becoming a barbershop owner in connecticut

OB’s Story: Becoming a Barbershop Business Owner

From Self-Taught Trims to School-Certified Credentials:
OB’s Journey to Becoming a Barbershop Business Owner

Osvaldo “OB” Lugo’s path to becoming a barbershop business owner has been a long one. Although previously incarcerated, OB has embraced his passion to become an entrepreneur, pursued his education, and rediscovered his purpose as a student of Goodwin University’s Entrepreneurial Network (ENet), an 18-college-credit-certificate business program for the formerly incarcerated. The following is his student success story. 

When OB was growing up in rural Puerto Rico, haircuts weren’t a necessity. “We had to do it ourselves and make it look as similar as possible to the haircuts we saw on TV,” he explained. “Then, little by little, I started asking questions in different barbershops, and I picked up the trade.”

After high school, OB relocated to the United States, where he discovered that cutting hair was what he truly wanted to do as a profession.

“Cutting hair made me popular in the community, and I liked that,” he revealed. “I also liked controlling my own hours — being able to walk out of my job at any point to buy a soda or go home was, and still is, important to me.”

But before OB could realize his dream of owning a barbershop business, he was sentenced to 10 years in prison. But even while incarcerated, OB “always kept a barber job.”

From paper to possibility 

Throughout his time served, OB made inmates feel better about themselves through haircuts, increasing self-esteem regardless of their confined circumstances.

“In prison, one thing that people do is write down our dreams and goals on paper because that’s all we got, a piece of paper, pen, and time,” OB shared.

“Thousands of people are coming back into the community with their dreams written down on a piece of paper, but they don’t have the right people to make it happen. Fortunately, I stumbled on the right people at the right time.”

Hope through happenstance 

Once Osvaldo was released, he heard about Goodwin University’s Entrepreneurial Network (ENet) and the opportunities the program offered through his friend Daryl McGraw. McGraw knew about OB’s dreams to start his barbershop, and he thought OB would be an ideal participant in the program.

“In prison, I wrote the name of my barbershop down a thousand times: LookSharp Barber Shop. I wrote down the blueprint of what the business would look like — the sign, the logo, and I would ask people which name looks better. I used to do surveys about services and prices. I did my research. When you look sharp, you feel sharp, and I wanted a name that could connect with everybody.”

When OB joined ENet, his vision of owning his barbershop started to become a reality. “You go from having an idea to formulating and quantifying that idea,” OB expressed.

Students whose time stood still 

But on his first day of classes, OB felt out of his norm.

“I had fears and doubts,” he acknowledged. At 42 years old, “I thought I was too old to go back to school.”

“All of us in the program went to prison,” OB described, “and not all of us are knowledgeable about computers. It’s hard to tell me to turn on a computer when I don’t know how, and for professors to step down to meet me halfway was appreciated.”

“With people that come out of prison,” OB detailed, “if you put them in a setting where they are embarrassed about simple stuff, like lack of understanding about technology, they’re going to shut down. Other students were apprehensive, too. But through the weeks, especially with Professor Matt [ENet Program Director Dr. Matt Connell] calling people and reaching out, students began to let their guard down.”

“Professor Matt always went the extra mile to make sure we were there mentally,” OB stated. “I’ve been trying to open my barbershop for the past year. As soon as I got into the program, I started looking around for a shop location. Even though it may have been a little premature, he always took the time to see places with me. He didn’t give me more doubts or fears; he was always there. He never said to me, ‘not now’ or ‘it’s too early in the program to start looking.’ He always encouraged me to continue.”

Brand new beginnings on Brown Street 

One day, when OB wasn’t actively looking for a spot to rent, someone told him about an available barbershop on Brown Street in East Hartford. Although the site needed some initial work, the next thing OB knew, he was being handed the keys, opening not only the door, but the power of his unlimited potential as well.

With further renovations including new floors, paint, and polish, OB proudly proclaimed the difference as “night and day! It’s all a big accomplishment.”

“My barbershop is sophisticated, clean, and inviting,” OB added. “Many people around Brown Street were getting right on the highway to Hartford for their haircuts, but now, when I cut their hair and give them the mirror, they’re smiling, and it makes me feel complete.”

“I am purpose-driven,” OB pointed out. “Down on Brown Street, there are low-income housing units, and God gave me this barbershop and this gift with a purpose to help out, and I look forward to being a part of this community.”

A community of contacts 

Through the ENet program, OB also experienced the positive power of networking. “Now, in my contacts, I have more numbers and resources of people doing great things, and that circle gives me a sense of responsibility,” the new business owner shared.

“The whole ENet atmosphere was a community, it was a like a family,” OB went on. “Everyone had their own style, their own thing they brought, and they all had something I needed.”

As for any advice for the formerly incarcerated considering the ENet program, OB offered, “push through and trust the process.”

“When I started the program, I knew I had potential,” he admitted, “but I didn’t know how much. I started thinking about who I was as a person, and for the first time in my life, I thought, ‘This is the type of man I want to be.’”

Potential turned professional

“OB joined the ENet program at Goodwin last year,” Matt Connell said. “Since day one, he knew exactly what he wanted to do and has worked tirelessly to accomplish his goal of opening his own barbershop. I have had a trim from him, and on top of being an amazing barber, OB is a talented, intelligent, caring person who is creating the future he has always envisioned for himself.”

“Because of the barbershop, I was able to stay out of the streets,” OB asserted. “And in the end, everything helped me to reach my goals and stay grounded.”

“I want people to know that, despite whatever disaster or trauma I went through, I was able to move forward in a way that helps others, even if it’s just one person, so they don’t have to go through the things I went through. I’m able to do that, one haircut at a time.”

Interested in learning more about the Entrepreneurial Network?
Contact Matt Connell at