Many of you know I made a bet that Donald Trump would become our president – I wrote about it at 4for4 a year ago, although the bet was made months before that – so I just wanted to talk about why I made that bet, which was centered primarily around one core principle.

Before getting into it, a few disclaimers:

– The bet was in no way a reflection of how I felt about who would be best for our country. It was simply the result of my belief that the reasoning behind the “Trump could never win” idea was flawed.

– I’m writing this primarily as a way to think about risk and uncertainty – not as a political stance. If it were possible to have less than zero interest in a Twitter debate having anything to do with this election, that’s where I would be. DON’T @ ME.

– I collected on the bet after the RNC when Trump moved to near a coin flip in many models (I took less than 50% of the possible payout). Even though that was -EV for me to do if I believed Trump was 50% to win, I thought it was a smart decision based on what I wrote at the link I posted above. I would have hedged by betting on Clinton had I not been able to get out of the bet.

– I’m not claiming to be some political savant; I know so little about politics it’s actually kind of sad. This had literally nothing to do with my understanding of the political landscape and everything to do with Trump’s uniqueness/volatility as a candidate and – I hate to say this – how bad I believe many people are at making decisions.

– The bet was $500 at 150-to-1 to win $75,000. When I made the bet, the implied odds were that Trump had a 0.67% chance to become president, whereas I thought it was around 10% at the time. So I actually didn’t think he would become the president at all – just that it was far from outside the range of outcomes.

With that said, the reason I thought Trump could win is a concept I’ve talked about many times in the past: antifragility.

 

Antifragility

Basically, I believed Trump was unique among political candidates in that, because no one really viewed him as a politician and everyone was already pretty familiar with his outrageous personality, he didn’t really have too much downside in terms of the negative things that could be said about him. And not only that, but I thought he’d be able to benefit from the idea that “any publicity is good publicity.”

This concept of antifragility was coined by Taleb, and it’s basically that certain things (the antifragile) can gain from disorder and chaos. From an earlier post of mine:

“Taleb classifies things into one of three categories: fragile, robust, and antifragile. A mirror is fragile; it is harmed by fragility and doesn’t deal well with stressors. A diamond is an example of something that’s robust, or resilient. It doesn’t benefit from chaos—a diamond doesn’t get better when you drop it, for example—but it isn’t hurt, either. It’s basically indifferent to uncertainty and chaos.

For so long, these two labels were all we had. The opposite of something that’s harmed by volatility is something that isn’t harmed by volatility, right? Well, Taleb opened our eyes to antifragility. Evolution is antifragile. Not only is it not hurt by chaos—by errors—but it thrives and exists because of randomness.”

Or, you could just read what Taleb has to say about antifragility since, you know, it’s his idea:

“Some things benefit from shocks: they thrive and grow when exposed to volatility, randomness, disorder, and stressors and love adventure, risk, and uncertainty. Yet, in spite of the ubiquity of the phenomenon, there is no word for the exact opposite of fragile. Let us call it antifragile.

Antifragility is beyond resilience or robustness. The resilient resists shocks and stays the same; the antifragile gets better. This property is behind everything that has changed with time: evolution, culture, ideas, revolutions, political systems, technological innovation, cultural and economic success, corporate survival, good recipes (say, chicken soup or steak tartare with a drop of cognac), the rise of cities, cultures, legal systems, equatorial forests, bacterial resistance. Even our own existence as a species on this planet. And antifragility determines the boundary between what is living and organic (or complex), say, the human body, and what is inert, say, a physical object like the stapler on your desk.

The antifragile loves randomness and uncertainty, which also means – crucially – a love of errors, a certain class of errors. Antifragility has a singular property of allowing us to deal with the unknown, to do things without understanding them — and do them well. Let me be more aggressive: we are largely better at doing than we are at thinking, thanks to antifragility. I’d rather be dumb and antifragile than extremely smart and fragile, any time.”

That last sentence is more or less how I view Trump and Clinton. Trump is dumb and antifragile. I don’t believe he’s a sharp person at all, but he not only had nothing to lose in his campaign, but he benefited tremendously – A TREMENDOUS BENEFIT, THE BEST BENEFIT, IT’S GONNA BE A GREAT BENEFIT, BELIEVE ME – from basically anything that was said about him. He gained from volatility in a way a traditional candidate probably couldn’t have. Think about all the publicity he received for just doing dumb shit.

