Zendesk CEO Rich, developing basketball AI app, confirms recommendation and security challenges

Zendesk CEO Tom Eggemeier and his son Will Eggemeier built Underdog AI, a college basketball recruiting app that helps teams find players in the NCAA transfer portal and aims to narrow the resource gap between well-funded programs and smaller schools. The project surfaced quality and security issues: the founders had to revisit the app's recommendation quality and its security and API design, and Fortune reported that the details of specific features and whether the app will launch were not disclosed. Eggemeier contributed to the app's interface design, and the pair leaned on AI-generated code in a "vibe coding" approach. The episode matters as a case study in how quickly AI-assisted development can produce a working product while leaving recommendation quality and security as the harder problems to solve. What to watch next is whether Underdog AI ships publicly and how its recommendations and API safeguards hold up.