Tope Awotona Built a Billion-Dollar Business from an Everyday Problem. Here Is What We Can Learn

Some of the most successful businesses begin with problems people encounter every day. The difference often lies in recognising that an inconvenience could become an opportunity worth pursuing.

For Tope Awotona, that opportunity came from something as ordinary as scheduling meetings.

Born in Lagos, Nigeria, Tope moved to the United States with his family at the age of 15. After studying Management Information Systems at the University of Georgia, he built a career in software sales, working with companies including IBM and EMC. He also had an interest in entrepreneurship and had made several attempts to start businesses of his own.

However, those early ventures did not succeed. He tried a dating website, an online store selling projectors and another business selling garden equipment. Each attempt came with its own challenges, but they also gave him valuable experience.

His breakthrough came while working in software sales. Arranging meetings with clients often involved lengthy email exchanges, with people going back and forth trying to find a suitable time. He found the process frustrating and began exploring ways to make it easier.

Rather than accepting the inconvenience as part of doing business, he saw an opportunity to solve it.

In 2013, he founded Calendly, a scheduling platform that allows people to share their availability and book meetings without the usual exchange of emails.

Building the company, however, required a significant personal commitment. To fund its development, Tope invested approximately $200,000 of his own money, including his savings and retirement funds, and took on additional debt. It was a considerable risk, especially for someone whose previous business attempts had failed.

His decision eventually paid off. Calendly grew into a global software company, attracting millions of users and major business customers. In 2021, the company reached a valuation of $3 billion, establishing Tope as one of the most successful Nigerian-born entrepreneurs in the technology industry.

His story offers valuable lessons about recognising opportunities, learning from failure, taking calculated risks and building businesses that create value.


1. Opportunity Often Hides in Everyday Problems.

    Awotona saw business potential in something many people considered a routine inconvenience: scheduling meetings. He recognised that a simple problem affecting millions of professionals could become a valuable business opportunity. His experience reminds us to look more closely at everyday challenges because some of the biggest opportunities are hidden in plain sight.

    2. An Idea Is Only the Beginning.

      Building Calendly required more than identifying a good idea. It involved committing personal resources, finding technical expertise, developing the product and working towards a sustainable business. His experience highlights the role of execution, sound decisions and the ability to turn an idea into something people are willing to pay for.

      3. Failure Can Be a Stepping Stone to Better Opportunities.

        Before Calendly, Awotona had tried several business ideas that did not gain traction. Each attempt exposed him to the realities of building a business and helped shape his approach to entrepreneurship. His experience shows that an unsuccessful idea does not have to mark the end of entrepreneurial ambitions.

        4. Conviction Requires a Willingness to Take Risks.

          Awotona committed approximately $200,000 of his personal savings and retirement funds to building Calendly. His decision demonstrates the importance of believing in an idea, recognising its potential and being willing to commit resources towards making it a reality.

          Wealth creation often begins with the ability to recognise value where others see an ordinary problem.

          The Brief Network: Inspiring Stories and Empowering Lessons.

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