When a consumer adds an AppleCare warranty to their purchase, it adds a layer of trust and protection. What if you could insure most purchases you make online? In 2019, Woody Levin co-founded Extend to modernize the warranty industry. As Covid accelerated the e-commerce, Extend's business has seen rapid growth, working with customers from Sur La Table to Peloton. Woody shares how his aha moment for Extend came from losing a fantasy football bet, why it was like to hire 350 employees in one year, and how he's used career failures as fuel.