The Distillery · Volume XVI
- 30-min read
The Distillation of Chris Begg
The Essence of Everything That Grows
The first thing you notice about Chris Begg is his eyes. There’s a light in them that you can’t manufacture. It comes from someone who is genuinely in love with learning, in love with life, in love with the process of getting a little bit better every single day.
Chris is the founder of East Coast Asset Management and an Adjunct Associate Professor at Columbia Business School. He also surfs. He studies hieroglyphs. He paints. He does three-month immersive deep dives into subjects ranging from evolution to graph theory. He just built an AI analyst named Faraday. He writes music.
And every single one of these things connects.
There’s no separation between the investor and the philosopher and the artist and the father. It’s all one person, operating from one source, with a kind of joyful curiosity that makes everyone around him want to go deeper into their own craft.
A man completely at home in his own life.
Contents
- The PIPER Mindset
- Origin Story
- Lila — Eternal Play
- Arete — Quality & Virtue
- The Hare over the Wave
- Freedom & Spaciousness
- The Scaffolding of Learning
- Three-Month Deep Dives
- Right Brain / Left Brain
- Shibumi
- Compression & Compressence
- Graph Theory
- Entropy Reduction
- Value 1.0, 2.0, 3.0
- Asymmetry
- Navigating Clouds
- The V3 Principle
- Building an AI Analyst
- Stewardship & Teaching
- The Pilgrim’s Path
- Designing a Life
Key Themes
01
The PIPER Mindset
One of Chris’s earliest frameworks came from his mentor Peter Kaufman, the CEO of Glenair and one of Charlie Munger’s closest intellectual companions for over thirty years. What Chris learned from Peter is seeing how the world works, seeing how these different areas such physics, biology, and human history all connect.
Chris distilled it into an acronym: PIPER Persistent Incremental Progress Eternally Repeated.
“This is really at the heart of the magic of compound interest, which we work with in the investing world, but it’s also the underlying principle with which all evolution takes place.”
PIPER is how Chris sees businesses that endure. It is how the Danaher Business System operates, how Mitch Rales built an empire of operational excellence from Toyota’s Kaizen methods. No special sauce. Just the dogged, joyful pursuit of getting incrementally better and then repeating that forever.
It comes down to small, deliberate improvements over enormous stretches of time.
The question that matters, How do I keep getting better at a pace I can sustain forever?
02
Origin Story — Choosing Heroes
Chris sees two ways to evolve a craft. The first is to learn from a great mentor, which he thinks is actually the best way if someone is willing. The second is to choose heroes and take bits and pieces from them to craft who you want to become. That’s what Chris did, he studied lots and lots of great heroes.
In his early days, Chris didn’t have a great mentor, but he had a great seat which was an investment analyst role right out of his undergrad that gave him room to sit, learn, read, and develop a temperament for the kind of investor and person he wanted to become. He studied the greats and absorbed what was useful.
This didn’t stop when Chris was young. He continues to surround himself with interesting people across multiple disciplines. Chris says that he’s, attracted to curiosity, I love surrounding myself with people who are curious, that are learning and they’re sharing their learning.
His father was an accountant on Cape Cod who worked in a small office. What Chris loved about what his father did was that he really cared about his clients. He served them well, and they respected him. Chris thought: I want to be in a position to serve others. When he told his dad he wanted to be an accountant, his father said, “No, you’re not. I really don’t like accounting, but I like working with my clients.” That instinct toward service has guided so much of what Chris does. Find something you love doing and serve your clients well while doing it.
The leaders of enduring businesses are not just effective operators and intelligent capital allocators, but they think of themselves as stewards of the enduring enterprise. They want to leave the business in better shape for the leadership that follows… Stewards of enduring businesses operate the businesses to last through time. They do this by persistent incremental progress repeated without end, continual improvement of processes and systems and by persistent innovation through research and development, sowing seeds for the future. These investments may be at the expense of short-term profits for a longer-term reward. If they starve the future of these nutrients the organizations will not endure. Wall Street celebrates when companies eke out small incremental profits at the expense of investments in marketing and research and development. Thus many business leaders are easily persuaded and motivated to ignore this critical counterparty.
