Nigerian-born Tope Awotona poured his life savings into a software company, he’s now one of America’s richest immigrants

Tope Awotona, the 40-year-old Nigerian founder and managing director of Calendly, leans back in his chair and lets out a big laugh.

“You call it a message, I call it the truth,” he says, clapping his hands on the table, reports Forbes magazine in its April/May 2022 issue. The truth, according to Awotona, is that everyone world needs Calendly, their scheduling software, to lead a better, more productive and happier work life.

Nine years ago, Awotona started Calendly, pouring his $200,000 savings into it, and then quit his job as a software salesman for EMC.
Today, the company has 10 million users and counts Lyft,, Indiana University and La-Z-Boy among its customers. Last year, revenue topped $100 million, double what they booked the year before. It could double again this year.
The company, which was founded in Atlanta but no longer has physical offices, has been profitable since 2016. Last year it raised $350 million in funding from OpenView Venture Partners and Iconiq Capital at a price that values ​​the company at $3 billion.
That means Awotona’s majority stake is worth at least $1.4 billion, after the 10% discount that Forbes applies to shares of all private companies. Awotona is one of only two black tech billionaires in the United States, along with David Steward, the 70-year-old founder of Missouri-based IT provider World Wide Technology.
“Tope could be the most successful African-American tech entrepreneur of his generation,” says David Cummings, founder of Atlanta Ventures, who led a $550,000 seed investment in Calendly seven years ago.

Calendly does not have the scheduling activity for itself. Square, Microsoft and Zurich-based Doodle offer competing products. But Calendly has gained traction with its sleek, user-friendly design and freemium model that helps it win paying customers without marketing.

Awotona now goes beyond meeting scheduling to create tools that help recruiters, salespeople, and other white-collar workers manage those meetings before and after they happen. This means routing meetings to the right person at a large company and adding the relevant documents, such as agendas and budgets, that are needed to make the meeting run more smoothly in the invitation itself.
It also includes integration with productivity tools like Salesforce to track results. Others may view scheduling meetings as a chore, but Awotona sees it as the key to making connections to everything going on within an organization. This expanded view allows him to speculate that the global market in which Calendly sells is potentially worth $20 billion.

“In my life, I’ve benefited from not following conventional wisdom,” says Awotona. “It benefited me personally, and I think it benefited the business.”

Awotona was born in Lagos, Nigeria to a middle class family. His father was a microbiologist and entrepreneur; his mother worked at the central bank.
Lagos, a city of 15 million people, is economically vibrant but dangerous. When Awotona was 12, he witnessed his father being shot and killed in a carjacking. “There was a part of me, from a very young age, that wanted to redeem it,” he once said.
In 1996, when he was 15, he moved with his family to Atlanta. He studied computer science at the University of Georgia, then moved into business and management information.
“I loved coding, but it was too monotonous,” he says. “I’m probably too outgoing to be a coder.”

Instead, it sold software for tech companies including Perceptive Software, Vertafore and EMC (since acquired by Dell). He also founded a few businesses on the side: a dating site, a business that sold projectors, and another that sold garden tools. All three were flops.

His idea for Calendly was different in that it was sparked by his own frustration as a salesperson setting up meetings, a task that sometimes took dozens of emails and days to delay. “The obvious idea for me was that the planning is broken,” he says.
In 2013, he launched Calendly from Atlanta Tech Village, a coworking space for entrepreneurs. To fund it, he plundered his 401(k) and maxed out his credit cards.
“It could have gone very wrong,” he says. “With my previous ventures, I hedged my bets a bit and gave myself a way out. With Calendly, I flew into a war zone and invested every penny I had. If you want to do something, you have to go all out. »
For programming assistance, he contracted with the Ukrainian company Railsware. Awotona was in Kyiv eight years ago as protesters battled government forces in the streets. Now, in the midst of the war, Calendly has helped relocate its 10 Ukraine-based contract developers to Railsware and provided financial support to them and their families.

By the end of 2013, Awotona had a viable product, but there was no money left. Start-up investors, led by Cummings, came to the rescue with a half-million dollar injection. Calendly is free for individual users, but typically costs businesses $25 per user per month. “Employees are singing the praises of our product to their superiors and it’s bubbling,” says Awotona. “It’s the Trojan horse of how we get into business.”
Business customers can set up custom landing pages, route meetings to specific groups of people, and connect their Calendly software to other tools, such as Salesforce, Stripe, Zoom, and Hubspot.
Large customers, which Calendly defines as those who pay more than $100,000 per year, have increased tenfold over the past 12 months as Calendly has strengthened its internal sales team. Publicly-listed car-buying site CarGurus, for example, has scheduled some 2,000 sales meetings with its dealers through Calendly since listing last May. This saved employees 500 hours of time, says Michael Riley, CarGurus’ senior digital strategist, who led the Calendly rollout.
Last June, US Foods, a large food supplier based outside of Chicago, rolled out Calendly to 100 people who work with independent restaurants, mostly mom-and-pop shops.
The agreement allowed US Foods to implement customized templates for meetings, in English and Spanish, and incorporate new sales and other results into its strategic planning.
“That visibility was a huge selling point for signing a corporate agreement with Calendly,” says David Eschler, vice president of restaurant operations at US Foods. For its enterprise customers, Awotona says, the cost of Calendly is more than offset by the increases in productivity.

Calendly’s power dynamics can be complicated – who invites, who accepts – especially for professions, like venture capital, where this sort of thing really matters. Awotona, who says that hasn’t been a problem for the typical recruiter or salesperson, watched in amazement as his company became the focus of a Twitter war this winter.
Sam Lessin, a VC at Slow Ventures, tweeted his hatred of Calendly on Jan. 26, calling it “the most raw/naked display of social capital dynamics in business.”

“Who hurt you Sam,” fired back Dustin Moskovitz, the billionaire co-founder of Facebook whose project manager company, Asana, is a Calendly client. Added VC Marc Andreessen (net worth $1.7 billion) in a since-deleted tweet: “Notice effective immediately: Anyone disregarding my Calendly links will be banned from raising venture capital in Silicon Valley. “

Awotona says the kerfuffle has led to tens of thousands of new users signing up. “Our marketing team spent a lot of time thinking about how to get Calendly talked about this year. Little did we know the easiest way was to post tweets,” he says. “We couldn’t have plan better.”

Now Awotona, which took the company completely away from 424 people last summer, is planning more features to push Calendly further into what needs to happen before meetings (like having candidate resumes attached to meeting calendar invites). recruiters) and after them (such as analytical augmentation). He also plans international expansion, convinced that the pain of planning is felt in all geographies and in all languages.

“The ability to make each meeting effective and achieve its stated purpose is what we’re looking for,” says Awotona, who admits to spending 25 hours in meetings in an average week. “We see planning as an opportunity to prepare the meeting for success: the way you plan the meeting, the simplified preparation and the follow-up. This is our big vision.

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