Tope Awotona: The Visionary Behind Calendly’s Global Impact

Hey, hey… Welcome back to the Black Builders by Founders Connect , where we dive into the stories of people, products, and places that are transforming the way we live and work. In this issue (#2), we're shining our light on Tope Awotona.

Tope Awotona , the brain behind Calendly , has turned the mundane task of scheduling meetings into a global business revolution. This isn’t just any scheduling app; it's the go-to platform for professionals who want to close deals, recruit top talent, build relationships, and supercharge their growth without drowning in email back-and-forths. If you've ever attempted to set up a meeting with a potential partner, mentor, or anyone else, there's a high chance you've come across this amazing product.

Calendly’s sleek, user-friendly design and seamless integrations have made it an indispensable tool for millions. The platform isn’t just leading the market; it’s redefining productivity itself across a myriad of industries.

Born in Lagos, Nigeria, in 1981, young Tope's life was a mix of academic excellence and tragedy. His dad, a microbiologist, and his mom, a pharmacist, were not just nerds in lab coats. Tope recognized them as ambitious go-getters who inspired him to dream big. His mom worked for the Central Bank of Nigeria, and his dad was a serial entrepreneur.

At 12, he witnessed his father's death in a carjacking—an event that lit a fire under him to succeed. “There was a part of me, from a very early age, that wanted to redeem him,” he said in an interview.

Fast forward to 1996, and the Awotona family is jetting off to the USA. Tope dives into American life headfirst. While at the University of Georgia, Tope doesn't just hit the books. Oh no, he jumps into the deep end of sales, tackling some of the toughest salesman gigs out there. Cold calling for donations? Check. Selling alarm systems door-to-door? Double check. Talk about building character! Every rejection he got as a salesman was just preparing him for the wild world of entrepreneurship that lay ahead.

“After you get the initial shock of people saying no to you, you actually fall in love with being able to persuade people to give you their money.”

When asked if working those jobs made him resilient, he had this to say:

“I don't know that I started off being incredibly resilient. Part of what happened is this: when I worked at AT&T selling alarm systems door-to-door, it was the first job I ever had that was strictly commission-based. There was no hourly wage or anything, so you either sold and ate, or you starved. Luckily for me, the first day I started, I did really well. I ended up making $500 my first day, which is not a lot of money to most people, but as a 17- or 18-year-old college kid, it was a lot to me. Making that in a day was really exciting. That first day was a Monday, and the rest of the week, I didn't make any additional money. If the order of my success had been reversed—if I had gone the first four days without making any money—I don't know that I would have come back on the fifth day. But the fact that I saw what success could look like on the first day actually motivated me to stick with it. It began to give me resilience because I knew what the success rate was. I knew that I could go up to four or five days without doing really well and just needed one really good day to change all that around. That's when I became comfortable with betting on myself and taking risks.”

After university, Tope went full tech-bro, working sales for various companies, including Perceptive Software, Vertafore, and EMC (now part of Dell). But his entrepreneurial itch was too intense to ignore. He launched not one, not two, but THREE startups! He tried his hand at a dating site, an e-commerce site selling projectors, and another hawking garden equipment. While they all failed, they taught him a crucial lesson: to focus on solving a problem he genuinely cared about, not just chasing profits.

“I realized that to make it a really successful business, I needed to actually care about projectors. And I did not care about projectors. I'd never bought a projector myself; I'd operated a few projectors from presentations I gave. But largely, I knew very little about the problem, and I didn't care to learn more about it.”

But here's where it gets good. In 2013, Tope had his "eureka" moment while trying to schedule a meeting. The endless email back-and-forth drove him crazy, and soon enough, Calendly was born.

“So I take this sabbatical from starting businesses. And yeah, Calendly comes up. And the way it comes up is I'm looking to schedule a meeting. And I forget exactly who I'm trying to schedule a meeting with at the time. But I was trying to maybe coordinate a meeting across maybe three different companies with about 10 to 20 people, and it was just so painful.” ”…There had to be some commercially available product that I could just go sign up for or buy that would solve this. And so I wasn't looking to start a business, I was just looking to buy something, I began to investigate.”

“The other thing I thought I had was having worked at a lot of successful software companies, I actually knew what a successful software company should look like. Unlike all the other e-commerce businesses I tried to start, I didn't know anything about e-commerce, but I knew a lot about software. And I spent, at that time, about seven years working for enterprise software companies. I also felt like what was missing from the market at the time was usability. I thought a lot of the scheduling products that existed on the market at the time were clunky and difficult to use. And I thought I had a good eye for usability and design. So for all those reasons, I thought I was well positioned to create something unique and differentiated.”

In 2013, Tope invested his entire life savings of $200,000 into creating Calendly, betting everything, including his 401(k) and maxed-out credit cards. He worked out of Atlanta Tech Village, a startup haven, to bring his vision to life. This time, Tope was solving a problem he cared about. It's like he finally realized that the key to success isn't just making money. It is making something that makes people’s lives easier. For him, it was building Calendly.

But how did he turn a simple idea into a multi-million dollar company?

