The Story of Oscar
This story has two purposes:
https://t.co/EFiBwSU3pz show that my ideas generate alpha and why you should consider the trades I share.
https://t.co/VXrJpO1OZp tell a simple story about trust.
In 2022, after years of easy money, the Fed pivoted. Volatility returned. I tweeted: “Things are finally getting interesting.”
A few people and funds reached out, one of them was Oscar.
He started with a small amount that he wanted me to manage, then added more as the year went on. We clicked right away. No management fees. I only charge a performance fee at year-end, if the client wins, I win.
By year-end, Oscar was up ~20% thanks to the $VIX strategies. The S&P was down 18%. I calculated my 20% success fee, then realized we never signed anything.
I told Oscar the number and added, “You can pay whatever you think is fair.”
He was offended:
“We agreed on X. Why would I pay you less?”
I smiled. “That’s true.”
As you can see below, Oscar did well in the years that followed using the same strategies I recommend here.
We’ve been friends ever since. Every once in awhile we talk markets, real estate, and life. This year, we’re finally meeting in Madrid.
Still no contract.
Just trust.
Todo Cambia.
A good trader always evolves. No system works forever. Most fail not from lack of intelligence, but from clinging to what once worked.
Even Buffett had to pivot — from “cigar butts” to high-quality businesses. That shift, rooted in logic and humility, unlocked his greatest returns.
Books like Market Wizards. The trades are irrelevant. Most of those legendary traders are retired — because their strategies stopped working. And that’s the point.
A strategy that works is like a wave in the ocean. It forms, it rises, and those who catch it often believe they’ve found the golden formula. But every wave eventually hits the shore and dissolves. Then comes the real challenge: letting go and finding the next one.
The lesson isn’t what they did — it’s how they thought. How they built a system, recognized when it worked, and walked away when it didn’t.
The edge isn’t brilliance. It’s adaptability.
One of the best lectures I have ever seen on risk and volatility by Howard Marks, @Oaktree Capital Co-Chairman.
I recommend watching it at least 3 times and to take notes while you do.
https://t.co/94jfy0A9eX
I keep getting asked: “How long are you planning to hold this stock?”
It’s a question I can’t really answer.
Imagine you just started dating someone and I ask, “How long are you going to stay with her?”
You’d probably say: I don’t know. Let’s see.
She looks good, acts well, talks well. That’s the initial thesis. But then you learn more. How does she behave with your parents? How does she treat people? How does she react when things don’t go her way?
Any one of those things can change the thesis.
Stocks are the same.
I could be out of $SNAP next quarter, even at $5, if I see that things are not developing the way I expected.
Or I could still be holding it at $20 if Evan Spiegel and management are actually making the changes I believe could unlock value.
Maybe you hold for a month. Maybe a year. Maybe ten years.
The holding period isn’t decided when I buy.
The thesis is.
And I hold for as long as the facts continue to support it.
𝗥𝗔𝗡𝗞𝗜𝗡𝗚 𝗧𝗛𝗘 𝗡𝗘𝗢𝗖𝗟𝗢𝗨𝗗𝗦 𝗕𝗬 𝗖𝗘𝗢
Look into Michael Jordan’s eyes and you can see the killer instinct. Look at Deandre Ayton’s eyes and you see softness. Watch Elon speak and you can see how deeply he thinks. Watch Carlos Ghosn and you immediately see a villain.
If you’ve followed me long enough, you’ve seen me make a few calls simply by reading the person running the company. Trevor Milton was probably the best example. When Nikola was worth tens of billions and Wall Street loved it, I said the guy looked like a scumbag. I never read a financial statement. The stock eventually collapsed and Milton went to prison.
There were a few other cases, but they’re irrelevant here.
So let’s do something different. $BTDR, $IREN, $CRWV and $NBIS. I’m going to rank them purely based on the gut feeling I get from the people running them, starting from worst to best.
𝗖𝗛𝗘𝗔𝗣 𝗜𝗦 𝗡𝗢𝗧 𝗔 𝗧𝗛𝗘𝗦𝗜𝗦.
$PYPL is a good reminder: whatever everyone is talking about on X is already priced in. Cheap is not a reason to buy, opinions without a track record are just noise, and the less X influences your judgment, the better.
I’m not in this trade, but it definitely makes me think. Volatility is extremely low, so after a strong move down, especially something like Nasdaq down 7 of 8 days and Nvidia down 7 straight, you can start picking up cheap calls as lottery tickets. You don’t need to be right often. One big winner can pay for the rest. Food for thought for myself.
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