Clinton is the opposite of Trump: smart and fragile. Regardless of your stance on her emails, there’s little doubt the entire ordeal hurt her. Compare that to Trump, who seemed to benefit from saying and doing some, er, unconventional things (at least unconventional for a presidential candidate). Different types of people reacted differently to each one’s issues, but I believe the expectations of each were a serious factor in their fragility; Clinton was supposed to speak and act a certain way and could really only be harmed when things didn’t go according to plan, whereas Trump didn’t have that expectation – he had less downside that could result from negative stuff coming out about him – and could only benefit from chaos.

For the record, I don’t think being dumb is a prerequisite for antifragility – someone like Mark Cuban has some antifragile qualities without being a dummy – but I do believe the way campaigns will be run in the future will look a whole lot different based on this race.

So Trump was in a much better position to be the beneficiary of uncertainty, which was of course what happened in regards to the election results being unaligned with polling. This is of course an idea very related to antifragility, but I think it’s yet another example of people generally being much too confident in their beliefs. This is why antifragility can lead to huge payoffs, as it does all the time in daily fantasy sports, because people severely underestimate the odds they’re just wrong. Or, perhaps more accurately, even when people are accurate in their probabilistic assessments, there’s still a severe systemic bias toward favoring what should happen and not preparing for the inevitable “rare” event.

In regards to the election, almost every forecast had Clinton winning handily, many with well over 90% certainty. Nate Silver warned against that overconfidence, and although his model predicted a Clinton victory, he was much lower on Clinton than almost everyone else, including betting markets. As he wrote:

“In our national polling average, about 12 percent of voters are either undecided or say they’ll vote for a third-party candidate. While this figure has declined over the past few weeks, it’s still much higher than in recent elections. Just 3 percent of voters were undecided at the end of the 2012 race, for example. As ought to be fairly intuitive, undecided voters make for a more uncertain outcome.”

I possess about 10% of the brainpower of Silver, but my fundamental logic in initially betting on Trump was:

1) This guy is unconventional and past data won’t apply to him as much as other candidates, thus creating more uncertainty in the results;

2) The way people already think about Trump sets up well for him to be the one to benefit from that uncertainty if things get weird.

And I believe that’s probably more or less what happened; he wasn’t harmed from the attacks on him – he even benefited in many cases – and the uncertainty we saw with undecided voters, many of whom were maybe “decided” but didn’t want to admit voting for Trump, worked in his favor.

 

Final Thought

I mostly just got lucky with the bet – the word ‘lucky’ seems off, but you get the idea – although the core idea that I think is most actionable is to identify situations where others are overconfident and fragile and put yourself in a position to be the beneficiary if things don’t go their way. That was my approach here, as it is in DFS, but it’s very applicable to many facets of life.

Most upside comes in embracing randomness and wisely taking on risk when it’s clear others are underestimating the probability of weird shit happening.

The past month or two has been super chaotic for me. I’ve actually gotten stressed out a couple times, which almost never happens. For whatever reason, I just don’t really get anxiety – which hasn’t always been the case, but has changed I think since I started playing DFS – but preparing for NFL this season was more intense than ever by a significant multiple.

In addition to just normal preseason prep as a player – which is honestly now one of my lowest priorities – I wrote another DFS book and of course spent the majority of my attention on FantasyLabs. What I do day-to-day has changed pretty rapidly over the past couple years, but the shift from truly working for myself and pretty much doing whatever I wanted to being the President/CEO of a company some might say is serious enough that I should stop drawing dicks on all my content – a company with a billionaire investor – has been a real challenge for me, and one I’m continually trying to embrace.

FantasyLabs now has like 14 employees or something, including the founders. It might be 13, it might be 15, I don’t know. It’s enough that I need to work with other people all day, every day. As you might already know from reading my books or other content, the closest I came to holding a real job in the past is a toss-up between trying to become a famous artist and doing street magic. Fucking street magic.

