Lucky Maverick
Lucky Maverick: The Art and Science of Betting on Yourself
How to Win a Bet: 6-12-18-24

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]
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 jerks done and you’ll have freedman to help you there

jonathan.bales [12:56 PM]
I don’t drink every day for the last time levi

adam.levitan [12:56 PM]

jonathan.bales [12:56 PM]
if you think 18/24 beers/donuts is easy then idk
and either miles or JOs or both gonna be hard af too
I think I am equipped to do it more than avg person but I think I’m likely to fail

adam.levitan [12:57 PM]
i mean if you take 20 minutes off between each mile it’ll be easy

jonathan.bales [12:57 PM]
even if you remove that, there’s some decent chance I can’t physically do 12 JOs

adam.levitan [12:57 PM]
for sure

jonathan.bales [1:00 PM]
so you’d do 6 to 1 if I ran it straight, no stops at all?
like if I fail then I just start back at 0 miles?
trying to think of how much easier it is to stop and what that equates to in a line if 6 to 1 is fair for that

adam.levitan [1:00 PM]
you’d have to average a 10-minute mile for whole thing.. so if you do 6 miles you have 60 minutes total from start to finish

jonathan.bales [1:01 PM]
there’s almost 0% chance I can complete six miles right now
I’ve literally never run two miles

adam.levitan [1:01 PM]
yeah well if the running isn’t hard i don’t see how you fail really
unless your dick fails you

jonathan.bales [1:02 PM]
he’s good for six easy
he starts to get ornery at seven
idk how you think 18/24 beers/donuts is just a given
that’s so hard
and in conjunction with running and jacking off
will take 5 to 1 my $1k if I can stop once running

adam.levitan [1:06 PM]
if you do the total distance across total time you can stop as many times as you want

jonathan.bales [1:06 PM]
need a break. can’t do six miles in 60 min
will do two segments of three in 30
it is fucking Vegas in summer man it is gonna be literally 120

adam.levitan [1:07 PM]
i can give you 3.5/1 on that, but i’m not happy about it and only doing it for the #content

jonathan.bales [1:08 PM]
like it might not even be safe

adam.levitan [1:08 PM]
don’t be a pussy
death is one of the outcomes, yes

jonathan.bales [1:08 PM]
i’d do 6 to 1 on one hour before 3.5 with a break
outside is just bananas
i won’t be able to breathe

adam.levitan [1:09 PM]
the only way i’ll win is if you fail at the running
so yes, i’d be rooting for “unable to breathe”

jonathan.bales [1:09 PM]
i’ll die for content, it’s fine

adam.levitan [1:10 PM]
yeah i felt like this in 3rd set of frying pan match
you’re so hot you get the chills

jonathan.bales [1:10 PM]
that was fucking denver

adam.levitan [1:10 PM]
it was like 90 but i know.. Vegas is asking for death
that’s how i want to win

jonathan.bales [1:11 PM]
I will do 6 to 1, six miles in 66 minutes

adam.levitan [1:12 PM]

jonathan.bales [1:12 PM]
yeah. and I honestly think this is gonna be a disaster because I can barely finish one mile in under 10…ran the other day

adam.levitan [1:13 PM]
do you have to run during the day?

jonathan.bales [1:14 PM]
what time range is acceptable. clearly I’m running at night if I can

adam.levitan [1:15 PM]
ugh i dunno man.. i don’t want to bet against you in physical activities
nighttime temps in july in vegas average 79 degrees
nice running weather

jonathan.bales [1:15 PM]
the last mile bet I had I ran a half mile
this isn’t lifting

adam.levitan [1:16 PM]
we won’t be able to film your death if you do it at night

jonathan.bales [1:16 PM]
I will do it when light out
idk how I am gonna set it up exactly…need to think about it and what is best in terms of when I start, when I am trying to run, etc
my lean was I’d drink and eat at night, sleep, drink maybe 1 or 2 in morning and run then
I can’t wait too long strategically or else I have to run after eating and drinking too much. there’s just no way

