Princeton Epps: His Jagged Journey Into the Straight Life

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You own a home in a suburban neighborhood. Decent job, good marriage, nice children. You donate to charities, volunteer for good causes, go to church on Easter Sunday. You’ve followed society rules and embraced tradition. The Black culture of inner city Milwaukee is as foreign to you as Tajikistan.

For many urban Black Milwaukee residents, the road to that kind of lifestyle is littered with gates. To get past those gates sometimes means climbing over the barriers. Which brings me to the subject of this story, 36-year-old Princeton Epps, successful businessman and business owner. His jagged journey could be made into a movie starring Denzel Washington. I met him at a coffee shop in Wauwatosa where he reviewed his life, no holds barred. 

As a kid, Princeton Epps lived in a number of different places in Milwaukee’s inner city: up and down Keefe Avenue, on East Concordia, on Humboldt and on Pierce. He lived with his mother and older brother. When at times his mother was unable to pay the utility bills, he stayed with his grandma. From kindergarten on, he attended the Shorewood schools, but Shorewood could not save him.

Epps was 14 years old and in ninth grade when he was expelled from Shorewood High School. One day, while riding a city bus, Epps got into an altercation with a man and pulled a gun on him. “I went to jail for a month,” he said, “and I spent another three months in Juvie. Luckily, they didn’t charge me as an adult. After that, I continued to get in trouble until my mother kicked me out of the house after the neighbors and the landlord complained about my bad behavior.”

At 14, Epps had no home and no school. To make ends meet, he was dealing drugs on the streets, sometimes long into the night. His north side territory ran from Keefe Avenue and up along Port Washington Avenue. He and his buddy slept in drug houses or abandoned cars. He got relief when his aunt let him live with her on 5th and Meineke, and she enrolled him in an alternative school, but he got kicked out. 

“As a condition for my pulling a gun on that bus,” he said, “I enrolled in a program with the Running Rebels organization. They help mentor young people in need. Running Rebels gave me a case manager, and I completed the program. But I kept dippin’ and dabbin’ in selling drugs on the street. Then, my aunt kicked me out of her house. Luckily, an older cousin allowed me to stay with her on 95th & Silver Spring.” 

“You were pretty young to lead the checkered life of a nomad,” I said. “How old were you then?”

“I was 16ish,” he said, “and I soon saw a business opportunity in dealing drugs in my new neighborhood. I built up that whole Silver Spring area with my drug sales operations. But I never did use drugs, only sold them. I never went back to public school.”

Epps started making decent money as a drug dealer. He discovered he was a good businessman. He found a girlfriend, which proved ironic because her father was a police officer. They had a son together when both were teenagers. His son is now 16. The story took on more drama. “I lived with my cousin for two years, but we fell out,” he said. “I moved down the street into my buddy’s house. Stayed with him for a year. Then, I moved to the east side to live with a chick my buddy was messin’ with.” 

Epps continued to find financial success in the drug business and kept that going for the next few years. Yet, there were downsides. “During that street life period,” he said, “I had a lot of short stints in jail. When I was 21, I got tired of the jail cycle, and I was getting nervous because I didn’t see no future for me. I got certified for driving a forklift and got some other licenses that I never used. I saw myself as financially successful the wrong way, making money off the streets illegally. I bought a couple cars. But there were friends being killed around me. Gang murders, that type of thing. All my life, I got used to killings and violence.” 

Jail Time

Eventually, Epps grew weary of the phone calls in the middle of the night with news about more killings often the result of gang fights. In 2006, he went to jail for a drug case. He explained, “My girlfriend pulled into a police station where her dad was a cop. She thought I was getting too hostile. The cops took me out of her car, they found drugs, and I went to jail. I was sentenced to do CCC time, and I enrolled in Milwaukee Technical College to take classes during the day, staying in jail at night. I never went to the classes. The day I got out of jail, I got into a domestic dispute with my girlfriend, and ended up at the Milwaukee Security Detention Facility downtown.” 

More time behind bars for young Princeton Epps. I wondered if yet another detention experience finally woke him up to seek the straight life. Not quite. 

After he was released from jail, he experienced news of more deaths in his social circle. He began living with his brother on the east side near the lakefront not far from Brady Street. He liked that area, but he was still dealing drugs in the 96th and Silver Spring neighborhoods. 

One fateful night, tragedy struck. Epps told me, “I was walking out of a bar with my buddy across the bar’s parking lot. He had just been arguing with a guy from Chicago inside the bar. Suddenly, the guy came up and shot my buddy. I stayed with him as he was dying and waited for help. The police thought I had something to do with his death, but I was cleared. Later, some rival gang members confronted me. I thought they might kill me, but I talked my way out of it, and they let me go.” 

