Position Yourself for Success | Adam Robinson | Knowledge Project Podcast 168
What this covers
Chess master and investing expert Adam Robinson returns to The Knowledge Project to discuss some of the best ways to position yourself for success, how to steer outcomes in your favor, what it takes to become a learning machine, the potential uses of ChatGPT, investment strategies, and what it means to truly trust your instincts.
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00:00 - Intro 01:01 - What most people get wrong about Adam 01:28 - How Robinson feels through his decisions 08:59 - How positioning impacts decision-making 28:29 - On AI and ChatGPT 46:50 - How to become a learning machine 01:04:40 - Why Robinson hasn’t published his book, “How Not to be Stupid.”
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ABOUT THE KNOWLEDGE PROJECT Like the mentor you’ve always dreamed of having, The Knowledge Project shares timely yet timeless lessons for work and life. Past guests include Naval Ravikant, Daniel Kahneman, Jim Collins, Angela Duckworth, Seth Godin, Melanie Mitchell, & Esther Perel.
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Adam Robinson argues that superior decision-making comes from cultivating bodily intuition, strategic positioning, accelerated learning cycles, and the ability to ask better questions rather than relying solely on rational analysis.
- Human beings evolved to process information through their bodies long before logic, and modern decision-makers who ignore this intuitive signal-processing are at a disadvantage
- Positioning—the foundation from which you operate—determines whether your moves accumulate or compound toward zero; weak positions multiply losses while strong positions make most moves valuable
- Learning velocity is the engine of improvement: accelerating feedback loops and iteration (learning cycles) is more important than raw intelligence, as shown by his Princeton Review tutoring and financial software testing
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The key to learning is accelerating the number of learning cycles you go through while also getting feedback on each cycle and reflecting on that feedback to improve.
“is that is that the key to learning then accelerating the number of learning cycles and getting feedback and then reflecting on that feedback exactly right”
In poker, having the best hand in the world is worthless if you have no chips left, because you are in such a poor position that you cannot take advantage of your strength, illustrating how positioning encompasses not just the situation but your resource capacity to exploit opportunities.
“and then with poker I guess there's a lot more uncertainty but then uh how you bet and how you place those bets leads you to a better or worse position so you might have the best hand in the world but if you have no chips left you're in a bad position to take advantage of it”
In chess, if you lose a game, you are the same chess player the next round tomorrow and have not lost anything except perhaps psychological composure, whereas in investing if you lose money today you have less capital tomorrow with which to invest and compound returns, making the learning curve of investing more dangerous because you may have lost capital before becoming proficient.
“because in uh in a chess game if I lose it the next round tomorrow I'm the same chess player right I haven't lost anything maybe I'm pissed off whatever but in fact well I wouldn't be but but you know when you when you learn to compete you learn not to shake things off and not look at get emotional about things but investing if I've lost money today I have less money tomorrow to invest with and the problem with a lot of people in investing is that they're to become a a decent investor I mean just decent is a year or two that's just decent that you you're not even on the JV team yet you're just learning the ropes and and and and and if you've made too many costly Mistakes by the time you become proficient and now you're really good you got no Capital left”
Gavin de Becker's book 'The Gift of Fear' teaches that intuition—the vague sense that something is off in an environment—is a reliable early-warning system that people typically ignore because their conscious minds cannot find a logical explanation for the feeling, even though the body is processing environmental signals the conscious mind has not yet registered.
“the gift of fear and it's written by a guy named Gavin de Becker who's brilliant really brilliant the book is full of so many uh insights really a philosopher that that dude...his main thesis was this um it was a book on how to be Street Smart so you're walking down the street it's say it's at night in a city you don't really know and you have a vague sense something is off and that's your intuition tapping you on the shoulder saying get out of here yeah um and yet we look around our conscious mind looks around for for why am I feeling like this and we don't act”
Violinist Philippe Quint knew about multiple musicians who had lost expensive instruments to cabs, but concluded that none of them had actually lost their instruments and that these were publicity stunts, and then went on to lose his own Stradivarius in a cab, demonstrating the ultimate failure of observational learning.
“one of the musicians Philippe Quint lost his and he knew about all the other musicians who had lost theirs do you know what he concluded Shane what he concluded that none of them had lost their instruments he concluded they were publicity stunts he so could not imagine that somebody yeah there's no way you're no ma because that would crush him it would devastate him for years that's crazy but notice but it's not so crazy he he himself dismissed it because they didn't really lose their instruments”
Human beings consistently ignore warnings because they believe warnings apply to other people but not to themselves, exemplified by people ignoring medication warnings that state 'do not operate heavy machinery or drive' because they think the warning doesn't apply to them personally.
“human beings always ignore warnings they always do and and so they dismiss it they go yeah whatev um that's true by the way even on medicine bottles you know it says a warning uh this medication may affect your mental and physical functioning if affected do not operate heavy machinery or drive right and most people think that that doesn't apply to them yes does it go oh what if like that's for other people exactly right for other people like yeah they may be affected and but I don't know if I'm affected and I'm fine right”
Buffett and Munger are keenly aware of staying within their 'circle of competence'—knowing the kinds of industries and situations in which they have deep familiarity and only investing in those areas—which is a key principle for avoiding mistakes.
