Ted Sullivan, co-founder and CEO of Rollout, joins John Stanton of Trilogy Equity Partners to talk about his entrepreneurial journey, from his early days in professional baseball, to founding GameChanger, to now building Rollout, an AI-powered assistant for police officers. Ted shares how a cold LinkedIn message from a deputy police chief sparked the idea for the company and what he learned from riding along with patrol officers. They also discuss building with AI, staying close to customers, and understanding the problem before building the solution.
- (00:23) - Introduction and Ted’s background in baseball and entrepreneurship
(02:00) - Ted’s journey from minor league baseball to founding Head First(03:44) - Attending business school and shifting to a tech career(06:16) - Starting Game Changer and solving youth sports problems(10:14) - The founding team and early development of Game Changer(14:21) - Fundraising challenges and persistence in startup growth(18:26) - Industry challenges: fragmentation, seasonality, and churn(20:51) - Selling Game Changer to Dick’s Sporting Goods(23:26) - Ted’s new venture: AI in law enforcement and police work(28:01) - The role of AI in modern product development(30:20) - Common mistakes founders make and lessons learned(31:07) - Influences, mentors, and the importance of grit(34:02) - Books and resources Ted is currently reading(34:50) - Predictions for the World Series and sports analytics(35:15) - Closing remarks and future plans