Why Your PE AI Program Is Already Failing

Описание: I brought Shawn Olds onto the show because he has spent two decades in the trenches of AI adoption, and what he has seen should make every operating partner uncomfortable. Over 80% of AI programs inside portfolio companies fail. Not because the technology breaks. Because of the decisions made before a single tool is deployed, and because of what happens when there is no CEO in the room willing to own it.

Shawn went from the 82nd Airborne to West Point computer science to co-founding Boodle Box, and along the way he sat in front of 22 portfolio company CEOs and asked one simple question: how many of you are using this technology on a regular basis? One hand went up. That number has stayed consistent across the middle market, and Shawn breaks down exactly why, what it is costing those companies, and what the ones getting real returns are doing differently. We covered context engineering, the two reasons CEO-backed programs outperform every other approach, how PE firms can deploy data scientists during due diligence to surface hidden EBITDA before close, and a specific example from the security industry where existing unstructured data could eliminate $15 million in annual costs without buying a single new tool.

CHAPTERS

00:00 - Why most AI programs fail

01:16 - Shawn's path to PE consulting

08:28 - Why AI adoption stays low

14:33 - PE due diligence and data science

16:15 - AI gains across portfolio companies

22:49 - Where mid-market companies should start

34:17 - Real results from portfolio companies

39:56 - How to reach Shawn Olds

GUEST

Shawn Olds is an AI strategist and co-founder of Boodle Box, a platform that consolidates multiple AI models into one collaborative workspace for companies. He studied computer science at West Point, served in the U.S. Army's 82nd Airborne, and has spent two decades building technology companies across the United States, the Middle East, and Africa. He now works directly with private equity firms and portfolio company CEOs to identify where AI can produce documented, measurable business results.

Find Shawn on LinkedIn:   / shawnolds  

TOOLS AND COMPANIES MENTIONED

Boodle Box

NotebookLM by Google: https://notebooklm.google.com

ChatGPT: https://chat.openai.com

Claude by Anthropic: https://claude.ai

Gemini by Google: https://gemini.google.com

Perplexity AI: https://www.perplexity.ai

McKinsey, Bain, BCG, PwC, MIT, 7-Eleven, Hire Aligned, Zero Prostate Cancer Foundation