We Study Billionaires - The Investor’s Podcast Network - TIP231: The Mind Of A World Poker Champion w/ Annie Duke (Business Podcast)

Episode Date: February 24, 2019

On today's show, we talk to World Poker Champion, Annie Duke, about how she thinks in bets.  IN THIS EPISODE YOU’LL LEARN: Why we should make decisions the same way as making bets How to separat...e the decision and the result and why it’s important Why it makes sense to offer the right person $30,000 to spend 30 days in Des Moines (seriously!) How to seek the truth together as a group BOOKS AND RESOURCES Join the exclusive TIP Mastermind Community to engage in meaningful stock investing discussions with Stig, Clay, and the other community members. Annie's new book: Thinking in Bets NEW TO THE SHOW? Check out our We Study Billionaires Starter Packs. Browse through all our episodes (complete with transcripts) here. Try our tool for picking stock winners and managing our portfolios: TIP Finance Tool. Enjoy exclusive perks from our favorite Apps and Services. Stay up-to-date on financial markets and investing strategies through our daily newsletter, We Study Markets. Learn how to better start, manage, and grow your business with the best business podcasts.  SPONSORS Support our free podcast by supporting our sponsors: Bluehost Fintool PrizePicks Vanta Onramp SimpleMining Fundrise TurboTax HELP US OUT! Help us reach new listeners by leaving us a rating and review on Apple Podcasts! It takes less than 30 seconds, and really helps our show grow, which allows us to bring on even better guests for you all! Thank you – we really appreciate it! Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Learn more about your ad choices. Visit megaphone.fm/adchoices Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm

Transcript
Discussion (0)
Starting point is 00:00:00 You're listening to TIP. On today's show, we're extremely excited to bring you a fascinating discussion. Our guest, Annie Duke, is a master of cognitive psychology and probabilities. In fact, after completing a double major in English in psychology from Columbia University, she was awarded a National Science Foundation Fellowship to study cognitive psychology at UPenn. For people familiar with Annie, they already know she's a world-renowned poker player for two decades and has won countless titles, the World Series of Poker, and numerous championships. Annie is the bestselling author of Thinking and Betts, Making Smarter Decisions When You Don't Have All The Facts.
Starting point is 00:00:39 She's been a keynote speaker for executive staffs at Marriott, Citibank, and many Fortune 500 companies. And on today's show, we dig into Annie's methodology for decision making, how she tries to understand the odds of what appears to be improbable situations. So without further delay, we bring you this insightful decision. discussion with the one and only Annie Duke. You are listening to The Investors Podcast, where we study the financial markets and read the books that influence self-made billionaires the most. We keep you informed and prepared for the unexpected. All right, guys, we're here today with Annie Duke to talk about her new book
Starting point is 00:01:30 Thinking in Betts. And I have to say, as I told Andy just before the interview, I'm a little starstruck here. So thank you so much for coming on the show, Annie. Well, thank you for having me. I'm excited to talk some ideas. Me too. So before we talk about how our listeners can optimize their decision making, I have to ask you about one of the most life-changing decisions that you made. If we set the scene, you were 26, you were 26, you have a degree in English and psychology, you just got married and you relocated to Montana. I think for anyone, they would not say that the next logical step would be to have a long, successful career as a professional poker play in Las Vegas. But it wasn't as random as it sounds.
Starting point is 00:02:11 Could you please tell us your story? So first of all, thank you so much for the opportunity to do that, because that's not actually where most people start. Very often in the moment, when there are things that randomly intervene in your life, in the moment, we're very often very bad judges of whether that's like good luck or bad luck. It takes a lot of time for you to sort of be able to look. back and see what kind of influence that had with clear eyes. So here's basically what happens. I finish college. I go to UPenn for graduate school to get my PhD in cognitive science.
Starting point is 00:02:47 So at the end of that, I'm going off to interview for my first job as professors. My idea is I'm going to go do these job talks and become a professor. During the last year of my program, I have been struggling with some stomach problems. I'm on my way to NYU for my first talk. And I don't ever make it to the talk. I actually end up in the hospital for two weeks. I'm just really sick. It becomes clear that job talks aren't going to happen that season. And in academics, you have to wait a year because the job market is seasonal. And at the time, I had just gotten married. My husband at the time had a place in Montana. That's where his dad lived. So it was like, all right, we'll just go stay at this, you know, that place in Montana while I get better and then I'll come back and finish everything up.
