The Software Your Company Rents Is About to Be Built In-House

Enterprise software is about to change hands. In this episode of Capital & Coast, Wade Wyant argues that the tools companies have rented for a decade are being rebuilt in-house — and that the winners won't be the platforms, they'll be the operators who teach AI to think the way their business already does. Wade is the founder and CEO of Redegades.ai, which builds private AI environments for executive teams. Before that he grew ITS Partners from five employees to around eighty and roughly $36M in revenue, making the Inc. 5000 six years running. He's a certified Scaling Up coach and the author of Wake-Up Call. We get into why leadership teams making decisions from separate AI conversations is a governance problem nobody has named yet, what he calls "hand of God" data — the company positions his system will not override even when the CEO contradicts them — and the night he fed a wall of workshop sticky notes into AI and came back with a number forty executives in the room had missed. Also covered: why software developers are suddenly in demand again but inside companies rather than at vendors, how family offices and private equity firms are spinning up private models to underwrite acquisitions, and why he thinks AI regulation is coming whether operators want it or not. Chapters 00:00 Intro 08:11 Why one connection beats a thousand logins 13:25 The origin story: Dungeons & Dragons and duplicating the CEO 22:51 "Hand of God" data — the rules AI can't overrule 28:24 Why software is moving back in-house 36:48 Lazy humans, checklists and AI regulation 39:41 The sticky notes that found what forty executives missed 46:07 How family offices are underwriting deals with private AI Guest Wade Wyant — redegades.ai · wadewyant.com · linkedin.com/in/wadewyant Capital & Coast capitalcoastmedia.com #AIStrategy #EnterpriseAI #Leadership