Tope Awotona, a Nigerian by birth. Now one of the richest immigrants in America after investing life savings in Calendly

Tope Awotona was born into a middle-class household in Lagos, Nigeria. His mother worked at the central bank and his father was a microbiologist and entrepreneur. Lagos is a 15-million-strong metropolis, which is economically dynamic.

Awotona founded Calendly nine years ago, investing his entire life savings of $200,000 and resigning his job selling software for EMC in the process.

Lyft, Ancestry.com, Indiana University, and La-Z-Boy are among the company's customers, with a total of 10 million users. Last year's revenue surpassed $100 million, more than doubling that of the previous year. It's possible that it'll double this year as well.

Calendly was founded in Atlanta and has been profitable since the year 2016. Currently, the company has no physical offices. It raised $350 million in financing last year from OpenView Venture Partners and Iconiq Capital, valuing the company at $3 billion.

Alongside David Steward, the 70-year-old founder of Missouri-based IT firm, World Wide Technology, Awotona is one of just two Black IT billionaires in the United States.

According to David Cummings, founder of Atlanta Ventures, which led a $550,000 seed investment in Calendly seven years ago “Tope could be the most successful African-American tech entrepreneur of his generation.”

Calendly isn't the only one in the scheduling game. Square, Microsoft, and Doodle, founded in Zurich, all have rival products.

Calendly, on the other hand, has gained popularity thanks to its sleek, user-friendly design and freemium strategy, which allows it to attract paying clients without any promotion.

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

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

It also enables tracking results via integrating with productivity tools like Salesforce.

While people may regard meeting scheduling as tiring, Awotona sees it as critical to connecting everything that occurs within a company. With this broad perspective, he estimates that the global market into which Calendly sells may be worth $20 billion.

According to Forbes, his majority stake is now worth $1.4 billion. This is after Forbes deducts a ten percent discount from all private company shares.

He said “In my life, I’ve benefited from not taking the conventional wisdom”... “It’s benefited me personally, and I think it has benefited the business”.

Awotona relocated to Atlanta with his family when he was 15 years old, in 1996. At the University of Georgia, he studied computer science before moving on to business and management information.

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

He worked with some tech companies like Perceptive Software, Vertafore, and EMC, selling software for these companies. He started a dating website, a projector firm, and a garden tool company on the side. All three of them were a complete failure.

The idea behind Calendly was unique in that it was inspired by his frustrations as a salesperson scheduling meetings, a task that may take dozens of emails and coupled with a lot of delays. He said “The obvious idea to me was that scheduling is broken,” 

Calendly was founded by Awotona in Atlanta Tech Village, a collaborative space for entrepreneurs, in 2013. He dipped into his retirement account and maxed up his credit cards to pay for it.

“It could’ve gone really badly,” he said. “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 contacted the Ukrainian firm Railsware for programming services. Calendly has assisted its ten Ukraine-based contract developers in relocating to Railsware and has offered financial assistance to them and their families as a result of the ongoing conflict.

Awotona had a marketable product by late 2013, but no funds. With a half-million-dollar investment, seed investors led by Cummings came to help. Individual users can use Calendly for free, while businesses normally pay $25 per user per month.

“Employees sing the praises of our product to their higher-ups and it bubbles up” he said. Also adding “that’s the Trojan horse of how we get into companies”.

Customers may create personalized landing pages, assign meetings to specific groups of employees, and integrate Calendly with other applications like Salesforce, Stripe, Zoom, and Hubspot.

Calendly's large customers, classified as those who pay over $100,000 per year, have increased tenfold in the last year as the company has ramped up its internal sales force.

Since joining Calendly in May, CarGurus, a publicly-traded vehicle purchasing website, has arranged over 2,000 sales meetings with its dealers.

According to CarGurus senior digital strategist Michael Riley, who spearheaded the Calendly implementation, this has saved employees 500 hours of time.

Calendly's power dynamics can be complex, who makes the invitation, who accepts, especially in sectors where this kind of thing is critical, such as venture capital.

Awotona, who claims that this hasn't been an issue for the average recruiter or salesperson, observed in amazement as his organization became the subject of a drag on Twitter.

According to Awotona, the uproar resulted in tens of thousands of additional people signing up.

He said “Our marketing team has spent a lot of time thinking about how to get people talking about Calendly this year. We didn’t know the easiest way was to put out some tweets”... “We couldn’t have planned it better.” He added.

The 424-person company went totally remote last summer, Awotona hopes to add further capabilities to Calendly to help with what has to happen before and after meetings.

“The opportunity to make each meeting efficient and achieve its stated purpose is what we’re about,” Awotona said. “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” he added.