For Taylor Caby, co-founder and CEO of Establish The Run, the path to building a respected fantasy sports analysis platform began long before the company existed—back when online poker first exploded in popularity.
“I basically fell into online poker when I was in college,” Caby said on the BettingStartups Podcast. “It was around the Chris Moneymaker era… people in college were playing a ton, so it just sort of was like my number one hobby and passion and I ended up turning it into a career.”
Caby spent roughly two decades immersed in real-money gaming across poker, sports betting, and daily fantasy sports at companies including Rush Street Interactive and CardRunners. Those experiences shaped both his approach to risk and his eventual move into entrepreneurship.
Today, Establish The Run operates as a subscription-based content and analytics business focused primarily on fantasy football and player prop betting. Rather than trying to cover every betting market or sport, the company has built its brand around specialization and depth.
“Establish The Run is a content business that delivers really high quality information about fantasy football and some sports betting,” Caby explained, adding the site focuses on player-specific analysis. “We don’t cover who’s gonna win the game, but we do cover how the players are gonna do.”
That focus has helped the company grow steadily. Caby said the business now employs more than 20 full-time staff alongside dozens of part-time contributors producing analysis, projections, and written content.
At the core of the company’s strategy is a simple but demanding principle: quality over coverage.
“If it was just one thing, I would say it’s high quality,” Caby said. That focus means the company sticks to covering what it knows best (currently NFL, NBA, MMA, and PGA) and leaves it at that. He added that the site doesn’t cover baseball, for example. Despite being a popular fantasy sport, Caby said they don’t feel like they have “a unique point of view” that would warrant it. “I think customers definitely appreciate that,” he said.
Unlike many startups, Establish The Run didn’t rely on outside capital in its early days. Caby said the team was able to launch and grow the business largely through internal resources, reflecting his belief that media-driven betting products can often be built without massive upfront investment.
“You can start up a business like ours for next to no money,” he said.
The mindset that guides Caby’s decision-making, both as a bettor and as a founder, comes down to evaluating tradeoffs.
“My framework is just risk and reward,” he said. “What is the risk of whatever I’m going to do… and what’s the reward?”
That same framework has helped Caby transition from professional player to operator. And while the gambling industry continues to evolve with new technologies like AI and automation, his approach remains rooted in the fundamentals.
“I’m thinking about this a lot and I don’t know the right answer,” Caby said when asked about the future of analytics and AI in betting. “I think anybody that says otherwise would be either lying or ignorant.”
On the other hand, Caby insists that while AI may become more and more capable, the value of distribution is not going to change. “Having the ability to reach customers, an audience that cares about you and what you’re saying and trusts you, is again, increasingly hard to get,” he said.
For Establish The Run, the next phase will likely depend on continuing to do what Caby believes the company already does best: focusing relentlessly on quality, and letting that reputation drive growth. But today, the company is profitable and poised to continue growing.
“If the North Star is high quality, really doing great work, I think we’ll be successful.”
