Winning Gamblers: The Care and Feeding of White Crows

"If you really don't like to gamble, you have a much better chance of winning."  


People often ask me, "How does a person train to become a winning gambler?" "What qualities are needed to win at gambling?" "Are there rules that can help you win?"

These are reasonable questions. Winning gamblers are very, very rare. My own highly speculative subjective estimate is that, in sports betting, about a hundred individuals or teams of people win long term in the United States. I'll explore many of the attributes that separate winning sports bettors from civilians in the months ahead.  Today, however, I'll tackle just a couple of fundamental ideas that I believe can be helpful to both sports bettors and gamblers in general.

First of all, I'll state the obvious. "Gambling" is just a word. The gamut of behaviors and activities that American culture lumps under the umbrella of "gambling" is wide-ranging. Just because a word exists in a culture does not mean that some actual thing neatly and objectively corresponds to that word. If an alien race visited the United States, would it have any compelling reason to label lottery scratch offs and hockey betting with the same word? The fact that so many different behaviors get lumped into the category of "gambling" can create problems for those trying to win. We'll circle back to this in a bit.

"If you really don't like to gamble, you have a much better chance of winning." Yes, I believe that. Here's why.

In American culture, most if not all of the activities that fall under the purview of the word "gambling" have addictive elements. I'm not taking any moral or ethical position on this. I don't really care if 90% or 10% of the activities someone undertakes are addictive. I'm just pointing out that most "gambling" is to some degree addictive for most people. That includes, of course, sports betting.

I'm going to further argue that one cause of the addictive nature is our culture's hyper-commercial emphasis on material resources, income, and the micro-management of both. The culture is saturated with the buying and selling of products and services. Thousands of brand exposures per day literally immerse each person in everything from half-price shakes at Sonic to the latest rebates on half a dozen competing pickup trucks. Elections can be won or lost based on whether the buying powers of families have risen five percent or dropped five percent. Every financial transaction is labeled as significant and something to be analyzed or controlled.

The behaviors under the aegis of "gambling" acquire significance for the individual due to the perceived consequences of winning or losing money and the physiological effects from that winning or losing. The way our culture frames gambling impedes our ability to objectively evaluate whether we know what we're doing. For example, most people who are introduced to gambling think that it is indeed about "winning money" as if "winning money" is some kind of skill. Civilians look at poker tournaments or sports bets and see winning or losing of money as the primary defining components. This is not at all helpful in the pursuit of actually winning at gambling.

Chris "Jesus" Ferguson, the 2000 WSOP Main Event winner, said that he could be beaten, but he couldn't be outplayed. Basically, he was explaining that he has control of the proximate (his play), and that the ultimate (the tournament financial result) is not the most direct measure of his expertise. All gambling activities involve an eventual financial result. Most people who attempt to gamble mistake the end financial result for the task at hand. This is not a useful perspective, but it's the perspective native to our culture. It can be a real albatross around one's neck.

Because individuals who begin gambling always, upon immediate failure, have the option to increase stakes in a Martingale fashion, "winning money" can be achieved again and again at greater and greater bankroll/indebtedness risk. Defining success or failure in the short term by "money won" can therefore be antithetical to achieving real expertise while also being extremely hazardous to one's bankroll. Short term winning or losing is no indication of much of anything. Civilians tend to conflate short term winning with proficiency. This emphasis on short term "money won" is not only an inappropriate way of evaluating expertise, it suckers the person who has won in one type of gambling into thinking that he should be able to apply himself to other types. In part, this error is due to what I mentioned earlier. Many dissimilar activities get lumped under the term "gambling." This serves casinos well.

Here's another reason I think that, in terms of learning to win, a person who dislikes gambling has an advantage over someone who likes it. Simply put, those who dislike the risking of money are less likely to get the addiction bug. People are much more likely to become addicted to winning or losing money than they are to lengthy decision-making processes. Money-as-goal should be secondary, maybe even irrelevant. In sports betting, what's important is that one enjoys the gathering and prioritization of data, relentless shopping for numbers, and timely decision-making. Those are building blocks to winning. The person who devotes himself to process, and each sport has its own particular process, has a chance to win. Gambling on each sport has a markedly different process, and different casino games clearly have enormously different processes. People need to acknowledge that rather than buying into the idea that it's all "gambling" with "winning money" as some kind of global skill. A devotion to simply "winning money" has no more practical application than the proverbial "thoughts and prayers."

Since each sports requires its own individual process, becoming obsessive with one type of preparation should rarely result in obsessiveness regarding completely different types of preparation for other sports. A focus on process gives gamblers a chance, at least, to sidestep the addictive effects of gambling. Process, for example, has rules that set limits on what odds one is allowed to try to overcome.

The goal of winning money is in fact not some magical magnet that will draw people to it if they put in the hours and have some talent. Proper preparation and proper process are the only goals that can truly give players a fighting chance.

We'll return to the attributes of winning gamblers in future "White Crow" posts. As I obliquely touched on several times, I consider "staying in your lane" a key. The next time we discuss white crows, we'll tackle the issue of why it's crucial to stay in your lane, and also why most gamblers find it so difficult.


Bob Dietz -- May 26