Starting point is 00:03:32 This feels like very bad luck. So now I'm in Montana and I'm like, okay, I'm not in my program. I don't have my fellowship now. I need money. And I'm sick. So going and getting like what would be a regular job probably is not going to work for me because I don't know what days I'm going to feel okay and what days I'm not going to feel okay.
Starting point is 00:03:51 So my brother, Howard Letterer, who at the time was already playing poker, said to me, I think there are illegal games in Montana. Why don't you try playing poker to try to sort of fill in the financial gap. So I was like, okay, fine. So I go off to Billings, Montana, which is 35 miles or so from where I'm living at the time. And I start playing. That's what I was going to do in the meantime. And the meantime turned into 18 years playing poker. That's just sort of how I ended up there was there was there's this big intervention of luck. At the time, I felt very bad luck that sent me onto this path, that I think in retrospect turns out to be quite good luck, if I can now look at it with time having passed.
Starting point is 00:04:31 I don't think I do your book justice when I say this, but for me, the most profound concept in your book is really the concept of resulting. Could you talk to our listeners about what is that and why is that so important whenever you evaluating whether or not you made the right decision? Just tell me like in your gut what this feels like. Somebody sets you up on a blind date. It's the worst date that you've ever had. Does it feel like that was a good decision?
Starting point is 00:04:58 No, that would feel like a horrible decision to spend it not a lot of. out with that blind date. Okay. Somebody sets you up on a blind date and it goes great. The person is the love of your life and you live happily ever after. Does it feel like a good decision to go out on the date? Yes. This definitely feels like a great decision.
Starting point is 00:05:16 Isn't that interesting? In either case, I've told you the exact same information about the decision. All I've told you is you decided to go out on a blind date. Someone set you up, you decided to go. So the information about the actual quality of the decision is the same. The only thing I switched was the quality of the outcome. And you notice how intuitive it is that you're feeling about whether the decision was good or not changes depending on the outcome, even though I haven't told you much about the decision. This is what we call resulting.
Starting point is 00:05:43 Most of the decisions that we make, it's unclear to us, particularly in retrospect, whether the decision was good or bad. It's just very opaque. We can't really see into the mathematics. We don't really know what all the possible outcomes were. we don't know what the probabilities of those outcomes were. We don't really know what the payoffs are. These things are all kind of hard for us to see. When we can't see that, what we do is we use this shortcut.
Starting point is 00:06:07 I can see whether it turned out well. The date was great. The date was bad. And this is now going to tell me whether the decision quality was good. Now, this is such a strong bias that I can actually tell you something about the quality of the decision. And I can show you again how this feel. So now I'm going to tell you a little bit more about the decision quality.
Starting point is 00:06:24 A random acquaintance who you hardly know sets you up on a blind date. You go on the date and it turns out horribly. Was it a good decision? Again, I want to say no. I feel it's a trick question. No, it's not a trick question. Like literally, the great thing about all this stuff
Starting point is 00:06:40 is none of them are trick questions. It's all just about revealing your own human nature. There's no trick to it because the more that you can reveal about that self, the better off you are. So it's not about trying to think about what's the right answer. It's actually really important just to think about what does it feel like to you. Hmm. Okay.
Starting point is 00:06:55 It feels like a bad decision. And now, I've told you a little bit more, now if I ask, why do you think that's a bad decision? What would you say? It's only an acquaintance. She doesn't know me that well. He probably doesn't know my type. Right. So this is interesting because now the things that I've told you about the decision seem to align pretty well with this outcome that I've given you.
Starting point is 00:07:13 Right. So now you don't really have any trouble with it. But watch what happens now. A random acquaintance, who you hardly know, they're totally random acquaintance. They're like, have I got somebody for you? And they set you up on a blind date and you decide to go on it. And it goes great. And the person's the love of your life and you live happily ever after.
Starting point is 00:07:33 Right? Fantastic. Yeah. So what's really interesting here is that in the first case, you went to, well, it was a random acquaintance. So you could sort of see, okay, here are the holes in my decision making process. And because it aligned with this bad outcome that you had, it allowed you to sort of think that you were making a rational sort of analysis about the decision quality. But as soon as I make the person end up being the love of your life, all that washes away. And even though the circumstances are the same, it's a random acquaintance,
Starting point is 00:08:02 they hardly know you. Somehow now you're like, well, you know, what people will say is, well, you've got to take a chance. And here's the interesting thing, is that this isn't for nothing, because it actually changes our behavior going forward. When we take the quality of the outcome and either use that to figure out if the decision was good or even override information that might signal that the decision wasn't so good because in the second case, you're overriding, like it was a random acquaintance who doesn't know you. This is called resulting. I take the quality of the results to figure out if the decision was good. Now, think about how this causes us to learn the wrong lessons. Are you going to go around recommending people that they find people who
Starting point is 00:08:38 hardly know them to set them up on day? Let's take a quick break and hear from today's sponsors. All right. I want you guys to imagine spending three days in Oslo at the height of the summer. You've got long days of daylight, incredible food, floating saunas on the Oslo Fjord, and every conversation you have is with people who are actually shaping the future. That's what the Oslo Freedom Forum is. From June 1st through the 3rd, 2026, the Oslo Freedom Forum is entering its 18th year, bringing together activists, technologists, journalists, investors, and builders from all over the world, many of them operating on the front lines of history.
