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How These Founders Turned a YouTube Side Hustle Into a $75 Million Empire | Entrepreneur

by Brand Post
March 28, 2025
in Business
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How These Founders Turned a YouTube Side Hustle Into a  Million Empire | Entrepreneur
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Opinions expressed by Entrepreneur contributors are their own.

A few years ago, Collin Castellaw was an art teacher earning just $25,000 a year when he decided to start making YouTube videos. Today, alongside his business partner Deron Guidrey, he leads PlayersTV — the first athlete and fan-owned sports and lifestyle TV network with a pre-money valuation of $75 million.

“We’re not from traditional TV or legacy media backgrounds, and I think that’s what sets us apart,” Castellaw says. “It allows us to think differently, move quickly like a startup, and focus on where the industry is heading, not where it’s been.”

Guidrey first discovered Castellaw through Shot Mechanics, his YouTube training channel with over a million subscribers. At the time, Guidery was working in marketing with professional athletes and saw an opportunity to collaborate.

“He connected me with a few pros and asked who was handling my business monetization,” Castellaw recalls. “I told him no one—I was just relying on occasional sponsorships.”

Recognizing the potential, Guidrey offered to take over, putting Castellaw on a modest $2,000 monthly retainer. It wasn’t long before Castellaw voiced concerns, but Guidrey remained confident that bigger deals were on the horizon.

Things shifted when Guidrey noticed the rise of first-person athlete content on platforms like The Players’ Tribune and Uninterrupted.

“I recognized a problem,” Guidrey says. “Athletes were creating production companies, but they had no distribution.”

Related: How This Entrepreneur Turned Athlete Podcasts Into a $25 Million Machine

He envisioned a dedicated channel that showcased the athlete lifestyle beyond the game, featuring cooking shows, reality series, and content that humanized players beyond their uniforms. He reached out to Castellaw, proposing a partnership that combined his marketing and talent strategy expertise with Castellaw’s skills in digital promotions and content production.

“I took a page from Jay-Z’s blueprint when he launched Tidal, bringing artists together to create their own music streaming platform,” Guidrey says. “I applied the same concept to athletes—a platform owned by them, for them.” And thus, PlayersTV was born.

Image credit: PlayersTV

Built by athletes. Powered by fans

PlayersTV is the only athlete- and fan-owned media network, boasting 3,000 hours of licensed and original content. It has distribution deals with major platforms like DIRECTV, FuboTV, YouTube TV, and Fire TV, and it is soon launching its own direct-to-consumer streaming service. Seems like investors liked the Jay-Z line.

“We’re not just a production company creating IP,” Castellaw says. “We focus on guaranteeing 10 to 20 million eyeballs on content. That’s the biggest unlock no one in this space has achieved at our level.”

Much of PlayersTV’s success can be attributed to the groundwork the duo laid before the launch.

“We looked at the problem first,” Guidrey says. “Let’s say you have 40 athletes that want to create content—well, there aren’t enough buyers to host it!”

The goal is for PlayersTV to become the go-to platform for creative athletes seeking distribution, alleviating the pressure on agencies to secure deals with more selective networks.

“Cartoons have Cartoon Network, anime has Crunchyroll, and now, this content has a home too,” Castellaw says.

He points to the limited availability of sports content on major platforms. “If you look at places like Netflix, there’s only a handful of sports content every year,” he explains. “We always say, where there’s fragmentation, there’s an opportunity for aggregation.”

Related: She Saved a Sweet Company and Grew It to $20 Million a Year. But She Never Liked Its Name — Decades Later, It’s Getting a Makeover.

From spectators to shareholders

One of PlayersTV’s most unique features is the Fan Ownership Initiative, allowing sports fans to buy small shares in the company in exchange for perks like exclusive events, and, of course, the bragging rights of owning an athlete media company.

This initiative raised over $3 million from 2,200+ “fan owners,” making PlayersTV the first-ever athlete- and fan-owned media company.

For Castellaw, the philosophy behind the initiative boils down to a simple adage: If you want to go fast, go alone. If you want to go far, go together.

“When an investor questions our valuation or market traction, we point to our fan shareholders as proof of concept,” he says. “It’s a direct endorsement from the very audience we’re targeting for content distribution.”

“By putting athletes and fans first, we position ourselves to attract investors on our own terms,” Guidrey adds. “The equity model with fans resonated deeply with the athletes, and it even empowered us to make our first acquisition—a company bought with the support of our athlete and fan shareholders. How cool is that?”

Guidrey and Castellaw brought their vision to life by combining their unique skills, identifying key problems, and staying true to their core values. While they still have a long way to go, Guidrey wants the company to become the first publicly traded athlete-owned IPO.

“Everything we do is driven by the desire to create lasting impact, not just chase money,” Guidrey says. “We may not be big Hollywood names, but we want our story to inspire other founders like us.”



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Tags: Business PlansCollaborationEmpireentrepreneurFoundersFundraisingGrowing a BusinesshustleinnovationMedia CompaniesMedia CoverageMillionSideSide HustleSportsSportsRelated BusinessesStarting a BusinessSuccess StrategiesTurnedYouTube

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