Sep 30, 2026 · 18 min · 8 segments
Online shopping gives us enormous selection, but selection isn't the same thing as clarity. This episode is all about how AI changes the shopping conversation, not by magically finding the perfect…
We talked a little bit about subscriptions last week, and it's not because I think AI wants to us to have every decision made for us.
I like to shop.
I like figuring things out.
I like to look at the pluses and minuses of things.
It can listen to your whole problem.
And that turns out to be really important.
A friend of mine had this problem that almost everyone who's ever loved a particular shoe has.
She found a shoe she liked.
It fit her feet and it felt good.
And the thing that she knew is that she knew exactly which model to buy and what size to buy.
And she kept buying those same shoes over and over again.
And then the shoe company changed the shoe.
And this is one of those, we get that all the time, little betrayals of modern life that no one warns you about.
You find the perfect running shoe, the perfect walking shoe, the perfect hiking shoe, the perfect brand of pants you like to buy, whatever it is that just fits you perfectly.
And then the manufacturer decides to improve it.
And they change the shape.
They change the foam.
They change the toe box, the heel, the cushioning.
And then it just moves just a few millimeters away.
And now it hurts like crazy.
It's a model that has happened to me a million times.
I used to have these trail running shoes I just loved.
And like clockwork, they just decided we're going to come out with new trail running shoes.
They made it completely different.
We talked a little bit about subscriptions last week, and it's not because I think AI wants to us to have every decision made for us.
I like to shop.
I like figuring things out.
I like to look at the pluses and minuses of things.
It can listen to your whole problem.
And that turns out to be really important.
A friend of mine had this problem that almost everyone who's ever loved a particular shoe has.
She found a shoe she liked.
It fit her feet and it felt good.
And the thing that she knew is that she knew exactly which model to buy and what size to buy.
And she kept buying those same shoes over and over again.
And then the shoe company changed the shoe.
And this is one of those, we get that all the time, little betrayals of modern life that no one warns you about.
You find the perfect running shoe, the perfect walking shoe, the perfect hiking shoe, the perfect brand of pants you like to buy, whatever it is that just fits you perfectly.
And then the manufacturer decides to improve it.
And they change the shape.
They change the foam.
They change the toe box, the heel, the cushioning.
And then it just moves just a few millimeters away.
And now it hurts like crazy.
It's a model that has happened to me a million times.
I used to have these trail running shoes I just loved.
And like clockwork, they just decided we're going to come out with new trail running shoes.
They made it completely different.
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