#872: Graham Duncan — Talent Is the Best Asset Class (Repost)

Graham Duncan’s approach to talent evaluation goes far beyond surface credentials and traditional assessments, emphasizing deep alignment between individual strengths and organizational needs, careful reference checking, and nuanced observation of motivations and character.

Graham's Method For Identifying Exceptional Individuals: Aligning Feedback Loops With Their Strengths and Motivations

Graham Duncan's discovery of his own talent began early in his career, notably when a sales hire directly challenged him to articulate his value. At that time, Duncan found himself managing much more experienced professionals and feeling imposter syndrome. Reflecting on a conversation with the sales hire, Robert, Duncan realized that his real strength was not judging people’s general capabilities, but identifying who would thrive in specific roles. For instance, although Robert applied as an analyst, Duncan noticed his energy lit up around sales and recruited him for that role, which became foundational to the business.

Duncan’s methodology orbits around constructing organizations where individuals are put into positive feedback loops that play to their compulsions and strengths. He seeks to design structures that let people gravitate towards their preferred activities and thus maximize their potential for world-class performance. Rather than constantly managing and motivating, Duncan prefers architecting teams and environments so that talent naturally seeks what suits them, whether they're "orchids" needing the right context or "dandelions" thriving in any environment.

This philosophy has guided his recruitment of top investment professionals to independently manage family wealth. As the external chief investment officer for wealthy families, Duncan and his team meet with over a thousand teams a year seeking the best investment "craftsmen." Often, these individuals, trapped in large organizations, flourish when given autonomy, unlocking creative and profitable energy.

Duncan describes his skill as "taste" in people rather than "judgment." Taste involves recognizing emergent patterns and knowing there isn't a single correct answer—similar to identifying distinctive notes in music—while judgment implies rigid correctness. He prefers seeing people as instruments who can play many "notes" depending on their context, and his focus is on matching them with the right environment so their best can emerge.

Evaluating Talent Involves Examining Beyond Credentials to Reveal Authentic Character

When evaluating potential, Duncan moves beyond resumes and credentials, focusing on qualities that signify commercial mindset, originality, and genuine domain mastery. One axis he values is the tension between aggression and integrity. In investment, for example, he cites David Tepper’s combination of bold, aggressive trading and unwavering ethical standards as the "platonic ideal" of a hedge fund manager. Such individuals create more value than they capture, a trait Duncan identifies as "commercial" rather than "transactional."

Exceptional idea generators stand out by not only generating a high volume of original ideas but also performing ruthless triage—knowing which ideas to kill and which to pursue. This "live trade-off" mentality is prevalent among elite portfolio managers. A qualitative sign of mastery is ownership of original language and thinking. While many emulate established figures like Warren Buffett, true masters eventually develop unique mental models and language, moving beyond industry jargon.

Another crucial distinction is "obsessive domain intensity." Duncan notes that those who’ve discovered their "game"—like Wayne Gretzky with hockey or Warren Buffett with investment—display an intensity and compulsion that drives long-term mastery. These individuals aren’t motivated primarily by wealth or external status, but by the pursuit and enjoyment of their craft.

Reference Checks: Evaluating With High-Signal Questions and Non-verbal Cues

Reference checks are central to Duncan’s evaluation process. He finds even "on-list" references provided by the candidate surprisingly high-signal, as after about ten minutes, scripted answers give way to genuine assessments. Accumulating responses across several references reveals patterns and, when there is ambiguity or contradictions in feedback, Duncan recommends creating more context—spending time with candidates in diverse settings and observing their behavior in live decision scenarios.

A particularly powerful question to ask references is, “If you were hiring someone for this role, what criteria would you use?” This uncovers how they define success and exposes essential nuances and priorities that standard questioning might miss. Making the interaction safe and collaborative elicits honest feedback, as references recognize the interviewer’s aim to match talent w ...

Graham Duncan and Tim Ferriss explore the profound impact of coaches, mentors, structured self-inquiry, and time awareness on personal development, emphasizing the importance of recognizing and loosening unconscious assumptions to broaden perspective and enhance present-moment appreciation.

Coaches and Mentors Help Uncover Unconscious Assumptions Blocking New Perspectives

Graham Duncan describes how investing heavily in trainers and coaches, particularly Caroline Coughlin, enables him to surface hidden assumptions—beliefs so ingrained they hold him, rather than the other way around. Through their work, Coughlin teaches Duncan to ask progressively better questions, ultimately helping him to see what he is gripping tightly and to recognize which beliefs are entangled with his identity or ego. He explains that if you can’t articulate the opposite of a belief, it might indicate your identity is intertwined with it.

