Tope Awotona, Founder and CEO of Calendly, shares his inspiring journey from Nigeria to tech entrepreneurship. He recounts his many failed ventures before landing on the idea of simplifying scheduling through software. The discussion delves into personal tragedies and the resilience required to overcome them, alongside navigating the challenges of securing a technical co-founder. Tope reflects on the delicate balance of luck and hard work in business, ultimately showcasing Calendly's remarkable growth and the emotional facets of his entrepreneurial spirit.
Tope Awotona struggled to find a compelling business idea until he encountered the difficulties of scheduling meetings, inspiring him to create Calendly as a simplified meeting scheduling platform.
Tope learned the importance of resilience and building a thick skin in the face of rejection, gaining inspiration from successful entrepreneurs who faced numerous 'no's' before achieving success.
To fund the development of Calendly, Tope invested significant personal funds, including emptying his 401k and borrowing money, leading to the unexpected adoption of the product and the need to explore alternative revenue models.
Deep dives
Calendly: From Frustration to Success
Tope O'etana, the founder of Calendly, struggled to find a compelling business idea until he encountered the difficulties of scheduling meetings. Inspired by the challenge, he decided to create a meeting scheduling platform that simplifies the process. The initial version of Calendly, built with the help of a Ukrainian development company, focused on integrating users' calendars and allowing them to specify their availability. With a strong emphasis on user experience and design, the product aimed to revolutionize meeting scheduling. Despite running out of funds during development, Calendly gained traction when a customer success team from another company discovered and started using it for onboarding calls. Adoption expanded as K-12 schools began utilizing Calendly for parent-teacher conferences. The product unexpectedly became free since the necessary billing features couldn't be developed due to limited funds. Despite this, Calendly's popularity grew, and Tope had to think about different revenue models to sustain the company's success.
Overcoming Rejection and Embracing Entrepreneurship
Tope's journey as an entrepreneur wasn't without obstacles. He faced rejection and failure in his previous business ventures, losing significant amounts of money along the way. However, those experiences taught him the importance of resilience and building a thick skin in the face of constant rejection. Tope recognized the value of practice and perseverance, drawing parallels between his own struggles and those of successful entrepreneurs like Mark Cuban and Sarah Blakely, who had to face numerous 'no's' before achieving success. Armed with lessons from previous failures, Tope embraced the challenges of entrepreneurship, seeing it as an attainable goal rather than an elusive dream.
From Risky Investment to Frustrations Turned Opportunity
Tope's dedication and belief in Calendly pushed him to invest significant personal funds, including emptying his 401k, depleting his savings, and borrowing additional money to fund its development. Despite financial risks, Tope took the leap of faith and poured himself into the product, finding solace in the work and distraction from personal challenges, including the terminal illness and eventual death of his mother. Launching with a free model due to budget constraints, unexpected adoption by K-12 schools for parent-teacher conferences fueled Calendly's early success and drove the need to explore alternative revenue models to sustain its growth.
Starting a Business Selling Projectors
The podcast episode discusses Tope Awatana's experience of starting a business selling projectors. He invested $20,000 of his own money and faced challenges such as thin profit margins and tough competition. Despite the business lasting less than six months, Tope remained determined and learned valuable lessons about the need for passion and knowledge in a business venture.
Pivoting to Ecommerce with Yardstills.com
After the projector business failed, Tope Awatana pivoted to ecommerce and created Yardstills.com. He identified the opportunity to sell the popular Big Green Egg grill to customers who had difficulty accessing it in non-major cities. By leveraging his coworkers' enthusiasm for the grill, Tope built another ecommerce website and successfully generated better margins. However, he ultimately realized that to build a successful business, he needed to be genuinely passionate about the products and industry.
After emigrating from Nigeria to the US to attend college, Tope Awotona worked as a door-to-door salesman and eventually set out to become a tech entrepreneur. He launched a series of e-commerce businesses that quickly fizzled when he realized he had no passion for them. But then he landed on an idea he was truly excited about: designing software that would minimize the hassle and headache of scheduling meetings. In 2013, he cashed in his 401k and went into debt to build Calendly, a scheduling service reportedly doing over $100 million in revenue.
This episode was produced by Rachel Faulkner-White, with music by Ramtin Arablouei
Edited by Neva Grant, with research help from Daryth Gayles.
