How the 37-year-old founder of a vacation rental startup stepped into an investor’s DMs and ended up with $300,000

Random direct messages on Twitter can be and, at worst, abusive.

But for Vincent Breslin, CEO and co-founder of vacation rental control platform Uplisting, DMing, an investor he met once in person, led him to get $300,000 in financing.

In August, Breslin managed to convince Tyler Tringas, the founder of the investment company Calm Company Fund, via Twitter on a whim. He met Tringas, who has 24,200 fans and is a prolific poster, thanks to his online comments on the startup. and they had already spoken on the social network.

Breslin, who has fewer than 2,000 followers on Twitter, told Insider that he also prefers to scroll through Twitter than, say, send emails in a crowded inbox.

“I’m a big fan of emails,” Breslin, 37, told Insider.

In 2017, Breslin founded Updirectory, a platform that short-term rental managers and landlords can use to manage reservations, send messages to customers, settle payments, and automate other tedious but must-have daily responsibilities on directory sites, adding Airbnb and Vrbo.

Uplisting raised an additional $200,000 from AngelList users, which allows founders to increase the budget at no cost.

Breslin spoke to Insider about his adventure as a founder and how he marked Tringas’ investment.

Breslin, an Irishman with a degree in civil and environmental engineering who also studied sustainable energy, said he liked computers but feared the industry would be unstable.

“Computing had been a bit forbidden because of the dot-com bubble,” he said. “So it wasn’t an option for me. I was discouraged from entering it. “

It was at his next job, at online vacation rental booking site HouseTrip, that he met Tadej Murovec and Andy Shipman, his co-founders of Uplisting. HouseTrip, acquired through Tripadvisor in 2016.

Breslin got fed up with the more classic fundraising strategy he used when he ran with his mother: presenting his startup to dozens of venture capitalists and asking them for money.

He took another technique for Uplisting, which he founded in London but is now in New York.

“Our idea was that we would look to get $20,000 in monthly recurring revenue, or MRR, from users, and then we could fund, just to give us some features and maybe have the edge in negotiations,” he said. .

Breslin was in a position to start attracting investors when COVID-19 hit, shutting down the industry.

But in the past summer of 2020, to Breslin’s surprise, Uplisting’s profits began to rise (he refused to provide percentages of the precise profit figures). avoid crowds.

After raising $200,000 from the platform’s users, Breslin contacted Tringas, they only saw each other once in person. However, they had already exchanged messages on Twitter and exchanged concepts in public tweets.

Breslin, who posts on Twitter several times a week, sees the platform as a wonderful position to engage with marketers and industry experts.

“I think it would be nice if Tyler cared and put in $20,000 or $30,000 if he was interested,” Breslin said.

Tringas said he was interested in one condition: that he could invest more than $250,000 instead.

What attracted Breslin to Tringas is his track record of investing in start-ups. This year, Calm invested in corporations like Pitch Gauge, a roof estimating app that uses mobile devices to conduct asset inspections, Interview Now, which modernizes the hiring procedure. for government agencies and first responders, and Girls in Marketing, which attempts to close the gender and seniority gap in marketing.

Breslin said Uplisting was interested in an acquisition and contemplating a Serie A round. No matter the path, Breslin is satisfied with his unconventional approach.

“With Tyler’s investment, it’s not about developing one hundred percent at all costs,” Breslin said. “He’s very focused on achieving safe goals slowly but with a little luck and where his business is sustainable, rather than a typical venture capital firm. “looking for that exit a hundred times multiple. “

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