It is a Thursday evening in Tampa, the April air muggy and leaden. There is a modest buzz of activity along the city’s downtown waterfront. Diners, suntanned and relaxed, mill about, the men in cargo shorts, the women in sleeveless dresses, sipping beers against the backdrop of a falling sun. A few determined runners weave their way among groups of tourists idling along a two-mile path that hugs the water. The Amalie Arena, home to the Tampa Bay Lightning ice hockey team, is steps away, and the GO BOLTS signs are unmissable. The slogan is painted upon the path and on flags that flutter behind low-flying helicopters. It’s hard not to note the irony of having an ice hockey stadium in a hot, swampy city. Perhaps that’s where Tampa residents go to cool off.
A few yards inland, there are about a dozen newly built high-rise buildings, their sides gleaming. Restaurants, upscale in their decor, are ready for the evening, their maître d’s waiting, expectant smiles on their faces. Tampa’s first five-star hotel, the Edition, signals its presence with the familiar waft of its signature scent, a blend of tea and bergamot that suffuses the lobby of every hotel in the chain. All around are mixed-use complexes—residences, offices, hotels, bars, restaurants, gyms—designed in an aesthetic best described as global anodyne luxe that is increasingly popular in cities from Manhattan’s new Hudson Yards development to high-rises in Tokyo to the suburbs of New Delhi. This sixteen-block area around the city’s downtown waterfront is Tampa’s biggest real estate development in recent years. Called Water Street Tampa, it is scheduled for completion in 2027, a decade after construction started. The bet is that Tampa will become a destination for tech companies, and young, urban workers will follow, bringing business and hipness to central Florida’s often overlooked city.
“Tampa had long been a donor city of our intellectual capital to other cities in America,” said Bob Buckhorn, the former two-time mayor of Tampa. Buckhorn, a Democrat who was in the seat from 2011 to 2019, was speaking by phone from his law offices in one of the new buildings, the view a daily reminder of what he considers among his biggest accomplishments. Buckhorn ran on the campaign platform: “I’m not gonna lose my kids to Charlotte, North Carolina.”
Not long before Buckhorn became mayor in 2011, Jeffrey Vinik, a former hedge fund manager and former minority owner of the Red Sox, had decided to buy the Tampa Bay Lightning, almost on a whim, and move to the city of about 390,000 people. There, Vinik, with an estimated net worth of roughly half a billion dollars, began buying up vacant parcels of land—parking lots that had fallen into disuse, abandoned buildings—around the hockey arena, which already came with two plots, figuring they would be a good investment in Tampa’s future. He found a willing partner in Buckhorn, but they needed a big investor.
Tod Leiweke, a friend of Vinik’s, whom the hedge fund investor had hired as chief executive of the Lightning’s parent company, had an idea. For years, Leiweke had been telling Michael Larson, a powerful money manager who ran a little-known investment firm called Cascade Asset Management, about the potential of Tampa. With Vinik’s interest and the city’s support, might Larson be interested in teaming up?
Buckhorn pitched the project as an “opportunity to create a walkable, livable, workable investable district that was different than what we had seen in Tampa but transportable to other cities.” Cascade bit, he said, “partly because they saw the Tampa project as a test run to see whether this concept could work and could be replicated in other jurisdictions.”
In 2016, Cascade and Vinik started a real estate joint venture called Strategic Property Partners to invest $3 billion in Water Street Tampa. Vinik was the face of the development until 2023, when he sold his interest to Cascade, which had provided most of the funds. The first phase, which took $2 billion to build, wrapped up in 2022. Including the Edison, there are three hotels, 1,300 apartments, and an assortment of restaurants and amenities. By the time the project is done, the total cost is likely to be $4 billion. An independent report released in May 2023 said that Water Street Tampa has so far created nearly 6,000 jobs and its economic impact amounts to $520 million.
So it came to be that Bill Gates is bankrolling Tampa’s biggest redevelopment project. Cascade is a 30-year-old investment firm owned by Gates, with two goals: to oversee his vast fortune and carefully invest the money that sits in the endowment of the Gates Foundation. At last count, Gates had a net worth of about $124 billion—an amount that rivals the assets managed by many Wall Street firms—and the foundation had an endowment of about $70 billion. And Larson is the man entrusted with running it all.
The Tampa project is the latest outpost of Gates’s ever-expanding, but mostly under-the-radar, investment empire. Over the decades, Larson diversified Gates’s wealth away from Microsoft and put it into stocks, bonds, hotels, farmland, private equity, real estate, and other assets—all while keeping his boss’s name largely out of the headlines, although the firm has had to give up much of its anonymity in recent years as Gates’s ballooning wealth leaves it in search of bigger and bigger investments. As of 2023, Gates owned about 1.4 percent of Microsoft, worth about $20 billion.