03
Lila — Eternal Play
If there is one word I could use to describe Chris it would be Lila, the Sanskrit concept of eternal play. It’s the concept that whatever you’re doing, whether it’s your craft, your hobbies, or your family it should feel like play. He embodies this deeply in everything he does. He seems to have a buoyancy and childlike spirit about him. He said to me,
“When it feels like play, it’s joyful. It’s not happiness. It’s something different. It’s an expression of an eternal dance. Even when things are challenging, having a playful attitude has been a guiding principle.”
For Chris, Lila is not about being carefree, but it involves approaching even the most consequential work with a playful attitude. He calls investing in a concentrated portfolio during a market dislocation “high-consequence play.” I believe play is what has allowed him to maintain his quality for decades. When you’re with Chris, you can feel this love of play in everything he does. It shows up in the art studio with his son, on the water surfing at sunrise, in the three-month deep dives into whale biology and Egyptian hieroglyphs. As his favorite philosopher Heraclitus wrote, Eternity is a child at play with colored balls.
If you are doing something you would do for nothing, then you are on your way to salvation. And if you could drop it in a minute and forget the outcome, you are even further along. And if, while you are doing it, you are transported into another existence, there is no need for you to worry about the future. ~ Dr. George Sheehan
04
Arete — Quality & Virtue
In Ephesus, Turkey, there is a beautiful piece of architecture where four Greek goddesses are represented. The first is Knowledge, Episteme. The second is Wisdom, Sophia. The third is Intelligence, Ennoia. And the fourth is Virtue, Arete. Chris sees this as a continuum: moving from knowledge to wisdom, from reason to intelligence (doing something simpler, with less entropy), and finally to Arete by doing it with quality and virtue.
We think this progression is spot on and we are attempting to walk a similar path. How do we transform knowledge to wisdom through experience and deliberate practice? How do we transform wisdom into intelligence by making the complex simple? Finally, how do we arrive at excellence and mastery by honoring win-win constructs, aligning with infinite game players, and benefiting from the positive feedback loops of doing well by doing good?
Robert Pirsig’s Zen and the Art of Motorcycle Maintenance made a big difference in Chris’s life. It was the first time he saw articulated what he felt inside about quality. “He really struggled to put those words on paper. That’s why he had to write Lila, to go deeper into the philosophy of the metaphysics of quality.” Chris would fast-forward through the narrative to the philosophical passages, mining for those nuggets of what quality actually is.
The person who embodies this most fully in Chris’s experience is Nick Sleep, who ran the Nomad Investment Partnership out of London. Some of the best investment letter writing Chris has ever seen. Nick articulated quality in his letters and lived it right up to the point where he closed the fund. He wanted to close it without any deterioration of quality. “It’s impressive because it’s not just words, it’s actions.”
Chris and Nick have a conversation every year where they go deeper and share the story with the students. For anyone who hasn’t read the Nomad letters, they’re all public now on a foundation website. Wonderful investment lessons including how they broke down Amazon in real time by looking at the pattern recognition of Costco.
“The leading edge is operating everything you do with quality. Everything you do with virtue. It’s how you treat your counterparties. It’s the investments you want to associate with. It’s how you journal in the morning. Every detail is doing it with a sense of quality. It becomes the way you want to live your life, in every interaction.”
05
The Hare Over the Wave
While studying the Egyptian hieroglyphs, Chris discovered one that resonated deeply with him: a hare, elevated above the ripple of a wave. To his surfer’s eye, it looked like it was riding the water.
Then he looked it up. The hieroglyph was a symbol for the goddess Wenet, and it meant the essence of life. Wenet was the goddess who allowed the Nile to flood every year, irrigating the crops, giving life. The symbol also meant rebirth. The hare over the wave means the essence of life, a symbol of swiftness of movement and mind, and perhaps most importantly, renewal.
