Even an AI Optimist Admitted This About Shopping
A conversation on the Boss Mode podcast with David Lee
By Kate Assaraf
I went into the conversation expecting to defend something.
When you spend years building a business that doesn’t follow the rules, you get used to explaining yourself. Why no ads (yet!). Why no growth hacks. Why you would ever make it harder for someone to buy instead of easier. So sitting down with David Lee on the Boss Mode podcast, I assumed we would fall into familiar territory. He would talk about the power of AI, the speed, the scale, the inevitability of it all. And I would talk about what gets lost when everything becomes optimized.
But that’s not exactly what happened.
The truth is, I don’t have a problem with technology. I’ve spent my entire career inside it, watching marketing evolve into something sharper, faster, more precise. What I’ve struggled with is what that precision has been used for. Somewhere along the way, we stopped building relationships and started engineering outcomes. People became data points. Decisions became predictable. And commerce, which used to be something you experienced, became something that happens to you.
I told David a story during the podcast that I think a lot of people quietly recognize in their own lives. I bought something online from what looked like a small, New York-based brand. The kind of brand you want to believe in. Beautiful imagery, a couple that seemed like founders, a story that felt grounded in something real. Three weeks later, a package showed up. It wasn’t from New York. It wasn’t cotton. It wasn’t even close. It was plastic, poorly made, and impossible to return.
The frustration wasn’t just about the product. It was about the realization that I hadn’t made a clean decision. I had been guided into one. Nudged, optimized, and closed. That’s what I’ve come to call digital pollution. Not because technology is bad, but because it has removed the friction that used to hold people accountable. When you don’t have to look someone in the eye, it’s easier to get things wrong. Or worse, to get them wrong on purpose.
For a while, the conversation stayed there. On trust, on manipulation, on how easy it has become to build something that looks real but isn’t. And then David told a story that shifted everything.
He started talking about a vintage audio shop. The kind of place you don’t just pass by. You go in because you’re curious, or because someone told you to. Inside, there’s a person who knows everything. Not in the way you can look something up, but in the way that comes from years of obsession. They don’t just sell you a speaker. They tell you who made it, why it sounds the way it does, what era it came from. Sometimes they even find small things hidden inside, little artifacts left behind by the original makers.
As he told the story, I watched him change. His voice slowed down. He smiled without realizing it. He wasn’t talking about efficiency or scale anymore. He was remembering something.
I stopped him and said, “That is the feeling.”
That was the moment everything clicked for me.
Here was someone deeply invested in the future of AI, someone who understands exactly where things are going, and the thing that made him come alive wasn’t a tool or a system or a breakthrough. It was a store. A person. An interaction that couldn’t be replicated or scaled.
We talk a lot about what AI will replace. It will replace tasks, workflows, entire categories of work. It will make things faster and cheaper and more accessible. All of that is true. But sitting there in that conversation, it became clear that it also does something else. It creates contrast. The more artificial things become, the more obvious the real ones feel.
You can generate content. You can simulate a voice. You can design an experience that mimics discovery. But you can’t recreate the feeling of being known by someone who has tried everything and is willing to tell you the truth. You can’t replicate the moment when two strangers in a store start comparing notes on something they both care about. You can’t automate trust.
By the end of the podcast, we weren’t debating anymore. We were arriving at the same place from different directions. David said something that stayed with me. That as AI expands, people will crave human interaction more. Not less. More.
It’s a simple idea, but it changes how you see everything.
Because if that’s true, then the future of commerce isn’t a race toward removing friction entirely. It’s about being intentional with what we remove and what we protect. Some friction is where the good stuff lives. It’s where conversation happens. It’s where doubt turns into trust.
People often ask why I built my company the way I did. Why I push people into stores instead of keeping them online. Why I don’t make the path to purchase as smooth as possible. The answer is that I’m not just trying to sell something. I’m trying to create the conditions for that feeling we were talking about. The one that made David light up.
The moment when someone walks into a space, unsure of what they need, and leaves feeling like they were taken care of by someone who actually knows.
AI will absolutely reshape commerce. It will make it more efficient than anything we’ve seen before. But it will also make something else happen quietly in the background. It will make real experiences harder to fake and easier to recognize. And that changes what people value.
If you’re building a brand right now, that’s the question worth asking. Not how to use AI better, but what part of your business AI could never touch. What part of it has to remain human in order to mean anything.
For me, it’s that moment in a store. The conversation. The recommendation that isn’t scripted. The trust that builds without anyone tracking it.
I went into the Boss Mode podcast expecting to defend that way of thinking. I didn’t expect to find agreement. But somewhere in the middle of a conversation about the future, we both ended up in the same place.
Not rejecting technology. Not romanticizing the past.
Just recognizing something simple and easy to forget.
That even in the most advanced version of the future we can imagine, we are still going to want to be around other people.
And the places that make that possible will matter more than ever.
