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New money in Maine

Thanks to the WFH shift of the pandemic, the Pine Tree State is seeing an influx of new deals and deal makers.

The pandemic, for all of its challenges, changed the way we did business forever. The Zoomification of America meant that we were less tied to an office. For those in the finance industry this meant connecting remotely from their suburban enclave in Connecticut or Westchester—or then again, heading someplace where the only likely traffic jam is caused by a moose. Welcome to Maine.

As the New Builders Dispatch, an influential newsletter focusing on startups, first reported, the PE crowd is descending on the Pine Tree State.

Lars Perkins, who famously sold Picasa to Google in 2004, moved operations from Southern California to the home he’s owned in Maine for 25 years. And then came a chance, as NBD reported, “to be part of a $200 million effort to turn Portland, a city of 66,000 known for its lobsters, into a technology hub.” Soon Perkins was named head of the new Techstars startup accelerator associated with the city’s Roux Institute. “Covid put me in Maine, and this opportunity came along, and I just thought it was a match made in heaven,” Perkins has said.

Waterfront homes. York, Maine, USA
Maine has served as a summer home-away-from-home for the fabulously wealthy since the Gilded Age. Photo by peeterv via Getty Images

It’s not just a matter of new money moving here; titans are investing as well.  Crunchbase’s analytics show that the number of investors active in Maine is climbing, noting recent funding activity by the likes of Rand Capital, Trinity Capital, Wellington Management, and others. Some major pandemic deals include the sale of the blue-chip Kennebunkport Resort Collection to EOS Investors LLC, a New York-based, privately-held real estate investment firm, in 2020; and the sale of Portland, Maine’s sole high-end luxury hotel, the Press Hotel, to West Coast private equity firm KHP Capital Partners, in 2021.

Of course, the old money here was also once the new.

If there is friction between the new and old guards, filmmaker Whit Stillman suggests it’s well under wraps. “I think people were thrilled when Martha Stewart showed up,” says Stillman, who is known for his stylish treatment of WASPy subjects (he prefers the term UHB, for Urban Haute Bourgeoisie) in films including Metropolitan, Barcelona, and The Last Days of Disco, and has been visiting Maine’s Mount Desert Island (MDI) since the late 1960s.

Of course, the old money here was also once the new. As the New England Historical Society tells it, “the newly rich” first started coming to MDI in the Gilded Age. ”They sought status, relaxation, and chances to misbehave” away from the public eye.

“The fabulously wealthy Evelyn Walsh McLean hung the 45-carat Hope Diamond from her dog’s neck. Willie K. Vanderbilt sulked in his yacht, Valiant—then the largest private vessel in the world—off Bar Harbor after his sensational divorce. And Joseph Pulitzer hid out in a soundproof Bar Harbor tower, unable to bear the slightest noise,” while J.P. Morgan “regularly attended and financially supported the island’s Episcopal churches [but] also stashed his mistresses on High Street.”

David Rockefeller, President of Chase National Bank, in 1976
David Rockefeller in 1976. The family had a summer home on Mount Desert Island for many years. Photo by Central Press/Getty Images
Emily and Mitchell Rales, who own property in Maine
Emily and Mitchell Rales. The billionaire investor, art collector, and philanthropist recently bought David Rockefeller’s property for a record-setting $19 million—and then obtained a demolition permit. Photo by Vladimir Weinstein via BFA Images

In later years the island was home to the likes of the Fords, the Auchinclosses (the young Jacqueline Bouvier was a frequent visitor), the Astors (whose Cove End estate overlooked the exclusive Northeast Harbor Yacht Club), and—most importantly—John D. Rockefeller Jr., who donated much of the land that has since become Acadia National Park.

But some time after David Rockefeller, John D. Rockefeller Jr.’s grandson, died in 2017, Mitchell Rales, a billionaire investor, art collector and philanthropist snapped up his 14.8-acre Ringing Point property in the exclusive MDI enclave of Seal Harbor for a record-setting $19 million—and in 2022, while the state was still reeling from the effects of the pandemic, he obtained a demolition permit.

