S2E02: Before Clay Was a Unicorn: The First Check, the Thesis, and the Long Game - Andre Charoo, Maple VC
Apr 22, 2025
auto_awesome
Andre Charoo, an investor at Maple VC with a rich background as an operator at Uber, highlights the overlooked successes of Canadian founders. He passionately discusses why these entrepreneurs are often undervalued yet highly ambitious. Andre shares his long-term investment philosophy, illustrated by the journey of unicorn Clay, which took over seven years to flourish. He also emphasizes the importance of building durable companies and maintaining competitive advantages, or moats, even in today's AI-dominated landscape.
Andre Charoo highlights the remarkable potential of Canadian founders, especially immigrants, who often go unrecognized in the global startup ecosystem.
The journey from operator to venture capital investor allowed Andre to realize the importance of supporting founders throughout their growth endeavors.
Emphasizing the importance of patience, Andre illustrates how long-term investment in startups, like Clay, can yield extraordinary results after several years.
Deep dives
Transitioning from Operator to Investor
The speaker discusses the evolution of his career from being an operator in startups to becoming a venture capital investor. Initially joining several seed-stage companies, including Uber, he reflects on how his early experiences shaped his investment perspective. Over the years, feedback from his network indicated that his frequent changes in company affiliation suggested a natural inclination towards venture capital. This realization led him to understand that his role as an investor was an extension of his prior journey, where he continuously supported founders in their growth endeavors.
The Significance of Canadian Talent
A key insight revolves around the remarkable potential of Canadian founders who often go unrecognized in the global startup ecosystem. The speaker identifies a pattern where many successful companies, such as Uber and Slack, were founded by individuals with Canadian roots. This observation underscores the undervaluation of talent emerging from Canadian educational institutions, which he believes provide Ivy League-quality education. By leveraging his own connections to this network of talented Canadians, he aims to support and uplift their entrepreneurial journeys through his investment fund, Maple.
Defining the Investment Thesis
The speaker elaborates on the foundational principles behind his investment thesis, which began taking shape in 2016. He emphasizes the importance of believing in founders and their ideas before the broader market recognizes their potential. His focus is primarily on seed-stage companies led by Canadian expats, as he believes these entrepreneurs possess unique insights and capabilities that often get overlooked. By positioning himself as the first believer in their vision, he aims to provide them with the necessary support to navigate the competitive landscape of venture capital.
Identifying Opportunities in AI
As the conversation progresses, the speaker reflects on the current landscape of investment opportunities, particularly in the realm of artificial intelligence. He expresses optimism that we are only beginning to scratch the surface of potential AI applications, noting that current exuberance might evoke memories of earlier tech booms. He believes that the transformative potential of AI will open new avenues for innovation, allowing startups to operate with a leaner structure. By focusing on unique insights and a deep understanding of nascent technologies, he aims to identify and back the next generation of groundbreaking companies.
The Role of Founders in Building Ventures
The speaker emphasizes the varying characteristics that different types of founders bring to the table, categorizing them as inventors, builders, and operators. He argues that successful companies typically have a combination of these archetypes to navigate the different stages of their journey from inception to maturity. He highlights that while the influence of AI might reduce the number of people needed in some roles, the need for strategic thinking and creativity remains essential. Ultimately, he views the evolving landscape of entrepreneurship as an opportunity to reaffirm the importance of human insight and collaboration in driving meaningful change.
Canadians have been the lifeblood behind some of the biggest unicorn startups of the past few years (think Open AI, Uber, Slack, Instacart, Notion, Databricks, CloudFlare, Roblox, Ethereum, Moderna Health, and Clay to name a few), and yet no one talks about them, except for Andre Charoo. And he’s not just talking – he’s putting his money behind Canadian founders through his fund, Maple VC.
Andre shares why he thinks Canadian founders are always a strong bet (and bonus points if they’re immigrants, too), what it’s like to wait over 7 years to see a pre-seed investment materialize (in this case, recent unicorn Clay), and how he thinks about moats in the AI age (and why they still matter).
Maple VC writes $500k – $1.5 million industry-agnostic checks into pre-seed and seed stage companies with roots from Canada to Korea to Harvard.
Highlights
Even long after he left Uber and Hired, Andre never lost his go-to-market spirit and he’s carried it with him as he’s moved from operator to VC.
Andre’s investing framework can best be described as Canadian roots with global reach. He’s been working hard to give Canadian founders their due and show their world that they are some of the most ambitious people out there.
Clay, a unicorn in the Maple VC portfolio, is a testament to persistence and patience. Andre urges investors to remember they’re playing the long game – waiting for results that may not materialize for nearly a decade.
It’s all about building durable companies, and the 7 Powers by Hamilton Helmer still holds true. Andre stresses that defensibility and success come from strategic insight, execution, and taste—not just code.
While AI is changing the way companies form and scale, Andre still believes in this undefeated combo for founders: inventors, builders, and operators.
(00:00) - Andre Charoo, Maple VC - Before Clay Was a Unicorn: The First Check, the Thesis, and the Long Game
(01:40) - Andre’s journey from operator to investor
(06:56) - Why Andre will always bet on Candian expats
(22:46) - Andre’s check size and how he manages Maple VC
(33:38) - The 7-year story of the unicorn, Clay
(42:14) - Where Andre thinks AI stands and where it might be going
(49:17) - Moats still matter in the AI era
(01:03:02) - Andre's take on the inventor-builder-operator trifecta
Remember Everything You Learn from Podcasts
Save insights instantly, chat with episodes, and build lasting knowledge - all powered by AI.
