Tope Awotona - A Founder Story

April 26, 2018

Babatope (Tope) Awotona is the Founder of Calendly, a beautiful, simple scheduling tool that in less than 5 years has served close to 30 million people worldwide and is currently growing 100% year over year. His success to date has exceeded most entrepreneurs’ dreams, and it all started in one of the fastest growing cities on earth.


Tope’s Founder story begins in Lagos, Nigeria. He was the third of four children (all boys), and the Awotona’s big family meant their house was always filled with people and laughter. Tope’s childhood was a good one where community and boy adventures were always close by. In true entrepreneurial form, Tope claims “I got into just the right amount of trouble growing up…to where I had a lot of fun, but no one ever called my parents. I knew exactly what I could get away with and toed that line.” [caption id="attachment_16357" align="alignright" width="370"]

Tope (2nd from left) with his brothers in Nigeria.[/caption]In Tope’s words, he was “lucky to have two of the coolest parents in the world.” His Dad was the more lenient and easy going one, a beloved jokester with a big heart. His Mom was a tough woman who was ambitious, driven, and strict. She was always asking “What is your plan?” and looking 10 years ahead. Nigeria is a country with a huge wealth disparity - most are either very rich or very poor. Tope’s parents actually came from both of those backgrounds. His Mom grew up in a wealthy family but his Dad came from a very poor and broken home. Tope’s father picked himself up from his bootstraps and through a lot of hard work and a bit of luck - he was able to escape that cycle. This background meant that Tope’s parents constantly reminded him that they had what a lot of people didn’t and how important it was to be grateful. His Mom was the Chief Pharmacist for the Central Bank of Nigeria. His Dad was a microbiologist by training and worked for the Nigerian division of Unilever, but he was an entrepreneur at heart. These two parental perspectives gave Tope a lot of insight into what he wanted for his life.


Tope’s father tragically passed when he was only 12 years old. This solidified Tope’s desire to fulfill his Dad’s dreams of being a successful entrepreneur. You see while his father had much success at Unilever, his startups tended to have more downs than ups. With 4 kids and lots of responsibilities, this created a tension point for his family growing up. Tope wanted stability, but he also wanted to redeem his Dad’s dream of owning his own company and to do it better than he had. [caption id="attachment_16362" align="alignleft" width="370"]

Tope with his Mom and Dad.[/caption]Tope knew even as a child that he never wanted money to be a problem. He didn’t want his future wife to ever feel financially insecure. In Tope’s words, “I thought the best way to do that would be to start a business with the goal of making a lot of money. Of course, over time it became about much more than money, but that was how it all started.” And for Tope (with his mom and dad’s unwavering support) that dream started with an education.“My parents never told me to go to college or what to do, it was just the only example I ever saw.” And Tope had the smarts to get him there. Part of a gifted program as a kid, Tope actually graduated high school two years early and was granted a scholarship to a US college at 15 years old. But, his mom intervened. She felt he was still too young and decided Tope would attend American high school for his Junior and Senior years first.


Tope’s mom packed their family up and moved them across the world to Marietta, GA, joining other Awotona family members, so he could attend Wheeler High School. In his words, “It was super frustrating. I felt like I was wasting time because I had my plan in place.” But, he admits it worked out well. “My mom was wise. Those two years helped me assimilate well to the US and gave me time to learn the culture here.” Tope graduated high school and attended the University of Georgia (Go Dawgs!) majoring in Management Information Systems. After graduation, Tope worked a couple different corporate jobs (including IBM), but he was a man on a mission and quickly realized it would take too long to work his way up. So he joined a scaling startup in Kansas City, Perceptive Software, as an account executive selling to 50+ colleges and universities across all departments. In his words, “It was the 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 $2M quota.” This exposed Tope to all the different functions of a software business and would serve as some of the best training he could get 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. We had a slide and dodgeball tournaments. This is what I knew I wanted.”


Tope claims that Calendly would have never happened without his experience at Perceptive Software. He always knew he wanted to be an entrepreneur, but was waiting for the perfect path to get there. Until one day, when Perceptive had a staff meeting where their Founder, Scott Coons, told the story of how the company went from idea to fruition. For the first time, Tope realized that successful companies do not always take a straight path forward. The Perceptive startup story had many twists and turns, but they learned from their mistakes, kept persisting, and it still led to great success. This was Tope’s aha moment. He learned first hand that people who start great companies are smart but, more importantly, they take action when they see opportunity and stick with it to make it work. As Tope shared, “It made entrepreneurship all of a sudden more attainable. I knew if they could do it, I could too.”It was around this time that Tope received the news that his mom was diagnosed with cancer. So he quickly packed up and moved back to Atlanta to be with her. He also decided to start his entrepreneurial journey.