And, though the Rockefellers themselves (who still own other property on and around the island) demolished an earlier cottage to build Ringing Point some 50 years ago, nothing could have more emphatically signaled the end of an era on MDI.

Members of the Bush family at Walker’s Point, the family’s oceanfront compound in Maine
George H. W. Bush (“41”) and wife, Laura, with other members of the Bush clan at Walker’s Point, their oceanfront compound. George W. (“43”) is now a frequent summer resident. Photo by jean-Louis Atlan/Sygma via Getty Images
The Kennebunk River Club in Maine, MA.
The Kennebunk River Club, a favorite of some of the younger Bush generation. Lauren Bush and her husband, David Lauren, are frequent visitors. Photo by Jared Paul Stern

Further south, Prouts Neck, another posh part of the state (the Wall Street Journal calls it “tribal” and “old-moneyed”), where the Rockefeller family has also owned oceanfront property for ages, has seen similar changes post pandemic.

The appearance of high profile Prouts Neck residents—such as actress Glenn Close and NFL Commissioner Roger Goodell—often makes the news. (A disgruntled New England Patriots fan once even hired a plane to fly a pejorative banner over the neighborhood following the famous “Deflategate” scandal—which can’t have endeared Goodell to his publicity-shy neighbors.)

Meanwhile, some 25 miles away in Kennebunkport, former President George W. Bush (“43”) has quietly taken his father George H.W. Bush’s (“41”) place as a more or less full-time summer resident at Walker’s Point, the family’s oceanfront compound that’s a mecca for tourists in the area.

An even younger generation is often present in the form of “41” granddaughter Lauren Bush and her husband David Lauren, son of billionaire designer Ralph. The couple can often be spotted riding bikes and dining out at local favorites like Wandby Landing—named after a shipwreck—or stopping by the exclusive Kennebunk River Club.

Maine native actor Patrick Dempsey has endeared himself to all, thanks to his philanthropic endeavors.

Just down the road from Walker’s Point is the elegant stone mansion built for author Kenneth Roberts in 1938. It’s now home to actor Patrick Dempsey, who purchased it a few years ago—a Maine native who has endeared himself to all, thanks to his philanthropic endeavors.

Perhaps more surprising is the fact that Mr. Saturday Night Fever himself, John Travolta, has a place on the traditionally preppy midcoast preserve of Dark Harbor on Isleboro. In 2021, he listed his historic 10,000-square-foot house for sale for $5 million after the death of his wife, Kelly Preston, but subsequently took it off the market.

Another Isleboro resident, writer Marina Rust has lived in her great-great grandmother’s house on the island for 25 years.

Martha Stewart, David Lauren, and Lauren Bush
Martha Stewart—seen here with David Lauren and Lauren Bush—bought Skylands, Henry Ford’s estate on Mount Desert Island, in 1997. Photo by Stefania M. D'Alessandro/Getty Images for Ralph Lauren
Filmmaker Whit Stillman
Filmmaker Whit Stillman has been visiting Mount Desert Island since the late 1960s. Photo by Gage Skidmore via Wikimedia Commons
Renee Rockefeller and Marina Rust.
The families of Renee Rockefeller, left, and Marina Rust have been fixtures in Maine for decades. Photo by Billy Farrell/Patrick McMullan via Getty Images

About the changing face of Maine, Rust notes, “It was a matriarchy. When women were able to be here all summer, the men just would come up when they could.” While the sense of the area as a women-dominated territory is waning, “because women have places to be during the week too, there are more husbands who are able to spend more time on this island.

“We celebrate JOMO (the joy of missing out). There is nothing like watching pictures of people in their travels around the world, realizing, ‘I’m just here on my favorite porch looking at this view, not having to go anywhere and face an airport,’” says Rust. That may be the true enduring gift of the remoteness of Maine.

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