In 2013, Tope Awotona emptied about $200,000 of his savings to build Calendly; eight years later investors valued the company at $3 billion

When entrepreneur Tope Awotona founded Calendly in 2013, he put his financial security on the line to solve a problem he had repeatedly encountered while working in sales: the frustrating back-and-forth involved in scheduling meetings. In an interview with How I Built This, Awotona said building the initial product was expected to cost a little over $200,000, forcing him to empty his retirement account and savings, borrow money and max out his credit cards. Eight years later, a $350 million funding round valued Calendly at more than $3 billion, according to TechCrunch. The company now says its platform is used by more than 50 million people.Awotona, who grew up in Lagos, Nigeria, before moving to the United States as a teenager, had worked in enterprise software sales at companies including IBM and Dell. He was familiar with the process of arranging meetings and the time lost to repeated emails proposing dates, checking availability and confirming appointments. Calendly emerged from his frustration with that routine, with the aim of making it easier for people to find a mutually convenient time without lengthy exchanges.The idea was straightforward: instead of negotiating a meeting...