This Side Hustle Spotlight Q&A features 52-year-old Shawn O’Connell. O’Connell is based in the Bay Area and rents out his classic Mustangs with DRIVESHARE. Responses have been edited for length and clarity.
Image Credit: Courtesy of Shawn O’Connell
What was your day job or primary occupation when you started your side hustle?
At the time, I was working as a sales leader for a technology company. It was a steady job, but I’d always had a love for classic cars, thanks to my dad, who owned and restored vintage vehicles. So, when I inherited my dad’s Mustang, I wanted to find a way to use it rather than just letting it sit in the garage. That’s when I started looking for opportunities to rent it out.
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When did you start your side hustle, and where did you find the inspiration for it?
The inspiration came during the pandemic in 2020. My wife and I were trying to rent a car for a trip to Phoenix, but due to Covid and the wildfires, there were no cars available. That’s when we came across a peer-to-peer car rental platform where individuals rent out their personal vehicles. The owner met us at the airport and handed us the keys — it was cheaper and more convenient than the typical rental car agencies. It was brilliant, and the experience got me thinking: Why not rent out my Mustang? I decided to list it online, and within 24 hours, we had six bookings. It took off from there, and I realized there was real demand for classic cars like mine.
Image Credit: Courtesy of Shawn O’Connell
What were some of the first steps you took to get your side hustle off the ground?
First, I researched the platforms where I could list my car. I started with a couple of peer-to-peer car rental platforms, including DRIVESHARE, which is now the main platform I use. I also took the time to understand how insurance would work and what kind of pricing made sense for a classic car rental. In the beginning, it was all about making sure the car was in great shape and figuring out logistics for deliveries and pickups. Since classic cars have a different appeal than modern vehicles, I focused on ensuring the car was aesthetically pleasing and clean, knowing it would be used for events like weddings or photoshoots.
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What were some of the biggest challenges you faced while building your side hustle, and how did you navigate them?
One of the biggest challenges was managing my time. Between working full-time and running this side hustle, there were moments when I had two cars booked at once and had to juggle customer communications, deliveries and maintenance. Pricing was another early challenge. For events like weddings or photoshoots, I wasn’t sure how much to charge at first, but the DRIVESHARE platform is easy to use, which helps, and they also have online guides and good customer support. Now, when managing multiple bookings, I’ve got my sons involved during the summer, and I’ve become better at planning and adjusting my schedule around busy periods.
Image Credit: Courtesy of Shawn O’Connell
How long did it take you to see consistent monthly revenue? How much did the side hustle earn?
Within the first few months, I started to see steady bookings. My goal at the beginning was to cover the car’s maintenance costs, but it quickly became more than that. In the first year, I brought in between $24,000 and $30,000, depending on the season.
What does growth and revenue look like now?
I added a second Mustang to my fleet in 2022, and in 2023, a third due to the high demand. My cars are often booked months in advance, particularly for weddings and other special events. We do a lot of music video shoots and commercial work as well, and those bookings often come through DRIVESHARE. During the wedding season, I’m booking three to five events per week, and we’ve had clients refer us to friends and family, which has helped us grow, and I see the potential to scale further.
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What do you enjoy most about this side hustle?
The best part is seeing how much joy these cars bring to people. There’s something about classic cars that makes any event more memorable. I love hearing from clients after their weddings or anniversaries, telling me how much attention the car got or how it made their day extra special. It’s more than just a rental — it becomes part of the experience. And, of course, the attention the cars get is fun, too — people wave, take pictures and come up to ask questions wherever the car goes.
One of the most popular types of events we’ve been booked for are Indian weddings, particularly for the traditional baraat ceremony. The Mustang is often chosen for its symbolic connection to horses in Indian culture, and we regularly get requests to provide it for these celebrations.
What’s your advice for others hoping to start successful side hustles of their own?
My advice is simple: If you’ve got something of value like a classic car, just start. Many people with classic cars don’t even realize there’s a market for it. You can rent it out just a few times a year to cover maintenance or scale it into something bigger like I did. Understand the platforms you’re using, learn about the insurance and legal requirements and make sure you keep your car in great shape. But above all, find a balance. Don’t rush into it, and don’t overwhelm yourself — start small and see where it takes you.
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