1 Sep 2026
Citation Bureau
Vol. I
No. 300

AI models cannot yet reliably identify which subset of their outputs is wrong, creating a trust gap that limits enterprise deployment.

The case

Fewer than 10% of enterprises have successfully deployed an agentic application.

“It may be that less than 10% of the enterprise has even deployed an agentic application successfully.”
Harry Stebbings · 13 Aug 2026

It takes approximately three supervised deals of hand-holding before an AI agent can be trusted to handle finance tasks autonomously.

“For the first three deals I think it took it about three deals to like okay fourth deal let's see what you So it's going to take some handholding.”
Jason Lemkin · 24 Jul 2026

The pushback

Harry Stebbings's fund fully delegates investment prioritization trust to an AI ranking system.

“We actually fully delegate trust of prioritization to the AI ranking system.”
Harry Stebbings · 15 Aug 2026

Topics

AI ReliabilityAI TrustEnterprise AI Adoption

Citation Bureau · compiled from attributed public discussion. Last updated 2026-08-24.