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How Tope Awotona Built a $3 Billion Company After a 3-time Failure

Tope Awotona is the CEO and founder of the $3 billion company, Calendly, a modern scheduling tool for high-performing teams and individuals that want to accelerate their business growth. 

The scheduling platform, which was founded in 2013, has gained over 10 million users under Tope’s strategic management. 

The vision for Calendly began when Tope wasted the whole day going back and forth over email, trying to plan meetings. 

This was the fuel for him to begin looking for a tool that makes scheduling easier and eliminates the need for back-and-forth emails.  

Most of the tools he discovered were slow and clumsy. He decided to go all-in with his idea after months of research, placing every penny he had earned into this new venture.  

His wager paid off this time after three failed attempts. Tope’s company now generates about $30 million in annual revenue. 

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Early life and education 

The 40-year-old founder is a born Nigerian, brought up in a middle-class family in Lagos. His mother worked at the Central Bank, while his father was a microbiologist and an entrepreneur. 

Lagos, which is Nigeria’s economic centre, is also riddled with violence. And Awotona came face-to-face with, when he witnessed his father being shot and killed in a carjacking at the age of twelve.

“There was a part of me, from a very early age, that wanted to redeem him,” he said.

 In 1996, he migrated to the United States at the age of 15. And studied computer science at the University of Georgia, before switching to business and management information, and graduating with a degree.

 “I loved coding, but it was too monotonous,” he says. “I’m probably too extroverted to be a coder.”

Becoming an Entrepreneur

Awotona got a job as a sales rep at IBM. He worked in sales, for the following seven years, selling software for tech companies, including  Perceptive Software, Dell Technologies and Vertafore, but he had always aspired to be a successful entrepreneur. Due to this budding entrepreneurial spirit, he spent his evenings and weekends trying to start a company.

Most of his idea for Calendly was sparked by his frustration as a salesman. It was difficult for him to set up meetings, it was a task that most times took dozens of emails and days to complete.

Tope’s first venture was to create a dating site after reading an article on PlentyofFish, he soon recognised, however, that he lacked the necessary finances and abilities, and hence the venture was aborted.

His second business venture was an e-commerce site that sold projectors. However, he didn’t sell many, and the profit margins were poor. In addition, he was uninterested in projectors. 

His third venture was a grill-selling e-commerce site. However, he was confronted with the same issues. He also lacked enthusiasm for that line of work.  

Tope soon realised that he was only thinking about strategies for businesses to make money. He told himself that unless he concentrated on a problem he was enthusiastic about fixing, he would fail. 

He had to wait another year before he discovered the problem. He remembered in the past that he wasted a lot of time using email to plan meetings. This began his search for the right scheduling tool. 

The beginning of Calendly 

In 2013, Tope founded Calendly in Atlanta Tech Village, a coworking space for entrepreneurs. The company, however, no longer has any physical offices.

He dipped into his retirement savings and maxed out his credit cards to fund it.

Awotona hired the Ukrainian firm Railsware for programming assistance, and eight years ago, was in Kyiv as rioters fought government forces in the streets. 

He had a marketable product by late 2013, but no funds. Then a half-million-dollar seed investment led by Cummings came to the rescue.

The platform raised $350 million in capital last year from OpenView Venture Partners and Iconiq Capital, valuing the company at $3 billion. 

Awotona’s majority holding is worth at least $1.4 billion. Along with David Steward, the 70-year-old founder of Missouri-based IT company World Wide Technology. Awotona is one of just two Black IT billionaires in the United States.

Individual users can use Calendly for free, while businesses normally pay $25 per user every month.

In 2021, he won the Most Admired CEO Award from the Atlanta Business Chronicle, as well as the Comparably Best CEOs Award in 2019.

Tope Awotona prospects 

Awotona is now expanding beyond meeting scheduling to include tools that assist recruiters, salesmen, and other white-collar workers in managing meetings both before and after they take place. 

This entails assigning meetings to the appropriate individual at a major corporation, including essential information, such as agendas and budgets, in the invitation itself to streamline the meeting. 

It also enables tracking results via integration with productivity applications like Salesforce.

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