This Sports Lesson Platform Is Catching Fire With Gen Z & Retirees

TeachMe.To is streamlining sports lessons for users while giving local coaches a way to grow a side hustle or ditch the 9-to-5 grind entirely

The days of booking sports lessons through outdated websites and endless voicemail tag may finally be numbered. That’s the vision behind TeachMe.To, a startup making it as easy to book a sports lesson as it is to order takeout or hail a ride.

“What if it were actually easy to find and book a teacher?” said Tyler Maloney, TeachMe.To CEO and head of product. “How many more people would try something new if we removed the friction?”

It was a pain point Maloney knew all too well. He wanted to learn how to kitesurf, but the wind was quickly taken out of his sails by how outdated the experience was. The user experience felt frozen in time: a handful of instructors, no reviews, clunky websites and payment by phone.

“I started looking into other types of lessons and realized the whole industry looked like this,” Maloney recalled. “That’s when the idea stuck.”

That gap sparked the creation of TeachMe.To, a mobile-first marketplace that connects aspiring learners with local coaches across dozens of activities such as pickleball, golf, tennis, surfing, boxing, basketball, yoga and more. Lessons can be booked, scheduled, paid for and reviewed in-app, with tools and performance feedback layered in to keep students progressing. To make the leap even easier, TeachMe.To offers the first lesson free of charge.

It also offers an alternative to traditional summer sports camps, allowing small groups to book private instruction at an affordable rate, on their own schedule and turf. For many families, the flexibility makes personalized coaching a more appealing option than crowded camps or rigid programs.

And nowhere is that demand more obvious than in the rise of one wildly popular sport. “Gen Z is obsessed with pickleball,” Maloney said, noting that other top categories include tennis, golf, basketball, guitar, singing and piano.

As the company grows, so does its user base and range, giving Maloney a front-row seat to emerging trends among active consumers.

“We’re seeing significant growth across three key segments: adults picking up new hobbies, parents booking for kids, and increasingly, seniors,” Maloney said. “Baby boomers are retiring, and they’re a curious, active generation—they’re signing up to learn golf, music and even pickleball.”

TeachMe.To has also become an unexpected home for more unconventional interests, demonstrating the platform’s flexibility and broadening appeal.

“Recent bookings include skateboarding, billiards and even team roping,” Maloney said. “We never expected to be selling lessons in team roping or billiards, but here we are.”

TeachMe.To is also investing in tools to keep students coming back.

“Our big focus right now is what happens after you meet your coach,”Maloney said. “We’ve gotten good at helping people book lessons, but now we’re building tools that help students stick with it—practice regularly, improve faster and stay motivated.”

Part of that push includes integrating AI. “Coaches can use AI tools after each lesson—for example, they can speak with an AI assistant that helps summarize the session and create personalized homework for the student,” Maloney said. “It saves time and adds structure that students really appreciate.”

There’s also advanced swing analysis technology, Maloney said, allowing coaches to give more structured feedback.

“Coaches can record a video of a student, mock it up, slow it down, provide feedback, and then send it to the student to review,” he said.

For coaches, the model offers a new revenue stream with fewer headaches. Matthew Dean, a golf instructor on the platform, said he was initially surprised by how effectively it matched him with students across skill levels. It’s also helped him offload the administrative grind.

“The hardest part of coaching is often the marketing and logistics side of things,” Dean said. “TeachMe.To promotes my page and services, facilitates bookings, processes payment, intuitively schedules lessons and the platform handles messaging, reviews and performance analytics. It allows me to focus on coaching, instead of all the other stuff.”

It’s not just coaches who benefit. Dean said students often praise the platform’s simplicity and organization.

“The overwhelming positive app feedback I receive from my students is the ease of use with the app,” he said. “The ability to schedule and have all of their messaging and lesson info in a space separate from the inbox or professional careers is key.”