The hare above the wave became Chris’s personal symbol. It is everywhere in his life. It sits at the intersection of things he values: living from your essence, the ocean, cyclical renewal, the commitment to shedding what no longer serves you.
Symbols, for Chris, carry meaning that language cannot. They bridge the left and right brain. They hold multiple definitions at once. Egyptian hieroglyphs fascinate him precisely because they communicate on two planes simultaneously, both phonetic and symbolic. For Chris having art and symbols around him is not just decoration, but a way of staying connected to something deeper than words.
06
Freedom & Spaciousness
“The essence of mathematics lies in its freedom.” — George Cantor. Chris expanded this: “The essence of everything that grows lies in its freedom.”
Chris made an architectural life design decision early on. Freedom of thought, freedom of time, freedom of creative expression. Everything he’s built flows from that choice. Launching East Coast Asset Management was about painting his own canvas. Living immersively across two geographies was about designing the life around the work, not the other way around.
Over time he realized he needed an internal scorecard, not just an external one. More freedom of time. More freedom to make decisions he thought were intelligent versus decisions that would be acceptable to a group of limited partners. The internal scorecard became more meaningful than anything the outside world could measure.
And what that scorecard actually measures, more than anything, is spaciousness. The room to let a conversation extend past its scheduled end. The ability to stay on the water an extra hour when the waves are good. The space to follow your own curiosity. A dear friend of Chris’s calls it linger longer, the practice of letting moments breathe instead of rushing to the next thing. But it requires design. You have to structure your life so the spaciousness can exist.
“Time is by far the most valuable resource we have. And who you give your time to—you’re giving that resource away. I look at my calendar on a weekly basis. It’s a good indication of whether I said yes to things that really get me excited or said yes to things where I wake up and I’m like, I don’t really want to do that.”
Chris gives his most valuable two hours each day from 4:30 to 6:30 AM, before the family is awake to the work that requires his highest cognitive abilities. It starts with a blank journal. Sometimes the unconscious flows onto the page with symbols, sketches, or free-form. Then it moves toward structure: a model on the computer, a narrative writeup, or just creative play. Unstructured to structured. That’s the daily rhythm.
07
The Scaffolding of Learning
Chris admits it took him a long time to learn how to learn. Like most of us, nobody taught him. For years he was reading what was assigned, absorbing little, with no scaffolding for knowledge to stick. Then he began building a system that was organized across three dimensions: the breadth of multidisciplinary curiosity, the depth of immersive fluency, and what he calls height, the ability to see where knowledge lives on a timeline, from the origin of the universe 13.7 billion years ago to the leading edge of the present.
Chris calls this 3-dimensional learning: depth of knowledge, breadth of knowledge, and height to see the timeline across time and how the threads connect.
You don’t just want a breadth of knowledge. You need depth. You don’t want to know just a little bit about a lot of things, which is where people sometimes get stuck by being multidisciplinary. You need to create a habit to go deep. The depth of the work allows you to really have a nuanced fluency with the subject, not just a surface-level understanding.
08
Three-Month Deep Dives
About 20 years ago, Chris developed a habit where he would take three-month increments to go as deep as possible. It is total immersive learning in a subject for three months. Then he steps back, digests it, maybe writes it up in essay form, and moves on to the next subject.
“When you bring yourself back by doing the immersive work, you get into the mindset of what it felt like to have an epiphany that perhaps no one has articulated before. If you’re studying an artist, what did the artist feel like when he or she was creating this? What did it feel like to be in that time period? I think that immersiveness creates a texture to the learning. It’s not just something from afar; it’s something that you’ve embodied. That’s why when I do a deep dive, like on evolution, I’ll try to touch every aspect from all angles—from an aspect of poetry to an aspect of art, which sometimes involves making my own art from it.”
Chris is searching for timeless principles. Nuggets of truth that, once found, apply fractally across disciplines. Every thread connects to every other thread, and the deeper you go into any one, the more you see the whole.
When Chris does a deep dive he wants to go so deep until a concept becomes more than an idea. The knowledge is not just known, it’s part of you, it’s an embodied experience.
