S2E02: Before Clay Was a Unicorn: The First Check, the Thesis, and the Long Game - Andre Charoo, Maple VC

Apr 22, 2025

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.

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ANECDOTE

Andre's Operator-to-VC Journey

Andre Charoo realized he viewed himself as a VC while hopping between startups as an operator.
His investing style builds on helping founders early and believing in them before others do.

INSIGHT

Backing Overlooked Canadian Talent

Canadian founders are overlooked and underestimated at early stages despite world-class education.
Backing Canadian expats offers a strong edge in venture investing and high probability of success.

INSIGHT

Why Canadians Are Alpha Founders

Canadians combine Ivy-level education, immigrant grit, and ambition, creating strong entrepreneurial DNA.
This mix drives their determination to succeed and often pushes them to move to bigger markets for ambition alignment.

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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