18 Comments
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Jason K's avatar

Great article and I needed to hear this. The last few years have been very nice. I won't seek it out but it is good to have someone way shake you back to reality and offer the advice to not take your wins for granted.

Please check in on me often and maybe a slap across the face next time to make sure I am taking this advice all in.

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Mike G.'s avatar

Agreed. Fantastic article that I will revisit often. I also find anything written by Morgan Housel helps keep me in check whether it be his blogs or his books. And I've also found https://moretothat.com/the-nothingness-of-money/ to be helpful. We are so fortunate to have Jack Raines, Morgan Housel and other great content providers help us through our financial battles.

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Joe Marshall's avatar

i wish I could easily forward this to every one of my clients - lot of them are tech professionals who won the lottery and instead of cashing out of most and being set, continue to buy more lottery tickets by holding onto the stock

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Chris James's avatar

I wrote an essay that you and your clients might enjoy. It’s called The time I invested all my money in one stock

I’ll circle back and link it

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Wonton's avatar

“But if you made a life-changing amount of money on a concentrated bet, it’s worth considering whether it makes sense to risk that now-life changing sum to make an additional, no-longer-life changing, amount.”

Brilliant — my key takeaway, and agree wholeheartedly

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Sara's avatar

Loved this. It can be really easy to think about investing risk from a purely financial perspective and forget about what those potential gains/losses actually mean for our daily lives.

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Marcis's avatar

Hey, man!

I've been reading you almost since the beginning of your substack. I like how your language and writing style has evolved. good stuff!

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Spencer Burnstead's avatar

Great read. I will say, not having a significant allocation to crypto has never made me feel more dumb lol.

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Brian's avatar

Excellent!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!

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Darnell Mayberry's avatar

Thank you for this. I began my investing journey in September 2022 and have had to learn a lot about psychology and temperament in investing. I will come back to this often. Well done!

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Supertramp's avatar

You only have to get rich once.

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Pete Tittl's avatar

So smart! Great advice

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Chris James's avatar

I had to get rich twice. I put my entire investment portfolio into Tesla in 2019. Then borrowed and bought more. It went up a lot and I quit my job at Tesla. Then it went to 1.8 million. I borrowed and traveled and messed around and went insane.

And then it crashed.

I’d borrowed 330k and got margin calls and couldn’t pay rent and had to sell my stuff and including shares at the worst prices in years. Fortunately I walked away better than ever and the Tesla stock price went to the moon a few months ago and I sold a ton of shares and now I’m mostly in T-bills.

Now I have capital to take care of my health and create awesome stuff

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salvatore's avatar

awesome post mate, finance may be taught as a mathematical discipline but trading/investing is very much a psychological/emotional one - love your insight on how it doesn’t makes sense to trade a life-changing amount of money for the chance to win a bigger but not life-changing amount of money

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Jared Brown's avatar

America disproportionately rewards risk-takers, even if they fail many times over.

Great post.

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The Working Class Investor's avatar

Once I hit my number I'll stop investing and coast off the yield unto death. Once you've hit your number there's no benefit to piling on additional risk.

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Grant Varner's avatar

Agree that the you only need to get rich once—assuming you don’t lose it all on a risky bet.

Unless you’re in finance for a living (I’m not; I’m in tech sales), the fastest way to get rich is just making a lot, spending a little, and investing in low-cost index funds, like S&P500.

It’s not as sexy as riding Hawk Tuah Coin to the moon, but it’s worked for me so far.

https://open.substack.com/pub/grantvarner/p/fastest-way-to-get-rich?r=3221f1&utm_medium=ios

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Ki Lo's avatar

Everything starts with an idea.

You need to document, vet, and organize all your new business ideas.

Forecast start-up funding requirements, revenue, and profit.

Don't use a napkin to document your idea, I use EntreQuick.com

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