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

Ladies, gents, and all curious humans, Tim Ferriss here. Today I’m sitting down with Graham Duncan—talent spotter, co‑founder of East Rock Capital, and a guy I’ve shared food poisoning and near paddle‑board decapitation with—so we’re going to talk clear thinking that travels beyond finance; to kick us off, how do you explain what you actually do?

I put people in the right seats so their strengths compound, which started with noticing a colleague was born to sell and moving him there, and now looks like acting as a general contractor for a few families: we meet hundreds of investment teams, back the best craftsmen, and sometimes help them spin out so their talent finally runs on full power.

What made you good at this early on, and what do you notice that others miss?

I think of it as taste in people more than judgment, and that taste evolved into hunting for a live tension—intensity paired with integrity—what I call commercial rather than transactional, the kind of person who plays hard but aims to create more value than they take.

How do you stress test integrity when everyone’s already polished?

I treat my interview as one small slice and make references the center of gravity, mapping how colleagues, bosses, and partners experienced someone over time; credibility for me is competence plus relationships plus integrity, and crisis windows like two thousand eight reveal who honored promises when it hurt.

What high‑signal questions do you rely on?

I ask, if you were hiring for this role, what would you optimize for, because it exposes their definition of success and the nuances I did not know to ask; in medicine it steered us to a hospital with a strong neonatal unit and nurses with steady hands, and in markets the trader analog is powerful if you control for their vantage point.

And when candidates hand you references, how do you get real signal and surface weaknesses without playing gotcha?

On‑list references work once the script runs out, so I press for specifics, use a net‑promoter‑style rating, make it safe and confidential, and stop when patterns repeat; I also ask who would be the ideal complementary partner, and I hold a core belief that in investing there are no products—only human mindsets and the decisions they’ll make next.

Josh told me to ask about wild gardening—what does that mean in your world?

Some people are orchids and need precise light and soil, others are dandelions and thrive almost anywhere, so I try not to force fit; I design for context so each person falls into a positive feedback loop with the work they can’t help but do.

How do you handle ambiguous cases where feedback conflicts?

I’ll hold both truths longer than feels comfortable and create more contact—ideally outside the pitch room—then work a live deal together to see their underwriting, which reveals the models they actually use under pressure.

For listeners, can you clarify your role and how you invest for families?

We serve a handful of families as an outsourced chief investment office with discretion across the whole pool, partnering with local specialists on real estate, backing hedge funds and private deals, joining special vehicles, and even helping managers launch when the fit is right.

What other patterns show up in the investors you back who later excel?

Originality plus triage—prolific idea generators who speak in their own language and can kill most of their darlings—and an intensity that makes you think, this analyst might take my job, which signals the obsession you see in any craft.

How do you sharpen your own thinking and uncover hidden assumptions?

Coaches trained in Kegan’s subject‑object work show me where my grip is too tight; I saw I lean futurist and overweight disruption risk, so now I hold that lens more lightly, and I use Byron Katie’s inversions to test beliefs by earnestly exploring their opposites.

Any practices for seeking disconfirming evidence and avoiding calcified views?

Keep a live paranoia you might be wrong, review mistakes, focus on sizing not just hit rate, and avoid public stances that trap identity; the best investors carry a meta‑identity of making money and can flip from long to short without ego when facts change.

Which books do you gift most often?

The Aspirational Investor for building portfolios around real human goals, Tribal Leadership and The Culture Code for shaping teams, and The Tools for training yourself to move toward discomfort—I even have my kids rub their hands and say bring it on, and we practice enjoying cold and rain instead of resisting it.

Let’s touch finite versus infinite games and how that maps to investors.

I prefer infinite players who love the game for its own sake and leave room for others, and I read that in time horizon and how they design their firm; I also like YC’s animal check and the duality others point to—passion with common sense, or assertiveness with open‑mindedness.

There’s a line you love: it’s not how well you play the game, it’s choosing the game—why is that so central for you?

It’s the zoom‑out that turns the game from something you’re subject to into a choice; with help from coaches and reminders like This Is Water, you can see your default scorecard, move your ladder if needed, and pick the mountain you actually want to climb.

Close us on your river metaphor for careers.

Think of a river between order and chaos: you apprentice on the order bank to refine reality, then edge toward chaos to assert new reality, threading the needle like great founders without losing the feedback loop—and you keep moving between the banks as your craft deepens.

In markets, staying top tier means reinventing the game as edges decay. Mike Burry’s housing short was a boundary push that nearly broke him but reset the field, and outside finance I care more about originality than rank—novelists like Rachel Cusk and Karl Ove Knausgård are stretching form without spinning out.

Pirsig is a cautionary tale about success and sanity, and I’ll link Robin Carhart-Harris’s entropic brain model for folks who are curious. Quick pivot—what did you mean by time billionaires?

We idolize money billionaires, but a twenty-year-old holds roughly two billion seconds, which is real wealth. Imagine what Rupert Murdoch would pay for five healthy years right now, while a younger me might’ve sold those same years far too cheap.

Tim Urban’s Life Calendar made this visceral, so I marked my weeks, plotted family milestones, and even pictured a photo-per-week poster to see a life at a glance. It nudged me to value the width of life—presence—alongside its length.

For newcomers to Wait But Why, start with The Life Calendar and The Tail End; Musk once opened Tesla’s doors to Tim for a deep series. How do you train that sense of presence?

The Tail End hit hard and I changed plans to see my parents far more, even bringing them to New York because most of our time together is front-loaded.

Matt Mullenweg shared that piece with me after his dad’s sudden passing, and it led me to lock in a family gathering every six months.

Day to day, I meditate with Ten Percent Happier and Sam Harris’s app, and I keep it light—the ‘Jubu’ crew made mindfulness approachable. I also try to savor the finite phases with my kids; the days can feel long while the years fly.

When I’m overwhelmed, I ask what I’d pay at eighty or ninety to replay this exact moment, whether it’s watching my dog or sitting in the yard.

Dan Harris has a three-minute gratitude practice that imagines you died last night, which snaps me into appreciating even a cranky family dinner. Byron Katie’s reminder helps too: the past and future are mental renderings; only this now is tangible.

Beyond the Kwame quote for your billboard, what else would you post?

I’d flip the frame: we’re spiritual beings doing a human tour, so greet whatever arrives—welcome to the party. My seven-year-old even yelled, “welcome, fear of the dark,” which showed he could feel it without being it.

I love that because it beats clunky phrasing like “I’m experiencing anger”; being an easygoing host to every emotion sticks. Any other lines you lean on?

A reworded Twain stays with me: life’s too brief for grudges and scorekeeping; use the sliver you have for love. Voices from the edge of life cut through the noise.

This has been a joy; I’ve got a stack of notes and listens queued up. People can find you at grahamduncan.blog, eastrockcap.com, and @GrahamDuncanNYC; anything else to share?

Yes, I co-produce a Lincoln Center event with CNBC where fifteen hedge fund and venture managers pitch live and all proceeds go to pediatric cancer research on May six; donate if you can, and if not, DM me for possible free seats. It’s a generous loop—ideas flow in, funding flows out to researchers.

I’ve attended and it’s a real mind stretcher. Show notes with every link are at tim.blog forward slash podcast; search Graham or Duncan, and until next time, stay with the present—it’s the only thing in your hands. Thanks, everyone. Bye.