CEO Connect: Brad Oleshansky talks about his pursuit of a vision

Brad Oleshansky has had more careers than most. He went to film school, law school and even represented Los Angeles rappers in the 1990s. 

He has worked for Disney and Simon Marketing, which ran the Monopoly promotion for McDonald’s during a scandal in 2000. 

He built his first “experiential automotive destination” in Pontiac, Michigan, called M1 Concourse. 

Now, as founder and chief executive officer, he’s building The Motor Enclave, in Tampa, a $150 million, 200-acre “playground” for those who share his passion for cars. 

Read Oleshanksy’s Cover Story from October 2022 here. 

With 167 units sold on a preconstruction basis, to date, representing $115 million in sales, it’s expected to be another winning business model for Oleshansky.

Bridgette Bello, publisher and CEO of Tampa Bay Business and Wealth, interviewed Oleshansky in front of a live audience, at the Dugout Club, at Steinbrenner Field. This transcript has been edited for length and brevity.

See photos from Oleshanksly’s CEO Connect here. 

So, Mr. October 2022—because we have other Mr. Octobers in the room from previous years—talk about what it’s been like for you having been on the cover of TBBW for the last 25 days?

Well, it’s been a phenomenal experience, of course. It’s mostly just great to hear from people that read the story and are surprised to learn about someone they’ve done business with. We have 267 customers that have, fortunately, bought these garages from our team, and they don’t know anything about me. Then they read the story and said, ‘I had no idea, I thought you were a real estate developer your entire career.’ I know nothing about real estate except this idea I had and, by brute force, had become a real estate developer and learned a lot about that, but it wasn’t an intended career path at all. The best impact was hearing from people that read the story and had no idea—because when you meet with people every day, you don’t tell them your life story. It was a good experience…

I just wanted to say, before I forget, TBBW has been a great asset for me. I don’t advertise our business. I always say it’s a word-of-mouth business. Being new to Tampa Bay, I didn’t know anyone here—we had to network and I wanted to create some buzz. Everyone in town told me, ‘You’ve got to talk to Bridgette! You’ve got to meet Bridgette!’ I thought, ‘Who is this Bridgette person?’ [Bridgette] convinced me to advertise, which is something I don’t generally do. We secured the back cover, fortunately, and we were on it for about a year. It was a huge catalyst for a lot of our salespeople. People read this magazine, it gets in the hands of the right people, and [Bridgette’s] not paying me for this pitch, by the way. I’m not a current advertiser—it served its purpose for what we needed then and we will probably advertise in the future. It was a one-year run and it helped drive the momentum for us. I owe a lot to TBBW as a great entrance into the market for general awareness of what we’re doing.

Often, some exciting things happen in between when we sit down with our cover stars and when we have this conversation. You have some pretty big news to share that I’m excited about, because you’ve been a great partner and so has the person or the company that you’re going to announce the news about. So, tell the people in this room something that they don’t know and no one else knows yet.

We just signed a multi-year deal, with Morgan Automotive Group, to be our official auto partner. Morgan will not only have a presence on our site, but they’re also going to have naming rights for the Jerry Ulm off-road course. Jerry owns the largest Jeep dealer in the nation, which is a perfect fit for us. They’ll also have an on-site speed shop, doing car repairs, oil changes, tires, brakes and all kinds of other services our members would want plus our own fleet vehicles. 

Brett Morgan and Larry Morgan embraced the idea. Originally, they didn’t quite understand it. Most dealers didn’t really get it because it’s not part of the traditional model. It took spending a day with Larry for him to really bless it. 

One of the things you said that you’ve heard since the story was published is people reaching out to you about your pivot, and doing your passion project, and then asking for your advice—how you did it. We always like to try to give some exclusive content and advice at these events. What would you tell people who sort of think you’re crazy and sort of want to be you?

My son is here, who just graduated college, so he hears this from me every single day. He’s probably sick of it and about to hear it again. I wish I would have done this earlier in my career. You know, when you’re in your 20s and you don’t have a family, you don’t have a mortgage, you know the risk, there’s not a lot of risk. Sure, you got to pay your bills or pay your rent. But if you fail in your 20s, it a lot easier before you got a lot of other people to take care of and expenses. 

I knew we were going to have too much fun talking and I had so many things that I wanted to go through. I really wanted to talk about the McDonald’s fiasco.

It’s called McMillions on HBO. Unfortunately, I was the lawyer for the company when the company went down. But it was one employee who brought the company down. And we were all exonerated. I did not steal the Monopoly game pieces. But it’s a great story.

But there’s something cool that you learned because of the story. And, you know, all roads seem to lead to Tampa. Talk about the connection to Tampa with the McMillions disaster.

