When you think of a fintech or VC founder, you might imagine someone with a business degree or a finance background. And if you’re picturing accurately, you’re thinking of a white guy. Probably in Silicon Valley.
If that’s what you had in mind, then you can partly understand why we find story so compelling.
Drew is one of the 2% of VCs who are Black men (). He’s likely the only VC who can claim to have played football with Aaron Rodgers before carving out a successful path in fintech where he eventually founded a VC and consultancy— and .
That’s exactly why the second episode of the podcast featuring Drew as the guest is titled “The Unconventional Path.” Listen to it and subscribe on , , and .
Building Fiat Ventures didn’t start at a whiteboard
“I wish we could say that we had a whiteboard, and said ‘Hey, we’re going to become a VC. This is where we’re going to start. This is where we’re going to end,’” Drew says to host, .
But they didn’t, he explains. They had to reverse engineer a backdoor in to found Fiat Ventures.
Earlier in his career, Drew oversaw growth and partnerships at a Series C fintech, , and his co-founder Alex Harris was doing the same role at . In their roles speaking with founders who weren’t scaling businesses efficiently, they saw an opportunity to open a consultancy, Fiat Growth.
“[We] didn’t have the money to invest in these businesses by ourselves at the time, but we knew we wanted to get into venture,” Drew jokes. So, they built their own access into it.
A unique approach
Their position was, and still is, unique for a couple of reasons. First, in providing critical insights and strategic support to help grow the businesses they work with, they get to peek under the hood and get an intimate view of the founder and business prior to investing. Second, they got the contractual right to invest in every business they worked with. So when it came time to raise money for their venture:
“We basically built a deck saying, ‘If we had invested in all the businesses that we worked with from day one when we got the right to invest, this is what our portfolio would look like.’”
Their revolutionary model offers a seamless transition from consultancy to investment. By working closely with businesses from the ground up, Drew and his team gain a deep understanding of each company's potential, challenges, and growth trajectory, ensuring they invest in businesses with a solid foundation and a clear path to success. This hands-on, dual-phase approach not only mitigates risk but also maximizes the impact of their investments, creating a win-win scenario for both the startups and Fiat Ventures.
“...We talk to almost 2,000 companies a year. Some failed, some successful. And, I know why they failed. I know why they were successful. And I can make sense of these moments very fast—and it’s not because I aced my pre-calc class in high school,” he says. For Drew, a degree in finance is a common misconception of what it really takes to succeed.
It takes being able to understand business and evaluate data. It takes a strong team. But he also looks for a common founder characteristic before he invests. It’s a characteristic he shares: A relentless “I’m not giving up” drive. It stems from his sports background and athlete’s mindset.
Lessons from the field to the boardroom
His time as a football player taught him firsthand the power of competition, resilience, and teamwork. These lessons weren’t just about winning games—they were about thriving under pressure, adapting to new challenges, and leading a diverse team toward a common goal. Today, Drew brings that same intensity and strategic thinking to the world of venture capital, where every investment is a new play and every startup a new team to coach to success.
“Sports from a very early age made me feel very comfortable in uncomfortable moments,” Drew reflects. “It gave me the ability to navigate the world regardless of the room I walk in. Socioeconomic class, sport, or topic—it gives you this flexibility to navigate the world in a very powerful way.”
Tackling challenges and embracing failure
Drew doesn't shy away from discussing the bumps in the road. He delves into the tough times and the moments that tested his resolve and taught him lessons. For Drew, resilience and adaptability aren't just buzzwords—they're the foundation of his success.
He reveals how he and his team tackle setbacks head-on, constantly pivoting and refining their strategies. Whether it's navigating market downturns or overcoming internal hurdles, Drew's relentless pursuit of success and his willingness to learn from every failure set him apart.
“You need to stay around long enough to get lucky,” Drew advises. “On my worst days, I remind myself that we’re going to push through this, keep shooting our shot, and something will fall.”
Tune in to Drew’s story
Listen to our second Next Gen Builders episode to learn more about Drew’s unconventional path to success, the unique model behind Fiat Ventures, and the valuable lessons he’s learned from sports and business.
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