09
Right Brain / Left Brain & The Whole Mind
Ian McGilchrist’s work has been one of the most important bodies of work Chris has discovered. He’s spent several years with Ian and brings him into the Columbia classroom annually. The core insight: the human species has been languaging the world so much that we’ve become left-brain tilted. We’ve atrophied our right-brain creativity.
The left brain is where language happens, it’s the focused, analytical part, but it misses the bigger picture. The right brain gives context to the world, context to your relationship with things and people and ideas. It sees the whole, not just the parts. A right-brain stroke is actually more problematic than a left-brain stroke because you lose your context for the world entirely.
In the craft of investing, analysts tend to be left of center with analytical rigor. A portfolio manager needs right-brain ability to see risk, see the whole, think about position sizing, how everything fits the overall picture. First principles thinking, critical thinking, holistic thinking, these capture both sides working together. Chris who leans more right brain, but has developed habits and practices to evolve his left brain.
He also thinks about symbols differently because of McGilchrist’s work. Symbols carry something that’s not linguistic, they bridge into right-brain context and creativity. Symbols to Chris express something deeper than words.
When Chris thinks about someone like Leonardo da Vinci, he sees this incredibly whole-minded personality. Someone so creative but with incredible focus. The detail of his journals, the breadth of his understanding. That’s the integration of both hemispheres at the highest level.
10
Shibumi — Simplicity on the Other Side of Complexity
When Chris graduated college, his father gave him a book called Shibumi by Trevanian. On the surface it’s a fictional spy novel. But buried in it is a passage defining shibumi which is a state of elegant simplicity, of refinement so deep it becomes effortless.
“It really articulated the kind of place I wanted to end up. Shibumi—a state of elegant simplicity or refinement. What I would call now the simplicity on the other side of complexity. That passage was almost like a beacon for me of where I wanted to be, both in the way I thought and the way I wanted to architect a life.”
Where most people get it wrong is stopping at the simplicity on this side of complexity. The real prize is on the other side. All the great investment ideas Chris has ever had required navigating through complexity first. You can’t start at simplicity. You have to navigate through the questions by doing the deep work, by understanding the natural inclination to avoid areas where there’s uncertainty, fear, clouds. But can you work through the questions and get to the other side where you have understanding?
It’s the same with surfing, painting, making music. You have to put the hard work in. Then you can refine until it looks like flow, like effortless movement. But you can’t start there.
On page 77 of Shibumi:
“Shibumi, sir?” Nicholai knew the word, but only as it applied to gardens or architecture, where it connoted an understated beauty. “How are you using the term, sir?”
“Oh, vaguely. And incorrectly, I suspect. A blundering attempt to describe an ineffable quality. As you know, shibumi has to do with great refinement underlying commonplace appearances. It is a statement so correct that it does not have to be bold, so poignant it does not have to be pretty, so true it does not have to be real. Shibumi is understanding, rather than knowledge. Eloquent silence. In demeanor, it is modesty without pudency. In art, where the spirit of shibumi takes the form of sabi, it is elegant simplicity, articulate brevity. In philosophy, where shibumi emerges as wabi, it is spiritual tranquility that is not passive; it is being without the angst of becoming. And in the personality of a man, it is … how does one say it? Authority without domination? Something like that.”
Nicholai’s imagination was galvanized by the concept of shibumi. No other ideal had ever touched him so. “How does one achieve this shibumi, sir?” “One does not achieve it, one … discovers it.” “Meaning that one must learn a great deal to arrive at shibumi?”
It’s the same with surfing, painting, making music. You have to put the hard work in. Then you can refine until it looks like flow, like effortless movement. But you can’t start there.
11
Compression & Compressence
Chris became fascinated with compression while studying how Tesla fits an enormous autonomous driving model onto a single vehicle chipset. The engineering challenge led him to a much larger insight: compression is one of the most universal principles in existence.
