Prompt Cast
From Frustration to Success: The Story of Calendly Founder Tope Awotona
TLDR Tope Awotona founded Calendly after experiencing frustration with scheduling meetings, leading to a successful business that reached $60 million in annual revenue within seven years. Despite facing challenges in raising money and investing over $200,000 of his own money, Tope Awotona's dedication to solving a real problem and commitment to learning paved the way for the organic growth and success of Calendly.
Timestamped Summary
00:00
Tope Awotona turned his frustration with scheduling meetings into Calendly, a multi-million dollar business that simplifies setting up meetings.
06:22
Tope Awotona founded Calendly after experiencing frustration with scheduling meetings, leading to a successful business that reached $60 million in annual revenue within seven years.
12:37
Tope Awotona moved from Lagos, Nigeria to Marietta, Georgia as a teenager, where he faced social challenges in high school but eventually pursued computer science at the University of Georgia before transitioning to a business degree.
18:25
Tope Awotona enjoyed door-to-door sales because of the immediate impact on his earnings and the challenge of influencing people's decisions, which was different from his computer science background, leading him to seek accelerated career growth opportunities in sales roles after college.
23:44
Tope Awotona realized that entrepreneurship was more attainable than he thought after learning from customer feedback and decided to start dabbling in small businesses, eventually launching an e-commerce projector business called projectorspot.com.
29:22
Tope Awotona's initial e-commerce ventures selling projectors and grills taught him the importance of being passionate and knowledgeable about the products he was selling, leading him to focus on higher-margin products and invest in building a brand and educating customers for future success.
34:59
Tope Awotona realized the importance of being passionate about solving a real problem and being committed to learning about it before starting a successful business, leading him to identify a gap in the market for a scheduling and calendar solution tailored to enterprise software sales reps.
40:26
Tope Awotona saw an opportunity to create a scheduling solution that would simplify the process for casual users, leading him to invest all his resources into the project after six months of research and contemplation.
46:30
Tope Awotona decided to outsource the development of his scheduling solution to a company in Ukraine after facing challenges in finding a technical co-founder and investing over $200,000 of his own money to bring the idea to life.
52:15
Tope Awotona invested a significant amount of his own money, including his 401k, savings, debt, and maxing out credit cards, into his scheduling idea, feeling confident due to his previous failures and belief in his calling.
58:26
Calendly gained popularity organically as K-12 schools started adopting it for parent-teacher conferences, leading to a dilemma for Tope Awotona as the product became free due to lack of billing features and funding, prompting him to seek investors while still working his day job.
01:03:57
Tope Awotona faced challenges raising money for Calendly, experiencing condescension and arrogance from investors, but eventually connected with David Cummins who invested $350,000, leading to the introduction of a premium plan to generate revenue in August 2014.
01:10:17
Tope Awotona initially charged $10 monthly or $96 annually for Calendly, with the goal of eventually acquiring larger customers like Microsoft, and despite only raising $550,000 in outside funding, the company has grown to have close to 200 employees and generate $60 million in revenue annually.
Categories:
Business
