What Actually Breaks Private Equity Portfolio Companies

Private Equity Data Guy · Sep 24, 2026 · 51m · transcript

In this episode I sit down with Rich Kershaw, a technology due diligence specialist who has looked at over 250 companies for private equity and venture capital investors. We talk about why the technology itself is rarely the real problem inside a portfolio company. Rich explains that the org chart exposes decision making gaps that technical documents alone will not show you.

This conversation gets into where large language models help and where they fall short. Rich explains why he treats AI like a smart but inexperienced intern who still needs clear direction. He shares what he is building…