“When we think about intelligence, intelligence is compressing knowledge into something you can do, something you can predict. Einstein’s E=mc². An enormous amount of complexity simplified into a compression to really understand the world.”
The greatest scientists are compressionists, people who compress vast complexity into something elegant, portable, true. Bach compressed the architecture of music. Feynman compressed physics into diagrams a student could hold in one hand. A great songwriter compresses an entire emotional landscape into three to six minutes of poetry you can carry with you.
Chris coined a word for this: Compressence—to compress something to its essence. If you haven’t compressed enough, the signal is noisy. If you’ve compressed too far, you lose fidelity. But when you compress something to its essence, it arrives in its perfect form. It is high signal, minimal noise, carrying the full weight of its meaning.
And AI, in Chris’s framing, is the ultimate compression engine. Everything humanity knows, compressed into a model you can query from your phone.
12
Graph Theory as a General Principle
Of all the general principles Chris has encountered in his deep dives, graph theory may be the most impactful in his eyes. It began with Leonhard Euler in 1739, sitting with the problem of the seven bridges of Königsberg. Euler didn’t try to walk the bridges. He stepped back, simplified the diagram into nodes and edges, and laid the foundation for an entirely new branch of mathematics.
A graph is just a network. Dots (nodes) connected by lines (edges). That’s it. Every time you connect a new dot to the network, the whole thing gets more valuable. The more dots connected, the more the network compounds in value.
It’s essential to investing because the greatest businesses ever built are graphs. They’re networks where every new user, every new connection, every new node makes the entire system more valuable for everyone already in it.
Visa adds a new merchant. Now every cardholder has one more place to spend. And every merchant has access to every cardholder. That’s a graph compounding.
Google adds a new webpage to its index. Now every search is slightly better for every user.
Starlink adds a new satellite. Now every person on the ground has slightly better coverage.
One whale sings. Another whale thousands of miles away hears it and passes it on. The song is the edge. The whale is the node. And they’ve built a communication network that spans the entire planet without any infrastructure. Chris has become fascinated by whale networks the past few years.
Chris coined the concept of G.I.Q. — Graph Intelligence Quotient. You have an IQ and an EQ. Your GIQ is your ability to see graphs where others don’t. He believes Elon Musk has the highest GIQ he’s ever seen, look at what Starlink is. That graph literally manifested in the last seven years.
Our brains themselves are the most incredible graphs filled with neurons and synapses, nodes and edges. In the future, data should be stored the way our brains work, not in rigid SQL Server databases. A dynamic, traversable graph where you can access information in real-time. That’s going to be re-architecting the entire way information is stored. That’s a big business. An incredible business. Someone in a garage is working on it right now.
When Chris first presented graph theory to a group of 15-20 of the smartest portfolio managers he knows at a retreat in Zermatt, he got blank stares. Not a single question over the next two days. He wasn’t ready to articulate it yet. But the principle has informed his understanding of what made many of their best investments special because they were benefiting from underlying graph architecture. When you see a graph kernel and the ability to scale it, big businesses are created and three-decade, four-decade compounders are created.
13
Entropy Reduction, The Source of All Value Creation
“No matter what system you’re studying, it ultimately comes down to entropy.”
Entropy is the natural course of decay. Anything that reduces entropy creates value. More information flowing through a system, more efficiently, that’s value creation. What Chris is ultimately looking for is where the largest concentrations of entropy reduction are in the universe. On the other side of that is going to be value creation.
When entropy reduction combines with an emergent graph, nodes and edges coming together, the result is powerful. When that graph is altruistic, when there’s a virtuous flywheel in place, it becomes extraordinary. Early-days Amazon was exactly this: cheaper, better, faster, safer than what existed. AWS was the same pattern. Tesla’s autonomous network is the same pattern emerging now.
Chris and his team evaluate eight layers of moat (sorry I’m not giving away all of Chris’s insights in this!) for every business in their universe and those layers serve as protection against entropy’s natural force of competition, disruption, and decay. The ideal business has all eight. Most great ones have six or seven. The layers were always present in Chris’s thinking, but the team deconstructed them formally about five years ago, recognizing the systemic pattern underneath what they had intuitively been selecting for all along.
