Why Sell Your Bootstrapped Business At Its Peak? To Play the Long Game, Says Vinny Breslin

Thirty-nine-year-old Irish founder Vinny Breslin believes in pursuing every opportunity in life.

A few months ago, he received a multimillion-dollar, all-cash offer for his bootstrapped short-term rental scheduling and support business, Uplisting. He took it.

While cashing out for millions might seem like the obvious choice, Uplisting was processing $400 million in bookings with 30 fully remote employees. It was one of Airbnb’s preferred software providers in a crowded market of VC-backed competitors. Why didn’t Vinny continue riding that high?

It may be because Vinny knows failure. He bounced between jobs and industries for much of his twenties. He even started and failed a startup with his mother. He knew that no matter how high you fly, you can always come crashing back down. Fortunately, he didn’t do that. Here’s how he pulled off one of the most inspiring SaaS exits of 2023.

I Get It From My Mother

When Vinny hears the word entrepreneur, his thoughts usually go to his mother, Sian Breslin.

Outside of her day job as a teacher, Sian would sew and sell tweed clothing in a local shop. Later, she taught local women to sew and would even invite professionals to teach classes. Over a decade later, Sian’s knack for teaching would form the basis for her and Vinny’s first startup together.

“My mum had about ten sewing machines in the garage at one point,” says Vinny. “She was always on the go, and I thought that was normal.”

Vinny credits his mother as half responsible for his dreams of entrepreneurship. The other half came with the abrupt arrival of the internet to his small town. 

As a child in rural Donegal, Ireland, during the 1990s, Vinny experienced the isolation of the pre-internet era and the excitement of the digital age that followed. At 10 years old, he could access the same information as a young boy in Dublin or London.

At 13, Vinny started his first business, a scavenger hunt for tourists called Treasure Ireland. He sold the trip to about 30 people in the tourism office and won a young entrepreneur of the year competition. The prize money was enough to buy his first home computer.

From this point on, Vinny built web pages on Dreamweaver and Microsoft Access as a hobby. They were clunky websites, but the process introduced him to UX design, a skill that would help him grow Uplisting later.

In 2005, Vinny followed in his father’s footsteps and went to Cardiff University in Wales to study civil engineering. He believes that in another era he might have chosen programming. But after the dot-com bubble burst, many in his generation chose to stay as far away from coding and the internet as possible.

Civil engineering ended up being a good financial decision. Vinny graduated college during a boom period in Ireland called the Celtic Tiger when the country saw a drastic increase in foreign direct investment. He secured engineering work in Dublin during the city’s rapid expansion. 

Although the money was good, engineering wore on Vinny. He didn’t like being a cog in the machine; he wanted to control a project from start to finish.

“I went into engineering because I love problem-solving,” he says. “But in engineering, you’re building a small part of a bridge or a road. It takes years before the thing you’re designing becomes something.”

In 2010, Vinny left engineering and Ireland for a career in design in London. He transferred his project management skills to a product project manager role for media company Ten Alps Design. One year later, he joined another design agency in Soho with clients including the BBC, Channel 4, The Financial Times, and Reuters.

After two years of managing product design, Vinny still yearned to create something of his own. He saw a new opportunity with the person who taught him about entrepreneurship: his mother.

Sian’s Plan

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

Seeing a new business opportunity, his mother 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. In 2012, he teamed up with Sian, and after hours of phone calls and pitching contests, secured half a million in VC funding for his new startup, Sian’s Plan.

While Vinny believed venture funding was required to build a startup, the application process seemed unnatural to him from the start.

Instead of spending time and money to keep a failing business alive, you should spend it building a sustainable business

“As an unproven entrepreneur, I never enjoyed having to convince people I was worth investing in,” he says.

Building a business under pressure from hard-won investors was also a pain. Sian’s Plan acquired roughly 10,000 customers and cemented partnerships with a handful of household names like the UK’s Tesco and Ireland’s SuperValu. But they never made enough money to afford an in-house engineer. Vinny also needed to convince an entire board every time he wanted to pivot. The business couldn’t iterate quickly so it stalled.

“I learned that instead of spending time and money to keep a failing business alive, you should spend it building a sustainable business,” he says. “For my next company, I was conscious that we’d do it sustainably.”

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.

Discovering the Airbnb Problem

It’s always darkest before dawn, as the saying goes, and the death of Sian’s Plan triggered the chain of events that would push Vinny to create Uplisting. 

Tech CEO experience looked great on Vinny’s resume. He leveraged his background to obtain a general manager job at an Airbnb competitor in London called House Trip (acquired by TripAdvisor in 2016). 

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.”

After the House Trip acquisition in 2016, just one year after Vinny joined, he knew his next business would solve the problem of syncing short-term rental calendars.

Building Uplisting

In 2017, Vinny married his wife, Shaunagh, in Ireland. He invited two former coworkers at House Trip, Tadej Murovec and Andy Shipman, to celebrate with them. They were his new technical cofounders at Uplisting, the business they’d started to solve the double-booking problem.

