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Fortune
Fortune
Shawn Tully

How a 28-year-old dealmaker jump-started an industry and became one of Wall Street's youngest CEOs

Matt Swain of Triago in a helicopter. (Credit: Courtesy of Triago)

In June of 2022, a 27-year-old investment banker named Matt Swain was seated in Sam Zell’s private dining room overlooking the Chicago River, listening to the famously tough-talking real estate legend express his fresh doubts about a deal. 

Swain was a kid by dealmaking standards, and not a comer from Goldman Sachs or Morgan Stanley, but a money-raiser for Triago, a French firm little known on Wall Street. Swain had helped persuade Zell to take a majority stake in the $129 million purchase of Entertainment Earth, a manufacturer of such showbiz collectibles as Star Wars action figures. But Zell—upon learning that EE was losing key contracts— told Swain he was getting nervous. And to salvage the transaction, the Manhattan-based Swain made an emergency mission to Zell’s Second City office. 

Swain found the setting as quirky and offbeat as his fabled host, who passed away earlier this year. When he inquired about the pair of ducks splashing in the adjoining terrace pond, Zell explained that when not swimming, his aquatic favorites trod heated floors that he’d specially installed for their comfort. “The ducks aside, Sam was cheap, but in a smart way,” recalls Swain. 

Given his newfound worries about EE, Swain recalls, Zell wanted to lower the base price he’d first agreed on. He also sought to reduce the profit participation of the “sponsors”—the team of operational experts who had found the opportunity and would run the company. But Zell wanted to craft a new deal featuring a distinctive structure. “If the new managers did a fabulous as opposed to medium job in raising EE’s value, he’d pay them a lot more than the original number for the company,” Swain explains, “and reward the team with a much bigger share of the gain.” 

For Zell, success was all about setting the right incentives, gauged to making the people you back rich if they win big, and face the abyss if they flop. Observes Swain, “Sam would say, ‘When the guy has to tell his wife they’ve blown their life savings, or that she can’t have that dishwasher ‘cause he’s failed, then I know he’ll perform for me!’” 

Swain—who was young enough to be Zell’s great-grandson—reassured the then 80-year-old mogul by pledging to invest several hundred thousand dollars of his own savings towards the EE purchase. “Sam said that he loved that I was putting skin in the game, too, and that it gave him extra comfort,” says Swain. He reassured Zell that the “worse downside, huge upside” tilt would appeal to the selling family. He was right. Zell won his pay-for-performance package, and he bought EE. 

Swain, meanwhile, added to his ever more impressive track record of brokering so-called direct-transaction private investments, or “directs”. It’s a financial niche whose huge upside has lured a growing number of affluent investors, while helping Swain build an outsize reputation and earn a Wall Street CEO seat, all in his first few years out of college.

The fast-growing, lucrative field of 'directs'

All told, Swain arranged three purchases in just over two years for Zell’s private investment arm, EGI, including the $520 million spinout of DuPont’s clean technology branch, Elessent. All of those deals fall under the high-promise specialty that Swain has done more than any other figure to grow and promote in recent years. 

Matt Swain, Sam Zell, and Antoine Drean.

In direct deals, family offices, asset managers and other investors purchase entire companies that they hand-pick, one at a time, with no private-equity funds involved. The entities that put up the money exercise full control in assembling their own, tailored portfolios of individual enterprises. It’s the investors who make the bets, based on their assessments of prospects for individual companies.   

It's still “private equity,” but it’s a totally different game from the mainstream version, where a pension fund or endowment commits hundreds of millions or billions of dollars to one of the huge funds, pools that can reach $30 billion run by the likes of Ares or Carlyle. The managers then deploy that capital to buy, say, ten companies they have full freedom to choose. (The funds’ investors, in contrast, usually have no say in the enterprises comprising the portfolio.)

Compared to regular private equity, direct deals pay fees that are far more skewed to performance. They typically involve smaller companies, purchased for equity stakes of $50 to $500 million, that can reach full enterprise values of $100 million to $2 billion (including debt). These companies are also typically fixer-uppers that command far lower prices than what the PE giants pay for bigger, smoothly running choices. 

The directs model fit right into Zell’s duck pond. “Sam hated big PE funds because the fees were too guaranteed and not tied enough to results,” notes Swain. “He thought the situation was just the opposite for directs, where he and his team could use their experience to create value.”

