The Unexpected Journey of Jim Strobbe: a Lawn Care Business Owner

When I talked with Jim Strobe on the podcast, he walked me through something that happens to a lot of guys. You build a good business, you’re making decent money, and then an opportunity comes along that changes everything. For Jim, that opportunity led to 10 years in federal prison.

Building Something from Nothing

Jim grew up in Parkville, Missouri, played baseball and football at Park Hill High School. Nothing fancy, just a country jock who was good with his hands. By the time he was 27, he’d figured out something that a lot of people never do. He stopped working for someone else.

“I worked for two different people from like 15 to 20 years old and then I’m like, you know what, I’m not making no money working for the man,” Jim told me. He bought his own equipment, got a couple trucks, and built up 38 accounts. Then 46. The lawn care business was solid.

Jim left his best accounts to his dad when everything went sideways. His father, who’s 80 now, still runs those same accounts today. That tells you something about what Jim built.

When Opportunity Becomes a Problem

“Hispanics, Mexicans, whatever you want to call them. They loved a roof and they loved to cut grass,” Jim said. He had four guys working for him, a couple straight from Mexico. “They have some plugs and connections. And I had the money then. And they like money like we do.”

That’s how it started. Jim began putting money into their connections. It turned into what he called “a good little thing” until the feds showed up.

The thing that gets most guys isn’t the crime itself. It’s the betrayal. Two of Jim’s workers got jammed up. One was Mexican, one was a white guy Jim had known since childhood. They played tee ball together, all the way up through high school.

“He sold me out. He got in trouble and he said my name. They didn’t know nothing about me,” Jim explained. That’s the federal playbook. Get one guy, make him give up names for a lighter sentence. “It’s kind of like a stockyard, you know. Why would you want one bull when you can have 10 or 20?”

The Mathematics of a Plea Deal

Jim’s lawyer was a former federal prosecutor who’d handled thousands of cases like this. The math was simple and brutal. Take the 10-year mandatory minimum, maybe get out in eight with the drug program. Or roll the dice at trial.

“He goes, I’ve lost two cases like yours in 20 years. And I won’t lose three,” the lawyer told Jim. “You’re going to leave that courtroom that day doing 20 to 22 years. We’re going to double it up. Your mom and dad will probably be passed and gone away by then. Or you can be back home and try to be a productive member of society within eight years.”

Eight sounds a lot better than 22. Jim took the deal.

The Long Road Through the System

Jim spent 14 months free while waiting for sentencing, enough time to get his affairs in order. When sentencing day came, they took him immediately to CCA in Lansing, Kansas. Four months in what he describes as basically a county jail environment before getting shipped to El Paso.

The transfer itself was a nightmare. Oklahoma City transfer center, then eight hours shackled on a plane that went from Oklahoma to Colorado to Utah and back down to Texas. “I don’t like taking an eight hour airplane ride to Hawaii with a cocktail, much less shackled where you can’t even hit your own face or nothing for eight hours.”

El Paso was 1600 inmates. All announcements in Spanish first, then English. It used to be an immigration facility, old school maximum security with four rows of razor wire. Out of 1600 inmates, there were maybe 88 white guys. Jim was the minority in every sense.

Finding Your People

Prison has its own rules. Some white guys, bikers, took Jim in right away. Filled his locker with ramen noodles and soups, got him shoes and sweatpants. But they wanted to see his paperwork first. “When you walk in with your judgment and commitment papers, it tells exactly what you pleaded to,” Jim said. Drug case? You’re good. Other things? Different story.

“You actually walk in and you kind of get a little family going of your own people,” Jim explained. It’s primitive, but that’s how you survive 1600 inmates when fights happen once a week.

Jim spent three years there, didn’t see family because of the border violence happening at the time. His dad had open heart surgery. His baby daughter Esa got bit by a pit bull. His relationship fell apart. “Everything hit me hard. That first three years was kind of a rough battle.”

Making It to Leavenworth

After 18 months, Jim should have been eligible for transfer. The BOP wouldn’t move him. His parents wrote letters to Claire McCaskill and Roy Blunt. Both senators put in a word. Within 30 days, Jim had a Greyhound ticket.

The bus ride from El Paso to Leavenworth took two and a half days. The bus broke down for 10 hours in Oklahoma. Jim arrived at 1:15 AM on a Saturday, but the camp doesn’t process anyone in the middle of the night. He spent the weekend in the hole at the medium security facility up the hill.

“You talk about feeling helpless,” Jim said about those two nights. Concrete slab, no bed, shower you had to enter sideways. Just the sound of guys beating on doors like caged animals.

Life at the Camp

By August 2013, Jim was cutting grass at Leavenworth. Thirty acres that took all week to finish, then you started over again Monday morning. When he wasn’t cutting grass, he was running a burger business out of our housing unit.

“I had a good burger business,” Jim said. Five stamps per burger, about 30 burgers a day. Guys would line up outside our door. “Burgers in prison were like crack cocaine. I mean, everybody wanted them.”

The resourcefulness required was something else. Cook them on the electric grill when available, microwave when not. Always kept five microwaves on hand, courtesy of the UNICOR factory where federal office equipment got disassembled.

Jim and I spent a year as cellmates in an 8x10 room. Snow came through the windows in winter. No heat until the week before Thanksgiving. No AC when it hit 110 degrees in summer. But we had Clark paint our room seven different colors, made it the envy of the whole camp.

Coming Home to a Different World

After seven and a half years, Jim walked out with a job lined up for his second day home. That made him luckier than 80% of guys getting out. “If people come out with no job, no family, no car, no nothing” and you’re checking that ex-felon box everywhere you go, it’s 10 times harder than anything civilians complain about.

“I’ve always been the driver,” Jim said. “It’s hard for me to be in the backseat.” Coming home means learning you can’t just jump back in as head of the household after eight years gone. Your kids haven’t had to listen to you. Your role in the family changed while you were away.

Today Jim works the same trade that got him in trouble, just without the side business. His dad still runs those lawn care accounts at 80 years old. Some things survive even when everything else falls apart. Others take time to rebuild. The tattoo saying “ex-felon” follows you everywhere, but Jim’s making it work one day at a time.