While they would speak every day, the trio wouldn’t see each other again in person for six years. But we’ll get to that later.

Through Uplisting, Vinny was determined to right every wrong he made with Sian’s plan. He rejected outside funding (though later he’d raise a small, non-controlling equity round from his customers and Calm Fund) and spent the first two years working at a private tech incubator called Immergent Solutions to pay the bills.

Vinny’s technical cofounders did most of the engineering work so they didn’t need to hire developers. Rather than try to predict what customers wanted, or feverishly analyze data to persuade a board, he spoke with customers every day to improve his product.

When you’re a bootstrapped company, every product decision has to make money. You make better decisions

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. Uplisting needed to use a band-aid solution for years to track stays on Airbnb.

“We needed to constantly reverse-engineer the Airbnb app so that our service remained compatible,” he says. “Whenever Airbnb updated, we would jump online immediately to figure out what they’d changed. We were regularly up all hours of the night doing that.”

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. No easy task in an industry filled with competition raising millions in VC funding.

“We were competing against extremely well-funded competitors and managing to hold our own,” says Vinny proudly. “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.”

By the end of 2023, Uplisting possessed 1,500 customers and made $3 million in ARR. Vinny had put together a strong SaaS business that even his mother, Sian, was using.

“She says it’s by far the best tool out there,” he laughs.

That’s around the time Vinny started receiving serious acquisition offers.

Sell For What You’re Worth

In 2023, Vinny, Tadej, and Andy finally met in person again on a group trip to Slovenia.

The subject of their meeting was the mouth-watering offer they’d received from a potential buyer. They were likely days away from never needing to work again. 

By the time Uplisting crossed $2 million in ARR, Vinny was accustomed to acquisition and funding offers. It was the surest sign he was building a good business – a stark contrast to his previous venture.

(Read our blog, 10 Ways to Attract More Acquisition Offers for Your SaaS Startup)

“With Sian’s Plan, I was always searching for new VCs for funding,” he says. “With Uplisting, I spent a lot of time just archiving emails from people trying to give us money.”

But because Vinny was running a fast-growing business in a high-value niche, he refused to sell for anything less than a VC-grade multiple of his ARR. He’d received many low-ball offers. During those days, most buyout offers went directly to the trash folder. 

However, when he was approached by a representative for PE fund Alpine Investors, Vinny had an idea he might get the right offer.

(Curious about how to get acquired by private equity? Read our blog on what PE looks for in startups.)

Alpine Investors approached Uplisting on behalf of Denver-based AirDNA, a service tracking the daily performance of over ten million properties on Airbnb and Vrbo. Alpine Investors (a $4.5 billion fund) took control of AirDNA in March 2022 hoping to create the market leader for short-term rental support.

Vinny was impressed with AirDNA for two reasons. First, they were willing to buy his business for a multiple of their revenue, and second, their network could quickly grow revenue.

“Our biggest challenges were always on the customer acquisition side,” he says. “We thought being acquired by a well-known company in the industry would help us. AirDNA also owns all the data in our space.”

With the right price in front of him and good prospects for his business and employees, Vinny and his team were quick to agree to a sale.

“It was emotional, but I had no problems handing it over,” he says. “The money was going to be life-changing. But the deal wasn’t done until I saw that money in my bank account.”

The team hired FOCUS Capital as financial advisors to get their due diligence documents up to date, and they completed the sale by Thanksgiving 2023. While Vinny hadn’t planned to sell when building the business, he believes he transitioned smoothly because he’d kept his cap table clean with controlling shares only belonging to his cofounders.

Now Vinny is taking a well-deserved rest while he figures out his next move.

Vinny’s Advice for Other Founders

For the last two months, Vinny has pondered his decade-long journey. Today, he thinks he can speak confidently about what worked and what didn’t when he was running his startups.

His most pressing piece of advice is he believes founders need to avoid getting wrapped up in startup hype.

if we had to raise VC money from the start, that removes the option of us just building a sustainable business

“Anything you read that hits publications like TechCrunch is always about big funding rounds,” he says. “It’s not attractive to simply grow a good business that makes money. A lot of companies raise money just as a point of comparison and my first mistake was getting wrapped up in that.”

By avoiding hype, Vinny believes founders can keep their options open in the future.

“We didn’t raise VC money because if we had to raise VC money from the start, that removes the option of us just building a sustainable business without having to aim for a two-hundred-million-plus exit,” he says. “In life and business, when you’re thinking about decisions you need to ask, ‘Is that going to remove an option for me?’”

And Vinny isn’t finished working on startups. To him, it’s the single greatest learning experience anyone can undertake.

“I’d like to try and do it all again,” he says. “It’s a fun journey for the most part. My cofounders and I are excited to talk about the next thing we’re going to do.”

(Thinking about selling your startup but unsure if it’s the right time? Read what the data says on Acquire.com.)

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