Deals for hungry family offices

Today, the biggest backers of direct transactions are family offices—a golden realm that has grown its assets more than any other private investment category in recent years. EY reports that the number of the number of these investment havens for the world’s wealthiest clans has expanded ten-fold to over 10,000 since the early 2000s. And according to an estimate from researcher Campden Wealth, their assets under management now total around $6 trillion, a figure that exceeds by 50% the $4 trillion parked in hedge funds as well as the estimated $4.4 trillion in private equity. 

Put simply, the builders of these mountains of capital, and their heirs, are increasingly seeking investments a lot more individualized, adventurous, and higher-yielding than what’s on offer from traditional private equity. These family offices also expect better returns than they’ve been receiving from their stakes in big PE funds. 

There’s a good chance that they’re getting those bigger numbers via direct. Over the past decade, the PE industry’s six giants—Carlyle, Blackstone, Ares, KKR, TPG and Apollo—have delivered 16.9% annually, according to research from PitchBook. Public numbers are scarce for directs. They’re the province of private holders who keep their track records secret. But a good guide to the gains in these one-by-one deals is the results for Ocean Avenue, a firm that collects direct deals into funds. Through the middle of 2021, its vehicles, the first dating from 2013, showed an average IRR of around 30%. That number is consistent with the approximate figures I gleaned from private sources involved with other direct-investing firms, in the interviews for this story.

The key players in directs: sponsors, investors, and fundraisers

Direct deals require the combined efforts of three main participants. The first are the “sponsors.” These are independent teams of operating managers whose trade is finding the deals, and who go on to manage the company after it’s acquired. In directs, instead of paying fees to a big PE fund, investors are rewarding teams that swoop down on these less-than-top performers, and labor full-time onsite to fix them. The second group are the investors who back the deals and pay those fees. For now, they’re principally those family offices. 

The final component: The “placement agents” or fund raisers. That’s Swain’s gig at Triago. The sponsors bring the deals to Triago, and Swain matches them with either one or a group of, investors he deems likely to bite. In three years, Swain’s matchmaking skills have built the world’s biggest independent “directs” franchise from scratch at the Manhattan branch of Paris-based Triago. Before Swain’s arrival, Triago on the fundraising side primarily secured capital for hedge funds and brokered limited partnerships in private equity. Building a powerhouse in directs was Swain’s ticket to earning Triago’s global CEO chair at age 27. (He’s now 28.)

In those three years, Swain’s raised around $3 billion in equity capital for 35 deals that, including debt, backed over $10 billion worth of purchases. Most of those transactions are “rollups,” and together they encompass several hundred companies. This year, Triago’s newly created branch is on track to gather another $1.5 billion from investors, backing some $5 billion in transactions. Triago gets fees of 2% on the equity it attracts for directs. (The remainder of the deal’s value is debt, and equity contributed by the sellers. Triago usually doesn’t get paid on those components.) Hence, the directs franchise should generate over half of Triago’s expected $55 million in revenue for 2023.

Triago faces competition from such investment banking rivals as William Blair, Harris Williams and Moelis & Co. But by Triago’s estimates, it’s much larger than any of these players in the space. Swain network of investors extends well beyond family offices to several Canadian money managers who were pioneers in direct investing, including Northleaf and Fiera Comox. According to Triago, the market size for deals funded by independent sponsors through direct purchases is running at around $20 billion in 2023. Hence, Triago’s $5 billion in transactions gives it a 25% market share, about equal to its sway in 2022. This writer’s conversations with insiders confirm that it’s by far the biggest force in this fast-expanding landscape. 

By Triago’s reckoning, today’s $20 billion annual run rate represents a 20-fold increase in five years. To be sure, directs are still a pretty small business compared to traditional PE, which raised $373 billion in the U.S. for 2022. And all but a tiny share of one-by-one direct transactions happen stateside. The momentum, however, heavily favors the challenger. “Limited partners large and small, the investors, are suffering from big-buyout-fund fatigue,” says Tim Clarke, a lead analyst at PitchBook. “They’re pushing back because the performance advantage, even over equities, collapsed recently. Money managers are giving up on megafunds and want niche deals. They’re much more willing to take a flyer on specialists, including independent sponsors.”

Swain views himself as an empire builder striving to upend the practices that long enriched Wall Street banks and bankers that he considers rigged for excessive profits. “I’m going to disintermediate big swaths of Wall Street,” he declares. He’s hoping for nothing less than turning no-middleman transactions that eliminate M&A fees into the industry norm. Swain’s ambitions extend to steering multiple billions that once flowed to mega-PE into directs, and even capturing loads of smaller deals the big guys crave. 

