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From Prison to Pigeonly

Fifty-one months in federal prison gave Frederick Hutson a business idea. One year after release the idea had earned $3

From Prison to Pigeonly

Frederick Hutson’s is an unusual career path: in 2005 he was arrested for trafficking marijuana. He was sentenced to nearly 51 months in federal prison. Once there, “I was exposed to a problem I knew nothing about,” he said as the fourth and final speaker in this year’s Bright Lights, Green Sights series. Keeping in touch with family and loved ones proved both difficult and expensive despite evidence that maintaining these connections reduces recidivism. “Technology was at a point where this could be solved,” said Hutson. “But no one was building solutions for this demographic.”

Upon leaving prison he founded Pigeonly, which focused on providing services that keep communication open between inmates and their families. The company started with a very specific market opportunity: providing photographs to people in prison. Families and loved ones uploaded pictures to Pigeonly; the company processed, printed, and then mailed each photograph to inmates.

  Frederick Hutson, Pigeonly

The idea took hold and people increasingly began to use their service. Energized—and still on probation—Hutson and his cofounder moved operations to Silicon Valley, applied to incubators, and began the venture rounds.

“Raising capital is the most time-consuming thing you will do,” Hutson explained. “You spend so much of your time ruling out people who are not going to move forward so that you can spend time with those who will.” The gap between his personal experience—the imprisonment that inspired his business—and those on the other side of the table only compounded the challenge; he had to spend as much time explaining the problem as he did the solution. As an African-American, he also looked different than everyone in the room and, from this, learned to overcome bias, whether explicit or not, with numbers. “Let your numbers talk for you,” he advised.

Hutson found six backers and, from there, began to build his team, learning how to be a CEO as he went. “I’ve come to realize that the job as CEO is not to understand all the nuts and bolts of how the business actually works, but to focus on the ‘what’: what can you actually build? Others can figure out the how.” He had no experience in computer science or software engineering, so that’s where he started to hire. “Be cognizant of what skills and talents you have, then build your team as a complement,” he said. The same consideration applied to fundraising: though happy at the very beginning with anybody willing to write a check, once Hutson had the business running he sought investors who could directly add value as the company grew in specific markets.

Pigeonly’s expansion eventually forced internal conversation about what market, precisely, the company served. “When we started, we just wanted to make it easy to get photos,” Hutson said. But as they learned more about their customer demographics—the families of inmates, often poor, often minority, often unbanked—the mission became more ambitious. Today, Hutson said, Pigeonly intends to make poverty less expensive.

“There is an insane amount of opportunity that people are missing—which I’m fine with—for building tech products for underserved markets, building things that solve problems,” he said. He named financial service products and job search engines as two examples. “I want to create technology products that disrupt and solve for folks that most of the industry doesn’t have time for.”

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