Anyway, everyone at Labs works incredibly hard – it’s unreal – and I love that. In terms of leading that charge, I think I pretty much suck right now other than building the right team – our collection of natural talent and work ethic is bananas – and having a decent sense of cool things we can build to help DFS players and just working non-stop to do that. And really, most of the value there has come from the developers, who are the best I’ve ever seen in action.

So with everyone grinding so much, there’s a risk of burnout and it begs the question of whether or not it’s a positive to have balance in life. I talked to Joey Ingram a lot about this both on and off of his podcast. I think most people would say, “Of course balance is good you jackass,” but I’m going to respectfully disagree. I don’t think balance – at least as we traditionally think about it – is actually a good thing at all, at least not for me.

Why Life Balance Sucks

A lot of times when I go on podcasts or whatever, people ask me how much I work. The truth is I don’t really know because I can’t realistically separate what’s “work” and what’s not. And in reality, I have no idea what my job even is. Am I a writer? A DFS player? An entrepreneur? Is the goal of my job just to make money? To provide value to people? To have fun?

Let’s just pick one and say my job is to make money. And we can take it a step further and say “make money online” since doing it out there in that scary real world doesn’t seem that great. Within that job description, there are certain tasks that seem like obvious work to me: taxes, payroll stuff, hiring/firing people, answering emails, etc.

But then there’s other stuff that’s sort of a gray area, like playing DFS, going to events that are mostly fun but also sort of work, being part of stories like this one that makes me feel like way more of a baller than I am, having dinner with Levitan and talking football, and so on.

And then there’s stuff I think almost everyone would say isn’t work but I still believe is part of what I consider “work.” This includes things like exercising, reading, getting good sleep, and so on. I actually believe these three things in particular are some of the most important things you can do to make your life a whole lot better. Even in terms of “work,” I don’t think there’s any better return on my time than reading – even though it can take up a lot of time and sometimes gets neglected – because even just one amazing book can fundamentally change the way you approach life or business or relationships in an extremely positive way.

Quick aside: one theme of this post is to take a longer view than others and not worry too much about what maximizes the short-term return on your time. Reading a book is certainly -EV for me in terms of making money today, but almost guaranteed to be one of the best uses of my time if the view is, say, the next five years. Similarly, it’s basically never a good decision to work out if you’re trying to maximize your happiness or the return on your time in a given day – exercising sucks ass and each individual workout barely makes a difference – but a commitment to the process of working out has monumental long-term benefits.

I think most might argue, “Well this is your balance,” but I think the difference is you can go to work and then come home and spend time with family or read or exercise or whatever, but they’re generally viewed as very separate activities. This is work, this isn’t. In my opinion, this way of achieving balance isn’t useful and can even be detrimental long-term for reasons I mention below, but primarily because there’s no overarching vision or purpose behind what you’re doing.

When you do something you truly love, everything is work and nothing is work at the same time. Everything you do is done with one singular focus in mind – even if it’s thinking about the most optimal way to eat meals in order to balance health, time, money, etc. so that you can achieve the greatest long-term success in whatever your goal(s) might be, or reading a book about theoretical physics and applying it to whatever field you’re in to try to acquire unique insights, or going for a run so you can rejuvenate and become more efficient in whatever else you want to do – and anything that doesn’t help you reach that one goal isn’t worth your time.

Basically, work/life dichotomy isn’t a thing. Or at least it shouldn’t be. If it is, then I’d argue you’re probably not doing something about which you’re passionate. It doesn’t even need to be work. If your primary goal is to pick up girls and sleep with them or find a girlfriend or whatever you want to do, then dedicate yourself to that. Work out with that in mind. Read books you think will help get girls. Or maybe your goal is to be the best friend you can be, or make more money, or know more about geese than anyone in the world. You know better than anyone what will make you happy, so to me, everything you do should be with tunnel vision in an attempt to do that one thing.

And that one thing can and should change, but at any given moment – and sometimes very long periods of time – everything you do should be aligned with reaching maximum potential as it relates to that single thing.