“Melinda and I are free to pursue our vision of a healthier and better-educated world because of what Michael has done,” Gates once told guests at a dinner in 2014 to celebrate two decades of Larson’s service. He had special lighting installed in the living room of his mansion so that the lights glowed pink—Larson’s favorite color. He added that he had “complete trust and faith” in his money manager.1
Gates had hired Larson, only a few years younger than him, in 1994 when he was working as a bond fund manager at Putnam Investments. The son of an engineer, Larson grew up in North Dakota and graduated from high school at the age of 16. He attended Claremont McKenna, a liberal arts school in Claremont, California, graduating with a degree in economics. By 21, he had obtained an MBA degree from the University of Chicago. After an initial stint as a mergers and acquisitions banker, Larson joined Putnam. Bert Early, a former executive director of the American Bar Association who ran an executive search firm, put the two in touch.
Larson wasn’t Gates’s first money manager. Not long after he had become a billionaire after Microsoft went public in 1986, Gates had hired a close friend, Andy Evans, and his wife, Ann Llewellyn, to invest some of his money for him. The couple had founded a brokerage firm called Evans Llewellyn Securities in 1980 that bought and sold mostly high-tech stocks. In 1993, The Wall Street Journal reported that the couple were convicted felons who had served time in prison for committing bank fraud.2 The article described how Evans got into a scrap with regulators for alleged securities violations. Having pleaded guilty, they had been sentenced to prison for six months. Gates even visited his friends in prison, according to the Journal story. After the rash of bad publicity forced Evans to quit as Gates’s money manager, the Microsoft cofounder apparently decided that his financial affairs should be conducted in near total secrecy. He needed someone who could invest his swelling fortune for him, and also manage the assets of the foundation, without bringing attention to any of the deals or tainting his reputation.
From the start, Larson understood the nature of his job. He even picked the name “Cascade” because it was the most generic name he could find in the Pacific Northwest, he told Fortune magazine in a rare interview in 1999.3 A big part of Larson’s mandate was to invest in a way that kept the spotlight on Gates’s philanthropy rather than his investments, according to people who have worked at Cascade. Larson avoided splashy moves. He pursued opportunities with the utmost discretion, often creating shell companies to hold Cascade’s investments. “Avoid all headlines, that was the driving culture there,” said one former employee who worked at Cascade for more than a decade.
Based out of a nondescript office building in Kirkland, Washington, about 10 miles east of the Seattle headquarters of the Gates Foundation, Cascade employs around 150 people who work on various investment strategies set by Larson. The culture of secrecy at Cascade was emphasized by the fact that Gates’s name wasn’t on any employee’s business cards or the office. When meeting with prospective investment partners or sellers, employees were instructed to say that they worked for a small money manager based in Kirkland. The vagueness was also necessary so that a seller wouldn’t try to charge a premium for an asset because Gates was the buyer. The commitment to secrecy was so high that even though Cascade had hired the small business group at Microsoft to handle its technology, most people in that division didn’t know the owner of the entity whose technology they were servicing. Employees and others who worked with Cascade were required to sign nondisclosure agreements, which were often strict and expansive. “Most of the people hired were young people, just out of college, so the fear was there, that Bill is going to sue you if you talk about any of this,” the former employee said.
Occasionally, glimpses of the vast nature of Gates’s holdings would slip into wider view in unexpected ways. In 2015, an onion grower at Stanley Farms in Georgia got into trouble after rival farmers accused it of passing off regular yellow onions as Vidalias, which are a unique type of the allium that can only be grown in a certain part of the state. The farm, which sat on land owned by Gates, was put on probation after the alleged fraud came to light, and although it didn’t pay a fine, it lost $100,000 in spoilage during a probe by the state, according to Bloomberg.4
When Larson joined in 1994, he created Cascade to manage the former couple’s personal fortune. In 2000, after Gates stepped down as the chief executive of Microsoft, the two foundations that he had created in the 1990s merged to form the Bill and Melinda Gates Foundation, and he began directing billions of dollars’ worth of his shares into it. The entity that oversaw Cascade and the foundation’s assets came to be called Bill Gates Investments, updated in 2015 to Bill and Melinda Gates Investments to reflect her growing role. In June 2021, after Gates and French Gates got divorced, the BMGI name was retired, and the umbrella entity is now called Cascade Asset Management—the overseer of both Gates’s money and the endowment funds. By many accounts, Larson has been a successful steward of Gates’s fortune. It is difficult to assess how his portfolio has performed, given the dearth of publicly available data. However, the performance of the foundation’s endowment provides some clues because the stock portfolio Larson manages for it doesn’t differ too widely from the stocks he invests in with Gates’s personal fortune. Charles V. Zehren, a spokesman for Larson, said the Gates Foundation endowment has outperformed the S&P 500 stock index.
