Information on the Target

TeachMe.To is revolutionizing the landscape of private, in-person instruction, particularly focusing on sports such as golf, tennis, and pickleball. The company addresses an established market worth approximately $70 billion in the U.S., which has historically been fragmented and inefficient. By transforming how consumers find, book, and engage with local coaches, TeachMe.To is creating a streamlined experience that enhances user engagement and satisfaction.

The platform uniquely combines elements of a user-friendly marketplace reminiscent of Airbnb, with engaging features akin to gamification, similar to Duolingo. The app facilitates an easy interface for students to connect with vetted coaches while offering tools for progression tracking, rewards, and lesson recaps, which not only retain users but also elevate their learning experiences.

Industry Overview in the Target’s Specific Country

The U.S. private lesson market has seen significant shifts, particularly following the COVID-19 pandemic, which has led to a resurgence in demand for in-person activities and experiential learning. As individuals seek a counterbalance to digital engagement, the desire for real-world interactions has surged, marking a significant trend in consumer behavior.

This consumer trend has been termed “social rewilding,” as highlighted in Accenture’s 2025 Consumer Trends Report, which identifies a move back to physical activities and human connections. Notably, 42% of respondents reported that their most enjoyable recent experience involved a physical activity, indicating a strong pivot towards the experience economy.

Despite this demand, the private lesson industry has remained highly fragmented, making it difficult for consumers to navigate and find reliable services. The current providers primarily serve as lead-generation platforms, lacking comprehensive features that improve retention and the overall learning experience. This fragmentation is particularly pronounced in the $15 billion sports instruction segment, where existing platforms have failed to deliver meaningful engagement.

TeachMe.To is stepping into this gap by establishing itself as a trusted brand in the market, utilizing its focus on specific high-demand sports to create depth and quality in its offerings. In just three years, TeachMe.To has become the leading global provider of pickleball lessons, signaling its effectiveness in capturing market share within this fragmented industry.

The Rationale Behind the Deal

The investment in TeachMe.To aligns perfectly with the rising consumer appetite for in-person, experiential learning environments amid the growing preference for real-world interactions. The platform’s innovative approach to the traditional model of private lessons addresses key pain points, positioning it uniquely within a burgeoning market.

By intersecting technological efficiency with community-driven engagement, TeachMe.To is creating a blueprint for future growth. Documented interest in private instruction—fueled by the ongoing social rewilding trend—illustrates the firm basis for this investment, promising both a rewarding consumer journey and profitable returns for stakeholders.

Information About the Investor

The investment round is being led by reputable venture capital firms, including Bling Capital and 1984 Ventures, known for their focus on innovative startup ecosystems. The leaders have extensive experience in collaborating with emerging companies in the technology and education sectors, providing not just capital, but also strategic guidance to fuel growth.

Partnering with TeachMe.To signifies an intentional choice to support businesses that are committed to redefining consumer experiences. The investors recognize Tyler Maloney, TeachMe.To's CEO, as a proven leader with an impressive track record in building successful startups and understanding market dynamics, empowering their confidence in this venture.

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In my expert opinion, TeachMe.To represents a compelling investment opportunity, capitalizing on the significant consumer shift towards experiential learning. The company is well-positioned to leverage its unique market insights and innovative model to drive growth and engagement in a fragmented landscape. This strategic focus not only enhances the customer experience but also aligns perfectly with current trends towards wellness and in-person activities.

Moreover, the comprehensive service offerings for coaches reflect a thoughtful approach to improving the overall teaching landscape, ensuring satisfaction for both instructors and students. The gamified elements introduced by TeachMe.To are likely to promote increased engagement and retention—critical components for sustained success within this industry.

Finally, given the ongoing consumer demand for in-person experiences and the notable shortcomings of existing players in the market, TeachMe.To is ideally positioned to capture market share and is set on a path to redefine how private instruction is delivered. The investment in TeachMe.To is not just timely but also strategically sound, providing a promising avenue for future returns.

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