In 2013 he put $200K into Calendly, now worth $3B with 50M users

In 2013, entrepreneur Tope Awotona founded Calendly to address the frustration he experienced while scheduling meetings for his sales work. He invested his personal savings and sought loans, ultimately spending over $200,000 to build the initial product. Eight years later, Calendly had attracted more than 50 million users and a $3 billion valuation, according to TechCrunch.

Awotona's background included work in enterprise software sales for IBM and Dell, giving him firsthand knowledge of the scheduling challenges he sought to solve. He hired a development team in Ukraine, even traveling to Kyiv in 2014 during anti-government protests to oversee the project's progress.

Awotona financed the business out of pocket, using his retirement account, savings, and debt. By November 2020, the company had raised about $550,000 in outside investments, focusing on revenue and organic growth rather than repeated large fundraising rounds. This strategy enabled Calendly to reach new users through word-of-mouth and professional interactions, a valuable tactic as remote work and virtual meetings gained prominence during the COVID-19 pandemic.

In January 2021, Calendly secured a $350 million investment from OpenView Venture Partners and Iconiq Capital, valuing the company at over $3 billion. Since then, the platform has evolved from a simple scheduling tool into a comprehensive meeting-management system, with over 50 million users across 240 countries and territories, and facilitating more than 1.3 billion meetings.