Starting point is 00:09:16 This is where you hear firsthand stories from people using. Bitcoin to survive currency collapse, using AI to expose human rights abuses, and building technology under censorship and authoritarian pressures. These aren't abstract ideas. These are tools real people are using right now. You'll be in the room with about 2,000 extraordinary individuals, dissidents, founders, philanthropists, policymakers, the kind of people you don't just listen to but end up having dinner with. Over three days, you'll experience powerful mainstaged talks, hands-on workshops on freedom tech and financial sovereignty, immersive art installations, and conversations that continue long after the sessions end. And it's all happening in Oslo in June.
Starting point is 00:09:59 If this sounds like your kind of room, well, you're in luck because you can attend in person. Standard and patron passes are available at Osloof Freedom Forum.com with patron passes offering deep access, private events, and small group time with the speakers. The Oslo Freedom Forum isn't just a conference, it's a place where ideas meet reality and where the future is being built by people living it. If you run a business, you've probably had the same thought lately. How do we make AI useful in the real world? Because the upside is huge, but guessing your way into it is a risky move.
Starting point is 00:10:33 With NetSuite by Oracle, you can put AI to work today. NetSuite is the number one AI Cloud ERP, trusted by over 43,000 businesses. It pulls your financials, inventory, commerce, HR and CRM into one unified system. And that connected data is what makes your AI smarter. It can automate routine work, surface actionable insights, and help you cut costs while making fast AI-powered decisions with confidence. And now with the NetSuite AI connector, you can use the AI of your choice to connect directly to your real business data. This isn't some add-on, it's AI built into the system that runs your business. And whether your company does millions or even hundreds
Starting point is 00:11:14 of millions, NetSuite helps you stay ahead. If your revenues are at least in the seven figures, get their free business guide, demystifying AI at netsuite.com slash study. The guide is free to you at net suite.com slash study. NetSuite.com slash study. When I started my own side business, it suddenly felt like I had to become 10 different people overnight wearing many different hats. Starting something from scratch can feel exciting, but also incredibly overwhelming and lonely. That's why having the right tools matters. For millions of businesses, that tool is Shopify. Shopify is the commerce platform behind millions of businesses around the world and 10% of all e-commerce in the U.S. from brands just getting started to household names. It gives you everything
Starting point is 00:12:03 you need in one place, from inventory to payments to analytics. So you're not juggling a bunch of different platforms. You can build a beautiful online store with hundreds of ready-to-use templates, and Shopify is packed with helpful AI tools that write product descriptions and even enhance your product photography. Plus, if you ever get stuck, they've got award-winning 24-7 customer support. Start your business today with the industry's best business partner, Shopify, and start hearing... Sign up for your $1 per month trial today at Shopify.com slash W. Go to Shopify.com slash WSB.
Starting point is 00:12:43 That's Shopify.com slash WSB. All right. Back to the show. So Annie, this idea is a huge part of your book. So talk to us why it's so important for people to think in probabilities. And more importantly, how can they apply that way of thinking in their daily lives? Here's how we can think about what's happening with resulting. We're acting as if the.
