Everyone who watched Smerconish this weekend knows exactly what I’m talking about.
I asked ChatGPT to draw a caricature of me using everything it knows about me. And it did.
It was funny. It was sharp. It was weirdly accurate.
And then it hit me.
Why was it able to do that?
The Nest footage.The subscription confusion.The question that won’t go away.
Are these companies actually deleting what they say they’re deleting?
I have been obsessed with privacy since I was a teenager.
Not in a paranoid bunker way. In a constitutional law way. In a technology native way. In a “I grew up during Edward Snowden” way.
I remember sitting in high school watching the Snowden revelations unfold in real time. I remember the Apple iOS location tracking headlines. I remember Apple having to publicly explain why people’s phones were logging their movements. I remember thinking, nobody actually believes any of this is private.
Most intelligent people don’t operate under the illusion that what we do online is invisible.
The real question has never been whether you are being tracked.
The question is how hard you are making it.
From a young age I’ve been the tech guy in my family. The one people call when something breaks. The one who reads the privacy policy. The one who understands what TOR is. The one who knows what a VPN does and what it does not do.
I use DuckDuckGo. I use a VPN. I use email aliases. Not because I’m a criminal. Because I believe in friction. I believe in obstacles. I believe in personal responsibility when it comes to your digital footprint.
When Smerconish’s segment touched on TOR and dark web familiarity, I wasn’t shocked. I was relieved. Relieved that we are finally having adult conversations about the tradeoffs between technology and privacy instead of pretending we can have one without the other.
Technology is not going anywhere.
And frankly, I do not want it to.
I like the utility. I like the speed. I like the leverage. I like the power.
But let’s not lie to ourselves about the business model.
If the product is free, you are the product.
Your data is the currency. Your behavioral profile is the asset. Your attention is the inventory.
Even ChatGPT is moving toward ads. Of course they are. They are sitting on enormous traffic. It would be irrational not to monetize it.
Here is my controversial take.
If data is being collected anyway, I would rather see relevant ads than irrelevant ones.
That does not mean I want more monitoring.That does not mean I want more sensitive information harvested.That does not mean I trust these companies blindly.
It means I understand the model.
I do not believe sweeping legislation is going to magically fix this. These companies have enormous lobbying power. We saw what happened with iOS 14. Apple restricted tracking and Meta adapted. The machine adjusts.
But I do believe in clarity.
If a company says incognito, it should mean incognito.If they say temporary chat, it should mean temporary.If they say deleted, it should mean deleted.
The onus should be on the company to define exactly what those words mean.
And if they mislead, there should be consequences.
That is where something like a digital bill of rights or a GDPR style framework becomes interesting. Not because it will eliminate tracking. It won’t. But because it establishes enforceable standards of disclosure.
What fascinates me most is the psychological layer.
We have all had that moment.
You mention something in conversation. Not over text. Not typed into a search bar. Spoken out loud. And suddenly you see an ad for it.
Is the phone listening? Is it metadata? Is it predictive modeling based on a thousand other signals?
We all suspect something.
No company will admit it.
And that tension between suspicion, utility, profit, and constitutional rights is exactly why I had to make this video.
I was meditating on this all weekend. Watching Smerconish. Consuming other analysis. Thinking about Snowden. Thinking about Apple. Thinking about the trajectory of where we are headed.
And I realized I could not sit this one out.
So I recorded my full breakdown.
I am enclosing the video for the Marketplace of Ideas audience below.
Watch it. Push back. Challenge me. Tell me where I’m wrong.
Tomorrow is President’s Day, but I'm still going to work so you know what that means we're streaming at 8 AM as usual.
See you in the 8 AM Room.
Charles
I invite dialogue. Reply to this email, let me know your thoughts. Disagree, compliment, or insult me. All is welcomed!
No one knows anything. Keep learning. Stay curious. Never stop questioning.
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