February 27, 2026

Why Your PE AI Program Is Already Failing

40 minutes

Shawn Olds spent two decades building AI companies and advising PE firms on what actually produces returns from the technology. He went from the 82nd Airborne to West Point computer science to co-founding Boodle Box, and along the way he has worked with over 200 companies on AI adoption. The number that should make every operating partner stop: over 80% of AI programs in portfolio companies fail. Not because the technology breaks. Because of decisions made before a single tool is ever deployed.

Shawn and I covered why context engineering has replaced prompt engineering, why CEO backing is the one variable that separates companies getting real ROI from those just gaining productivity, and how PE firms can use data scientists during due diligence to surface hidden EBITDA before they close a deal. He also walked through real examples from the security industry that show how unstructured data already sitting inside a company can be turned into millions in annual savings without purchasing a single new tool.

Chapters:

00:07 - The Role of AI in Prompt Creation
02:04 - The Journey into AI Consulting
11:08 - Empowering Innovation in AI Adoption
24:14 - Harnessing AI in Business: Practical Applications
29:39 - The Role of AI in Enhancing Business Processes
37:41 - Starting with AI: Understanding the Journey

Guest Information

Shawn Olds is an AI strategist and co-founder of Boodle Box, a platform that brings multiple AI models into one collaborative workspace. He studied computer science at West Point and served in the U.S. Army's 82nd Airborne before spending two decades building technology companies across the United States, the Middle East, and Africa. He now advises PE firms and portfolio company CEOs on practical AI adoption that produces measurable business results.

Companies Mentioned