Harry Holcomb says prison helped put him where he is today.
The 37-year-old was once going nowhere fast, a self-professed “punk-ass kid.”
Today, Holcomb is ensconced as a commercial real estate-focused mortgage loan officer for Houston-based Matador Lending — and he credits his participation in Texas’ competitive Prison Entrepreneurship Program and mentorship from the city’s commercial real estate community before and after his release for helping him get there.
Bisnow/Maddy McCarty
Matador Lending Mortgage Loan Officer Harry Holcomb with Matador’s charging bull mascot
“Since I came out … I surrounded myself with other guys that have gone through the program, a very business mindset,” said Holcomb, who built pallets and waited tables while finishing his associate degree and getting required licenses after his release in 2019.
“They were very intelligent and wanting to start their own business. I had a couple of guys that were on the same track and wanting to invest in real estate as well. That kept me grounded in that space.”
Holcomb joined Matador in January, following stints as a loan originator at Zeus Lending and Lock It Lending — and after graduating from the 20-year-old Prison Entrepreneurship Program, which describes itself as a “revolution” for the state’s 120,000 incarcerated people.
He was recruited in 2016 to apply for the Texas-based program that seeks to reduce recidivism and increase economic opportunity for people in prison through entrepreneurship training and reentry services.
The program accepts only 200 to 300 participants from thousands of applicants each year and relies on the help of successful business owners like Lilly Golden, principal of Houston-based retail brokerage Evergreen Commercial Realty. Golden is one of several CRE players volunteering to share their skills by mentoring participants.
Holcomb graduated from the in-prison phase by creating an entrepreneurial business plan with Golden and others. On the outside, the program helped him find initial employment, then start his mortgage lending career.
“The fact that someone that’s performing at that caliber and has created a career for themselves is taking the time to spend with someone that comes from my background … that, in and of itself, is very validating and grounding,” Holcomb said of Golden and other volunteers. “It gives a lot of the guys something better to aspire to.”
Golden began giving time to PEP about a year and a half ago. Since then, she has recruited other CRE professionals to volunteer, including her daughters and colleagues, Blair and Haley Golden.
CRE industry members offer diverse skills and experience that can help the participants envision and shape plans, including opening their own businesses, Lilly Golden said. Brokers teach participants like Holcomb how to negotiate a lease, while developers can educate them on matters like business utility requirements.
“We can help them to know how they should approach people, what their marketing should be, what kind of finances they need to start with, and many of the things that are going to be helpful to them,” Golden said.
Courtesy of Evergreen Commercial Realty
Evergreen Commercial Realty’s Haley, Lilly and Blair Golden at the Prison Entrepreneurship Program’s 2025 graduation
Seeing participants’ desire to be successful is the payoff, Golden said, adding that decades into her career, it’s nice to mentor someone at the beginning of their business journey.
“It’s really fun to see people that are really, really hungry [for success],” she said. “They have so many obstacles in front of them, but they’re not going to let them get in their way. There’s no complaining, no whining. They are going to make it.”
PEP participants are heavily dependent on mentors and “servant leaders,” who have already completed the program. People in prison don’t have access to the internet to research their business plans, for example, Holcomb said.
Holcomb’s business plan was for a multifamily community on a zero-loop system, meaning one that creates no waste. Plans for the community called for an indoor hydroponic produce farm managed by the staff, with goods provided to residents in exchange for a premium included in their rent.
“I would write out, ‘This is some information I need,’” Holcomb said. “They’d scour the internet and send it back.”
PEP has had 3,450 graduates since 2004, according to a 2025 fact sheet provided to Bisnow. More than 700 businesses have been formed by graduate entrepreneurs, accounting for a $122.5M economic impact in Texas, the organization said.
Graduates have a 10% recidivism rate, much lower than the national average of 50%, according to the nonprofit. PEP also boasts a 100% employment rate within 90 days of release.
PEP has a history of being helmed by those who have been caught up in the system themselves, with limited options after being branded as felons. From 2018 until late 2023, the nonprofit was led by Houstonian Bryan Kelley, who was given a life sentence for murder in 1992 and was an early PEP graduate.
“I took a life in a drug deal that went horribly wrong,” Kelley told the Texas Standard in 2021. “During my incarceration, actually early on, I just had an epiphany. I was just tired of being part of the problem; I wanted to be part of the solution.”
Current PEP CEO Chip Skowron is a former hedge fund manager who was convicted of insider trading and spent five years in prison.
“What’s really special about PEP … is that the community that we really focus on building on the inside actually transcends the fence and is also present on the outside,” Skowron said in a podcast interview late last month.
For Holcomb, one of the most valuable parts of the program allowed participants to complete mock interviews. That helped him overcome his setbacks and land early jobs doing manual labor and waiting tables while making contacts, getting an education and becoming licensed.
“For lack of better terms, I was just a punk-ass kid before I got locked up,” said Holcomb, who served four years of a five-year prison sentence stemming from an assault charge after several run-ins with the law.
“But going through the program, it put a lot of really good, positive ideas in my head and a positive peer group to be around,” he added. “The mentorship helps validate a lot of that.”
Holcomb said that he sometimes spends hours listening to TreppWire and real estate podcasts and is pursuing a bachelor’s degree.
“Knowledge is something that you can’t take away from someone, like their time or their freedom,” he said.
