Fantasy Sports as Preparation for Investing

Investing is the greatest game in the world. All previous games I played were preparation for financial investment—such as collecting baseball cards, fantasy sports, poker, chess, and Monopoly. Investing is the ultimate game because it is a combination of all other games. Investing has the strategic thinking of chess, the research and tracking of fantasy sports, and the monetary stakes of poker—except investing is better than all of them, because it combines those aspects together into one omni-game.

Chess and fantasy sports don’t have as much money, and poker has too much luck and unfairness. Investing is more fair with less luck, and you don’t need to be the best in the world (like chess) to earn money. Investing is accessible to anybody. There’s no ambiguity or subjectivity. The winners and losers are clear. You either made money or you did not.

Investing is an infinite game. There is no end like a chess match, video game, sports season, or poker tournament. That also means the amount you can win is infinite. There is endless novelty involved in investing, as the game parameters are ever-changing. Market dynamics constantly shift, with new technologies being invented and new companies launched each year. To succeed, you must forever be learning and improving your investment strategy.

I used to devote an inordinate amount of time to playing fantasy sports (baseball, basketball, and football)—drafting players and tracking their stats to find hidden value. I’ve been successful in winning many of the fantasy leagues I joined in the past, but the amount of time I spent on fantasy sports (thousands of hours) was probably not worth the monetary prizes (hundreds of dollars). I’ve since retired from fantasy sports and devote more of my time to investing because it’s a better game. It’s just as fun and addictive, but with better financial rewards for your time. (Spending thousands of hours studying stocks has yielded me hundreds of thousands of dollars.)

Though not all those hours spent on fantasy sports were a waste of time. In many ways, fantasy sports was a good preparation for investing. The two “games” are actually quite similar. You need to select certain players (or companies) among a larger group based on their perceived value. You try to find those that are undervalued by others. In both fantasy sports and investing, one of my favorite things to do is find a young “up-and-comer” who could become the “next big thing.” I try to find the rookies in baseball with no track record who might have a breakout season. You could get them at the end of the draft or even undrafted, and they might turn into a first-round talent, such as Mike Trout in 2012 or Julio Rodriguez in 2022. That’s similar to what I do in investing: try to find penny stocks trading under $10 a share, but with the potential to 10x or more (such as Palantir, which I first invested in when it was around $9 a share). Or not necessarily penny stocks, but undervalued companies with massive growth potential. Tesla was trading at about $35 when I first invested (which adjusted for splits would actually be about $4 a share today), but I saw great potential in the future of electric cars (and the visionary leadership of Elon Musk). I’m up about 9,000% since, the best investment of my life (along with Bitcoin).

Fantasy sports is also about finding the veterans who are undervalued or perceived as boring because they do the same thing every year. In baseball, I drafted veteran pitchers like Clayton Kershaw and Zack Greinke at discounts late in their careers when it seemed like they were past their primes, yet they still pitched well and provided good value. In stocks, I invested in Amazon and Google when they were each around $1,000 a share in 2017 (adjusted for splits, that would be about $50 now). At the time, many thought the stocks were too expensive, at or near their peak. But I saw plenty of value still left ahead, which has turned out to be true.

What I love about investing is that there is no single strategy for success. There’s great creativity involved in choosing your strategy, which can be highly mathematical, or more intuitive (as my strategy is). I rely less on charts, numbers, and math, and more on studying the people behind the company and their technology (as most of the companies I invest in are in the tech sector).

I write near-future science fiction, so I’m constantly following the latest science and technology. That’s why I’ve been early on many tech stocks. Though my blind spot was that I mostly focused on the forward-facing consumer brands, rather than the “picks and shovels” players behind the scenes. For instance, OpenAI (the chatbot) versus Nvidia (the GPUs that power that chatbot). I eventually bought Nvidia, but not as early as I could have. Though you don’t need to pick every winner to win.

There are infinite ways to play and win at investing. You can choose your game within the game. You decide what the winning parameters are. Winning doesn’t necessarily mean making the most money in the world or taking the riskiest bets. Winning for you may be a simple strategy that takes less risk and less time commitment (like automatic monthly investments to an index fund), so you can make passive income in the background and spend the rest of your time playing fantasy sports. That is not my current investing game, but to each their own.

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