Lucky Maverick: The Art and Science of Betting on Yourself

Jonathan Bales
Lucky Maverick: The Art and Science of Betting on Yourself

A podcast for independent thinkers luckymaverick.substack.com

  1. 03/17/2023

    The Eight Most Impactful Concepts That Changed My Life (And 30 Other Important Ideas)

    About Lucky Maverick About Jonathan Bales At one point in my life, I thought that in Pizza Hut’s “Makin’ it great” ad campaign, they were actually saying “Brickin’ a brick.” I mean I was a toddler, but still. Brickin’ a brick. I believed this for years, even when I was old enough to logically understand “brickin’ a brick” doesn’t make any f*****g sense. I always thought it would be funny if a big company ran a huge ad campaign with a slogan that was totally meaningless just to see how it would perform. That’s what I’d do if I were in charge. “McDonald’s: Ready for the lightning?” Then we’d spend millions of dollars on it, maybe changing the classic ‘M’ logo to add in lightning bolts, and then I’d get fired. It didn’t matter that I believed Pizza Hut’s slogan was “Brickin’ a brick.” I got by. Even if I believed it today, it probably wouldn’t change much for me. It’s okay to have beliefs that are wrong. Most thoughts—and even actions—don’t matter. The majority of what you think you know is probably wrong, and most of what’s right doesn’t mean s**t anyway. Sometimes, though, you come across an idea that’s truly impactful to your life. It might still be wrong, but at least it’s useful for you, which is better than being wrong and useless I suppose. I think the value of knowledge probably grows exponentially such that most of it is basically worthless but a small percentage is overwhelmingly valuable. This has been my experience, anyway, as a few basic ideas capable of shifting my worldview have been more valuable than everything else I know combined, so I’ve tried to prioritize finding this rare knowledge that actually makes a difference, blocking out almost everything in search of the truly scarce stuff. With that said, I thought it might be cool to talk about the most impactful ideas that have changed my life thus far. The main criteria I used for selecting these is that each idea is something with which I at some point either disagreed or didn’t even really comprehend. It’s really important to get adequate sleep, but everyone knows that. These are all ideas that at some point I didn’t grasp, but ones that made profound impacts to my life once I did. The Big Concepts Convexity Errors, randomness, and “the unexpected” should help you, not harm you. If you’ve read my articles for more than 10 minutes, you probably know I’ve learned so much from Nassim Nicholas Taleb. From black swans to antifragility to being a giant dick to anyone who disagrees with you on Twitter, I’d say I owe more of my success to Taleb than anyone else I’ve read, even if he’s a total dick on Twitter. The main idea that’s changed my worldview is convexity, and specifically the concept of acquiring more benefits than harm from chaotic events. Whereas most people focus on improving prediction accuracy—and sometimes in areas in which that’s nearly impossible—few properly focus on the payoffs, which are more easily controllable and offer a larger usable edge in terms of competition. I applied this to DFS by focusing on ownership and lineup composition instead of projection accuracy. That is, maybe this player or team that everyone thinks will do well actually will, but maybe they won’t, and if they don’t, how can I benefit to the greatest degree? One way to apply convexity to your life is to mimic evolution: * Don’t suppress chaos. Natural selection is what Taleb would term “antifragile”—the opposite of fragile—because not only is it not harmed by chaos, it benefits from it. A species can change for the better fairly quickly in evolutionary terms from a single random genetic mutation. Even natural disasters are positives for most species as a whole, assuming they’re not entirely killed off, because they end up coming back stronger and more prepared than before. Humans, too, are hopefully more prepared for the next pandemic; COVID has been devastatingly brutal, but “good” and “bad” are designations that often change based on your time horizon. What’s bad in a static environment can often be one of the most beneficial things when viewed long-term. “Failure saves lives. In the airline industry, every time a plane crashes the probability of the next crash is lowered by that. So these people died, but we have effectively improved the safety of the system, and nothing failed in vain.” By embracing chaos in all aspects of life, you’re set up for more sustainable long-term success. That’s one reason I tweeted this: Not all jobs are the same and every person is different; there’s no one-size-fits-all plan for everyone. In fact, most people are probably best off in the employee role. Generally speaking, though, one of the biggest misconceptions about being a salaried employee is that it’s safer