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I Toured Hidden-in-Plain-Sight Places Where the Wealthiest People in New York Spend Their Time. Here Are 3 Ways They're Living Differently. Life can be a lot easier when you have money — but not always.

By Amanda Breen Edited by Jessica Thomas

Key Takeaways

  • I took ExperienceFirst's new Unofficial 'Succession' Tour, which offers a glimpse into the show's most iconic moments.
  • Many of the locations give the impression of being hidden in plain sight — much like the lifestyles of the rich and famous.
Macall B. Polay/HBO. Courtesy of Warner Bros. Discovery.

The hit HBO drama Succession, which centers on the Roy siblings' battle for their father Logan's media conglomerate Waystar Royco, might have aired its fourth and final season earlier this year, but fans are still obsessed with its power-hungry, ultra-rich cast of characters — and the real-life people and places that inspired their on-screen storylines.

Now, viewers who can't get enough of the luxurious dysfunction have a chance to dive even deeper and see it all up close. ExperienceFirst, a tour company with expert local guides in cities across the globe, just launched its Unofficial Succession Tour, which takes participants around the Financial District to "experience the glamor and drama of a day in the life of a Waystar Royco executive."

Image Credit: David Russell/HBO. Courtesy of Warner Bros. Discovery. Logan Roy.

My fiancé and I were some of the first people to take the new tour. Having just watched the finale the night before, we were ready to see the locations we'd gotten to know so well over the show's 39 episodes, and our guide didn't disappoint. He offered plenty of anecdotes about the Murdoch family (the inspiration for the Roys) and other powerful New York players.

In fact, the Roys are so similar to the Murdochs that billionaire media mogul Rupert Murdoch — who recently handed over Fox and News Corp to his eldest son Lachlan — reportedly included a clause in his divorce settlement with fourth wife Jerry Hall that prohibited her from giving story ideas to the writers of Succession, per Vanity Fair.

Related: 4th-Gen CEO Reveals How to Avoid Dysfunction in Your Business

Our tour began at 85 Chambers Street, just outside the subway station. We all received "We Here for You" stickers (if you know, you know) and looked skyward to two filming locations already in view: the Woolworth Building, with its $30 million penthouse that serves as Rava's apartment, and 270 Broadway, which features a $4 million penthouse where many of Shiv Roy and Tom Wambsgans' scenes were shot. The juxtaposition of the Woolworth's ornate exterior and 270 Broadway's subtler facade — both visible from where we stood, both harboring opulent apartments and their wealthy residents — evokes the push and pull of Manhattan's markers of status. They're everywhere, but they can fly under the radar, especially if you don't know where to look. In a sense, they're hidden in plain sight.

Image Credit: ExperienceFirst. The guide showing an image of The Woolworth Building.

ExperienceFirst's Succession tour highlights that tension with several locations that are more than they might seem at a glance, surrounded by stories that reveal just how different life is for the wealthiest among us. Here are three of them that stood out:

4 World Trade Center: People with enough money and connections can get away with almost anything

One of our first stops on the tour was 4 World Trade Center, which serves as Waystar Royco headquarters and is one of the show's top shooting locations. Designed by Maki and Associates, the building opened in November 2013 and boasts 2.5 million square feet of rentable space, which is currently leased by tenants including Spotify, Morningstar and The Port Authority, City of New York.

Although commercial developer Silverstein Properties owns the 977-foot tall 4 World Trade Center (along with 2, 3 and 7), it sits in the shadow of 1 World Trade Center, which stands at 1,776 feet and is the tallest building in the Western Hemisphere. The latter, completed in November 2014, was built by The Port Authority of New York and New Jersey and The Durst Organization in a public-private partnership.

Image Credit: ExperienceFirst. One World Trade Center in the background.

If the name "Durst" sounds familiar, you might have tuned in to HBO's 2015 docuseries The Jinx: The Life and Deaths of Robert Durst, which delves into the bizarre history of real estate heir Robert Durst, a long-time suspect in the 1982 disappearance of his wife Kathleen McCormack and the murders of family friend Susan Berman and neighbor Morris Black. In the final episode of the series, Durst is caught muttering he "killed them all" and was later convicted of first-degree murder in the Berman case and sentenced to life in prison. He died before he could stand trial for McCormack's death. Durst nearly got away with murder, no doubt aided by his vast financial resources: A 2019 lawsuit filed by McCormack's sister alleged that the wealthy Durst family was involved in a cover-up "to protect [Robert] Durst and The Durst Organization from any connection to Kathie's disappearance and murder."