Starting point is 00:13:10 relationship between decisions and outcomes is much more perfectly correlated than it actually is. It's only the case that when decisions or outcomes are really perfectly correlated, that you could possibly work backwards from the outcome quality to the decision quality. And the problem is, of course, that we don't want to learn the wrong lesson. Given that it's the case that you can have a perfectly good outcome from a bad decision, we wouldn't want you then to go back and repeat that bad decision again just because you're doing this resulting thing. And vice versa, you can can have a bad outcome from a good decision. We don't want to not do that. So with resulting, what's happening is we're acting as if there isn't so much uncertainty in the relationship
Starting point is 00:13:50 between decisions and outcomes. So I'll tell you, let me give you a place where that does make sense. If we think about the game of chess, there's not a lot of uncertainty. And we can think of uncertainty in two forms. One, uncertainty in the information that there's hidden information from us. And in chess, I can see the whole position. So if I can see all of your pieces, I can know what all your possible moves are. There's nothing hidden there. The other form of uncertainty would be luck, the intervention of luck, anything that you can't control. In chess, the pieces only moved by an active skill, nobody rolls the dice, and then all of a sudden a bishop appears or disappears from the board. What that means is that in a game like chess, if all that you know, like the only
Starting point is 00:14:30 thing you know, is that I played a game of chess with somebody and I lost. So all I'm telling you is the outcome. What can you say about my decision quality compared to my opponent? If all you know is I lost. Well, you know, maybe he or she's a better decision maker. Right. In that game. And that's fine. In that particular case, it's totally fine to do that. Why? Because chess doesn't have this uncertainty. But now let's take something where we do have a lot of uncertainty. So let's take poker. Now in poker, we've got two forms of uncertainty, right? We've got the cards are hidden from view, so I can't see the person's cards. And also there's the intervention of luck. What that means is that now I can have the best hand. I can play it really, really well, and I can still lose. Going into
Starting point is 00:15:17 the last card, I could be 98% to win the hand. Two percent of the time I'll lose. Like, sometimes I'm just going to lose. Likewise, and actually, I think even more problematic is that I can have the worst hand. I can play it pretty poorly. Like, I can decide it's a really good idea to go out on a blind date that's set up by someone who literally doesn't even know anything about me. So I can have the worst hand. I can play it pretty poorly. And then it can turn out great. I could be 98% to lose the hand.
Starting point is 00:15:44 And because of the turn of the last card, 2% of the time I'm going to win. So what does that mean? That if all you know is that I played a little bit of poker, let's say a half hour of poker with somebody and that I came out the loser, now what can you say about my decision quality in comparison to there? So once you start to put uncertainty into the mix, it takes a lot more iteration in order to actually see the skills start to emerge. So you can kind of think about it like if I flip a coin once and it lands tails, that doesn't mean that I should think that tails is going to land every single time, right? It takes a lot of coin flip in order for me to sort of figure out what's going on with that coin.
Starting point is 00:16:24 And that's the same in poker. We would have to play a lot of hours together before you could actually say who was the better decision. decision maker, like a half hour doesn't do it because there's too loose a connection between decision quality and outcome quality. Okay, so what we can sort of think about is that what's happening when we're doing resulting is that we're playing chess. If I know what the outcome is, I can work backwards on a single trial. This isn't, you know, we're not working with big datasets here, you know, for most things you've got one try at it. When the fact is that we're not really playing chess, we're actually playing poker. Because if we were playing chess, then every time
Starting point is 00:16:58 you ran a red light, you would at least get a ticket. And every time you went through a green light, you would emerge on skates. But we know that that's not true. Sometimes I go through green lights. I get in an accident. Sometimes I go through red lights and nothing bad happens to me. So we know that you can't do this, right? So once we sort of have that frame and we realize, okay, we're sort of acting like we're playing chess, but we're really playing poker, you can start to see where this frame of thinking about your decisions is that actually is really helpful. Really? Really. what a bet is is this. I have options that I'm weighing and I have limited resources to invest. So I can't invest in all the options available to me. So let's simplify it and say I've got a binary
Starting point is 00:17:41 choice, option A, option B. I have resources to invest. Sometimes it's just my time. And whichever option I choose is not going to result in a guaranteed future. When I choose an option, there's going to be a set of possible futures that could occur. And each of those futures is going to have some probability of happening. That's exactly what a bet is, right? I invest in an option that then results in some sort of probabilistic distribution of outcome. And what I'm trying to do is get a positive return on my investment. I think this story is the perfect segue into my next question here. Because your book is so just packed with great stories. And perhaps my favorite story is about 30 days in Des Moines. And I do want to apologize to all our listeners out there in mind.
Starting point is 00:18:29 It might not come across us as well. But for me, that was such a hilarious story. It's become poker folklore also. But Annie, could you please tell us that story and perhaps also the more surprising learning outcome of why this story applies to all of us? My very good friend, John Hennigan, in the 90s, amazing poker player,
Starting point is 00:18:49 but also really like the stereotype of what you would think of as a 20-something guy playing poker for a living. The term that we would have used is action junkie. So an action junkie is like someone who just really like he likes to be in it. You know, he likes to be in the action. So he's playing all night. Like the game is starting at like nine or ten.
