Uploaded July 2026 | Updated September 2026, 1 week ago
Brad Oleshansky spent over a decade as an entertainment attorney in LA — working around Disney, Virgin Records, and the company behind the infamous McDonald's Monopoly scandal (yes, the HBO "McMillions" one). Today he's the founder of The Motor Enclave, a $150 million, 200-acre automotive destination outside Tampa with a Formula 1–caliber Tilke-designed track, a 100-acre off-road course, and 300 private garage condos that sold out before a shovel hit the ground.
In this episode of Cars and Culture with Jason Stein, Brad breaks down how he turned "racetracks don't make money" into one of the most successful private car club models in the world — by flipping the business on its head and renting the track to industry instead of racers. He shares why he pre-sold his way to $130M in funding during COVID, why his average member is a 55-to-60-year-old who's "never done anything," and why the whole thing is about community and camaraderie, not car storage.
Chapters:
0:00 — Intro
2:26 — From Disney Lawyer to Racetrack Builder
7:38 — The McDonald's Monopoly Scandal, From the Inside
9:09 — Building & Selling a Company to Meredith
13:20 — "Car Guy, Not a Track Guy" & the Woodward Nostalgia
17:19 — Flipping the Racetrack Business Model
21:17 — Who Actually Joins the Club (It's Not Who You Think)
23:57 — Why Tampa & the $150M Bet, Funded With No Bank Loans
33:54 — Why an F1 Designer + the Events Business
42:53 — Expansion, Europe & What's Next
One of the most fascinating conversations we've had in 259 episodes.
🎙️ Cars and Culture with Jason Stein — airing on SiriusXM.
#CarsAndCulture #MotorEnclave #CarCulture #BradOleshansky #JasonStein #Tampa #F1 #Hypercars #CarCollector #Motorsport
Brad Oleshansky spent over a decade as an entertainment attorney in LA — working around Disney, Virgin Records, and the company behind the infamous McDonald's Monopoly scandal (yes, the HBO "McMillions" one). Today he's the founder of The Motor Enclave, a $150 million, 200-acre automotive destination outside Tampa with a Formula 1–caliber Tilke-designed track, a 100-acre off-road course, and 300 private garage condos that sold out before a shovel hit the ground.
In this episode of Cars and Culture with Jason Stein, Brad breaks down how he turned "racetracks don't make money" into one of the most successful private car club models in the world — by flipping the business on its head and renting the track to industry instead of racers. He shares why he pre-sold his way to $130M in funding during COVID, why his average member is a 55-to-60-year-old who's "never done anything," and why the whole thing is about community and camaraderie, not car storage.
Chapters:
0:00 — Intro
2:26 — From Disney Lawyer to Racetrack Builder
7:38 — The McDonald's Monopoly Scandal, From the Inside
9:09 — Building & Selling a Company to Meredith
13:20 — "Car Guy, Not a Track Guy" & the Woodward Nostalgia
17:19 — Flipping the Racetrack Business Model
21:17 — Who Actually Joins the Club (It's Not Who You Think)
23:57 — Why Tampa & the $150M Bet, Funded With No Bank Loans
33:54 — Why an F1 Designer + the Events Business
42:53 — Expansion, Europe & What's Next
One of the most fascinating conversations we've had in 259 episodes.
🎙️ Cars and Culture with Jason Stein — airing on SiriusXM.
#CarsAndCulture #MotorEnclave #CarCulture #BradOleshansky #JasonStein #Tampa #F1 #Hypercars #CarCollector #Motorsport
