In just five years, Ryan Bartlett and his Cofounders transformed a simple idea—“make a better t-shirt for men”—into True Classic, a clothing brand now approaching $1 billion in revenue. With a $3,000 investment and no fashion background, Ryan leaned on his expertise in audio design and digital marketing to grow True Classic into one of Shopify’s fastest-growing brands.
His laser-focused content marketing strategy evolved alongside the business but never strayed from its core principle: content that converts.
Ahead, explore the specific content strategies that skyrocketed True Classic to success, with actionable insights for marketers and founders.
How True Classic created the ultimate content marketing strategy
From early Facebook ads to viral comedy, True Classic’s content engine was built to perform. Here’s how Ryan and his team turned t-shirts into a household name—and what you can learn from their approach.
1. Use early content to prove you can solve a problem
Ryan was brutally clear about his initial approach to content: “Early on, you have no choice but to make content that converts. That is just kind of the reality.” With limited resources, True Classic couldn’t afford to create content that didn’t directly drive sales. Initially the content focused on solving three key problems:
- Fit issues: Men’s t-shirts that actually fit properly
- Comfort: Superior fabric and construction
- Price: Premium quality without the premium price tag
“So I was solving three problems, and I had to get that across in the early content to sell t-shirts,” Ryan says. Every ad was built around clearly communicating value and solving a customer problem.
2. Experiment with paid ads
Of True Classic’s initial $3,000 investment, approximately $2,000 went directly to Facebook ads. Ryan’s background in digital marketing gave him a significant advantage.
“I knew how to hack Facebook ads,” Ryan says. “I knew how to flip the money, spend $25, make $50, and so on and so on. So we started out, spent 50 bucks a day, and made $100 or $300. It was in the early days, everything was like three or four to one. It was really amazing ROAS [return on ad spend].”
The True Classic approach was simple but effective: start small with $25 to $50 per day to test concepts, reinvest profits by using revenue to fund more ad spend, and rapidly scale winners by increasing budget quickly when an ad performs well.
“Very quickly, within a few weeks I was spending $150 a day and then $200 a day. And as long as the ROAS was somewhere between two to three to one on what I was spending, we were profitable,” Ryan explains.
Identify the platform where your target audience is most accessible and develop deep expertise in that platform’s advertising mechanics. Facebook ads provided the growth engine True Classic needed to scale rapidly from day one.
3. Evolve your content mix overtime
Even as they grew, Ryan knew mixing in brand-building content was important. The brand continues to maintain a disciplined content mix, still heavily weighted toward direct response.
“Even at our stage, you’d be surprised to know that 90% of our ads are still DR [direct response],” Ryan says. “Even though most of what you see is comedy and stuff out in the wild. We rely so much on just converting people on these platforms because it drives the business.”
To this day, he continues to test and shift the mix of content. “I made this test about a month ago where I said, ‘You know what? We’re big enough now. We’re just gonna go all brand and see what happens.’ It was a disaster.’
Even established brands need conversion-focused content to drive consistent sales. While brand-building content adds character, it’s important to strike a balance so you’re not taking time away from direct response, sales converting content.
True Classic’s current content framework is still the same. “Approximately 90% of content focuses on direct conversion, while just 10% builds brand awareness and affinity,” Ryan says.
Even as your brand matures, maintaining this balance—perhaps gradually shifting the ratio but never abandoning direct response entirely—is crucial for sustainable growth.
4. Use comedy!
“A great ad needs to feel real. It needs to feel like you’re not overselling,” Ryan says.
One of True Classic’s most distinctive content strategies is its use of humour. While maintaining its focus on conversions, it’s developed a unique voice that makes its ads stand out.
The comedy approach serves several strategic purposes. First, it creates shareability. “Comedy is the ultimate equalizer, and it’s also the only form of ad people are gonna share at scale,” Ryan says. It also supports brand alignment. “If we’re living by the look good, feel good mantra of True Classic—if we can make the ad allow them to feel good—then that’s the best version of an ad.” Lastly, it enables natural product integration: “You have to have something in there about the product, right? It can’t just be comedy for comedy’s sake,” Ryan shares.
5. Challenge content assumptions
True Classic has found success with static images challenging conventional wisdom about content formats. While many brands assume video content is always superior for social media advertising, True Classic has found surprising success with static images. “Right now, I’m finding that statics are just crushing. It’s very kind of old-school thinking, but like basically just a picture of a shirt,” Ryan says.
The brand’s most effective static ads include social proof elements like review counts. Ryan says these ads allow people to connect the dots and say, “Oh, clearly a lot of people are buying this. I should go check it out."
Their experience shows the value of testing different approaches—static versus video, long form versus Short form—to determine what actually drives results for your specific audience rather than following industry trends uncritically.
6. Bring your content team in-house
True Classic initially relied heavily on Ryan’s direction—but as they’ve grown, they’ve built both in-house capabilities and strategic agency partnerships to manage the volume of content.
“I had a friend who founded a big company just yesterday ask me, ‘I saw you guys use this agency. Should I use them?’ And I said, ‘Listen, we only used them because we needed, like, significant volume. No one’s gonna do better than you. You know the brand better,’” Ryan says.
Developing content in-house at the start is a great way to establish your brand voice and creative direction. Ryan suggests only engaging agencies when you need additional production capacity, not for strategic direction. Maintain a clear brand vision internally, and allow the in-house team to drive creation for as long as possible.
As True Classic approaches billion-dollar status, it’s its authentic brand voice that has helped it stand out in a crowded marketplace. Remember, sometimes old-school approaches like static images can outperform video. What matters most, is the relentless focus on keeping your content strategy aligned with business growth while preserving a distinctive brand voice.
True Classic’s success proves that with the right content approach, even the most basic product can become the foundation for extraordinary growth. Catch the full interview on the Shopify Masters YouTube channel to discover more of Ryan’s marketing tips and hear how he worked his way out of a $40 million bet gone wrong.
