The Incredible Story of Pigeonly, an App That Mails Photos to Prison Inmates

Last Friday, Planet Money ran a podcast called The Prisoner’s Solution about Frederick Hutson, co-founder and CEO of Pigeonly.

It is an incredible story.

It’s not specifically incredible because it is about a man who built a multimillion-dollar business after spending four years in federal prison on a marijuana distribution charge — although anyone who builds a multimillion-dollar business is pretty incredible.

I am fascinated by this story because of all of the obstacles that Hutson had to overcome — obstacles that were put directly in his path by people who were trying to help him.

A bit of backstory: Hutson, as Planet Money explains, is one of those born entrepreneurs:

He had a lawn mowing business where he got other kids to actually mow the lawns. He did the same thing with a car washing business.

Unfortunately for Hutson, one of his entreprenurial schemes involves marijuana, and he ends up serving time in prison.

In prison, Hutson decides he’s going to study business seriously and starts learning about business plans, financial models, etc. He even comes up with a great business idea: an app that allows family and friends to mail photos to inmates without the hassle of going to a photo center or FedEx Office, printing pictures out, finding envelopes and stamps, and the rest of it. Just hit a few buttons on the app, and your loved one gets a photo in the mail.

It’s when Hutson gets out of prison that he starts running into problems — again, from the very people who are trying to help him.

Now, you’d think that entrepreneurship would be a great choice of career for a former prison inmate; you’d bypass all of that prejudice and hiring bias against people with criminal records, and you’d be able to set your own value in the marketplace. Entrepreneurship could be a way out of poverty and minimum-wage jobs.

Except, as Hutson learned when he was sent to a halfway house in Florida, he was not allowed to be an entrepreneur. As Planet Money explains:

At this halfway house, every aspect of his life was controlled. He didn’t have the luxury of uninterrupted time in that prison library. He had to constantly check in or check out. And they kept saying, you have to get a job. And no, starting your own company, that doesn’t count.

So Hutson, while he is at the halfway house, is literally building the company that would become Pigeonly in secret. The halfway house would not allow residents to have cell phones — this was late 2011/early 2012, and Hutson was not allowed to have a cell phone — so when Hutson finally connects with a potential printing client, he has to sneak a phone into an eight-person bedroom just so he can make the call. In his own words:

I had to sneak my phone in. So they had a rule, which is stupid, but you can’t have a phone. They didn’t let you have a cell phone. So I used to sneak my phone in and I would be in my bunk laying to the side and on this conference call with our vendor and the CEO and the sales guy. And basically I have to pitch him.

That illicit phone call turned out to be the right career move for Hutson, because the CEO of the printing company recognizes the strength of Hutson’s idea, agrees to help, and from that point Hutson and another friend start looking for investors and raising money to get Pigeonly (then called Picturegram) off the ground. But the company Hutson is co-founding can’t “count” as a job until it raises enough money for one of the other founders to hire Hutson as an employee.

I had no idea that entrepreneurship “doesn’t count” as a career option for people who have spent time in prison. (I don’t know, by the way, if this is on a state-by-state basis, or a halfway house-by-halfway house basis. Maybe there are some parts of the country where entrepreneurship is an option.) I also had no idea that — in 2012 at least — people in halfway houses were not allowed to have cell phones. Part of me wants to jump up and down and shout “but how do you expect people to successfully integrate into society if you do not allow them to use the resources and tools they need, like cell phones?”

Pigeonly is now a huge success, but it’s a success because Hutson broke the rules, not because he followed them. If he had done what his halfway house had asked him to do, there would be no way that he would now be the CEO of a multimillion-dollar business.

Do you think this is a one-in-a-multimillion-dollar story, or do you think we should put more resources towards helping other former prison inmates become entrepreneurs?

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