The extreme South Shore: Why these Boston tech entrepreneurs are working from Puerto Rico

They’re taking advantage of post-pandemic flexibility, tax incentives, and nice weather.

The Condado waterfront in San Juan, Puerto Rico.Xavier Garcia/Bloomberg

Before COVID, Brent Grinna and Patrick Campbell ran startup companies in Boston’s Downtown Crossing, about a seven-minute walk apart, and they’d often bump into each other. A few blocks away, near Fort Point Channel, Maria Cirino reported for work at the offices of the venture capital firm .406 Ventures, driving in from Needham.

All three now mostly work from home — not unusual for these Zoom-centric times. But home is now Puerto Rico. They’re part of a community of Boston tech sector emigres that has taken root on the tropical island since 2020. Several of them know each other by virtue of having participated in the Techstars Boston entrepreneurship program, which provides early funding and mentorship for startups — and which, prior to COVID, was considered a magnet that would pull startups to Boston.

More than 110,000 people have left Massachusetts since April 2020, and Puerto Rico doesn’t show up on the top 10 list of places they’ve landed. But when I started tallying people in my network of sources, there were a few who had decamped for Miami, San Francisco, and New York — but a more notable number ended up on what I call the extreme South Shore.

“After the New Bedford expansion, the commuter rail might get here,” jokes Grinna, who bought a home about a half-hour west of San Juan.

Among the first to relocate was Tim Ericson. He and a fellow Drexel University graduate started a company in 2007 to build technology for the budding bike-share industry, helping universities, hotels, and companies manage fleets of bikes. The company, Zagster, moved to Cambridge in 2012 to participate in two entrepreneurship programs: Techstars and MassChallenge.

Ericson and his wife moved to Puerto Rico in January 2020, simply to escape winter for a few months. They rented out their home in Charlestown, and rented on the island.

“We didn’t know anyone in Puerto Rico when we moved, and we spent most of the first six weeks buying furniture,” he says. “We didn’t spend any time exploring the island. Then, COVID hit.” Lockdowns were strict, with even beaches closed for months.

COVID was initially not kind to bike-sharing, and Zagster’s assets were sold to another Cambridge company focused on mobility, Superpedestrian, in June 2020 for an undisclosed amount. Ericson says he’s now focused on acquiring and setting up the SMB Fund ― which stands for small and medium businesses ―to help connect investors with opportunities to put money into cash-flow generating businesses like landscapers, furniture makers, and air conditioning installers, which traditionally wouldn’t attract venture capital funding.

Brent Grinna, Tim Ericson, and Patrick Campbell, all former Bostonians now living in Puerto Rico.Handout

He says his lifestyle in Puerto Rico is “a lot more active” than it was in Charlestown, even though he rode his bike every day and belonged to a gym. Now, he goes ocean kayaking, hikes in a rainforest, walks his dog on the beach, and swims regularly in the Atlantic. He gets compliments on his tan: “I’m definitely getting a lot more Vitamin D,” he says.

Ericson sold his Charlestown townhouse in 2021, and bought a house in San Juan, a half-block from the beach, with a small “casita” in the yard that he turned into an office.

Venture capitalist Maria Cirino made a “recon visit” to the island in August 2020, and moved there in December. She sold homes in Needham and Fort Lauderdale, Fla., and now considers a beachfront condo at Dorado Beach, a Ritz-Carlton managed complex, home. She attends Monday meetings of her Boston venture capital firm via Zoom. (In recent years, Cirino has been dialing back her involvement in the firm she co-founded, but still serves on several boards of startups it has invested in.) Her complex is home to many hedge fund and private equity managers, she says, and she has invested in several funds that would have otherwise been difficult to put money into without personal relationships, she says.

What does Cirino miss about Boston? Trader Joe’s. What does she not miss? Snowy commutes home from her downtown office, which on at least one occasion topped three hours. “Makes three hours on a non-stop flight from San Juan to Boston seem like a piece of cake,” she says.

Since 2012, Puerto Rico has offered a bundle of tax incentives to attract people like Cirino and Ericson, nixing taxes on interest, dividends, and capital gains income — like a company being acquired. One of the requirements of the tax break is donating at least $10,000 to charity annually; Cirino says among those she supports is the Sato Project, which seeks to find homes for abandoned dogs.

Many of the ex-Bostonians she knows on the island moved during the pandemic, thanks to the ability to work anywhere — and those tax benefits. But “if the tax benefits went away tomorrow, we would still be here,” Cirino says. “The island has so much potential.”

Around the time Cirino was relocating, so was Waikit Lau, a Brookline entrepreneur. His company, RemoteHQ, is specifically geared to far-flung teams who want to videochat and collaborate while using various web-based applications. Lau grew up in Malaysia, and had spent more than two decades in Boston starting companies after earning degrees at MIT and Harvard Business School. Lau says that he had his wife had always talked about moving somewhere warmer — in part as an adventure for their kids. “My wife speaks Spanish, and we really wanted our kids to experience a different culture and pick up a second language,” he writes via e-mail. “So, we YOLO’ed it.” (YOLO: you only live once.)

Maria Cirino of 406 Ventures on the beach outside her home in Puerto Rico.Handout

On a December 2021 vacation with his wife, Brent Grinna caught up with Ericson and Kendall Hope Tucker, another entrepreneur who’d been through Techstars Boston. They introduced him to Lau, who talked about finding the right school for his kids. (The Grinnas have three young sons.)

“It really did go from, ‘let’s go on vacation’ to ‘we should move here’ in a three-day period,” says Grinna, CEO of EverTrue. The company helps universities raise money from alumni, and while it once maintained an office in the Seaport, it is now fully remote.

“Other people from other places have moved here as well,” Grinna says. “It’s a really interesting mix of very entrepreneurial people who have created a very strong, dense community in San Juan and Dorado. It’s just a dynamic time to be here.”

Grinna says his kids have traded in their hockey skates for snorkeling gear, and the two oldest have learned to surf.

Grinna’s friend, Campbell, moved to the island in 2022, just before his company ProfitWell, which analyzes pricing, was acquired for $200 million by Paddle. He tracked his time last year, since he was traveling a lot following the purchase. Paddle is based in London — and he needed to prove his Puerto Rican residency. The deal was a mix of cash and stock in Paddle, and startup acquisitions like ProfitWell’s typically pay out over a number of years to retain key employees. Campbell said he is “not comfortable getting into my personal, specific situation publicly.”

But “the unintended benefit of the tax incentives,” he writes via e-mail, is “that it actually creates a vibrant community, since a lot of tech, finance, [and] working professionals move here and they all want friends, things to do, etc., which is what we were looking for in the next place to live.” And that creates a problem that elected officials, trade groups, and owners of commercial real estate in Boston need to address — quickly and creatively.

Now, when Campbell and Grinna get together to catch up, it’s no longer in the shadow of high-rises in downtown Boston. It’s under the shade of palm trees, at a beachfront restaurant.