Hey everyone,

Welcome back for another bite to chew on.

Billion-dollar brands have a predictable pattern. Once they gain the success, they get comfortable. They hire consultants. They build processes. They stop getting their hands dirty with the fundamentals.

True Classic, the billion-dollar men's apparel brand, did the opposite.

Co-founder and Chairman, Ryan Bartlett, and his co-founder, Ben Diamond, built a company that operates like it's still scrappy—even at billion-dollar scale. 

They diversified away from Meta without killing performance. They know when to hire experts instead of burning cash on failures. They start each day asking what they can learn that they didn't know yesterday.

The result? A brand that keeps growing because it never stopped being hungry.

Today we're breaking down the 3 systems that keep True Classic operating like a startup at billion-dollar scale. Let's get into it.

On the Menu:

P.S. You can watch our episode with Ryan here:

Listen on Spotify 🎧 and Apple 🍎 as well.

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Here's something that would give most D2C founders nightmares: True Classic is pulling back considerably on Meta for the first time in 6 years.

The crazy part? Their business isn't suffering at all.

We’ve all been there—Meta makes some random algorithm update, doesn’t tell anyone, and your entire acquisition strategy crumbles overnight. 

For True Classic, those early Meta crashes almost killed the business. And Ryan realized you can’t build a billion-dollar company on one platform’s mood swings.

But here’s what they did differently: instead of scrambling for the next Meta, they doubled down on brand strength: 

They obsessed over the fundamentals until they were bulletproof.

Now, wholesale is 10-15% of their business and targeting 20-30% next year. AppLovin is giving them profitable reach beyond Meta. Each new channel amplifies their brand work instead of competing with Meta for the same customers.

The Takeaway

You can't diversify away from bad unit economics, but you can diversify away from platform risk. 

So, stop chasing Meta hacks. Start auditing your basics:

Fix those, then expand.

If Meta shut down tomorrow, would your business still stand?

Ryan will be the first to tell you, True Classic failed at women's products multiple times before getting it right.

The problem? They kept trying to adapt men's t-shirt designs for women. 

When they asked for feedback, women told them they don't even wear t-shirts that much. They want tank tops, crops, leggings, activewear. 

But Ryan filtered this through his own perspective, so the execution missed.

At first, the team thought they could figure it out by iterating. After all, that’s how they cracked men’s tees—test, fail, refine, repeat. 

But women’s apparel was a completely different category. Each failure meant wasted time, bad inventory, and customers losing trust.

That’s when they realized the cost of DIY learning was compounding faster than the benefits.

So they hired an expert in women's clothing—Sawako Yamauchi-Tully, who had 13+ years building children's apparel brands. 

She understood the market intuitively and had designed products that women actually wanted.

And customer response flipped from "never again" to "finally, this is what we've wanted."

That experience is what shaped Ryan’s decision-making framework:

Hiring Sawako saved True Classic 18 months of expensive mistakes and let them enter women’s apparel successfully instead of burning cash on products nobody wanted.

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Here's a question every scaling founder faces: how do you keep learning fast enough to stay ahead of your business? 

Most entrepreneurs assume they need to figure everything out themselves. Not Ryan—he built a system for learning from existing winners. 

When he had zero ecommerce experience, he spent a year in Facebook groups studying successful operators. 

He asked questions constantly, identified what worked across different approaches, and extracted the principles that mattered. This systematic approach taught him the entire business faster than trying to learn it alone. 

At True Classic, this became their daily operating system. Ryan and Ben start every day asking:

What can we learn today that we didn't know yesterday? 

That single question drives everything. It pushes them to seek knowledge from other operators, test new approaches, and stay curious instead of assuming they have all the answers. 

The result: When new problems hit, they already have a system for finding solutions fast.