267: How TOMS Founder Blake Mycoskie Blazed a Trail for Social Entrepreneurs

267: How TOMS Founder Blake Mycoskie Blazed a Trail for Social Entrepreneurs

Blake Mycoskie had a number of hits and misses as a young entrepreneur, but it was a trip to Argentina that inspired the idea that would become his mission—and end up having a huge impact on the business world. Mycoskie wanted to find a way to help the children he encountered who didn’t have proper footwear, but he wanted to do it in a for-profit, self-sustaining way. That’s how TOMS came to life. From there, Mycoskie blazed a trail in the way companies think about social good, by popularizing the one-for-one giving model and building the beloved brand that still exists today. TOMS generates hundreds of millions in sales and still stays true to its mission of giving back to communities around the world. Check out this episode to learn more about Mycoskie’s advice for those who want to pursue social entrepreneurship, the business model that led to his success, and the expansion of TOMS into other types of products. Key Takeaways Why the idea of a “job” was foreign to Mycoskie growing up How Mycoskie’s entrepreneurial spirit led to him founding everything from a laundry service to a reality cable television channel The trip to Latin America that inspired the idea for TOMS Shoes How Mycoskie changed the social entrepreneurship game with his one-for-one model Why social good isn’t necessarily the right path for every business Mycoskie’s personal reasons for selling half of TOMS to Bain Capital How TOMS was able to grow completely organically through social media when it launched in 2006 The journey to achieving millions in revenue and donations The reasons behind TOMS’ expansion into eyewear, coffee shops, and more How Mycoskie continues to innovate despite a lack of background in apparel design Mycoskie’s best advice on choosing the right partners and building a sustainable business

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623: $500K in Debt, 5 Maxed Credit Cards — How Jordan Harper Built an 8-Figure Brand in Year One

623: $500K in Debt, 5 Maxed Credit Cards — How Jordan Harper Built an 8-Figure Brand in Year One

Jordan Harper built an eight-figure skincare brand in its first year by maxing out five credit cards while already $500,000 in debt — and never raised a single dollar from investors. In this inter...

15 Tammi 53min

622: (Solo) The Truth About Founder-Led Content in 2026

622: (Solo) The Truth About Founder-Led Content in 2026

Founder-led branding isn’t dead — but it is evolving fast. Showing your face and posting “day in the life” content is no longer enough to stand out. The bar has risen, audiences have matured, and what...

13 Tammi 8min

621: We Bet $200K on Bras Before Making a Single Sale — Sold 400,000 in 2 Years | Nala

621: We Bet $200K on Bras Before Making a Single Sale — Sold 400,000 in 2 Years | Nala

Nala was built by two founders with no fashion background who invested $200,000 before making a single sale and went on to sell over 400,000 pieces in just two years. In this interview, Chloe and ...

8 Tammi 49min

620: (Solo) The Secret to Making Bold Business Moves With Confidence

620: (Solo) The Secret to Making Bold Business Moves With Confidence

One of the biggest challenges founders face — especially at the end of the year — is knowing what to do next and feeling confident that the move you're about to make is the right one. Certainty feels ...

6 Tammi 11min

619: Airline Charged Me $65 - So I built a $250M Competitor | Adam Ewart

619: Airline Charged Me $65 - So I built a $250M Competitor | Adam Ewart

Adam Ewart turned a £50 excess baggage fee into a global bootstrapped logistics company operating in 145 countries and staying profitable for 15 straight years. In this interview, Adam breaks down ...

1 Tammi 47min

618: (Solo) What 5 World-Class Founders Taught Me This Year

618: (Solo) What 5 World-Class Founders Taught Me This Year

Every year I sit down with some of the world’s most fascinating founders — but this year’s interviews hit me harder than most. Reinvention, resilience, copycats, failure, loneliness after exits, scrap...

30 Joulu 202511min

617: How A Failing Skincare Brand Became An 8-Figure Makeup Empire | Aliett Buttelman

617: How A Failing Skincare Brand Became An 8-Figure Makeup Empire | Aliett Buttelman

Aliett Buttelman spent eight years grinding in the dark before a single viral moment with Taylor Swift turned Fazit into an overnight seven-figure brand. In this interview, Aliett breaks down the ...

25 Joulu 202552min

616: (Solo) 5 Honest Business Lessons I’m Taking Into 2026

616: (Solo) 5 Honest Business Lessons I’m Taking Into 2026

2025 has been one of the most eye-opening years of my founder journey — personally, professionally, and strategically. Instead of sharing a highlight reel, I want to share the real lessons that moved ...

23 Joulu 20258min

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