adam.levitan [1:18 PM]
are you allowed to get more action? Like if you can win 5 BTC instead of 2/3 BTC you’ll obv train harder

jonathan.bales [1:18 PM]
I am gonna try obv….I’d be fine reducing our odds if I get more though
like each 10k to win interval I go down a point or something…
I will do whatever you want on that b/c you are right I will actually try if I get a bunch of action…I just doubt I will

adam.levitan [1:20 PM]
OK i’ve wasted enough of this day.. let me think about it

jonathan.bales [1:20 PM]
comee onnnnn gimme something. have to get this booked

adam.levitan [1:21 PM]
freedman verification on jerks?

jonathan.bales [1:21 PM]
I mean obv

adam.levitan [1:21 PM]
no live women in room obv, even for fluffing

jonathan.bales [1:21 PM]
for that I will have a room that is inspected before and I will produce sample each time
yeah no women OR MEN

adam.levitan [1:21 PM]
no cam girls either… no human interaction

jonathan.bales [1:21 PM]
I can watch porn right

adam.levitan [1:21 PM]

jonathan.bales [1:22 PM]
donuts will be standard glazed

adam.levitan [1:22 PM]

jonathan.bales [1:23 PM]
krispy kreme glazed I thought was standard

adam.levitan [1:23 PM]
beers minimum 5% ABV?

jonathan.bales [1:23 PM]
no way….standard miller lite bud light whatever
those are just under 5 arent they?

adam.levitan [1:24 PM]
coors light is like water, think it’s 4

jonathan.bales [1:24 PM]
the other two main ones are 4.2
normal cans of lite beer

adam.levitan [1:25 PM]
no funnels?

jonathan.bales [1:25 PM]
8 oz beers

adam.levitan [1:25 PM]
no shotgunning

jonathan.bales [1:25 PM]
no funnels, drink from can

adam.levitan [1:25 PM]
8oz? you mean 12oz

jonathan.bales [1:26 PM]
yeah I guess
whatever like a normal looking can is
yeah 12
looked it up
6 miles in 66 min, has to be during day, unlimited breaks, 12 oz lite beers, krispy kreme glazed donuts, produce semen 12 times
only other contingency I can think of is vomit

adam.levitan [1:29 PM]
OK i’ll give you 5-1 given the 66 minutes but you have to run between 9am and 6pm… if you sell more than 10k worth of additional potential winnings that goes to 2.5-1
yeah i think vomiting is tough because once you puke you can drink so much more beer

jonathan.bales [1:30 PM]
right. clearly purposely vomiting is out. I see a very high chance of puking while running though and that would stink if I was DQed on that
like what if it’s just a little tiny vomit

adam.levitan [1:30 PM]
are you going to drink any beers at all before running?

jonathan.bales [1:31 PM]
since I am running in the morning presumably, I would like a contingency that I can vomit while running or up to 15 min after, but no other time during the competition. I’d also like to be able to purposely puke at the end once it is clear I finished and am not involuntarily vomiting

adam.levitan [1:32 PM]

jonathan.bales [1:32 PM]
and idk on the beers but it would be like 1-2 and maybe one donut before at max
idk though…might just do nothing and run it right away

adam.levitan [1:32 PM]
you are going to take the full 24 hrs right? so there are 2 mornings, presumably

jonathan.bales [1:33 PM]
there will be just one if I start at night which I think I will

adam.levitan [1:33 PM]
yeah so you’re going to jerk, drink, eat.. go to sleep.. wake up and run and then finish
god this is so easy if you can do the run
we’re basically betting on the run, that’s it

jonathan.bales [1:34 PM]
can you jack off 12 times in a day? no. eat 18 donuts and drink 24 beers or vice versa? no

adam.levitan [1:34 PM]
i can do 6 a day
i can easily do donuts

jonathan.bales [1:34 PM]
I need to do 12 though

adam.levitan [1:34 PM]
i can’t drink the beer but you def can
nah 6 jerks before sleep, 6 jerks across next day

jonathan.bales [1:34 PM]
six jerks before sleep come on

adam.levitan [1:35 PM]
one an hour for six hours?
then sleep for 6 hours

jonathan.bales [1:35 PM]
a good portion of jerks are gonna have to come after drinking
gonna be a real issue
6 to 1 and I cannot drop to 2.5 to 1 because that pretty much means I can’t even get other action
oh I see…I could get 9k more?
6 to 1 and 3 to 1 on that and it is booked

adam.levitan [1:37 PM]
not giving 6-1, it’s too easy
will give 5-1 for the content
but still think it’s a bad bet

jonathan.bales [1:38 PM]
5 to 1 and 68 min

adam.levitan [1:38 PM]
can’t do it.. failing the run is my only shot

jonathan.bales [1:38 PM]
and I want to clarify the vomiting proposal is fine?
5 to 1 then and that’s it
66 min

adam.levitan [1:40 PM]
so you’re saying you can vomit during the run? But you can’t vomit up a bunch of beer and doughnuts

jonathan.bales [1:40 PM]
yes that is correct…I don’t want to be DQed running in that heat and puking but the spirit isn’t to be able to puke up a bunch of beer and donuts
I do want to be able to puke once I finish, however
why don’t we do 2 beer and 2 donut max pre-running
although I almost certainly won’t be eating two donuts for sure

adam.levitan [1:42 PM]
ok that’s fine.. 2 beers and 2 donut max within 2 hrs of run
then you can puke.. but if you do complete the run, you can’t puke again rest of day

jonathan.bales [1:45 PM]
six miles in 66 minutes, unlimited breaks and able to puke up no more than two donuts and two beers from within two-hour window if I do happen to vomit during the run or within 15 minutes of it. otherwise no vomit until last task completed. 12 jackoffs that are produced in a semen-free room. 18/24 beers/donuts. 12 oz lite beers and standard glazed krispy kreme donuts. 5 to 1 on $1k and goes to 3 to 1 if I get more than $10k of additional to-win action.

adam.levitan [1:45 PM]
ugh fine.. it’s booked just for the lulz

jonathan.bales [1:46 PM]

And that, my friends, is the art of the negotiation. If you want to read real advice on negotiating, I highly recommend Never Split the Difference by Chris Voss.

What’s interesting about this besides Levitan’s completely serious mentions of a “semen-free room” is that both he and I know the importance of finding edges, so haggling over seemingly minor details in the rules was quite critical for both of us. Each rule change in my favor might increase my win probability just a few percentage points, but unlocking those edges multiple times and over a continual basis is the difference between long-term winners and losers.

When negotiating anything, identify areas that are more important than the other party realizes (what you want to get) and those that are less vital than they understand (what you want to give up). When it comes to salary negotiations, for example, most people value guarantees, so you can typically trade in steady income for future upside. Perhaps you can work for $10,000 less, but add in a $30,000 bonus if you meet certain criteria, such as a specific sales threshold. This is no risk to the company, since you’d presumably be generating more than $30,000 in revenue for them in such a deal, but increases the EV of your contract, assuming you have greater than a 33% chance of reaching the bonus.

You can calculate the EV in this example to determine what the contract is “worth” to you. If you believe you actually have a 75% chance to reach the bonus, the EV would be (Base Salary - $10,000) + ($30,000 * 0.75) = Base Salary + $12,500. Trading in a sure thing for properly calculated upside (and downside) is one of the easiest ways to unlock EV, and in this case, if you’re willing to take on the risk, you’d make an additional $12,500 per year, on average.

