Dream BIG 🍀

One Big, Big Idea

The Case (And Chase) for Asymmetric Upside

Let’s start small - In everyday life, there are countless choices you can make on a daily basis that could lead to an asymmetric outcome. Taking up yoga can have a compounding benefit on your physical and mental health. Reading a timeless book can completely reshape your outlook (and in turn maybe some of those around you.) Bringing substantial value via a cold email or DM can change the entire trajectory of your life and career! Notice that we left out doom-scrolling Instagram and watching ‘Parks and Rec’ for the 14th fucking time.

Fair, but, what about $$? Oh so you’re looking to make a few shekels in your spare time, too? You’ve come to the right place, friend. But first let’s pause for a brief segue.

In case you’re not a fan of obscure gambling podcasts…

The OG sports betting legend himself Haralabos Voulgaris joined fellow GOAT Spanky on his podcast recently to discuss his illustrious NBA (and CFL!) betting career. We’ll get into some other takeaways from this nugget-filled episode shortly, but the biggest thing to remember is that Bob DID THE WORK. Yes he is a brilliantly smart guy, yes he was born into a situation that allowed to get a jumpstart in this unique field, but he absolutely earned his way to the top of the heap. In other words - THERE ARE NO SHORTCUTS. 

Identify something that you can really go deep on because outsized rewards don’t come without a requisite amount of research behind them. You have to study, you have to model, you have to read/listen, and you have to do a ton of it. Because of this, finding the right outlet where even this aspect of the process feels like a game to you is crucial.

Have an edge now? Fantastic. Prepare to push that sucker to the absolute limit. Bob says that in the early days - he could consistently have up to half of his bankroll in play at any one time, and his breakthrough moment was betting the Lakers to win the 2001 title outright. (Which, aside from the AI step-over moment, was an absolute demolition job.) The lesson here is that you want to put in enough volume that you allow your edge to compound over time and maximize your returns. E.g. don’t send 5 cold emails - send 5 every day for a month and see where that gets you. 

There is now a HUGE crossover between tournament poker players, DFS players, and avid crypto/NFT practitioners. All three avenues allow you to enter many tournaments, lineups, and projects at a relatively low price point with the constant possibility of an outsized payoff. 

(Bob himself actually fits fairly well into this venn diagram.)

That being said…

Give yourself a long enough time horizon to strike big. As anyone who has actually put some of these concepts into action knows - variance can be a fickle, fickle beast. It is imperative that you’re maintaining a big enough store of capital to sustain the inevitable swings - and not just YOLO’ing into every opportunity that presents itself. On his recent podcast appearance with Tim Ferris - Morgan Housel noted that the key to so many successes in life is simply allowing yourself to stay in the game. Avoid overextending yourself, completely eliminate any potential risk of ruin, and you set yourself up for the greatest chance of a positive fat-tail event. 

All that is to say, there is truly no such thing as an overnight success. If you’re looking for a get rich (or successful) quick scheme - they do not exist - and you will probably get burned. The only sure-fire way to a chance at an asymmetric outcome - is to give yourself a long enough runway to see it into fruition. This is far, far easier in theory than it is in practice. In the moment - the ups and downs can be fucking brutal. There is just no way around it. Michael Batnick loves to reference this on one of our favorite podcasts “Animal Spirits” when listeners ask them about using leveraged ETFs. In his words he basically says that everyone thinks they can handle a 50% drawdown until they actually experience it and your chest feels like it’s going to cave in.

This is where taking the long view becomes vital. When you zoom out and realize that the choppiness of any given day, week, or month is relatively insignificant in the grand scheme - things become just a tad easier. David Frankel of Founder Collective just wrote a wonderful piece on this as it relates to startups and entrepreneurship. The hard times are undeniably hard, but exhibiting patience can often lead to an astronomical payoff somewhere down the line. 

You know what else helps?

Just don’t be a dick! Seriously. Back to Bob for a moment. He mentions in his interview that simply being a decent guy throughout his career was one of the most vital yet overlooked aspects to his success. He was able to integrate himself into the poker scene seamlessly - leading to connections that would be vital to his operation as it grew bigger and bigger in the future.

There’s not too much to add here - other than just aiming to be a halfway decent person to everyone you cross paths with should be common sense - and it can have an undeniable impact on your life and career. Everyone you meet has the potential to help you and introduce you to further connections somewhere down the line, and all it takes is one negative interaction or first impression to close all of those future doors for good. Your choice.

The Bottom Line: None of this information is particularly groundbreaking or contrarian (Naval, Jonathan Bales and Nassim Taleb are all great additional reading) - but executing and having enough conviction to stay the course during the most volatile periods will be the true test. Just remember to follow these steps:

• Do enough research up front to give yourself a discernible edge on the field.

• Put enough resources towards your new venture to truly maximize that edge.

• Give yourself a long enough time horizon to allow your edge to compound.

• Always remember to be a good person along the way. You never know what people are going through and the doors they might be able to open for you down the line.

What Else We're

Reading

'Fooled by Randomness' - This seminal work from the maestro Taleb serves as a perfect primer for many of the concepts discussed above. Give it a shot and prepare to have your entire mindset shifted.

Watching

'The Restless Billionaire' - However you want to view him - Carl Icahn went from poker playing teenager to one of the most powerful men in business. This wildly entertaining new HBO doc spans his early life through some of his most iconic deals.

Listening To

'Be Better Bettors' - Mobsters, celebrities, and piles of cash - Haralabos' story has all the makings of a great Hollywood movie. Until the inevitable adaptation however, just sit back and enjoy this incredible interview.  

One Final Thought

Until next time! Have a great week.

- G.T.