Cascade is a type of firm that has become popular in the past couple of decades among wealthy individuals. Called family offices, such firms are unregulated entities that invest the fortunes of billionaires. Traditionally, many wealthy people used external wealth managers at banks and other firms to run their money for them. But as wealth has grown, and new fortunes have been made, many billionaires have sought to create family offices to run their investments, and sometimes their philanthropy. Depending on the owner’s wealth and ambition, a family office can be a small affair with a handful of employees. Or it can be like Cascade, which essentially operates like a sophisticated Wall Street firm, using hedging techniques to protect investments, combining short- and long-term strategies across multiple classes of assets, making direct investments, or coinvesting with others. Larson started with around $11 billion to manage. Adding up Gates’s personal fortune and the foundation’s endowment, Larson today directs close to $200 billion in investments. Although it is small compared to giant asset managers like BlackRock and State Street, which manage trillions of dollars, Cascade would be on any list of the industry’s top 100 firms given its size.
Larson adopted a more conservative investment strategy popular with family offices, where the preservation of capital was paramount. Families don’t often want to take too many risks with their money, so they are willing to settle for steady returns. Larson embraced Warren Buffett’s style of investing, an approach known as value investing. Value investors buy stocks that are underpriced relative to their intrinsic worth and hold them for the long run. He bought stocks of the kind of unfashionable but sturdy companies—from trash haulers to railways to makers of agricultural equipment—that Buffett has long championed. Cascade holds large positions in brick-and-mortar companies like the railway Canadian National, the trash hauling service Republic Services, and equipment maker Deere. There is a clutch of other investments, including small energy holdings, such as an unregulated Texas power company and Otter Tail Power, a Minnesota-based coal-burning power plant. In 2021, it teamed up with Blackstone and Global Infrastructure Partners to buy Signature Aviation, a company that provides aircraft maintenance and hangar services, for $4.7 billion. Cascade had first invested in Signature in 2009 and controlled 20 percent of the company at the time of the deal. As it has grown larger, Cascade has had to look for bigger opportunities to put Gates’s money to work, signing up for deals like the Tampa real estate complex, but more than half of Gates’s personal investments remain in stock. After the divorce, Cascade transferred billions of dollars’ worth of shares in companies like Coca-Cola Femsa, Grupo Televisa, and Canadian National to French Gates, who now has other investors managing her wealth. Cascade isn’t a big investor in private equity, which is generally considered a risky category where the payoffs can be huge, but investors could be stuck with big losses or poor returns. However, the firm has invested alongside Silver Lake because Roger McNamee, a founder of the technology investment firm, knew Gates. In the past, McNamee has referred to Larson as the “Gateskeeper.”
One of Cascade’s oldest and highest-profile investments is its 75 percent ownership of the operating company behind Four Seasons, the hotel brand synonymous with luxury. The hotel company, founded by Isadore Sharp, opened its first Four Seasons in downtown Toronto in 1961 and followed an innovative business model. While the hotels could be owned by individuals or companies, Four Seasons would operate and manage them based on their stringent standards, offering travelers a consistent and luxurious experience at Four Seasons hotels around the world. Cascade had first invested in Four Seasons in 1997 when it was a public company. A decade later, Cascade teamed up with Kingdom Holding Company, the investment firm of Saudi prince Alwaleed bin Talal, which also owned a substantial chunk of Four Seasons, to buy the bulk of the hotel operator for $3.8 billion. Sharp retained a 5 percent stake. Soon after, the stock market tanked as the financial crisis of 2007–9 led to a recession that crimped spending on luxury hotels. The partnership, though equal, was rocky in the beginning as the co-owners quibbled over strategy.5 Cascade wanted to strip costs to increase profitability, taking measures like not stripping sheets every day, but Sharp thought it would dilute the brand. Eventually, they settled on a compromise: guests could place a pinecone on their beds to indicate that they didn’t want their sheets washed every day. Cascade and Kingdom also tussled over who should lead Four Seasons after Sharp stepped down as chief executive in 2010.