But in a sense, Swain is a Wall Street anti-hero who’s a throwback to the old Wall Street. He’s a wizard at relationship-building, constantly meeting and charming clients face to face in a kind of social whirlwind sans cesse. “He differentiated himself in a transactions business by not being transactional, but curating trusting relationships,” says Spencer Zwick, co-founder of Solamere Capital, a group that makes investments on behalf of the Mitt Romney, Bill Marriott and Scott McNealy families as well as around 100 other dynasties. Adds Sam Bremner, managing partner at Ivest Consumer Partners, a sponsor whose deals Swain’s matched to many investors, including Zell, “He’s the hustler who outflanked the competition with all his relationships. He’s simply found a much more efficient way of deploying capital by going direct.”

A Wall Street CEO at age 27

Born to a wealthy family, Swain grew up in tony Greenwich, Conn., and attended the prestigious Rye Country Day prep school. “I was the only kid who wore a sweater vest and carried a briefcase,” he recalls. “People thought I was goofy, but likeable.” At age 14, he began working every day after school at Permian, a hedge fund where his father served as CFO. “The firm used software to track the careers of CEOs, identify the great ones, and invest behind them,” he says. “I’d listen in to calls, and you could tell which CEOs not to back by the way they dodged questions.” 

As a student at Colgate University—he served as student body president and ranked first on the squash team—Swain won an internship at prominent Connecticut placement agent Eaton Partners, then joined full time on graduation. Even then, Swain had chosen the road where his natural gifts would lead to success. “I learned early that to be successful in finance, you either had to deliver superior returns or raise money.” He allows. “I was a ‘gentleman’s B’ student. For me, it wasn’t about using Excel models or algorithms to beat the market, but deploying charisma and connections to gather capital.” 

In 2016, investment bank and wealth manager Stifel purchased Eaton, and his new employer dispatched the youngster on what appeared a dead-end assignment. “Stifel was raising money for hedge funds, and they had this roster of potential clients that never responded to their calls and emails. They assigned me to cold call 1,000 investors on this ‘dead list.’ My boss kicked it to me as the lowest man on the totem pole.” On his 10th appeal to a family office in Atlanta, a money manager screamed, ‘Stop calling, you mental midget!’” To which Swain riposted, “I am rather short.”

From the ordeal, Swain captured an insight that would guide his career. “These family offices weren’t interested in PE funds. They were sick of the ‘2 and 20’ system, and paying asset gatherers that didn’t perform,” he remembers. “The reps would often tell me that they wanted to buy companies directly, they wanted to do deals themselves, but didn’t know how to find them.”

By chance, Swain then got a new task for which his boss also held out little hope: Find investors for a team of operators in contract to purchase a company—in this case, Dan Dee, one of the world’s largest manufacturers of “seasonal plush” or stuffed animals. Swain pounced. The transaction, he reckoned, was ideal for one of the firms that had expressed hunger for direct deals: Solamere. In 2018, Swain took the would-be Dan Dee team, from independent sponsor IVEST, to meet the Solamere contingent in Boston. They were greeted by one of Solamere’s big clients, Tagg Romney, Mitt’s son. Joining the meeting by conference call was Lee Scott, the former head of Walmart, whom Solamere also represented. The Ivest pitch so impressed the hosts that 72 hours later, Solamere agreed to provide $100 million in funding for Dan Dee. 

In fact, Swain notched a monster 2018 for Stifel, raising a total of $200 million. “I’m making $75,000 a year, and I just generated $4 million in fees,” says Swain. “I thought I’d get a quarter of the $4 million as incentive comp.” But Stifel offered only a modest raise and bonus. Swain curtly told his superior, “Sorry, but this doesn’t work for me,” and the next day began emailing resumes.

Shunning traditional finance for a meritocracy

He got interviews at a PE colossus, a big-name investment bank, and under-the-radar placement agent Triago, whose name sounded distressingly like that of travel firm Trivago. “Neither the PE fund nor the I-bank were interested in directs, and Triago wasn’t either,” Swain notes. But he saw at the French firm a free-wheeling panache rare on Wall Street. “In our interview, the partner told me, ‘If you do here what you did at Stifel, you’ll make ten times more. We’re all about paying for performance.’ That was the clincher,” he remembers. Swain took a job and found himself squeezed elbow-to-elbow into a tiny satellite office alongside six people, but “the place reeked of entrepreneurship.” 

