How This 52-Year-Old Makes Up to $30,000 From His Car Rental Business
How This 52-Year-Old Makes Up to $30,000 From His Car Rental Business
Oct 3, 2024
Shawn O'Connell
Shawn O'Connell
● 4 min
● 4 min
Revenue/year
Revenue/year
$30,000
$30,000
$30,000
No. of founders
No. of founders
1
1
1
Startup costs
Startup costs
N/A
N/A
N/A
Company Type
Company Type
Company Type
Service-based
Service-based
Service-based
Contents
How it started
How it started
When you think of side hustles, you probably picture people flipping furniture or selling products online. But for one sales leader turned entrepreneur, his side hustle began with a car—specifically, a vintage Mustang that had been in the family for years.
When you think of side hustles, you probably picture people flipping furniture or selling products online. But for one sales leader turned entrepreneur, his side hustle began with a car—specifically, a vintage Mustang that had been in the family for years.
From Corporate Sales to Classic Car Rentals
From Corporate Sales to Classic Car Rentals
At the time, Shawn was working as a sales leader for a tech company. While it was a steady job, his real passion had always been classic cars—a love inherited from his dad, who spent years restoring vintage vehicles. When his dad’s prized Mustang came into his possession, the question wasn’t if he should drive it, but how to make it work for him. That’s when the idea clicked: Why not rent it out?
At the time, Shawn was working as a sales leader for a tech company. While it was a steady job, his real passion had always been classic cars—a love inherited from his dad, who spent years restoring vintage vehicles. When his dad’s prized Mustang came into his possession, the question wasn’t if he should drive it, but how to make it work for him. That’s when the idea clicked: Why not rent it out?
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➤ Every week, we dig up stories of how regular people started and grew their businesses—
➤ Plus the marketing hacks that won them customers.
➤ Then, we share those insights with you.
The Spark That Started It All
The Spark That Started It All
The story kicks off in 2020, during the pandemic, when travel plans were unexpectedly disrupted. While planning a trip to Phoenix with his wife, they encountered an issue common during COVID times—no cars were available for rental. After a bit of frustration, they discovered a peer-to-peer car rental platform that allowed individuals to rent out their personal vehicles. The process was seamless, and it was cheaper and more convenient than dealing with traditional car rental agencies.
This experience planted the seed. If others could rent out their cars, why not him? Within 24 hours of listing his Mustang on a rental platform, he had six bookings. The demand was real.
The story kicks off in 2020, during the pandemic, when travel plans were unexpectedly disrupted. While planning a trip to Phoenix with his wife, they encountered an issue common during COVID times—no cars were available for rental. After a bit of frustration, they discovered a peer-to-peer car rental platform that allowed individuals to rent out their personal vehicles. The process was seamless, and it was cheaper and more convenient than dealing with traditional car rental agencies.
This experience planted the seed. If others could rent out their cars, why not him? Within 24 hours of listing his Mustang on a rental platform, he had six bookings. The demand was real.
Taking the First Steps
Taking the First Steps
Getting his side hustle off the ground was no small feat. Shawn started by researching the best platforms to list his car. He settled on DRIVESHARE, a platform specifically for classic cars, and dove into understanding the logistics: insurance, pricing, and how to maintain the car in pristine condition. Since classic cars are often used for special events like weddings and photoshoots, he knew the car had to be spotless.
Getting his side hustle off the ground was no small feat. Shawn started by researching the best platforms to list his car. He settled on DRIVESHARE, a platform specifically for classic cars, and dove into understanding the logistics: insurance, pricing, and how to maintain the car in pristine condition. Since classic cars are often used for special events like weddings and photoshoots, he knew the car had to be spotless.
Challenges Along the Way
Challenges Along the Way
No journey is without its hurdles. For Shawn, the biggest challenge was balancing a full-time job with his growing side hustle. Managing multiple bookings, deliveries, and car maintenance while keeping up with his regular work was a juggling act. The pricing model was also tricky at first. How much should he charge for a wedding or a photoshoot? Thanks to the support from DRIVESHARE, including online guides and great customer service, he was able to figure it out.
As the business grew, his sons pitched in during the summer, helping with deliveries and logistics. Time management and planning around busy periods became key to keeping everything running smoothly.
No journey is without its hurdles. For Shawn, the biggest challenge was balancing a full-time job with his growing side hustle. Managing multiple bookings, deliveries, and car maintenance while keeping up with his regular work was a juggling act. The pricing model was also tricky at first. How much should he charge for a wedding or a photoshoot? Thanks to the support from DRIVESHARE, including online guides and great customer service, he was able to figure it out.