Gates doesn’t typically get involved in negotiations involving his money, but he made an exception for Kingdom, sitting down for a meeting with his fellow billionaire Alwaleed in 2013 to resolve a dispute between the two sides about the direction of Four Seasons’ growth, and the two have partnered on philanthropic projects. But Four Seasons eventually recovered. In 2021, Cascade said it would take control of the operating company by buying half of Kingdom’s 47.5 percent stake at a valuation of $10 billion. It now owns more than 70 percent; Sharp continues to own 5 percent. Because of Gates’s ownership stake in Four Seasons, employees of the Gates Foundation are typically not allowed to stay at any of their hotels to avoid any appearance of impropriety.
In 2021, The Land Report tallied up all the land owned by Gates and determined that he is the nation’s largest private owner of farmland. The report, by the publication that calls itself the “Magazine of the American Landowner,” startled people because the news was so unexpected. The article, titled “Farmer Bill,” counted roughly 270,000 acres of farmland that the technology billionaire had amassed.6 Those close to Cascade have defended the land ownership by pointing out that the land Gates owns is a small slice of the 900 million acres of total farmland in America. There are other private owners of farmland with larger holdings than Cascade, including the Mormon church. (Also, Gates is not the only billionaire who sees land as a valuable investment. John Malone, the media mogul, is the nation’s largest private landowner, with 2.2 million acres, which include ranchland. More than a dozen other billionaires and their families also own ranchland and farms.)7 Gates has made it clear that the farmland investments are not part of his work on climate change but rather, a decision made by his investment team. Larson saw farmland as a valuable but limited resource that offers investors a way to hedge against stock-market volatility and inflation (Cascade is also a big buyer of Treasury Inflation-Protected Securities, or TIPS). The firm began buying up parcels of land in the early 2000s and owns those assets through layers of subsidiaries and shell companies. The ownership is structured rather like Russian nesting dolls, not only to maintain secrecy but also to shield Gates from direct ownership, one person with knowledge of the arrangements said. Since farmers get large subsidies from the federal government, Larson was careful to structure the purchases so that it didn’t appear as though Gates was benefiting from government subsidies, the person said, underscoring that Gates himself did not receive or benefit from such subsidiaries. Typically, Cascade would buy both the land and the lease from a farmer and lease the land back. That way, the government subsidies went to the leaseholder, but the revenues were shared with the owner.
Cascade’s agricultural team sometimes bought farmland portfolios from other big investors. The firm also purchased farms directly from farmers, especially those in need of upgrades and new equipment such as tractors, and worked with them to improve techniques, introduce sustainable farming measures, and increase productivity, the person said. The land that Gates owns cultivates a range of crops, including soybeans, carrots, corn, and even the potatoes used in McDonald’s French fries.8
As part of his investment strategy, Larson has cultivated a network of money managers and other investors to source new opportunities and stay looped into the financial world. He organizes conferences, and a lot of people stop by to meet him at Cascade. From time to time, Gates himself brings Larson investment ideas since he is constantly in touch with people from a range of backgrounds, from electric vehicles to farming techniques.
The two meet at least once every month or two to discuss the state of Cascade’s portfolio, but the larger investment group gets to meet with Gates—and while they were married, French Gates—once a year at an all-day meeting. Employees present investment updates and highlight the mix of assets in the portfolio. Sometimes, big Wall Street investors stop by. David Bonderman, the private equity investor, and Bill Miller, the asset manager, have been past guests.
For seven years, Bob Sydow had managed about $1.6 billion for his asset management firm’s only client: the Gates Foundation. His firm, Grandview Capital, invested a small portion of the foundation’s endowment in the high-yield bond market. But one day in February 2006, Sydow was abruptly dismissed. His firm’s relationship with the foundation had been terminated overnight. As he struggled to find new clients, Sydow found that he had become a pariah in the asset management industry. People refused to work with him unless they understood why the Gates Foundation had kicked him out. And when there was no explanation forthcoming, the possibility that Grandview had done something criminal made potential clients wary. It was impossible for him to start a new business. Sydow had become “untouchable,” they said.
Sydow described his ordeal to Gates and French Gates in a six-page letter dated November 3, 2006, having spent most of the year trying to drum up new business and salvage his reputation without making any headway. His goal was to alert them to the behavior of Larson. “I really do believe you have an agent there with the potential to greatly embarrass both you and the Foundation,” Sydow wrote. Although the letter was addressed to both, it was sent to separate addresses—Microsoft headquarters for Gates, and Watermark Estate Management Services, the entity that handled the couple’s family matters, for French Gates. Sydow believed that Larson had cut him off out of spite. The two had been close friends for 24 years, he wrote, and he had even been godfather to Larson’s firstborn child. Yet after Sydow told Larson that he needed to stop using his power to hurt people, Larson decided to stop using Grandview’s services. Zehren, Larson’s spokesman, said it was within Larson’s right to terminate the services of external money managers based on their performance, or because he wanted to change the mix of investments. Larson also said, through Zehren, that Sydow is not godfather to any of his children.
