Meet Tyler Maloney, CEO at TeachMe.To:

Tyler Maloney is the CEO and driving force behind TeachMe.To, a groundbreaking platform transforming the way people learn new skills. From sports to music, the company connects learners with expert coaches across the U.S., offering personalized lessons at scale. Under Tyler’s leadership, TeachMe.To has experienced phenomenal 10x growth in just a year, delivering hundreds of lessons daily across more than 100 cities. The company recently secured $5 million in seed funding from notable investors such as Sam Altman and Blink Capital, setting the stage for continued innovation in skill acquisition. Tyler’s leadership is paving the way for how people will learn, remotely or in person, while revolutionizing global-first hiring and employment practices.

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Quick Read: Tyler Maloney, CEO at TeachMe.To, Interview Highlight

Unveiling the Journey of TeachMeTo: A Conversation with Tyler Maloney

In our latest episode of Default Global, I had the privilege to sit down with Tyler Maloney, the CEO of TeachMeTo, a company disrupting the learning landscape by offering lessons across various skill sets. Our discussion unearthed a treasure trove of insights into the metrics driving TeachMeTo’s impressive growth, fundraising intricacies, and strategic decisions shaping its global team.

Key Metrics: A Balancing Act

I kicked off our conversation by asking Tyler about the key metrics behind TeachMeTo’s 10x growth leap. He shared that the focus is on demand-side retention, ensuring students return for more lessons, and supply-side retention, maintaining coach engagement.

Tyler emphasized:

“Retention is one of the biggest metrics on both sides that we look at”

His approach underlines the necessity of balancing both ends of a marketplace—ensuring a seamless experience for both learners and instructors.

Raising Funds: A Strategic Approach

As we delved into their fundraising journey, Tyler shared how each round differed, emphasizing the impact of being “on trend” versus “off trend” in securing investments. He advised founders to understand their market standing, noting,

“If you’re building AI today, you can often raise on an idea and excitement… But if you’re off trend, you’ll be met with skepticism.”

TeachMeTo’s recent $5 million seed round was closed by executing a tight fundraising process, engaging potential investors simultaneously to foster urgency.

Marketplace Fundraising Challenges

Diving into fundraising specifics for marketplace models, Tyler noted the daunting task of overcoming investor skepticism, which stems from past investments in unsuccessful marketplace ventures.

He explained:

“VCs are pattern matchers,”

TeachMeTo’s success in raising capital, particularly from renowned figures like Sam Altman, stemmed from showcasing strong traction and narrating a compelling story despite current market challenges.

Nurturing Investor Relationships

I was curious about Tyler’s approach to maintaining investor relationships. He shared that his perspective evolved over time, transitioning from seeing investors as bosses to advisors.

Tyler stressed the importance of honesty:

“We’re pretty diligent about…what’s going well, what’s not going well.”

This transparency builds trust, ensuring investors remain aligned with the company’s progress.

Crafting an Effective Pitch

On crafting pitches to high-profile investors, Tyler highlighted the need to capture hearts first by articulating the problem before unveiling the solution.

He cautioned against skipping this step, stressing:

“If you don’t get those first two-ish slides right, it’s over before it’s even started.”

Timing in Fundraising

Timing is crucial, and Tyler advised founders to raise funds proactively, not reactively. He described fundraising as a “necessary evil” and emphasized the need to raise “six months in advance” of needing capital, ensuring sufficient runway and traction are presented to potential investors.

The Distributed Team Advantage

TeachMeTo’s distributed team, spanning Brazil, the Philippines, Canada, and the US, was a point of curiosity. Tyler acknowledged potential investor concerns but underscored the competitive advantages, such as accessing diverse talent pools.

“We believe that our team in Brazil is as good, if not better than a lot of American coders,”

Tyler stated, highlighting the strategic value of international hiring.

In conclusion, my conversation with Tyler Maloney provided a profound look into the dynamic world of marketplace startups, from fundraising nuances to the strategic orchestration of an international team. His insights serve as invaluable guidance for founders navigating similar paths, reinforcing the importance of strategic planning, transparent communication, and adaptive leadership in the startup ecosystem.