The worst mistakes to make are the uninteresting ones.

A QUALITY ABOUT A PERSON THAT CATCHES MY ATTENTION: Mysterious eyes. SOMETHING THAT MAKES ME GO "AWW": Franklin Park Zoo Insta. SOMETHING I’M REALLY PROUD OF: The past year I built the world’s largest exposure notification non-profit, launching the pandemic technology in multiple states and countries. It is helping contain and combat Covid for millions around the world. SOMETHING PEOPLE DON'T USUALLY KNOW ABOUT ME: I grew up in rural Pennsylvania in a 100 acre forest.

Sam Zimmerman

Learning from making interesting mistakes

COMPLEX PROBLEMS COMPEL. Leading up to the founding of Freebird, Sam Zimmerman has always been intrigued by solving problems. “A lot of things don’t hold my attention for long unless it is complex,” Zimmerman says. As co-founder and CTO of Freebird, which provides individual travelers and businesses whose flights are delayed or cancelled the option to rebook a new ticket on any airline, the company represents more than just starting a business.

"There are a lot of businesses out there that aren’t tackling an interesting problem, or providing a unique solution." What drew him to Freebird was its risk management aspect—it was an essential problem to the company that was easy to state and understand, but difficult to solve analytically.

Empathy builds better teams. But being a good entrepreneur is more than just finding good solutions, it’s also about getting there with the right team. And in some ways, perhaps people from the LGBT community are better at this, Sam says. "An important aspect of leading a team successfully is empathy; being able to understand what others are going through and respond accordingly. And for many LGBT entrepreneurs, having empathy comes naturally due to having been on the fringe."

However, learning to connect with others came to Sam at a late age. Growing up, he had always felt a little removed from others, but it was not until he discovered he was queer towards the end of college that he felt he could begin to connect with people. “It wasn’t like I had a closeted period; I always perceived myself as a bit unlike others, but I had a pretty much de-sexualized presence growing up,” Sam says, adding that he had dated women prior to acknowledging that he was queer. It was after ending a cold and intense relationship in college that made him rethink his worldview in many ways.

The shame from that college relationship had caused an instinctive clamping down or numbing when it came to connecting with people. Without that shame, it allowed him a richer and more valuable sense of self, and the capability to act strategically in the business, while still being in touch with the needs of his team, he points out.

MAKING INTERESTING MISTAKES. "As members of the LGBT community, we have become accustomed to being afraid of failure. We should be careful to not let success, or our pursuits thereof, make us brittle or fragile, and that rich communal structures like family and friends are important in not letting that happen."

"It then becomes important to build deliberate spaces to allow the LGBT entrepreneurial community to grow safely. Feeling accepted is the precondition of self-discovery, and from that safety can one be able to ask the right questions," he says.

This means creating spaces for as many facets of the community as is possible, and practicing the art of seeing value in everyone’s stories. “For example, I would love to see and understand more about LGBT people growing old, what those relationships look like. The more spaces available for different stories, the more we can learn from their interesting mistakes and grow as a community."

Order your own copy of the Gaingels 100, today! Our mission is to encourage greater representation and create a more diverse, equitable, and accessible venture capital ecosystem. Elevating the stories of the most inspiring amongst us is one of the ways in which we do this.

Presented with Pride Here is the first collection of one hundred incredible and inspiring LGBTQIA+ venture-backed entrepreneurs featured in this year's Gaingels 100.