From Federal Prison to Entrepreneur | Doug Feller’s Comeback Story :Reentry Truth

The Farm Kid Who Built an Empire

Doug Feller grew up on a farm in northwest Indiana, just outside Chicago. He had two great parents, an older brother and sister who were nine and 14 years older than him. “I was almost like an only child,” Doug told me. “Nothing was handed to me. I was taught the hard work of living on the farm.”

But Doug had a hustle from day one. Before he even had his driver’s license, he was cutting firewood and delivering it around Chicago and northwest Indiana. “I had a kid that would drive,” he said. That firewood business bought his first car. His parents didn’t give him money for it. He earned it.

While most kids his age were heading to college, Doug got right into business. “I was literally working a hundred hours a week and that’s no exaggeration,” he said. The money came fast. So did the lifestyle. “I did a lot of partying. I did things that I look back now and with kids and everything else, I’m like, gosh, I don’t want my kids to ever do the stuff I did.” He wondered how he survived it all.

When Success Turns Into Investigation

By 2005, Doug had married and decided to straighten up. He quit the fast life and thought everything was behind him. Then came the knock on the door in 2006. Tax evasion, fraud, and money laundering charges. The investigation covered his activities from 2002 to 2005, right before he’d cleaned up his act.

“Should I flee? Should I go to some other country?” Doug said. “I actually packed just a single bag and was gonna do I just flee and take off? I mean, that was one thought. I knew my wife was pregnant and was like six months or so along. And so, no, I’m leaving my family.”

The wheels of justice turned slow. Four years passed between that initial knock and his actual indictment. Four years of living in limbo, watching friends scatter, dealing with the stigma before he’d even been convicted.

Planning a Music Festival From Federal Prison

Here’s where Doug’s story gets wild. In August 2010, he decided to create a music festival in Springfield, Missouri. Show Me Music Fest was set for Father’s Day weekend 2011. Tim McGraw was headlining. Train, OneRepublic, Little Big Town, Big & Rich with Gretchen Wilson. A massive first-year festival with camping and everything.

Then Doug got indicted in November, sentenced in February, and had to self-surrender to Leavenworth on March 1st. The festival was still happening in June.

“So I’m sitting in federal prison in Leavenworth and I got this huge music festival with 30,000 people getting ready to take place in Springfield, Missouri and I’m not even anywhere around,” Doug said.

He’d lined up other people to run it and made plans for them to visit him every other weekend so they could coordinate. Nobody came. Nobody would take his phone calls. The festival happened anyway. Thirty thousand people each day. But it lost about $400,000 on a $4 million budget.

Building a Business Plan Behind Bars

Instead of just doing time, Doug got to work. His wife had moved to Lamar, Missouri, a small town near Joplin. Doug knew he’d be going there when he got out, so he started researching what kind of business he could build in a town of 5,000 to 7,000 people.

He settled on asphalt repair. Construction was something he knew from his real estate development days. But he’d never done asphalt work specifically.

“I would email my mom from the computer room and talk to her on the phone,” Doug explained. “And I’d ask her like, will you look this up? And she’d look stuff up and she’d print off information and pamphlets on what does this type of piece of equipment cost or where can you get it from? What is the rates here? What’s the competition?”

His mom would mail him research packets multiple times a week. Equipment costs, competition analysis, pricing structures. All legally mailed through the prison system. Doug put together a complete business plan while locked up, targeting the triangle between Tulsa, Kansas City, and Bentonville, Arkansas.

From $10 an Hour to Superior Asphalt

When Doug walked out of Leavenworth in 2012, he had his plan but no money. He spent a couple months in a halfway house, then got a job selling flooring and mattresses in Lamar for about $10 an hour. His dad gave him an old beater pickup truck from the farm.

But Doug stuck to his plan. He focused on business-to-business relationships, targeting apartment complexes, strip centers, property management companies, hotels, and restaurants. McDonald’s needs their parking lots striped. Hotels need their asphalt sealed to prolong its life.

The margins were there. The demand was real. Doug built Superior Asphalt into a thriving Midwest company and eventually sold it.

Why My Harvest App Exists

Success after prison put Doug in a unique position. He knew what most people don’t understand about reentry. “Getting out of prison isn’t the end of the sentence, it’s the beginning of the climb,” Doug said.

That’s why he built the My Harvest app. It’s a roadmap for people coming home to rebuild their lives. Because Doug learned something the hard way. The real nightmare starts when you get out.

“The deck, the cards, they’re stacked up against you completely,” he told me. “And that’s when, honestly, the real nightmare starts. And I didn’t realize that until I had to experience that.”

The stigma follows you. People scatter. It’s legal for employers and landlords to discriminate against you for being a felon. Even 15 years later, Doug still encounters it. “There’s people that are like, oh man, oh, you’ve been to prison, you’ve got to fuck. Oh, you know, they just even want to touch you.”

What Doug’s Doing Now

“What’s my legacy?” Doug asked himself. “Could have just said, I’m writing off into the sunset. What’s my, what’s, what am I really doing to make a difference in this world? And I’m taking all these highs, all these lows that I’ve had and I’m like, I want to give back and help the men and women that have been the same places that I’ve been that are trying to figure out how do I better myself? What about their families? How do we really make a difference?”

That question drives everything Doug does now. The My Harvest app isn’t just another tech product. It’s a solution built by someone who lived the problem. Doug knows what it’s like to have everything, lose it all, and build it back from nothing. Now he’s using that knowledge to help others navigate the same path.