Our Investment in TeachMe.To
Written by Caroline Elliott and Marina Perez-Llorca
Over the past several years, the world has undergone a profound shift in how people live, work, and connect. The COVID-19 pandemic and the widespread adoption of remote work accelerated the digitization of nearly every aspect of life. At the same time, social media and the digital economy have driven people deeper into screen-based interactions, fundamentally altering how individuals spend their time and engage with the world. This shift has sparked a powerful countertrend: a growing consumer desire to reconnect with the physical world through real, in-person experiences.
This resurgence of the “experience economy” is being fueled by widespread appetite for activities that are social, skill-building, and wellness-oriented. People are seeking opportunities to be present, learn new things, and form meaningful connections — not through apps and screens, but in parks, studios, courts, and clubs. Accenture’s 2025 Consumer Trends Report named “social rewilding” — the shift of free time back to real-world activities and human connections — as one of the top 5 most influential consumer trends. 42% of survey respondents said their most enjoyable experience the previous week was a physical activity.
Many people today seek to learn a new skill through private lessons. The total addressable market in the U.S. for private, in-person lessons across music, sports, and other hobbies is estimated at $70B. Despite the size of the opportunity, the industry has historically been highly fragmented. The process of booking a private lesson remains outdated, scattered, and opaque. Consumers are forced to scour the web, ask friends for referrals, make phone calls, leave voicemails, and often commit to instructors without reviews, transparent pricing, or easy scheduling. This fragmentation is evident in the $15B sports segment, where the three largest digital incumbents — Lessons.com, MyTennisLessons, and CoachUp — operate. While these platforms serve as entry points for coach discovery, their value proposition is shallow: they function primarily as lead-generation tools without offering meaningful business management or student engagement features. As a result, retention is low, quality is variable, and the customer experience is inconsistent.
TeachMe.To is reinventing the way people discover and engage with private, in-person instruction, starting with sports. By focusing on categories like golf, tennis and pickleball — high-demand verticals where legacy offerings have failed to deliver — TeachMe.To is able to build meaningful density between coaches and students, refine category-specific features, and establish itself as the trusted brand in a fragmented market. The company’s platform combines the consumer-friendly marketplace model of Airbnb with the gamified learning experience of Duolingo. For students, TeachMe.To delivers a seamless way to find, book, and engage with vetted local coaches. Its app introduces gamified features — lesson streaks, rewards, progress tracking — that encourage retention and deepen the learning journey. For coaches, TeachMe.To provides a true “business-in-a-box”: marketing, scheduling, payments, insurance, tax filing, and even AI-powered lesson recaps and video analysis tools. In just three years, TeachMe.To has emerged as the #1 global provider of pickleball lessons and is rapidly gaining ground in golf and tennis — clear evidence that its verticalized approach is transforming the sports instruction market.
TeachMe.To is led by Tyler Maloney, a seasoned entrepreneur with deep experience at the intersection of product, growth, and community. Tyler previously founded Faves, a Gen Z-focused content discovery platform that reached the top 10 on the App Store, is still used by millions, and was backed by Lightspeed, Greycroft, and several Midas List venture capitalists. Before that, he launched Undercover Colors, a consumer biotech company that raised over $12M and garnered national media coverage. Across his ventures, Tyler has demonstrated an exceptional ability to identify emerging trends, design and ship user-loved products, and build scalable, capital-efficient businesses. His experience in both B2C product development and two-sided marketplaces uniquely positions him to lead TeachMe.To.
We are excited to lead TeachMe.To’s $3 million Seed+ round alongside Bling Capital and 1984 Ventures. TeachMe.To is building not just a marketplace, but a new standard for in-person learning — integrated, engaging, and high-retention — and we’re excited to partner with Tyler and the team on the journey ahead.