In 2020, Swain brought his first direct transaction to Triago’s selection committee: A $156 million equity investment in a water filtration provider. He got a flat no. At the meeting, the Triago brass complained that direct deals took too much time, and provided no diversification, so if this one failed, it would damage Triago’s image. But the firm’s founder and chairman, Antoine Drean, agreed with Swain that the economics of directs were a lot better than for the firm’s platform that amassed capital for traditional PE. Fundraising fees for directs are comparable to those in PE, at 1.5% to 3%, Drean tells Fortune. “Only it takes one to two years to raise the PE money, [while] you can get the [direct] funds from family offices in six to eight weeks. Plus, you get paid on closing, whereas the PE firms send the fees spread over two years.” 

By focusing on directs, Drean concluded, Triago could attract much more capital than for traditional PE funds, and a surge in fees would follow. Drean overruled his top lieutenants’ decision, and unleashed Swain on a quest to make Triago king of directs.

Swain’s relentless wooing of clients both on the sponsor and family office side rapidly turned direct into by far the firm’s dominant franchise. In April 2022, Drean named Swain as Triago’s global CEO, placing him also in charge of the conventional PE fundraising, trading of limited partnership shares, and merger advisory arms. “The day the news broke,” Drean recalls. “I got a call from a Swiss billionaire who said, ‘Antoine, these stories keep saying your new leader is 27! That can’t be right. Those must be typos!” From a standing start, Swain’s directs business was the main force in driving Triago’s revenues from around $13 million in 2020 to an anticipated $55 million this year. 

Triago pays its 55 professionals a huge share of the fees on what they raise. Of the $55 million in revenues, overhead absorbs only $15 million, including salaries. The managers spilt $40 million among themselves and their aides, in deal bonuses as well as the profits shared among the whole team. Each of the folks who collaborated to forge a deal get their share of the fees virtually the day the checks arrive. “That pay system is why Triago has a younger, hungrier, more directed set of people, and it leads to low turnover,” says David Feierstein, founder of sponsor Ronin Equity Partners, “I loved that. The only reason Matt made it to CEO is because of results: He can raise more money than anyone else in the industry.”

The lure of pocketing a big cut on each dollar a partner raises helped Swain recruit his ex-bosses from his former employers. “I’ve hired my mentors and my mentors’ mentors,” he notes, citing that he poached both the exec to whom he’d reported to at Eaton, Michael Pilson, now 52, and the veteran investment banker who supervised Pilson at Bankers Trust in the 1990s, Neil Banta, 63. Swain has developed a stratagem for diverting attention from his own tender age. “One important client told me they didn’t trust anybody in a position of authority under 30,” says Swain. “Since then, when asked my age, I say ‘I’m roughly 30.’ I’ve been ‘roughly 30’ since I was 24.”

Relationship-building on the clock

For reasons of efficiency, Swain lives, works, and socializes all in a radius of five blocks in midtown Manhattan. He resides in the luxurious, Moorish-influenced Trump Park Avenue condo tower, where his landlord is none other than Eric Trump. In contrast to the supposed premium that the Trump brand commands, Swain quips that “In looking at the comps for top apartments, the bonus to living on one of his properties is that you get a discount.” 

Swain can look from his flat into the windows of Triago’s 25th floor offices, virtually across the street. “I want to see who’s working at all hours,” he explains. “If I see two or three people in the office on a Sunday morning, I suspect that a deal’s going sour, and they haven’t rang the alarm. So I make the 2-minute-and-50-second trip across Park Avenue to find out.” 

Every weekday, Swain hosts multiple back-to-back business meals—breakfasts at the Loewe’s Regency Hotel, lunches and dinners at the tony French eatery Bilboquet, both located within his sharply defined territory. “The first one is always 30 to 40 minutes, and the second slot is for a more significant client. That’s an hour,” says Swain. The tight scheduling can cause confusion. One time, when Swain invited two different clients to dinner at the same restaurant an hour apart, the first arrived late, and second early. “Client one was halfway through their entrée when I told him, ‘You have to vacate,’” recalls Swain. “I couldn’t leave client two standing at the bar. He was more important.”

