How Rollout Is Using AI to Give Police Officers Their Time Back

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