To some who worked for Larson, the Sydow incident was no surprise. A heavyset man who liked to dress in pink shirts and once sported a hairstyle that channeled the bangs of Johnny Depp, Larson largely ran Cascade as he saw fit for years, with complete control and few procedures in place. He often recruited young employees straight out of college, including from his alma mater, Claremont McKenna, and didn’t see the need for human resources staff. He would sometimes reward people with new job titles before yanking them at will, causing confusion. To many, he came across as imperious, rude, and threatening. More than a dozen people who worked for him over the decades said Larson was a demanding boss, prone to fits of rage, who occasionally mistreated his subordinates. Zehren said Larson only ever stressed the need for high-level performance. Some employees witnessed Larson judging female employees on their attractiveness. At least once, he made a racist remark. On Election Day in 2004, Larson asked his office colleagues about the best time to go vote. When a young employee, Stacy Ybarra, who is Black, replied that she had voted that morning without waiting in line, Larson responded: “But you live in the ghetto, and everybody knows that Black people don’t vote.”9 That year, he also shorted the stock of Infospace because Ybarra told him she was leaving to join that company. It was apparently out of spite. Zehren confirmed that Larson did bet that the stock of Infospace would fall—and made money on the bet—but denied that he acted out of spite, calling it an “outright lie.” He also said that Larson denied making a racist comment, and that any claims alleging racial or sexual harassment against him are “flatly untrue.” Larson was proud of his “long-standing efforts to promote equality and diversity,” both at Cascade and at the various companies in which Cascade invested money.
When Dorrise Kalbfleisch joined Cascade in 1998 as the firm’s fifth employee, to oversee its tax and accounting practices, Cascade had the feel of a “garage band,” she recalled a colleague saying. By the time she retired in 2022, Kalbfleisch said, the firm had become a much more professionally run organization, which the same colleague dubbed a “rock band.” The changes were spurred partly by complaints about Larson’s behavior; partly because Cascade had grown to about 150 people, making management unfeasible for Larson; and partly because of the recognition that he was a better investor than people manager. Larson dealt with a much smaller number of people, and there were more management layers and a stronger effort to recruit people of varied backgrounds. In 2021, for the first time in its existence, Cascade had a website explaining what it did and how it was committed to diversity and inclusion.
Larson’s initial make-it-up-as-you-go-along approach would probably have invited less scrutiny had Cascade remained a small entity with just a handful of people. But as he began to diversify Gates’s fortune away from Microsoft, the firm had to hire more people—lawyers, tax and regulatory experts, investment analysts, IT specialists and others—to carry out its work, like any sophisticated investment firm. At the same time, there was little initial thought given to building the supporting infrastructure common to professionally run entities, such as staff to hire and recruit people, help employees plan careers, and provide feedback and monitor their well-being.
Larson’s personality, which friends and foes alike have described as brusque and direct to the point of rudeness, and his lack of sensitivity and tact, were thus on full display, especially because he insisted on a largely flat organizational structure. Kalbfleisch, the early employee and a personal friend of Larson’s, described him as the kind of boss who would think nothing of berating someone in front of others. Once, he hit “Reply All” to tell her she was not qualified to address a tax matter, she recalled, prompting her to go into his office and tell him never to do that again. At the same time, Kalbfleisch found him considerate and compassionate. Larson was someone who “cared about things like benefits and compensation, and if an employee had personal challenges, he would get involved, and if someone left, he would also help people get jobs.”
At some point, because of various complaints about his style of communication and unpredictable behavior toward staffers, the question came up of what to do. One decision was to introduce physical distance between Larson’s office and the rest of the employees by moving some of them to a different floor, but that “didn’t change his behavior, it just changed the location of where the behavior happened,” a former longtime employee said. “It happened through emails.” Some employees took to calling those emails “Larson bombs.” Kalbfleisch remembered them as “e-bombs,” and added that as far as she knew, the office spaces were reorganized to accommodate new hires. He had some fans, including one who joined Cascade in 2016, worked there for three years, and thrived in its “no-wuss culture,” which she said was very different from the general “please-and-thank-you culture” of many Seattle workplaces. Larson acknowledged, via email, that he had once been abrupt and demanding, but said it had never been personal. “Years ago, in my career, I used harsh language that I would not use today,” he wrote, adding that he had since done “a lot of work to change.”