than something like an independent contractor. Being a contractor isn’t always a great solution—it’s not feasible in some areas and takes a long time to build a customer base—but who do you think is more susceptible to a sharp change in income: someone making $70,000 a year from one employer or someone earning the same amount from eight clients in two different niches? The latter is more volatile, but the former is riskier. Evolution embraces chaos, and in exchange eventually delivers the best results. Without that volatility, there could be no progress. “Nature builds things that are antifragile. In the case of evolution, nature uses disorder to grow stronger. Occasional starvation or going to the gym also makes you stronger, because you subject your body to stressors and gain from them.” Don’t deprive yourself of life’s shocks; they’re what allow for your personal evolution. * Think long. Evolution needs time to operate. This is a characteristic of things that like chaos; they love time. The more time, the better, which runs in opposition to most things, which eventually break down over time. Many people are doing things—whether professionally or personally—that, unbeknownst to them, will not survive over time; they’re eventually going to go busto, as we say in the gambling world. If we’re being honest, most people can’t even calculate expected value in static environments. A much smaller percentage know how to do it over time, choosing what’s optimal in arenas in which the first order of business should be eliminating risk of ruin, i.e. “not dying.” Natural selection does this better than any business in the world; it’s built into the system. Species maximize their chances of survival as a whole above all else. Survive, then optimize. Build systems that embrace volatility and are meant to survive and improve with time. Via negativa Addition by subtraction This is a simple concept, which is that to improve basically anything in life, first look at what you can take away before adding anything. Unhealthy? What are some things you can remove from your diet or lifestyle before adding something like supplements? Unhappy? What can you remove from your life before taking antidepressants? The ‘via negativa’ concept is related to an approach I’ve discussed when it comes to winning games, which is to reverse-engineer a strategy by starting with what success looks like, then working backwards by removing the paths that don’t lead to winning. Think of how a sculptor creates a statue from a slab of concrete; the “truth” of the statue is already there, hidden and waiting to be realized, but only after removing that which isn’t necessary. Leverage Big wins require big leverage. I used to make the majority of my money as a freelance writer. I liked it and hated it at the same time. I liked that I was in control of how much money I made (sort of), and I disliked that I was broke and forced to write all day long to get by. Still, I can write pretty quickly, so once I got rolling and had some companies paying me, it was a decent income. But in terms of making short-term money, I had no ability to apply leverage. What I mean by that was I got paid for what I produced, and that’s it. I was paid for my time, which can become quite tempting if you can quickly create things of value. However, I almost always tried to write evergreen articles I thought could live for a long time. I wasn’t sure why I wanted to do that; it just felt right for some reason. It was one of the best decisions I made because writing in that way was a form of leverage. That’s actually the idea behind what I’m doing right now with this newsletter—building up long-term equity (in the form of trust) that can be cashed in at a later date. I’m not charging for it and I don’t have immediate plans to do so, but my guess is that writing things that (hopefully) help people will always be a valuable use of my time. Traders are of course familiar with leverage, which can make smart men very rich and dumb ones very poor. The same is true outside of markets. I recently wrote about leverage in Sam Hinkie, Leverage & Dynamic Decision-Making. The key to finding real success is to figure out what works and apply leverage. Fundamental to this idea is understanding and accepting today’s wealth is not created by how hard someone works. You’ll have a difficult time becoming wealthy by getting paid for your time. You have to get paid for the value you provide others through your unique knowledge, multiplied by the leverage you place on it. The returns from this sort of work—amplified by the internet—are compounding. This increases the importance of logical decision-making. When the results of your decisions are non-linear, it amplifies their impact. If you consider yourself a sharp decision-maker and you have unique knowledge or skills, there’s never been a better time to get rich. The theoretical bounds of the value you can extract are nearly limitless. Acquire specific knowledge or develop a unique skill. This is a