“we're going to get to that and a i and chess and positions I'm gonna weave all that together because your question is so profound so um so the chessboard I see everything and in my calculus I am taking into account the fact that I could be mistaken I can make a mistake and I wouldn't know it in other words if you make a mistake in your reasoning or you overlook something by definition you're not aware of it but in the Game of Poker I don't see your full hand I don't even know the cards that I'm gonna get right and so I'm assessing um all kinds of probabilities right and then on top of that even if I had all of all of the cards I could also make an error in my judgment and so one thing is to to be aware of um positions that you excel in right uh uh uh again you being such a scholar of of uh uh uh uh the resident at uh Farnam Street um that uh Buffett and Monger um are keenly aware of the kinds of industries that they know well and the kind of situations those companies in those Industries they're completely familiar with them”
Framing is a big thing, and it connects to mental models—the frames we use shape our thinking and behavior, and using better frames leads to better outcomes.
“and framing is a big thing it uh at Farnham Street right your mental models and frames and so the instead of the distraction frame huh we're giving them more choices what to do with their time”
Before the internet, finding an answer to a question required potentially hours of travel and research (trip to library, finding relevant book, searching for answer), but now it takes milliseconds, which dramatically accelerates learning cycles.
“so back in the day uh say before the internet if Shane you had a question or I had a question or whoever's listening to this right now you're the listener if you had a question pre-internet days you'd sit there going is it worth my while to make a one-hour trip to the public library maybe find a book on the topic maybe yeah yeah um maybe that relevant book will have an answer and maybe the answer will be something that I can actually use so you're looking at a two or three hour investment and most of the time you might have gone nah yeah okay now on the internet you can do that in milliseconds”
A CEO does not want a chief marketing officer to present 47 different choices; instead, they want 3 choices because dealing with too many options becomes overwhelming, suggesting there is a cognitive limit to useful choice expansion.
“like a CEO of a company does not want the chief marketing officer to give him 47 different choices give me three and I'll make the call but don't I don't want to have to deal with you know 47 choices but at least initially and just sort of like okay let me see what my choices are and then we got to start narrowing it down”
General Patton's principle 'never tell your men how to do anything, tell them what to do and let them surprise you with their ingenuity' empowers subordinates with agency and allows for creative problem-solving, though in combat situations direct execution of commands is necessary rather than questioning the objective.
“and because he was the General never tell your men uh how to do anything tell them what to do and let them surprise you with their ingenuity right and um but even that even that suppose General Patton said we need to take that Hill now in battle you got to take the hill you you don't have the perspective and you can't go huh maybe Eisenhower a patent was wrong maybe we shouldn't take that Hill”
An office building had complaints about elevator wait times, and engineers proposed solutions like express elevators to frequently used floors, but the real problem was not the wait time but people's complaints about waiting, and the solution was to install mirrors so people would be distracted rather than bored.
“a um a state-of-the-art uh um office complex goes up and from day one there are complaints from all the tenants about the weight for the elevator takes forever to for the elevator to arrive and uh so they call in one engineer after the next and uh they say well you can increase the speed by having an Express Elevator and these are the three most frequented floors in terms of elevator times that we've tested so just dedicate one to go to that anyway so they all worked around um how to how to decrease the weight time because that was the question how can we decrease the wait time but that wasn't the problem the problem was not that people waited the problem was that people complained about the waiting and so that uh a um and they bring in an architect and he he says oh you don't have to speed up the elevators just put mirrors in in every waiting area”
Robinson co-founded the Princeton Review with John Katzman and in the early days tutored 10-12 hours a day, 7 days a week, seeing 60-90 students per week, which gave him 60-90 learning cycles per week on every question in standardized tests.
“back in the day I co-founded the Princeton Review with John katzman and when I started off I um I was a tutor and in the early days I was tutoring um 10 to 12 hours a day seven days a week do the math yeah that meant I was seeing 60 to 90 kids A week...I was seeing kids every hour on the hour from seven in the morning till seven or eight at night”
Franchises like McDonald's systematically capture and disseminate successful discoveries (like the 'Would you like fries with that?' phrase discovered by a teenage girl, which increased sales by 7%), representing a business model that intentionally accelerates learning cycles across a distributed network.
“there's a kind of business that does that very well franchises so franchises there could be a franchisee say of McDonald's in Buffalo New York who goes oh on rainy days use this phrase...now that phrase was discovered by a girl I believe it was a teenage girl I forget what town but she discovered that a lot of people said sure why don't you throw in some fries and they discovered seven percent of the people say yes to that that's one person in fourteen”
There are two fundamental ways to live: avoiding pain or seeking pleasure, and Buffett's insight that 'never lose money' (Rule 1) and 'never forget rule number one' (Rule 2) is genius because human enterprise, learning, and growth are inevitable, so as long as you avoid losses, your money will grow over time.