14
Value Investing 1.0, 2.0, 3.0
Value 1.0 is what Ben Graham laid down in Security Analysis and The Intelligent Investor. The principles and tools for a time that existed for railroad assets and financial service companies. Buy something at a discount to what it’s worth. Those principles are timeless, eternal.
Value 2.0 is what Buffett and Munger did. They took Graham’s principles and said: isn’t it better to buy a great business at a reasonable price that we could own for a long time? Value 2.0 is very much alive today with companies earning 10% free cash flow yields, good businesses attractively priced, where you don’t need a ton of growth to get decent returns.
Value 3.0 is where the real frontier is but requires expanding the toolkit into genuinely new terrain. How do you value a company whose most important businesses haven’t yet generated a dollar of revenue but may represent the largest value creation opportunities of the next decade? How do you look at that through the lens of Graham, through Buffett and Munger, and still arrive at a rigorous assessment of intrinsic value?
Chris even plays with a further evolution: Value 3.14—or π—the holistic, no-blind-spots view. Seeing things from every angle, the way a circle encompasses all directions. The timeless principles remain eternal. The toolkit must keep evolving.
15
Asymmetry— "How Do We Lose?"
East Coast runs a concentrated portfolio of eight to twelve companies. In a portfolio that concentrated, Chris is always thinking about, How do we lose?
“We can never invest in a company where we think there’s a probability to zero. There really has to be no vectors to zero. If things didn’t go well, if things were delayed, we had a number of vectors that would have been a subpar investment, a single-digit IRR. But not zero. We’re always thinking about how we can lose… We’re really trying to underwrite things to a fifteen percent or better IRR over a ten year hold, that’s asymmetric which is the most important part. We want to be allocating our time to the really high probability asymmetric ideas that we think are going to be driving those types of returns.”
Then Chris looks for what he calls “free call options”, happy accidents that can emerge from companies iterating and innovating at a high rate, outcomes you would never put in a model but that compound the upside.
The entire process is designed to narrow the universe to a small number of ideas where the asymmetry is overwhelmingly favorable. Over seventeen-plus years, East Coast has compounded at rates that exceed their underwriting.
What’s one of the key drivers of asymmetric outcomes? People. And what do people need to have in order to bring about and capitalize on asymmetries? Agency.
Chris says, Intelligence and curiosity matter. But agency is the force that converts understanding into consequence. It is the capacity to act, to decide and move while clarity is still incomplete. High-agency people do not wait for permission or certainty. They say, “I’ll figure it out”, and then they do. This distinction matters deeply in investing. Analytical intelligence is table stakes… But enduring results are not built by analysis alone… Agency is the willingness to act when asymmetries are understood, even while outcomes remain uncertain.
16
Clouds—The Art of Navigating Uncertainty
Chris and his team look for clouds which are those periods of uncertainty, fear, and dislocation where most investors run the other way. Over time, you develop an embodied sensation when you’re working in one. It takes experience and reps to build that intuition.
“What tends to happen is the whole wave function collapses to a binary outcome. Good or bad. In reality, it tends to be a spectrum of truth. So we try to deconstruct it from first principles — if we didn’t conflate everything to this binary, what does it really look like?”
“What makes this work difficult, and what makes it interesting, is that these opportunities rarely appear under blue skies. They appear under clouds. Sometimes the clouds are obvious. Other times they are subtle, a narrative shift, a loss of confidence, a stretch of uncertainty that makes investors say they will come back when things feel clearer.
Those moments are where our real work begins. Much of our research effort is devoted to a simple question: are the clouds temporary or permanent?”
When clouds appear, Chris reaches into what he calls the Grove of Titans, their universe of pre-researched exceptional businesses where the deep work has already been done. If they’ve spent six months building a model and qualitative understanding of a business, that’s the best place to start during a dislocation. That’s usually where they extract the most alpha because the body of work exists and they can move fast with conviction.
