Meet the unicorn founder that braved war zones and missed meetings to make his mark on the startup world

November 20, 2020, 12:04 AM UTC

Tope Awotona didn’t intend to get his startup off the ground in the middle of a war zone.

It was February 2014. Ukraine’s capital was engulfed in fire as anti-government protesters armed with molotov cocktails battled against gun-touting police forces. What had started as a peaceful movement against President Viktor Yanukovych and his decision to forego a trade deal with the European Union had devolved into a bloody state of emergency that would claim the lives of dozens in just days.

Most were packing their bags and flying out of the city. But Awotona’s thoughts veered back and forth from determined—to desperate. He had done something perilous and uncommon even in the world of venture capital. The now 39-year-old had poured every single penny in his own wallet and more into his startup idea, quitting a stable job in the sales department of cloud services company Dell EMC, emptying out his retirement, maxing out credit cards, and taking out expensive small-business loans to found a company that had yet to post any revenue. And he was no software engineer: He needed a business in Kiev to help him build out the tech behind his scheduling software company dubbed Calendly.

Luke Beard—Courtesy od Calendly

So shaking off multiple warnings from friends and family, he flew into Kiev that month. He had been there twice before for the same reason—though it was his first time flying in as international news media covered the growing violence and death tolls.

“I was scared,” he says, recalling the sounds of explosion and chaos barging into the confines of his hotel room in Kiev, a mile or two miles from the center of the riots where protestors at one point set up a ring of fire to ward off police officers. “But Calendly was my life. I felt like I had no option.”

If Calendly would be built by a company in the Ukraine, Awotona was determined to see with his own eyes whether the country was stable enough for a partnership to last. So he kept his head down, traveling only between his hotel room and the company’s offices to build up the app with the Ukraine-based company. Not long after he left the country, protestors stormed Yanukovych’s palace. 

“Looking back, it was probably stupid for me to go,” Awotona says, recalling that five months later, a Malaysian passenger flight was mistakenly shot down over eastern Ukraine. 

But it was also this single-mindedness that has helped fuel Calendly’s remarkable rise. Largely eschewing venture money, Calendly, founded in 2013, has primarily bootstrapped itself to profitability. Set to post nearly $70 million in annual recurring revenue this year, over double its figure from the year prior, it now has no shortage of venture capital and growth equity investors nipping at its heels. (Storied firms including Accel, Iconiq, and Sequoia are among the names that have courted the company, sources tell Fortune. The three firms declined to comment for this story).

“I think everyone wants to invest,” says Mercedes Bent, partner at Lightspeed Ventures. In 2020, having raised just $550,000 from investors such as Atlanta Ventures in total since its founding since 2013, some of Calendly’s would-be suitors have casually valued the company “well north” of $1 billion, says Awotona. While Calendly has not consummated a deal that values it at over that figure, “it is very much a unicorn.” Indeed, as this story published, sources tell Fortune that the company has engaged in conversations that value it around $3 billion and would provide liquidity to existing shareholders.

But while some 240 companies in the U.S. are unicorns, according to CBInsights, a number in that neighborhood would make Awotona a rarity on another front: Compass, a real estate brokerage last valued at $6.4 billion, and Zume, a producer of compostable packaging last valued at about $2 billion before the pandemic hit are among the only others who have Black founders.

It’s not a status Awotona would’ve been familiar with in his early days, when even getting a meeting with an investor was a struggle. While in Kiev, a potential investor in North Carolina bailed on a planned 2 a.m. video call

It was fate that the investor in North Carolina was unable to keep his appointment. Scheduling is after all, Calendly’s business. Capitalizing on the irritations of agreeing on a time to visit the stylist or meet a school teacher, the company has attracted some 5 million monthly active users, including users at Linkedin and Zendesk who may use the tool to say schedule a sales call or interview a new hire. While a single meeting can take multiple back-and-forths via email, Calendly shows only the available time slots of a user—bypassing any need for a lengthy email exchange. Ideally, a time could be agreed upon with one click. Boom: The slot is blocked off in Google Calendar and Outlook too.

Awotona was by no means the first person to come up with the idea of scheduling software—it’s part of the reason investors stayed away from the company in its early days. But Calendly took off because it was designed like a consumer product, inspired by Awotona’s frustrations trying to schedule a demo call with clients while at various tech companies including Dell EMC. And it had a natural potential for virality: Calendly’s most basic tier is free. But to use it, consumers have to share their Calendly-branded schedule with friends. And if those friends like the product, they’ll sign up and maybe even pay for their businesses to use it too. This kind of word-of-mouth helped marketing costs at the company low.

“Scheduling tools at the time were focused on lots of bells and whistles, but Calendly provided an Instagram-like experience for a business tool,” says Blake Bartlett, a partner at Openview Venture Partners who invested in 2017. “And it was viral.”

