Last summer I ran a series (that I later combined into one VERY long newsletter) called Gambling Lessons Learned. That missive hoped to share some of the lessons I personally learned over the years of being a successful gambler to prevent some of you from having to learn the hard way as I did!
Well, some new ones have come up since then so I thought, well, why not do a Part 4?
Your bets are your responsibility
Whether it is my professional or personal life, taking personal responsibility has been something I have seen as a huge differentiator between people who are successful and those who aren’t. That is true in gambling too.
When you go on an app or a website, add a ticket to your queue, type in a dollar amount, and click submit - you have to realize that is you making the choice to put your funds at risk.
Yes, I know if you are following someone else’s picks (e.g., some Twitter tout, someone you see on TV, me, your buddy from college) it is easy to want to point a finger if the picks lose, but if you want to be a good long term bettor it is important to take the responsibility for your own action.
For example, I have seen a lot of people lose money hand over fist with a specific Twitter tout over the last 18 months. They complain and blame him for having them going broke, but they do not look into the mirror and ask “Why after months and months of losing are you still betting those picks?”.
Yes, every bettor has hot streaks and cold streaks, including me, but if you are practicing effective bankroll management, you should never be anywhere close to blowing a full bankroll because of a “cold streak”.
Avoiding losing bets is as important as finding winners
See here is the thing, many gamblers love betting on everything; I know I do! What folks do not think about is that eliminating losing bets is just as valuable as finding winning bets! Too many seem to focus on bets they could have made that would have won but don’t think about the losing bets they did not make; which are just as valuable.
One of the things I did not anticipate when I started this Substack was the number of folks out there who were gambling and losing and wanted to get better. I have worked with about a dozen people in the last year on trying to help them get from losing bettors to winning. One of the VERY first things we do is take a look at what sports they are betting on.
If a newly graduated college kid came to me and said they were getting into sports betting what sport should they pick - I would say, whatever sport you like most and ONLY that sport. Become an expert in it. Listen to all the podcasts. Read all the books (more on this later) and articles. Watch the game tape. By being an expert in a sport you will have a decent chance at figuring out what bets have value and what do not. Once you are profitable in that sport add another one.
Now, if you are here, you may not be new to gambling so I know what I am about to say will sound pretty hypocritical given that I am someone who is willing to bet on pretty much anything BUT if you have been struggling to find long-term profits or feel like your profits should be higher than they are you should start by limiting the number of sports you are betting and really focus on 1 or 2 key sports that you love and seriously become an expert in them1.
Betting on sports you do not watch or know anything about is generally a recipe for losing money. Remember what I said above, your bets are your responsibility, even if you are getting them from someone else so make sure you are at least watching or understanding the sports you are betting so that you can act as a filter for those bets.
You know how I said I bet a ton of sports? Sure, I do, but I think of myself as an expert in really 2 sports - NFL and PGA. So what do I do for other sports? Well, I watch a TON of sports so I use the knowledge that I gather from being a general sports crazy however I bet in smaller increments. Additionally, I also tend to be very strategic in how I bet on these other sports and even have some folks I trust to follow for their action. For example, I might look at a full MLB card and bet 1 or maybe 2 games or none at all. As such, my summers are rather quiet from a betting perspective.
You should not feel like you HAVE to bet every day or every sport.
Make sure to learn your history
I was just talking about being an expert in a sport and some folks might take that to mean knowing the backup QB on every NFL team or being able to reference the BABIP of Garrett Cole his 3rd time through a lineup, and sure that is certainly part of it, but folks do not spend enough time learning the history of the sports they watch.
Now you do not need to go back to when the NFL was played without helmets or when basketball was played with peach baskets, but learning the history of your sport will make you significantly better. For example, if you are in your mid-20’s and a big English soccer fan, I would suggest you invest some time learning about the years prior to the premier league coming into place.
As they say, “Those who do not learn from history are doomed to repeat it”. For gambling, we want to know what is repeatable. Learn your history so you can see when something is happening.
