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Meet Jessica Del Leola of Cutting Edge 54 Salon / Sippin N Trippin

Today we’d like to introduce you to Jessica Del Leola.

Hi Jessica, it’s an honor to have you on the platform. Thanks for taking the time to share your story with us – to start maybe you can share some of your backstory with our readers?
I’ve been a hairstylist for ten years and owned my own hair salon… Cutting Edge 54 Salon for seven years. I’ve had people before always tell me to try out for these reality shows or I should come out with my own show (YouTube). I never paid attention and continued to be the loud, outgoing personally that I am.

One day, a client of mine Crissy Johnston introduced me to Maurice Proffit of B-side Studios. We laughed, joked and he asked me to send in my info for a Show they were coming out with called Wine, Dine & Go Live. Online Virtual Blind date. I told him I would do it as long as they don’t try and change me or filter my mouth. He said those were the reasons he wanted me to try out. So I did it and was picked to be on their Pilot show…

What I wasn’t ready for was the feedback. Omg… I couldn’t believe the feedback being so positive. People saying how they can relate or wish they could say those kinds of comments out loud.

If you know me, I’m a straight-up person. Where you will get the truth. I don’t have a filter. I try to make the best out of any situation and laughter is my go-to so everyone is comfortable around me.

So after the WDGL show I said you know what… Why not do my own show? Growing up in the “hood”… Being all over Chicago… Being a Hairstylist. I’ve heard so much… from all different ages… And ethnicities. Some ask for advise… Some just get my opinion anyway… Lol.

I grew up in Chicago and reside now in the suburbs. I’m a single mom to two boys. (15 and 5 years old)

With my background and my personality. I figured let’s do it. Mr. Proffit of B-side Studios got wind of it. Told him I was going to do my own podcast and he was on board to help out through the process.

SIPPIN N TRIPPIN was created. It’s a Chicago-based podcast keeping it true to the reality of Life. The show goes LIVE twice a month on Facebook, YouTube and other podcast platforms. I go All over the city and suburbs… Hosting it at different locations. Hair salons, barbershops & bars… Wherever we can get Internet access… Lol. Our guests range from Entertainment people to people who do 9-5.

After watching a show… I hope that it leaves a smile on ya face, maybe something to think about or a different view/perspective or even just to get away from your reality even for just an hour.

I always say… what can we NOT talk about… Life, love, current events, music, mental health, money… etc. Nothing is off the table.

* I love being able to express myself openly and unfiltered. Told my mom… finally. I’m in a space where my big mouth & big personality work in my favor. *

Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?`
I’m going into this blind. .

In regards to Sippin N Trippin. We have had issues with the quality of video, audio & lighting on some episodes. Also internet access to make sure we have a strong connection. Luckily my nephew Julian Gaytan is now my Tech guy and has been helping me get through these obstacles.

Now with Cutting Edge 54 Salon. . Same thing. . Went into the business aspect of it blind also. . I guess i like jumping into things and I’ll figure it out as I go.. lol.

I’m not one who likes the paperwork aspect of the business. . I like being in the front . . Customer service. It’s been trying but its never a lose but a lesson. . From learning about taxes, leases, insurance & money management. . Etc. I’ve learned a lot and still learning.

Its life . . Is anything ever really smooth? Roll with the punches and keep it moving.

Alright, so let’s switch gears a bit and talk business. What should we know?
I love being a hairstylist. The Connection with people. Helping them feel better about themselves. It’s not just about how they look. It’s their overall being. If I can get them to see the beauty inside of themselves. Then it’s a win win. With the podcast Sippin N Trippin. It gives me a different outlet to basically do the same. True believers in laughter is the best medicine.

What do you like and dislike about the city?
Oh my lovely city. . . CHICAGO or you’ll hear me say Chi-Town.
Its a love / hate relationship really.

I adore its authenticity. . Its realness. . Its acceptance. . Its history. . But in the same motion i hate it for all those same reasons. . Lol.

We have beautiful people. Culture. .scenery. . . . Omg the lakefront. And then the FOOD. . Please. I dont know any other city that you can find so many different things to eat. Lobster and steak to Gyro fries with cheese. If you havent ever had them . .your missing out.
BUT. .

We also have the crime, robberies. . the senseless killings . .politics .. crooks in suits. .drugs. racism. It just seems like its getting worse.

I’ve lived in the suburbs for some time now and i always say my address will never say Chicago ever again but the love I have for my city remains the same.

We just have to get back to Respecting Humanity. Each other. Respect for ourselves. Our kids. Our elders. . We are all people. . We all bleed. We all need Love.

Contact Info:


Image Credits:

Paulina Fadrowska

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1 Comment

  1. BARBIE GIRL

    October 21, 2021 at 20:28

    MISS YOU GIRL~~ STILL LOOKIN FLY AS ALWAYS!! WE NEED TO CLICK UP NEED MY HAIR DID!!!! <3 *BARBIE gIRL*

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