From Inmate to Entreprenuer: How an Ex-Felon Created a $3 Million Startup Helping Prisoners

We talked to an ex-felon to hear about how he overcame the barriers of prison (and the stigma of having been a prisoner) and used it to his advantage.

Not Available Lead
Complex Original

Image via Complex Original

Not Available Lead

Right now there are nearly 2 million inmates in state, federal, and juvenile prisons in the United States. Ninety-five percent of them will eventually be freed, and nearly 700,000 of them are released every year—but two-thirds re-offend within three years of their release. According to studies, one of the best ways to keep inmates from returning to prison is by keeping them in close contact with family while they're inside.

But many inmates end up transferring from prison to prison during long sentences, and visitations can become increasingly difficult for family members. Sending mail is still an option, but in a society that's used to storing pictures on smartphones the process of having pictures developed, printed out, and dropped off at a post office is an inconvenience, and might lead to letters that will probably never make it to the mailbox.

Frederick Hutson knows that it's important for prisoners to keep in touch with the world—because he was one himself. The 30-year-old was sent to prison in his early 20s after he was honorably discharged from the Air Force and became involved in a sophisticated marijuana trafficking scheme that stretched from Mexico to the west and east coasts of the United States. He was sentenced to nearly four years in prison in 2007—the same year Apple debuted the iPhone. From behind bars, he kept up with tech magazines and familiarized himself with apps and smartphones so he wouldn't be left behind when he was eventually released. Then, from confinement, came opportunity. 

Hutson took an idea he got while in prison and turned it into a $3 million Las Vegas-based startup in the years since his release—and that company, Pigeonly, aims to make it easier for friends and family to communicate with—you guessed it—prisoners. Pigeonly currently has two services, Fotopigeon, which allows people to mail photos to inmates straight from their computer for 50 cents a print, and Telepigeon, which generates a local phone number for the prisoner's family members so that their calls are charged at the local rate, which can significantly lower the amount they're charged. Pigeonly is currently expanding to reach other overlooked demographics when it comes to technology.

We talked to Hutson to hear about how he overcame the barriers of prison (and the stigma of having been a prisoner) to use it to his advantage.

By Jason Duaine Hahn. This interview has been edited and condensed.

So, let's talk about the marijuana gig you were involved in.

Basically, I was distributing marijuana from Nogales, Mexico, through Tucson, from Tucson to Las Vegas, from Las Vegas to central and south Florida, using shipping carriers like UPS, FedEx, and DHL. All those. I started when I was probably 19. 

How did you get caught?

The driver of one of the connects in Mexico got stopped. When they started questioning him, he pointed to all the people I knew, and it all fell out from there. One guy pointed fingers, and everyone got indictments. It was about 11 of us on the case, and once everyone was indicted, it was pretty much a wrap. I was indicted when I was 23 in 2007.

You were incredibly young. 

At that time, I didn’t understand the legal process. I didn’t know what to expect. I’m thinking marijuana isn't a big deal—I didn’t understand conspiracy laws, I didn’t understand the difference between getting a state charge and a federal case.

I had to make a lot of choices. I had to decide if I was going to either take a plea or go to trial. I plead guilty to get it behind me as soon as possible.

How long was your sentence?

Fifty-one months, and six months halfway house time on top of that. I started the halfway house in September 2011. When I got out in March 2012, I was on federal probation—what they call "supervised released," where they do pop-up visits at your place of employment, your house, that type of thing.

Where did you serve your time?

I was in a couple county jails when I was first arrested in Las Vegas, but then I was transferred to the federal prison in Victorville, Calif., then Phoenix. I did the most of my time in Safford, Ariz. My security level points went down, and after those go down, they bring you to a lower facility. The last facility I was in was Federal Prison Camp in Montgomery Air Force Base in Montgomery, Ala.



I read these magazines about the apps people were building, and I was just on the sidelines watching these things change.


When did the idea for Pigeonly hit during all of this?

It was really just from my personal experience. One of the most frustrating things in prison was that it was hard keeping in touch with people I cared about—and it was hard for them to keep in touch with me. You’re dealing with people who work 9-to-5 jobs, and they don’t really have time to write a letter and go to the post office, or go to Walgreens to print out pictures and mail it. It was just a lot of steps to do something that’s relatively simple.

The iPhone had just taken off right before I went in. I read these magazines about the apps people were building, and I was just on the sidelines watching things change. I thought to myself, This isn't rocket science. That’s how it started; I was trying to solve my own problem. I wanted to make it simple for someone to easily upload photos from their device and then hit the send button—and those photos would be printed, mailed, and shipped to inmates.

The second problem I had was phone calls were excruciatingly painful because they were so expensive. I was paying about $70 for 300 minutes. Had my family and friends been local to me when I called them, it would have been $18 for those 300 minutes. So, just this year we introduced VoIP (Internet calling) services. 

You must have bounced this idea off the guys you were behind bars with.

What’s interesting is that I told one of my friends, who I did a lot of time with, that I didn't even know if I was going to do it—I was brainstorming a ton of other ideas. At one point I told him, “I’m not going to do the photo idea, here, you can do it.” He said, “Nah, I don’t want it, you can do it.” So, I almost gave this away to somebody. He and I laugh about that to this day.