Also, look for things that are more important to one side or the other. Comparing apples to apples isn’t really a great way to unlock EV without an information asymmetry, and continually operating in an effort to produce one-sided contracts is not only unethical, it’s also stupid long-term (and becoming more difficult by the day). I liked this recent tweet thread from Taylor Caby about the importance of negotiation integrity:

The best way to still “win” a negotiation is by finding the areas more important to one side or the other, then “trade” a higher quantity of things you deem of little importance for just one very important thing to you, making it appear as though you’re giving up more when the overall value is in your favor.

How I Planned for the Bet

As I discussed in How to Win Games, one highly effective tactic I’ve found to aid in deciding upon an approach to gameplay is to start at the end, as if you’re already won. From that post:

One way to get started on the right track is to work backwards. If you’re going to win a specific game, what sorts of things need to happen? What does the path to success look like? If you put a little thought into possible end-games, you can sometimes reverse-engineer a formidable plan-of-attack by working within the rules to eliminate potential scenarios that don’t lead to favorable outcomes for you.

This is one strategy employed by the chess prodigy Josh Waitzkin—the subject of the movie Searching for Bobby Fischer—that he discussed in his book The Art of Learning, which I highly recommend. Whereas most chess players approach the game sequentially, learning their opening moves and then progressing into the mid-game, Waitzkin learned how to maximize his odds of winning by starting with end-game scenarios, often with just three pieces left on the board. In doing this, he was able to work backwards from success to cultivate more apt early- and mid-games.

The biggest strides I made in DFS were when I stopped asking “How can I score as many points as possible?” and instead asked “How can I win with the fewest possible points?” and then reverse-engineered how to accomplish the latter by removing scenarios (and lineups) in which I might be likely to score a lot of points but, because of the construction of the lineup, not very likely to win.

As it relates to this bet, rather than trying to formulate a game plan from start to finish, which is how so many go about solving problems, I tried to think about the ways in which I might lose, then do what I could to eliminate those scenarios or reduce their likelihood of occurrence.

One way I could lose was of course to vomit during a period not designated for puking. I have a very strong stomach, so this was the least concerning issue for me. Nonetheless, I’ve also never drank so much beer and eaten so many donuts, let alone combined them, so I wanted to pace myself early so I could gauge my body’s reaction and adjust. I also chose to go with 24 beers and 18 donuts, rather than the inverse, because I figured I can quickly chug a bunch of beers at the 23-hour mark, if needed, whereas if I’m feeling sick, being forced to eat a lot of donuts could be disastrous.

I chose Miller Lite as my beer since it has the lowest alcohol content of any of the main lite beers, which I was hoping might aid in another area in which I could fail: masturbating to completion into a napkin 12 times and having it confirmed by a grown man in a hazmat suit.

You see this shit?

That’s a lot of pressure for anyone, let alone someone expected to get drunk. In addition to low-alcohol beer, I figured a graduated approach to supplementary material for the jack-offs might be optimal, working as long as possible with just my mind before moving to photos, normal videos, and then the hardcore stuff I will take to my grave.

Okay so we have 24 beers, 18 donuts, 12 jack-offs, and six miles, with an initial plan to just start furiously masturbating with a sort of tiered approach while pacing my food and beverage consumption.

Then we had the miles, outdoor in Vegas during the day in summer. There was really no way around this one; I had to train like crazy. I could barely finish a mile when I started, and by the end just a few weeks later, I was at something like a 7:20 pace for four miles. I never actually ran six straight miles while training; it’s very hard and boring! My plan was never to pace this out. I wanted to just not completely burn out, but get off to such a good start in the first 3-4 miles that I could really coast after that. That was really for mental reasons.

Another really big problem, though, was the heat. If you look up the difference in running times based on temperature, extreme heat is a disaster. One way I tried to compensate for this was training in as much clothing as possible.

I have these photos because I had another fitness prop bet with Levitan and Peter Jennings that involved working out X times per week, so we’d send each other sweaty photos of ourselves as proof which is completely normal adult behavior imo.

