Connecting the Incarcerated With Their Loved Ones

One of the hardest things about incarceration is being separated from your family and friends. Although nothing can replace an in-person connection, personal correspondence can help incarcerated family members stay in touch. However, getting these materials through prison bureaucracies can be a Herculean task.

Pelipost helps friends and family stay connected with their incarcerated loved ones through printed photos, greeting cards, photo cards, and other printed products. This is their story.

Born Out of Love

Pelipost CEO Joe Calderon says the company was “born out of love and personal experiences” he had with his mother Becky, who was incarcerated for three years while he was in college. The prison was an eight-hour drive away, and it was difficult for the two to stay in touch.

As a result, Becky missed major life events such as Joe’s college graduation, getting his first job out of school, and buying his first car. Although he tried to send photos, doing so was complicated and time-consuming. 

“To receive pictures from home was a celebration in the cell,” Becky says. “It didn’t matter who received them, they were always shared with those around you. It’s like saying, ‘See, this is my real life outside of these walls.’”

Joe wished there was a service that could print and send to Becky some of the thousands of photos he had on his phone. “The idea stuck with me, and upon my mom’s release, we got down to business and launched a mobile app called Pelipost,” he says.

Facing Obstacles and Discouragement

The company quickly ran into some competition. However, Joe didn’t let it derail his plans.

“There was another company out there, so it [was] a little discouraging,” he says. “I’m like, man, somebody’s already doing this. I’m sure a lot of people out there looking to start up are like, oh, I have this great idea, but chances are somebody is already doing it.”

But he soon realized that he could do the same thing the other company did, only better. “I looked at the company and was like man… we can improve on that…. Then we just took that and we were able to make changes and make it better and grow it to what it is today.”

Success didn’t come easily – or quickly. For example, Joe says that before Pelipost had a mobile app, he launched a “really clunky” website just to see if the concept had any traction. He donated pieces of stationary with the Pelipost logo at the bottom to some incarcerated individuals and told them to go to the website to get photos from their loved ones. 

“I waited, and then one day a user popped up and then another user popped up,” he says. “So that month I think we added probably like 20 users, which is not huge, but… for an entrepreneur, when you see that first user come in, let alone pay for a service, you’re like, wow, this is great. So much motivation, such encouragement there. So that’s kind of the early stages of how we started to really feel out and test to see, hey, we got something here.”

Filling Orders

Another challenge Pelipost faced was how to actually send correspondence to various prisons, all of which have different (and often Byzantine) procedures.

“When we were in the early days, I got that first order and I’m like, great, what do I do now?” Joe says. “I needed to print these photos, so I would go to Walgreens and print them out. But… you start to realize in our industry, every correctional facility has their own rules, regulations, and limits on photos. So you have to be able to control that as a company [to ensure] that our customers’ photos were actually getting delivered, not being returned or rejected by the correctional facility.”

Today, Pelipost has shipped more than 10 million photos and serves over 500,000 customers around the world from its fulfillment center in Tampa, Florida.

Advice for Founders

Joe says his No. 1 piece of advice for founders and early-stage entrepreneurs is to “be a jack of all trades but a master of none” – a cliche, but one that rings true.

“You have to ask for help,” he says. “You have to reach out and get advice. I’ve made the mistake of thinking, you know what, I can do this. I can do it myself. I can do the heavy lifting. But there are people out there that specialize in things, and you can network with these people, [and] get information to help you succeed. So that ultimately is the advice I would give is to know what your limit is, and then know when to ask for that support, when to ask for that help.”

He also says not to be overly concerned about what other people think. Entrepreneurship is a unique journey, and not everyone will understand the choices and sacrifices you’re making. And that’s okay.

“People are going to criticize, people are going to say, why are you doing this? You have to stay the course because ultimately you’re gonna see that traction. You have to ignore the outside noise and just go with what you feel. And if you have the drive to do it, you’re gonna succeed.”

What’s Next for Pelipost

Joe says one of his upcoming projects is to start a podcast. He also hints that new product offerings are in the works and points to the company’s recent launch of its line of greeting cards. 

In addition, he wants Pelipost to start working directly with correctional facilities to help things work more smoothly for everyone.

“Ultimately, if we keep that line of communication open, that’s going to be better for our customers, because our photos will be delivered [and we will all be] on the same page,” he says.

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