T ope Awotona is a self-made Nigerian-American billionaire and the founder and CEO of Calendly, a popular and widely used scheduling automation software. Born in Lagos, Nigeria, he witnessed the tragic death of his father as a child. He later immigrated to the United States for college. After a successful career in software sales for companies like EMC, he became deeply frustrated with the inefficient back-and-forth emails required to schedule meetings. This frustration became the inspiration for his own business.

In 2013, he founded Calendly, bootstrapping the company by investing his life savings of $200,000. The software's simple, freemium model, which allows users to share a link that shows their calendar availability and lets others book a time, made it a viral hit, spreading rapidly through word-of-mouth. The company's exponential growth, particularly during the shift to remote work, attracted a major funding round in 2021 that valued it at over $3 billion, making Awotona one of the wealthiest Black tech founders in the U.S.