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Low Stress Bets Memo #4- September 14, 2026

Sep 14, 2026
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Just like that, the first NFL Sunday of the season is in the books. I hope it was a profitable one for you if you bet. Now that the season is underway, let's consider how to keep having success all the way through Super Bowl Sunday (which is also Valentine's Day- you're welcome for the reminder five months ahead of time 😃.)

Today's legendary investor guidance is from Howard Marks, co-chairman of Oaktree Capital Management.

Howard Marks is known for writing memos focused on long-term thinking, psychology, and markets. Oaktree was founded 31 years ago and manages roughly $220 billion for its clients, so the organization is a wonderful example of long-term staying power.

In Marks' words from 36 years ago:

"If we avoid the losers, the winners will take care of themselves.

I feel strongly that attempting to achieve a superior long-term record by stringing together a run of top-decile years is unlikely to succeed. Rather, striving to do a little better than average every year – and through discipline to have highly superior relative results in bad times – is:

  • less likely to produce extreme volatility,

  • less likely to produce huge losses which can’t be recouped and, most importantly,

  • more likely to work (given the fact that all of us are only human)."

The full memo is here, called "The Route to Performance".


The Link to Serious Sports Betting

One of the greatest investors of our generation is giving us the blueprint for 3+ decades of success: a little bit better than average every year is going to become multilples better than average over the long run. Furthermore, he goes on to say: 

"we want the concept of risk control to always be top of mind for our investment professionals. 

When they review a security, we want them to ask not only “How much money can I make if things go well?” but also “What will happen if events don’t go as planned? How much could I lose if things get bad? And how bad would things have to get?”


Low Stress Takeaways

  • Plan to play the long game: Everyone has a different time horizon, but if you want to succeed in betting, have a clear plan for your version of "the long run."
  • What's "a little bit better than average" and how do you get there? A positive return; you get there by maintaining a strict focus on risk management and considering all possibilities on a bet.

  • Losing bets can be avoided: Stop trying to aim for outsized returns on every bet and focus on what you know best.


The LSB Community is Almost Here

The Low Stress Bets Community opens within the next week. It's a risk-management workspace built for serious bettors who treat sports markets like a long-term portfolio, not a noisy gambling forum.

Thank you to everyone who has already claimed seats and given me feedback about this setup before even seeing the community. I took your suggestions, and the first month is going to be free for everyone. I'll continue incorporating your input to make this the best possible resource to help serious sports bettors build the mental tools for success.

I'll send an email this week when the community officially opens.

To claim your spot, click this button:

 Join the LSB Community


Thank you for reading this edition of the Low Stress Bets Memo. Reply directly to this email with any thoughts, questions, or feedback—I read every response.

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Low Stress Bets focuses on mental models, risk management, and psychology for the serious sports bettor.

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Low Stress Bets focuses on mental models, risk management, and psychology for the serious sports bettor.

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Low Stress Bets focuses on mental models, risk management, and psychology for the serious sports bettor
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