In 2021, The New York Times reported that there were at least six complaints against Larson about his behavior, including four from Cascade employees; at the time, another spokesman for Larson said there were “fewer than five complaints” over the years. Zehren reiterated that reports of complaints were “flatly untrue.”10 Settlement payments were made to half a dozen employees, who were forbidden from speaking about their time at the firm, The Times reported. Such nondisclosure agreements are not unique to Cascade, and many complainants who settle with their companies behind closed doors sign them in exchange for a payment. But many who did sign Cascade NDAs said they were so expansive as to prohibit employees and external managers from talking about their employer, Larson, Gates, French Gates, and even the Gates Foundation. Similar NDAs were also required of senior executives elsewhere in the Gates universe. Lawyers for Cascade have sometimes called people who they thought had broken their NDA and threatened to sue. On their way out, many former employees told Gates and French Gates about the culture that Larson had created. Even though Gates was aware of Larson’s conduct, he often seemed to approach complaints with a “get rid of it” stance rather than try to change the culture at Cascade or issue a severe reprimand his money manager, according to several former employees. The takeaway for some employees was that as long as Larson was preserving the fortune, doing a good job managing the foundation’s money, and avoiding bad press, he was free to do as he pleased. About fifteen years ago, Cascade began introducing more traditional HR training programs, including “processes, policies, procedures,” performance reviews, and even an anonymous reporting hotline, Larson’s spokesman said. Kalbfleisch said that over the years, Cascade also brought in many consultants to conduct internal surveys, “but you wouldn’t get the feedback, you wouldn’t be hearing the things you needed to hear about the culture and environment. People weren’t necessarily honest with what they thought, so that didn’t help.”
Zehren, the spokesman, who did most of the talking for Larson, denied that Larson built Cascade as anything but a welcoming, open, and considerate place where people were encouraged to speak up. Larson has built a “world-class organization with strong governance for the past three decades” with the help of talented managers and HR professionals, he said, and credited Cascade’s flat organizational structure, free of rigid hierarchies, for the firm’s successful track record. “Cascade is an organization where anyone, no matter their professional position, feels free to present ideas that make the group and its investing performance better,” Zehren said. Larson also vehemently disagreed with the portrayal of him as rude and domineering. Through Zehren, he provided the names of several people who could provide another perspective, including two whom he had nominated to the board of Republic Services, one of the country’s biggest waste disposal companies. Cascade owns more than a third of Republic Services and is its largest shareholder, and Larson is also on the board.
Tomago Collins, one of those directors and a longtime friend of Larson’s, said he was wowed by the breadth and depth of his friend’s relationships with everyone, from managers of sports teams to fellow investors. Collins was also struck by the genuine interest Larson took in young people’s careers, whether they were holders of MBAs from Ivy League universities or restaurant servers, offering them advice if he thought he could be helpful. “I’m not used to people that successful giving advice to other people,” said Collins, who sees Larson about half a dozen times a year. He added that he has never seen Larson do “anything hurtful or harmful,” either in social or professional settings. Collins, an executive in the sports and entertainment industry, is also on the board of Four Seasons as a representative of Cascade, which is the luxury hotel company’s largest shareholder.
“He’s different, he’s a savant, wicked smart, he’s taught me a ton,” said Jennifer M. Kirk, another director of Republic Services whom Larson brought on when he was looking to diversify the board by gender, color, and thinking. Kirk, a senior executive at Medtronic, the medical device company, called Larson a “mentor of sorts.” Kirk, who’s in her forties, found that he grasped how younger generations think about companies beyond profits, and he peppered her with questions about her young children: “What do your kids drink, Jenn? Do they like those energy drinks, do they drink soda?” In her interactions with him, which were mostly professional, Kirk found him direct but never disrespectful. “He’s not a long-winded guy,” she said, adding that one-word emails from Larson were more about efficiency than rudeness. Kirk mused that in general, the directness that was off-putting to many was almost a cultural aspect of certain industries like banking, of people who are “smarter than the average person” and expect them to keep up. Kalbfleisch agreed; she found Larson bright but “lacking people skills, like a lot of investment people. He just didn’t think about it.”