Though Swain sports sober suits, you’d never mistake him for an investment banker laboring at an old-line investment bank alongside the cuff-linked MBAs. His ties hang crookedly, the narrow end showing below the wide one, and the knot dangling an inch or so below his collar. “He needs sartorial advice,” observes Pilson. So uneven is his coif that he could be self-barbering in the dark. Swain’s old school but disheveled look may be a reaction to his experience in his early days, when he feared appearing too buttoned-up and well-to-do to command respect. Pilson remembers a client meeting years ago where Swain blurted from nowhere, “I’m just a kid from South Philly!” Once they’d left, an astounded Pilson declared, “What’s this crazy stuff about South Philly?” Replied Swain, “Who’s going to invest millions on the advice of a preppy kid from Greenwich?” (Today, Swain regards the one-time Philly charade as a youthful folly.) 

One of Swain’s earliest, and subsequently largest backers is the Landon family of the U.K. Chris Sullivan, a former Credit Suisse investment banker who in 2015 founded Landon Capital Partners, the group that invests the clan’s money, was looking for the kind of adventurous, self-directed choices that reflect the family’s daring heritage, which includes a history of venturesome investments in the Middle East. “The businesspeople who built great wealth ran companies themselves, and know a lot about certain industries, so they and their families have great confidence in their own judgment in doing their own deals,” explains Sullivan.

That’s not an option in the traditional PE system. “When you put money with any private equity fund they take stakes in several companies,” Sullivan says. Once you commit, you don’t know when they’ll draw down your capital and put it to work. Nor do you know what companies they’ll pick. You’re not in control. You can’t even say yes or no or decide when the companies will be sold.” 

Matt Swain, Jesse Yao, and David Feierstein

Sullivan wanted to do discrete, one-by-one transactions where Landon makes the choices, and in some cases, controls the boards—and shun what he dubs “the blind pools.” “That’s the opportunity that Matt brought us,” he says. Their first deal came in 2021, when Swain and sponsor Ronin offered Landon the chance to purchase Heartisan Foods, a Wisconsin maker of such specialty cheese brands as Red Apple. Swain raised the $12.5 million from Landon that gave the family a majority stake. Later that year, Landon tapped Swain once again. The firm was planning two purchases: Walbro, a manufacturer of the small engines for the likes of chainsaws and weed whackers, sponsored by Nova Capital; and Paladone, a purveyor of promotional products licensed under famous brands, from Lord of the Rings puzzles to Harry Potter mugs, where IVEST provided the management team. “But the equity check for the two together was more than the family wanted to write,” recalls Sullivan. “So we asked Matt to bring in additional investors.” Landon sought to sell 20% of both Walbro and Paladone, and Triago found a single investor to secure the package.  

Incentives skewed heavily toward big gains

Like Zell, Sullivan especially appreciates that the incentives in directs, so highly tilted to the upside, are a great motivator for sponsors such as Ronin and IVEST, with whom they’ve worked extensively. The deal teams receive two types of compensation: fees and a “carry,” or share of the capital gain when the company, or parts of it, are sold. The sponsors receive 3% of EBIDA annually, but only if they increase the number starting from the date of the closing. If EBIDA falls in year one from $25 million to $22 million, say, they get nothing. After that, they’d only begin to receive the 3% if EBIDA bounces back to exceed the starting $25 million. As for carry, the managers must raise the enterprise’s value by 100% in five years before their participation kicks in. That means investors get a minimum annual return of 15% before the sponsors start collecting. 

The sponsors pocket 10% of the increase in value between 100% and 200%. So if a family office pays $100 million for a direct buy and sells for $200 million, the managers receive no carry. But at $300 million, they get $20 million, or 10% of the entire jump. Where things get great for the caretakers is when the gains go over 200%. Then, they garner 20% of the entire increase. Take a company from $100 million to $400 million in five years, and the sponsor-managers harvest one-fifth of the all-in, $300 million added, or $60 million. 

Compare that win-big-or-go-home formula with the much more staid, safe structure for traditional private equity. The big funds get that guaranteed 2% on all the money their investors commit, even if it’s not deployed yet. And as carry, they get 20% of the gains over an 8% IRR. That’s bogey is one half of the effective, 15% plateau where the capital gains sharing in direct deals begins.

Directs are the land of super-high expectations for both investors and sponsors. “The whole industry is gauged to annual returns of at least 25%,” says Bremner of IVEST. The industry, he adds, enjoys an edge because investors are buying candidates with problems such as antiquated computer systems and weak inventory controls that are readily fixable, but that discourage big PE funds. Plus, these middle-market choices are typically much smaller, and thus viewed as riskier, than the larger, established buys the major funds seek. As a result of their size and baggage, these diamonds in the rough don’t go to auction, while the big funds buy almost everything via competitive bidding. The upshot, Bremner adds, is that the directs are relative bargains. “Investors are typically paying five to seven times EBIDA, compared with 10 to 12 the marquee funds are paying.” 