As the business grew, his sons pitched in during the summer, helping with deliveries and logistics. Time management and planning around busy periods became key to keeping everything running smoothly.
From Side Hustle to Steady Revenue
From Side Hustle to Steady Revenue
In the beginning, the goal was simple: Cover the costs of maintaining the Mustang. But it didn’t take long for the side hustle to turn into something more. Within the first year, the business pulled in between $24,000 and $30,000—enough to turn heads and show that there was real potential in the market for classic car rentals.
In the beginning, the goal was simple: Cover the costs of maintaining the Mustang. But it didn’t take long for the side hustle to turn into something more. Within the first year, the business pulled in between $24,000 and $30,000—enough to turn heads and show that there was real potential in the market for classic car rentals.
Growth and Expansion
Growth and Expansion
By 2022, the business had grown to the point where Shawn added a second Mustang to his fleet. In 2023, a third followed. The demand was so high that the cars were booked months in advance, especially for weddings and other major events. The business also tapped into the world of music video shoots and commercial work, which kept the cars in steady rotation.
During peak wedding season, the business handles between three to five events per week, and word-of-mouth referrals have been a huge driver of growth. Shawn can now see the potential to expand even further.
By 2022, the business had grown to the point where Shawn added a second Mustang to his fleet. In 2023, a third followed. The demand was so high that the cars were booked months in advance, especially for weddings and other major events. The business also tapped into the world of music video shoots and commercial work, which kept the cars in steady rotation.
During peak wedding season, the business handles between three to five events per week, and word-of-mouth referrals have been a huge driver of growth. Shawn can now see the potential to expand even further.
The Best Part of the Hustle
The Best Part of the Hustle
What’s the best part of running a classic car rental business? For Shawn, it’s the joy the cars bring to people. Classic cars are often a huge part of a special moment—whether it’s a wedding, an anniversary, or a milestone event. Hearing from clients about how the Mustang made their day even more memorable is the kind of feedback that fuels this business. Plus, the attention the cars get wherever they go? That’s always fun too.
What’s the best part of running a classic car rental business? For Shawn, it’s the joy the cars bring to people. Classic cars are often a huge part of a special moment—whether it’s a wedding, an anniversary, or a milestone event. Hearing from clients about how the Mustang made their day even more memorable is the kind of feedback that fuels this business. Plus, the attention the cars get wherever they go? That’s always fun too.
A Unique Niche in the Market
A Unique Niche in the Market
One of the standout niches for this business is Indian weddings. The Mustang, with its connection to horses, is often chosen for the traditional baraat ceremony, where the groom arrives on horseback. The connection between the car and Indian culture has led to regular bookings for these events, adding a unique flavor to the business’s portfolio.
One of the standout niches for this business is Indian weddings. The Mustang, with its connection to horses, is often chosen for the traditional baraat ceremony, where the groom arrives on horseback. The connection between the car and Indian culture has led to regular bookings for these events, adding a unique flavor to the business’s portfolio.
Advice for Aspiring Side Hustlers
Advice for Aspiring Side Hustlers
For anyone thinking about starting a side hustle of their own, Shawn’s advice is simple: Just start. If you have something valuable—like a classic car—don’t hesitate. You can start small, renting out your car a few times a year just to cover maintenance, or you can scale it into something more substantial over time.
Learn the platforms you’ll use, understand the insurance and legalities, and keep your car in top shape. But perhaps most importantly, don’t rush it. Balance is key. Start small, see where it takes you, and grow from there.
For anyone thinking about starting a side hustle of their own, Shawn’s advice is simple: Just start. If you have something valuable—like a classic car—don’t hesitate. You can start small, renting out your car a few times a year just to cover maintenance, or you can scale it into something more substantial over time.
Learn the platforms you’ll use, understand the insurance and legalities, and keep your car in top shape. But perhaps most importantly, don’t rush it. Balance is key. Start small, see where it takes you, and grow from there.
Full Interview
Full Interview
Full interview posted on Entrepreneur
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Full interview posted on Entrepreneur
I share more of these case studies in my newsletter and I'd love for you to join here 😊
Do me a favor and pass this on to a friend or share on X/reddit? It'll take just 20 seconds—this one took me about 10 hours to research and write 🫠
Shoot me a DM if you want to share your story or visit this page to submit your information 💌