“I think we talked about this but I'm not sure um there's two ways to live your life one of them is um avoiding pain and the other is seeking pleasure and um and you know uh better than anyone Buffett's first rule of investing never lose money right and Rule Number Two never forget rule number one and so why is that important because his his insight and it's a genius Insight is you can't help but make money over time just because human Enterprise that is learning and accumulating and growing so over time the value of any Enterprise of any business uh is going to grow um and so as long as you avoid loss um your money will grow”
Robinson argues that understanding what positions you excel in and which ones you do not is crucial because in chess, all pieces are visible (complete information), whereas in poker, you have incomplete information about both your opponent's hand and future cards, making position assessment more complex in poker but equally important in life decisions.
“so um so um um chess if you if Shane and Adam are playing a game of chess we see all the pieces it's not like you've got a piece behind your back that you're hiding and Adam look at that and look away and you put the piece on the board oh no yeah we see I see everything that you see you have complete information complete information right complete information”
Human beings as animals learned to process information in their environment through their bodies long before the Greeks invented logic, and as a species we have lost that ability to process information somatically despite its evolutionary primacy.
“we learned to process information in our environment way before the Greeks invented logic right and even the word logic comes from the Greek word for Logos and words and human beings to survive had to well heck animals to survive process information in their bodies and we've lost that as a as a as a as a as a world as a species we've lost the ability to process information in our body”
The survival of human ancestors depended on this non-conscious, body-based threat detection and response system; consciously analyzing a threat gives a predator time to attack, whereas instinctive physical response preserved the species.
“there wasn't even a millisecond I just leapt and um because and even to this day I don't know how I physically could have moved that far but I did and uh and the survival of of of my ancestors depended on doing that um totally right”
The book 'The Talent Code' by Daniel Coyle discusses how Brazilian soccer players develop superior skills, and a key mechanism is that they play on smaller, compressed fields (30 feet instead of full field size), which increases the number of ball touches and passes each player experiences per match.
“there's a great book I think you've mentioned it before that there's um I think the the Talent Code and uh there's that guy's name kroyler yeah yeah anyway brilliant book great great book I think it was in that book um um and they talk about um how Brazilians play soccer really well I remember that yeah and one of the ways they play is to have instead of a hundred a hundred me like a a instead of playing on a a field that's like a football size yeah they shrink it down so it's like 30 feet which means that the learning Cycles are much faster they have to take more shots they have to pass more often it's accelerate”
JPMorgan outperformance relative to other banks is slightly bearish for financial stocks and the broad market, reflecting a 'flight to safety' where investors move to the safest banking stock, suggesting fear in the market.
“so jpmorgan's outperforming is not it's not is uh slightly bearish for financial stuff uh interesting yeah yeah it's slightly outperforming sorry it's slightly embarrassed not hugely so and when it's underperforming it's slightly good now again you have to Define just like with chat CPT or anything if uh Define outperforming like so what do I mean by that over what time frame is it outperforming by how much but I can put all of that in and just say broadly jpmorgan's outperforming is not good for financial stocks and not good for and and also not great for the broad Market and uh when you think about it intuitively there's a little um um there's a little bit of flight to safety there it's the safest banking stock so if it's I'm performing people are a little scared right”
ChatGPT functions as a lightning-fast research assistant and deductive/analytic machine capable of logical conclusions, but it is not yet capable of making logical leaps that aren't evident from the domain—it cannot make genuine creative or innovative insights.
“the way to think about it is um is that it it's a super smart um uh Lightning Fast research assistant it doesn't come up with insights it it doesn't and I fed it situations where I had an Insight like around the Princeton Review and things that I know about markets so I'd I'd give it the data I had it it's not able to make is not able to make it's able to make logical conclusions think of it as uh it's a really good deductive analytic machine um uh but it's not yet capable of making logical leaps that aren't evident from from the domain”
Yo-Yo Ma left his three-million-dollar Stradivarius cello in the back of a cab in 1999, an incident that was major news, and subsequently nearly a dozen famous musicians lost their instruments in almost identical circumstances—always after performances, always while traveling—but Robinson's research shows this pattern of repeated mistakes.
“you'll remember at the beginning of the book I talked about musicians who had lost their instruments exactly right so those of you who don't know a 1999 Yo-Yo Ma Yo-Yo Ma the great uh cellist left his cello in the back of a cab and this was Front Page New York Times you know news is a three million dollar Stradivarius...and by the way back then it it it's worth way more than three million...about nine months later another musician in exactly the same circumstances loses forgets his violin in the back of a car exactly the same situation and he had read about Yo-Yo Ma...I did research they were like a dozen famous musicians who all lost their instruments almost exactly the same situation always after a performance always when traveling”
Julian Jaynes' thesis in 'The Origin of Consciousness in the Breakdown of the Bicameral Mind' argues that consciousness as humans currently experience it is a recent phenomenon, emerging only about two to three thousand years ago, somewhere between Homer's Odyssey and Iliad, and that the ancients who built the pyramids and developed mathematics were not conscious in the modern sense.
