← Back to all posts

Overfitting in Tech and Life: Why I Pitch Cold to Stay Grounded

I was sipping my cup of cacao this morning, skimming through some LLM responses, when I caught that familiar whiff of overfitting. You know, when you’ve been working with these models for a while, and they start sounding like a “Yes Man”—just parroting back your own patterns, stroking your ego with every word. I’ve seen this phenomenon plenty of times before, whether I was training regression models at Edmodo to spot patterns in great lesson plans, calculating expected rental yields and sales prices for RentalNerd, or tweaking Edgar’s AI-driven swing trading algorithm. Overfitting creeps in, and suddenly you’re wrestling with false positives and negatives because the model’s too tuned to your quirks.

Here’s the thing that struck me—humans fall into the same trap. Hang out in an echo chamber, surrounded by folks who think just like you, and you start losing touch with the broader reality. It’s easy to do, especially in the Web3 and tech space where I spend a lot of my time. You can cozy up in tech hubs with the tech bros, buzzing about ideas that all sound the same. It feels good, but it’s a bubble. That’s why I’ve got a soft spot for democracy, messy as it is. Even the most obnoxious person from your point of view gets a channel to speak up, to vote. It’s a forced reality check, a way to break the echo chamber before it hardens around you.

So how do I keep myself from overfitting—whether to AI models or my own biases? For me, it’s all about stepping out of the comfort zone and into the raw, unfiltered world. Let me walk you through what that looks like:

Key observation: Marketing—and honestly, understanding people—is a never-ending process. The market shifts, tastes change, and you’ve got to keep up. AI can handle the automation, the backend plumbing, no problem. But deciphering the zeitgeist, feeling the pulse of what people want? That’s always going to be a human thing. From my parents’ stall to Web3 projects, it’s end-to-end, a loop of pitching, listening, and adapting.

Reflections for the day: I’m starting to think that no matter how much tech I lean on, I can’t skip the human part—getting out there, pitching cold, facing rejection or surprise. It’s what keeps me grounded. So, what about you? How do you break out of your own echo chambers—tech or otherwise? Do you have a way to test your ideas against the real world, or are you cozy in the bubble? And with AI taking over more tasks, how do you stay connected to the human feedback that matters? I’d love to hear your take.