To people like Collins, Kirk, and others, especially those outside Cascade, Larson can be personable—someone whose directness is part of the persona, as is his capacious mind, which they said harbors information as wide-ranging as the mechanics of wine production and the performance statistics of sports teams. “He’s his own walking Wikipedia and LinkedIn,” said Mike Jackson, the former chief executive of AutoNation, the automotive retailer, and a longtime friend of Larson’s. “He travels incessantly, he works like crazy and then at the end of the day he’s highly principled. You want to talk sports, he can do sports, you want to talk farming, he can do farming, or exchange rates,” Jackson said in an interview conducted for a profile of Cascade that ran in The Wall Street Journal in 2014. “About the only thing he stays away from is technology. He says, ‘It’s Bill’s.’ I cannot tell you how curious this man is about anything and everything, all day long.”
It takes a village to raise a child. It also takes a village to support a billionaire’s interests and activities. More than 2,000 people depend—directly or indirectly—on the Gates fortune for their careers and livelihoods. Most are at the Gates Foundation, whose salaries and benefits are paid for by Gates money that has been earmarked for charity (and cannot be claimed back by the billionaire under tax laws). In 2019, the foundation spent around $300 million on salaries and benefits for its employees. Some 200 people manage his family’s homes, horse farms, meals, security, jets, travel, and lifestyle through a company called the Gates Family Office, formerly known as Watermark. Another 150 or so people are employed by Cascade. Gates Ventures, the billionaire’s private office and investment firm, has at least 80 people. There are yet others who work at Breakthrough Energy, also a venture capital firm founded by Gates that focuses on sustainable energy solutions.
Many of the people who work in the Gates orbit circulate between the various entities the billionaire is associated with. The foundation’s first two chief executives came from Microsoft; Jeffrey Raikes, who held the chief executive’s job from 2008 to 2014, is also a close friend of Gates. Larry Cohen, the chief executive of Gates Ventures, is a former Microsoft executive. Nathan Myhrvold, Microsoft’s first chief technology officer, is a longtime friend and ally in whose patent firm, Intellectual Ventures, Gates has invested. It’s hardly unique for the world’s uber wealthy to have armies of people around them. From philanthropy advisors to personal chefs, entire industries exist to channel the largesse and serve the whims of the rich. Gates’s activities continue to expand steadily, as a universe does, requiring more staff and holding companies. Although Cascade remains at the heart of the Gates financial engine, the billionaire has for years made personal investments through Gates Ventures. It was essentially a vehicle through which Gates indulged his passion for new, experimental technologies, making small, venture capital–style investments in things like synthetic meat and Alzheimer’s research. Through Gates Ventures, he provided seed money to Ambri, a liquid battery metals manufacturer cofounded by an MIT professor whose online curriculum Gates had followed. It houses Gates’s stake in Myhrvold’s firm, and has a line into Breakthrough Energy, which held his energy-related investments but was spun off into a separate firm that also invests the money of other wealthy individuals with an interest in the field. Gates also directs some personal gifts through the outfit. A gift of $2 million that he made to the Massachusetts Institute of Technology’s Media Lab came from bgC3, the predecessor to Gates Ventures. The gift became known during investigations into Epstein’s death.
Gates is also an investor in patent licensing firms, sometimes called “patent trolls.” His deeply held belief that intellectual property must be protected and paid for—the same belief that led him to charge for software and license Microsoft Windows to hardware makers, and the same belief that made him an arch defender of vaccine patents during the coronavirus pandemic—led him to back Pendrell, a company that typically buys intellectual property and collects royalties by licensing that patented knowledge. Such firms by nature tend to be litigious, and in recent years, Pendrell has sued companies like Apple for patent infringement. Intellectual Ventures, cofounded in 2000 by Myhrvold, a longtime friend of Gates who is also a scientist, cookbook author, and dinosaur researcher, has an innovative business model. Essentially, the firm buys patents and generates revenue by licensing the intellectual property and sharing the profits with inventors of those patents. It also acts as an incubator for inventors. Its portfolio of more than 35,000 intellectual property assets has generated more than $2 billion in licensing revenue, including $400 million for inventors. Myhrvold alone holds 900 patents and some of his technologies have been spun out of Intellectual Ventures into independent companies, some of which Gates has invested in. As of 2022, the firm had spun off 15 companies including TerraPower, a nuclear technology company. Intellectual Ventures also ran a fund called Global Good, created by Gates and Myhrvold to focus on developing technologies to solve “some of humanity’s most daunting problems.” The fund works with commercial, research, and government partners to bring new technologies to market.
