Woodrow Levin was playing fantasy football with the CEO of Draft Kings when one of his players got hurt, causing him to lose a bet. What started as a joke about buying insurance for players quickly spiraled into "what if I can offer insurance/extended warranties on all online products?" It was on this premise that Extend, an extended warranty company that works with online retailers responsible for over $11B gross annual sales, was founded. The company has since raised $16M in VC funding. Extended warranties have become a big business with more than $45B a year in plans sold. Only the top 1% of merchants (Amazon, Costco, and BestBuy) offer extended warranty, leaving a massive portion of the market unable to offer their customers protection plans. By leveraging machine-learning technology and a network of top-rated insurance companies that cater to merchants of all sizes, Extend now offers a solution to the rest of the market to drive incremental bottom-line net income. But also increase overall purchase conversions, and create loyal customers with a digitally native customer experience. However, I felt compelled to find out more about the story behind Woody's tech journey and how serendipity is just as important as technology.