The interviewer
Not long after Graham Duncan relocated to Montecito, California, in 2020, he went about opening a restaurant in trademark Graham Duncan fashion: with a lot of intentionality, a lot of interviewing, and no rushing.
He decided early on that the location had to be exceptional. He looked at a few good options, backed away when he realized he was forcing them to feel right, and waited, he says, until “a spot came up that has such good feng shui that your car kind of wants to go there”.
He got that spot, which will be called Little Mountain, after working for nearly a year to secure the long lease he wanted.
Rather than cut a licensing deal with a famous name who’d rarely visit, Duncan sought to bring in a chef who would become a fixture in the community. The problem: housing is extremely expensive in Montecito. The solution: buying and renovating a fixer-upper a few doors down from the restaurant. “I knew the biggest carrot I could provide was a great housing setup,” he explains.
Once he secured the chef’s residence, Duncan started doing what he does best—talent sniping. He interviewed 27 chefs before settling on the right hire: Joel Viehland, who had previously run the kitchen (and earned a James Beard Award nomination) at a Connecticut restaurant owned by BlackRock Co-founder, Keith Anderson. A talent search this thorough would have been exhausting for others but is standard practice for Duncan. “I figured it was a casting exercise, like most other things,” he says.
High-stakes casting exercises are Duncan’s specialty. He has mastered a distinctively talent -focused investing style since launching East Rock with Co-founder Adam Shapiro 18 years ago. Duncan officially stepped away in 2021, a year after moving to California, leaving Shapiro in charge of the firm. He now serves as Chairman Emeritus. He’s always been more curious about the founder than the idea, more interested in the fund man-ager than the fund itself. Duncan’s proven ability to assess people and their mutual compatibility has made him a trusted builder of teams, and years of accurate assessments and smart bets have brought him to the top of the leverage ladder: he’s the guy who picks the guy who picks the guy.
He is known for his rigorous approach to interviewing, especially when doing references for candidates and potential investment partners. He will conduct as many as 25 of these references for a single individual, mostly or all in person, and he brings an unusual combination of personal warmth and ice-cold analysis to the process. “Graham sits and listens and evaluates,” says Charlie Songhurst, an angel investor and former Chief Strategy Officer at Microsoft. “In most meetings, two people vie for control and find the slim overlap in their frequencies. Graham fully tunes into the other person. He puts his own ego away. He receives emotion, rather than pushing his emotions onto you. His empathy is off the charts.”
Screen violence upsets Duncan so much that he can’t watch it before bed. (“It drives my wife crazy,” he says.) When he lived in New York, he rode the subway with one of those wearable sound systems used by deaf people and gamers strapped to his back. He wanted to make listening to music and podcasts a full-body experience.
He’s the guy who picks the guy who picks the guy.
Sensitivity is one of Duncan’s defining traits. An-other is his appetite for assessing individuals, which is voracious. He loves surfing LinkedIn, where he analyzes everything from alma maters to profile pictures. “I feel like someone’s self-selected LinkedIn photo is so crazily high-signal,” he says. “Matching it up with my impression of what they’ve done in life and what life has done to them, finding patterns—I can literally do that for hours.” Most people, he admits, would find this “very boring”. But reading into people is at the center of Duncan’s personal investing style and the name of the game at East Rock. Spending long hours on LinkedIn is just one of the ways that he has done it.
Seeing the talent matrix
East Rock launched in 2006 in New York City with a single-family seed investment of $50 million and now manages $3.7 billion for eight high-net-worth families. The firm has annualized at 11.1% since launch, compared with 2.3% for the HFRI Fund of Funds Index, 6.2% for MSCI World, and 8.6% for the S&P 500. Its compound annual growth rate (CAGR) over the past decade is 12.5%, and it has outperformed the top 5% of its peer group over five-, ten-, and 15-year periods.
Behind these eye-popping numbers lies Duncan’s distinctive outlook. “Most investors are looking for companies or investments and evaluating them. Graham is walking around long/shorting people,” says Matt Huang, co-founder of Paradigm, a Bay Area VC firm focused on cryptocurrencies with more than $10 billion under management. This approach has turned Duncan into an object of fascination among peers who believe that even the impressive numbers don’t do him justice. “The economic value of calibrating and evaluating super-impressive elites as well as he does is insane,” Songhurst says. “If I wanted to poke fun at Graham, I’d tell him he should be worth $10 billion. If he’d been on the West Coast and in tech, he could have been the best seed investor of all time.”