I definitely talked to a lot of guys and got a lot of feedback. We’re shifting 8,000 to 9,000 photos a day, so there’s no question about if there was pent-up demand for a service like this. It was just about creating something that people want and that no one was servicing.

Anyone can have an idea. At what point did you see yours becoming a reality?

I was in the halfway house at the time. I had meetings with different developers, explaining what I was trying to build, and we found a vendor who would facilitate the printing and mailing of the photos. I was actually still in the halfway house on the first day that Pigeonly was built. They wouldn’t allow us to have phones, so I snuck my phone in to make calls and send emails. I knew I needed a phone to get my life where I wanted it to go. Stupid rules will always get broken. I was willing to take that risk to keep the ball moving.

It wasn’t a question if I could do it. What I didn't know was how. I just started doing research, figuring out that I had to hire a developer, and then researching that. I posted a job offer, started getting responses, and I just learned as I was doing it. As I would learn, and things got more defined and clear, I would make more adjustments.



you’re doing what you love to do everyday, and I am the master of my own fate. I prefer those cards to having to depend on someone else giving me an opportunity, especially being an ex-felon.


Wait—how were you making the calls? Were you ducking under your covers?

Yeah! What happens is that you’re in your room, and when someone comes to the door you have to stash your phone. There’s no police there—it’s just halfway house workers—but if they catch you they just take your phone away.

They put up a lot of roadblocks, but I had that six-month window there to get something going on the business, because I had a place to stay. Once I didn’t have a place to stay any more, I would have to figure out how I would pay for my bills. It was important to me to get that first product built while I was in the halfway house. It was like an incubator for me. [Laughs.]

How did you raise cash for everything?

While I was at the halfway house, I told my co-founder about the idea, and he started pulling together small amounts of money, and we raised $80,000 over the span of two years. It was raised in very small amounts of money from strictly friends and family. It really was just trying to survive until the next day. It was every single day, making decisions and aligning things to make it to the next day.

Once we were able to release it, we did a marketing push to tell inmates about the services, and they told their family and friends about it. They went to the website, opened an account, and that’s how we got our first customers. After that happened the first time, we got a strong response from it, and we started making money. Once we started making money, it never stopped, and it’s been enough money for us to keep the business going.

Then I learned what an technology accelerator was, and I started applying to every accelerator I could. When we were talking to the investment community in Florida, they didn’t understand and didn’t have tolerance for investments in technology companies. They liked real estate. We ended up getting accepted to the NewME accelerator, and that’s where we raised our first seed round of $950,000, or close to a million dollars.

That's a hell of a lot of money.

It was dope, it was great that we got the business to the point that other people started seeing the value, because of our growth and the amount of customers we had. We didn’t go into this with an idea and expected people to invest in it, but we always had numbers and metrics to prove that we were building something that was needed, and solving a problem that people would pay us for. We did it at a small scale, but it was enough to convince investors that it was a real business, not just smoke and mirrors.

1.

Did you get pushback because you're a former prisoner?

Not everyone got it. I talked to about 60 different investors, and we only had six when it was all said and done. Some people said that they couldn’t wrap their brain around investing in a felon—those things happened and came up several times, but we had to keep working and pushing through it.

How did you tell investors you're an ex-felon?

I wasn't sure how to package my prior experience, I wasn’t sure if that was something I should lead with, or if that was something that should come up in a meeting. What I realized was that my experience makes my story unique, and it means I can execute it when no one else can, because I have a deep level of understanding. That’s my advantage. Once I thought that way, that’s when I realized I should lead with it. Especially when it comes to technology, those unique experiences and backgrounds give you an edge.

The name, Pigeonly, how did you choose that?

Things that are familiar go unnoticed the most. When is the last time you noticed a pigeon? They're literally everywhere. We build products for those who go unnoticed, those no one else is paying attention to.

How many employees does the startup have today?

We have 20.

Would you consider hiring other felons?

About a third of our workforce are people with criminal histories. We have engineers, customer service specialists, management—across the board. The one thing that people don’t understand is that there are two types of people in prison: there’s the guy who generally doesn't care and has no idea or ambition to change his life, but that’s the minority of who’s in prison. That’s the super minority. The much larger majority of people being released are people who want to find a better way for themselves and for the families who care about them.

You had a window-tinting company before your marijuana business, so you had a run at entrepreneurship before, but running a startup is a new frontier.

It’s constantly doing something that you never have enough resources to do. It’s always about being creative; it’s always about how I’m trying to leverage everything you can possibly leverage, because you’ll never have enough money. You never have enough people. But it’s great, you’re doing what you love to do every day, and I am the master of my own fate. I prefer those cards to having to depend on someone else giving me an opportunity, especially being an ex-felon. I would hate to be in the position where I have to check the box where it says I’ve been convicted of a crime, that I can’t get a job or my options to seek employment are at a minimum because of that. I’d rather create my own opportunities.

I have to ask, with the skills you’ve taken on, considering your past with marijuana and how the country seems to be more relaxed with it—would you consider creating a startup that focuses on marijuana?

Absolutely, of course. [Laughs.] It’s one of those things, where, just because it’s being relaxed on the state level, ain’t shit relaxed on the federal level. So, the federal system knows me very well. For me to even come close to considering it? I would need to be relaxed with it being legal on the federal level before I can even be near something like that. [Laughs.] I ain’t gonna make it that easy for 'em—they gotta work to get me again!

Latest in Life