/connectInstagram, YouTube, TikTok, LinkedIn, X and Blake’s Substack can all be found here.TOMS:https://www.toms.com/--- --- ---Want some more BTS bonus content of Miss Understood? Join our patreon for Post Show Podcasts, Monthly Merch Giveaways and Weekly Bonus Episodes!https://www.patreon.com/c/MissUnderstoodwithRachelUchitelShop Miss Understood Merch https://missunderstoodpodcast.com/shop/PLEASE LIKE, SHARE, SUBSCRIBE, AND GIVE US A 5-STAR REVIEW!: ratethispodcast.com/missunderstood⁠⁠⁠⁠⁠⁠Follow Rachel on Instagram!⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ https://www.instagram.com/racheluchitelnyc/?hl=enFollow Rachel on TikTok! <a href="https://www.tiktok.com/@itsracheluchitel" target="_blank" rel="noreferrer...

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