Every month we feature members from the Everything Marketplaces community to help highlight their story, marketplace journey, and share more about what's ahead. In this member feature we highlight Tyler Maloney, Co-founder & CEO of TeachMe.To. TeachMe.To is a marketplace for booking 1:1 lessons for sports like golf, tennis, pickleball, and more.
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So what’s your background briefly and what led to the idea for starting TeachMe.To?

TeachMe.To is my third company, and I’ve been building consumer startups for over a decade. I’ve been lucky enough to be backed by some of the world’s best investors and raised a total of around $25m in VC funding.

The inspiration for TeachMe.To came from my own experience in 2021 while living in the Bay Area. I wanted to learn how to kiteboard, so I started looking up instructors on Google. I found a few websites that offered lessons, but it was really hard to book. They had no pricing information, no reviews and no way to buy lessons online. The whole process was too cumbersome, so I went on with my day, without booking. I’m a pretty average consumer (read: lazy) so I’m sure a lot of other people got stuck in the same place.

It struck me that these instructors have an incredible skill to share with the world. They love to kiteboard and share that passion with others, but they're not the best self-promoters. As a result, countless people will miss the opportunity to learn from them. And frankly that made me sad.

After I realized there was a major disconnect, I started to look more closely at lessons for other skills and found this to be a common theme for the entire industry.

What were some of the first steps you took to start TeachMe.To? What were some of the biggest challenges that you faced?‍‍‍

I started to validate the idea by socializing it with friends. You have to be careful when you do this because people like to be nice. When someone doesn’t really want your idea, they give you a vague answer about how someone, somewhere would love this. They tap into the theoretical part of their brain. In contrast, when they do want your idea, they tap into their memory. I’d say 6 out of every 10 people said something like "Oh my god, just last week I was looking for tennis lessons for me and my husband and I just couldn’t find anyone I liked" and their eyes would light up.

After that, we began to run some painted-door marketing tests: making a fake website, running facebook ads to drive traffic to the website, and measuring click through rates. It became clear that people were dying for an easy-to-use online booking experience for things they’ve always wanted to learn. So we started to build the team, recruit our first coaches, figure out our GTM channels and refine our unit economics. Since then, it’s really been about solving one user problem at a time.
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What's the problem that you’re solving for and how has building TeachMe.To as a marketplace proven to be a great solution?‍

As a marketplace, we’re really solving two problems for two distinct groups.

For our students, we lower the barrier to learn something new. Almost everyone I talk to has something on their bucket list they want to learn, but unless they’re really tied into an ecosystem (like a country club) they don’t know where to start. That’s a really serious problem, both for the individual and for our society. A lot of these skills, like golf and tennis, are inaccessible to beginners and as a result, they become very exclusive. I think that’s silly. It shouldn’t be that hard to break into a new sport. And I think it’s a positive change for the world if we can make "elitist skills" easier and more accessible to the everyday person who wants to get started and doesn’t know where to begin.

For our coaches, we make sharing (and monetizing!) your passion so much easier. Everyone has something to share. People have these crazy and diverse talents of every type. The problem is that 99% of our intellectual capital is locked up because of how difficult it is to start a business and share your knowledge with the world. Airbnb and Uber realized there were beds and cars sitting empty all over the world that could be valuable; we believe there are skills and talents locked up in people’s minds that can be really valuable if only we can make that knowledge easy to share. Our mission is to unlock all of that intellectual capital. The way we do that is by making it really easy for anyone to start a lesson business. Unlike our competitors, at TeachMe.to we handle all the "business stuff" so that you can just show up and share your passion with the world. And by everything, I really mean everything…scheduling, insurance, taxes, customer service, sales, marketing…we do it all for our coaches.

If we are successful at scaling the business, both sharing and finding your passion will become a hell of a lot easier. And I think that’s really important for the human experience. With the coming AI revolution, there’s a lot of anxiety around "our place" in the world, and I think TeachMe.To can be part of making the future better than the past.
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How have you approached solving the cold start problem with TeachMe.To as a marketplace?‍

Reaching "minimum viable liquidity" was our primary focus. Unlike Uber, which needed hundreds of cars, we only needed a few flexible coaches willing to travel and accommodate various schedules. This flexibility reduced the cold start problem and helped us establish a foothold in the market. We formed very close relationships with early service providers, overpaying them, and leveraging that to build a high quality early experience in just one market at a time. I think it’d be a lot harder to enter the market now because we’ve introduced a better solution with network effects that’s started to take hold.
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What's been the biggest learning so far?

We’ve learned there’s a vast pool of untapped expertise out there. We’ve helped thousands monetize their passions, with some even transitioning away from jobs they don't like to full-time coaching. It’s incredibly rewarding to support these individuals. As those NCAA commercials used to say, "98% of student-athletes will be going pro in something other than sports." We're here to help the 98%.
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You’ve raised from some awesome investors, so what has the early fundraising journey been like? Are there any initial learnings you can share for other founders?

We’re fortunate to have backing from tech luminaries like Sam Altman, Deb Liu, Gokul Rajaram, and Casey Winters. My advice is to listen to your investors, but always trust your gut. They offer valuable insights and a wealth of knowledge, but as a founder, you have the most comprehensive view of your data and vision. So listen to them, consider their ideas fully, and then trust your instincts.
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How big does TeachMe.To get and what’s needed to get there?‍

We aim to capture 30-40% of the $15 billion U.S. private lessons market. But, we also believe we can expand the market by converting non-consumers into consumers. From my own experience with kiteboarding, the right marketplace would have turned a non-consumer (me) into a consumer. Our goal is to grow the pie, turning a $15B market into a $50B or $100B market.

What’s exciting and ahead for TeachMe.To that you can share with us?‍

We’re enhancing our app to support the entire learning journey, not just finding a coach. In the next year or two, our app will evolve to offer a suite of tools that help students progress from beginners to experts, resembling platforms like Duolingo more than mere scheduling software. We want TeachMe.To to be a comprehensive, end-to-end experience for learning sports, music and the arts.

We also just shared about our $5m funding round, which you can read about here!

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Connect with Tyler in the Everything Marketplaces community. ‍‍