“there's that great book by uh Julian James the origins of Consciousness in the breakdown of the bicameral mind and his thesis was that Consciousness such as you and I experience it like right now you and I are conscious that we are on a podcast talking to each other uh but...Consciousness is pretty darn recent in human history and by pretty darn recent he he said somewhere in the last oh somewhere between Homer between the Odyssey and the ill The Odyssey and what was the other book Homer wrote anyway between the two Homer novels that uh poems um Consciousness was born in the human species so only about two three thousand years ago”
Each person has a unique vocabulary and way of processing information through their body; learning to recognize and trust your own body's signals requires developing personal awareness of how your specific nervous system communicates—this varies from person to person.
“the way your body processes information and your intuitive insights about the world about others it's going to have a different vocabulary from Shane's or atoms and you have to learn that”
In the future where machines can answer anything, the competitive advantage will go to those who can ask the best questions, making question-asking ability the key differentiator in education and all domains.
“when you've got machines that can answer anything the edges who asks the best questions that's key and the better questions you can ask the more you're gonna get out of the out of whatever AI thing you're using so how do we learn how to ask better questions then”
The intuition and body-based warning system discussed regarding street safety applies equally to investment dangers, relationship dangers, contractual dangers, and all types of decision-making, and should be refined rather than ignored.
“that same intuition is speaking to you all the time about various dangers in your environment whether they're investing dangers or relationship dangers or contractual dangers whatever it is um and to not not ignore that and in fact the opposite really um uh refine that that you the instrument of your body as a as a um as an early morning system and as totally as a computer in its own right”
People always learn the wrong lesson from events because they think about themselves or other people rather than imagining themselves in the situation: they read about someone making a mistake and think 'I would never do that,' preventing them from learning the lesson.
“why do people I will tell you flat out so what what did I conclude and then I'm gonna get to have an announcement I'll share with you if you if you're game for it so um um is people always learn the wrong lesson because they think either about themselves or about other people they they read something in the newspaper about somebody doing something outraged they they go oh I would never do that people don't learn is they can't imagine themselves in that situation”
The correct lesson from the pattern of musicians losing instruments would have been: 'If they lost theirs under what circumstances might I lose mine?' rather than dismissing the pattern as not applicable.
“the question he should have said is if they lost theirs under what circumstances might I lose mine that's not the lesson he drove so I have to write in a chapter into into the um into the uh um in the book into the book that that warns people of that”
Robinson found that young fundraisers for Save the Children were using a monotonous approach ('Excuse me sir/ma'am') and suggested they experiment with different approaches to see what works, and he notes that organizations lack systematic ways to collect and scale successful experimental discoveries.
“I watched them for about five minutes with my friend and I said Kim I just want to do something so I I called all three of the kids together right there college kids and I said I'll give you five hundred dollars if you'll listen to me for five minutes...I said I've been watching you for the last five minutes and each one of you approaches passers-by with basically the same thing excuse me sir excuse me sir or ma'am or whatever and I said has that been working for you guys no it hasn't well then why don't you try different things”
George Soros famously said that when his back is acting up, he knows something is wrong in markets, indicating that human beings process information in their bodies even during financial decision-making, not just consciously.
“George Soros famously said that when his back is acting up that he knows something is wrong in markets”
Robinson gives the example of Yo-Yo Ma with a cello to illustrate how a master musician like Yo-Yo Ma can coax more beautiful music out of an instrument than an ordinary musician, just as a skilled person can get more value out of ChatGPT as a thought partner than an unskilled person.
“in the same way that Yo-Yo Ma can coax more um beautiful music out of a cello than you or I could I don't know how to play the cello um but you know Yo-Yo Ma can can take a cello and and get it to do way more than any other cellist and in the hands of a master what you can do with chat GPT as a as a as a thought partner”
Robinson uses Google's autocomplete feature as a research tool by typing the beginning of questions (e.g., 'How can I learn to...') to see what questions people commonly ask, revealing what is on people's minds and what entrepreneurs should address in their products or marketing.
“I I often go to Google and run what I call Google experiments so I will type in the beginning of a question and see what it auto suggests right it auto completes right and I think we talked about this uh yeah right how can I learn to if you type in how can I learn to you'll see the number one question people ask on on the Internet is how can I learn to love myself right”
A better question than 'How can I learn to love myself?' would be 'How can I learn to love?' because removing the self-focus and judgment allows for more foundational learning before applying it to oneself.
“but here's a question that here's a better question because we're talking about making questions better here's a better question than how can I learn to love myself is how can I learn to love hmm let's remove yourself and all that judgment around it okay how can I learn what does loving mean what does that mean to love let's take it away from myself for the Moment”
The concept of the 'question behind the question' refers to understanding the deeper context or need that motivates someone's stated question, and answering the surface question without understanding the underlying need leads to poor advice.
