What the heck happened in 230+ episodes!?
Over four years, I’ve talked to hundreds of founders and game-changers building a better future.
Many of them have gone on to raise (hundreds of) millions of dollars and become personally wealthy. Others have shut down their businesses for good.
Do I remember what I talked about 130 episodes ago? What were common themes? What was the stupidest thing I ever said? What was the most prescient?
I’ve always longed for information like this, and now, with RAG models and AI, it’s possible to query every episode I’ve ever done.
“What were the five most common themes that connected everyone I’ve spoken to?”
“What is definitive, concrete proof Ross is a moron?”
We can now query our data in near real time, adding tremendous meaning to the treasure trove of back content each of us has created.
The vital skill our kids aren’t learning
It’s clear our school curricula need to change. Fast. Dramatically.
As the parent of children soon entering the critical schooling years, I know that I want them almost solely focused on three things: Practical use of technology (like AI), business (accounting and corporate structures), and logic.
We spend no time at all teaching our kids about logical fallacies, and yet they are the very center of coding, human machine interfaces, media literacy, and just about every other vital skill in modern society.
“You are stupid, therefore you’re wrong” is a classic fallacy we see every day.
But this does not cohere.
The Wikipedia page alone lists hundreds of such fallacies, but how many children can name even one?
Transformative
This one word is at the heart of legal debate surrounding AI, and it’s the cornerstone of copyright law.
“Fair use” is what lets us all (re)mix the elements of copyrighted works—the entire platform of YouTube is built on the concept. But no one can really define it. There are guidelines, but you’ll never get anything more than a few loose concepts that are completely up to interpretation.
So when AI is trained on Disney, and it outputs something that is satire, commentary, or derivative, is that fair use? Does fair use apply to AI like it does to people? (Keeping in mind that fair use doesn’t stop corporations from suing regular people every day.)
In the latest legal battles, the right of AI to be trained on copyrighted works has so far been preserved. Because what AI spits out is “transformative”. If I use Mickey Mouse to sell my daycare, that’s theft. But if I use the character to make a satirical point about how Disney employs more lawyers than animators, that could be fair use.
Personally, I love transformative work. It’s how we speak our minds in the modern era.
But our desire to transform shouldn’t end at copyrighted works. It should extend to our use of AI itself.
One use of AI is just copying its outputs and saying “good enough for me!”
But it’s far better to take the outputs of AI and transform them into something new. Something uniquely ours.
Something we’ll never have to deal with again
One hundred years ago, if you wanted to learn the new hot dance moves, you’d have to open a book Like Arthur Murray’s How to Become a Good Dancer (1938), and you’d be greeted with a handful of static images and paragraphs like:

“Steps 1 and 2 get a time count of 1, 2 each; steps 3 and 4 get just 1. This basic pattern of the Shag is called the “Time Shag,” and it should be done twice before you break into a Shag Dip or Side Break…”
Makes perfect sense to me!
Now I’m sure old Arthur tried his best, but did anyone become a good dancer from reading that book?
Take comfort knowing that we’ve quietly moved from a time when nothing works and we don’t know why, to an era where everything just works and we don’t know why.
Your new car payment
We’ll all be spending >$250 monthly for AI tools in short order.
And someday soon?
AI will be similar to a car lease—the next non-negotiable expense in addition to healthcare, housing, and a car (in the U.S., at least).
Today, most AI services are around $30/mo.
But not all of these tools will survive, as their features get rolled up into bigger and better models.
Instead, the price will go up on the 1-2 best, our true AI companions, and like taxes and interest, we’ll have no real choice but to pay.