A lot of this has to do with the idea that a disproportionate amount of reward – whether it’s money, happiness, love, anything – is located in the tails because few people are adventurous enough to wander there. What I mean by that is that, because it’s scary to truly dedicate yourself to one narrow focus at a time, everyone sort of just tries to balance everything all at once – they try to be the best friend, the best husband, the best business person, maintain the best health, and so on – all at once.

I think this fails for two reasons. One is that, practically speaking, you can’t win in, say, business and not dedicate your life to it. Or maybe you can, but it’s very challenging when you’re competing against other people who aren’t trying to achieve the same type of balance.

The second is that you only have so much time and energy to go around and you can’t be great or even good at everything, and I think you can make a case you can really only be truly great at a handful of things in your life – and probably just one at a time. Think about even just one aspect of life, like working out. I’m sure you realize what an insane amount of time goes into working out and eating healthy if your goal is to seriously impact your life and be the best you can be in terms of health, strength, looking good, whatever. I did that for maybe two years – I amassed an incredible amount of knowledge about fitness, anatomy, nutrition, etc. – and it was exhausting as shit to try to implement all those things.

And that was all for one goal, which was basically look good to get girls.

So most people obviously counteract that by not seriously dedicating themselves to working out, but doing it a little to “maintain.” And then the same thing with business; “well I can’t consistently work 14 hours a day, so I need to give up some time here so I can do these other things.” And then the list goes on and on until you end up just not really being good or getting satisfaction out of anything.

In my opinion – and this could very well just be me being a psychopath – you can’t realistically achieve a high level of happiness, mental health, success, wealth, etc. in a bunch of areas at once; you can’t be the best possible friend, the best possible artist, and the best possible bodybuilder you can be, for example, at the same time. And so many people try to juggle everything, it seems, and then end up being shitty or unhappy at all of them. It’s very similar to multi-tasking – which has been proven to be a very inefficient use of time – in which you try to do a bunch of things at once and then end up taking more time and doing a worse job than if you focused on one at a time with breaks in between.

One counterargument might be that not everyone wants or needs to be the best in the world at something, which is true, but I also think it’s true that people get happiness out of a pursuit of something important to them. “The journey is more important than the destination” (or whatever that quote is). People get satisfaction and feel a sense of purpose from achieving their goals. My argument isn’t that you should have this goal or that goal, but just that you should focus mostly on one at a time and do whatever you can to be happy and successful in that one area – not try to balance everything at once.

When you try to achieve balance every single day, you can’t get into a flow state; you can’t give the hyper-focus necessary to really truly accomplish anything at a very high level.

Why Life Balance Doesn’t Suck

So I just wrote a bunch of words about how life balance sucks, but I’m really talking about a traditional type of balance – the kind I think most people think of when they hear ‘life balance’ – through which you have a typical work/non-work life dichotomy. And it doesn’t even need to be work. We could be talking about any single aspect of life, and I think conventional wisdom is that you should be “well-rounded” and have lots of interests and not become obsessed with one specific thing or bettering yourself in only one at a time.

I obviously disagree, but that doesn’t mean balance is bad. I actually think life balance is outstanding and necessary, and I’m really just disagreeing with the optimal way to achieve that balance. Fundamentally, I think it’s a difference in the timeframe through which we’re trying to achieve balance, and my belief is many people want to be balanced in much too short of cycles.

It’s sort of similar to how people who are dieting and watching what they eat try to hit the “optimal” carb/protein/fat ratio every day, or sometimes even every meal. I’ve seen people who want X/Y/Z percentages of macronutrients eat carb-loaded meals at night because they didn’t have “enough” during the day. How does that make any damn sense?

We don’t need to – nor should we – try to be balanced every single day. I don’t think it should be every week, or even every month. It’s likely the optimal “cycle” in terms of hyper-focus on one specific task or goal varies from person to person, but I’m confident it’s much longer than what’s reflected in how people act.

Thus, I want to achieve balance, too, but I think that balance should come over a period of probably months, or perhaps years. If you want to be the best pick-up artist you can be and get girls to like you (btw I typically write as if a guy is reading my stuff because, well, that’s almost always the case given my audience, but obviously everything applies if you are a woman or gay or a turtle or whatever), then you’re going to find way better results by dedicating yourself to that life for 60 consecutive days and learning everything you can possibly learn about picking up girls during that time as opposed to doing it occasionally over the course of a year (even for 60 total days).