“and even there I'll introduce the notion of the question behind the question so for example a friend could come up to me and say uh Adam you know any good books on meditating but what's the question behind that why do you want a book I'm meditating oh because I want to give it to my teenage daughter because she's stressed in school and I figured if she had because if he said my teenage daughter is stressed right and she's I'm trying to offer ways constructive ways that she can handle the stress and I was thinking meditating books right by giving me the context he gives me Adam more choices in how to comment it right”
Robinson argues that 'distraction' is not the best word for what mirrors do in elevators; instead, they 'invite the tenant to use the time in another way,' which is a more positive framing that suggests agency rather than passive distraction.
“I'm going to jump on the word you use distract okay but it's great yeah no it's great because I I I I would use the word distract too but let's improve even that so what we're doing is we're inviting the tenant to use the time in another way right as opposed to a distraction like distracting from right a distraction assumes if I'm trying to focus on writing a paper right then noise outside is a distraction from that”
Learning should be treated as the fundamental process of human life, and people should ask themselves daily 'What did I learn today?' to ensure they go to bed smarter than when they woke up in concrete ways.
“I might describe actually life as learning that's what life is a plant doesn't I don't know plant is alive it doesn't really learn anything it can't modify Its Behavior right...as human beings we learn and we should be learning um every day we should be learning every day...what did you learn today and you want to go to bed smarter than when you woke up yes in concrete ways”
Robinson created software to test ideas about financial markets, which dramatically reduced the time required to test a hypothesis from about one hour (with spreadsheets) to about five seconds, thereby accelerating learning cycles and allowing him to test many more ideas in the same time period.
“every day I created software to test ideas about markets so back in the day uh say before the internet if Shane you had a question or I had a question...you'd sit there going is it worth my while to make a one-hour trip to the public library...now imagine that in markets so well what what you've really accelerated is sort of like the learning Cycles exactly exactly you remove the friction like instead of taking three or four hours to learn something now it takes milliseconds perhaps...I still remember I was seeing kids every hour on the hour...and um and uh I remember there's this one girl...I had 60 and I taught each kid each week the same test which meant I had 60 to 90 learning Cycles on every single question in the test”
Tim Ferriss reviewed Robinson's manuscript and said it seemed 'kind of obvious,' which Robinson later realized was Tim being stupid about stupidity—Tim was dismissing the insights as obvious rather than realizing that the obviousness of wisdom is precisely why people ignore it.
“Tim who said um that seems kind of obvious...I sat with that and I realized I say this affectionately uh Tim was being stupid about stupidity he was dismissing so I Define stupidity as overlooking or dismissing conspicuously crucial information and Tim was dismissing it he was dismissing it as kinda obvious”
Life itself is learning—the difference between living organisms and non-living things is the ability to learn and modify behavior in response to experience.
“I might describe actually life as learning that's what life is a plant doesn't I don't know plant is alive it doesn't really learn anything it can't modify Its Behavior right and I mean it doesn't preset ways right like heliotropic it'll turn towards the Sun but it's its responses its range of response is pretty limited and so as human beings we learn and we should be learning um every day”
Robinson's maxim is: 'whenever things are a little strange, they're very strange,' meaning if something seems slightly off in a public setting, it is actually significantly wrong and one should remove oneself immediately rather than trying to figure out or assess the situation.
“here's another Maxim that I've uh sort of a riffing on his point whenever things are a little strange they're very strange so that I know in a public setting if I'm walking I walk into a room and I go huh if something is seems a little bit off then I then it's really off and I don't wait to um figure out to assess the situation I remove myself from it immediately”
Instead of asking 'How do I X?' (e.g., 'How do I get to London quickly?'), ask 'Who knows how to X?' because this reframes the problem from a self-focused solution to a network-based solution, immediately expanding your available choices and options.
“whenever you find yourself asking how do i x how do I get to uh uh um London quickly or how do I increase um marketing how do I increase sales and also increase the sales price of the of the item I'm selling how do I do that instead of asking how do I ask the following question who knows how to do whatever that is so all of a sudden instead of my trying to figure out how I Adam ought to do it mm-hmm I've got lots of choices now the it's okay I gotta find someone who knows that and that gives me lots of choices instead of my thinking okay what are my constraints what am I doing here”
As managers, bosses, teachers, and parents, the more context and positioning you can give others (which is to say, understanding their situation), the more choices they have and the better decisions they can make, illustrating how providing context increases agency and capability.
“but yes um but as uh as managers as bosses as teachers as parents in relationships the more choice we can give the other person which is to say the context which is to say to go back to your word the position and then I'll know oh your real question is this”
Robinson's principle is never to make a decision when confused, tired, or stressed—states he calls 'the stupid zone'—and this principle is difficult to remember in real-time situations because it requires recognizing a feeling state rather than purely rational deliberation.
