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.