From Rags to Riches: How Nigerian-Born Tope Awotona Became One of America’s Richest and Most Savvy Immigrants with a 1.4B Networth

From Rags to Riches: How Nigerian-Born Tope Awotona Became One of America’s Richest and Most Savvy Immigrants with a 1.4B Networth

Profile photo of Tope Awotona

Calendly, a scheduling platform for the modern man, has solved the logistical nightmare that setting up a meeting can be.

The Calendly website advertises it as something that takes, “the busywork of scheduling off your to-do list so you can get more done. Thousands of teams across the globe use Calendly to make millions of 1-click meetings every week. Coordinate, connect, and nurture relationships all in one meeting lifecycle platform.” But, essentially, Calendly is the perfect virtual assistant. Need reminder emails or thank you notes? Calendly has them prepped and ready to go.

Today, the company has a $3B net worth and hosts a whopping 10 million user interface. Included in its customer base are countless household names like Lyft, La-Z-Boy, and Nevertheless, this multimillionaire dollar platform like all great enterprises started off as an idea, and the man who thought of it was then 28-year old Tope Awotona.

Awotona, now worth $1.4B, had a modest upbringing.

He was born into a middle-class family in Lagos, Nigeria. His father was a microbiologist and entrepreneur, and his mother worked at the central bank. Despite being one of Nigeria’s smallest states, Lagos has one of the highest urban populations (27.4% of the national estimate). And in such a densely populated city, his family came across a few unsavory types, one of which ended up taking Awotona’s father away from him at the young age of 12. “There was a part of me, from a very early age, that wanted to redeem him,” he said.

Moving to the states, helped him do just that. In 1996, at the age of 15, he and his family moved to Atlanta. After graduating high school, he began studying Business and Management Information at the University of Georgia and later stepped into the professional world of entrepreneurship.

His burgeoning potential as a businessman was shown throughout his ventures selling software for tech companies, like Perceptive Software, Vertafore, and EMC (since acquired by Dell). He also built a few enterprises of his own, including his own version of and one company that sold projectors, and another that sold garden tools. And while those three ultimately failed, they brought him closer to his moneyball.

Calendly was born out of Tope Awotona’s own frustrations as a salesman trying to set up multiple meetings for buyers—a task that involved numerous setbacks and countless hours of back and forth. His feelings on the matter were clear, “The obvious idea to me was that scheduling is broken,” and in response, In 2013, he launched Calendly from Atlanta Tech Village, a coworking space for entrepreneurs.

To fund it, he poured his life savings of $200,000 and maxed out his credit cards. “It could’ve gone really badly,” he says. “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.”

However, despite overcoming one hurdle, he was not out of the woods yet. By 2013, after receiving programming help from the Ukrainian firm Railsware, he had no more cash to burn to keep the Calendly train running. David Cummings, founder of Atlanta Ventures, came to Tope Awotona’s rescue and led a $550,000 seed investment in his company.

In the world of business scheduling, Calendly is not alone. Square, Microsoft, and Zurich-based Doodle offer competing products. But Calendly has made itself unique with its user-friendly design and its freemium pricing strategy that attracts paying customers with no marketing, and its growth internationally.

Now, amid the war (which has been popularly dubbed WW3), Calendly has helped relocate its 10 Ukraine-based contract developers at Railsware and has also financially supported them and their families.

Tope Awotona is also moving towards international expansion beyond the war, recognizing that the struggle of scheduling is experienced across all countries and cultures, “The opportunity to make each meeting efficient and achieve its stated purpose is what we’re about,” says Awotona, who confesses to spending 25 hours in meetings in an average week. “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.”



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