Three failures into the lesson that stuck.
In 2021, Tyler Maloney was living in San Francisco, eyeing the kiteboarders off Crissy Field, and doing what everyone does when they want to learn something new - Googling around. What he found was a mess: instructors with no websites, websites with no prices, prices with no availability. The market existed. The infrastructure did not.
That friction was the blueprint. Not because kiteboarding is a billion-dollar category, but because it was everywhere - golf, tennis, pickleball, violin, painting, boxing - any skill you wanted to learn from a real human being in your neighborhood involved the same broken loop: search, give up, search again, call a number that goes to voicemail.
TeachMe.To launched in 2022 to replace that loop. The pitch was direct: book a vetted local coach in under five minutes, get your first lesson free, and cancel anytime. In year one, the platform delivered two lessons a day. By 2024, it was over 200. By 2025, lessons were up 46% year over year. That's not viral growth - that's compounding trust.
Maloney's path to this had a few detours. He graduated from NC State in 2014 as a Park Scholar with a degree in materials science and engineering - a choice sparked by a gap year working at a wildlife rehabilitation center in South Africa. The science was real, but the pull toward building things was stronger.
The shared middle school background between Tyler and Sam Altman reportedly helped land the first meeting. TeachMe.To's seed deck led with the emotion of being a beginner - not the market size. Altman invested. Then Deb Liu. Then Gokul Rajaram. The problem-first pitch worked exactly as Maloney had predicted: "If you don't get those first two-ish slides right, it's over."
"Entrepreneurship is like playing poker. You may not win every hand, but if you play long enough you can tip the scales in your favor."Tyler Maloney — NC State Park Scholarships Interview, 2023
Nail polish that changes color on contact with common date-rape drugs. Built as a senior design project, it went viral globally, earned multiple patents, and raised serious capital before ultimately shutting down. Failure that looked like a lesson - because it was.
$12M raisedA website and mobile app to save and organize videos from across the internet. Grew to over 200,000 users. Pre-algorithm, post-YouTube chaos - the right problem at the slightly wrong time. A proving ground for consumer product intuitions.
200K+ usersPrivate coaching marketplace across sports, music, and arts. Connects students with vetted local coaches. First lesson free. 250+ cities. The Airbnb for skills - but with a 4.9-star average and Sam Altman's backing. Still accelerating.
$10.5M raised"A lot of these skills like country club sports are inaccessible to beginners. I think there's a lot of big social value in making those 'elitist skills' easier for everyday people."Tyler Maloney — GrepBeat Interview, July 2024
Maloney has a rule: every week, he and his entire team book and take lessons through TeachMe.To. Not as a performance review. As a sanity check. "Every week I eat dog food and I make my team do it too," he wrote on LinkedIn. Product intuition is not a meeting. It's a pickleball lesson with a stranger on a Tuesday.
He publicly scores his team's metrics. Investors get the unfiltered version: what's working, what isn't, what changed. "We're pretty diligent about what's going well, what's not going well." Founders who hide the bad numbers from investors are usually hiding them from themselves too.
The pitch philosophy is pure economy: lead with the problem, make the investor feel it before they see the numbers. "If you don't get those first two-ish slides right, it's over." He's raised money eight times across three companies. The sequence hasn't changed.
"Listen to your investors, but always trust your gut - you have the most comprehensive view of your data and vision."Tyler Maloney
"Retention is one of the biggest metrics on both sides that we look at."Tyler Maloney — Globy Podcast
"We believe that our team in Brazil is as good, if not better than a lot of American coders."Tyler Maloney — On building distributed teams
Spent a year at a wildlife rehab center in South Africa during college, which changed his major.
His first company made nail polish that detects date-rape drugs. It went viral before going under.
The entire TeachMe.To empire started because one man could not book a kiteboarding lesson in 2021.
He runs a San Francisco startup from Philadelphia - because the product works from anywhere.
He's a Park Scholar - one of NC State's most selective merit scholarships.
Sam Altman and Tyler Maloney went to the same middle school. That conversation turned into a check.
The private lessons market is a $15 billion category in the US alone. Maloney's thesis is that by removing friction - and capturing the people who never booked because it was too hard - TeachMe.To can expand the market itself, not just take share from it.
The target: a Duolingo-scale platform for in-person human learning. Not video courses. Not AI tutors. Neighborhood coaches who know your name, adjust to your pace, and show up on Saturday morning. The coaches get scheduling, insurance, taxes, and customer service handled. The students get a 4.9-star experience from lesson one.
The big bet is that physical, personal instruction is one of the few categories that doesn't get disrupted by software - it gets amplified by it.