Gordon Wintrob, Co-Founder and Chief Technology Officer at Newfront: How Shadowing Helped Me Start a Unicorn

The Blind Ambition with Jack Kelly

Gordon Wintrob, Co-Founder and Chief Technology Officer at Newfront

Gordon co-founded Newfront, an insurance-technology startup and brokerage firm last publicly valued at $2.2 billion, but he did not start his career in insurance. We dig into his career from his days in college and how he pivoted from his electrical engineering and computer science studies to investment banking and then to the world of startups.

Gordon credits shadowing for a lot of his success. We explore how he and his co-founder got the idea for Newfront, how they found an insurance broker to let them observe his work and the aha moments along the way. He even shares some of the startup ideas they left behind, how shadowing is still part of Newfront's culture today and a unique part of the startup's job interviews.

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