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Start It Up! It’s Only Entrepreneurship…But She Likes It

By Jonathan Kersting

It’s never a dull moment whenever I hang out with Denise DeSimone. There’s always something new cooking in her business life and I’m often, as luck would have it, privy to inside information before anyone else in Pittsburgh knows it.

If you don’t know Denise, she is THE definition of an entrepreneur. But not just any entrepreneur. An entrepreneur with Keith Richards sensibilities. I say Keith or “Keef” because Denise is pretty quiet, almost unassuming, but her business sense plays like a Telecaster guitar tuned to open G bleeding through a screeching-hot tube amp.

If you don’t know the Stones or Keef, this may be lost on you. And for that I am sorry. (Go listen to Sticky Fingers and come back to this article with a new understanding.) Denise and I are both soulmates when it comes to the Stones. Simple as that.

Denise has seemingly countless tech and business ventures under her thumb and is currently spinning many at the same time. Most people in Pittsburgh know her as the founder of C-Leveled. However, Denise first found success building and selling companies back in Memphis, Tenn. She left her native Uniontown after college at Pitt to take a stab at an architectural railing company with her uncle.

“I was like, I’m not sure I even know what architectural railing is. And I know I can’t read a blueprint. So, why not go to Memphis and start this business?” said Denise. “We did well, and it was different because I had to learn so many new things. I was an English major. And you know, there was nothing about any of this that I knew. We started that business. And then we grew it. And then a couple years later, we ended up selling it.”

A string of successful business launches and sales brought Denise back to Pittsburgh to be closer with her family. But, she had no intention of starting or buying another company.

“Well, I came back to Pittsburgh, and I said, ‘I’m never going to ever have another company.’

“I was going to just, you know, do some consulting,” she said. And at about that time I met Denise at the Tech Council. I think she was consulting for Advanticom at the time. I don’t remember the context of the meeting, but I do remember knowing that she commanded the room and her business smarts were off the charts. I took note!

After a few years of consulting, Denise saw the need for C-level executives as a service and got the itch to dust off that Telecaster to play entrepreneur again at the sweet spot of the neck.

“It was really during that time that I thought about C-Leveled, because I was thinking there’s a need for a high-end CFO or COO. But, I wish I could just pay by the glass. I started thinking about it, and I started realizing that over the course of my whole career that it’s the entrepreneurial scars that will kill you. So, it’s like, if I would have been able to reach out on certain occasions to different people, it would have made my life and, you know, probably the businesses a lot better, and so it started really kind of resonating at that point. In some ways Advanticom was my first customer.”

Apparently about a year after that realization, I got an email from Denise. “Hey! Meet me at the Starbucks on Copeland in Shadyside tomorrow. I’ve got something to show you. How about 8?” My interest was piqued. She was playing it Keef cool for sure. I couldn’t wait to see what she was cooking up her sleeve.

She laid out her plans for what would become C-Leveled. She opened her laptop, flipped it around and walked me through the website and how it would connect top-level executive talent to startups and other businesses in need, but not ready for a full-time hire. I, myself, readily saw the need in the startup market and was pretty stoked to see how she would launch and build this business. She wanted my insights, reactions and thoughts on ways to start getting this out to Pittsburgh’s tech ecosystem.

I knew it was going to fly and Denise was the woman to do it. Years go by. I can hardly keep track of all the partnering the Pittsburgh Tech Council has done with C-Leveled. I can’t keep track of the radio shows, happy hours and marketing plans. I use this term a lot, but C-Leveled was a sixth Stone to the Tech Council, if not Jimmy Miller himself producing the music.

C-Leveled evolved over the years getting a little black and blue along the way. Denise kept firm and led C-Leveled through tricky times to find itself evolve into one of Pittsburgh’s top digital marketing agencies.

A few years ago, Denise texted me to meet for a beer and our favorite buffalo cauliflower wings at the Church Brew Works. I had a feeling she was going to tell me about her next venture. I was not wrong. This time she sprung it on me that she and her business partner bought Steel City Con. What??? For real? Yep. She didn’t know the first thing about Star Trek or Buffy the Vampire Slayer, but she saw an awesome business opportunity.

“I mean, I don’t even know all these celebrities…I kind of look at them, like you are you. I’m not starstruck. I’m like, ‘No, that’s a SKU number.’ Yeah. It’s cute. And, you know, that’s kind of how I look at it. They are inventory that I’ve got to move!”

So I asked Denise about her favorite piece of inventory. She said Meatloaf was one of the nicest celebrities to attend Steel City Con.

When I first dreamt up the PGH Tech 25 Series, Denise was immediately tops on my list of people that I wanted to write about. Back in March, I was stoked to meet up with Denise and interview her. I had only seen her a few brief times during COVID.

Before I turned on my recorder, Denise said that she had something to tell me. I was thinking, oh cool, another new business. In her usual, matter-of-fact tone she dropped a bomb on me. “I’ve sold C-Leveled,” she said. What??? Are you serious??? I had to let this sink in, do a double take.



“It’s just time. I want to pursue some other ideas and I think a new owner will be able to take it to a new level,” she said. I kept thinking about the trials and tribulations, the ups and the downs, the building something really cool. How could you just sell it? Almost like walking before they make you run? Nah. Like any venture, it has an arc. Denise can take full comfort knowing that she built an amazing business and will let it go to grow to a whole new level.

I can respect that and there are only so many hours in the day. Time is not always on our side here! A rolling stone doesn’t gather moss, so she’s ready to open up some space to create more time and energy for new ventures.

I feel as if I’m ending this story where it began. Hanging out with Denise, getting a little inside news before anyone else; albeit a bit shocking! After all, it’s only entrepreneurship…and we both like it. Damn, I can’t wait to get my next text from Denise…