Folks saw the running attack the Chicago Bears (and to a lesser extent the Eagles) used in the 2022-2023 season and thought they had invented a new style of football. Those are folks who have never heard of the Wing T, which was an old-school offensive system that these teams modified. If you recognized what they were doing then it became an exercise in studying defenses to see who would be disciplined enough in their keys to maintain gap integrity and slow them down.
There are plenty of books, podcasts, and documentaries that will help you learn about the history of the sports you handicap. Check them out!
Hedging
I get asked about hedging quite a bit and I always say that hedging is a personal choice as it is something each person should evaluate for their own risk tolerances and bankroll. While that is absolutely true, one thing I have seen folks do is taking what they think are hedges but are really losing propositions.
When taking a hedge, I highly recommend spending a bit of time thinking “Is there ANY way I can lose both my bet and hedge?” As you will note, I said any and not likely. A perfect hedge is one where there is no way for you to lose both and that is absolutely a hedge worth consideration.
If you have a “hedge” you are considering AND it includes outcomes that can cause you to lose your initial bet and your hedge then you have to think long and hard about the percentages and if it makes sense to do it.
A good example is folks will bet a team to win the NFL championship and once you get to the conference finals they start to get antsy and want to “hedge”. Well you could bet against them in the conference finals, but they could win that and still lose the Super Bowl so you really haven't effectively hedged. We had exactly that last year with our preseason Eagles bet.
Another example where hedging can be hard is, in a sport that I love to bet on, golf! There are very infrequent markets that will allow you to effectively hedge so it is important to understand what outcomes could cause you to lose all your bets and to calculate the implied odds of that happening and compare it to the real odds. From there you should do a personal assessment of whether that risk/reward ratio makes sense and almost always it turns out to be a massive -EV decision to enact that hedge (very similar to cashing out a ticket).
Continue to be very careful of who you trust
This section is a late addition to this newsletter as most of this post was written and refined over the last few months but this one was written in the last 2 weeks.
I continue to be astounded at how many people on gambling Twitter continue to be absolute pieces of shit (excuse my language) when it comes to transparency. The latest is a person I used to think highly of who went around posting really great golf results, but one thing I realized was that he put up posts/tweets for things like DPWT, LIV, and other golf bets but NONE of those were listed in his results UNLESS they won!
When I noted that to him and showed him an example of a live bet he won that he included and one that he clearly did not include - his response was (exact quote) “Everyone pads their stats”. That is HOT garbage.
I am someone who preaches being careful and this is someone I would have trusted and suggested people use and I would have been wrong. Make sure you are keeping a close eye on ANYONE you get picks from, including me!
Do not get overzealous because of early wins
I get a lot of guys reaching out to me that ask for my help in being profitable bettors and one the stories I hear most often is “I started out winning a lot, but my results have turned against me and now I’m down quite a bit”.
I am not sure if beginners’ luck is a real thing or if there are just as many folks who start betting and lose right away so they just walk away, but when you start winning early in your gambling journey it can be intoxicating and can make you fall into lust with gambling.
Yes, I am using terms that we usually use for relationships as we have all been there right? A super attractive person enters your life. It is a whirlwind early on, but then things turn sour. Well, that is the gambling version of what these people experienced. They likely showed up with incorrect notions of how gambling works, no bankroll management skills, and/or poor betting hygiene but it worked out so they developed bad habits and then when they were no longer on that hot streak or getting lucky, things turned bad quickly.
Any healthy long-term relationship is built each and every day through diligence, consistency, effort, and the acknowledgment that not every day will be a good day. That is the same with gambling.
In gambling, you will hear people say “The house always wins”, but the more accurate statement is “The house always wins……in the long run”. That is because they understand that there are always hot streaks for bettors so they will have losing days, weeks, and even seasons, but the vast majority of bettors do not have the discipline, tools, knowledge, or consistency to beat them over the long run and they will just outlast you. If you want to be part of the 5% who are profitable long term, you have to think of it as a long-lasting relationship that you work towards.
A work of warning on becoming an “expert” about a sport, you will realize that 99% of people (including former you, friends, colleagues, in-laws, and guys on TV) do not really know what they are talking about and you will get frustrated BUT when you find someone else who is an expert. You will find those discussions incredibly rewarding and thrilling.