For instance, Duncan recounts how his business partner identified a "futurist paranoia" bias in him, specifically a heightened concern for disruption risk in investments, such as climate change threats to hotels or technological shifts affecting value investors. The observation made Duncan more aware of his assumptions and able to consider them more objectively.

Duncan references Bob Keegan’s theory of adult development, which asserts that psychological growth means making unconscious determinants of behavior conscious. The process involves recognizing the beliefs we have inherited or taken for granted (like religious beliefs from family or community) and transforming them into conscious choices. This mirrors the process that coaches and mentors facilitate: increasing one’s mental complexity and moving more of our assumptions from subject (unseen drivers) to object (conscious choices).

Coaches Enhance Practitioners' Thinking By Teaching Better Questioning and Articulating Opposing Views

Tim Ferriss introduces Byron Katie’s practice, "The Work," which involves scrutinizing beliefs that cause discomfort or anxiety by clearly stating them and then its precise opposite. For example, transforming "my dad should be more attentive to my mom" into alternatives like "my dad should be less attentive to my mom" or "my mom should be more attentive to my dad." Practitioners then search for evidence, however minor, that supports these opposites, which helps disentangle emotional attachment from initial assumptions.

Graham Duncan, a participant in multiple Byron Katie workshops, finds her practice impactful. He summarizes her process with questions such as: What’s the belief? Is it true? What’s the opposite? Can you absolutely know it’s true? How do you feel when you think that thing? This rigorous questioning helps practitioners loosen their grip on tightly held assumptions and highlights that their initial perspective is just one of many possibilities.

Ferriss and Duncan stress the value of training oneself to look for disconfirming evidence, a cornerstone of scientific inquiry. This can be developed through conscious practice—deliberately articulating alternatives and seeking data for them. Ferriss likens this to optical illusions, where once another way of seeing is pointed out, both interpretations become available to the mind, forever altering perception. Similarly, recognizing one’s biases and practicing seeing the opposite perspective encourages flexibility and objectivity.

Duncan says he invests heavily in trainers and coaches because the long-term payoff in loosening unconscious mental constraints and broadening his perspective far outweighs the upfront cost.

Meditation, Reflection, and Time's Value Aid Awareness of Unconscious Patterns and Per ...

Kwame Appiah Quote: "Not how Well You Play, but Which Game You Choose" Highlights Circumstances Vs. Ownership

Graham Duncan introduces the Kwame Appiah quote: "It's not how well you play the game, it's deciding what game you want to play," explaining that recognizing the game you are playing allows you to move from being unconsciously influenced by external circumstances to consciously directing your life. He describes this shift as turning the game from subject to object, which means becoming the author of your life by choosing your own priorities, rather than passively adopting those handed down by society.

From Influence to Autonomy: Becoming the Author of one’s Life

Duncan illustrates this with the story from Greg McKeown about feeling pressured to attend a work event instead of being present at the birth of his child, describing it as a transition from being socialized to being self-authoring—determining his own scorecard of what matters. This is essentialism: ensuring your priorities are self-chosen rather than socially imposed and using personal stories as reminders not to repeat past misalignments.

Most Unconsciously Play the Game Of Accumulating Money, Status, or Power; Conscious Awareness Allows Desire Verification

Duncan claims most people default to the game of accumulating money, fame, or power without having consciously chosen these as worthwhile pursuits. He suggests the value of making your "game" explicit and verifying that it genuinely aligns with your desires, rather than simply following societal defaults.

Life Stages and Re-evaluating Goals

He emphasizes that at different stages of life, the games people play may change. It is important to periodically ask oneself, "What game am I playing right now? And can I see it?" Coaches can help people recognize and re-evaluate which game they're optimizing for at each stage, ensuring the metaphorical ladder is leaning against the right wall. Both Ferriss and Duncan discuss the process of "zooming out" to gain a "God’s eye view" on your life to see if you’re still climbing the right mountain or need to change direction—echoing the process of adult development and greater self-awareness over time.

"God's Eye View" Parallels Wallace's Observation—Everyone Swims In Unconscious Context, and the Worthwhile Project Is Learning to See It

This "God’s eye view" parallels David Foster Wallace’s "This Is Water" metaphor: most people swim in unconscious contexts until they actively try to notice them. As Duncan says, at every life stage there are realities so pervasive to us we don’t even see them—the lifelong project is to notice and consciously relate to these waters.

James Carse's Finite vs. Infinite Games: Why Some Careers and Partnerships Are More Generative and Sustainable

Duncan introduces James Carse’s concept of finite and infinite games. Finite games, like baseball or card games, are played to end—there are winners, losers, and clear boundaries. Infinite games, on the other hand, are played to keep playing; the goal is to continue the play, recruit others in, and expand the possibilities.

