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Lucky Maverick: The Art and Science of Betting on Yourself
The Key to Being Contrarian: Think Like a Kid

The Key to Being Contrarian: Think Like a Kid


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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 shit 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.


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 free to reach out/or use this as a topic if you are interested.



A few notes:

  • I love when you guys send me emails with awesome stuff you’re reading, watching, or otherwise learning about. I can’t always give super-long responses—and sometimes the emails suck ass, no offense—but for the most part, they’re really great. I imagine the average Lucky Maverick reader is either a super-sharp worldly scholar or a degenerate gambler who responds to his grandmother’s innocent claim that it takes less than 10 minutes to drive into town with “Oh yeah, how much would you bet? I’ll give you 2-to-1.” Anyway, keep sending me sweet content that you’re enjoying.

  • In this particular case, I’ve gotten deep into the lab on speedrunning. Even if you’re not that into video games, the way in which the top players go about solving each game is this absolutely beautiful combination of efficiency and innovation—shaving fractions of a second off of their times with small optimizations while also making giant leaps through completely outside-the-box tactics.

  • I’d say I’ve played an average amount of video games in my life—maybe a bit less—but like everything I’ve done, rather than a healthy and balanced approach, I’ve become completely obsessed with just a handful of games. As an example, I was the No.2-ranked player in NCAA Football on Xbox for a two-year period in high school. I played all day long, every day, and I’d have my little brother put on the headset and talk smack to my opponents so they’d tilt their faces off thinking they’re getting whooped by a six-year old. I played like 15 hours a day, which tells you that no matter what you do in life, there’s always someone out there, somewhere, who is a bigger loser than you.

This article is going to be about how to truly think differently, using speedrunning as a foundation for the main points. It’s not required, but I’d check out this video and others from the same name—Summoning Salt—on YouTube.

Let your curiosity—and not the need to win—guide you.

Not all who wander are lost.

– J.R.R. Tolkien

I’ve been playing racquetball with my friend Adam Levitan for a few years. I sucked when we started. I never played a racquet sport and my cardio was total shit, whereas Levitan was in decent shape and had played tennis for years.

My only hope was to hit the ball up into the ceiling so it would bounce high off the front wall and slowly drop in the back, hopefully bouncing weirdly in the corner. I wasn’t good enough with my racquet to consistently hit winners and if the game became too fast-paced, I basically looked like a fish out of water, flopping around, completely unable to breathe.

But I became curious about racquetball and began watching pros on YouTube. It turns out that Kane Waselenchuk and Rocky Carson and all our heroes on the court didn’t play like me, if you can believe it. Sometimes they hit flop shots, but I realized that it would be impossible to win long-term against a great player without hitting very low, accurate winners into the corners.

Another thing I noticed my friends Kane and Rocky didn’t do was continually smash their racquet into the court when they lost.

I watched hours of play, and they literally never repeatedly banged their racquet into the ground until it was demolished, then immediately order a new one on Amazon. Not once! I blame Amazon Prime and their uber-fast and reliable shipping. I’d have much better sportsmanship if it weren’t for that fucking Bezos.

Smashing my racquet into pieces was a reflection of my hatred of losing, but here’s what that racquetball experience taught me and what I believe is the most important trait in those who think differently to achieve greatness: your path toward perfection must be governed not by a need to win, but rather a natural curiosity and passion for what you’re doing.

I really believe this is the primary key to being contrarian, non-consensus, non-conformist…whatever you want to call it. A pure, child-like curiosity will take you off the beaten path to identify the best long-term strategies, not because you’re trying to be different, but because children at play have no choice but to wander.

Make no mistake about it: a will to win is absolutely vital. I’m as competitive as anyone I know, hence why my racquets have a shorter lifespan than a gastrotrich. It’s a marine microorganism that lives three days. Now you don’t have to look it up.

However, in choosing to win at all costs, what you’re really doing is sacrificing the war to win a battle. If I never attempted to hit more winners in racquetball—which temporarily lowered my win rate—then I never would have improved enough to consistently win.

