In a recent episode of Charlotte Talks on WFAE, Passport CEO Khristian Gutierrez sat down with host Mike Collins, StreetFair CEO Teddy Fitzgibbons, and Charlotte Business Journal tech reporter Symone Graham to unpack what’s fueling the City of Charlotte’s rise—and why Passport’s culture is catalyzing a new wave of entrepreneurship.

Meet the ‘Passport Mafia’

What do more than a dozen Charlotte startups have in common? They were all founded by former Passport employees.

Much like Silicon Valley’s “PayPal Mafia,” the so-called “Passport Mafia” is a growing group of alums who have started successful ventures of their own. As Khristian explained, this wasn’t an accident. It was the result of a company culture built on ownership, humility, and curiosity.

“We fostered grit, perseverance, hunger, and a hunger for discovery,” said Gutierrez. “From day one, we supported the idea that it’s okay to be wrong—and that failing fast is a stepping stone to something better.”

A Culture That Builds Founders

One of those founders is Teddy Fitzgibbons, now CEO of home services startup StreetFair. Reflecting on his time at Passport, he credited the company’s leadership with providing young team members autonomy, trust, and stretch opportunities early in their careers.

“It let us get some of that imposter syndrome out of the way early,” he shared. “We were given the space to figure things out—and that kind of empowerment built lasting confidence.”

It’s a mindset that continues to ripple outward. Today, Passport alumni are launching companies and mentoring the next generation of talent in Charlotte’s tech scene.

Why Charlotte? Why Now?

While Charlotte continues to climb the ranks in tech employment growth, challenges remain—especially when it comes to early-stage capital. Symone Graham noted that the region still sees limited venture funding compared to national averages, particularly for diverse founders. However, the outlook is improving, thanks in part to companies like Passport that are building credibility and community.

“We’re proving that Charlotte can produce high-growth tech firms,” said Graham. “That inspires more entrepreneurs and increases investor confidence.”

Khristian echoed this sentiment, describing Charlotte as “a great place to call home” with no shortage of talent. He emphasized the key to creating a culture that rewards curiosity, resilience, and execution—values deeply ingrained in Passport’s DNA.

Building Beyond Business

From day one, Passport’s approach has centered around more than just product innovation. Khristian shared that the mission has always been about building people—giving them the tools, mindset, and confidence to lead.

“It’s not just about what we do, it’s about how we do it. When you build a customer-centric, mission-driven organization, your people carry that forward,” he said.

He also highlighted Passport’s early equity model as a differentiator, where team members are treated as owners. This investment pays dividends not only for the company but for the entire Charlotte ecosystem.

A Lasting Legacy of Leadership

When asked what he’s most proud of, Khristian didn’t hesitate: it’s the ripple effect of Passport’s culture, measured not in transactions but in founders.

“To see people step out, take the risk, and build something great—that’s what makes me proudest,” he said. “Even if they fail, they’re learning. They’re growing. And they’re building something that might live on long after us.”

Charlotte may not have Silicon Valley’s venture capital density, but with leaders like Khristian and the Passport Mafia leading the charge, it’s carving out a legacy of its own: one rooted in resilience, innovation, and a belief that great companies don’t just build products—they build people.