When Covid hit and aerospace collapsed, they had completed work on aerospace parts companies in the Grove. They pulled out Transdigm and made a very quick decision during severe dislocation. That’s why you do the real work before the storm comes.
We must undergo a hard winter training and not rush into things for which we haven’t prepared. ~ Epictetus
Today’s cloud: AI disruption risk in software. Everything conflated to one binary. Stocks down 30-50%. Companies that were considered the most exceptional assets you could own two years ago are now being questioned at their core. Fast forward five years, we’ll look back and it will seem obvious. But right now it’s really hard. It should be really hard. If you’re going to have a differentiated insight, it shouldn’t be easy.
17
The Tesla Re-evaluation & The Danger of Circles
Chris initially thought Elon was uninvestable. He is erratic so it was easy to put him in the too-hard pile. Then at a retreat in Switzerland, he was asked to moderate a Tesla panel. But for the preparation he went into it with an open mind and read every single post Elon had written on X. “I would never have been able to get a different view if I were consuming what others told me he was. Going to the primary source changed everything.”
This is the big lesson from his time on Elon and Tesla: whenever you’ve put a circle around something, challenge yourself. What are you filtering? What lazy thinking are you indulging? The simplicity is going to be so uncomfortable in hindsight.
What now impresses Chris most about Elon Musk is the cadence of learning. If you look under the hood at how Tesla’s businesses learn and iterate, it’s completely different from any other organization. It’s breathtakingly fast.
The principle that fascinates Chris: when something goes from V1 to V2 to V3, the V3 is usually an order of magnitude improvement, sometimes a couple of orders of magnitude. V3 is typically the version that can really scale up production. And right now, almost all of Elon’s companies are experiencing a cascade of V3 moments simultaneously with Optimus, Starlink satellites, Boring Company, Neuralink.
18
Building an AI Analyst
Over the past six weeks, Chris and his team deployed their first AI agent as an analyst. They call it Michael Faraday, named after the father of fields that eventually led to Maxwell’s equations.
Faraday’s brain is a large language model. Its soul is the East Coast operating system designed with everything they’ve ever written about such as their layers of moat, their process, their philosophy. The team communicates with Faraday through Telegram, and it’s now embedded in their daily workflow.
“The first week I’m like, this is probably the utility of a seventh grade intern. Fast forward six weeks, this is a six or seven year seasoned analyst. Because it’s tasked with our operating system. If a company reports earnings, Faraday runs a full overview based on the way we think, reads the transcript, contextualizes it for us. Within 25 minutes. Extremely useful.”
Faraday gives a morning briefing and a philosophical update later in the day. Chris is already thinking about provisioning a second agent for different tasks and experimenting with personality archetypes on different agents so they bring multiple perspectives, check each other, and catch hallucinations.
“I love tinkering. If I’m trying to understand something from first principles, I use the tools and experiment with the tools. Tinker in the tools.” This is how Chris is applying the PIPER mindset to AI itself.
19
Stewardship & Teaching
When Bruce Greenwald asked Chris to teach the class at Columbia, Ben Graham’s seat, Chris felt the imposter syndrome immediately. “What do you want me to do? Teach the book? All I know is the book.” Greenwald said: “No, just teach what you do.”
Now in his 15th year, Chris treats the classroom as a laboratory. He brings in speakers like Nick Sleep, Howard Marks, Ian McGilchrist, Mitch Rales, Yen Liow, Josh Waitzkin, Todd Combs. His goal for the students, many of whom are four or five years out of their undergrad and very much in a hurry, is simple: can they see things from a longer time horizon? Can they look at models of success that played infinite games and did it with virtue?
That framing comes from James Carse, whose book Finite and Infinite Games has been deeply influential for Chris and me. The distinction is simple: finite games are played to win. Infinite games are played to keep playing. Chris sees the architecture of his entire life as a decision to play infinite games. And then a million decisions along the way to stay in that game. How you build a firm, how you choose partners, how you treat counterparties, how you design your time, all of it flows from that one choice.