It’s, honestly, like all roads in life. You know, when you build a big network, I tell my kids and I tell a lot of young people, business success is 100% networking. If you don’t meet the right people and work to nurture your network, all the time—that’s the key to my success. So, I was in, I got invited to go to Dallas. I’m not a football fan. But I went to the [Tampa Bay] Buccaneers game in Dallas with a bunch of people that own suites. I’m not a suiteholder. I don’t go. I know nothing about sports. But I was in Dallas, I met the Caspers—Blake and his sister. And I knew that they were formerly in the McDonald’s business and I said we have something in common. I said I worked for Simon Marketing. His face dropped. He’s like, ‘You must be a criminal’. And I’m like, ‘No, I worked there during the debacle,’ it’s a billion-dollar company, by the way, that got brought down overnight. It’s a great HBO special by one employee who was stealing the game pieces and selling them to criminals to redeem the prizes. The free house and free car. And he said to me, that’s crazy. I remember that time as a McDonald’s operator. But the crazier part of it is, I know Alan Brown (CEO of the company.) So how do you know Alan Brown. He goes, my father introduced Alan to McDonald’s. That’s how Sam Morgan got into McDonald’s. So just bizarre. I mean, it’s, it’s crazy. Everything comes full circle. 

You were in search of a 1923 Model T hot rod when we did your interview and you talked about some of your best memories being associated with that car and it’s a hell of a story how you got where you got, so try to shorten it for everybody in the room. He’s obsessed with finding this car. If you guys know this guy, Brad might write you a check, right?

The quick story is my dad built this car in our garage. It’s how I got into cars. It was a 1923 Model T. They’re called T Buckets. They’re very famous cars, there’s 1,000s of them that people built in their garages. And I drove around with my dad as a kid in this car. My dad was always about going for the drive in the car or when I got older was like, polish the chrome for 12 hours and I’ll let you go for a drive in the car. So this car is lost. He sold it in the in the early ’80s. 

I always look for the car, at shows, but never saw it again. I assumed it was gone. My dad’s 84 years old now. And my dream is to give him this car and he loves what I’m doing in the car business. But he’s gotten rid of all his cars. He can drive but he’s like, I don’t want to deal with all that stuff. So, I’ve been trying to find this car and I’ve tried looking forever. There’s a show in Detroit called the Woodward Dream Cruise. It’s in August. It’s the largest car event in the world. There are 65,000 classic cars on this road called Woodward. 

I went back to Michigan and went to the event. Didn’t see the car. And the next day one of my clients in Michigan sends me a picture and goes, this looks like your dad’s car. It was my dad’s car! And it was on Woodward and I missed it. My son knows how to do all the stuff that I have no clue how to do. He used Google Image match, or something. Scans the photo, finds a match on a dating site of this guy’s face. It says he lives in Royal Oak, Michigan, which is like 10 minutes from where we live. Then we used this other site, where you can look up people’s addresses you can pay $50 for people’s backgrounds, whatever. And we found an address. Well, Sam went to this guy’s house. And an old guy answered the door and my son’s like, ‘Do you have a 1923 T?’ and the guys like ‘I don’t like cars. I don’t like noise.’ so it was a dead end. 

So, anyway, I put it on Facebook. There’s like all these car page, on Facebook. There is a T Bucket group, there’s a Woodward Dream Cruise group. I put on the picture of the guy in the car on all these different groups on Facebook, I say I’m looking for this car $1,000 reward if anyone can point me in the direction of the owner. And within two days, three people said, ‘Oh, I see—what’s his name? I can’t remember the guy’s name—“Joe” at every car show. And, you know, here’s his name on Facebook and whatever.’ I messaged the guy, you know, private message, the guy on Facebook and he responded. And his first response was, I’m not selling the car, because he saw the posts, and I was like, I want this car. I’m always playing hard to get and you know, it’s going to be a negotiation for the car. Turns out the real story is, the guy, who’s probably in his 50s, doesn’t own the car, his dad owns the car and he uses the car as his pure enjoyment, and he can’t afford the car. And he knows that if I get to the father, I’m going to buy the car. He will not give me the father’s info. The deal is not done. We are in the process of trying to get to the father, which we will.


TBBW’s “CEO Connect” series is an exclusive, invitation-only, event that brings together the Tampa Bay area’s top business leaders to meet and mingle. CLA, Seacoast Bank, Questmont and Corex Legal were presenting sponsors. The host sponsor was  Steinbrenner Field.

TBBW’s video partner is Empowering Creative.

The evening begins with a cocktail reception for about 120 guests, followed by an interview with that month’s cover CEO.

Partnering with TBBW on future editions provides an opportunity to network with the area’s business elite, generate new business opportunities and increase brand awareness.

For information about event sponsorship opportunities, email Jason Baker at [email protected].

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