$3 Million Per Year Syncing Vacation Rental Software

Vinny Breslin is the founder of Uplisting, self-described as…

All-in-one Vacation Rental Software and Channel Management System

So if you have a rental property, Uplisting plugs into sites like AirBnB and Booking.com to keep all your bookings and availability in sync 😎

Per a recent interview, in 2023…

Uplisting possessed 1,500 customers and made $3 million in [annual recurring revenue].

🚀 How it started…

When Vinny left for university in 2005, his parents bought a guesthouse with 16 rooms.

Seeing a new business opportunity, his mother [Sian] opened a school in the guesthouse for other mothers. She taught them how to cook cheap and healthy recipes, and it was a local success.

Vinny thought the world might want to participate in his mother’s classes, too.

He picked up the idea, named it Sian’s Plan, got on some calls with venture capitalists and…

Secured half a million in VC funding for his new startup…

Building a business under pressure from hard-won investors was also a pain. Sian’s Plan acquired roughly 10,000 customers…

In 2015, after three and a half years of effort, Vinny and his mother quietly laid Sian’s Plan to rest. But Vinny was far from defeated.

So that business ultimately failed 😕 but Vinny learned a lot along the way.

Next he got a job as…

A general manager… at an Airbnb competitor in London called House Trip.

While working at House Trip, Vinny noticed a common customer complaint. Hosts would forget to update their property’s availability and pricing because they were too busy focusing on Airbnb.

Even when hosts tried to maintain listings across multiple sites, they’d run into trouble. “An Airbnb booking, for example, wouldn’t block the dates on other booking sites,” Vinny adds. “So they would eventually end up with a double booking which cost them money.”

🤝 So in 2017 Vinny partnered with two of his former co-workers at House Trip to start a new business that would solve the syncing issue…

Fortunately, it was easy to find customers. The industry craved a system for syncing rental stays. However, it was often challenging to integrate Uplisting with major booking sites…

After a couple of calls to Airbnb’s Ireland office over the first two years of operation, Uplisting secured an integration, even becoming a preferred provider.

This time around, Vinny didn’t take any VC funding…

Listening to customers and building for their needs helped in a big way. When you’re a bootstrapped company, every product decision has to make money. You make better decisions.

💰 6 years later, in 2023, Uplisting was doing millions in revenue…

Vinny had put together a strong SaaS business that even his mother, Sian, was using.

They started getting buyout offers and ended up selling it for a “lucrative offer” last year.

Researching SaaS multiples, it looks like they’re at least 3-4x annual revenue nowadays, so it’s probably safe to say they sold for $10+ million 🤑

One takeaway from Vinny’s story: past failures can lay the groundwork for future success.

Must have been tough to close up shop on Sian’s Plan after 3.5 years of effort and go back to being an employee. But sometimes you have to backtrack a bit before you can move forward 👍

I also like the detail about how they persisted with Airbnb to get that integration. I’m sure that was a massive win for their business, and it was 2 years in the making.

None of this stuff happens overnight.

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