What if success in business didn’t require burning out, but instead came from building intentionally, listening deeply, and surrounding yourself with people who make you better? In this episode, Scott talks with serial entrepreneur and investor Scot Wingo: founder of five companies, three-time successful exit, and driving force behind the Triangle Tweener Fund. From growing up with a mainframe computer in his living room to leading coast-to-coast operations, Scot shares how curiosity, grit, and systems thinking have shaped his journey. He opens up about scaling from startup to $80M+, building teams of “go-to” people, and creating a personal operating rhythm that keeps life at home and work in harmony.

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About Scot Wingo:

Check out the Triangle Tweener Fund: tweenerfund.com
Explore Get Spiffy: getspiffy.com
Connect with Scot on LinkedIn: linkedin.com/in/thescotwingo/

Time Stamps:

(01:52) Growing up with a mainframe in the living room
(04:15) Founding five companies and three successful exits
(06:38) The Triangle Tweener Fund: Investing in homegrown talent
(10:22) Scaling from startup to $80M+ without burning out
(14:07) Building a team of “go-to” people
(19:34) Personal operating rhythms that keep life in balance
(25:10) Lessons from leading coast-to-coast operations
(31:46) Why listening is the ultimate leadership skill
(36:58) Balancing founder ambition with intentional growth
(43:25) What Scot’s listening to: music, podcasts, and more

Show Transcript: