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Life after lockup: Roofing CEO reflects on year in prison for PPP loan fraud

Casey Crowther is contrite yet driven as he continues rebuilding his life and roofing company after serving time in prison. "I get that this is on me, and it’s my job to show people who I am."

  • By Mark Gordon
  • | 5:00 a.m. February 5, 2024
  • | 2 Free Articles Remaining!
Casey Crowther founded Target Roofing in 2014.
Casey Crowther founded Target Roofing in 2014.
Photo by Stefania Pifferi
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Fort Myers roofing executive Casey Crowther was quick to get in line for a loan from the federal government in spring 2020. It was a PPP loan, meant to bridge losses, or potential losses, his company Target Roofing, faced in the early days of the then-very uncertain pandemic. 

The loan’s rules specified the funds were to be used for payroll, utilities and related business expenses. 

But within the week, Crowther had used some of the funds for a different purpose. He wired nearly $700,000 to a boat dealer in Sarasota and used the money to buy a 40' catamaran. It was a decision federal prosecutors later wouldn't let him forget in court and a key reason why his $1 million defense couldn't keep him out of prison, according to his attorney.

Crowther served his time — 382 days — in Federal Prison Camp in Montgomery, Alabama. He walked out Aug, 22, 2022, and hugged his 3-year-old daughter. 

Now he's back at the helm of the company he founded a decade ago. That company had 300 employees at its peak and did some $30 million a year in revenue. Now it has 90 employees; Crowther declines to disclose current revenue figures.

Crowther, in addition to running the business again, also has to face The Question: What was prison like?

It comes a little less frequently now, given he’s been out of prison for almost 18 months. But Crowther, 38, has plenty of experience with The Question.

In a rare one-on-one interview, Crowther answered the “what was prison like” question, in addition to a host of other topics. The list ranged from marketing techniques to his family to why he loves psychology books but doesn’t care for self-help books. Crowther’s prison stint — Aug. 5, 2021 to Aug. 22, 2022, came after a federal jury in Fort Myers convicted him of bank fraud, making a false statement to a lending institution and two counts of money laundering. 

“We went to trial and it didn’t work out the way we wanted it to,” Crowther says, adding the $1 million he spent on his defense came from savings and his own money. “So you have to take responsibility.”

Crowther, at different parts of the interview, uses three words — “plain, terrible and awful” to describe prison, not in any particular order. FPC Montgomery is a minimum-security prison, where a mix of inmates, from white collar to drug dealers, are housed. “It wasn’t like the movies,” he says. 

Dressed in blue jeans, brown work boots and a green long sleeve Nike T-shirt, Crowther spoke little about the case specifics in the interview. He said multiple times he knows he made a mistake and realizes he needs to take responsibility. In a text conversation after the interview, Crowther wrote that he’s learned talking about the case, and his and his attorney’s defense strategy, is not the right way to handle adversity, “right, wrong or indifferent.” (See sidebar for more on the case.)

He’s on probation, and is required to check in with his probation officer regularly. He also has begun paying restitution and fines in the case. Asked how much he owes in total, he said, “it’s some large numbers.”

‘Honor thy thug’ 

Other highlights of the interview include:

All in the family: Crowther says his thoughts in prison rarely wandered from one core: his wife Margo and their three children: a 13-year-old son, 11-year-old daughter and 4-year-old daughter. A Fort Myers native, Crowther cracks a wide smile when talking about how his kids go to the same elementary school he attended. “We basically spent all day talking about when we get to see our families again. There were others who basically felt sorry for themselves. A lot of people in prison, all they want to do is tell the world ‘it wasn’t my fault.’ I didn’t look at things that way.”

Look back: If there were other thoughts, it drifted to guilt, he says, for the pain he caused his family, friends and Target Roofing employees. “In hindsight, I wish I wouldn’t have made some decisions. I wish I didn’t have to look my best friends and my family in the eyes and tell them ‘I’m going to jail.’ There’s no worse pain in the world than feeling that.

“You don’t want to make mistakes, but how else do you learn?”

Cell block: Crowther learned the ins and outs of prison life quickly. On his second day, Aug. 6, 2021, he detailed some of the unwritten rules on a publicly available blog post. Garbage cans, for one, served dual purposes: trash receptacles and as refrigerators, when inmates put ice in them to keep things cold. Another must-do: to use the phone, Crowther learned you must say “United States of America” into it. He adds: “The phone reminds you every few minutes with a loud voice, ‘you are speaking with a federal inmate.’” 

Book it: Crowther got a chuckle out of the prison library. One early find: a book titled “Honor Thy Thug.”

Teachable moment: Crowther says he didn’t have a big life epiphany while in prison, just a realization of what he lost. “The biggest thing I took from it, what I’m very grateful for, is you really have to know what you need and what you want in life.”

“I’m going to try and do the best I can now,” he adds. “But I don’t want to sound like I got it, I learned everything. Because I don’t.”

Visiting hour: In the early stages of his prison sentence, no visitors were allowed due to COVID-19. That made the first family visit, six months in, even more special, Crowther says. A relative made a video of Crowther hugging his youngest daughter for the first time. “The amount of love I felt from that hug — I knew at the time that was something I wanted to keep the memory of,” he says. “I knew the amount of good was so perfect that I wanted to stop that moment in time so I could always relive it.”

Not fair

Prep work: The time between the conviction and when prison started, says Crowther, in some ways was harder than the actual year and change he was locked up. He says that’s because he had to face the people he let down on a daily basis. At one point some Target Roofing employees openly asked over an internal online chat — knowing Crowther would read it — if the company would be better off without him there, given the negative news swirling around the case. Crowther and the others chatted about it, and they eventually relented. 

Fort Myers-based Target Roofing works on both large-scale residential and commercial projects.
Courtesy image

Proving ground: With that in mind, Crowther says he knows his mission now in life, outside of his family, is to prove himself, much like when he was starting out. “You have to get up in the morning and you have to do it,” he says. “You have to do the right stuff for a long period of time. There’s no special sauce to it. I get that this is on me and it’s my job to show people who I am.”

Fair play: One takeaway from the experience, Crowther says, is it gives him a new perspective on parenting. Not in a scared straight way, per se, but in a be-accountable-for-your-own-actions way. That’s why he tells his kids “you’re going to hear a lot of people say what’s fair and unfair, and I think those words should be taken out of the human vernacular. Those words don’t offer anyone anything (but) excuses.”

Happy and content: Crowther says he starts most workdays with the field crews, getting ready for the day, which makes “me feel good, makes me feel accomplished.” He then helps the estimators and other departments. He says he lives “out in the sticks” and rarely goes out after work. “My family is super important to me,” he says. “If I’m providing for them then I’m super content. If I’m providing for people in this company, and watching them grow, those are things that I can go to sleep at night (with) and wake up content.”



Mark Gordon

Mark Gordon is the managing editor of the Business Observer. He has worked for the Business Observer since 2005. He previously worked for newspapers and magazines in upstate New York, suburban Philadelphia and Jacksonville.

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