Instead, he’s considered a best-in-class seeder of investment firms—eight in total—whose abilities as a talent whisperer border on the supernatural. Duncan and his team at East Rock were substantial day-one investors in funds such as D1 Capital and Paradigm, and they seeded Japanese hedge funds 3D Investment Partners and Mangrove Capital, among others; the funds they seeded have gone on to manage more than $5 billion.
When Huang left his role as a partner at Sequoia Capital in 2018 to launch Paradigm with Coinbase Co-founder Fred Ehrsam, one of the things Duncan did for him was interview COO candidates. The recommendation he came back with was surprising: a 28-year-old who didn’t work in tech or crypto. “Looking back on it now, years later, you can see the potential. But it was not obvious then,” Huang says. “She was one of the single best hires we ever made. Without Graham’s reference, we may not have hired her. It’s like he’s seeing ultraviolet waves or tuning into another frequency.”
Duncan’s mental world is busy with talent matrices. Many of the graphs and charts that he calls forth on his iPad are all about people, and map small galaxies of the top names in various investing sub-sectors. Friends compare him to Neo from The Matrix and the mutant telepath Professor X. Patrick O’Shaughnessy, Founder & CEO of the VC firm Positive Sum, has known Duncan for six years. “Of course what Graham does is analytical to some extent, but he is not into spreadsheets,” he says. “He sees the combination of unique ability and authenticity in a person better than anyone I know, and if it’s one degree off, he’ll wait to see perfect alignment. He doesn’t back 9/10s.”
If it’s one degree off, he’ll wait to see perfect alignment. He doesn’t back 9/10s.
–Patrick O’Shaughnessy, Founder of Positive Sum & Colossus
One piece of his method that can raise eyebrows is the Enneagram, a nine-faceted model of the human psyche that originates in ancient wisdom traditions. Duncan (who usually tests as an Enneagram 3, ‘The Achiever’) finds it more useful than most of his investing peers do, an occasional point of friendly contention. He cautions that it took him three years to warm up to the Enneagram, and that he sees it “more a tool for personal and spiritual growth than a personality framework per se”. Still, it obviously factors into his thinking. He’s written about the fact that he tends to back Fives, Sevens, and Eights, as well as his fellow Threes. The chef he recently hired for his restaurant is a Six and the GM is an Eight, two types that he believes work well toge-ther. “The Eights provide stability, the Sixes are loyal but also skeptical, in a great way, and alive in their decision-making,” Duncan says. He admits that some peers “think the Enneagram is astrological bullshit,” and rather than try to persuade them otherwise, he’s happy to lean more on other methods. “They’re all just partial lenses on reality,” he says.
If I wanted to poke fun at Graham, I’d tell him he should be worth $10 billion. If he’d been on the West Coast and in tech, he could have been the best seed investor of all time.
–Charlie Songhurst, Former Chief Strategy Officer at Microsoft
The outsider
Seated at the breakfast table of his two-bedroom apartment in downtown Manhattan, in the same renovated brick building that he used to live in with his family full-time, Duncan offers a simple explanation for how he became the type of investor that he is: “I’m kind of shy, but also very interested in people.”
He attributes this to the fact that he grew up feeling like an outsider. Born in East Palo Alto in 1974, Duncan spent most of his childhood in eastern Kentucky, where his parents ran a non-profit devoted to community economic development. It was, he says, like “growing up in a foreign country”. He was home-schooled until he was 10. Rather than bond with the locals, he studied them with the detached curiosity of an anthropologist. “I felt like I was outside the tribe trying to figure out what the hell was going on.”
Rowing came to the rescue. Duncan recalls two moments in his life when his future path sudd-enly emerged so clearly that it felt impossible not to turn onto it—what the author Daniel Coyle calls ‘moments of ignition’. Notably, both of these events starred people that Duncan didn’t know person-ally. The first occurred when he was 14 years old, just after his family had moved to New Hampshire. He remembers being gobsmacked by the sight of two high-school seniors, a man and a woman, who’d won national championships. “They were tall. He was handsome, she was beautiful, and they just had such presence,” he recalls.
