30 Years of Wall Street OG: How Horse Racing, Poker, and Investment Legends Inspired My Bitcoin Journey

A seasoned Wall Street investor, combining the odds mindset taught by his father at the racetrack with the wisdom of investment masters such as Munger and Druckenmiller, analyzes the current severely undervalued investment opportunity in Bitcoin and how to make wise decisions under uncertainty using probabilistic thinking. This article is adapted, compiled, and written by Foresight News based on an original piece by Jordi Visser. (Background: Michael Saylor: Major banks like J.P. Morgan Chase, Citibank, BNY Mellon, and Wells Fargo are beginning to offer “Bitcoin-backed loans”) (Additional context: Standard Chartered cuts Bitcoin forecast! The 2025 end target slashed to $100,000, and it will take another five years to reach $500,000 BTC) At age five, my father took me to Monticello Raceway in upstate New York for the first time. He handed me a racing guide and began teaching me how to interpret the data: past performances, jockey records, track conditions. Those numbers and symbols felt like a mysterious language to me. Over the years, we often went there. That racecourse became his “classroom.” He never asked me to “find the winner,” but always guided me to focus on another question: Is there betting value in this race? Whenever I completed a odds prediction for a race, he would ask about the basis of my assessment. Then, he would draw on his experience to point out what I missed or what dimensions I should have explored further. He taught me:

• To identify patterns in race results
• To balance the influence of different factors
• To set odds that are realistic and not based on wishful thinking
• Most importantly, to continuously reassess odds as new information emerges

Unintentionally, he trained me to use Bayesian methods to predict future probabilities. I have applied this skill in every major decision in my life, especially during my over 30 years on Wall Street. Today, this analytical framework has led me to focus on the most mispriced betting target in my career: Bitcoin. When I analyze Bitcoin using the odds method my father taught me, I see an asset with a 3:1 odds. Yet, many of the smartest people I know assign it a 100:1 odds, or even consider it worthless. This valuation discrepancy is not only huge but also presents a rare and excellent opportunity—one rarely encountered in a professional career.

Learning to Bet on the Future The method my father taught me is rigorous, not casual. Before setting odds for any horse, I must do my homework. I treat researching the race guide as a success course:

• Past performances under different track conditions
• Jockeys specialized for certain scenarios
• Changes in the horse’s class, equipment, and race rhythm predictions
• Bloodlines and training routines

He even taught me to stay skeptical, not to trust human factors too easily. Not every horse gives its best; some are “holding back” for future races, and some trainers have fixed tactical routines. All these factors must be considered.

Moving to the actual betting phase, I learned to observe the timing of smart money entering the market and the fluctuations in odds in the final minutes before the race. But the core rule is simple: I must first write down my predicted odds before looking at the betting display. This isn’t about guessing blindly; it’s about building a solid logical basis for my judgment. For example, why should I believe this horse has a 20% chance to win (5:1 odds), rather than 10% (10:1) or 5% (20:1)? Only after completing these preparations and clearly explaining my reasoning will he allow me, as a novice, to look at the public betting trends.

And at this point, a wonderful opportunity appears. Sometimes, I predict a 5:1 odds for a horse, but on the betting screen, the actual odds are 20:1. This advantage doesn’t come from being smarter than others but from the fact that most odds setters simply haven’t done their homework thoroughly. The greatest opportunity lies in their oversight.

He also repeatedly emphasized another key principle: if the odds already fully reflect the true value of a race, then it’s best to skip betting altogether. “There’s always another race.” Choosing to stay on the sidelines when you lack an edge is one of the hardest disciplines to master in the market and a lesson many investors have yet to learn.

Thinking in Terms of Betting Years later, I realized that the method my father taught me is actually a professional approach developed over decades by poker players and decision theorists. Annie Duke’s book Thinking in Bets: Making Smarter Decisions When You Don’t Have All the Facts provided a theoretical framework for the experience I gained at the racecourse. Her core insight is simple yet profound:

All decisions are bets on an uncertain future; the quality of decision-making should be judged separately from the outcome.

You might make a very wise decision and still lose. Even if the valuation is reasonable, a horse with 5:1 odds has an 80% chance of losing the race. What truly matters is:

• Is the decision process rigorous?
• Are the odds set based on solid reasoning?
• Do I have an edge when placing the bet?

A few years ago, I had a face-to-face conversation with Annie, telling her that her book aligns perfectly with my father’s racing philosophy. I’ve always known this logic has helped my investments and even shaped my thinking about health and happiness.

What we discussed more was her background in psychology rather than poker or her book, because all these are fundamentally connected. This framework isn’t just for poker or investing but applies to decision-making in all fields under incomplete information.

The key takeaway is consistent: we live in a world of imperfect information. Learning to make decisions using probabilistic thinking and separating the decision process from the results are essential for long-term progress.

Munger: The Market Is Like a Race Track Charlie Munger once presented a view that connects all logic: the stock market is essentially a betting pool system. In a betting pool, prices aren’t determined by some intrinsic objective value but by collective betting behaviors of all participants. The odds on the betting screen don’t tell you how much a horse is worth but what proportion of the total betting pool is wagered on each horse. The same logic applies to how markets operate. Stock prices, bond yields, and Bitcoin valuations are not dictated by TV commentators or social media narratives but by the actual flow of capital.

When I view Bitcoin from this perspective, the real odds are never the statements of a few wealthy individuals on CNBC but are reflected in the relative sizes of different asset pools:

• Bitcoin versus fiat currencies
• Bitcoin versus gold
• Bitcoin versus the total wealth of households worldwide

These ratios and relative performance trends truly reveal the beliefs of collective bettors, independent of public statements.

Interestingly, if someone claims Bitcoin is worthless, from the perspective of betting pools, they are not entirely wrong. Despite Bitcoin’s impressive performance, growing user base, and a decade of global monetary experiments and fiat devaluation, Bitcoin’s size remains small. Compared to traditional stores of value, capital allocated to Bitcoin is minuscule.

From a betting pool perspective, the public’s actions show their attitude: they are hardly betting on Bitcoin. And this is precisely where my odds assessment begins.

The Power of Jones, Druckenmiller, and Positioning The greatest macro traders of all time—Paul Tudor Jones and Stanley Druckenmiller—share a core principle often overlooked by most investors: position sizing can be more important than fundamentals. Jones once said, “The crowd is always one step behind.” Druckenmiller’s sharper insight: “Valuations can’t tell you when to enter; your position size reveals all the risks.” When everyone is on the same side of a trade, marginal buyers disappear. The market…