Real Estate Titans

Lessons from some of the great real estate investors?

In 1992, Blackstone recruited Barry Sternlicht to lead its real estate business. “We had agreed on terms,” recalled Blackstone’s John Schreiber, “but at the last minute, he changed his mind.” Instead, Sternlicht built Starwood, which would become one of Blackstone’s biggest competitors.

Sternlicht’s first act was a masterclass in value creation. Launching Starwood in 1991 with just $20 million, he built it into a 1,300-property empire that ultimately sold to Marriott for $13 billion in 2016. Now, he is betting that lightning can strike twice, reviving the Starwood brand with a more focused, boutique approach. The question is whether he can replicate his past success in a vastly different hospitality landscape shaped by new consumer preferences, alternative lodging platforms, and shifting capital dynamics. Sternlicht isn’t just a real estate owner—he’s also a lender. His firm, Starwood Property Trust, is one of the largest publicly traded mortgage REITs, making him a major player in real estate finance. His influence extends beyond bricks and mortar; he understands the financial architecture that underpins the industry. Sternlicht has built his career by anticipating and responding to changes in the way people travel and stay.?Others, however, have had to rethink how and where people work.

Consanguinity isn’t uncommon in the real estate industry, Greystar emerging as a sister company to Starwood. Following Harvard Business School, Bob Faith began his real estate career with the Trammell Crow Company in 1986, ultimately becoming a Partner. In 1991, he co-founded Starwood Capital Partners alongside his school mate Barry Sternlicht, before exiting in 1993 to found Greystar Real Estate Partners, LLC, in Houston, Texas.

Erez Cohen in his book ‘Real Estate Titans’ interviews Faith, who reflects: “Back in the 1980s, when I graduated from Harvard Business School, a company could borrow from a financial institution up to 105% over the development cost. The extra 5% was just so we could pay ourselves. That business plan lasted until the savings and loan crisis of the early 1990s hit, smashing just about everyone in store in the entire U.S. market… Whenever there is a market shift, the real estate market enters the phase of “adapt or die”. We had no choice but to adapt. I had to raise private money, which was something new for me… People often asked how I was able to raise money in 1991 when no one else could... Fortunately, an old friend from business school managed some of the money for the Vanderbilt family. His strategy was to bring in money and meet someone who knew an industry and was willing to sweat and do the hard work. I started off as the sweat equity partner, which is what everyone entering the real estate business can do - find amazing deals that they could never acquire on their own and bring them to investors.” This is the modus operandi for many real estate operators, then and now.

Faith’s mentor was Trammell Crow’s Chairman Emeritus and retired CEO of Trammell Crow Residential, Ronald Terwilliger. In ‘Real Estate Titans’, Cohen also interviews Terwilliger, who advises: “The key to responsible financing of apartment developments is to keep construction debt to 75% of cost or less and have construction loan maturities that are long enough to get you through a recession.” Other similar sage advice included “When investing in any project, focus on the downside before looking at the upside. Ask yourself “what happens if this deal goes bad?”

Terwilliger emphasises the importance of developing a core competency in real estate, especially early?in one’s career. He notes that companies restricting development to a single product line, such as rental apartments, can develop deep expertise in financing, design, and construction. To mitigate risks associated with local markets, Trammell Crow partnered with local developers who possessed deep regional knowledge. This strategy balanced geographic diversity with local insight, allowing the firm to scale effectively.

Known to insiders as the “whisperer”, Roy March, CEO of Eastdil Secured, also exemplifies the ability to spot opportunity in a changing real estate landscape. His journey began with a detail as small as a brochure. The branding of Eastdil’s brochure appealed to March’s aesthetic, prompting him to apply for an internship at Eastdil in 1978. On his first day, he bumped into founder Ben Lambert outside the restroom, who gave him two pieces of advice: “Eastdil Realty has the God-given right to every piece of business in the universe—now go earn it.” And, “Never leave a meeting without asking for the order.” March’s sharp instincts and confidence propelled him through the ranks, transforming him from an ambitious newcomer into the leader of the world’s largest independent real estate investment bank. His ability to structure complex deals and navigate evolving market cycles mirrors the thinking of Bill Gross, co-founder of PIMCO, who has long emphasised the importance of understanding financial architecture.