Not long after that traumatic incident, Epps stopped selling drugs. He connected with Jre Riley, a cousin, a singer, a performer in the music business. Riley had seen the respect Epps had on the streets and also admired his skill running the drug business. “He taught me about the music business,” Epps said. “I started managing Jre Riley. Used my drug money to put on shows for him. Then, I began promoting other acts, booked music acts into bars and clubs. I also got my credit in order, and I bought a BMW for cash.”

“So then did you finally leave the streets behind?” I asked.

“Not exactly,” he said. “I had a buddy who was a general in the gang I belonged to. He was my drug source. When he got out of jail, I was hangin’ with him, tryin’ get him to invest his money in legal shit, tryin’ to get him to move his operation from where he was layin’ his head at. He started getting into a beef with a general from a Chicago gang. Bad mistake. My buddy got murdered. They shot him in his car multiple times. It was a real hit. After that happened, I finally changed my life.”

Going Legitimate

Epps took online business courses at WWBIC Training where he learned how to write a business plan. He earned a business certificate and then worked at Harley Davidson on the assembly line. He was also working out, gaining weight, getting strong, looking good. “I still did a little dippin’ and dabbin’ selling drugs,” he admitted. “On weekends, I went to trucking school and earned my Class A driver license and diploma. I found a cross country driving job at WEL Trucking out of De Pere, Wisconsin, blue and white trucks. I drove truck for WEL for about nine months and hated it. By that time, I had my own house, furniture, a couple cars.” 

Eventually, Epps quit the WEL truck driving job. He opened up a barbershop on 38th and National, the Stay Sharp Barbershop. “I liked barbershops because it’s a little like the gang culture,” he explained, “kind of a family atmosphere. In the Black community, barbershops are places for people to hang out. I became kind of a big brother to some of my barbers and customers.” 

The barbershop did well, and Epps opened another business, a beauty salon. He was about to rent a space in a third building and open a bar and club and bring in an architect. Soon, the barbershop business started going downhill. It was hard to find good barbers. By then, he was also bringing in money by trading properties. He called his new business, EPPS Investing. He would find a motivated seller and a buyer, design the contract and do the paperwork, and get paid for the transaction. His finances looked good, and he upped his lifestyle. 

He closed the barbershop and salon and gave up on the club idea. He signed onto another trucking job, driving local. He said, “I learned the dump truck trade from a great guy, Terry Price out of Germantown. Terry owned Price Transport. I hated the dumping process and wanted to quit, but I stayed loyal to him and kept driving his dump trucks.”

However, Epps did like the business side of trucking. After he left Price Transport, he bought a semi-truck and made a good living driving that rig. To expand his business, he contracted with other drivers who operated their own trucks. “I’d find the jobs, contract the work to those truck drivers, and take my cut,” he said. “In 2018, I started buying more semi-trucks. I now have eight trucks through my business, EPPS Freight. We work small runs through southeastern Wisconsin. I also bought some trailers, and I’m in the trailer rental business. I’ve also gotten into non-emergency transport, wheelchair lifted vans for handicapped people. By the middle of 2024, I plan to have 10 to 12 of those vans.” 

Helping Youth

As if his twisting path to traditional success wasn’t enough, he authored the book, ’A-Z Guide to making your first million by starting a Trucking, Brokering and Dispatch Business.’

“The audience for my book is for young guys who want to get into the trucking business,” he explained. “The book is used at some truck driver training schools, and it’s sold through Barnes & Noble, Lulu, and Amazon.” 

Epps once told me that as a teenager, it became normal for him to see his friends killed. Currently, he has been trying to impact kids before they choose to be violent. He commented about contemporary youth, “They seem like they feel you, but I don't know if it's enough of an influence when they get around their friends.” Elaborating, he went on, “As a kid and a young adult, I was in a lot of trouble. I talk to kids about staying out of trouble, staying away from the street culture, but when they get back to their neighborhood friends, they often lapse back into those bad habits. My hope is what I tell them stays in their mind to fall back on.” 

I asked if he thought of himself as a mentor.

“Lately, my time is pretty hectic,” he said. “I’m more like the movie director, Spike Lee. I stay behind the scenes. I try to influence young people who work for me. I’m kind of like a big brother. A lot of the younger crowd can relate to me.”

Several years ago, Epps created the t-shirt, “Killing Ain’t Gangsta.” His goal was to change the perception of the street people who commit senseless acts of crime.

“I see that T shirt as a positive message,” he explained. “The African American and Latino cultures are into fashion. I think the message,“Killing Ain’t Gangsta” can relate to several different races. A lot of young guys think that being a gangsta is about taking a life or beating up somebody. But it’s not ‘gangsta’ when they end up in prison.”

I asked Princeton Epps if he had long term goal.

“Financial freedom so my family never has to suffer from lack of money,” he said. “Also, I want to provide good jobs for my employees. Financial freedom also would allow me time to teach the children.”

People can purchase “Killing Ain’t Gangsta” T shirts and sweatshirts at the Epps online store, Legal Grind Clothing.