When the press covered the announcement of a $2 billion luxury development in Puerto Rico last year, the Reuben Brothers grabbed the headlines.
The resort, called Esencia, is just one of many huge swings in the wealthy British family’s international real estate portfolio.
But for the Reubens’ partner, Will Bennett, the project is everything.
“We’re like horses with blinders, just hyper-focused on Esencia,” Bennett, 40, said. He can’t resist an animal analogy, having lived on a farm in Bedford, in Westchester County, New York, until he was 13.
The developer founded Three Rules Capital with business partner Roberto Ruiz Vargas three years ago. This is their first project.
Not every new development shop kicks the tires by working with the Reuben family on a master-planned community of luxury hotels, two golf courses, 1,000 branded residences, a bilingual K-12 school and its own airfield on over 2,000 acres of pristine land overlooking the Caribbean sea.
But though this is his grand plan, Bennett does not neatly fit the mold of the ambitious developer.
He doesn’t seem to have the megalomania that defines older generations who can’t seem to step back from building. One day, he hopes to move back to the northeast to teach and coach hockey at his old high school, Phillips Exeter, with his best friend — something it’s hard to imagine Stephen Ross copping to.
Nor does he come from the real estate roots that plunked fellow millennials Alex Witkoff and the Lutnick brothers into positions of power fairly young; both of Bennett’s parents died before he turned 30, though his family pedigree of clubs, homes and schools makes it clear he’s hardly unconnected.
Instead, Bennett has turned a deficit into a strength, forging relationships — with Related’s Ross, a former ambassador to Norway and his newest financial backers — where he didn’t have real estate birthright, and finding he’s got a solid network of believers.
“His ability to get creative and make a bold move and then convince people that it’s real and it’s great for them, it’s all genuine,” Ruiz Vargas said. “He’s really caring for people’s best interests and I think that’s why he tends to have so many people that follow him.”
A new destination
Puerto Rico has not typically been the destination of choice for wealthy individuals looking to sink several million dollars on a new home, but Bennett is on the vanguard of change with his sprawling resort on the island’s west coast.
It took over two years for Bennett, who brought in Ruiz Vargas after starting his search in 2021, to assemble the 80 parcels that make up the site.
While other luxury resorts dot the island, they all surround the capital of San Juan — Esencia, a two-hour drive from the city, represents less charted territory. But according to Bennett, the Reuben Brothers, who are the only other partners on the project, saw the vision immediately.
“They understood the demand because the island has had an incredible run in prices,” he said. “There’s a lot of people moving there — buying both primary homes and second and third homes — but there’s very little inventory and very little in future development.”
The Aman Group, Mandarin Oriental and Rosewood Hotels & Resorts have already signed on, the latter two providing half of the full-time residences and two of the three hotels.
Phase one construction, which includes hotels and residences from Aman Group and the Mandarin Oriental, the first golf course and amenities like a racquet and field club, beach club, hiking and biking trails and much of the land development and master infrastructure, is expected to begin in several months, pending final steps in the local approval process. The hotels and first amenities are expected to open by 2028.
When completed, Esencia will impact less than a quarter of the land, which Bennett said was intentional.
“One of the reasons we’re doing luxury is so there can be low density,” Bennett said. “I think there’s a balance — if you did too much density, then you lose some of what’s special.”
“I have a lot of conviction”
The Esencia site climbs from sea level up to 350 feet at its peak, providing a stadium-seating view of the Caribbean Sea to the east and Boquerón Bay to the west.
Walking the site with two designers on the project, a yet-to-be-announced husband-and-wife duo, Bennett stopped at the top of one of the area’s many knolls to take in the rolling terrain and water views when one of the designers began to cry.
“She just — I think — was overcome with how special the site is, how peaceful it is,” Bennett said.
Bennett moved by himself to Puerto Rico in 2022, initially living in Condado, the touristy beach town on the northern tip of San Juan. Still a farm kid at heart — he used to sell fresh eggs at his school’s carpool line — he found the 6,000-person neighborhood too busy.
He ended up in the city’s business district, Hato Rey, where he walks the quieter, palm tree-lined streets of the neighborhood every day on his way to work. He still owns a home in L.A., and he’s often back for his relationship.
“She just — I think — was overcome with how special the site is, how peaceful it is.”
Bennett had hit on Puerto Rico as a development opportunity in his previous job, trying to source the next project for Jason Grosfeld at Los Angeles-based Irongate, where he worked from 2016 to 2022. There, he led a similar master-planned project, the 1,500-acre Costa Palmas resort in Los Cabos, Mexico. (Before that, he was at Related, working on 70 Vestry, the exclusive Tribeca condo of its day.)
Grosfeld had his hands full with Costa Palmas and a new venture in Aspen and wanted his team to concentrate on the two ongoing projects, not start a third.
Bennett felt differently. “I said, ’I have a lot of conviction.’”