Finite Players Aim to Win; Infinite Players Aim to Continue and Recruit

Duncan explains that observing his own children, Carse noticed their intent in different games: some were about winning and ending, others about ongoing play and inclusion. This applies equally to careers and markets. Finite players seek victory, while infinite players seek longevity, creativity, and participation.

Infinite-Game Players in Markets Are More Valuable for Their Long-Term View, Continuous Innovation, and Viewing the Market As an Endless Game

In the world of finance, Duncan values participants who view markets as infinite games, requiring constant innovation and adaptability. Successful players see themselves as perpetual participants, focused on long-term generativity rather than short-term wins. Strategies or games that worked five years ago become obsolete; the infinite player is always seeking new frontiers, playing with the boundaries rather than being constrained by them.

Infinite Game Players: Lightness and Humor About Setbacks due to Practice Over Outcome

Duncan describes how an infinite-game mentality brings lightness in the face of loss. He recounts a portfolio manager who, after a major short gone wrong, laughed off the loss and quickly moved on to the next opportunity. This attitude stems from practicing participation and innovation rather than focusing solely on outcomes.

Infinite-Game Players Create More Value Than They Capture, Allowing Others to Benefit

Infinite-game players are also more likely to create value that others can build upon, focusing on enlarging the playing field and enabling others, rather than zero-sum accumulation.

Practicing Present-Moment Awareness: Prioritizing Life's Width Over Length

Duncan turns to the importance of being present, highlighting the adage from Gretchen Rubin that "the days are long, but the years are short ...

The discussion between Graham Duncan and Tim Ferriss explores a range of psychological models and mental tools used by leading thinkers and performers to navigate decision-making, structure organizations, and build resilience.

Dan Siegel's River Metaphor: Chaos, Order, and Mental Health in Career and Innovation

Graham Duncan introduces Dan Siegel’s river metaphor to explain psychological balance: one bank of the river represents chaos (e.g., schizophrenia), while the opposite bank embodies rigidity (e.g., OCD). Mental health, according to Siegel, is found in navigating between these extremes—"swimming in the middle of the river." Duncan relates this metaphor to careers and innovation. Early in a career, professionals apprentice alongside the rigidity bank, absorbing established frameworks and learning how reality is defined in their chosen field. This period is often about refining reality and gaining fluency in the existing paradigm.

However, genuine innovation happens closer to the chaos bank, where individuals assert their own reality and craft novel ideas. Duncan cites visionaries like Elon Musk and Steve Jobs, as well as poets and original novelists such as Robert Persig, Rachel Cusk, and Karl Ove Knausgaard, who dwell near this edge, creating paradigms the rest of society eventually adopts. Still, there is significant risk—without feedback from reality, one can become unmoored and appear “crazy” rather than innovative. Starting an independent venture, Duncan emphasizes, is fundamentally about asserting reality; doing so too early or without grounding can be dangerously disorienting, as in the experiences of Mike Burry, who was seen as wrestling with sanity while shorting the housing market during the financial crisis. The optimal path, therefore, is to oscillate between rigidity and chaos—to "swim back and forth," balancing creative experimentation with periodic returns to structure.

Picasso’s advice—"learn the rules as an amateur so you can break the rules as a professional"—captures this principle. Mastering established frameworks enables innovators to challenge them with credibility and impact.

James Carse, Jim Simons, and Others in Graham's Reading as Templates For Rethinking Problems and Structuring Organizations For Excellence

Duncan references several thinkers and frameworks that serve as templates for creative excellence and organizational design. He points to Jim Simons, the founder of Renaissance Technologies and a figure renowned for quantitative investing. One trait Simons prizes is "good taste in interesting problems." This ability to discern promising questions and challenges has been foundational in generating extraordinary returns.

Ashwin Chhabra, who manages Simons’ family office, critiques modern portfolio theory in his book "The Aspirational Investor." Chhabra argues that classical theory doesn’t reflect how people behave or what they care about. Instead, he proposes a portfolio construction approach rooted in actual practice, focusing on real-world goals and risks rather than abstract theory.

Duncan also recommends "Tribal Leadership" by Dave Logan, a book that offers a taxonomy for identifying stages in organizational development—a framework Phil Jackson, legendary NBA coach, considers the best for understanding world-class teams. For cultivating extraordinary group culture, Daniel Coyle’s "Culture Code" is influential, studying elite organizations like Pixar and the Navy SEALs to uncover the repeatable patterns and nuances of effective cultures. Duncan notes that these books aid leaders seeking to structure their teams for enduring excellence.

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