    30 min
  2. 02/10/2021

    The Key to Being Contrarian: Think Like a Kid

    About Lucky Maverick About Jonathan Bales If you want to break the rules of grammar, first learn the rules of grammar. - Kurt Vonnegut I used to play this iPhone game called “Fun Run.” It’s sort of like Mario Kart in that you race and there are question mark things you can get that have weapons to kill your opponents (lightning, a bear trap thing, a sword, etc). When I first started playing, I tried to move as fast as possible and finish the race with the quickest time I could. Seems logical…faster is better in any race, right? Maybe, maybe not. You need to perform well to win a race, but the goal isn’t to have the fastest time you can; it’s to have a faster time than everyone else. Those are similar ideas, but not exactly the same. Once I started playing Fun Run more and more, I did the most psychopathic s**t you can imagine and began charting all of the details of the game in Excel—my time, the course, kills, deaths, etc. I was doing this to see which courses were my best because players got to vote on one of two before the race, so I thought that optimal selection would slightly improve my win rate and also I wasn’t a virgin at this time if you can believe that. As I tracked the data, I noticed that while my win probability improved, my times barely got better. Why? It was due to the recognition that, while fast times and wins are correlated, the former is really just an effect of the latter, not always a cause of it. There are many times it benefited me to reduce my expected time to increase the odds of winning, such as going out of my way to obtain an additional question mark, using a super low-variance strategy late in the race if I’m winning, taking more risks when I’m losing, and so on. In all games, you work within the confines of the rules to find edges and increase your chances of winning. Sometimes, though, specifically as you become well-versed in a game and begin competing at the highest level, you realize world-class performance requires a completely different way of thinking. Why is it that in so many areas—from poker to business to video games to chess—the greats seem to be playing a fundamentally different game than their opponents? The path to greatness starts with learning the rules of the game and figuring out how to play within the rules to win. But it eventually transforms into breaking all those rules, approaching problems from a distinct viewpoint to play a game—one I’ll call the “hidden” game—that’s fundamentally different from others. Speedrunning This article was inspired by an email I received about something called “speedrunning.” Hi Bales, When reading Lucky Maverick articles, I find one area that continuously applies these concepts: speedrunning. If you're unfamiliar with speedrunning, it is a community of gamers that attempt to beat video games as fast as possible. For example, the current world record to beat Super Mario Bros on the NES is 4:55.314. Speedrunners are fighting over frames and fractions of seconds to secure world records, which is why they have to apply some of the tenets of the Lucky Maverick posts. The two main strategies that are applicable in speedrunning are taking ideas to their logical extreme and playing the game by different, hidden rules. A great example of this is in the speedrun for Wii Sports Resort Golf. The main strategy that runners realized after thousands of attempts was that they were able to manipulate both wind and cup position by intentionally failing the first hole. This is counterintuitive to conventional thinking of “the fastest way to play Wii Golf is to just get the ball in the cup as quickly as possible.” By finding these hidden mechanics of the game, and taking them to their absolute extreme, these runners were able to take the world record down multiple minutes from the early days of running. I really enjoy your newsletter and would be happy to discuss speedrunning further if you'd like. Feel