So the need to win is still an essential trait, but it can’t be over a short time horizon. It’s sort of like Amazon continually delaying profits. They’re a company designed to make money, yet have chosen to push back short-term net income in favor of a long-term view.

If you extend this idea to its logical extreme, the optimal time horizon for greatness is “forever,” meaning you should let your passions and curiosities dictate your direction. Doing so has compounding advantages over optimizing for the present moment, and those advantages can be “cashed in” for wins at a later date.

Just as Amazon and other great companies invest in innovation, you can achieve long-term greatness by investing time in following your curiosities—by “wandering.”

Don’t stop at local maxima.

Wandering in business is not efficient…but it’s also not random. It’s guided…and powered by a deep conviction that the prize is big enough that it’s worth it to be a little messy and tangential to find your way there. Wandering is an essential counter-balance to efficiency. The outsized discoveries—the non-linear ones—are highly likely to require wandering. 

- Jeff Bezos

When you don’t let yourself wander, you’ll inevitably accept “good enough.” Say an alien is beamed down to our world and asked to find our tallest building. Let’s just forget for a minute how incredibly advanced this alien civilization would have to be just to get here, and let’s instead assume it’s just some regular old dumb alien with human-level intelligence. We’ll call him Joe.

Joe is dropped onto Earth. He walks around a bit, learns how to hail a taxi, and starts exploring. Eventually, he spots a very tall building and finds his way to the top. He looks out in every direction as far as his single alien eye can see and nothing is taller.

“I did it! I found the tallest building on this planet!” Joe exclaims, in English somehow. Happy with his accomplishment, Joe sends word back to his home planet.

“I already found it, guys. Didn’t take long at all. If you need me, I’ll be here on top of the Radisson Hotel in Fargo. It’s over 200 feet high!”

This is one of the dumbest analogies I think I’ve ever had. I mean this is really fucking stupid, but I wrote too much and I’m not deleting it now. Moving on…

Joe is at a local maximum—the highest point in a given range or a larger set.

Just like Joe on top of the Radisson, when you’re at a local maximum, you usually can’t see that there are much higher points that can be reached. Joe might have taken the stairs and it might have been very difficult and he could have felt a great sense of achievement once he reached the top…but he’s still on top of a hotel in North Dakota.

And the only way to improve is to explore, to wander, to seek out what might be uncomfortable out of pure curiosity. This means being below more recent highs almost all of the time. If your goal is to be good or even great, your quest for new maxima need not be strenuous.

But if your aim is to be the best—if it’s the equivalent of Joe making his way to Dubai to find the Burj Khalifa—then you have no choice but to explore. That means passing on other local maxima—giving up future “wins”—by becoming a kid again.

Long-term greatness requires exposing yourself to short-term hurdles; if you’re truly exploring, most of the time you’re not going to be at a peak, but rather at a much lower point looking for something better.

Side note: I can’t find the article, but I saw a really cool breakdown with a formula of the “optimal” number of people you should date before getting married. If you consider the average amount of time it takes you to get to know someone, how quickly you can meet new potential partners, and when you’d like to get married/have children, there’s actually a formula you can employ to maximize your chances of finding the best possible person for you.

The interesting thing is that, mathematically speaking, you should continue to meet, date, and then break up with people, no matter what, until a certain point. I remember putting in my numbers and the calculator said it would be suitable to date 17 people, leave all of them, and then continue to date people until I came across the first one who’s better than the best from that group of 17.

This approach is forgoing local maxima in effort to optimize the odds of finding a true maximum given your time constraints. If you think about it, this happens naturally so much more than it used to. Whereas older generations would frequently date and marry people from their hometowns, the ease of travel and, specifically, the internet and dating apps has made it much, much easier to find suitable partners—to traverse the topological map of dating—to forgo the local maxima.

