15 important lessons from experienced sports bettors
Helpful tips from a variety of long-time bettors on lessons they learned
There is an old adage that says, “Those who can’t do, teach.”
I have always derived more joy from dispensing information relating to sports betting than giving my actual handicapping of various games. I know what I’m good at — and telling you which teams to bet on isn’t it. While I have plenty of subject matter expertise from being in the sports betting industry since 2010, my value is in the relationships I’ve cultivated over the years, resulting in a Rolodex of bookmakers and bettors whom I can turn to on occasion.
For this piece, I texted 15 different bettors and asked them about a lesson they learned the hard way or were taught by someone early in their betting careers. The resulting quotes hopefully will help you improve as a bettor and hit on everything from bankroll management to the importance of networking to mental health and betting.
Enjoy!
If you’re new to my Substack, here are a few of the types of articles you can expect:
“One early lesson I learned from a mentor was to always look first at underdogs and unders. Bonus advice I would give to new bettors now would be to sign up for all legal books, play out the bonus and decide which ones you want to keep.”
“Every guy thinks he can do it, but the truth is less than 5% of those who try can truly make a living as a professional sports bettor. And it’s not a glamourous life.”
“The best bet in sports can be a focused favorite, like UConn in this year’s NCAA tournament, but if you want to win consistently and long term, you have to play mostly underdogs.”
“You will only be as successful as your ability to overcome negative variance.”
“I think the best advice is to not be greedy, be easy to work with and try to see as many plays from actual people who win. Without knowing what winning looks like, it’s very hard to win on your own.”
“NEVER bet outside your means.”
“The best lesson I learned early on as a sports bettor was understanding that no team is as good or as bad as it was in its last game. Each day presents a different opportunity with new context provided. It’s crucial to eliminate recency bias from your handicap.”
“You can never have too many outs.”
“You are only as good as your network.”
“Don’t silo yourself off. You can have your process, but don’t shut yourself off from opinions of others in the sports betting space.”
“Don’t be the smartest guy in the room, just try to make some money. I’ve been betting for a long time, and I wasn’t nearly as good as I am today. It took a lot of losing seasons and ditching bookies in the early 90s to get to this point. People should know that every game is its own entity and find what works for them. There is almost too much information available for bettors these days.”
“Not knowing or being unsure isn't expensive. Thinking you know something when you actually don't is what breaks people.”
“The most important lesson for me is when I learned that it’s important to take breaks. It’s easy to be obsessed, especially with the seven-day-a-week sports (MLB, NBA, NHL). There are lots of ups and downs in sports betting that can throw you off your game, so it’s beneficial for your mental health, and often your betting results, to disconnect every once in a while.”
“One of the first bits of advice I was told was never to get too high or too low. It’s super cliche, but it’s important to be in the right mindset when handicapping so you can stick to your principles. Letting your emotions get the best of you can lead to reckless wagering, but can also impact your mental health in ways that go beyond betting the games.”
“If you're new to sports betting, my first piece of advice is to know what you're getting into and set realistic expectations. No one wants to tell you this, but sports betting is hard. If you think you'll become a millionaire or get good enough at it to quit your job and bet full time, you are mistaken. Instead look at sports betting as a "side hustle" with the goal of turning a hobby into an investment.
“Second, make sure you set up a disciplined bankroll management plan before you place your first bet. Come up with a number that, if you lost it all, wouldn't affect your everyday life. Consider it your disposable income. Then, embrace flat betting. This means risking 3% of your bankroll per play and always bet to "risk" not "win." For example, if you start with $100, this means you are risking $3 on every game. It may not seem sexy, but it will keep you in the game long term. Then, open up accounts at multiple sportsbooks so you can shop for the best number. Don't bet too many games and, finally, avoid parlays (especially same game parlays). They are the penny slots of sports betting, making a killing for the house and not the bettor.
“Lastly, bet with your head and not your heart. Don't bet with emotion or gut instinct. Don't blindly bet your favorite teams. Don't handicap games on what you think, want or expect to happen. Instead, learn how to analyze the market. Get access to a live odds page and learn to read line movement (what a line opens at and where it moves). Consult betting splits so you can see the percentage of bets and money on every game. Try to take a contrarian approach. Lean toward underdogs and unders. Always try to place yourself on the side of the house and with the sharps who win at a high rate.”