Awotona now credits that early lack of cash that as being a huge benefit to his business model. Calendly’s base version is indeed completely free—but that was in part because at inception, Awotona didn’t have the money to build a payments rail for the project. The lack of cash, “forced me to double down,” Awotona says, dressed in a black, but cheery Calendly shirt from his home office overlooking the verdant Atlanta BeltLine, an African mask acquired from Room and Board hanging on the wall across his desk while a far more genuine early 20th century Ghanan shrine figure sits serenely on a sideboard. An evergreen plant—an idea from his fiancé who was also introduced through a Calendly client—peeks out from the edges of our Zoom call from its white planter.

A different type of founder

In some ways, Awotona fits the quintessential founder mold: Yes, he did spend an inordinate amount of time designing and picking out shirts with his company’s logo. Yes, he meditates. He is also a former whiz kid who graduated high school two years early and earned admission to a U.S. university at the tender age of 15. He would’ve gone, too, had his mother not worried over his ability to adjust to such a rapid change, pushing him to take on two more years of high school. And like many founders, his early professional start was bred in tech companies: First at IBM, then at various sales roles at Perceptive Software, Vertafore, then Dell EMC. And in the final check mark of the founder bingo board: He has built startups before Calendly—though ones that he admits were less than groundbreaking. His first foray was a dating website, after he read that the founder of Plenty of Fish made $10 million a year working 10 hours a week in a New York Times piece. Another, called ProjectorSpot, sold projectors, while yet another, YardSteals, was a platform for home and yard equipment. 

But the parallels diverge wildly from there. First, he’s not in Silicon Valley—his company sits in Atlanta, Ga. And Awotona spent his early years as the second youngest in a family of seven in a lower upper class neighborhood of Lagos, Nigeria. When he was 12, a group of men followed Awotona’s father home and demanded access to his car. His father threw them the keys. They shot him anyway, and Awotona saw the whole thing. While he didn’t know it at the time, the incident left him with post traumatic stress disorder. The insomnia lasts to this day.

When asked if his skin color may have contributed to his early struggles to raise venture capital funding, Awotona is deliberate with his words, and doesn’t make it simple. He was never explicitly denied funding on the basis of his skin color, nor does he recall any veiled insults—and, he adds, trying to fundraise for a company that has $200,000 in revenue is never easy, especially in the Southeast. But how deeply rooted prejudices might stealthily infiltrate an investors thinking is not something he, nor any technology currently on the market, can quantify. 

There were other tortuous moments in the company’s founding too: In late 2014, Calendly decided to add a premium paying version—a decision that users cursed out in app stores, even if they eventually stuck around. Around the same time, his first Chief Technology Officer quit, unexpectedly, during a disagreement about strategy. “Those were the moments I felt like the whole thing could fall apart,” he says. Funnily enough, six years later, he can’t remember what exactly the disagreement was about. “You become more resilient in some ways to set backs. The things that seem so scary at the time seem silly now.” 

Certainly the Awotona back then would’ve been ill-equipped to handle scaling Calendly. The company has recently faced a swath of exits as its scaled, adding positions such as Chief Financial Officer and Chief Marketing Officer for the first time while others have left for different ambitions or to be based closer to home rather than Atlanta. Oji Udezue, its vice president of product, was based out of Austin and left earlier this year out of a desire to find a job closer to home. The head of revenue, David Rostan, left to start his own business in New York, his home base. And the company’s former head of business operations, Brent Chudoba, had ambitions to run a company as a CEO and moved onto Biteable, sources say. The three declined to comment for this article.

The pressures don’t stop there: Other companies have also caught onto the benefits of Calendly’s scheduling model, with Square, which markets to small businesses, also now also offering scheduling tools not unlike that of Calendly’s. Zurich-based Doodle has also recently gained traction. To stay ahead, Awotona’s mind is on making Calendly more intuitive for its users, using data to determine for example which potential clients should be prioritized for a sale, or perhaps one day automatically suggesting the best times for the involved parties. And the question that everyone inevitably asks is, will Microsoft or Google jump into the fray?

An eventual exit

Onlookers may also draw comparisons between Awotona’s business and that of Mailchimp’s, another Atlanta-based business that was entirely bootstrapped into unicorn status. 

As a matter of fact, the heads of the two companies do know each other, meeting on occasion for coffee before the pandemic hit after being paired together on a Inc magazine segment on startup mentoring (Mailchimp CEO Ben Chestnut describes Awotona as a “thoughtful and quiet guy, humble and a little secretive—I don’t think intentionally. He reminds me of me.”). 

Mailchimp can in theory stay private forever—the CEO has taken no outside money and arranged a profit-sharing agreement with employees over a stock-based compensation, but Awotona has given employees stock. Which means eventually, he will have to accept more outside investors, though he is hoping it is one that won’t involve a change in control.

“[An IPO] is certainly a strong option I am considering. But keep in mind that the private markets are really really robust these days, so some investors really just want to participate in the liquidity event. So employees can sell their shares, but I as a majority shareholder don’t need to sell my stake in a transaction like that,” he says. “I’m focused on building Calendly into a massive standalone business.”

As for what keeps him going these days?

“Initially it was for financial reasons—I literally needed to pay my bills,” he says. “But the motivations have shifted over time. As Calendly has grown, I just get a lot of people who don’t fit the mold who reach out to me, who are women, men, people of color—that have been so inspired by the story— that keeps me going through the tough days.”

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