Starting point is 00:19:09 He's like playing through the night. He like never sees the sun. When he's done playing, he's like going out to the club. So this is a guy who likes his nightlife, really likes poker, loves a gamble. So one day he's sitting at the poker table and a discussion breaks out. So there's a lot of downtime in poker. So you end up like with some very strange discussions happening. on this particular day, the discussion was about state capital.
Starting point is 00:19:30 So it's like, oh, do you know the state capital of this? Do you know the state capital of this state? Do you know the state capital of this state? Do you know the state capital of Iowa? Yeah, it's Des Moines. And for some reason, like, Hennigan just announces like, oh, I could totally live in Des Moines. All right. So now he's stated a belief.
Starting point is 00:19:47 I could live in Des Moines. Now, everybody looks at him and says, yeah, right. I mean, this is like the absolute epitome of a Vegas guy. They're like, yeah, right, you could live in Des Moines. Well, so now what we have is conflicting beliefs. People at the table believe that he can't live in Des Moines. John Hennigan believes he could. And as often happens in an environment where bets take place when there are conflicting beliefs,
Starting point is 00:20:12 the adjudicator is a bet. So you have this kind of accountability mechanism that now intervenes for your beliefs where you sort of figure out, all right, let's figure out how deeply we really believe this thing. So they start to negotiate a bet. And the bet that they come to is that John Hennigan has to move to Des Moines for 30 days. Because John is capable of finding the most happening place anywhere, they can find him. They say, you can stay in this one hotel on this one street in Des Moines. And you're not allowed to stray from the street except during the day you're allowed to go outside of town to go practice golf. Now, for John, this was one of the secret reasons that he wanted to actually go to Des Moines for 30 days was he wanted a little, like I think he wanted a little detox from Vegas.
Starting point is 00:20:57 And so he was imagining that it might be good for him to take a break. But he also wanted to practice. So he was like, okay, I'm going to go. I'll get 30 days of like really good golf practice. I'll also get to detox. It'll be good for me. I'll get a break. And this is what he's thinking.
Starting point is 00:21:11 And the people on the other side of the group are just like, there's no way you'll survive in Des Moines for like one second. So they settle on a price because you always sort of put a price on your beliefs in these situations. And the bet that they settle on is $30,000. So if John can last for 30 days in Des Moines, he'll win $30,000. And if the group wins, meaning John comes home before 30 days, then they'll split $30,000 among themselves. John moves to Des Moines the next day because, you know, this is what happens. Amazing. Yeah.
Starting point is 00:21:40 So he moves to Des Moines the next day. And within two days, he calls the group. He calls a representative of the group, and he says something like this. Hey, well, you know, obviously I'm committed. So I'll tell you what, I'm going to let you settle the bet. So in the same way that we settle lawsuits, we can also settle bets for less negotiated among an party. So this is what he offers the group after his two days in Des Moines. He says, if you guys give me $15,000, I'll save you the trouble and I'll come home.
Starting point is 00:22:09 The group is like, what are you talking about? Like, you called after two days. Why don't you stay for a while? And we'll just see how this plays out. Within a week, John had come back to Las Vegas and he was paying the group $15,000 for the opportunity. Wow. What a fantastic story.
Starting point is 00:22:28 You know, the thing about the story is like, I mean, it's a really funny story. It's not really just for the entertainment value. It actually shows you something really important about what happens when you think and bet. What happens is that you get held accountable to the things that you believe. And this is actually really, really important because we can kind of think about beliefs in two ways, right? We can think about beliefs as predictions. Like, I believe that I could stay in Des Moines for 30 days.
Starting point is 00:22:53 So that would be a prediction. And we know that the nature of those predictions are probabilistic. And generally, what we do is we think about those things as yes or no. Either this will happen or it won't. And usually it's almost always somewhere in the middle that it's not that you'll stay in Des Moines or you won't. It's that some percentage of the time you stay in Des Moines and some percentage of the time you're likely to come home. And even with that, you can also think about it even as more of a continuum, which is like how many days do you stay? How happy are you going to be there?
Starting point is 00:23:25 You can imagine that none of these things are really black and white. So there's a lot of uncertainty when we're thinking about beliefs that we have about the future. So that would be prediction. So what's interesting about this mechanism of betting is that when you state something, particularly when you state something with too much confidence. What thinking about it as a bet does is it reminds you, you're going to be held accountable to that. And particularly, you're going to be held accountable to actually paying attention to how sure or unsure you are of that belief. What betting does is it asks you how sure am I? Sounds like not so much of a distinction, but it's actually quite a significant distinction.
