Now active in 250+ U.S. cities, TeachMe.To has emerged as the go-to marketplace linking learners with instructors in sports, fitness and hobbies
TeachMe.To, a San Diego startup that connects students with local instructors for lessons in pickleball, golf, yoga, tennis, soccer and more and counts Sam Altman among its backers, has raised $3 million in a seed extension round.
Interplay led the round with participation from Bling Capital and 1984 Ventures, which follows strong metrics: TeachMe.To lessons are up 46% year-over-year in the first half of 2025.
The marketplace, live in more than 250 U.S. cities, now has 5,000 active instructors, 30,000 students and nearly 100,000 lessons completed. TeachMe.To says the capital will help advance technology and app development, including additional AI features for learning enhancement.
And while AI may power much of TeachMe.To’s growth, founder and CEO Tyler Maloney said the real focus remains on people, with technology giving the company an extra lift.
“We’re in the business of facilitating human-to-human interaction,” Maloney said. “But we’ve fully embraced the benefits and efficiencies that AI has to offer our company.”
The platform uses AI for personalized lesson plans, auto-generated analytics, predictive overviews, intuitive scheduling and swing analysis tools, adding value for both coaches and learners while helping TeachMe.To scale without a larger team.
“In part because of our adoption of AI, the business is approaching profitability earlier than anticipated, so we were able to keep the raise small and avoid unnecessary dilution,” Maloney said.
With the rise of marketplaces across everything from pet care to gig work, Interplay partner Michael Rogers said TeachMe.To was the natural next step in services across fitness and hobbies.
Beyond its growth metrics, TeachMe.To has tapped into clear consumer trends. Maloney previously told Athletech News that Gen Z is driving demand for pickleball, while baby boomers are flocking to golf, music and other activities in retirement.
“The business made too much sense for us not to get excited about it,” Rogers said. “If you need pet care, you go to Rover to find a walker; if you have a task or odd job that you need done, there’s a marketplace or app for that, but what about if you want to learn a new sport or you want to finally learn to play the guitar? TeachMe.To not only makes it easy to find, browse and book a local lesson, their platform actually adds significant value to the learning and coaching experience.”