At some point, though, you need to make a choice. If you settle too soon, you’re very likely to end up at a local maximum, but if you are always searching for something better, that doesn’t seem like a great recipe for happiness either. Maybe I’ll find it and write about it, I just thought the concept was really cool, and it can be applied to everything from job-seeking to esports to buying a house. Wander, then optimize. And for all the straight men out there, if there’s one thing I know about women, it’s that they get super wet when you treat them as a variable in a formula.

Find the hidden rules.

In gameplay, it’s what you know that others don’t that really matters.

- Me, later in this section

The first article of this newsletter was called How to Win Games: Find the Hidden Rules. What I call “hidden rules” are basically the unstated mechanics of gameplay that dictate success. Sometimes, you can reverse-engineer these by thinking about what “winning” means, then working backwards from success to eliminate actions that don’t increase your win probability.

A simple example is that underdogs should increase variance, while favorites should minimize it. An NFL team down 14 points with 10 minutes to play needs things to get chaotic, whereas the favorite wants no volatility. If you’re an underdog in a video game with an opponent, it might make sense to choose an unusual character with which your opponent isn’t familiar, even if you’re new to using that character.

A big mistake I see is making assumptions about what increases win probability, then extending those throughout the entirety of the game. For example, winning a football game is almost always one of point-maximization, but not always; one of the weakest areas of in-game strategy right now is end-of-half clock management, with teams seemingly too focused on scoring points and not enough on point differential, i.e. don’t give your opponent another possession with meaningful time on the clock.

In DFS, the big “hidden rule” I discovered was that the game actually isn’t about scoring as many points as possible, but rather winning with as few points as possible, i.e. where can I unlock points others aren’t and benefit when they’re doing poorly as a whole?

In the game of Wii Sports Resort Golf, it’s easy to make the assumption that the fastest time always equates to the fewest strokes, but that’s not the case. As Chris mentioned in his email, players learned they could tank the first hole to gain a more favorable setup for subsequent holes, which more than made up for the initial time lost.

On one of the later holes, there’s a lake right next to the tee box. One of the top players eventually figured out if you drive the ball straight into the lake and keep hitting it directly into the water, you’d hit the max strokes faster than if you just played the hole normally.

In both cases, astute players found new solutions by asking “What are ways I can lower my time by actually taking more strokes?”

The reason this works—the foundation for hidden rules—is that you’re not going to benefit from something if everyone else is doing it. Few players are specifically trying to search for areas in which more strokes is better, and so if you’re the first to uncover one of these hidden edges, the rewards are yours alone.

Lots of times, this means identifying temporary “losses” that act as a slingshot to higher future win probability, like tanking the first hole, going out of the way in Fun Run, or trying for winners in racquetball when you’re not yet super-skilled.

The key is to decipher what it is you’re actually optimizing for, then look for the few times that the conventional approach has faulty assumptions that makes it sub-optimal.

In gameplay, it’s what you know that others don’t that really matters.

Question everything.

A contrarian isn’t one who always objects. That’s a conformist of a different sort. A contrarian reasons independently, from the ground up, and resists pressure to conform.

– Naval

One thing I find interesting in watching the speedrunning videos is that even though it seems like the new records are unbreakable, they continually get lower and lower over time. Even though the differences in time might seem small, the strategies used by the end are often fundamentally different than those in the beginning.

Super Mario Bros. 2 is a good example of this progression.

There’s one level in one of the games in which everyone previously used Luigi because there’s a crucial point at which you can save a lot of time by quickly jumping up. In an ideal world, the players would use Toad, who runs the fastest when he’s holding an item over his head. However, it was accepted that Toad was not useful in this level because he couldn’t jump high enough to save time over Luigi, until someone came along and figured out a unique way to bounce off of a goomba (edit: idk if it’s actually a goomba? someone told me it isn’t and they aren’t in mario bros 2, but google says they’re in level 4-1. you’d think i’d just change it rather than add this long explanation inside of parentheses. and why am i not capitalizing anything here?) and trick the game into thinking it was still on a flat service, allowing the user to jump again mid-air. This user went on to set a world record by thinking about the ideal scenario—that he could use Toad—and questioning if it were really true that Toad can’t jump as high as Luigi.