He devoted himself to rowing. His specialty was an odd one: the 2,000-meter single scull. Neither a sprint or a marathon, it’s physically excruciating, even by rowing standards. It’s also the rare solo event in a sport in which the misery usually at least has company. Duncan, rowing alone, developed a tolerance for the pain and a ‘training mentality’. He won nine national championships.
He gave up rowing after his freshman year at Yale in order to focus on his studies. Duncan initially felt like a fish out of water there, too—a public-school kid intimidated by classmates who could read Plato in the original ancient Greek. But he found his groove doing research for a political scientist named Ian Shapiro (no relation to Adam), who helped him assess the credibility of various scholarly sources. “It was something about the clarity of the thinking, the pedigree—I started to understand his taste in other academics. He was a real mentor,” Duncan says.
I realized I was good at finding people who had access to a relevant information stream, and I developed a feel for how information leaks through a system.
–Graham Duncan
During his senior year—he graduated in 1996 with a degree in Ethics, Politics, and Economics— Duncan took a class about politics and financial markets with Richard Medley, who’d served as Chief Political Strategist for George Soros. Medley asked Duncan to help him start a research firm that was essentially an intelligence operation responsible for producing a $20,000 subscription newsletter. “Larry Summers called it a private-sector CIA,” he says. (Medley Global Advisors was sold to the parent company of the Financial Times in 2010; Medley died in 2011.)
Duncan created an international army of stringers and learned how to use them—which included assessing their credibility. Did they really know what they claimed to know? Did they have reasons to mislead or exaggerate? An ambiguous world of private information opened up, sometimes in ways that surprised him. During the Russian emerging-market crisis of the late nineties, he found a documentary filmmaker who had such high signal reads that he came to suspect she was sleeping with the finance minister. “I realized I was good at finding people who had access to a relevant information stream,” he says. “And I developed a feel for how information leaks through a system.”
Building East Rock
It was during a brief stint as an analyst at Protégé Partners in the early aughts that Duncan got his master class in referencing. His boss there, Ted Seides, had adopted the rigorous approach of David Swensen’s Yale Investment Office. “They were maniacal about it. They’d track down college roommates,” Duncan recalls. “Their professionalism around referencing was my window into the practice.” Referencing, in turn, provided a window into his future.
What Duncan considers his second ‘moment of ignition’ came from this same period, when he began hearing about Dan Stern, a prolific seeder and the Founder and Co-CEO of Reservoir Capital Group. “You could just tell from the people he had seeded that there was a consistency to his taste,” Duncan recalls. Stern had apprenticed under Richard Rainwater, whom Duncan considered the ‘gold standard’ of a certain type of highly effective investment manager that he describes like this: “They don’t have a specific identity—they just see themselves as money makers and are okay expressing a bet through other people.”
That Duncan didn’t know Stern personally didn’t matter. “Everyone talked about his style as so people-focused,” he recalls. “That was my orientation. I realized, ‘Oh, there’s a path to being an effective investor by selecting people and having high situational awareness on how to set up the right platform for them. I want to be that.’”
He launched East Rock Capital in 2006 with $50 million in seed funding from Stuart Miller of Lennar Corporation, the Florida-based home-building giant. (Miller’s family office is still an anchor client.) Duncan, who had begun to prove himself as a seeder of hedge funds by this point, sold Miller on a disarmingly simple pitch to identify the best investors in the world and make great investments with them. “I didn’t feel like I had a comparative advantage in picking stocks or doing any number of other styles of investment. Instead, we built around what I happen to be good at—picking people,” Duncan recalls. His first pick was Adam Shapiro, who’d been a year ahead of him at Yale and worked in the proprietary investment group at Goldman Sachs. Duncan got him to leave and become East Rock’s Co-founder and Co-CIO.
They began by investing in new hedge funds, using a strategy based on several theses. One was that managers are more significant than firms. Another was that smaller funds perform better than large ones. Duncan and Shapiro also believed that managers generate the best returns in their first five years, when they are motivated by the higher stakes of those first defining deals and able to devote more attention to the details of a fund that is still in its infancy.
