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AI is moving so fast that it’s hard to tell what’s hype, what’s helpful, and what’s genuinely risky. That’s why we brought in Eric Simons, a serial entrepreneur who helped pioneer affiliate marketing and has spent more than 25 years working with artificial intelligence and automation. He’s seen one world-changing wave up close already, and he believes the AI wave looks a lot like the early internet, only faster and more personal.

We talk through the early days when “search” meant Yahoo and Excite, when websites had traffic but no monetization, and when automation was the unfair advantage. Eric shares how affiliate programs worked before today’s ad platforms, how scaling SEO became a systems problem, and the wild story of accidentally becoming the top online source for caskets overnight. Along the way, we dig into what those experiences teach any entrepreneur: distribution matters, margins can lie, and logistics can make or break a business.

Then we bring it to the present: modern AI, large language models, custom GPTs, and agentic AI that can actually do work across tools like email and calendars. We also don’t dodge the uncomfortable parts like deepfakes, voice cloning, scams, and what happens when AI becomes “too agreeable.” If you’re a designer, creative, or business owner looking for practical AI use cases, clearer language, and smarter guardrails, this conversation gives you a grounded starting point.

Subscribe, share this with a friend who’s curious (or anxious) about AI, and leave a review. What’s one task you want AI to take off your plate next?

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