Another example of this idea of questioning even basic beliefs comes in Mario Kart—a game with many glitches that allow players to skip large portions of the track.

Two of those basic assumptions you might not ever think to question: you have to go forward to win the race and you should try to stay on the track. There are actually a bunch of situations in which you can go out of bounds strategically to have yourself set back in a more favorable location, and even some in which going backwards at the start of the race—or even at the end of laps—can give you huge edge via securing better items or even tricking the game into thinking you’ve completed a lap you haven’t.

By the way, I’ve never tried any of these, but how sick would it be to sit down with your friends to play Mario Kart and win a race in like 30 seconds?

One way to effectively question your most basic beliefs is to take them to their logical end. I wrote about this in My Extreme Theory of Learning.

Be an outsider.

Whenever possible, I think crosspollinating ideas from other contexts is far, far better than attempting to solve our problems as if no one has ever faced anything similar.

– Sam Hinkie

I’m currently reading a book about psychology and self-image called Psycho-Cybernetics. What’s interesting is that this widely renowned work was written by a plastic surgeon—not a psychologist—after he noticed how patients’ self-respect changed after cosmetic surgeries.

It seems many discoveries, inventions, and insights come from “outsiders,” but why? I think there are two primary reasons. First, “outsiders” don’t have tunnel-vision about the way things “should be.” Everyone views the world through various lenses, and when you get deeply involved in something, it’s very difficult to step back and think about things from a fresh perspective. You inevitably forget the original questions you asked and can have laser-focus that’s perhaps great for small improvements but misses out on the advantages of a beginner’s mindset.

The second reason outsiders can find unique success is that some of the greatest ideas come at the intersection of two seemingly different concepts—what some call “cross-pollination.” I studied philosophy in college, concentrating on Taoism, and was amazed at how many parallels there seemed to be between Eastern philosophy and another passion of mine: theoretical physics. I truly believe an understanding of physics made my reading of Taoism much richer, and vice versa. This isn’t a new concept; if you’re one of the maybe two people reading this sitting at the Eastern philosophy and theoretical physics intersection of interests, check out The Tao of Physics.

To attain a fresh perspective into something familiar, use cross-pollination. Take something else you know or like—anything—and combine it with something else. I used to basically eat, sleep, and breathe DFS, and anything I learned—even if it had nothing to do with sports—I translated into DFS terms. Reading Taleb and applying antifragility to tournaments was the greatest leap of my career. Whether it was playing chess or reading a book about markets or thinking back to psychology classes, I tried to apply lessons I learned or lenses through which one might view the world to something totally unrelated in an effort to generate unique insights. Even when watching speedrunning videos, I find myself taking certain principles or ideas and trying to apply them to my world.

When you’re cross-pollinating ideas—especially those on opposite sides of the brain, like math and art—you’re connecting parts of your mind that normally don’t interact. There’s a lot of really interesting research right now on something that enhances that process—psychedelic drugs—but that’s for another post.

Don’t try to be contrarian.

The most contrarian thing of all is not to oppose the crowd, but to think for yourself.

– Peter Thiel

If there’s one thing to take from this article, it’s that you shouldn’t be afraid to play. Be a kid again. The more unique insights don’t come from following the rules; they come from trying new shit because trying new shit is fun.

When you’re truly child-like in spirit, doing things for the sake of satisfying your curiosities and for no other reason, you’ll naturally find your own way. You’ll be contrarian in the best way possible, rejecting certain widely held beliefs not because they’re widely held, but because they’re false.

Being contrarian shouldn’t be the aim; it should be a byproduct of thinking independently.

Lucky Maverick
Lucky Maverick: The Art and Science of Betting on Yourself
A podcast for independent thinkers