    26 min
  3. 01/29/2021

    You've Been Kidnapped

    About Lucky Maverick About Jonathan Bales You’ve been kidnapped. That’s probably not the start to the day you were looking for. It was already going to be a long day, what with accounting all over your ass about those expense reports—Suzie needs to just lay off if you ask me—and now you have to deal with this s**t? Your kidnapper is a little different than most; he loves statistics and game theory and randomness, and he’s going to let you play a little game to determine if he’ll hold you hostage. No, the kidnapper is not me, although if I were a kidnapper, I’d let anyone free who could beat me in a best-of-101 rock-paper-scissors contest. Meaning I’d never let anyone free. Sentence fragment for dramatic effect. And another. Something you shouldn’t try unless experienced. We’re not playing rock-paper-scissors though. The kidnapper puts three cards on a table, two of which say “MINE” and one of which says “FREE.” He knows which are which, and he tells you that you can leave if you choose the card with “FREE” on it. Damn, a 33% chance of freedom. And even worse, a 2-in-3 chance Suzie’s week-end accounting is going to be askew. She’s already in Robert’s ear about your frequent tardiness. You stay late though, unless you have to pick up the kids, so she really just needs to back off. “Why are you telling me all this, and who tf is Suzie?” asks the kidnapper. “Just pick a f*****g card.” You pick the first. “Nice choice,” the kidnapper says with a laugh before turning over the middle card, which reads “MINE.” With the first card (yours) and the third card still face-down, the kidnapper asks, “Now, would you like to switch cards?” Think about it. Would it help to switch to the third card? You had a one-in-three chance from the start, so does it really matter which card you select or if you change your choice? Are your chances now 50% since there are just two cards remaining? What’s your pick? The Monty Hall Problem This is of course my version of a puzzle you might have heard of called the Monty Hall problem, named after the host of a show called Let’s Make a Deal on which a version of the game was played. I presume some of you have heard of the brainteaser, so I’m going to focus mostly on the implications of the answer, but the gist of the solution is this… Your choice not only matters, but it matters a whole lot, doubling your chances of going free if you make the change. My initial reaction when I heard of this solution was sort of disbelief because it felt so counterintuitive, but it’s right. The key component of the decision that’s easy to overlook is that the kidnapper has knowledge of the cards and, when he makes the choice to show you one of the “MINE” cards, it’s a huge piece of new information. Let’s say the order of the cards is MINE, MINE, FREE… The scenarios can play out in this way: * If you select the first card, the kidnapper will show you the second. If you choose to stay with your choice, you’re his. If you switch, you’re free. * If you select the second card, the kidnapper will show you the first. If you choose to stay with your choice, you’re his. If you switch, you’re free. * If you select the third card, the kidnapper can show you any other card. If you choose to stay with your choice, you’re free. If you switch, you’re his. By changing your selection, your odds of freedom increase from 1-in-3 at the start of the game to 2-in-3. That’s due solely to the knowledge of the kidnapper and his decision to turn over one of the “MINE” cards. Some Takeaways I think the Monty Hall problem is a really interesting game theory and psychology puzzle that has far-reaching implications on the framework we use for certain decisions. * Difficult dilemmas often require counterintuitive solutions. When you first encounter the Monty Hall problem, it just seems sort of obvious it doesn’t matter what you do. The solution—that it’

    17 min
  4. 01/27/2021

    If You Ain't First, You're Last

    About Lucky Maverick About Jonathan Bales “If you ain’t first, you’re last.” I don’t know if wiser words have ever been spoken. We should all try to think a bit more like the great Ricky Bobby. There are different ways one can aim to be first. In a car race—where everyone starts from roughly the same point—speed is what matters. Small differences in speed compound over great lengths; a little bit faster car will go a whole lot farther over hundreds of miles. It reminds me of this passage from James Clear’s Atomic Habits: Imagine you are flying from Los Angeles to New York City. If a pilot leaving from LAX adjusts the heading just 3.5 degrees south, you will land in Washington D.C., instead of New York. Such a small change is barely noticeable at takeoff—the nose of the airplane moves just a few feet—but when magnified across the entire United States, you end up hundreds of miles apart. Your starting point can have a profound impact on where you end up over long time horizons…if you can’t make adjustments. When you board an airplane and it takes off, though, it doesn’t really matter all that much if the pilot is off by a few degrees. I wrote about this idea in my article How to Improve Your Decisions Immediately: By focusing on choices as existing dynamically, it increases the value of trial-and-error. That is, when you can iterate to “change” the EV of a decision repeatedly over time, it decreases the importance of prior choices. This should be obvious in the airplane example: would you rather be on a cross-country flight with a pilot who spends countless hours attempting to calibrate the most precise takeoff angle but can’t make adjustments along the way, or one who just sort of takes off in the general direction of New York but can make unlimited adjustments? Uh, yeah, the second one. In my article The Secret to Success: Mimic Evolution, I added: The faster and more efficient you can make this trial-and-error cycle, whether it’s in your personal life or your business life, the quicker you will find success. Your starting point for truth is way less important than your process for refining and improving your beliefs, especially when you get away from a static worldview and begin to (appropriately) see it dynamically. Over time, differences in the speed at which you can process information and adapt become exponentially more important than where you begin. By speeding up your trial-and-error cycle, the returns compound over time; being twice as fast doesn’t make you just twice as better, but rather exponentially so. Recently, though, I realized that my claim that “your starting point doesn’t matter” is seemingly at odds with another Lucky Maverick principle I hold to be true: the easiest way to maximize payoffs is to limit competition, and perhaps the best way to limit competition is to be first (or early) to a particular niche. When I look back at my personal triumphs and failures, there’s indeed a trend of finding more success when I’m somewhat early in finding new trends, whether it’s business or crypto or, recently, Topshot (see why I spent $35,000 for a video you can find all over the internet). That’s not to say I’ve been “first” by any means, but simply that the degree to which I’ve benefited from getting involved in a new project is very much correlated to how “early” I found it. And, at the extremes, the benefits of timing are magnified and non-linear. Buying Bitcoin six months after its launch wasn’t four times more valuable than two years after; it was monumentally more valuable. Investing in Topshot moments one month after the site launched wasn’t four times more valuable than four months after; it was dramatically so. The timing of finding a potentially lucrative niche is a sort of “singularity” of value; the closer you get to the starting point, the more extreme the effects become. As you approach that singularity and the payoffs become inten

