Steven Paul Matsumoto, President, Stigmare | The Jeff Crilley Show

A prospect fed three roofing bids into Claude, and by 9 AM the AI had already picked the winner. That single story frames the whole conversation Jeff Crilley has with Steven Paul Matsumoto, president of Stigmare—a marketing strategist and serial entrepreneur who doesn't just theorize about growing businesses but has the receipts. Steven spent years as a senior leader for fixed operations at Lithia Motors before launching Stigmare, which offers fractional CMO services, AI search optimization, and digital PR for small and mid-size companies. He also took Juno's Liquor from $8,000 in monthly sales to over $1 million in annual revenue across three locations, then exited with a 3x return. In this episode:– Why 25–34% of searches are moving to AI chat platforms and what that means for businesses still paying for traditional SEO– The roofing bid story: how Claude generated technical questions that decided a five-figure contract before the contractors could respond– How third-party media coverage (press releases in Yahoo Finance, USA Today, Fox Business) acts as a trust signal that AI models reward– The referral trap: why relying solely on word-of-mouth creates a roller-coaster revenue cycle– Steven's nomination for Entrepreneur Magazine's Entrepreneur of Impact award, supporting Gen Youth and Toys for Tots https://stigmar.com