Niche Twins - Risk-taking in 2024
Mike's final newsletter of 2023 closed with the following message:
The signoff was a nod to Charlie Munger and Warren Buffet's views on when to diversify vs when to go ALL IN.
It was a great read as usual.
We then both took a much needed week off and headed to Disney World with the family.
It wasn't until near the end of the trip that my Mom reminded us of a ridiculous story from our childhood...
...a story that made me realize there was one specific word missing from Mike's newsletter.
First, the story.
It goes something like this...
Back in 1995, my Mom and Dad brought my three siblings and I to Disney World for the first time.
I was five years old.
At one point in the trip, we were all together in a shop at the resort. My parents handed each of us a $10 bill and told us we could go off and buy whatever we wanted with it.
Like normal human beings, my siblings all quickly ran off and pulled something from the shelves.
I on the other hand, like a borderline psychopath, went over to my parents and begged them to just let me keep the 10 dollars.
I mean what five year old does that?!
My parents, likely recognizing yet another conservative, risk-averse tendency in their son, insisted otherwise.
I could only have the money if I spent it.
So, what fun and interesting souvenir did I end up buying? Maybe a bubble wand or a Mickey action figure?
No. I bought a fuc*ing piggy bank. 😂
Which brings me back to the one word Mike omitted from his 'Stop praying at the altar of diversification' newsletter..."risk".
You can never truly 'swing out of you shoes' at an opportunity without preparation and conviction. That's absolutely true.
But you also need to be able to appropriately assess the risk(s) associated with the opportunity.
And as it turns out, on net, humans today are pretty sh*t at assessing risk.
When Sam Altman (CEO of OpenAI) turned 30 back in 2015, he wrote a blog post titled "The days are long but the decades are short".
In it, he offers a total of 36 pieces of life advice - things he's observed and things he's learned along the way. If you haven't read it, I highly recommend you do.
Of his list of 36, #15 has stuck with me since the day I first read it:
Throughout my own life, I have found this to be an incredibly useful worldview to default to.
Said differently, try starting your evaluation of any given opportunity with the baseline assumption that 1.) you're probably overestimating the risk involved and 2.) you're underestimating your ability to handle the fallout in the event the worst case scenario actually does play out.
Without being aware I was even doing it, I have approached pretty much every major decision I have made in my life by performing this "worst case scenario" exercise.
After college, when I was hyping myself up to move across the country (without a job nailed down and away from all of my family and friends), I would often play out the worst case scenario in my mind over and over again.
I would live in this fictitious world of not having landed the job I wanted, landscaping day and night to make ends meet and even needing to move back home after running out of money.
It's not that I ever truly expected any of this to play out. But by running and re-running these scenarios so many times I was able to see the "risk" of moving across the country for what it truly was - hardly a risk at all.
Years back when Mike and I were making the biggest financial investments of our lives, we would often call each other and run through the scenario of losing everything.
What would it look like? What would it feel like?
*Hilariously, for whatever reason, we would always end those calls agreeing that we could absolutely live in a trailer for a few years if it ever came to that. 🤣 *
Again, we never truly believed that was a likely outcome. And we're both fortunate enough to have a family safety net.
But the point is this - we both had the preparation and conviction needed to place the bet - we just needed this final piece of laughing in the face of the worst case scenario to pull the trigger.
My wish for all of you (and myself) as we take on 2024, is not primarily that you take more risks.
Instead, it's that we all get better at realizing when a risk is real vs when the risk lives only in our head.
Happy Friday!! ✌️
-Keith
Niche Twins newsletter sent weekly on Fridays at 8:30 AM ET
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