Those attractive entry prices greatly lower the bar for superior returns, say the sponsors and investors. “At those prices, you don’t have to grow revenue in double digits to get a 25% IRR over five years," says Bremner. "You need to improve inventory turns, cash management, and other functions to lower costs and lift margins, and pay down debt. If you can also achieve mid-single digit revenue growth, the 25% target is easily achievable.” Of course, a big part of those gains must come from exiting a company bought at 5 times earnings for a multiple of 8 or 10. But the sponsors are selling not the old goods, but fully updated, “de-risked” properties carrying much lower borrowings. “So buyers are willing to pay substantial premiums to the multiples where we buy in," says Bremner. 

A key to directs: Embedding crack managers

The folks who repair the flaws at these underperformers, and feast if they succeed, are the sponsors. These are bands of managers who benefit from deep operating experience that they deploy as onsite swat teams, working beside management in c-suites, accounting offices and factories. “Unless the deal involves the sponsors’ embedding experts at the company, it’s not a direct,” says Swain. It’s these fixers who unearth the candidates, sign purchase contracts, and engage Swain to secure capital for the purchase. 

At Ivest, founder George Jones, a former CEO of Warner Bros. Consumer Products, and partner Chris Munyan, ex-CEO of gift manufacturer CSS Industries, among other associates, have taken top operating roles in EE, Dan Dee, and Paladone. 

Among Swain’s most frequent collaborators is consumer and industrial products specialist Ronin. Founder Feierstein left the private equity arm of Goldman Sachs in 2013 to join 3G. The assignment: Help direct the Brazilian group’s overhaul of its new acquisition, H.J. Heinz. Feierstein recruited three former lieutenants to join him for the campaign: Ike Helene from BlackRock and Jesse Yao from J.P. Morgan, as well as EY executive Yang Chen, with whom he’d worked he’d worked as an investment banker. They stayed on to spearhead the integration when Heinz purchased Kraft Foods. Then the Feierstein group, joined by Heinz executive Tiffany Bell, left 3G to freelance as a team, first in recharging digital banking purveyor NCR for Blackstone, then helping restructure cleaning chemicals outfit Diversey, a spinoff from Sealed Air, for Bain Capital.

In 2016, the Feierstein-led gang of five launched Ronin to concentrate on directs. So far, Ronin has purchased no fewer than 21 separate businesses that it’s combined into five rollups, among them Komline-Sanderson in water filtration, and Lotus, a manufacturer of brewing equipment for craft beers. Triago has raised all of the $300 million that funded those deals, from around two dozen different investors. “We wanted access to family offices that the big PE managers that go after pension and sovereign wealth funds could care less about,” says Feierstein.

The Ronin deal team now applies all their collective hands-on experience to melding the several middle-market players in each platform into running as a unified, well-tooled machine. Ronin installs managers in the central machinery of the acquired companies for six to eight months. Yao, Chen and Bell have all served as CFOs at portfolio holdingsFour Ronin members decamped in Burlington, a suburb of Toronto, to run DK2, a maker of power equipment for snowplows and trailers, taking the CFO, sales and IT, accounting, and planning and procurement positions. The “embed” ethic epitomizes how the direct world marches to a beat far grittier and down-home than the rhythms of Big PE. 

Seated at tony Bilboquet, waiting on the guest for the first of two scheduled dinners, Swain reflects on his conversations with Sam Zell. “Sam taught me what’s really important,” he says. “I’d say that someone ‘has a great network.’ Sam would shout back, ‘What the hell is a ‘network?’ That’s just air!’ A lot of typical Wall Street talk was ‘air’ to Sam.” 

Swain thinks of himself as a kindred soul to the bearded motorcycle enthusiast. “Sam was really blunt, he could be abrasive,” says Swain. “I’m really blunt, too. You’d think we’d be two people who rubbed each other the wrong way. But somehow, we were so blunt back and forth that we rubbed each other the right way.” The great tycoon and the Greenwich preppy found common ground in an underappreciated field that defies the Wall Street establishment—and disrupting the old guard in a crusade led by a “roughly thirty” boy wonder. 

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