This week we’re heading to the Tri-State area, where DRIVESHARE Pro Owner Jim has spent over thirty years building one of the most distinctive classic and luxury SUV collections on the platform.

From a 1971 Ford Bronco to a 2020 Range Rover Sport, his fleet has set the scene for fashion editorials, brand activations, family milestones and everything in between.

Tell us how it all started...

It started back in 1991 with my very first new vehicle: a 1991 Jeep Wrangler. That taste of freedom and capability hooked me immediately. Not long after, I upgraded to a 1994 Land Rover Defender, taking it off-road and exploring trails all across Colorado and Utah. By the turn of the millennium I stepped into a 2000 Range Rover, cementing my appreciation for vehicles that combine rugged utility with effortless style.

While my collection has evolved and changed many times over the years, I always find myself coming back to those same core vibes: authentic, iconic and purpose-built machines.

So, what's in your fleet?

The current fleet spans decades of boxy automotive design, split between vintage heritage and modern sophistication. On the classic side: a 1971 Ford Bronco, a wood-panelled 1990 Jeep Grand Wagoneer, a bright yellow 1995 Land Rover Defender 90 and a black 1997 NAS Defender 90. These deliver what I’d call that undeniable Old Money New England aesthetic and authentic rugged Americana.

On the modern side: a 2015 Mercedes-Benz G550 and a 2020 Range Rover Sport, for productions that need an urban-elite energy and a strong screen presence. Every vehicle comes with white-glove, owner-operator service on site to make sure everything runs smoothly from set call to wrap.

What kinds of bookings do you enjoy most?

What I love most isn’t just driving these cars — it’s seeing how each one becomes a character in someone else’s story. Over the years the fleet has been part of brand activations and editorial shoots for fashion labels and lifestyle lines, pop-up events and commercials across New York, Connecticut and New Jersey, and milestone family moments — from maternity shoots to families picking out their Christmas tree with a vintage Grand Wagoneer or Defender packed for the holidays.

I also often supply period-correct props alongside the vehicles: canoes, Schwinn bikes, camping gear, winter activity equipment. Whatever helps bring the scene to life.

How far do you travel with the cars?

I traditionally service NYC, Long Island, the Hamptons and the entire Tri-State area, but I’ve towed my cars from Maryland to Maine when the right booking calls for it.

What keeps you going after thirty years?

Seeing how others appreciate the collection only makes me want to keep expanding and adding to the fleet for another thirty years. That says it all, really.

Thank you, Jim, for sharing your story and being part of the DRIVESHARE community. You can explore the full fleet on DRIVESHARE, where Jim’s 1971 Ford Bronco, 1990 Jeep Grand Wagoneer, both Land Rover Defenders, the Mercedes-Benz G550 and Range Rover Sport are all available to book across the New York Tri-State area.

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