I think the results of intense focus and long-term balance compared to short-term balance at all times look something like this…

 

This is the case for a variety of reasons – capitalizing on being in a flow state and thus maximizing efficiency for long intervals being maybe the most important – but I really think this long-term view of balance leads to superior results in basically every area of life. We see it in nature with our bodies, too, with things like carb loading and short, high-intensity training providing superior results to balanced eating and long, low-intensity workouts.

Of course, I’m probably completely wrong and you most likely shouldn’t listen to anything I say. I mean if you have kids, I’m basically telling you to be a good father for one-third of the year for Christ’s sake. But during that time you’ll be a really good dad!

But in all seriousness, I think the main argument against my theory of balance is that it’s pretty selfish and arguably naive in its view of how it affects others, even though I’m a firm believer it will (still) end up maximizing your overall life EV.

Other Stuff

I’m going to try to post here more because it’s therapeutic and, in typical form, I’ll probably do it a bunch at once and then skip months at a time, as I have thus far. But since I don’t really know when I’ll get to post anything about what I’ve been up to recently, here’s a quick rundown.

 

Nashville for Week 1 RotoGrinders/DraftKings party

These parties are always an awesome time. I was in Nashville for five days and ate roughly 3,000 biscuits. One of them was at this place…

Everyone says this is the best place for hot chicken. I’m pretty sure I’m gonna get a ton of shit for this but my official Hattie B’s grade as someone who has now had hot chicken three times and is basically an expert: 6.4/10. It was fine – I’d eat it again – but I had like five things better on this trip alone. One of them was Biscuit Love, which was incredible and definitely the best biscuit sandwich I’ve ever had, which is saying something since I have McDonald’s sausage, egg & cheese sandwiches all the time – most underrated breakfast sandwich in the game, even though each one is a new adventure.

Other things I did in Nashville:

– Had lunch with Cal and Cam from RotoGrinders

– Somehow ended up at a Vanderbilt frat party

– Hung out downtown on Broadway; exhausting trying to keep up with which girls are part of which bachelorette parties

– Hung out with Peter, Justin, and Sean from FantasyLabs; met a lot of other sharp people and talked more with big DFS players like Assani Fisher, KillaB, etc.

– Had a nice sweat with David Johnson in the $300

– Made up a game in the hotel room kicking a pillow up in the air as many times as possible before it hit the ground – I had the record of 15, nbd – until the game ended…

I attempted to put it back together and hide the cracks with a little clever maneuvering. No charge yet.

 

Vegas/TX

Since I can’t set DFS lineups in Nevada, I swung by for a day before NFL started. I actually didn’t know this – and I’m embarrassed I didn’t if it’s true – but someone told me it’s legal to edit your lineups in Las Vegas, but you just can’t enter contests there. So you can enter all your contests in a legal state, then travel to a banned state to actually do the lineups. Can someone confirm this is true? Also, how fucking insane are these laws?

I also was in Texas for a short time a couple weeks ago and got to experience a few firsts. One was a Rangers game…

Pretty cool stadium. Stacked the Rangers (obviously on DraftKings since FanDuel isn’t operating in Texas…again, how fucking insane are these laws?) and they somehow managed to score like 13 runs or something without any of the players I chose doing well.

The other new thing I did in Texas was visit Austin for a weekend. People have always said I would love the city, and I definitely did. I did mostly tourist stuff, like kayak in the river, look for bats, and take pictures of old man asses.

I think there are maybe like five cities in the country I would live, and Austin is now on that list.

And lastly, I attended SummerSlam.

I had never watched WWE up until that night, even on TV, and I can say with a decent level of certainty it’s the weirdest thing I’ve ever seen in my life.

Links to Some Crap

SUCCESS Magazine Story (from this trip to the Playboy Mansion)

Joey Ingram “Poker Life” Podcast

Intro Podcast for Team FantasyLabs

Pro Football Weekly Interview

RotoViz Numbers Game Podcast

These Ridiculous Ongoing Barstool Sports Podcasts (somehow got Levitan to do it)