Starting point is 00:24:01 Because when you say, am I sure, you're asking a yes or no question, which has to be black and white. you're listening either I'm 100% or 0%, which is not the way the world works. It's certainly not true of our models of the world, and it's definitely not true of anything we're predicting about the future. But when I switch that language from are you short to how short are you? Now it's no longer a yes or no question. Now I'm asking you for something that's sitting along a continuum and to examine what your own level of uncertainty is, which is a really good thing because that gets you to a more accurate
Starting point is 00:24:36 representation of the world. Let's take a quick break and hear from today's sponsors. No, it's not your imagination. Risk and regulation are ramping up and customers now expect proof of security just to do business. That's why VANTA is a game changer. VANTA automates your compliance process and brings compliance, risk, and customer trust together on one AI-powered platform. So whether you're prepping for a SOC two or running an enterprise GRC program, VANTA Keeps you secure and keeps your deals moving. Instead of chasing spreadsheets and screenshots, Vanta gives you continuous automation across more than 35 security and privacy frameworks. Companies like Ramp and Ryder spend 82% less time on audits with Vanta. That's not just
Starting point is 00:25:22 faster compliance, it's more time for growth. If I were running a startup or scaling a team today, this is exactly the type of platform I'd want in place. Get started at vanta.com slash billionaires. That's vanta.com slash billionaires. Ever wanted to explore the world of online trading, but haven't dared try? The futures market is more active now than ever before, and plus 500 futures is the perfect place to start. Plus 500 gives you access to a wide range of instruments, the S&B 500, NASDAQ, Bitcoin, gas, and much more. Explore equity indices, energy, metals, 4X, crypto, and beyond. With a simple and intuitive platform, you can trade from anywhere, right from your phone.
Starting point is 00:26:09 Deposit with a minimum of $100 and experience the fast, accessible futures trading you've been waiting for. See a trading opportunity, you'll be able to trade it in just two clicks once your account is open. Not sure if you're ready, not a problem. Plus 500 gives you an unlimited, risk-free demo account with charts and analytic tools for you to practice on. With over 20 years of experience, Plus 500 is your gateway to the markets. Visit Plus500.com to learn more. Trading in futures involves risk of loss and is not suitable for everyone. Not all applicants will qualify.
Starting point is 00:26:46 Plus 500, it's trading with a plus. Billion dollar investors don't typically park their cash in high-yield savings accounts. Instead, they often use one of the premier passive income strategies for institutional investors. private credit. Now, the same passive income strategy is available to investors of all sizes thanks to the Fundrise income fund, which has more than $600 million invested and a 7.97% distribution rate. With traditional savings yields falling, it's no wonder private credit has grown to be a trillion dollar asset class in the last few years. Visit fundrise.com slash WSB to invest in the Fundrise income fund in just minutes. The fund's total return in 2025 was 8%, and the average
Starting point is 00:27:34 annual total return since inception is 7.8%. Past performance does not guarantee future results, current distribution rate as of 1231, 2025. Carefully consider the investment material before investing, including objectives, risks, charges, and expenses. This and other information can be found in the income fund fund fund's prospectus at fundrise.com slash income. This is a paid advertisement. All right, back to the show. Holy moly, it's crazy to hear such funny stories be turned into something so mathematical and intellectual. Annie, here on the show, we often talk about people that are the best in the world at certain things. And it's not every day that we actually get to have the conversation with the people that we're talking about. But you're
Starting point is 00:28:22 here with us today. And you were the absolute best poker player in the world at a certain point. time. And like any other person that achieves that status, what is it that you would say allowed you to achieve such unprecedented success in this field? In short, how do you become the best in the world at whatever it is that you're trying to do? Well, so first of all, I think we have to remember that there's a lot of luck, right place, right time. For example, if I were to start playing poker today, I don't know that I would have been particularly good at it. The game has really, really changed. It's much more reliance on online play and playing like 20 screens at once and, you know, they're running analytics over the game and all this stuff.
