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

04/22/25 • 74 min

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

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

Previous Episode

S2E01: Lessons on AI, PM, and LLMs from founder, investor, and operator Shalin Mantri

You can be a founder. You can be an investor. You can be an operator. Or, you can be Shalin Mantri and be all three. This respected product leader got his start by founding a mobile app startup in the early iPhone days in 2011 and followed it up with product leadership in the early days of Uber, Skip and more recently, Google. He angel invests with $5k – $50k checks as a true first believer, usually in companies where he has a personal connection with the founder.

He shares his tiered angel investment system, where he sees autonomous vehicles going (and not going), his thoughts on AI, how AI might have transformed Uber’s early days, and what he thinks of the rise of multi-billion-dollar, 1-pizza companies.

Highlights

Shalin has a tiered system for evaluating angel deals, and ultimately, determining how much he’s willing to invest.
Uber experienced incredible growth from its founding in 2009 through the 2010s when Shalin came aboard as a product manager. He chats about how he thinks AI would’ve changed Uber’s story if it had been around at the time.
Shalin explains how AI is running a parallel path with autonomous vehicles, especially when it comes to scaling up without losing product integrity. Just like with AVs, the bar is high for reliability, safety, and performance for AI tech.
Recently, the search bar has been less of a source of information and more of a source of frustration. Shalin is focusing on building a solution to improve search, with the help of AI, of course.
Company headcounts are getting smaller, and yet their valuations are getting bigger. Shalin’s not necessarily sold on the 1-company, 1-billion dollar company just yet, but he sees the trendline moving in that direction.
(00:00) - 01 - Shalin/Shaherose A/V
(02:19) - How Shalin evaluates angel deals and deploys checks
(13:20) - Working at Uber during the early(ish) days
(17:59) - Not all growth is good growth
(26:26) - Exploring the interplay between AI and AVs
(34:07) - When the big bet doesn’t lead to the big payoff
(37:42) - Why AI is making it a confusing and exciting time for PMs
(42:51) - What’s wrong with search these days? Is search being rewritten - again?
(46:40) - Scaling companies down to 1 pizza and 1 pizza only
(58:39) - Shalin’s AI angel investments

Next Episode

S2E03: Atoms over bits: Investing in hardware and innovative founders to solve climate challenges - Sundeep Ahuja, Climate Capital

We’ve welcomed investors with unique backgrounds to First Funders before, but Sundeep Ahuja is our first operator-turned-actor-turned-investor.

Sundeep is all in on all things climate tech. He’s backing founders leading the way in cleaning up our water, purifying our air, and keeping our planet the way it should be: livable. Today, his micro fund and syndicate platform Climate Capital, has over 400 climate-focused companies in its portfolio.

Sundeep shares why he thinks real-world, physical tech has the edge over software, how the words we use matter when it comes to addressing climate challenges, and why he’s still optimistic about the future despite current social and political challenges to climate initiatives.

He writes ~$150k checks out of Climate Capital into pre-seed and seed-stage startups addressing emission reductions and climate adaptation.

Highlights:

Sundeep had a winding path to investing, but his passion for the climate has always been there. He talks about how his time at Kiva shaped and expanded his worldview.
We’re heard a lot about software, but Sundeep is firmly in the hardware camp. He’s seeing startups like Copper and Avalo make incredible strides working with physical products – or focusing on atoms over bits, as he says.
The way we talk about issues matters, and Sundeep is seeing the impact of language play out in the climate space. His solution is simple: No vague, moralizing language. Just plainly state what you’re doing to help the environment.
Sundeep has a careful eye on what’s going on regarding the climate and the current administration, but he’s not feeling deterred. He believes there’s still plenty of capital – and plenty of people who believe in the mission – to sustain the headwinds.
Like a true investor, Sundeep has a story about his worst investment and what he learned from it. Mainly, that the importance of due diligence can’t be overstated.
(00:00) - Atoms over bits: Investing in hardware and innovative founders to solve climate challenges - Sundeep Ahuja, Climate Capital
(01:39) - Sundeep’s journey from eBay to Acting to Impact
(02:44) - Finding his purpose at Kiva and focusing on climate
(03:52) - Establishing Silicon Climate and writing his first book
(09:17) - Sundeep’s work founding and scaling up Climate Capital to an 400-company portfolio
(13:45) - Why technical founders and defensible IP are now at the heart of their seed investments.
(30:34) - Rethinking the language we use to talk about the climate
(34:58) - Lessons from the worst investment Sundeep has made
(37:34) - Reasons why Sundeep is hopeful for the future of climate tech