"I Just Want to Play More Golf" — Why ROI Isn't Always the Right AI Pitch What happens when you pitch a lawyer on billing 30% more hours and they say they'd rather leave early to hit the golf course? You learn that ROI isn't always the story that closes deals. James Lawler is the Managing Director of TriCoStar, an AI-powered time recording and email management platform built specifically for law firms. His company has been in legal tech for 38 years—his dad started it in the late 80s with a device called a Psion that most of us have never heard of. Today, James is doing founder-led sales into one of the most change-resistant industries out there. In this episode, we dig into what it actually takes to sell AI to buyers who are skeptical by profession. Turns out, the biggest objection isn't whether AI works—it's whether it'll catch them checking football scores. We cover: → Why privacy concerns beat performance skepticism in conservative industries → How James uses Copilot live during sales calls to translate technical answers into plain language → The difference between selling "bill more hours" vs. "get your evenings back"—same product, completely different pitch → What happens to the legal profession if firms automate paralegal work (and why apprenticeship-style contracts might make a comeback) → How to keep deals warm without filling inboxes with boilerplate when you're running founder-led sales If you're selling into traditional industries or trying to figure out how AI fits into your own sales motion, this one's worth your time. 🎧 Follow Selling AI on Apple Podcasts, Spotify, and YouTube.