Starting point is 00:29:04 Maybe I would have been good. I don't know. But I definitely, the way that the game was when I started playing suited me very well. And so I really want to recognize there's a lot of luck in that. Like I say, I may not have even ended up playing had I not actually gotten sick, right? I would have ended up being a professor or if I had been born at a different time and it was 1960, I don't know how a woman would have ended up playing poker. That would have been very strange. You know, my jeans are my jeans and my background is my background. And so whatever talent I was born with for the game, I also have to put into the luck category. Let me just start there. There was just a whole bunch of luck involved in my getting to the place that I got to. The other thing that I would say is that I had
Starting point is 00:29:48 the help of some tremendous people. And that's not just to say sort of in the generic way that I had the help of a tremendous number of people, but in the way that everybody should be thinking about how do you make better decisions to consider how the people around you, how your peers, how your mentors are actually working these decisions with you and how are they interacting with you as a group has a tremendous influence on what the quality of your decisions are going to be. So I want to think about groups sort of in two ways. There's two kind of styles that groups can interact with. File number one is a confirmatory style.
Starting point is 00:30:27 And so this is most of what we see. By the way, most of what we see in enterprises, most of what we see in politics, most of what we see in friend group is confirmatory style. And what we do is we affirm the beliefs of the group. You know, let's say, for example, that I'm in a group where people really, really, really believe in open immigration. in most groups, if I were just to say, let's think about maybe whether limiting immigration in some way might not be so bad. So I'm not saying these are my opinions. I'm just saying, like, what if I challenge this in the group? Most groups, I would get ostracized.
Starting point is 00:31:01 I'd be sort of put into line. The other way that a group can be is an exploratory style. What that means is that they're actually not trying to affirm the beliefs of the group. It's actually to try as a group to come up with what the best answer is. How do we as a group sort of figure out what the most accurate model of the world is? So now we can see in that particular group if I made that challenge. And I said, I know that we all believe in open borders, but let's consider the outside view. What would happen if you had zero immigration?
Starting point is 00:31:34 What would happen if you had these quotas on it? What if you had these different restrictions? What if you did have open borders? and you're actually exploring all of it, and you're willing to listen to what the challenges are, and in particular listen to somebody who is dissenting with your beliefs in a way that helps you to actually more accurately model the world. There are really wonderful things that come out of that, which is really, really good as a decision maker. Even in the case where it turns out that the thing that you believe is actually pretty dead on, it's still really useful to hear somebody who believes something strongly on the other side.
Starting point is 00:32:11 Whenever we actually have sort of what would be considered an opponent, even if it turns out that you think that your strategy is really good, it's very important to be open-minded to their strategy because it allows you to figure out what are the things that you can do in order to leverage their strategy to your advantage. So if I'm really open-minded to really try to figure out what's the best view that I could have of your thinking, it exposes more of your thinking to me so that I understand much better what you're doing,
Starting point is 00:32:39 which is good. It actually allows me to understand in a much better way what my own strategy is, what my own thinking is. One thing that a really good group does that this group of mentors did for me was they instilled in me this exploratory style, that in order for me to interact with this group, that I had to be open to the fact that I was wrong, I had to think about how I could have done it differently. When I said that a player was bad, they challenged me and said, why? You have to say why they're bad, because maybe they're not. Maybe you just don't understand what they're doing.
Starting point is 00:33:15 And this was forced on me by my mentors, which was really lucky because I heard a lot of other group who did this. That player is really bad. And the person would say, yeah, they suck. Let me tell you about the player that I played against who was really bad. Now notice there's not a whole lot of learning going on there. It's just sort of confirming, we're great, they're bad. that's sort of the world where my group wasn't allowing me to do that. It creates this really wonderful accountability mechanism that actually improves your decision making when you're away from the group because now whenever I'm looking at a situation, I'm processing it in the moment knowing that my group is going to challenge me later. So now it actually makes the way that I look at
Starting point is 00:33:54 the situation, the way that I process the information as it comes in, it disciplines it so that I'm much less likely to fall on my own into this sort of confirmation bias problem, into this motivated reasoning problem, into sort of feeling overconfident in my own strategy. In the end, you can sort of think like, isn't that kind of what this idea of betting does to you? You know, Annie, it's very interesting how you talk and think about decisions. And I also think that reading through your book, you contribute a lot of your success to this decision group, if we can call it that. I think that seeking for truth or this social contract you have in place with many people, if you just went outright and spoke to people, most people would probably be in what you would refer to as a confirmation
