Calendly: Tope Awotona (2020)

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 reportedly doing over $100 million in revenue.

This episode was produced by Rachel Faulkner-White, with music by Ramtin Arablouei

Edited by Neva Grant, with research help from Daryth Gayles.

You can follow HIBT on Twitter & Instagram, and email us at

See Privacy Policy at and California Privacy Notice at