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

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 devas

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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. F

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

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 in

About Lucky Maverick
About Jonathan Bales

This is the audio version of “I Spent $35,000 on a Video You Can Find All Over the Internet.”
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This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit luckymaverick.substack.com