Gross, reflecting on his decades-long investing career, recognises that with age comes perspective. The publication last year of his nearly comprehensive Investment Outlook essays, spanning back to the late 1970s, provided him with an opportunity to step back and distil the deeper lessons that remain relevant today. His reflections extend beyond market predictions to the fundamental principles of successful investing. One of the most crucial, in his view, is the interplay between leverage and time. While leverage can be a dangerous tool, its risks diminish when paired with a long enough horizon for sound investment ideas to unfold. Warren Buffett exemplifies this principle, using the stable capital base of Berkshire Hathaway’s insurance businesses to reinforce his long-term investment strategy. The permanence of insurance premiums and long-term debt stands in contrast to the short-term fragility of hedge fund capital, as evidenced by the collapse of John Meriwether’s Long-Term Capital Management. Gross sees Buffett not only as a brilliant investor but as a master financial architect, demonstrating that time is an essential dimension in financial success.

If Gross’s philosophy highlights the power of patience, Byron Wien’s career (vice chairman of Blackstone Advisory Partners) underscores the value of originality. Wien believed that in investing, business, and life, the key to lasting success is differentiation rather than superiority. There will always be someone smarter, faster, or more technically skilled, but imagination—the ability to see opportunities others overlook—can be a far more sustainable advantage. He discouraged competing on conventional metrics and instead urged investors and executives to cultivate originality. In an industry where consensus thinking dominates, independent vision is often the rarest and most valuable asset.?

A long-term perspective has allowed New York City’s most enduring real estate families to thrive across generations. The Rockefellers, LeFraks, Rudins, Dursts, and others have not only built and transformed the city’s skyline but have left an indelible mark on its economic and cultural fabric. Their influence has persisted through market crashes, shifting political climates, and waves of urban renewal, not because of wealth alone, but because of their ability to adapt. From John D. Rockefeller Jr.'s development of Rockefeller Center in the 1930s to the Rudin family’s modernisation of Manhattan’s office stock, these dynasties have navigated real estate cycles with vision, patience, and strategic reinvention. While some, like the Milsteins, expanded aggressively into finance, others, such as the LeFraks, built entire communities like Newport, New Jersey. What unites them is an understanding that real estate is not merely about transactions but about shaping the city for future generations. Like the investors, dealmakers, and executives before them, they have demonstrated that success is ultimately a function of time, strategy, and the ability to see value where others do not.

?Adaptation and reinvention are themes not confined to real estate. In creative fields, too, late bloomers have often outperformed those who started early. Vincent van Gogh, was told at the age of 28, “You are no artist... You started too late.” Almost every one of his masterpieces was painted in the last two years of his brief life. Genius, in many cases, emerges not from an early start but from persistence, reinvention, and timing. David Epstein, in his book ‘Range’, argues that we underrate the process of exploring the world to find the right fit. He cites research by economist Ofer Malamud, comparing the Scottish education system, where students specialise late, to the English and Welsh system, where they specialise early. While English and Welsh students got off to a faster start, they were more likely to realise later that they had chosen the wrong path and had to begin again. The Scottish model—deliberate, unhurried exploration—may seem like an indulgence, but it often leads to better long-term outcomes.

This theme of adaptation and discovery resonates deeply in real estate. Some of the industry’s greatest successes—Sternlicht, Faith, March, and Gross—were not defined by a single early decision but by their ability to evolve, reposition, and capitalise on new cycles. Just as the real estate dynasties of New York built their legacies not through rapid wins but through generational foresight, today’s visionaries are shaping the future by balancing expertise with flexibility; structure with creativity; and patience with conviction.