Real estate is a great industry of which to be a captain. Its titans shape the skyline and make millions — sometimes billions — on brilliant deals. There’s something undeniably sexy about being the eperson who owns the building, or who sold it. You get to hold the keys.
Maybe that’s why so many upstarts get into the business with aspirations of becoming the next real estate billionaire, whether by nabbing a spot on a made-for-TV occu-soap, or climbing the ladder at a major corporation, or just parlaying one little deal into another and another.
Many have the dream, but few reach the reality. For the last few months, The Real Deal’s reporters and editors have pieced together lists of the 100 most important real estate players in each of our cities. Using data, newsroom debate, the counsel of wise sources and our years of daily coverage, we were able to shape a list of the dealmakers who move real estate across five of the biggest markets in the country.
As we did, we started to notice patterns. While every real estate icon has forged their own path, many made smart decisions that put them on fast tracks to the top.
You can read more about our picks at TheRealDeal.com/Top100. Here’s how they got there.
A foot in the door
The best way to get a real estate fortune is to inherit it. At least that’s the fastest way, though it comes with its own hurdles.
But let’s say you weren’t born with a silver spoon or a portfolio of millions of square feet. Barring that, you need an in. It could come from anywhere, though obviously college is often a good start. That’s where Jeff Blau, now CEO of Related Companies, met founder and then-CEO Stephen Ross. Blau hounded Ross’s office until an assistant told him the next time the exec would be on campus. Then the student orchestrated a run-in with the master. Sam Charney so impressed the leadership at Two Trees with a grad school project about their Empire Stores development that he found himself in an internship, which soon turned into a real job.
There are fewer gatekept ways in. Falcone Group and Encore Capital Management’s Art Falcone, who came from a blue-collar New York family, got his start at McDonald’s — he went into their management training program and started operating his first franchise at 22. Now he’s a partner in the master development team for the $6 billion Miami Worldcenter.
Texas developer Sunny Bathija came from Chennai, India, in 1996 with less than $3,000 in his pocket looking for opportunity and found it in an unflashy real estate niche: gas stations. It was a long way from the Ritz Carlton he’s building today, but it put him on a fast path forward. He worked for a developer, then built his own station by 1999.
Up the ante
Of course, it’s not enough to get a happenstance introduction or a one-off opportunity. The industry icons on our list figured out how to turn their luck and skill into momentum. This is where the real work starts.
Take celebrity broker Ryan Serhant. Serhant got a big break in 2010 when he was cast on “Million Dollar Listing.” But if Serhant hadn’t actually sold — if he hadn’t turned Bravo-lebrity fame into a sales training empire with “Sell It,” gotten his name on nine-figure deals like the $178 million Lauder property in Palm Beach and built a personal brand with 3 million followers on Instagram alone — he could have been just another actor-turned-broker who did a few seasons on reality TV.
Many of the players on our list took the long way around to real estate fame and fortune. Some went project by project, hitting singles and doubles over long stretches of time. Others built each project like a waypoint on the way to a grand vision, like Donald Bren, whose master-planned communities in Southern California took decades to buy, entitle, build on and market. He now holds the key to the city of Irvine and a total of 129 million square feet in almost every asset class nationwide.
The mandate to build might not make sense to people on the outside, at least at first. Robert Reffkin’s Compass drew ridicule and ire at first, as skeptics dismissed its over-the-top spending on agent technology and financial incentives. If you want to be like Reffkin, you just ignore the hate, maintain that your company is a unicorn, relentlessly scale and tune out the noise.
Suffering cycles
When you’re building your empire, the top of the cycle feels like deserved success. The lows might feel like unjust punishments. Worse, they might destroy you. Then they might do it again. We found that the folks on the list had the stamina to survive catastrophes, sometimes several times over.
The savings and loan crisis battered Prime Group’s Mike Reschke, for example. In fact it was one of five “black swan” events he’s been through, and he’s always come out. How? He says passion, but observation suggests he just doesn’t give up. He gets back into deals he’s gotten boxed out of, even once losing control of his company and repurchasing it.
Harry Macklowe nearly lost everything in the 2008 financial crisis. He’s been pushed out of his crowning glory at 432 Park. But even at 89, he has another thing planned. Macklowe recently picked up a $49 million Madison Avenue building, piecing together air rights and Landmarks approval to close a nearly impossible deal.
Whether it’s a down cycle or an unexpected disaster, would-be real estate icons have to forge ahead. Larry Silverstein famously signed the lease on the World Trade Center just weeks before September 11. The terrorist attacks destroyed his buildings, but rather than letting them raze his company, he spent the next two decades fighting insurers, government agencies and public opinion to rebuild.
The latest crisis is still fresh on the minds of many in real estate. Players on this list like CA Ventures’ Tom Scott are still fighting their way out of Covid-induced downturns. Others on the list made their money on the lows. Jeff Greene, for one, is now a South Florida developer but came up as a “Big Short” investor, betting against the housing market in ’08.
Cement a legacy
What you leave behind is ultimately the measure of everything else. If you’re hoping to leave behind a real estate legacy, it’s a good bet to try to make that a great building.
That requires erecting, or buying, a trophy. Easier said than done, though it can pay off in spades. Look at Jerry Jones’ massive Dallas Cowboys complex in Arlington, Texas. The real estate — known as Jerry World — makes up a good chunk of the team’s $13 billion valuation.
But even for the well-prepared, big projects are rarely a sure bet. The race for a casino in New York City drove several of our pros to go great lengths without winning. Both SL Green’s Marc Holliday and Soloviev Group’s Stefan Soloviev made bets on building a casino in Manhattan only to find them dashed. (On our list, only Steve Cohen came out on top. His path to a casino near Citi Field is wide open.)
Buying a readymade trophy might seem like a more secure route to real estate laurels, but that has complications too. Look at Michael Shvo, the broker-turned-developer who spent much of the early 2020s snapping up trophies including the TransAmerica Pyramid in San Francisco.As his relationships with German backers have soured, Shvo is reportedly struggling to hang onto his prizes. And making a legacy requires keeping it.
For lifelong industry experts, it’s tempting to take a swing at a political legacy too. Real estate is deeply entwined with politics and power, so it makes sense that developers like Rick Caruso, who ran for mayor in Los Angeles in 2022, would want to try their hands at shaping policy, not just letting their businesses be shaped by it.
Onward and upward
So let’s say you got your foot in the door. You built your business, survived the ups and downs of the industry and made your mark on the skyline. Once you’ve built an empire, you can’t just let it collapse. You need an heir.
For some of our icons, legacy is about people rather than projects. Naftali Group’s Miki Naftali is building toward a future that includes his daughter Danielle. ONE Sotheby’s founder Mayi de la Vega has passed the torch to son Daniel de la Vega. Jamison scion Jaime Lee has taken the reins at her family firm, where her siblings work alongside her. And when his father Steve Witkoff was called up to the White House, Alex Witkoff was already groomed to step into Witkoff projects like One Highline.
The pressure is real, particularly for those inheriting kingdoms that have been passed down for generations. Sometimes the trick is just not to lose what you’re given. But most want to honor what came before, while carving out something genuinely their own. Look at Rob Speyer’s efforts at Hudson Yards’ the Spiral, or Arthur and William Zeckendorf’s latest tilt at 80 Clarkson.
That might mean finding someone without blood ties to take over. That’s Laurent Morali for the Kushner family. Harlan Crow also tapped a non-family CEO to run his real estate operations.
But it’s hard to give up the throne. Some of the power players on this list — including some octogenarians — don’t appear to have a plan in place for the next generation, and we’ll wait to see whether that haunts their legacies, or if they can go out on their own terms.