Kevin Ryan Inc.

The case focuses on the hiring process for a CEO. Kevin Ryan had a solid trajectory as a serial entrepreneur of well-known ventures like Gilt Group, DoubleClick, Business Insider, among others. Ryan tended to involve himself in all aspects of his ventures: ideation, hiring/ managing initial teams, providing seed funding, and finding a CEO to scale the business. Over the years, Ryan refined his process of identifying the most appropriate person to serve as CEO, whom he bestowed with a co-founder title. He often made unconventional choices – but always trusted his instinct. Ryan believed that execution was more important than the idea, and talent determined the efficacy of execution.
The case delves into Ryan’s most recent company Truebird – an innovative, automated coffee café concept. In 2018, Truebird was at the stage at which Ryan typically hired a CEO. The case ends with Ryan mulling over how he should make the choice between the two candidates, and whether the timing was right for the candidates – and for Truebird. Hiring the wrong CEO was a high-risk proposition, and one that Ryan definitely wanted to avoid.