    15 min
  5. 12/18/2020

    Sam Hinkie, Leverage & Dynamic Decision-Making

    About Lucky Maverick About Jonathan Bales Note: If you notice Jake’s voice sounds like he has the flu in the audio version, don’t worry…he doesn’t have the flu! It’s just COVID. I started fishing last year. Like any hobby I take up, I’ve become intensely serious about it to the point no one around me wants to be involved. I started tracking aspects of every catch in Excel; in just over a year, I’m up to 53 different species, not to brag. My goal is to catch as many species as possible. If you ever see someone snagging lunker largemouth bass all day…that ain’t me. I already got that species. No need for more. I’m more of the type to be fishing for microspecies in a puddle using hooks that can blow away with a slight breeze. You don’t know what it’s like to feel the strength of a fish until you’re lightly tugging a minnow out of a puddle using a piece of a worm the size of a grain of sand for bait. Just raw power. Racking up species in fishing is all about leverage. The rod itself is a type of lever, letting you easily reel in even very powerful fish that are much stronger than you in water. I also often use multiple rods—usually one with the bait sitting at the bottom, one in the middle of the water column, and then actively using one with a spinner or topwater bait. You can use three rods at a time where I live, but theoretically, you could use quite a few more rods to increase the number of fish you catch without substantially more effort. Well, the key to finding success—and specifically to making money—is the same as it is in racking up fish species smaller than your pinky: figure out what works—where the fish are and how to catch them—and apply leverage. Leverage in Today’s World Many of my thoughts on leverage have been inspired by Naval Ravikant. Check out his famous tweet thread on how to get rich (without getting lucky): As Naval has pointed out, there are many different types of leverage, with the oldest form being labor: getting people to work for you. This, along with capital, are what people generally think of when it comes to being an entrepreneur or starting a business. And typically, that’s what business has meant: hire employees and raise money to grow. Labor and capital are forms of permissioned leverage, meaning you can’t really just employ them on your own. You ultimately need someone’s permission to work with them, and you need permission to access others’ money. The internet has created new forms of leverage, however, that do not require permission. What I’m doing right now—writing online—is a form of permissionless leverage. I don’t need anyone’s approval to post this, yet it supplies ultimate leverage on my time. This article can live forever, and whether it’s seen by 10 people or one million, there’s no additional work for me. And if I do a decent job, a whole lot of people will trust in me more and more, and that compounds over time in a non-linear way. Software is another form of permissionless leverage. When I co-founded FantasyLabs, we didn’t need to ask anyone if it was okay that we did it. We built a product that can effectively run on its own, 24/7, and scale without any additional work. We can acquire more and more users at nearly no additional cost, whether its more energy or money; no matter if we have 100 users or 100,000 users, the costs in both time and capital are effectively the same. That’s leverage. The internet has created a world in which there’s an abundance of money-making opportunities that allow individuals to earn like companies, but most people don’t yet realize it. There’s a reason we built FantasyLabs as a data and tools platform rather than a service to give picks. One is sustainable and can grow without additional work; the other cannot. There’s a reason I write almost no content that’s time-sensitive. This article doesn’t have an expiration date and can continue to “work” for me forever; a time

