Nine years ago, Awotona started Calendly,
pouring his life savings of $200,000 into it and later quitting his job selling
software for EMC
Awotona started the company in 2013,
putting in his $200,000 live savings in it. “It could’ve gone really badly,”
Awotona told Forbes‘ Amy Feldman. “With my previous businesses, I hedged my
bets a little bit and gave myself a way out. With Calendly I flew into a war
zone and put in every cent I had. If you’re going to do something, you have to
go all in,” he added.
Today, his majority stake is worth $1.4
billion, according to Forbes. This is after the 10% discount that Forbes
applies to shares of all private companies. This makes Awotona just one of two
Black tech billionaires in the United States.
David Cummings, founder of Atlanta
Ventures, who led a $550,000 seed investment in Calendly seven years ago,
opined that “Tope could be the most successful African-American tech
entrepreneur of his generation.”
Awotona spent the first 15 years of his
life in Nigeria, and moved to Atlanta with his family in 1996. He started out studying
computer science at the University of Georgia, then he switched to business and
management information: “I loved coding, but it was too monotonous. I’m
probably too extroverted to be a coder,” he said.
Afterwards, Awotona sold software for tech
companies before venturing into entrepreneurship: he started a dating website;
a business that sold projectors; and another business where he sold garden
tools. “All three were flops,” the Forbes report said.
The idea to start Calendly came from Awotona’s frustration trying to set up meetings as a salesman. “The obvious idea to me was that scheduling is broken,” Awotona said. He then launched the company from Atlanta Tech Village, a co-working hub for entrepreneurs. Today, the 424-person company works fully remote, a move Awotona made last summer.
Calendly is free for individual users, but
costs corporations around $25 per user per month. “Employees sing the praises
of our product to their higher-ups and it bubbles up. That’s the Trojan horse
of how we get into companies,” Awotona told Forbes.
Beyond scheduling meetings, Awotona is
adding features to help people manage meetings before and after they occur.
“The opportunity to make each meeting
efficient and achieve its stated purpose is what we’re about. We see scheduling
as an opportunity to set the meeting up for success—how you schedule the
meeting, simplified preparation and follow-up. That is our grand vision,”
Awotona said.