How Winston Reed Built Cut Right Barber & Beauty From Sheer Drive

“What brought me to this location? Vision,” says barber and entrepreneur Winston Reed

Winston Reed cutting hair inside Cut Right Barber and Beauty, the shop he owns in West Garfield Park. | KENN COOK JR.
Barber Winston Reed. | KENN COOK JR.

I interviewed Winston Reed, 37, the owner of Cut Right Barber and Beauty at 811 S. Pulaski Rd. in West Garfield Park on Nov. 7. He was getting ready for a community feeding he planned to host just three days later. Reed’s energy is what his shop’s name promises — sharp, focused, and grounded in purpose. 

I always tell people the same thing: the secret to my success is determination, drive, and hustle. You’ve got to have a vision, and then you’ve got to attack it. Attack the vision. That’s what I did.

I show people this tattoo on my arm. One of my first ones. It’s the shop name — “Cut Right.” I got it back in 2014 or 2015, before any of this existed. I was building the brand even then. I used to post “Come get cut right” on Facebook, and that’s how it took off. I set out the vision early and stuck to it.

I went to Westinghouse Career Academy, and honestly, I don’t know where I’d be without their barbering program. That school gave me direction. It gave me a skill. When I came out, I knew I had something to build on. So I built the brand first — before I had a shop, before I had a location, before any of this.

People ask if the shop is profitable, and yeah — it is. This brand is marketable. But it didn’t come easy. I tell everybody: you get out of life what you put into life. I’m not big on spirituality — I’m big on suffering, on pushing yourself. Everything I do, I beat myself up to do it better. I’m real self-motivated. Always have been. Nobody had to tell me to get up and do something, not even when I was a kid.

Winston Reed shows off the tattoo that depicts the name of his shop. He said he got the tattoo long before he opened the shop. | KENN COOK JR.

What brought me to this location? Vision. But also necessity. I was already thinking about moving, and then the barbershop I was working at got shot up. A couple kids got hit while I was cutting hair. That was Jan. 16, 2020, right down the street on Pulaski. That changed everything and pushed me harder. 

My clientele went down after that, but I never quit. I never folded. I found this space, tore it down, remodeled it, and built it back up myself. I had to. I was forced to find somewhere else to go, but it ended up putting me right where I needed to be.

By Thanksgiving of 2020 — the first year in this new shop — I fed 400 people. That was just the beginning. Every year since, I’ve done something for the community. Because what’s the point of building a brand if you’re not lifting up the people around you? 

About ‘The Grind’

From barbers and bakers to tech founders and corner-store owners, The Grind explores how West Side entrepreneurs are redefining what it means to build something lasting. Each installment profiles local innovators whose businesses strengthen the fabric of Austin, North Lawndale, Garfield Park, and beyond — creating jobs, community spaces, and new possibilities. Through their stories, The Culture chronicles not only how people work, but why they keep grinding for the neighborhoods they call home.

If you know a business or social entrepreneur you want us to profile, send us a tip at stories@ourculture.us