From Dot-Com Crash to AI Boom: Lessons From 30 Years Online with David Cost

What happens when you put a 30-year tech pioneer in a room with someone building AI for the next 30?In this episode of Creative Got Me, I sit down with David Cost, VP of Digital & Ecommerce at Rainbow Shops and former co-founder of one of the internet’s first price comparison sites, PriceSCAN.com. David has quietly been at the front of every major tech wave so far: personal computing, the early web, mobile, and now AI. He’s seen the dot-com bubble burst, watched Google out-compete his startup, and then turned all of that scar tissue into a playbook for modern retail.We get into:• How a tiny 3-person dev team at Rainbow makes tech bets that let them compete with giants like Walmart• Why the iPhone, not the browser, was the real “great equalizer” for e-commerce• What he learned trying (and failing) to use AI to replace people, and why using it to assist people was a home run• The first time he saw “real” personalization work at scale, sending 100,000 unique SMS messages instead of one mass blast• How he thinks about risk, experiments, and knowing when to kill an idea without killing your appetite for trying againIf you’re a founder, marketer, or operator trying to make sense of AI without losing your mind (or your job), this conversation will calm you down and challenge you at the same time.Listen in to learn how to treat AI like the next Excel: not a threat, but the tool that quietly separates the people who stay relevant from the people who get left behind.