Tope’s first idea? A dating website. Tope read a New York Times article about the Founder of a startup called Plenty of Fish who was making $10M/year working 10 hours a week. Tope was inspired. He looked up their website and instantly knew he could build something better. STT Media was born which stood for “Single To Taken.” never launched. Tope quickly realized that he didn’t quite have the means or skills to do it as well as he wanted. Tope’s second startup began when a business broker (long story short) convinced Tope to build a website around selling projectors. was born. It was an ecommerce site selling, you guessed it, projectors. According to Tope, he didn’t sell many and the margins were terrible. “I didn’t know anything about projectors! And honestly? I didn’t want to know about them.” His third startup came when he pivoted from projectors to grills and started He had a bit more success selling knock-off Big Green Eggs, but quickly realized he had the exact same problem. He was pulling more profits, but he still wasn’t passionate or knowledgeable about what he was selling. In Tope’s words, “Once again, I didn’t know anything about grills and I didn’t want to! I lived in an apartment, and never even grilled.” He laughs.


Tope realized he kept doing things he wasn’t passionate about and decided to make a bigger commitment. His previous efforts had been only about starting a business to make money, but he knew that wasn’t working. His new focus would have to be something he was knowledgeable about, that could solve an important problem, and be something proprietary. No more reselling. He took a breath and waited for the right idea. He would own the product and capture more of the value chain in his next startup.

About a year went by, until one day in late 2012, Tope was trying to schedule a meeting which resulted in a ton of back and forth emails. He googled existing tools but to his surprise found that they were all slow and clunky. He became obsessed with the gap in the market and finding something better. Was this his problem to solve? The product idea fit all of his requirements for his next startup: as a sales rep he had scheduled a lot of meetings and understood the problem, it could be proprietary because he could build it himself, and because of his software experience he knew he could build, scope, and manage the execution. In Tope’s words, “I just knew I could do it. I knew there was a business there.”In early 2013, Tope started building Calendly. He says, ‘I went for broke and put every single dollar I had ever made into it. I didn’t quantify how big it could be, but I knew it was such a great opportunity that I literally put everything on the line.  If it hadn’t taken off, it would have set me back many, many years.” The most bittersweet part of his journey? Tope’s Mom passed away the same year he started Calendly. His loving, protective mother would have been so scared of the risk, Tope knew she wouldn’t have been able to be supportive. So he never fully told her what he was doing. In Tope’s words, “I wish my mom could see what Calendly is now. Parents do so much and sacrifice so much for their kids that I believe it’s the ultimate accomplishment for a parent to see their child be successful. I would give anything for my mom to see what she has done.”Calendly officially launched in September of 2013, and came to Atlanta Tech Village two months later. In Tope’s words, “I fell in love with the atmosphere, everything the building stood for, and just the excitement and the passion of the people there. Everyone was building something, and I knew instantly that I wanted to be there.” Villagers quickly began using Calendly (and tweeting about it) which caught David Cummings’ attention. This ultimately led to Tope’s first investment with Atlanta Ventures which helped catapult Calendly into their next growth phase.


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Ashton Kutcher visiting the Calendly office at the Village.[/caption]It’s been 5 years since Tope launched Calendly, and he says it has been an emotional roller coaster. “I have had times of great exuberance when I felt like we can conquer the world, but that would quickly turn into a low when a customer or employee wanted to leave or we couldn’t get a feature right. Growing a company is exciting AND humbling every single day. I’ve made a lot of deliberate decisions, but I’ve also had luck in the process. The key is that we’ve been able to figure out the things that are pure luck and leverage them to our advantage.”As for being Nigerian American? Tope says that for him, it has been helpful. In his words, “Your background is what you make of it. It can be an asset or an excuse. I have never accepted lowered standards. Where I grew up, everyone looked like me - all of our leaders were black, so color didn’t set any limits to my dreaming. But I have learned that growing up black in America is very different. There are not nearly enough examples of people who look like us in positions of power or who have a lot of success in the tech field. Unfortunately, that limits people and can hinder the idea that they can do whatever they want.” Tope’s advice? “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.”


Calendly is a beautiful, simple scheduling tool created by a driven, practical Founder who wanted to build on his Father’s legacy. Like most entrepreneurs, it hasn’t been a straight path to success. But Tope is the kind of person who values the journey - “Everything I did along the way helped me get here. No part could be omitted and have me still end up where I am today.”  The path forward certainly seems straight. Over the next three years, Tope plans for Calendly to literally serve hundreds of millions of people. You should be one of them. Happy scheduling.[caption id="attachment_16354" align="alignleft" width="371"]

The Calendly team at their Atlanta Tech Village graduation party in early 2018.[/caption]To learn more about Calendly check out their website here.

April 26, 2018
Karen Houghton