Q And A: Raynie Jackson, Owner of Headrest Barbershop

Raynie Jackson, Owner of Headrest Barbershop
Raynie Jackson, Owner of Headrest Barbershop -Photo courtesy of AndrewCFowler.com

Chicago based entrepreneur Raynie Jackson is the epitome of the classic ‘making something from nothing by pulling yourself up by the boot straps’ story.

Now the owner and sole proprietor of HeadRest Barbershop, located on the corner of Michigan Ave. and Harrison St. in downtown Chicago’s Congress Plaza Hotel, Jackson stands as a father figure to his clients and employees and in some ways even an ambassador to the city as his shop’s prime location frequently plays host to visitors from all over the world.

N’Digo recently sat down with Jackson to discuss his humble beginnings, the importance of the barbershop to the black community, and what he thinks of our new President-Elect.

How did you get your start as a barber?

I got my start by cutting hair in my Grandmother’s basement in Ford Heights. She had a single family home so myself, my uncle, and my cousin, we converted her basement and started cutting hair down there. We were good barbers but we just hustling and trying to make extra money. My uncle actually had the foresight to think bigger. He came up around barbers but never took the next step of owning a shop. So he had a vision for the shop and it manifested right there in my Grandmother’s basement. But then after a while it became too popular and we couldn’t really stay in the basement. People would be lined up outside and sitting on the stairs waiting for their turn to get cut. It became too overwhelming so we had to find a bigger place and ended up finding an old laundromat and made that our new shop.

How did things for progress from there?

After that I got married and moved to the city and I really wanted to do something that was a bit more than your typical neighborhood barbershop. I never really had an idea of what that could be until my Uncle moved downtown and opened up a club down here called “Network”. I would go there and cut his hair and some of the staff members as well. One day I was there and a patron came in and was telling me about a spot that was looking for a licensed black barber. I went in and interviewed without giving it too much thought but they hired me on the spot. That was almost 20 years ago. I stayed there for about two years before I left to open up my own shop. From there we moved locations a couple times until I found this spot here at the Congress Hotel and I’ve been here about seven years. Took about six months of lobbying and politics before we could close the deal.

Raynie Jackson, Owner of Headrest Barbershop -Photo courtesy of AndrewCFowler.com
Raynie Jackson, Owner of Headrest Barbershop -Photo courtesy of AndrewCFowler.com

What’s the importance of the barbershop in black neighborhoods and bringing that atmosphere to a downtown location?

The black barbershop has always been a pillar of the community. We have a very unique appeal because of our location but our shop is still that place to come talk sports, come get stuff off your chest, have a dialogue with your peers, talk politics and current events, etc. We’re still that place. For us it’s unique because we’re not just that to black people now. Now we’re that for all nationalities. With our new location (on the corner of Michigan and Harrison) we’ve literally had people come in from all over the world. I’m talking Germany, Italy, Switzerland…and some of these people have never seen a real barbershop before. They’ve seen some of the big chains, but they’ve never seen or been in a real old school barbershop.

In your opinion, how accurate are movies like the Barbershop series in depicting the true essence of your typical neighborhood barbershop?

If I’m being honest, I have to say I never really liked the Barbershop series too much because it feels like a movie. And I’m sure they’ve taken some parts and some actual happenings and incorporated that into the movie, but it never really felt real to me. I don’t like barbershop movies overall, not just that one, but I don’t like them too much overall because to me they never really depict the relationships between the barbers, the shop owners, and the customers.

As someone who is a integral part of the neighborhood, what’s your take on the violence plaguing areas of the city and the distrust between our community and the police?

Man that’s really a multi-faceted thing. There are a lot of factors at play when it comes to the violence. First, we need more accountability from the alderman, the police captain, and the officers walking the beat. Secondly, you have to remember that these are impoverished communities. A lot of these crimes are rooted in poverty. I’m from the projects so I’ve seen this firsthand. I know the feeling in the air of there being no way out and what it’s like to literally feel handcuffed to that situation. And lastly, and this should actually be first, but education is the key. These kids lack an understanding on how things are supposed to be. And you can add on to that the fact that the family unit has been broken up in our communities. A lot of times by outside forces. For instance in the 60’s and 70’s families were not able to get public assistance if a man was present in the house. So that puts the father figure outside of the house. Plus war and incarceration…all these factors add up. What you see today is the end result of stuff that happened 40 and 50 years ago.

What, if anything, has been your biggest lesson learned since opening Headrest?

Raynie Jackson, Owner of Headrest Barbershop

I’d probably say the it’s two-fold for me. One, the importance of not spending your money as soon as you make it. There’s something to be said about saving your revenue and creating a nest egg for yourself. Also, it’s not always what you know, but WHO you know. That’s a very underrated statement. I think that’s something that people in our community don’t always understand. Some connections that you make can carry you throughout the course of your life. I’ve bonded and made connections with people in high school who went on to be very influential in the city and those connections have helped me to this day. When you want to get things done and you know people in positions to help you get those things done, it makes things a lot easier. You can have the knowledge of how to do it, but you cant get your foot in the door because you don’t know anyone. So you gotta open your circle up and meet people you can lean on in certain situations and become someone they can lean on in certain situations.

At the end of the day, what motivates you to do what you do?

It’s family first for me. I just want my family to be proud of me and say “Well done!” I also feel a need to help be part of the solution to the things that negatively affect our community. If someone that comes through my shop whether it be a barber or customer can pick up gems that’ll help them in their life then that’s what I’m here for. I’ve always tried to have a business where people learn how to produce, and understand economics, and learn how to take care of themselves and uplift and build up their community.

What are your thoughts on our new President-Elect?

I don’t know what to make of him. He’s so unpredictable you just never know what he’s gonna do.

What’s something your clientele would be surprised to know about you?

People would never guess in a million years how deep my roots are in Chicago Hip-Hop. No one will know how far down that tree my roots are planted.

Best advice to aspiring barbers or entrepreneurs?

Create a business plan. Keep it close to you like the Bible. Go over it weekly. Make sure you’re on track with your goals.

Favorite quote or affirmation?

“Education is the passport to the future” – Malcolm X

What’s next for Headrest Barbershop?

img_8582I want to open a barber college but I want it to be different. A lot of barber colleges are just mills that make money. They dont actually care about the barbers they graduatieI don’t agree with but I can understand why they do it. I think our culture can be better served and produce better products and barbers. That’s what’s next for Headrest. We want to get a school next year. I also plan to run to be a board member on the Barber’s state board. Believe it or not, there are no barbers on the Barber’s state board. It’s just beauticians and to me that’s crazy. To have a barber’s board and no actual barbers on it? Those are my immediate goals to put those things into place and with God’s will, by next year a lot of those things will come to fruition.

Headrest Barbershop is located at 520 S. Michigan inside the Congress Plaza Hotel on the corner or Michigan Ave. and Harrison St. Walk-ins are always welcomed.

For more information on Headrest please call 312-588-1287 or visit Facebook.com/headrest.barbershop

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