Starting point is 00:34:36 group. They might be offended or just very confused of why would you ask that question. My question to you is, how do you find like-mended people who are willing to grow with you, who you can form this group with and where you can seek the truth together? The thing that's really great about that question is that we need to understand that you can't go around in your life just challenging people to bet. Like you're not going to have any friends. If you're just going around to people like, do you want to bet all the time? People are like, what a jerk. That's number one. And number two is that not everybody is looking for this kind of interaction because this kind of interaction is actually challenging. When I listen to somebody who disagrees with me, there's three things that can happen
Starting point is 00:35:16 after I finish listening to. One is that I could continue to believe or perhaps even increase my belief in the thing that that was my side of the argument. I could change my boot a little bit in your direction or I could have a full on reversal. In any of those cases, I'm better off for having had that interaction because I understand more what I mean. So when you have a full on reversal, that's amazing because that's going to stop you from making that same mistake again going forward. Most of what's happening, it's not a full on reversal or a sticking to your guns. Mostly what's happening is that you're calibrating. And you're saying, yeah, you know, a lot of what I believed is true, but now I can really see the other side and I can see that some of what
Starting point is 00:35:56 they're saying actually has merit and I'm now going to incorporate that into my belief. The problem with all of that is that in order to actually do that, you have to open yourself up to the possibility of a full on reversal. You have to open yourself up to saying, well, I wasn't really 100% right about this, that there's some wrong in there. And the issue for most of us is that our beliefs are really part of our identity. So when somebody is expressing a belief that opposes ours, we feel like it's a challenge to our identity. And when we have to change a belief, it feels like being told that we were wrong. And in the moment, that feels really, really, really bad. So once we understand that, the first thing is we don't want to really force that on
Starting point is 00:36:38 people. If I'm just randomly having conversations with people and I'm going around saying to people, do you want to bet, I might as well be telling people, well, you're wrong. I think you're wrong. That's how they're going to hear it. And that's actually not going to do any good. So let's sort of divide the world into people who are seeking this kind of interaction, this exploratory style, and people who don't know that they want to be seeking that. So let's just divide the world into those two groups. All right. So how do you form your own group? Well, if I were to say to you, hey, if you were to think about your friend, can you think about, are there some of those friends who just sort of naturally seem interested in asking why they're wrong? Or they'll say to you
Starting point is 00:37:19 things like, where am I going wrong here? What do I not have right? When you disagree with them, they don't get upset. They're willing to hear you. Sure. Yes. There would definitely be people who if not enjoy that, but would definitely feel better about that than other friends. Yes. Right. So those are the people who you form your decision group with. So you find the people who are heading in that direction already and you say, hey, let's get together and let's actually form a decision group or a decision pod. What the goal of this is going to be threefold. We're going to commit to trying to form the most accurate model of the world as opposed to affirm the things that we already believe. So let's agree to that. Let's call that accuracy versus rightness. We're going to
Starting point is 00:38:03 reason about the world in order to try to be accurate rather than right. So we're going to agree to that. Accuracy is our king here. The second thing we're going to agree to is that we're going to hold each other accountable to the things that we believe. So that when you say something that I think is off base, I'm not just going to let it go like we mostly do. In our group, when you hear me say something that you think that I'm off base on, I am going to consider that you have harmed me if you do not point it out to me. So this flips the normal interaction on its head.
Starting point is 00:38:33 When I'm at a cocktail party and I express an opinion and someone challenges me, most people feel like that's harm. And so you're going to hold me accountable to the things that. I believe in that way because you're going to point out when you think that I'm going astray. Your book, Thinking Bad's is absolutely amazing. I'll definitely encourage everyone out there listening to this to pick it up. But Annie, where can find the book and where can they learn more about you? There's a few places. You can find the book at wherever your favorite place to buy books is, whether it's Amazon or an independent bookseller. The book is widely available. You can get it on
Starting point is 00:39:05 audio. Obviously, you can get the physical book and you can get a Kindle. I'm really hoping that people will look at that. The other way that people can interact with me, which I would love if your listeners did, is on Fridays, I send out a newsletter where I'm really writing about how do you apply these ideas to stuff that you're sort of seeing out in the world. People can go to Annieduke.com to find the newsletter there. I love that process and I love the readers of my newsletter and I particularly love that it actually creates a lot of interaction with them. Well, fantastic resource and Annie on behalf of the Investors podcast, thank you so much for taking the time to speak with us here today. Well, thank you so much for having me.
Starting point is 00:39:45 This is great. All right, guys, that was all that Preston and I had for this week's episode of the investors podcast. We see each other again next week. Thanks for listening to TIP. To access the show notes, courses or forums, go to theinvestorspodcast.com. To get your questions played on the show, go to Asktheinvestors.com and win a free subscription to any of our courses on TIP Academy. This show is for entertainment purposes only. Before making investment decisions, consult a professional. This show is copyrighted by the TIP network. Written permission must be granted before syndication or rebroadcasting.
Starting point is 00:40:26 Music

There aren't comments yet for this episode. Click on any sentence in the transcript to leave a comment.