“one of my principles is um never make a decision when I'm confused now that like okay but that doesn't sound like such a big deal but I have made decisions when I was confused or tired or stressed you and I would call it in in the stupid Zone and and um and it's important to remember those things in real time again A Feeling state”
Identifying the kinds of positions or situations in real life where you tend to excel and the ones where you do not is a skill that should be developed, because some people might do well in certain situations while others do not, and there are no universal 'good positions'—only positions suited to individual strengths.
“and and and that also is a really important uh skill for for anyone to develop is in what kinds of of positions in real life you could call them situations right do you tend to accept and in which ones do you not”
Robinson is including a chapter in his book that warns readers not to fall into Quint's trap—not to dismiss others' losses as publicity stunts or failures that couldn't apply to them, but instead to ask the crucial question: 'If they lost theirs under what circumstances might I lose mine?'
“but it's not so crazy he he himself dismissed it because they didn't really lose their instruments he should the question he should have said is if they lost theirs under what circumstances might I lose mine...I have to write in a chapter into into the um into the uh um in the book into the book that that warns people of that”
ChatGPT and similar AI tools are less impressive for simple tasks (like generating vegan menus) than for their potential as thought partners that help users ask better questions, and Robinson uses ChatGPT to help formulate better questions rather than relying on its answers.
“so um so chat GPT is fascinating and really everyone should be using it right now so in its trivial thing it can answer questions like um you you could open up your refrigerator uh see what items you have in the refrigerator and in your pantry and say I'm preparing a dinner party for vegans give me some menus and it'll you know it can answer questions that it's pretty impressive but what excites me most about about uh chat CPT and again um that's what we know about has been released you've got to believe that there are companies and government organizations that are way ahead of where what you and I see is chat CPT for like always keep that in mind so um so I use it as a thought partner I use it to to help me ask better questions the key thing is not that it can answer questions um it's that it gives me a tool to ask even better questions”
Even when ChatGPT is wrong, it is useful because it explains its flawed reasoning, allowing the user to identify the error and learn why the AI arrived at an incorrect conclusion, making error valuable as a learning tool.
“well but I don't care even when it's wrong it tells me why would it have flawed that right exactly right and so even when chat CPT is wrong it's useful again I'm not using it for its completeness I'm not um”
All advice is implicitly a warning, and all wisdom is a warning; for example, 'the best way to boil an egg is this' carries an implicit warning that if you don't boil it that way, the egg won't be as good, making wisdom fundamentally precautionary in nature.
“all advice is a warning all wisdom is a warning if I say the best way to um to boil an egg is this there's an implicit warning if you don't boil it like that the egg is not going to be as good as it could have been yeah right if I say the best way to negotiate a contract is to always let them make the first offer there's a warning if you make the first offer you're not gonna get as good a result”
The speaker prefers quiet, slow chess positions with minimal piece interaction for 10-20 moves (like those arising from the Queen's Gambit opening) where they can carefully arrange pieces before combat, and deliberately engineers the game from the opening to steer toward positions of their preference.
“I like uh quiet uh slow positions where there's not much interaction with um my opponent's pieces for about 10 or 20 moves I like kind of getting my pieces all arranged just so before the battle starts right and so there are certain openings like anyone has watched the Queen's Gambit the Queen's Gambit is an opening um and uh speaking of which um um so so the positions that arise from the Queen's Gambit you Shane might like those positions and I Adam just just because of my nah aesthetically I just I don't like those positions or I tend not to do well in those positions right so I'll steer the game as much as I can from the very opening to positions that are of my liking right in other words I'll engineer that”
The best decision-makers in the world almost always operate from a position of strength and a solid foundation, where nearly every move they make is good and accumulative, whereas when operating from a poor position, things almost always deteriorate from bad to worse.
“it strikes me because when you operate from a solid position or Foundation nearly every move you make is good it's all accumulative whereas when you operate from a poor position things almost always go from bad to worse”
The problem with the Socratic method is that the teacher does the work of asking questions, but learning requires the student to develop the ability to ask questions themselves; this is why machines that answer questions change the game—students must now learn to formulate their own inquiries.
“so to see the kinds of questions that people come up with and and it's it's a really important exercise um that uh you know the problem with the Socratic method is that Socrates the teachers doing all the work yes right you have to do the work to get the to know the questions to ask right and it's it's think about school the teacher asks the questions and the students you know raise their hand and give the answer that's machines are gonna do that you gotta know what questions to ask yes right”
By Wednesday of each week, the speaker could predict which answer students would incorrectly choose on question 13 of a test, because he'd run so many learning cycles that he understood the patterns of student errors.
“so I would try out different explanations as I went through the week by the time it was Wednesday I basically knew every error that a kid was gonna make on that test I would know on question 13 the kid probably chose C like I you know and I would say is that is that the key to learning then accelerating the number of learning cycles and getting feedback and then reflecting on that feedback exactly right”
The bicameral mind breakdown theory posits that before consciousness emerged, human brains had conversations between left and right hemispheres, but people were unaware these conversations originated internally and instead attributed them to external voices from the Gods.
