Tope Awotona, founder of Calendly, shares his journey of building the scheduling platform, overcoming challenges and failures. He discusses the decision-making process, finding a technical co-founder, and the early days of Calendly. Awotona also reflects on the factors contributing to success and the growth of the company, now valued at $3 billion.

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 expected to make about $60 million this year.Pre-order the How I Built This book at: https://smarturl.it/HowIBuiltThis See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Entrepreneurial outsider Shellye Archambeau, Ellevest's Sallie Krawcheck, and Calendly's Tope Awotona discuss the hidden advantages of strategizing like an outsider. Topics include questioning the status quo, maintaining confidence in the face of criticism, and orchestrating a cultural turnaround.