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3 Costly Mindset Mistakes Every Risk Taker (From Sports Bettor to Entrepreneur) Should Avoid In Their Career

Recently I had started talking to more sports bettors who have started to make real money gambling. As someone who has been an "Advantage Player" for 14 years - these conversations have me reflecting on my career.

One question pops out to me:

“What early career mistakes will I never make again?”

Many mistakes I will repeat (hopefully with decreasing frequency) over time. But the big changes that stuck were mindset changes. I wanted to highlight 3 mindset mistakes I made early in my career that I have since eliminated.

Eliminating these mistakes has made a bigger difference than any one gambling tip/trick I have ever received.

Let’s dive in:

Mistake #1: I Didn't Set My Goals High Enough

A good gambler can create a side-hustle that helps them achieve financial goals.

A bad gambler can lose their house.

But a legendary gambler can achieve freedom (financial and personal).

Don’t get it confused: a reliable second income is good, but it’s far from what makes the most difference.

Once I became a winning gambler - I took my foot off the gas and was happy to make a moderate amount of money. I would win money, take a break, need money, get stressed, win money... It was a terrible loop and didn't allow me to build a life.

It also didn't allow me to leverage my skill gambling because I never built a bankroll. Gambling is an amazing skill because it can compound your money. But to compound your money it turns out you need to have money. I didn't - and it meant I had to play for someone else and give them a % of my profits for far too long.

I only recently started playing my own money (last three years). And the reason I did was I knew it was the only way to create a sustainable life from gambling. My mindset shifted first from "I am happy being a winning player" to "I need to use this skill to create the life I want".

After this mindset shift, things started to naturally fall into place.

Mistake #2: I Had Shiny Object Syndrome

Until you’ve burnt your edge into the ground, don’t take your eye off the ball.

"When it gets easy is when you go hard"
- Alex Hormozi

I think about this quote daily because it reminds me to make money. You think making money would be an obvious goal of a professional gambler - but you would be wrong (at least in my case).

Over my career, I have had a lot of fun finding edges.

Finding an edge is like finding hidden treasure

It's exhilarating! You feel like Brad Pitt and George Clooney in Oceans 11 - you've found a way to extract money from a casino. And finding an edge is the most intellectually challenging part of sports betting. But I would argue that executing the edge is more of a character test.

The number of times I switched formats in poker right after I became a legitimate winner is embarrassing. I suffered from "Shiny Object Syndrome" - aka always trying to pursue something new and exiting.

My poker coach was the exact opposite - he played the same format of poker for years. He played every day, he reviewed every day and he improved every day.

He was a pro.

I was an amateur.

I was a great player (mainly because of his tutelage) but I had nothing to show for it. Being a great player isn't enough - you have to become a pro. You really start winning at gambling when you can come in every day and do the boring stuff.

Now I would say we (me and my partner: Damedolla) live by a 80/20 rule.

80% of the time we spend executing on our "fastball"

20% of the time we spend on R&D

This is optimal for us - but earlier in my career I would argue 95/5 is even better, because building your bankroll so you can play your own money is so important.

Mistake #3: Thinking My Edge Will Last Forever

We all tend to think current circumstances will last in perpetuity.

When applied to gambling:

We all think we have unlimited opportunity to exercise the edge we found(and project our earnings accordingly).

We all think we are immune to the market adapting, the sportsbooks learning and the rules changing.

But the truth is, we’re not.

Know that edge finding is the skill that you will be able to constantly leverage and improve.

It's scary to acknowledge that your edge won't last forever. When you acknowledge this you also acknowledge:

  • You can't accurately project your future earnings (impossible anyway)

  • You will have to change in the future to remain a professional gambler

  • Learning is always going to be a requirement of this career (is this even bad?)

I still have moments of existential dread when considering that all the edges I have today I probably won't have in a couple of years. But I used to "solve" this problem by not thinking about it - not acknowledging it. This caused me massive anxiety because I wasn't living in reality.

Now I accept the fact that edges disappear. This allows me to align my decisions with reality. This means that:

  • I am more conservative with spending money - this helps protect me from potential periods where I don't even have an edge

  • I allocate time to R&D - this creates a systematic way to preempt the inevitable loss of current edge

  • I share edges with other bettors - sharing is caring. Often when I share edges, they offer edges they are seeing in return. I used to be really secretive, but I got so much out of networking and adding value to other sharp bettors

Anxiety around losing your edge will always exist. Mitigate it by facing the fear head on. Take the steps you can to best deal with this reality of ever-changing markets.

I hope some people reading this can learn from my mistakes. If you got something from this newsletter - please give it a share.

If you are reading this and haven't subscribed - please do. The more people I know are reading this, the more incentive I will have to push these to be better and better.

If you want to join my (free discord), listen to my podcast or learn more about what I am doing - check out https://www.goldenpants.com/

Thanks for reading!