“a conversation arose in our brain and at the time we weren't aware of it before before again because of the breakdown of the bicameral mind bicameral is uh two Chambers like the uh Congress of the Senate and the House of Representatives by camera right two Chambers and so the the left and the right brain the breakdown he said it's been many years since I read it as a as a teenager he he said um that conversation arose and we didn't know where it was coming from and we attributed it to the Gods”
Rather than critiquing Ferriss's dismissal, the speaker took it as a prompt to investigate why humans ignore warnings and dismiss obvious wisdom, leading him down a deeper research path about stupidity.
“what I was saying now if you thought a little more he would by the way I'm not critiquing Tim on this I'm not whatsoever because it sent me down a rabbit hole and I learned a ton Tim could have said Adam Buffett said get this book out there I'm going to give you an endorsement and yet it seems obvious to me so what am I missing he didn't say that he assumed he knew it already and think about so I realized that the the key Insight was that all Buffett said this book is loaded with good ideas and appropriate warnings warnings um and I know something that Buffett maybe didn't think about human beings always ignore warnings they always do”
When Robinson reads an idea, he pauses at least once a minute to process it in his body by stopping and feeling how it feels somatically, which helps him navigate ideas through his felt sense rather than purely rational analysis.
“when I read an idea say in in one of your podcasts right I'd read a transcript I'm reading something or or reading a quote or reading anything I'll often pause and when I say often at least once a minute I'll pause and I'll process it in my body so what I mean by processing I'll just stop for a moment and see how it feels in my body”
The best way to teach meditation to a teenager who is a dancer is not through books (which keep the person in their head) but through physical movement-based practices that work through the body, illustrating how understanding context allows for better, more tailored solutions.
“and go well the best way to learn meditating is not from a book that's just going to get her in her head yeah right and they're physical things and because I know your daughter is a Dancer she meant like this kind of movement meditation right”
Robinson wears a top hat that he purchased from a hatter (milliners make hats for women) two summers ago from a shop in New York, and when he walks down streets in New York (like SoHo) he receives at least one compliment per block, and in restaurants he receives compliments at least once per meal.
“right now you see me with my top hat on and I've taken to wearing this um I bought it uh um uh two summers ago I was walking by a Hatter in New York a proper Hatter who makes hats for people milliners make hats for women anyway and I see this hat in the window and it just I just smiled when I saw it and I walked in and uh and I got one so this is made to me my head and why do I say that Shane if you were in New York um and next time you are we will do an experiment you and I will walk down a street say in SoHo and I promise you that at least once a block I will get compliments”
ChatGPT can be used to improve sales approach: a used car salesman could describe their car to ChatGPT and ask what questions potential buyers would ask, allowing them to anticipate objections they hadn't thought of.
“I give you a perfect example you could say um um let's say I'm I'm um I want to come up with a new product you know and uh I could describe the product I could describe the kinds of of um ah here simple example I'm a used car salesman I could describe the car and um and say what kinds of questions will people ask about that car and and it might might say to them and go whoa whoa I would have forgotten to to deal with that I have to have an answer to that question right”
A trader might recognize they perform poorly during the opening hour of markets or on days when the FOMC is about to make announcements, and consciously avoid trading during these situations because understanding your own positioning constraints is crucial to long-term success.
“A Trader for example might know there's a certain kind of I don't do well the the opening hour I'm always messed up and you know um or I don't like dealing with uh fed report days like you know in the fomc is about to make an announcement I'm just I'm not going to look at the markets during those days and so we learn the kinds of positions in which we Excel”
Wearing the hat that gets positive responses feels good and opens you to serendipity—you didn't deliberately seek compliments, but the positive feedback is rewarding and creates a virtuous cycle where you want to wear it more.
“that's key in terms of like you're just opening yourself to Serendipity you didn't do it for a reason but then when you got feedback that it made people smile it makes you almost want to wear it more it does absolutely who doesn't like seeing people smile when you when they see you”
A good question is one that prompts other questions or increases the choices available to the decision-maker, thereby expanding the solution space rather than constraining it.
“a good question is one that prompts other questions or a good question is one here's another uh way to comment and a good question is one that um increases the choices that I have so um I Adam as a decision maker”
Robinson has another top hat (slightly larger) that generates no positive social responses, demonstrating that small differences in positioning or presentation can have large effects on outcomes, and that feedback (in this case social responses) reinforces behavior.
“I got such a good response with this why am I saying that because I have a hat a top hat just like this with with with a little bit bigger that gets no responses none whatsoever none I have no idea why I have no idea why but I don't wear that one too much because it's fun for me when people say hey nice hat”
Robinson has written a book called 'How Not to Be Stupid' that he has been developing, with endorsement from Warren Buffett, who said 'This book is loaded with good ideas and appropriate warnings,' and Robinson defines stupidity as 'overlooking or dismissing conspicuously crucial information.'