Likewise, in Succession, eldest son Kendall Roy relies on his family's wealth and power to shield him from any consequences when someone ends up dead. He's driving a car that crashes off a bridge and into the water in the first season's finale, and after a failed attempt to search the depths for the cater waiter who was in the passenger seat (there because Roy asked for his help finding drugs), he leaves the scene and doesn't report it. The next day, when his father Logan Roy learns what happened, he doesn't hesitate to use his resources to make it go away — though he never lets his son forget it, either.

Image Credit: Colin Hutton/HBO. Courtesy of Warner Bros. Discovery. Kendall Roy after the accident.

Related: 8 Things I Discovered While Working With Affluent Clients in New York City

Downtown Manhattan Heliport: Wealthy people don't have to wait in traffic if they take to the sky

Our guide also led us to the Downtown Manhattan Heliport, located at the base of Wall Street on the East River. Only minutes away from John F. Kennedy, Newark Liberty, LaGuardia and Teterboro Airports, it consists of 84,000 square feet with parking for 12 helicopters on the barge and 18 cars in the lot, providing a convenient travel option for wealthy executives like the Roys.

Image Credit: ExperienceFirst. Downtown Manhattan Heliport.

No helicopters were on-site when our group visited on an overcast, drizzly day, and there's nothing particularly striking about the landing pad itself, another example of how easy it can be to overlook some of the city's most glaring symbols of wealth. But make no mistake, on a clear day, the Downtown Manhattan Heliport's existence — and all of the noise that surrounds it — can't be ignored. In 2022 alone, an estimated 30,000 non-essential and tourist helicopter flights took off from the heliport, and more than 17,000 helicopter-related noise complaints were filed from Manhattan, a 3,600% increase in the past five years.

The Roys flit from Point A to Point B with ease thanks to helicopters and private jets. In the show's very first episode, a helicopter transports them to a space expansive enough for them to play "The Game," then whisks them away again after the stomach-turning scene where second son Roman Roy rips up a $1 million check in front of a boy and his parents when the child fails to hit a home run. And, early in the final season, Logan Roy meets his demise in the bathroom of a private jet; his three youngest children say goodbye over the phone and consider letting the aircraft circle as they figure out the next steps for themselves and the company.

Image Credit: Craig Blankenhorn/HBO. Courtesy of Warner Bros. Discovery. Connor, Roman and Shiv Roy post-helicopter ride.

Related: You'll Soon Be Able to Order Flights Through the Uber App

Cipriani South Street: HENRYs can make life more difficult for the really rich

One of our final stops on the tour was Cipriani South Street at the Maritime Battery Building, home to private members club Casa Cipriani. It's "a true private members club in the modern sense, bring[ing] together an eclectic community who shares life's simple pleasures," per Casa Cipriani's site. With memberships starting at just $3,500 per year, the club's known to attract its fair share of HENRYs: High Earner, Not Rich Yets, our guide informed us.

Image Credit: ExperienceFirst. Casa Cipriani exterior.

But it's not always smooth sailing when HENRYs mingle with more established folks, especially when they happen to be celebrities. Earlier this year, several Casa Cipriani members broke the club's no-photos rule when they snapped pictures of superstar singer-songwriter Taylor Swift, who boasts a net worth of $740 million, on a date with the lead vocalist of the 1975 Matty Healy, Page Six reported.

Related: Taylor Swift Gave Tour Staff $100,000 Bonuses Totaling $55M

In Succession, Shiv Roy and Tom Wambsgans' relationship is perhaps the best example of what can go awry when different levels of wealth and status collide. Although we never learn how Shiv and Tom met and kicked off their complicated, painful-to-watch relationship, we're reminded ad nauseaum that he's from St. Paul, Minnesota — and not on the same playing field as his ultra-wealthy wife, who could be Waystar Royco's next CEO.

Image Credit: Graeme Hunter. Courtesy of Warner Bros. Discovery. Shiv Roy and Tom Wambsgans.

Of course, he gets the last laugh in the series finale when GoJo CEO Lukas Matsson takes over the company and Wambsgans is appointed as American CEO, ending the question of succession once and for all.

Amanda Breen

Entrepreneur Staff

Senior Features Writer

Amanda Breen is a senior features writer at Entrepreneur.com. She is a graduate of Barnard College and received an MFA in writing at Columbia University, where she was a news fellow for the School of the Arts.

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