Andre Charoo (Partner at Maple VC, a colleague that I became close with in our time at Hired) lives an interesting life these days. He runs a highly successful Venture fund that is centered around the thesis of backing Canadian entrepreneurs that are scaling in America and beyond, all of this while living in South Korea! In the world of venture capital and startups, few stories combine resilience, vision, and strategy as vividly as Andre’s.

I wanted to get inside Andre’s mind and explore his journey up to this point, how he got into the VC game from Investment Banking to San Francisco Startup life and ultimately, what were some key “Lightbulb Moments” that he can point to that has influenced his trajectory into now leading Maple Ventures. These “lightbulb moments” not only defined his career but also led to his notable investment in Clay.com—a platform currently redefining outbound sales.

Andre began his Venture Capital fund, Maple VC, while working full time alongside me at Hired. Andre was able to bootstrap this fund which now has invested over $50M in close to 40 companies.

From Early Insights to Lasting Impact

Andre’s journey began in Canada, where a pivotal college experience set the stage. An economics course taught by a Reza Satchu who sold his company Supplier Market.com for close to $1B to Ariba during the dot-com boom and then transitioned to academia at the University of Toronto where he inspired Andre to explore pathway beyond the traditional career tracks.

“At first, I was laser-focused on becoming a banker, but he opened my eyes to the possibility of entrepreneurship as a viable path. That was my first lightbulb moment. He wasn’t just teaching entrepreneurship; he was living proof of it. That class changed my trajectory.”

It’s not just listening to advice, but also keeping in touch that continues to offer impact. Years later, Reza reached out to Andre to throw the rope back over the fence and help out a new batch of budding Entrepreneurs.

The seed planted during his university years blossomed into a foundational principle: value creation through innovation and one Andre careers with him to this day.

Uber and the Power of Gut Decisions
Perhaps the most notable chapter of Andre’s early career was his time at Uber. Amid skepticism from peers, Andre joined the then-nascent company in 2010, attracted by its ambitious vision. Uber’s focus on building a logistics engine for cities, coupled with the team’s relentless drive, resonated with him. Andre held the role as “Launcher”
and was instrumental in helping the company expand into new markets and was crucial
in shaping Uber’s foundation and early growth trajectory.

“I asked Travis, ‘What’s the vision for Uber?’ He told me, ‘We’re building a logistics engine for cities. Right now, it’s about black cars, but we’re going to deliver anything.’ That captured my imagination.”

People thought Andre was crazy. The smartest folks in his network said it was a niche product idea and wouldn’t go anywhere. But upon reflecting on his choice, Andre credits it with honing his ability to trust his instincts, a skill central to what he does every day and his instincts primarily centered around the person.

That experience taught me to trust my instincts and see the potential in things before others do. It’s a lesson I carry with me as a VC today.”

The Genesis of Maple Ventures

Andre’s third lightbulb moment emerged during his tenure at Hired.com. His realization of the untapped potential within Canada’s entrepreneurial ecosystem led to Maple Ventures. The fund focuses on supporting Canadian founders building globally impactful companies, bridging the gap between Canada’s talent and opportunities abroad. It was a bold move born from Andre’s understanding of how overlooked networks could yield outsized returns.

“At Hired, I realized I loved the seed stage—helping founders at the very beginning of their journey. But I also noticed something else: many of the most successful startups had Canadian founders.”

Hired also was born from Canadian founders and Andre was able to pool together a fund from them and the Board of Hired to begin Maple Ventures. But the decision to start was not as easy as you may think. After spending 4 years trying to work for the Investment Bank in Canada he wanted to join, Andre had been rejected and was forced to leave his country to start the career he wanted the right way.

Starting Maple Ventures wasn’t just about investing; it was about proving that this network of Canadian expats could outperform traditional venture models. It was a risk, many advised Andre not to do this, but he had to test the thesis.

One of Andre’s first investments was Clay.com, arguably the hottest Sales Tech company of 2024 currently valued at $500M in their Series B; but in 2017, they were very far from what they are today. Clay initially aimed to automate enterprise work through low-code/no-code tools. After years of iteration, the company intentionally focused to outbound sales automation. Much like Andre’s previous experience at Uber where they focused on Black Cars before going broader. Remarkably, Clay’s growth has been entirely organic—no press releases, no ad spend, and no dedicated sales team. Instead, the product’s excellence and an open Slack channel fostering user collaboration have driven its meteoric rise.

Andre Charoo’s story is a testament to the transformative power of intuition, adaptability, and belief in underrepresented networks. Through his investments, particularly in companies like Clay.com, he exemplifies how calculated risks and a commitment to long-term value creation can reshape industries. Something he attributes to the outsized impact he had on his first Lightbulb Moment 20 years ago.

For aspiring entrepreneurs and investors, Andre’s journey offers a blueprint: embrace the unconventional, trust your instincts, and never underestimate the potential of a well-supported vision. As Clay.com continues to disrupt outbound sales, it stands as a beacon of what’s possible when ambition meets execution.

The Legacy of Lightbulb Moments
“If you want to create outsized impact, you have to embrace the unconventional and trust your instincts. That’s what I’ve tried to do, and it’s what I look for in founders.

Upon reflecting, Andre adds up the lightbulb moments which, at the time, seemed small, but they shaped everything for Andre.

“You never know when you’re in one—it only becomes clear later.”