First, let's look at Tope's approach to product development:

1. User-Centric Design: Tope focused on creating a product that was intuitive and easy to use. He understood that for scheduling software to be successful, it needed to be simpler and more user-friendly than existing options.
2. Solving for Both Sides: Unlike many of his competitors, Tope designed Calendly to improve the experience for both the scheduler and the person being scheduled. This dual focus was a key differentiator. Imagine you're trying to schedule a meeting. On one side, you have the scheduler, juggling multiple calendars and availability. On the other side, you have the invitee, who just wants to pick a time without a lot of back-and-forth. Calendly addressed both these needs, creating a smooth experience for everyone involved.

Now, let's talk about Tope's growth strategy:

1. Freemium Model: Initially, Calendly was completely free. This wasn't exactly planned—Tope ran out of money before implementing a billing system. But this "accident" turned out to be a crucial factor in Calendly's rapid growth.
2. Viral Marketing: The nature of Calendly's product meant that every time someone used it to schedule a meeting, they were essentially marketing it to a new potential user. This viral loop was a powerful growth driver.
3. Focus on Integrations: Tope understood the importance of making Calendly work seamlessly with other popular business tools like Salesforce, HubSpot, and more. This strategy increased Calendly's value proposition and made it an essential part of many users' workflows.

Tope's approach to building and growing Calendly teaches us several important lessons:

1. Solve a Real Problem: Calendly addressed a genuine pain point that many people experienced daily.
2. User Experience is Key: By focusing on simplicity and ease of use, Calendly was able to stand out in a crowded market.
3. Leverage Network Effects: The viral nature of Calendly's product was a crucial factor in its rapid growth.
4. Integrate and Expand: By working well with other tools, Calendly became an indispensable part of many users' tech stacks.

Tope Awotona's success with Calendly wasn't just about having a good idea. It was about executing that idea in a way that prioritized user needs, leveraged organic growth mechanisms, and created real value for users. Tope emphasizes the importance of customer feedback in driving product development. "A picture's worth a thousand words," he says in a podcast conversation. "If I'm describing something to our product people, I can just share a screenshot or record a quick video and share it with them." This approach ensures that the platform evolves to meet the needs of its users effectively.

Against the mainstream idea that successful startups need significant venture capital funding, Tope bootstrapped Calendly for years, proving that with the right product and strategy, it's possible to build a successful SaaS company without huge external funding. 

At the start, Tope, like most entrepreneurs, wanted that VC money and so he went into these VC offices expecting to impress them and win their support. As a Black builder and entrepreneur, he got rejections upon rejections. These rejections turned out to be some of the best things that could've happened to Calendly. Without VC money, Tope had to focus on actually making money. By providing value upfront with the Freemium model, Calendly was able to gain widespread adoption quickly, and as users found the platform beneficial, many upgraded to premium plans, driving revenue growth. 

Despite this fundraising challenge, Calendly achieved profitability within three years. "It could’ve gone really badly," he admitted, reflecting on the high stakes of his early investment. Reflecting on his journey, Tope credits his success to grit, determination and the Nigerian spirit.

"I just know the country that produced me," he said in an interview with TechCrunch. "There are a million Topes in Nigeria… I’m not a diamond in the rough, and I want to get involved in some way to help with that."

By 2021, Calendly had grown to over 10 million users, with revenues exceeding $100 million. Tope eventually raised $350 million from OpenView Venture Partners and Iconiq Capital, which valued the company at $3 billion. This infusion of capital allowed Calendly to invest heavily in product development, marketing, and international expansion, positioning it as a dominant player in the scheduling software market. The strategic timing of this funding round ensured that Calendly could capitalize on its growth momentum and solidify its market leadership.

Customer feedback is gold for Tope, who believes in evolving the platform to meet users' needs. His vision for Calendly extends beyond scheduling to a suite of tools for managing meetings before, during, and after they occur—tapping into a potential $20 billion market.

Tope’s journey is also about giving back. Inspired by his parents, he supports aspiring entrepreneurs, particularly in Nigeria, and is passionate about diversity and inclusion in tech. "And another issue that I'm passionate about is just improving diversity and inclusion in the tech space," he noted. He's contributed to organizations like Black Girls Code and My Brother’s Keeper, aiming to nurture the next generation of innovators.

Today, Tope Awotona isn’t just the richest Nigerian immigrant in the U.S.; he's proof of how innovation, resilience, the Nigerian spirit, and a bit of scheduling magic can transform the world. More importantly, Tope’s story reminds us that the path to success is rarely linear. It's the lessons we learn along the way that often prove most valuable.

If you found Tope's story inspiring, don't forget to share this article with your network and help us spread the word. And do subscribe to get more inspiring stories like this in your inbox.

Sources:

Nigeria-Born Tope Awotona Poured His Life Savings Into Calendly. Now He’s One Of America’s Wealthiest Immigrants

Calendly's Founder: Building a $30M SaaS After 3 Failed Startups

Tope Awotona, 42-year-old richest US-based Nigerian who owns $3bn tech ...