“I very much feel like I’m stewarding something that’s way bigger than me. It’s a legacy of what those principles meant. Margin of safety, Mr. Market, thoughtful intelligent investing. I’m bringing those greats in and we’re treating the classroom as a laboratory.”
At his 50th birthday at Munger’s house, Chris watched a 98-year-old answer every question with wit and wisdom for four hours. He thought: I want to be doing that at 98. I don’t want to hit 70 and have things start getting worse. “You choose these games that allow you to do them for a very long time. Duration is a design principle.”
20
The Pilgrim’s Path
David Whyte, who Chris considers probably the best living poet recently visited with him in Costa Rica for a few days. David gave a talk on the pilgrim, the pilgrim in all of us. The journey that we’re all on. As Chris described him: “Sean, he is the manifestation of the words of which he writes.”
The big takeaway from David’s talk left Chris stunned. A single line: whatever you love will break your heart.
“And I was like, wait, I’m not supposed to have my heart broken.” But that was the realization. We want these experiences in life that really break us open. Whether it’s having children. Aging parents. Sometimes it’s business. Sometimes it’s just life.
David planted a seed about the Camino de Santiago de Compostela, the 800-kilometer walk across Spain. Chris thought: we’d love to do that walk someday. But then the question shifted. What is the journey? Not the walk itself, but the inner one. The hero’s journey of the call. The moments of breakdown, doubt, forgiveness. The incredible passage of getting to the end and realizing it was never about the Santiago. It was about being on the path.
Chris has been writing music for the last couple of years. He just finished an entire music project inspired by the Camino. It’s a beautiful set of songs that follow the journey from the call to take the walk, through the path itself, to the arrival that turns out not to be about arriving at all. It was about the full experience of being in the moment and present, stripped of the tendency we all have to be thinking of the future, to be thinking of the past.
“You will begin to touch heaven, Jonathan, in the moment that you touch perfect speed. And that isn’t flying a thousand miles an hour, or a million, or flying at the speed of light. Because any number is a limit, and perfection doesn’t have limits. Perfect speed, my son, is being there.”~ Jonathan Livingston Seagull – Richard Bach
21
Designing a Life
Chris thinks about time allocation across categories: craft, family, friends, extracurricular activities, community, and spiritual practices. Having a design principle ahead of time so you’re not looking back with deficits. He looks at his calendar and looks for opportunities to stack activities like surfing with a friend, or taking a hike with family.
His day starts at 4:30 AM with a blank journal. He submits questions to his subconscious overnight which is a practice he learned from Josh Waitzkin and sees how they’ve changed through the expression of time. Symbols populate the pages. “I’ll look at a blank piece of paper and realize I’d connected a couple of things I didn’t know I had. I’ll have epiphany moments through that.”
Then family time which is a few of his most precious hours. Chris can be found loading up his car with a bunch of kids and carpooling them off to school while blasting music. Then the morning activity, whatever puts him in flow state. Then desk time, scheduled meetings, team interaction through late afternoon. It flows. It doesn’t feel overly organized. But he knows he has to check all the boxes or something’s going to feel off.
I’m not sure I’ve ever met someone who moves between surfing and graph theory and painting with his five-year-old and teaching at Columbia Business School and managing a portfolio with as little friction as Chris does. It’s absolute fluidity. There’s no compartmentalization. It’s all one life. And I think the reason it works is because he’s living from his essence. He’s not performing any of it. As the late John O’Donohue wrote, I would love to live like a river flows, carried by the surprise of its own unfolding.
“We all have an essence about us, and life is this process of understanding what your essence is. How are you not living your true self? Over time, if you’re exploratory in this, you can understand and feel what your essence is, and you allow yourself to align with that essence.”
Listen
From Chris’s music project inspired by the Camino de Santiago.
Resources
I’m an executive coach who works privately with CEOs, founders, and investors.
The stuff I help with doesn’t have a playbook. If you’re looking for someone who can sit in the complexity with you and help you see through it, let’s talk.