    15 min
  6. 12/14/2020

    How to Win a Bet: 6-12-18-24

    There comes a time in every man’s life when he must stand up for what he believes in. With the world against him and no true believers on his side, he digs deep, knowing he must fight for what’s right, regardless of the lack of support, and stand firm in the face of mounting opposition. Victorious or not, he will come out the other side filled with a pride few will ever know—a pride experienced only by the rare breed of man with the courage to look evil directly in the face and, not because he has no fear, but in spite of his fear, gain a paradoxical and unparalleled strength to proclaim “I. WON’T. BACK. DOWN.” When the dust settles, he’s transformed into a warrior. A hero. A man of honor. For me, that was a day filled with masturbating for money in Las Vegas. This is my story. This will be part of a “How to Win” series in which I break down how I went about figuring out the optimal way to win a bet, beat a game, or solve a problem. It’s an extension of my in-depth analysis in How to Win Games, which I’d suggest checking out if you haven’t. Part of my theory on winning games—as I discuss in the principles of Lucky Maverick—is that the same sorts of concepts tend to apply across all forms of games, and that if you can learn how to think about and win any game, you can learn to win every game. Most of life’s problems can be turned into a version of a game, so learning to win games, in my opinion, is a recipe for finding success in just about any area you want. The Importance of Rules and the Art of the Negotiation In 2018, I booked a bet with my buddy Adam Levitan on something called the 6-12-18-24 Challenge. If you’re unaware, the bet involves assigning each of those numbers to one of four tasks, then completing all of them within 24 hours. Your missions: eating donuts, drinking beers, running miles, and jacking off. The plan was to complete the challenge in Vegas before the official start of the Gambling Olympics. I wanted to post our actual chat log when booking the bet to show how we went about deciding on the “rules.” The rules—and hidden rules—are of incredible importance because winning any game boils down to working within the confines of that game to find edges that increase your win probability. All of the strategy and meta game are ultimately an effort to unearth EV by exploiting the rules better than your opponents. Knowing the rules—inside and out, truly—is so simple and yet so overlooked as an advantage by most. *Note: Skip to the next section if you just want to read how I went about “solving” the 6-12-18-24 challenge. Or just skip right to closing this browser window if you have any sort of dignity.* jonathan.bales [12:48 PM] what odds are you guys giving me on 6-12-18-24? you said 10 to 1 levi? I think that’s fair :) adam.levitan [12:49 PM] i said nothing.. let’s nail down the official rules.. all your miles have to be under 10 minutes and outside? jonathan.bales [12:49 PM] I mean whatever you want that’s clearly way harder and a potential problem though 10 min is actually hard to do for possibly 12 miles I mean it’s almost a half marathon adam.levitan [12:50 PM] oh i assumed you were running 6 jonathan.bales [12:50 PM] idk if I can JO 12 times after some practice yeah I mean I am gonna have to but I’m running out of steam on these JOs adam.levitan [12:53 PM] if you’re running outside and averaging a 10-minute mile while running them consecutively i can give you 6-1… but I’m not going to give you a lot of action on it, can’t let you beat me for like 30k jonathan.bales [12:53 PM] consecutive? that’s way different don’t think I can do that at all I assumed I could take a break after each mile peter.jennings [12:54 PM] Im on bales side adam.levitan [12:54 PM] oh well then i don’t see why you couldn’t do it you’re in way better shape than the dude who came on the pod and did it and you drink every day doughnuts are easy just gotta get the j

    26 min
4.6
out of 5
19 Ratings

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