Calendly: Tope Awotona

Tope Awotona, Founder of Calendly
Harry Dunkwu for NPR
Tope Awotona, Founder of Calendly

Harry Dunkwu for NPR

After emigrating from Nigeria to the US to attend college, Tope Awotona worked as a door-to-door salesman and eventually set out to become a tech entrepreneur.

He launched a series of e-commerce businesses that quickly fizzled when he realized he had no passion for them. But then he landed on an idea he was truly excited about: designing software that would minimize the hassle and headache of scheduling meetings.

In 2013, he cashed in his 401k and went into debt to build Calendly, a scheduling service expected to make about $60 million this year.