He made his move to the Caribbean, founded Three Rules with Ruiz Vargas, who is half Puerto Rican, and spent more than a year scouring the island for the right plot of land. (A third partner, Harish Venkatesh, joined in 2023.)
The case for Puerto Rico, in Bennett’s mind, was simple. “This is as beautiful a place as I’ve ever been to in my life,” he said. “It’s in the United States, it’s super easy to get to, and it’s underrepresented from a luxury standpoint.”
He chafed at a comparison to South Florida; both have attracted a number of nouveau-rich cryptocurrency traders. Bennett said that a majority of early sales have been to locals and others who appreciate Puerto Rican culture. (In Puerto Rico, Bennett says, everybody applauds when a plane lands, betraying a level of earnestness he doesn’t see in the continental U.S. He appreciates this.)
“Miami is a very vertical city, there’s crazy traffic, it’s cosmopolitan — it’s very different than moving to Puerto Rico where you’re immersed in nature,” Bennett said.
That’s not to say he wants the place to be a monastery.
His vision for Esencia stands in contrast to typical luxury resorts: gated communities with a handful of restaurants that fall asleep by 10 p.m.
“We want this to be embraced by the whole west side of the island, the town center to be the heartbeat of that whole part of the island,” Bennett said.
The other players
Bennett is not the only one betting on Puerto Rico; billionaire John Paulson has put hundreds of millions of dollars into office, residential and hospitality projects over a decade.
The island has encouraged more big bets with recent policy changes.
Hospitality developments can claim tax credits of up to 40 percent starting once the project is operational. Esencia is in line for almost $500 million in credits when the project is complete.
The 2019 passage of Act 60, a systemization of incentives introduced to Puerto Rico in 2012, boosted residential demand by offering generous personal and corporate tax benefits to individuals residing on the island.
Wealthy homebuyers began flocking to Puerto Rico, and the number of Act 60 beneficiaries more than doubled from 2019 to 2021. The newcomers drove home prices to record highs.
So far, luxury developers have gravitated to the area near San Juan, on the east side of the island. Dorado Beach, which re-opened in 2012 as a Ritz-Carlton Reserve, spans 1,400 acres and has claimed many of the island’s most expensive residential sales, while down the coast near the El Yunque rainforest, the St. Regis Bahia Beach, in which Paulson has a majority stake, has added beachfront condominiums in recent years.
Further east, construction on Juniper Capital’s Moncayo has already begun. The resort, set to launch in phases beginning in late 2026 or early 2027, will feature an Auberge-branded hotel and 400 residences.
“You cannot build enough in Puerto Rico,” said Margaret Pena-Juvelier, founder of Puerto Rico Sotheby’s International Realty, who added that she already has buyers interested in Esencia.
Connecting the dots
None of the project would be possible without the buy-in of the Reuben Brothers, whom Bennett called “some of the best capital allocators in real estate.”
Bennett said he had a chance to sell Jamie Reuben (principal at Reuben Brothers) on the project after the two ended up in Los Angeles together during Covid. The fit between the guys, then both 30-something former prep schoolers, was easy. In typical genteel fashion, the pair, who had been in each other’s orbit for years, bonded through racket sports. (Esencia will have tennis, squash, pickleball and padel courts.)
Since investing, David Reuben, Jamie’s father, has also been to the island multiple times.
The two make for a study in contrasts: Reuben helping lead the firm named after his father and uncle, and Bennett leading his own fledgling company, named for his late mother’s three rules: “always tell the truth,” “always be kind” and “always do your best.”
Just as Reuben and many others stepping into the world of development can credit their parents, Bennett, in his optimistic way, credits the loss of his.
“If you can get past anger and sadness, it’s really valuable to have gone through some adversity, because it gives you confidence that you can kind of get through any challenge,” he said.
Bennett also had mentors like Marc Nathanson, a cable empire billionaire and one-time U.S. Ambassador to Norway, and Harvard Business School professor Arthur Segel, who took him under their wings and pushed his career along.
“Maybe they felt sorry because of my personal situation, but I also just was willing to do anything for them,” Bennett said. “I’ve had guys like Marc, Arthur — all these kinds of guys who were like second fathers.”
Segel says it’s not so Freudian. “[Will has] a kind of a real, genuine sensitivity to people,” Segel said. Bennett checked in with him constantly when Segel had knee surgery. “He’s just very thoughtful and a very good listener and has this integrity that just permeates from him.”
And then there’s Related’s Ross, who would regale Bennett and the team working on 70 Vestry with stories over dinner in the office most nights. He and his world-building instincts have influenced Bennett’s grand ambitions for Esencia, according to Ruiz Vargas.
In the modern real estate world, where the prime locations seem tapped and the capital allocated, it might take this kind of confluence of circumstance and personality to breed this kind of developer, builders who aren’t afraid to stake their claim in a place just outside the hotspot or build their network from the ground up.
Bennett still has a long road ahead — at least five years from now to deliver the entirety of the project, if all goes according to plan. If the bet pays off, Bennett will be one step closer to joining the ranks of his mentors.