Investing in these managers while they were in their ‘sweet spot’ became East Rock’s specialty. (And the numbers would later show that early involvement yielded better results. Many of East Rock’s poorer investments came when it had invested after, rather than along with, a fund’s financial sponsor.) The best of them came from top firms, and Duncan and Shapiro made it their business to know who they were.
East Rock became known for its carefully curated gatherings, where Duncan’s organizing presence remained low-key. He regularly put a couple of dozen up-and-coming hedge-fund managers around a table and had them pitch ideas. It wasn’t just about the ideas in these situations, but observing which way the table leaned. “If you have a group of 20 people together, the room kind of knows where the pockets of quality are most of the time. And you can see this if you read the room correctly,” Duncan says.
New York magazine mainly cited this role when it named Duncan on its 2023 list of the 49 ‘Most Powerful New Yorkers You’ve Never Heard Of’
He became a popular sounding board and got used to having anywhere between five and 20 ongoing conversations with managers who were thinking of leaving their firm to start a platform. In 2018, he assumed the chairmanship of the Sohn Conference Foundation, which holds a prestigious investing conference every year that benefits pediatric cancer research and reliably gets ideas and connections flowing. New York magazine mainly cited this role when it named Duncan on its 2023 list of the 49 ‘Most Powerful New Yorkers You’ve Never Heard Of’—despite the fact that he’d moved to California.
Information networks
East Rock invested in 15 to 20 hedge funds at any given time, most of which had assets under management (AUM) well below $1 billion. As its network and roster of clients grew, it developed strategies for investing in private deals like buyouts, real estate, and more esoteric special situations. (Nowadays about half of the firm’s invested assets are in hedge funds and the other half are in private investments.)
On the private equity side, East Rock sought to partner with two new fund managers annually. It set a goal of meeting with every partner who left a top private equity firm, and adopted certain methods for learning when they had: cultivating information-trading relationships with headhunters, for example, and scraping the web to discover when partner bios had been removed from websites. East Rock also made one-off co-investments with various PE firms; Duncan and Shapiro evaluated around 500 of these potential deals a year.
East Rock aimed to add one new family-office client every other year, with a minimum investment of $100 million, and positioned itself as a highly focused boutique alternative to single-family and multi-family offices. Passive investments and non-investment services were not its thing, and to this day it has never hired a dedicated client-services person.
Duncan’s experiments with transparency were another part of his distinct approach. East Rock held ‘pipeline meetings’ where it invited outside people in to discuss opportunities that the firm was considering. “I was consistently surprised by how often somebody knew something extremely relevant to one of the 30 deals that were up on the screen, something that I never would have been able to simulate in my head,” Duncan explains. He valued these revelations more than the potential cost of pulling the curtain back.
Duncan has described his work as a “game of strategy applied to people”.
In these and other ways, Duncan institutionalized his preoccupation with information networks and elite talent. His approach to referencing was codified in an internal document that contained a mock script for use in interviews and argued that there was much more to be gained from the process than met the eye—that every interview, for example, should be seen as an opportunity to gather new information, rather than just check facts, and treated as a way to ‘get a head start on how to manage and mentor’ someone down the road.
The assessment toolbox
Duncan mixes and matches a dizzying array of existing frameworks when assessing talent through interviews, references, and other inputs. His friend the author Josh Waitzkin, for one, is amused by the sheer volume of these frameworks.
“Graham has a hilariously wide library of mental models,” he says. Duncan also likes getting to know the people whose thinking has shaped his own, thereby creating an ongoing exchange of ideas. He became friends with Waitzkin after reading his book, The Art of Learning, and inviting the ex-junior chess champion (whose story was the basis for the 1993 film Searching for Bobby Fischer) to speak at a retreat of analysts that he had organized in Rhode Island. Three of the books that Duncan says have been most formative for him are by Robert Kegan, Ross Hudson, and Jim Dethmer and Diana Chapman; he’s built personal relationships with all four of these authors.
