You remember the shoes. Those flat, canvas alpargatas that seemed to be on every college campus and in every airport terminal circa 2010. You probably bought a pair. Maybe you bought three. The pitch was perfect: you buy a pair, a kid in need gets a pair. Simple. Brilliant. It made us all feel like philanthropists while we were just shoe shopping.
But then, things got quiet.
If you look at TOMS Shoes today, the guy who started it all, Blake Mycoskie, isn't even running the show. In fact, he hasn't owned the company for years. While the brand is currently gearing up for its 20th anniversary in 2026 under new CEO Jessica Alsing, the story of how Blake Mycoskie went from the "Chief Shoe Giver" to a guy launching a mental health nonprofit called ENOUGH is a wilder ride than most business textbooks admit.
The Rise of a Disruptor
Blake wasn't a "shoe guy" by trade. He was a serial entrepreneur who had already started a laundry service, a billboard company, and a reality TV career—he actually came in second on The Amazing Race.
While vacationing in Argentina in 2006, he saw children without shoes. This wasn't just a comfort issue; it was a health issue. Soil-transmitted diseases were a constant threat. Instead of starting a charity that begged for donations, Blake had a thought: why not build a business that funds the solution?
He returned to his Venice Beach apartment with 250 pairs of local alpargatas. He called the company TOMS, short for "Tomorrow’s Shoes."
It exploded.
By 2014, TOMS was a global powerhouse. But here is the thing about rapid growth: it’s expensive. To scale, Blake sold a 50% stake to Bain Capital. At the time, the deal valued the company at roughly $625 million. Blake walked away with about $200 million after taxes, but he stayed on as the face of the brand.
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When "One-for-One" Stopped Working
For a long time, the model was the golden child of social entrepreneurship. But critics started poking holes in it.
The biggest argument? Handing out free shoes can actually hurt local economies. If a local cobbler is trying to sell shoes to support his family, he can’t compete with a giant American company giving them away for free. It’s a "band-aid" solution that doesn't address why the families are poor in the first place.
Blake listened. To his credit, he tried to adapt. TOMS started manufacturing some of their "giving shoes" in the countries where they were being distributed. They expanded into eyewear and clean water.
But the business side was struggling.
By 2019, the hype had faded. Heavy debt and shifting fashion trends meant the company was staring down bankruptcy. In a massive restructuring, Blake Mycoskie and Bain Capital handed over their remaining ownership to creditors—Jefferies Financial Group, Nexus Capital Management, and Brookfield—in exchange for debt relief.
Just like that, the founder was out of his own company.
Where is Blake Mycoskie Now?
Honestly, the transition was brutal for him. Imagine building a brand that defines your entire identity, and then suddenly, you're just a guy in a big house with a lot of money and no "mission."
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Blake has been incredibly open recently about the "scary depression" that followed. He realized that even after giving away 100 million pairs of shoes, he didn't feel like he was "enough."
This personal crisis led to his latest venture. In January 2026, Blake officially launched ENOUGH, a nonprofit lifestyle brand focused entirely on mental health.
It’s a different beast than TOMS.
- 100% of proceeds go to mental health partners like NAMI and Active Minds.
- The primary product is a beaded "ENOUGH" bracelet set.
- It operates on a "pay-what-you-can" model for those who can't afford the $58 price tag.
He’s not trying to build another billion-dollar empire. He’s trying to normalize the conversation around the "invisible" struggle of mental illness. He’s basically using the same "commerce for good" engine he pioneered with shoes, but he’s stripped away the private equity and the corporate overhead.
The 2026 Reboot of TOMS Shoes
While Blake is doing his thing, TOMS is trying to find its soul again.
The company officially killed the "One-for-One" model in 2019. It was a shock to the system, but it was necessary. Now, they give one-third of their profits to grassroots organizations. It’s less "catchy" for a marketing slogan, but many experts argue it’s a more sustainable way to fund systemic change.
In late 2025, Jessica Alsing took over as CEO. Her mission for 2026? Make the Alpargata "hot" again.
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They are leaning into nostalgia but adding tech. You’re going to see things like "CloudBound" insoles—essentially memory foam with arch support—because let's be real, the original TOMS weren't exactly known for their ergonomics. They are also chasing Gen Z, focusing on sustainability and causes like ending gun violence.
Actionable Insights: Lessons from the TOMS Saga
If you’re an entrepreneur or just a fan of the brand, there are some pretty heavy lessons to take away from Blake’s journey.
1. Your Business Model Must Evolve
The "One-for-One" model was a masterclass in marketing, but it wasn't a perfect solution for poverty. Don't get so married to your "hook" that you ignore the actual impact (or lack thereof) it’s having on the ground.
2. Separate Your Worth from Your Work
Blake’s struggle post-TOMS is a cautionary tale. If your "purpose" is tied entirely to your job title, you’re in trouble the moment that title goes away.
3. Direct Cash is Often Better than Goods
TOMS’ shift from giving shoes to giving a percentage of profits reflects a broader trend in philanthropy. Giving local organizations the money to solve their own problems is almost always more effective than shipping in physical products from the outside.
4. Transparency Trumps Perfection
One of the reasons Blake remains a respected figure despite the business's stumbles is his honesty. Whether he's talking about his depression or the failures of the early giving model, he doesn't hide behind PR-speak.
TOMS changed the way we think about shopping. It proved that people want their money to mean something. Whether the brand can reclaim its Y2K-era glory in 2026 remains to be seen, but the "business with a purpose" movement Blake Mycoskie kickstarted isn't going anywhere. It's just growing up.
Next Steps for You
- Audit your giving: If you run a business, look at whether your "social impact" is actually helping the community or just looking good in an Instagram ad.
- Check out the new model: Look into the TOMS 2024/2025 Impact Report to see how the "1/3 of profits" model actually distributes funds compared to the old shoe-giving days.
- Prioritize mental health: If you're feeling the "founder burnout" Blake described, look into resources like National Alliance on Mental Health (NAMI) before the "empty" feeling sets in.