Tope Awotona is founder/CEO, Calendly, a scheduling software company he birthed in his quest for a solution to back-and-forth emails that used to precede scheduling meetings. His company specializes in scheduling software that simplifies the process of scheduling meetings and appointments.
He set up Calendly in 2013, which has grown exponentially to a valuation of over $3 billion after closing an investment of $350 million in a 2021 funding round.
Awotona’s idea of creating a scheduling product was inspired by his personal challenge encountered in the process of scheduling a meeting. Frustrated by too many emails that had to fly back and forth, he researched the market and spotted the gap – that none of the scheduling products, permitted multiple users to share availability.
Calendly is his step forward to fill the gap in a ready market by offering a simple scheduling app. The market responded with 20-30 million subscribers worldwide and more than $60m annual revenue in seven years. That has lifted the Lagos-born tech expert to one of America’s richest immigrants.
Demand is doubling from year over year, creating a success rate that far exceeds the expectations of even the most ambitious business adventurers.
Awotona immigrated to the United States as a teenager and studied management information systems at the University of Georgia. After graduating, he worked for tech firms as salesman, including IBM and Dell EMC.
His dogged desire to move up the ladder of success got a big boost when he joined Perspective Software – a scaling start-up company in Kansas City as an account executive selling to more than 50 colleges and universities. Speaking of the experience, he recalls: “it was the best thing that ever happened to me! I had to learn how to make customers happy, sell the product and work with legal, all while maintaining a $2 million quota.”
The job exposed him to the different functions of a software business quite a preparatory training for what was to come. “The company was growing so fast. I was working with a team of brilliant, hardworking and passionate people in an inspiring building. This is what I knew I wanted,” he said.
Driven by a strong entrepreneurial spirit, Awotona went into a few businesses that flopped. The first was a dating website, STT Media, which never launched for lack of skills and the means to do it as well as he wanted.
His second start-up was an e-commerce website he built for selling projectors. It also didn’t go far for being an unfamiliar field for him without much passion as well. “I didn’t know anything about projectors and honestly I didn’t want to know about them,” he said.
Yet another step in his entrepreneurial journey was a grills selling website, yardsteals.com. Though it was more rewarding than his experience with projectors, the same problem of insufficient knowledge and lack of passion kept him searching for something fulfilling.
As a growing up child, he was focused on making sure that money should never be a problem but at this stage he came to realise that self-fulfillment is the key element of success.
The narrow idea of starting a business to make money by reselling products needed to give way to knowledge-based, problem-solving product that would capture a good part of the value chain in a critical field.
“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,” he said.
All along, Awotona knew quite clearly, he wanted to be an entrepreneur and was eagerly testing and trying ideas and opportunities to log on to the perfect path to destination. Perspective Software provided the door for him as well as the knowledge guide to step ahead and move on. Calendly couldn’t have happened without Perspective Software, according to him.
A historic moment came one day when Perceptive Software’s founder told the staff at a meeting the story of how his company moved from an idea to fruition. The many twists and turns in the company’s operating story, the mistakes and the learning therefrom, the persistence and the resulting great success provided a rich vineyard of entrepreneurial knowledge to Awotona.
From the Perspective Software’s corporate story, he realized for the first time that success in business enterprise doesn’t often come through straight and easy paths. It was first-hand learning for him that it takes smart people to start great companies but more importantly, it takes decisive actions on opportunities to succeed and tenacity to survive and grow.
“It made entrepreneurship all of a sudden more attainable. I knew if they could do it, I could too,” he said.
When he discovered the gap in the scheduling app, he was convinced within himself that it was a problem he quite understood and therefore a problem for him to solve. The product idea filled the missing elements of something he understands and something he has passion for. Leaning on his software experience, he was quite convinced it was something he could build, scope and manage the execution. “I just knew I could do it. I knew there was a business there,” he said.
In building Calendly, Awotona invested every single dollar he had ever made in it not knowing how big it could be, but quite convinced it was such a great opportunity. It was a matter of all eggs in one basket that either succeeds to a great height or falls to a great disaster. Recalling the level of risk exposure, he said “if it hadn’t taken off, it would have set me back many, many years.”
He has experienced the emotional roller coaster that marks the story of building an enterprise and learned from the daily exciting and humbling developments that shape the corporate future. He has seen the results of deliberate decisions and can distinguish same from luck that sometimes happen in the process. The key, he said, is to figure out the things that are pure luck and leverage them to advantage.
Awotona has positioned Calendly as a problem solving product that serves hundreds of millions of people worldwide. He recommends the path he has followed: “if you want to be an entrepreneur, become really good at something. Make sure you fully understand the problem, and be well informed enough to have strong opinions about the solution. Only then are you ready to start a company. I learned that the hard way. Don’t try to solve a problem you don’t understand and be honest with yourself about what you are really good at.”