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Need a Daycation? Sure you do: This Miami startup will tempt you to call in sick

Company name: Daycation

Headquarters: Miami

Concept: Daycation is creating instant vacations. The company does this by allowing its customers to buy day passes to enjoy hotel pools and amenities without having to book a room or spend the night.

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Story: Matthew Boney was on a family reunion trip in Cancún, eyeing the amenity-filled beach resorts. “We asked if we can spend the day and we’ll pay, but they all said no, you have to be staying the night,” he said. Back in his dorm room at Brown University came that middle-of-the-night startup idea: “We have to be the ones who create this system around all these amazing hotel amenities around the world so people can enjoy all this at a fraction of the cost.”

At age 19, Boney dropped out of Brown University, where he was studying economics, to start Daycation.

As Boney began to develop the concept, lean times followed — a lot of nights on air mattresses on friends’ floors in Providence, R.I., and New York City, and too many ramen noodles. In 2016, Boney moved to Miami, known for its hospitality industry and emerging tech scene. Soon after, he teamed up with Miami local Alex Novo and Mo Soussi, who also moved to South Florida, to drive Daycation’s growth.

To build a test case to show brands around the world, the cofounders went from hotel to hotel to secure their first Daycation offerings. They tested the concept on cruise passengers, visitors staying with family members or in vacation homes, and Florida residents. “We’re finding lots of locals are loving this as an escape from their everyday lives,” said Boney, Daycation’s CEO. Sold through, the day passes start at $30.

Still, the ramen noodle days continued for a while. Nearly out of money, Boney was serendipitously introduced to John Santiago, a Miami angel investor and CEO of M8, a global advertising agency. “It was a crazy sign. Every time we got to the lowest of lows something happened to keep us going,” Boney said.

In December 2017, the co-founders secured an investment from Santiago, who also provided the team with office space.

“My investment strategy is to invest in committed entrepreneurs and to help scale a great business. That’s what Daycation is — an amazing idea that adds value to people’s lives, adds value and revenue streams to other legacy businesses like hoteliers, and has incredibly sharp, committed founders who are building a self-sustaining, revenue-producing business,” Santiago said.

Since the investment, the team has increased their hotel portfolio to include the iconic Fontainebleau Miami Beach, hotels representing Marriott, Hyatt, Loews and others, and boutique brands such as COMO. Daycation attracted Silicon Valley investor Jason Calacanis as an investor, too.

Daycation is beginning to expand to other markets, starting with New York. “The idea of Daycation has become more accepted. Hoteliers are loving it,” Boney said. “We want every day to be a vacation.”

Founded: Jan. 1, 2016


Management team: Matthew Boney, CEO; Alex Novo, COO; Mo Soussi, CTO. The team is hiring for engineering and business development roles.

Financing: A $10,000 convertible note from Rough Draft Ventures in Boston, a General Catalyst innovation fund focused on top student founders, got the concept started; $100,000 from Santiago and an undisclosed investment from Calacanis’ fund are fueling Daycation’s growth.

Recent milestones: The team recently won People’s Choice at LAB Ventures’ Future of Travel Summit and was one of two finalist early-stage companies chosen to present in front of investors Calacanis, Pitbull and Comcast Ventures on the Emerge Americas Startup Showcase stage in Miami Beach this year. Calacanis invested, and now the Daycation team is part of Calacanis’ Launch accelerator program in Silicon Valley.

Biggest startup challenge: Signing the first few hotels. “Everyone wanted proof of concept in the market and references. Since we were so new, we had to find the people and hotels willing to place an early bet on us, such as Metropolitan by COMO. Those bets have paid off, and we’ve established a good reputation with our hotel partners,” Boney said.

Next steps: Expanding the team and product offerings, and market expansion.

Investor’s view: Santiago hopes to help the team with its focus on enhancing value for customers as well as maintaining its startup culture as it grows: “The progress I continue to see is in the application of Daycation’s brand values, which include empowering people to enjoy life and look for more ways and moments to relax, reenergize and reconnect. There is more to Daycation than simply using hotel amenities for a day. [Daycation’s] continued brand and value evolution is what I’m extremely excited about.”

Follow @ndahlberg on Twitter and email her at

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