Breakthrough, the energy firm “dedicated to helping humanity avoid a climate disaster” that Gates founded in 2015, invests in companies that are working toward clean technologies with the goal of reducing greenhouse gases and getting to net zero emissions. Since 2017, the firm has invested in more than 100 companies. Breakthrough has raised at least two funds, which collectively hold more than $2 billion. There is also a smaller, Europe-focused fund. Gates is by far the largest investor in Breakthrough, but there are more than three dozen other investors, mainly businessmen and -women from all over the world, including those that many Americans likely haven’t heard of, such as Patrice Motsepe, a South African mining billionaire. One had to be a billionaire to invest in a Breakthrough fund; they were not intended for less wealthy people who might seek returns on investment and other specific performance-based targets, said one person with insight into the funds’ setup. It was yet another example of the billionaire using his star power and influence to push toward things he thinks are for the general and societal good.
Then, there is the sprawl of the Gates family life, and the range of services and the efforts that go into lifestyle upkeep. Like many in the billionaire class, Gates owns multiple homes around the United States. Those alone add up to about $300 million. During their 27-year marriage, the primary home of the former couple, the place where they raised their children, Jennifer, Rory, and Phoebe, was the high-tech mansion, nicknamed Xanadu 2.0, located on the shores of Lake Washington in Medina. Originally intended as a high-tech pad for Gates before he married, the home took six years to build and was last valued at $130 million. Gates kept the mansion as part of the divorce settlement. Other homes the ex-couple own or have owned include a beachfront mansion in Del Mar, California, just north of San Diego, worth at least $40 million; a six-bedroom home in the Vintage Club in Indian Wells, California, assessed at $12.5 million, and a horse farm on 5.5 acres in Wellington, Florida, a popular spot for the horse-riding set, that sold for $26 million in 2022.11 There is also a Gates family vacation compound with multiple houses in the Hood Canal area of Washington State.
Gates is famous for his love of fast cars, having gotten a speeding ticket in 1977. Over the years, he has indulged in luxury wheels, from Porsche Taycan 911s to Ferraris and Mercedes Benzes to a Tesla. He owns at least two customized planes, including a Gulfstream, which are known to cost at least a couple of hundred million dollars. There are helicopters and sea planes for short distances. The $30.8 million that Gates paid for his Leonardo da Vinci Codex in 1994 remained the highest price for a document bought at auction until 2021, when the hedge fund billionaire Ken Griffin purchased a rare early print of the U.S. Constitution for $43.2 million.12 Gates’s art collection includes works by American artists, among them an 1885 oil painting by Winslow Homer that Gates bought for a reported $30 million.
Watermark—now renamed the Gates Family Office—which for years managed the Gateses’ personal assets, has had on its payroll, at various points, project managers, financial planners, a coordinator for “gifting,” a recruiter, as well as real estate managers and travel and logistics experts, among other professionals. There is a chief of “protective operations” with a background in counterintelligence and special investigations; not only do security personnel constantly tail Gates family members, but they are also required for the protection of dignitaries who visit the Gates mansion. An event planner, an “interiors” specialist, a horticulture program manager, stylists, personal shoppers, audio and video specialists, and even a professional to train people in business etiquette are or have been on staff. As of fall 2022, the family office also employed a professionally trained private chef with experience working on yachts, islands, and estates, practiced at all styles of cuisine and dietary preferences.
Although the Gates Family Office no longer handles French Gates’s personal affairs, it was once in charge of managing her wardrobe, makeup, and hair, and styling her. The office staff also has included an expert in rare books to catalog their collection, experts in “chemical-free” housekeeping, tennis, golf, boating, massage, yoga, meditation retreats, and riding golf. The family office is also the primary entity through which Gates holds interests in equestrian properties for Jennifer, who is a professional show jumper and doctor. The portfolio also includes ranches and horse barns, including its remaining properties in Wellington, Florida—known as horse country for its miles of bridle paths—not far from Equestrian Village, site of the U.S. Dressage Festival for many years, and the equestrian grounds for Palm Beach. At one point, entities tied to Gates through the family office bought up properties on an entire street in Wellington totaling 16.5 acres to ensure privacy and security.13
Kalbfleisch, who worked with the estate manager of the Gates household, lending her accounting expertise to do the budgets in addition to her duties at Cascade, remarked dryly that the more the uber wealthy acquire, the more they need. “First there is one residence, and then you buy a second home and multiple homes, and then you want to make sure that you replicate all the things you need in every home, and that requires budgets and staff,” she said, speaking generally. “Then your kids are born, and you need additional staff. And in the beginning, there was one plane, one pilot and one backup pilot, but there came a second plane. You need someone on staff to walk the dogs, handle the personal affairs, like property taxes, charitable donations, and then the family protection and security, and making sure everything worked smoothly.”