I researched various neighborhoods in Vegas and noticed it’s typically a few degrees colder and often has more cloud cover in certain areas by the mountains, so we drove 30 minutes to a track around there to complete the miles. And given that I had to run between 9am and 6pm, there was really no choice but to start them as early as possible…which I did, and it was still 105 degrees.

I could have chosen to begin the entire bet at 9am, but I figured it would make sense to break up the other tasks with some rest between. Thus, I thought it made sense to start in the evening, get through as many of the other three tasks as possible, wake up and have a beer/donut or two, run the miles, then come home to hang with the boys and just chill, drink some brews, eat some donuts, and masturbate together.

Wait what?

The Results

Like I said, I ended up winning the bet. Although I tried to pace myself, I began with an unsustainable rate of beers and donuts, forcing them down because “this seems easy” until the combination of alcohol, carbonation, and sugar made me violently ill with explosive diarrhea. Everyone has a plan until they get punched in the large intestine.

Things were looking bleak when my beer consumption began to affect my performance in other areas. When you’re drinking that many beers and eating that many donuts in such a short span, I’m telling you, it’s hard man. Actually, it’s the opposite of hard, which is the problem.

Another issue I didn’t envision was the mental challenge of masturbating feet away from a group of like 10 dudes. I was alone in my room, but it’s a little difficult to climax when you hear Levitan’s nasal-y laugh every 30 seconds. Masturbations 3 and 4 were some of the more challenging of my life, no doubt about it.

So I took a break to restore normal blood flow and reset my mind before roaring back with an astonishing string of masturbations—11 in the first night, as a matter of fact. I was on such a roll here I stayed up a lot later than I planned. Once my stomach settled, I was able to really hammer through the beers and donuts without even getting buzzed. I didn’t stick to my plan because things were going so well. Luckily, our semen collector stayed up late and was able to hang out (and verify some samples). I called him one time in the middle of the night to get out of bed and come look at my napkin, but otherwise he was right there by my side, figuratively speaking.

The next morning, I crushed the six-mile run.

Again, there wasn’t really any way to skirt around it; I had trained like crazy to be able to do this and once I did, it was game over.

We went back to the house and with maybe eight hours or to go, I was feeling quite sick but it was clear I was going to complete the challenge. I had just a few beers and donuts left, plus one celebratory J.O. I was planning for the end.

Levitan offered me a buyout as I was nearing the finish line—mainly because he wanted to go to a WNBA game and didn’t want to be forced to stick around to watch this mayhem—and I took it, with the condition I had to play him in racquetball for money the next day.

In terms of pure EV, the buyout wasn’t in my favor since I’d say I had maybe a 99.5% chance to complete the challenge (and he bought out for like 90% or something). But it was worth it just in terms of not needing to force-feed another Krispy Kreme down my throat while yanking it. The best part is I upset Levitan in racquetball, taking him for an additional $1k.

Final Points

So what’s the moral of all this? There’s no moral. The whole thing was a shitshow. I mean think about it, really.

But I’ll say this…

First, this bet was actually a fitness prop for me. I was trying to get in shape, and the reality is I trained like crazy and really improved my fitness. Even if the bet were slightly -EV for me in terms of money, it would still be very valuable overall to help me get in shape. Prop bets with friends are a wonderful motivator.

Second, if you want to win games, a good place to start is with the rules. Know the stated rules, inside and out. Know their implications. Think about your edges working within the confines of the game. Consider the ramifications of the rules and gameplay and how they lead to “hidden” rules you can focus energy on to maximize win probability.

Then, formulate a plan of attack by starting with success. Envision what it means for you to win, and how you get there. Eliminate as many scenarios as possible that don’t lead to that success. If you’re an underdog in a game, for example, focus on removing all low-variance outcomes in which your chances of winning are minimal. Don’t start from the beginning; start at the end, assume you won, and move backwards.

And lastly, this entire thing was actually just a long con to market PK Safety—the leader in hazmat suits, safety gloves, and other workwear.

PK Safety: Your worker safety specialists.

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