“Some of it you learn the hard way

Some of it you read on a page

Some of it comes from heartbreak

Most of it comes with age

And none of it ever comes easy

A bunch of it you maybe can’t use

I know I don’t probably know what I think I do

But there’s something to some of it”

As I drove across Canada a week ago to my mother’s 60th birthday, the new song by Eric Church continuously came on the radio. The song, fittingly about life lessons, got me thinking as I cruised through the mountains. What if I got the chance to start over and go back to the Dominican Republic with $2,000 in my pocket to see how long I could last betting on sports? Where did I go wrong and what would I do differently?

If you are a new bettor, I hope these can help. If you are an experienced bettor, I am sure you can relate.

Sports betting never ends

When I made my first deposit into an online sportsbook at the age of 15, I was obsessed with turning the $100 into $1,000,000. I lived and died with every $10 wager I made and had a goal to win money every day. It took me a number of years to fully understand that sports betting never ends.

There is always a chance that the opportunity tomorrow is better than any opportunity today. The only thing preventing bettors from taking advantage of those future opportunities is forcing wagers and losing money on bad decisions today.

‘Short term success does not matter’ is unfortunately interpreted too frequently as an excuse, instead of sports betting truth.

Nobody controls the outcome

I was fortunate enough to have someone send me an email I sent them analyzing a football game in 2010.

Two sentences in, I wanted to go back in time and smack myself in the face. The entire premise of the analysis was based upon statistics that “I” found and research that “I” did.

It became clear to me that bettors have an edge in passing on bets. Selectivity and patience are two key skills to master

I was completely convinced – and did my best to convince others – that because I was betting on a game it had a better chance to win. It humbles me to say that upon starting out, I believe that I had control on the outcome. As a hyper competitive person, this was a specifically hard lesson to accept as it forced me to put my ego aside. It was not until I did, that I was able to learn and become better.

Saying no is often the biggest edge

This is not a lesson I understood until my second year of setting prices as a bookmaker. Account balances were up, company revenue was down, and bettors were picking apart soft prices in the middle of the summer.

I was overwhelmed by continuously having to open up full game, first half and secondary markets for all games on the board each day.

Fast forward years later and reverse roles, it became clear to me that bettors have an edge in passing on bets. Selectivity and patience are two key skills to master.

Prices not predictions

I got into sports betting mainly due in part to my love of sports. The competitive nature of playing sports growing up fuelled this idea when I started betting that I was smarter than everyone else and knew more than the betting market.

Had I focused more on prices than predictions in the early stages of my career, I have little doubt my arc of success in the industry would have been accelerated dramatically.

Separate bankroll from life

I have a vivid image in my head of a blue stack of $2,000 Dominican Peso bills on my night stand with betting tickets wedged in-between. When I first started out, I would live life and bet out of the same bankroll.

Looking back, the toll that this took on my mental well-being was astonishing.

My lifestyle outside of betting was entirely predicated by the success of my wagers. It is impossible to estimate how much being emotionally connected to every wager cost me early in my lifetime, but it is an enormous amount.

Separating betting resources from life resources is critical for success.

So, what if I started over?

As tempting as it would be to go back to walking around Punta Cana with a wad of pesos in my pocket boasting about how right I was about the football game that just finished, I am glad I made it through those times somewhat unscathed. There is a ton of truth in how enjoyable betting with emotional investment and living for tonight is, but I much prefer what I have settled into now.

I can say with full confidence that the success that comes from separating life from betting, focusing on the long term, buying good prices consistently and detaching myself from the result, is far more enjoyable than the alternative.

None of it ever comes easy, but you will find the same success if you can get there too.