Duncan explained his preferred tools in one of his most revealing essays, ‘What’s going on here, with this human?’ They include the classic Myer-Briggs Type Indicator and the ‘Big Five’ or OCEAN (Open-minded, Conscientious, Extroverted, Agreeable, Neurotic) personality model, among others, including the Enneagram. His personal experience has much to do with the weight he gives to each. He writes, for example, that he conducted some 4,000 interviews before coming to view the Big Five, which had been recommended to him years earlier by a psychology professor, as “a revelation to help explain the patterns I had soaked up along the way.”
One of the main things he considers when evaluating founders and managers is whether their skills will translate outside of the organization in which they’ve already proven themselves.
“When he was in his really heavy days at East Rock, Graham would know every talented person at every investment firm that might leave to start their own thing, but he could also think deeply and incisively about whether they were ready for that,” O’Shaughnessy recalls. “He’d talk about how a person was amazing at Goldman, but did they have an independent identity? Were they self-aware enough? Were they unique enough? And if they were, had they fully embraced it yet?”
Another thing that Duncan is always trying to figure out is whether someone has truly stepped into their own, or if they’re still working within ‘somebody else’s frame’. In Silicon Valley, for example, there is constant peer pressure to become a founder. Is that why the person in front of him is doing it? “There’s a version of this where someone is frustrated with their current construct and their core motivation isn’t really to start a new thing— it’s just to have a new job,” he says. “A mid-career investor will start a firm because they’ve been offered money, or in reaction to socialized pressure, which is the equivalent of getting married just because everyone else your age is getting married.” Harvard psychologist Robert Kegan’s explanation of the stages of adult development has come in handy for him here. Duncan first immersed himself in this framework in 2011, at a workshop at the Harvard School of Education, and recommends it for assessing whether someone is ready to ‘trans-ition from a role player to an owner’.
If they are, Duncan will go to unusual lengths to reshape an environment to help them flourish. In his view, the rewards more than repay the effort.
“At any one time, there are only 100 people in the world whose map of reality on a complex subject—AI, global politics, interest-rate policy—is extremely accurate,” Duncan says. These individuals see the field clearly because of where they sit, but also because the field itself fascinates and absorbs them. This passion, Duncan explains, causes them to compete with the “joy of the tennis player who wins because he likes hitting the ball more than the other guy.”
Putting exceptional people into positive feedback loops is, for him, as satisfying as finding them in the first place. “Because he’s got this willingness to accommodate unique talent, he’ll create a custom container to hold a person who wouldn’t get hired at a normal investment firm,” Huang explains. Duncan, who has succeeded outside the usual boundaries, is especially attuned to the limitations of such constraints. “You need to understand why it makes sense for the candidate. People miss this all the time. They hire a person to do a specific job, treating them like a machine, but it’s much more complicated than that,” he says.
Just as Duncan rebuilt a house in Montecito in order to attract and keep the best chef possible, he made sure that the East Rock offices on East 55th Street included plenty of extra space for new partners to use while they found their footing. A real-estate investment firm that East Rock seeded in 2017 set up shop there for a full five years before out-growing it. East Rock’s eagerness to put a roof over the heads of friends and partners had obvious benefits. One was that, by providing space and covering other back-office expenses, it reduced overhead and by extension the pressure on anchor managers to rush into a non-strategic deal. Duncan also knew that putting his hand-picked talent in one space would generate conversations that led to co-investing opportunities. “Over time, you find things to do with one another,” he says.
At any one time, there are only 100 people in the world whose map of reality on a complex subject— AI, global politics, interest-rate policy—is extremely accurate.
–Graham Duncan
O’Shaughnessy remembers that when he first visited the East Rock offices in 2018, they seemed designed for luxuriating in. “You get out of the elevator and there’s this long, beautiful hallway. Form feels more important than function,” he says. Duncan has taken the same expansive, visitor-friendly approach to his hillside home in Montecito, which he refers to as a “rolling commune.” He likes to say, “You want to build the garden that the butterflies will fly into.”
The waiting game
When it comes to seeding, though, winged creatures cannot be rushed in. Graham’s unusual ability to wait out the moment is one of his defining characteristics as an investor.
