To quote the film Talladega Nights: The Ballad of Ricky Bobby, “America is about speed. Hot, nasty, bad ass speed.” Well, as Diane Caplan can attest to, those high-octane values are still alive and well in 2024.

Diane — who is a native Texan — currently serves as the Head of Marketing and Brand Management for Post Oak Motors. She is a hypercar aficionado with many years in the luxury automotive space under her belt.

Caplan has the sort of supercar experience that most can only dream about. Still, she has earned her spot every step of the way. All said, it is quite unlikely that you’ll find an individual more knowledgeable on elite manufacturers such as Bentley, Bugatti, Hispano Suiza, Lotus, Rolls-Royce, Zenvo and others.

Amidst an incredibly active work schedule, Diane set aside 30 minutes to talk with Playboy’s Gabriel Santiago across a variety of automotive topics. As a surprise, Caplan alludes to her prior experience posing for Playboy!

Playboy: Let’s start at the beginning—where are you originally from?

Diane Caplan: I grew up in Deer Park, Texas. It’s a suburb about 30 minutes outside of Houston. I also lived in Chicago for several years and then came back to Houston around 2008.

Playboy: How did you initially fall in love with motorsports?

Diane Caplan: When I was a kid, I had more Matchbox cars than I did Barbie dolls. My dad had old Mustangs and I was always by his side when he was fixing them. It was sort of  in my blood. I’ve always loved cars, especially the freedom that cars give you. I’ve always been enamored by automobiles ever since I was little.

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Playboy: Fast forward to now and you’re on top of the supercar game. Tell me about what’s going on at Post Oak Motors?

Diane Caplan: A lot and a lot very quickly. Our owner Tilman Fertitta, who also owns the Houston Rockets, recently formed Fertitta Automotive. Right now, we are in heavy acquisition mode, actively loading up both on domestic and on luxury opportunities. As always, we love our luxury brands in Bentley, Rolls and Bugatti, and we just purchased our first domestic store, Fertitta Chevrolet.  We have our sights set on expanding our exotic car segment, so we are always on the lookout for new up-and-coming brands. We’re ready to take on the whole country.

Playboy: What is it about British manufacturers like Bentley and Rolls-Royce that sets them above the rest?

Diane Caplan: Bentley and Rolls-Royce, in my opinion, stand unparalleled in the automotive world. Their bespoke offerings are truly exceptional. Rolls-Royce allows you to create one-of-a-kind vehicles tailored to the most personal specifications. Meanwhile, Bentley, one of the oldest coachbuilders in history, showcases its unparalleled craftsmanship through its Mulliner division. The level of customization and handcraftsmanship from both brands is simply unmatched.

Playboy: I see you have an affinity for roadsters. What’s your impression from the Bugatti Tourbillon, and how does it compare to the predecessor Chiron?

Diane Caplan: I never thought that they could trump the Chiron because, to me, it’s the most beautiful, most perfect car. During some private viewings that we had with previous Bugatti clients, they revealed the Tourbillon! The level of design and engineering is immaculate. I could literally sit in a room all day long and I would never get tired of staring at it because I would find some other new angle or some other detail that I didn’t catch when I looked at it for the previous two hours.

It really set the bar for hypercar companies out there. I can’t wait to start seeing these on the road. I’m so excited. We’ve had a couple of clients that visited Formula 1 in Las Vegas last weekend that took their Bugattis.

I’m more excited about the future of Bugatti and all of the exiting projects they have in the works. The stars are very bright for Bugatti.

Playboy: Care to share any stories from Concours at Wynn Las Vegas?

Diane Caplan: It was my second year and I’m going to make that a yearly thing from now on. It’s very reminiscent of some of the things from The Quail at Monterey Car Week, except on the smaller level. There’s still plenty of room to grow, for sure, but it’s a young event. It was very accessible and the VIP ticket was well worth it. It came with my stay at Wynn Las Vegas. I pretty much relaxed, drank and hung out with beautiful cars all weekend. I would highly, highly recommend it.

Playboy: Can you tell me about your experience as a female thriving in male-focused industry like automotive?

Diane Caplan: I’ve been in the car business for over 25 years now. When I started, I was one of the only women at the dealership. I started a Mercedes store. Back then, we couldn’t even wear pants—women weren’t allowed to. Can you imagine that?

There’s always going to be people trying to patronize and make you feel like a little lady, but what has helped me is that I have tough skin and I’m extremely passionate about cars. Also, I don’t let anybody stop me from doing what I want to do.

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I am a tomboy at heart and have always been comfortable hanging with the guys. I simply learned to stand my ground, dish back what they would dish out and it always seemed to diffuse the situation.

I’ve been very lucky however, as I’ve had amazing mentors along the way in my automotive career that were men. They recognized my intelligence and talents, helping me rise to the top very quickly. But it’s a tough business and it’s not for everyone.

Playboy: I hear you have prior experience with Playboy! Care to tell me about that?

Diane Caplan: It was 20 years ago this November that I was in the magazine! I lived in Chicago and one of Playboy’s senior photographers walked into my car showroom, saw me and handed me his card. He said, “You should pose,” and I started laughing! Still, we made it happen. It was one of those things that I always wanted to do. Playboy is Playboy! I thought it was an honor and I’m glad I did it. It’s something fun for me to look back on as I get older.

Playboy: Going forward, what should Playboy readers be on the lookout for from you?

Diane Caplan: A ton! You better stay tuned to my Instagram because it is going to be nonstop. We travel so much with our clients, doing events and other things. We’ve partnered with The Exotics Network, which is a supercar group out of Austin. We’re going to be traveling around the globe with them.

For instance, we’ll be doing a rally leading into Las Vegas Concours next year. Then, we’ll be doing a second rally with them from Sonoma to Monterey, so you’ll see all kinds of craziness that we get into with Exotics Network. Obviously, we’ve got our own private events. We’ll be at the Goodwood Festival of Speed, taking different clients there. We’ll also be at Monterey Car Week like always.

Then, my boss Lonny and I are finally launching My Supercar World podcast. It’s going to be very fun. We have such amazing clients and we get to interact with so many amazing car designers and presidents of these car companies. Why not utilize those perspectives and give real insight into this amazing culture?

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