LearnVest: Alexa von Tobel When Alexa von Tobel was just 14, her father passed away unexpectedly, leaving her mother to manage the family's finances. The tragedy made Alexa determined to understand money – and help others plan for periods of uncertainty. In her mid-twenties, she founded LearnVest, a tool that simplifies financial planning and investing. Within three years, the company was providing support to millions of customers. In 2015, she sold LearnVest for a rumored $250 million. PLUS for our postscript "How You Built That," how Dillon Hill built Gamers Gift to help bed-bound and disabled patients enjoy a wide range of places and experiences —through virtual reality.