From Prison to Purpose: How Losing Everything Rebuilt His Life

Positive Kyle Lassiter introduced himself on episode three of The Entrepreneurs’ Club Podcast the way he introduces himself everywhere: as a formerly incarcerated prison survivor. He is also a father, a grandfather, a college graduate, and the owner of several businesses across the Lehigh Valley, where he has lived for almost 30 years.

Speaking with Carter McKinney at Venture X in Bethlehem, Lassiter was open about the failures as well as the successes. His message, he says, is that bad choices do not have to mean bad choices forever.

Twenty years in and out

Lassiter grew up in New Jersey. His mother moved the family to Pennsylvania for a lower crime rate and a better life, and he graduated from Allen High School. But he fell in with the wrong crowd, learned the drug trade, and spent about 20 years going in and out of prison on drug convictions.

He traces the start of it to the loss of his father, who died when Lassiter was 14. From then until he was 38, he says, he was back and forth between selling drugs and getting caught.

Coming home brought its own walls. He once applied for a job at the arena in Allentown when it first opened, along with more than 1,500 other people. He had a degree in accounting, made it through three interviews and got the offer. Then the background check came back, and the offer was withdrawn.

“When you in there it feel like life is easy, but when you walk out, life is hard.”

The mentor who kept showing up

The turning point was mentorship. A man Lassiter had been arrested with came home, changed his life, and started doing community work in Allentown. Lassiter watched it on social media and kept running into him, including at two separate weddings. At the second one, he asked for a chance to join the program.

He volunteered for more than a year without pay, mentoring youth, running book bag drives, feeding the homeless and visiting schools. He eventually spent close to 10 years in community work, including as head facilitator of a paid training program where participants earned $20 an hour learning hard skills like landscaping and snow removal.

Today he is part of a prison survivor network whose CEO teaches a curriculum called TREE: trauma informed, restorative practices, emotional intelligence, equity and inclusion. Lassiter says the course helped change his life, and he hopes to teach it inside prisons one day.

Building through the back door

When dealerships would not hire him because of his felony, Lassiter opened his own LLC to sell cars. That is when it clicked: a conviction did not stop him from owning a business. He has now held his Pennsylvania dealer license for 11 years with no infractions and has sold more than 1,000 cars.

Next came lawn care, where at one point he had 250 clients and cut every yard himself. Then general contracting, since contracts did not come with a background check. Today his work includes snow removal with five plow trucks, flips, and property management covering 245 properties and four complexes in Allentown. He bundles the work so that cleaning, landscaping, snow removal and contracting all come from his own team. His partner runs his calendar and keeps the operation organized.

Not every door opened. Lassiter went to real estate school and passed, but the state pulled his license over his conviction. He says that after then Attorney General Josh Shapiro heard his story at an event at Lehigh University, the state created a waiver process for applicants who go before the board.

“Oh, the felony conviction don’t stop me from owning my own business.”

Advice for the next step

For people coming home, Lassiter’s first piece of advice is to find the right support system: organizations that help returning citizens, a partner who pushes you, and a circle that inspires you. He believes more employers are open to hiring people with records than 20 years ago, and that extra courses can help people move up.

For entrepreneurs, he suggests giving a business a three year curve and expecting losses early. Through the network’s weekly book club and Sunday morning “power hour,” he wants to keep sharing what he has learned. He adds that a person can be in prison mentally without ever seeing a cell.

“Losing is winning.”

What his father taught him

Lassiter remembers being angry with his father every summer. At 10 he was cutting down trees while other kids played basketball at the park. Then came a paper route, then buffing floors on custodial jobs, then selling radios, clothing and hats at a flea market.

Years later, those lessons came back. He has made $3,000 cutting down a single tree, and he ran an eBay store reselling hot electronics. He named his company Lassiter Enterprises to carry his father’s legacy forward. His own children have never seen prison, he says. One son, Bubba, is now a DJ, and another manages the lawn care business.