Pemberton
Holdings
Operator. Builder. Investor.
Operator. Builder. Investor.
Pemberton Holdings is the DeGregorio holding company, named for Pemberton Street in Revere, where Vincenzo DeGregorio grew up.
Vincenzo's first business started behind the counter at Polcari's Coffee in Boston's North End, a shop his family has been part of since the late 1970s. In 2014, still in high school and before Starbucks or Dunkin' sold cold brew, he began brewing his own and selling it to friends and teachers. Vincenzo's Cold Brew grew into a 24-hour craft cold brew delivered by the bottle across Boston, and he watched the whole category take off from the inside. He built it for love of the craft more than the money, and it taught the lesson every Pemberton company still runs on: make something people want, then make it effortless to buy again.
He studied entrepreneurship at Babson College, the No. 1 ranked school for entrepreneurship in the country, and trained at Cue Ball Capital, a Boston venture fund, where he learned how investors judge a business. Then he chose the harder seat: running them.
He has stepped in for other owners too. In 2022, when Red City Fitness in Brighton hit a rough patch with almost no ad budget, he went grassroots: street signage, third-party partner programs, and a system that captured reviews, grew the social following and turned members into referrals. It reignited the business.
Today Pemberton owns or partners in ten businesses across parking, travel technology, car rentals, home services, film and private capital. Every one runs on software, data and AI we build in-house, and Vincenzo backs other founders as an angel investor. He invested in SpaceX in 2021.
Ten businesses, each with its own name, team and customers. Pemberton owns some outright and partners with strong operators on the rest, bringing capital, technology and marketing to each.
Auto repair and parking on Broadway in Revere, minutes from Logan, and the home base for our parking and rental operations.
Revere, MA
Off-airport parking for Logan travelers, sold through our own site and the major booking marketplaces, with shuttle service to every terminal.
Boston LoganA rental fleet for travelers flying into and out of Logan, run from the Broadway lot and priced with the same data that runs our parking.
Revere, MA
A national marketplace to compare and book airport parking at 85+ airports across the U.S. and Canada. Most travelers save 40 to 60% versus on-airport rates.
triplypro.com
Bathrooms, showers and floors across Greater Boston. More than 220 bathrooms a year, a two-year written warranty and a 4.9 rating from 150+ reviews.
aguirremoderntile.com
Heating and cooling for 26 North Shore towns. Same-day no-heat calls, seven days a week, and a written price before any work begins.
homeproscontractorsllc.com
The trusted way to hire on the North Shore: vetted local contractors, up to three quotes on one written scope, compared line by line. Free for homeowners.
Launching soon
A Boston film studio making brand, corporate and social video, with a perfect 5.0 rating from every client who has reviewed us.
day2films.comOur investment arm since 2017. Systematic, automated investing in the U.S. stock market, built to compound over decades.
PrivateCraft cold brew steeped for 24 hours and delivered by the bottle, “the coffee milkman.” Started in high school in 2014, before Starbucks or Dunkin' sold cold brew.
BostonWe build and buy to hold. No exit clock and no flipping: every decision is made for the next ten years, not the next quarter.
Ownership shows up on the job, not just on the cap table. We know our customers by name and our crews by their work.
Pricing, booking, estimating, scheduling and finance run on software, data and AI we build ourselves and share across every company.
Partnerships, acquisitions and introductions.
vincenzo@pembertonholdingsllc.com