“I’ve watched him be on the edge of seeding someone, where the normal impulse is to push them over the edge and give them a start,” Waitzkin says. “But Graham never pushes. He’s not susceptible to impatience the way most people are.” Duncan likes the author Diana Chapman’s analogy of a chick about to hatch. When you hear an emerging talent pecking from inside the egg, the temptation can be to help it break through. This is a mistake: the chick is still developing the strength required to survive outside the egg, and the surest sign that it is ready is when it destroys the shell on its own.
“If you break the shell for them, they will die,” Duncan says. “It’s very profound, this idea that if you mess with the origin in any subtle way it can affect the entire trajectory of the thing in ways you can’t foresee.” It informs the way things are done at East Rock, which has implemented elaborate systems to track who might leave the firm and when, but views inducing managers to leave as contrary to its whole talent-driven philosophy.
Graham never pushes. He’s not susceptible to impatience the way most people are.
–Josh Waitzkin, Chess master, martial arts world champion, and author
To intervene that aggressively would be to meddle with the formative energy that the Swiss-based theorist Peter Koenig calls source. Duncan considers this delicate concept highly useful. Even in entities with co-founders, there is usually only one true source, or possessor of the founding idea. “When it’s clean, it’s generative. That’s part of what makes something hum,” Duncan says. Too often, it’s messy. Duncan believes that disagreements over source explain many of the problems faced by new ventures. Source problems plague the management of multi-generational family fortunes, even if the person who made all the original money is six feet under. These misalignments don’t go away on their own, and their downstream effects can be catastrophic.
Duncan, who now views some of the professional frustrations of his twenties through the source lens, feels for those who are going through what he did. Only up to a point, though. Whatever empathy he extends is unlikely to cloud his investing judgment. “Graham wants good things for people, but he also cares about whether they’re going to make money. He holds both these things in his head better than anyone I’ve ever met,” Songhurst says.
When you get down to it, not everyone is as laser-focused on making money as they say they are. “There are people whose primary goal is to be right. That works a high percentage of the time, but it can be disastrous because your ego and portfolio get caught up in that goal instead of just making money,” Duncan says.
There’s a detachment to the ‘commercial’ mentality that he seeks in partners. It fits with Goldman Sachs legend Gus Levy’s concept of ‘long-term greedy’ and involves pacing yourself for success down the road. Duncan explains it this way: “There are people who are signaling that they’re in a repeat-iteration game. They’re not going to grab every penny on this transaction, because they know that there’s a sense of proportion about it somehow.”
One of the best embodiments of this perspective that he can think of is Dan Sundheim, who left Viking Global in 2017 to start his own hedge fund. Through mutual friends and interviews, Duncan felt that he knew enough about Sundheim that he ‘could calibrate to his taste,’ and as with Paradigm, his team-building abilities got him an important seat at the table. When Sundheim launched D1 Capital Partners in 2018, East Rock became a day-one investor and helped with some of the first hires. Meeting Sundheim in person only confirmed Duncan’s opinion of him as a master investor. “There was no defensiveness,” he recalls. “If you told him a new piece of information about a process or a person, he would drop his previous notion without hesitation. He had such a quiet ego.”
He considers Sundheim a prime example of another important concept, optimal grip, that Duncan’s rowing background has no doubt helped to drive home for him. In rowing, you’ve got to hold the oar with some firmness in order to get a solid pull; hold it too tightly, though, and you can blow the race (or even get thrown overboard) if the blade catches in the water on the recovery stroke. Elite rowers are less likely to ‘catch a crab’, as they say, but they’re also trained to release the oar quickly when it happens, enabling them to reset and get back in the game quickly.
“The ideal grip is tight enough to stay in control but loose enough to let go,” Duncan explains. He tells the story of Stuart Miller’s reaction to the 2008 global financial crisis, which hit within a year of seeding East Rock. “Suddenly, his Lennar stock is down to nine bucks from fifty-six, close to going bankrupt, and the rest of his money is with these two kids. We had anticipated some elements of the GFC and thought we’d be flat, or up, but we were down 12%.” Instead of panicking, Miller told him and Shapiro to stop feeling sorry for themselves and “play offense”. He cracked a joke about hauling sacks of gold down the street, helping them to see last-ditch maneuvers like that as ridiculous. “He was lightening the mood, bringing us back to reality,” Duncan recalls—in other words, grasping the situation flawlessly.
