Tope Awotona, the 40-year-old founder and CEO of Calendly, leans back in his chair and laughs loudly.
“You call it a message; I call it the truth,” he slaps his hands on the table. According to Awotona, everyone requires Calendly, his scheduling software, to lead better, more productive, and happier work lives.
Awotona founded Calendly nine years ago, investing his life savings of $200,000 in it and later quitting his job selling software for EMC. Today, the company has 10 million users and customers such as Lyft, Ancestry.com, Indiana University, and La-Z-Boy. Last year’s revenue surpassed $100 million, more than doubling that of the previous year. It’s possible that it’ll double again this year.
Since 2016, the company, which was founded in Atlanta but no longer has any physical offices, has been profitable. It raised $350 million in funding last year from OpenView Venture Partners and Iconiq Capital, valuing the company at $3 billion. That means Awotona’s majority stake is worth at least $1.4 billion after a 10% discount applied by Forbes to all private company shares.
Awotona, along with David Steward, the 70-year-old founder of Missouri-based IT provider World Wide Technology, is one of only two Black tech billionaires in the United States. “Tope has the potential to be the most successful African-American tech entrepreneur of his generation,” says David Cummings, founder of Atlanta Ventures, which led a $550,000 seed investment in Calendly seven years ago.
Calendly does not have a monopoly on scheduling. Square, Microsoft, and Zurich-based Doodle all provide competing services. Calendly, on the other hand, has gained traction thanks to its sleek, consumer-friendly design and its freemium model, which allows it to gain paying customers with no marketing.
Awotona is now expanding beyond meeting scheduling to develop tools to assist recruiters, salespeople, and other white-collar workers in managing meetings both before and after they occur. That entails routing meetings to the appropriate person within a large corporation and including relevant documents, such as agendas and budgets, that are required to make the meeting run more smoothly in the invitation itself.
It also entails integrating with productivity tools such as Salesforce in order to track results. Others may regard meeting scheduling as a drudgery, but Awotona sees it as critical to connecting everything that happens within an organization.
This broad perspective allows him to speculate that the global market into which Calendly is selling could be worth $20 billion.
“I’ve benefited in my life from not accepting conventional wisdom,” Awotona says. “It’s helped me personally, and I believe it’s helped the business.”
Awotona was born into a middle-class family in Lagos, Nigeria. His father was a microbiologist and business owner, and his mother worked at the central bank.
Lagos, a 15-million-person city, is economically vibrant but dangerous. Awotona was 12 years old when he witnessed his father being shot and killed during a carjacking. “From a very young age, there was a part of me that wanted to redeem him,” he once said.
He moved to Atlanta with his family when he was 15 years old, in 1996. At the University of Georgia, he majored in computer science before transferring to business and management information. “I liked coding, but it was too repetitive,” he says. “I’m probably too outgoing to be a programmer.”
Instead, he sold software to tech firms such as Perceptive Software, Vertafore, and EMC (since acquired by Dell). On the side, he started a dating website, a company that sold projectors, and another that sold garden tools. All three were failures.
