Foster Care, addiction, prison, to master tattoo artist entrepreneur- Shawn Medina

What happens when a nine-year-old finds himself waiting on a front porch until 2 AM every night, hoping his drug-addicted mother will come home to let him inside?

When I sat down with Shawn Medina, I knew I was about to hear a story that would challenge everything most of us take for granted about childhood, family, and second chances. Shawn’s journey from foster care to federal prison to becoming a successful tattoo artist entrepreneur isn’t just about survival, it’s about the raw transformation that happens when someone decides to build something meaningful from the wreckage of their past.

From California Beaches to Missouri Brick Buildings

Shawn’s childhood reads like a roadmap of instability. Born in San Diego, he spent his early years bouncing between his drug-addicted mother’s various apartments and his grandparents’ house, the only stable anchor in an otherwise chaotic world. At nine years old, the system finally intervened after neighbors noticed something deeply wrong.

“My sister and I would be sitting out on the front porch of our apartment till like 2:00 in the morning like pretty much every night waiting for my mom and her boyfriend to get back home and let us in the house,” Shawn told me. That image, two small children waiting in the dark, captures the heartbreaking reality of what passed for normal in his early life.

After a brief stint in foster care, Shawn and his sister were shipped off to live with their father in St. Louis, a man they barely knew. The culture shock was immediate and jarring. “We leave the airport going to get into this piece of crap old truck and drive to my dad’s house and like I’ve never even seen a red brick building before,” he remembered. What followed were four years of witnessing his father’s alcoholism and abuse, trading one form of dysfunction for another.

The Gladiator School Years

Fast-forward through teenage years marked by crystal meth addiction and escalating criminal behavior, and Shawn found himself facing 62 months in federal prison. But it wasn’t just any prison, he landed at USP Terre Haute, a maximum-security facility he describes as “gladiator school.”

“When I was at Terre Haute, 80% of the population had either 30 years or better or weren’t going home at all,” Shawn explained. This wasn’t a place where people worried about rehabilitation or getting out. It was survival, pure and simple. The first day on the yard, he witnessed a full-scale riot while trying to figure out which handball courts he was allowed to use based on his race and geography.

It was during this brutal period that Shawn made what he calls the first conscious decision of his life to create a plan for his future. He’d always been artistic, using drawing as an escape mechanism throughout his chaotic childhood. Now, surrounded by men with nothing to lose, he decided to become a tattoo artist. It was strategic survival, tattoo artists in prison live like kings, protected by their value to the population and flush with commissary money.

The Hardest Prison of All: Coming Home

Here’s what surprised me most about Shawn’s story: the hardest part wasn’t surviving maximum security prison. It was coming home. After doing 100% of his sentence (he’d lost all his good time due to violations), Shawn walked out to face a world that had moved on without him. His construction skills meant nothing when insurance companies wouldn’t cover a felon. His relationship with his young son was nonexistent, another cycle of absent fathers repeating itself.

“I remember I would find myself standing in the living room of my dad’s house looking out the front window and just being stuck,” he told me, describing a paralyzing depression that kept him trapped inside, unable to even leave the house to look for work. “I would just be standing behind that window knowing that I needed to get my feet moving out the door to go find a job and I just could not leave the house.”

But here’s where Shawn’s story takes its most remarkable turn. The same artistic skills that kept him safe in prison became the foundation for a legitimate business on the outside. Today, he runs a successful tattoo shop, has rebuilt relationships with his family, and uses his story to help others navigate their own transformations.

What struck me most about our conversation was Shawn’s unflinching honesty about the ongoing challenges of rebuilding a life after prison. There’s no Hollywood ending here, just the daily work of choosing differently, building trust one relationship at a time, and refusing to let your worst chapters define your entire story.