Graham wants good things for people, but he also cares about whether they’re going to make money. He holds both these things in his head better than anyone I’ve ever met.
–Charlie Songhurst, Former Chief Strategy Officer at Microsoft
The next chapter
Duncan’s ability to identify the right people at the right moment, and to foster the conditions in which they can thrive, produced results.
East Rock’s endowment fund has outperformed those of MIT, Brown, Yale, Duke, Stanford, and Harvard by at least one percent per annum (net of fees) over the last 10 and 15 years. Duncan’s signature investing style also allowed his firm to operate outside the usual constraints. Guided by the slogan ‘Talent Is the Best Asset Class’, it pursued different structures with different types of managers. Seeding, co-investing in a hotel, buying Bitcoin— if the talent was there, all were on the table. East Rock’s flexible approach to fees was designed to keep things flowing. “A lot of fund of funds people and endowment allocators have a scarcity mindset that is very focused on fees. They always feel like they’re being taken advantage of,” Duncan says.
“I knew there was an opportunity to approach things collaboratively, from the same side of the table.”
Unlike a lot of agents, Duncan has never really wanted to become a principal. “What’s great about being an agent is that there’s a way of framing it as servant leadership, which comes with built-in humility,” he writes. Giving up the day-to-day responsibility of running a commercial investment firm has left him more time to advise, mentor, parent, read, and join Friday Zoom sanghas. He’s also recently gone down the rabbit hole of helping others sort out full-time childcare. “I’m obsessed with helping friends hire nannies. It’s one of the most fraught, high-potential, high-leverage, variances out there,” he marvels. In other areas, though, he’s embracing the ordinary and reining in occasional overthinking. “I’ve been keeping a list of things that I’m not trying to optimize,” he says.
Duncan projects more equanimity than most people capable of such intensity. He eats and drinks in moderation, and has a generous and easy laugh. Friends attest to the fact that his move to California has made him even more relaxed. (He appears to agree: “On a hundred-point scale, my life satisfaction is 98 or 99,” he says.) Then again, there has always been something limber and creative about his investing style. O’Shaughnessy compares him to the late Richard Rainwater, another revered packager who was always figuring out new ways of putting the best talent together. Like Rainwater, he notes, Duncan has a distinctively personal approach that is unencumbered and in-the-flow: “Graham knows who’s got the juice, and has used this to give himself total freedom on the playing field.” Waitzkin calls him “The Wild Gardener.”
Duncan doesn’t appear to be chasing a mono-lithic project right now. “Rather than trying to assert reality, I’m trying to surrender a little bit and see what comes in,” he says. The grip has really loosened. With no firm to look after and more California sunshine in the mix, this period has become deliberative. Will it remain so? Is there a West Rock in Duncan’s future? “I have no desire to work for work’s sake. Less than zero—negative,” he says. Leaving East Rock was not about taking a break just to pick up again where he left off. It was, he says, an opportunity to reset and ask, “Is there another level to go up in playing this game, where you get a higher-balcony view and have impact with even less action?”
If anyone can successfully answer that question, it’s Duncan. The beauty of being a wild gardener is that growth happens without constant intervention. An elaborate talent ecosystem has grown up around him over the years, pushing in various directions from spots in the ground that he has chosen. With his combination of discernment and generosity, Duncan has put himself at the center of this flourishing system. The material rewards of this project have been obvious, but for him, the real reward is what he calls “this larger, ongoing human thing, all the positive feedback loops now in motion.” What they will create is a mystery— restaurants, companies, works of art, who knows— but that they will result in creation is a certainty.
Duncan likes when he can nudge potential into reality with a small gesture: a few words of advice, a well-timed introduction. He still remembers a moment from 20 years ago, when he met with a former Drexel partner of Michael Milken’s. “We were sitting at a restaurant in Santa Monica, and at one point he turned to me and put his hand on my arm and said, ‘Money’s like water, see? All you have to do is learn to turn on the faucet,’” Duncan recalls. “I thought I was in a David Mamet movie, but he’s right. Where does the water want to flow? You’re not forcing it. You’re working with what already wants to happen.”
