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 SHARE DRIVE. Responses have been edited for length and clarity.
Photo credit: Courtesy of Shawn O’Connell
What was your day job or principal occupation when you began working on the side?
At the time, I used to be working as a sales leader for a technology company. It was a regular job, but I all the time loved classic cars, thanks to my dad who owned and restored classic vehicles. So when I inherited my dad’s Mustang, I wanted to find a way to use it reasonably than leave it in the garage. Then I began looking for opportunities to rent it.
When did you begin your side business and where did you discover the inspiration for it?
Inspiration got here during the 2020 pandemic. My wife and I attempted to rent a automotive for a trip to Phoenix, but due to Covid and the wildfires, there have been no cars available. That’s when we got here across a peer-to-peer automotive 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 typical automotive rental firms. It was good and the experience made me think: Why don’t you rent my Mustang? I made a decision to list it online and inside 24 hours we had six reservations. From there I gained momentum and realized there was a real demand for classic cars like mine.
Photo credit: Courtesy of Shawn O’Connell
What were the first steps you took to break away from the game?
First, I searched for platforms where I could list my automotive. I began with several peer-to-peer automotive rental platforms including SHARE DRIVEwhich is currently the principal platform I take advantage of. I also took the time to understand how insurance works and what sort of pricing makes sense for a classic automotive rental. In the starting, it was a matter of constructing sure the automotive was in perfect condition and understanding the logistics for deliveries and pickups. Since classic cars have a different appearance than modern vehicles, I focused on keeping the automotive aesthetically pleasing and clean, knowing that it might be used for events comparable to weddings and photo shoots.
What were the biggest challenges you faced in building your side team and how did you overcome them?
One of the biggest challenges was time management. Between full-time and part-time work, there have been times when I had two cars booked at once and had to juggle customer communications, deliveries and maintenance. Another challenge at the starting was the price. For events like weddings and photo shoots, I wasn’t sure how much to charge at first, but the DRIVESHARE platform is easy to use, which helps, and additionally they offer online guides and good customer support. Now, by managing multiple bookings, I involve my sons in the summer, allowing me to higher plan and adjust my schedule during the busiest times.
Photo credit: Courtesy of Shawn O’Connell
How long did it take for you to achieve stable monthly income? How much did the side hustle earn?
Within the first few months, I began seeing consistent bookings. My goal at first was to cover the cost of maintaining my automotive, but it quickly became greater than that. The first 12 months I made between $24,000 and $30,000, depending on the season.
What does growth and revenue appear like today?
I added a second Mustang to my fleet in 2022 and one third in 2023 due to strong demand. My cars are often booked months in advance, especially for weddings and other special events. We also shoot a lot of music videos and industrial work, and these bookings often come through DRIVESHARE. During the wedding season, I book three to five events a week and clients recommend us to friends and family, which has helped us grow and I see potential for further growth.
What do you enjoy most about this side hustle?
The better part is how much fun these cars give people. There’s something about classic cars that makes any event more memorable. I like hearing clients tell me after their wedding or anniversary how much they loved the automotive and the way it made their day special. It’s greater than just a rental – it becomes a part of the experience. And in fact, the attention the cars attract is fun too – people wave, take photos, and come up to ask questions wherever the automotive goes.
One of the hottest sorts of events we book for are Indian weddings, especially those with a traditional baraat ceremony. The Mustang is often chosen due to its symbolic association with horses in Indian culture, and we frequently receive requests to provide one for these celebrations.
What is your advice to others who want to start their very own successful side hustle?
My advice is easy: if you have something precious, like a classic automotive, just start. Many individuals who own classic cars don’t even realize there is a market for them. You can rent it out a few times a 12 months to cover maintenance costs or rebuild it into something greater like I did. Familiarize yourself with the platforms you utilize, understand insurance and legal requirements, and keep your automotive in tip-top condition. But most of all, find balance. Don’t rush or overwhelm yourself – start small and see where it takes you.