Why Your PE AI Program Is Already Failing

Episode notes

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.

• Why Hiring Works More Like Sales Than HR68 / 100
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• What PE Buyers Find When They Actually Look at Your Data
• Is your Data telling you the right story?