Tech founder on building teams, loving pivots, fostering startup hustle in high schools

Scott Lingle grew up in Indianapolis with parents who were always looking for a side hustle and ways to eliminate debt. Their entrepreneurial pursuits included flipping  houses—"I lived in 20 houses growing up," Lingle says—and rehabilitating a host of other products for resale. Scott Lingle knew early on that he wanted to be in sales. After a distinguished career in the insurance industry, he took a big entrepreneurial leap. In 2015, he co-founded Remodel Health, which after initial growing pains became one of fasting-growing firms in Indianapolis throughout the early 2020s. It was ranked 13th on IBJ’s list in 2024, with a 123% increase in annual revenue between 2021 and 2023, topping out at nearly $15 million.

Lingle stepped down as CEO several years ago but stayed as board chairman while pursuing other interests and investing opportunities. Among his projects, he co-founded High School Hustle, an initiative to encourage Indianapolis students to start and grow businesses with the guidance of mentors who have done the same. It’s now in its second year and available at nearly 20 high schools. There’s a secondary goal that could be of benefit for the Indianapolis startup community: creating networks of well-established entrepreneurs who fund the students work and the younger business leaders who coach them.

In this week’s edition of the podcast, Lingle shares the lessons he learned about taking chances, building elite teams and embracing the quintessential entrepreneurial challenge of pivoting multiple times. He also lays out the strategy behind High School Hustle and its plans for national expansion.