INC 500 Entrepreneur (#21 in 2014). Author, Mastering the Trade. Options trader. Unschooler. Member: EO, YPO. Wondering if reality is only a Rorschach ink-blot.
Joined November 2008
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3 Feb 2021
This is a journal recap of my trading last year. Although I didn't trade $GME, I did trade plenty of $TSLA, $AMZN, and $SPX for a 1270%, $18.2M gain. Here's the blog: simplerjohn.medium.com/2020-…
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Jun 10
If you are into trading options around earnings - some cool tools, ahas, and strategies:
simplertrading.com/explosive…
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May 25
"You're navigating concept space, not commanding a consciousness."
This single sentence changed everything about how I interact with AI. And helps to avoid those rabbit holes . . .
10 ways to ask better — 🧵
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May 25
11/ The moment you'd give up is the moment to open AI.
That feeling of "I don't know how to figure this out" is exactly the trigger.
Most people Google. Most people ask a friend. Most people just stop. The bottleneck lives in your head, not the model.
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May 25
12/ None of this is about better prompts. It's about better navigation.
Once you start seeing AI as a high-dimensional map you're moving through — instead of a person you're talking to — the techniques become obvious.
The bottleneck is your mental model.
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May 7
Sam's really dialed in on this as a momentum tool, looking forward to seeing the updates. $SPX go.simplertrading.com/moment…
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Feb 6
Everything happening in the markets right now is exactly how it has always dealt with too much leverage. Like a horse swatting flies off with its tail. $SPX #BitcoinCrash An opportunity for the unleveraged to buy the dip.
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Feb 5
And here comes the liquidation event . . .
4 Nov 2025
Bitcoin holders have a record amount of debt against their holdings. I'm hearing that 80K is the level where some of these holdings get liquidated. Markets are like sharks that can smell blood miles away. #Bitcoin
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Jan 3
In the summer of 2024, I met a couple from #Venezuela at a youth program in Boston. They flew in for the event and our kids hung out together. They owned a small business in Caracas and were talking about the elections in their home country. They voted for the opponent, Edmundo Gonzalez, who stood in for Maria Machado after she was barred from running . . . and so did everyone they knew, to the point where it was obvious Gonzalez won. (It's believed he had at least 67% of the vote). They worried that Maduro would ignore the result and keep power. "He'll get support from the countries he does business with, like Cuba and Brazil, and he and his group run the country like it's their own business." Which, of course, is precisely what happened. Hopefully, this is a new dawn for the people of Venezuela. #venezuelalibre
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13 Dec 2025
Grok imagine laying out a new vision for our place in Wimberley . . . .
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