True Classic CEO Ryan Bartlett Built The Ubiquitous $250 Million Brand Following This Unconventional Advice

True Classic founder and CEO Ryan Bartlett didn’t dream of building a clothing empire—he dreamed of being a famous producer. But despite having obtained a graduate-level education in the music business, when faced with the disenchanting realities of the industry he decided to reconsider: “You see working with Eminem, but in reality you’re cleaning toilets and picking up garbage and getting food for people—all for free.”

Scraping by as a musician at the time, and uncertain what to do next, Bartlett leaned into his affinity for poker. He tells the story of how he moved to Las Vegas, where he “promptly went broke,” then transitioned to the nightclub industry only to quickly burn out.

Frustrated and aware his next career move likely required retraining, Bartlett returned to school for computer science at the suggestion of his parents. In his mid-twenties at the time, he credits this decision as paving the way for his entrepreneurial success. During his next gig as a developer at an SEO company, he saw opportunity in the landscape and he and his brother started SEO Direct, an agency of their own.

But five years into SEO Direct, Bartlett felt uninspired. “I didn’t feel like I was making a purposeful life,” he shared. He was drawn to consumer goods, which he believed “create something of real value and connect to people.” He returned to an idea that had come to him nearly twenty years prior: “A t-shirt that isn’t overpriced, but still is elevated enough to where you feel like you’re not going to throw it away after ten washes.”

And with that, True Classic was born. Bartlett and his cofounders did $20,000 in revenue in their first month, validating that they were onto something. By the end of their first year, they’d sold $15 million of apparel; their second year revenue jumped to $90 million. And it 2023, True Classic brought in $250 million of revenue.

How exactly did he do it? Reflecting on his journey, the failed musician highlights four unconventional strategies that led to his entrepreneurial success:

1. Give up on your “dream.”

Following our dreams is the avenue to success, right? Not according to Bartlett. ““I wish I’d started earlier. I followed the model of “Follow your dreams”–and I went into debt,” he recounts.

Instead, he advocates for leaning into one’s passions during our spare time: “I realized that I can just play music in my own time for my kids. I can still do this at home and love it. I don’t have to make a living out of it. That’s what I would’ve told my younger self.”

2. Bootstrap, stay lean, and say “No” to venture capital funding.

Bartlett believes that proving oneself and establishing a successful company with limited resources is crucial before seeking external investment. He and his cofounders bootstrapped True Classic by investing only $3k and doing everything themselves for the first thirteen months. “I just didn’t know any different,” he explains. “I didn’t come from that world. I built SEO direct w no money. If you have grit, you’ll figure out a way out of no way [sic].”

He goes on to share his candid thoughts on venture capital funding: “I’m really anti-VC at the end of the day. What people don’t realize is that adding that money adds tremendous pressure, and you just bought yourself a boss. Getting someone to write a check in my opinion is the worst day of your life because they will own your ass, tell you what you can and can’t do, and you will be miserable.”

Lastly, he emphasizes the importance of a lean team: “Staying super lean keeps us profitable. Even though we’re going to do $240million, we’re still super lean. Most comparable companies have a couple hundred employees and we have sixty something. We’re not into overstaffing and creating bloat for the company. Building a real, profitable business is always the way to go.”

3. When it comes to your creative team, prioritize quantity over quality (at least initially).

True Classic is known for their sketch comedy video ads across Facebook, Instagram, and YouTube. However, Bartlett cautions against falling victim to the trap of perfecting an ad campaign before launch. “You don’t have infinite time to flush out ideas and make them amazing,” he explains. “You have to put a stake in the ground eventually.”

Rather than investing significant marketing resources into creating the “best” sketch, Bartlett’s team produces several ideas—then lets the audience decide what’s successful. “Ads start on Facebook and then we test into the,” he shares. “If they have a real ROI then we ramp it out – test it out on $2500-$5k and if not profitable we don’t do ad spend. If an ad’s not doing well, it’s gotta go.”

He also notes balancing relevance and humor with the risk of being offensive. “Sometimes it’s a little too edgy, and I’ll have to taper it back.”

4. Get personal with your entire team.

Bartlett considers himself a “very empathetic person,” and recognizes this at times can “keep [him] in the weeds.” “I just care too much about what [my employees] are going through, when really, a lot of my job should be focusing on the business and what’s right for it.”

Neverthless, he isn’t willing to relinquish that human part of himself—and he actually sees it a retention strategy: “I can’t help but care. Maybe it’s the artist in me, in my lack of, you know, you know, cutthroat corporate mentality. But it’s also part of how you retain people and keep great culture, which is over-caring.”

He also believes in being an open book when it comes to answering “hard questions” about company decisions. He reveals that prior to True Classic’s last all-hands meeting, he set up an anonymous forum for employees to ask any question they wanted. “Nothing is off-limits,” he stated. “Why did this person get fired? Why did this injustice happen? That gave so many people comfort and it felt like they were heard. So many people thanked me after.”

Bartlett views this as a strategy for fostering a culture of transparency and trust. “As a leader, you’ve gotta stand on the front line and not be afraid to answer the difficult question.”