“and he endorsed it was his Christmas present one year in the and so the endorsement is um uh this book is loaded with good ideas and appropriate warnings...I Define stupidity as overlooking or dismissing conspicuously crucial information”
Robinson describes a personal experience in Central Park approximately 30 years ago where he was jogging and suddenly leaped laterally about 10 feet without conscious thought, later discovering a crouching bronze mountain lion statue 15 feet away that he had perceived through peripheral vision before conscious recognition, demonstrating how the body can execute protective responses faster than conscious awareness.
“I'm jogging along and go ah and I left I mean laterally like 10 feet like I still don't know how I did it and my heart is pounding I'm going what the heck and I'm like I'm looking around and like what the heck is going on and I'm kind of embarrassed like like does anyone see me do that and um I'm trying to catch my breath and my eye scans up the embankment and about 15 feet so the event was about 15 feet and then there's a lot of a Shrubbery Central Park full of dense Shrubbery and stuff there's a crouching mountain lion a crouching mountain lion now it's a statue”
Every year on Warren Buffett's birthday (end of August) and Christmas, the speaker sends Buffett a gift, and once sent a 1936 nickel (Buffett's birth year) as a birthday present with the message 'Dear Warren, Happy Birthday, this is your allowance, spend it wisely'.
“every year on his birthday and at Christmas I send Buffett a present and um and so every year about a month before that day I'm like oh man what am I gonna do this year because it's not an easy person to to get a perfect presence right it's not like he needs another tie right um and uh so once um one year I sent him a nickel so but it was a special nickel so every um to amuse myself um over the years I've adopted the practice if I have any coins in my pockets of course at the end of the day you take them out of your pockets I spill them out on a table and I search through them to see if I can find any old coin and I Define an old coin as um as um um anything before 1960. okay so I the oldest coin I've have so far is a 1907 penny it's worth 300 bucks I found it I I not like I'm gonna sell it but just wow I found an old coin so I've turned it's in it's a little Adventure when I pull the coins out it's like do I find a new coin so I happen to have a nickel from 1936. so one year that was his birthday present I wrapped it up so those of you who don't know um Buffett was six years old in 1936. so I sent him a I wrapped the nickel up very like it was a coin collector nickel it wasn't I just found it but I wrapped it up very nicely and with a birthday card I said Dearborn uh Happy Birthday um uh this is your allowance spend it wisely”
OpenAI was founded by Musk, Sam Altman, Reid Hoffman and others with the belief that AI is too important to be owned by any single company or country and must be treated as a global commons or shared resource because the stakes are too high.
“open AI was started by Musk and uh Sam Altman who's running it now Reid Hoffman a bunch of his uh old Posse and uh it was started with the noble belief that AI is too important in the world to be owned by anyone uh company or or country it's just two the stakes are too big it's got to be a a Global Commons like a shared resource”
Buffett responded to the 1936 nickel gift with an email (which is rare since he doesn't typically do email), thanking the speaker and saying he's 'thinking hard about how to spend my allowance'.
“and he shot me back uh something that very few people in the world have ever gotten do you know what I got I don't know if I told you no okay an email oh awesome see you know that right he doesn't do it now right so I've gotten I've gotten a few and I they're more those of you who don't know Buffett religiously does not do email um anyway so he said Dear Adam uh thanks so much I'm thinking hard about how to spend my allowance”
The primary goal in 'The Upgrade Hour' with Shane and Adam is to provide practical, usable information that listeners can immediately apply to their lives, not merely interesting intellectual ideas.
“one of the things I wanted to say at the beginning Shane um one of the things I well one of the many things I love about you is that you are on a constant hunt a safari for usable information really usable and I I wanted to to to emphasize um both of us to anyone listening to us right now that everything here the goal is to provide practical useful information not well that's an interesting idea right this is this is the uh the upgrade hour with Shane and Adam right and how to upgrade yourself how do we use it”
OpenAI is not as open as it used to be, and there are other open-source AI companies like Stability AI competing in this space, though companies and government organizations are likely ahead of what is publicly released as ChatGPT.
“now it it's not quite as open as it used to be there's some other open source companies like stability Ai and and there's I think one or two others and and so so chat GPT is fascinating and really everyone should be using it right now so in its trivial thing it can answer questions like um you you could open up your refrigerator uh see what items you have in the refrigerator and in your pantry and say I'm preparing a dinner party for vegans give me some menus and it'll you know it can answer questions that it's pretty impressive but what excites me most about about uh chat CPT and again um that's what we know about has been released you've got to believe that there are companies and government organizations that are way ahead of where what you and I see is chat CPT for like always keep that in mind”
When one additional condition is added to the JPMorgan analysis, it becomes 'really bearish,' and the opposite conditions are 'hugely bullish,' but the speaker cannot reveal what that condition is.
“but if you add in one more condition um it's really bearish with adding in one more condition that I got to test about three minutes later I that I can't reveal um but if you add in another condition it's really bearish and and the flip side is the opposite conditions it's hugely bullish”