Gary Stewart

TAKING A LONGER WALK TO FIND A TRUE PATH. For Gary Stewart, the path to entrepreneurship wasn’t a linear experience: “I was born in Jamaica, grew up in the Bronx, attended Yale Law School, and truly thought I was going to have a nice, simple, conservative life as a lawyer in New York City—but no! No, that’s not at all how anything really happened,” he laughs. Gary is the CEO of FounderTribes, an innovative learning technology platform that empowers entrepreneurs to raise capital and upskill their business models.

Gary got his first taste of entrepreneurship—with another gay co-founder, he raised four million dollars to create a gay networking platform. Gary moved to Madrid to teach at a business school, and then moved back to London to run corporate accelerators for a large corporation. “During that time, I had my hands in a lot of really big things, a lot of big money, a lot of early, important start-ups—but I never really saw anybody that looked like me,” he notes.

This focused Gary on diversity. “Could we find more Black entrepreneurs? More gay entrepreneurs? I was both and I couldn’t figure out where these individuals were or how they were developing networks.” Gary turned his newfound passion into his day job by starting FounderTribes. “When you’re a lawyer or a doctor, you go through years of schooling and then practical experience, before you’re formally unleashed into your profession—but that’s not how it works with entrepreneurs, where you just get thrown right into it. It’s scary for everyone involved.” Gary seeks to change that.

Every single day, FounderTribes works to do three things: provide Founders with inventive, thoughtful feedback to help them think critically and strategically about their goals and vision; help Founders develop the right questions about their own work and search for questions about their intended consumers; and make warm introductions to investors or funding sources to help scale their business with growth in mind.

CREATING NEW NORMS. Gary hopes to change the normative culture of tech. ”There is still this pervasive, driving culture of straight, white, cis tech-bro demands that are often placed into the landscape. My aim is to add more diversity and diverse value into that landscape, with intention,” he notes. “I have a theory that many early entrepreneurs are often nerdy and unpopular, so when they get their first taste of success, they place themselves into the center of a new ecosystem, but one that’s built from what they know, instead of what they saw as possible,” Gary explains. He believes there has been exclusionary access to funding and capital—because the structure of new power is often old power structures with different people orchestrating them.

Yet he sees the culture is evolving, noting that “we are swiftly moving into a space where everyone is being welcomed to the table,” and he believes that the new normative culture will not just be more inclusive, but also that historically disenfranchised people are primed to participate in this evolving culture, because “people assume entrepreneurs are inherently brilliant or gifted, but that’s not often the case—they often just work really hard and build networks, and push their needs forward with conviction. This is something that modern LGBTQ people and people of color have been doing for decades, and it’s all transferable!”