Alumni Stories: Frederick Hutson, Creative Rebel

Contributed by Dave Cass (PBC 2012 alumnus)

Frederick Hutson is a difficult man to introduce. His titles have ranged from Air Force F-16 mechanic - to prison inmate - to founder and CEO. I first met Frederick in 2012 at Techstars’ inaugural Patriot Boot Camp in Washington, D.C. I learned quickly that with Frederick, you simply can’t put him in any box. He’s soft spoken, he’s friendly, he’s multidimensional, and he’s really inspiring. While I always hate to disagree with the good people at Dos Equis; Frederick may be the world’s most interesting man. I mean, how on earth does one man go from flight lines in the Air Force to a prison cell to a board room? To answer that question, you have to spend time with the man. His unique journey is matched only by his unique personality and true entrepreneurial spirit. Frederick’s lessons go far beyond entrepreneurial success; he is the ultimate example of an individual learning from mistakes and life experiences and using those lessons to magnify his own positive impact on the world.  

Frederick’s company Pigeon.ly solves connectivity issues between prison inmates and their families. Their products help families stay close through services such as photo delivery, inmate locator, and affordable phone call support, to name a few. Pigeon.ly’s services have widespread adoption and they have been featured in The New York Times and CNN...but more on that later.

 
 

When you get to know Frederick, you learn very quickly that he is a consummate learner. Frederick views every life experience, good and bad, as a lesson-producing machine. He also has a very low tolerance for inefficiency and a very high aptitude for spotting it. Actually, it is this very characteristic that got him in trouble, for it was the spotting of inefficiencies in the marijuana supply trade that led to his incarceration. Fast forward to 2016, with the legalization of marijuana in three states, it can be said that Frederick wasn’t a bad guy back in 2007 when he was arrested for mailing marijuana from the shipping store that he owned, he was more, let’s say, ‘ahead of his time.’

Inefficiency is the source of entrepreneurship

I believe the secret to Frederick’s success is in his ability to learn, and through his constant learning, his ability to spot opportunity. Frederick started businesses before, during, and after his time in the Air Force but it was his time in the Air Force that taught him that efficiency is crucial to mission success. As he puts it, “(in the military) every detail and scenario is thought of before real-time action so that when you operate in real-time your mistakes are minimized.” The cost of inefficiency is too high not to think about details and play out scenarios before a war time scenario. The way Frederick sees it, “military efficiency can lead you to believe that the rest of the world operates that way.” But, as he would soon learn, this is not the case.  

When Frederick left the Air Force, the contrast between military efficiency and the rest of the world was vivid; so vivid that Frederick spotted opportunities almost everywhere he looked. In fact, this extreme focus on inefficiency led to, by his own admission, lapses in judgement; hence, his incarceration. But, it was during his incarceration that Frederick found one of the most inefficient systems on the planet--the prison system. Even further, he found a group of people that were perhaps the least served members of our society: prisoners and their families. Frederick knew that he had a choice to make in prison; he could lose those years or he could focus them on learning. Frederick being Frederick, he chose the latter.

In prison, Frederick dove into entrepreneurial books, venture brainstorming and perhaps before even realizing he was doing it, he dove into customer discovery. What Frederick also found was that if you eliminated violent criminals, who are in the fact the minority of the incarcerated population, there were a substantial number of individuals who are really good people but who made a life mistake, just like himself. These were people who missed their families. These were people that society sort of forgets about. Thus, there were a lack of services to help families accomplish seemingly simple tasks like sending a greeting a card or photo prints that meet prison mailing standards. (Remember--there’s no WiFi in prison.) Even making an affordable phone call proved to be so expensive that some inmates couldn’t speak with their loved ones. Every great entrepreneur I’ve met shares a very similar world view: that every problem in society is addressable. Frederick is a great entrepreneur and his focus on inefficiencies was now being focused on making a positive impact on society.

Frederick didn’t start Pigeon.ly in a sleek co-working space with kegs on tap. He did it from a halfway house. Resources? Nope, he didn’t have those either. Frederick hadn’t even utilized technology in four years; nevermind four generations of iPhones! Even more challenging, he experienced building a team and raising capital with the cross to bear of being an “ex con.” As Frederick explains it, “In some ways you’re never really done serving your time.” To help address challenges he faced, Frederick decided to lean on another group of people that positively influenced his life: mentors and fellow service members.

(Military) veterans are like-minded and committed to having each other’s backs.
— Frederick Hutson

During his reading on entrepreneurship, Frederick heard about a guy named David Cohen. David is one of the founders of Techstars, an accelerator that needs no introduction on this blog. Frederick decided to reach out on the chance that maybe David would take his call and just maybe, he may have some advice. David being a natural mentor, not only took Frederick’s call, but he also encouraged him to attend Techstars’ Patriot Boot Camp (PBC) and he even recommended his application. At PBC, Frederick connected with a supportive community of mentors and fellow Veteran entrepreneurs that, as he puts it, “are like-minded and committed to having each other’s back.” While Frederick experienced the positive influence of mentorship at PBC, in the true spirit of mentorship, he continues to serve as a mentor to those military veterans and families who are now embarking upon their own entrepreneurial journey. He also mentors prisoners focused on changing their lives through entrepreneurship too (this time legal entrepreneurship!)

Frederick made a mistake and had the cards stacked against him. Yet today Pigeon.ly has graduated from one of the most competitive startup accelerators in the world, Y-Combinator. They have raised $5M in venture capital and their services have saved inmates and their families more than $8M in phone charges and mailing services. With all that said, I have the funniest feeling that Frederick and Pigeon.ly are just getting going.

Some entrepreneurs create a product and sell it, others change an entire system, and a few rare ones completely change how we view the world. Frederick is doing all three. Pigone.ly is re-thinking the entire prison system and role of family services in that system. It is well documented that inmates who maintain closer ties with their families have better outcomes when they transition back to society. Pigeon.ly’s impact ultimately extends to society as a whole. Through technology, Frederick and his team have not only changed the lives of incarcerated individuals and their families, he has also made us re-think how we view convicts and our prison system. Perhaps most importantly though, Frederick shined a light on a population of people that are truly underserved and serves as a powerful role model of leadership talent coming from a place we may least expect it; the Air Force. Just kidding! I am of course referring to prison.

Thank you, Frederick, for sharing your story of resilience and creativity. You are changing the world and teaching us all while doing it!