When entrepreneur Tope Awotona founded Calendly in 2013, he put his financial security on the line to solve a problem he had repeatedly encountered while working in sales: the frustrating back-and-forth involved in scheduling meetings. In an interview with How I Built This, Awotona said building the initial product was expected to cost a little over $200,000, forcing him to empty his retirement account and savings, borrow money and max out his credit cards. Eight years later, a $350 million funding round valued Calendly at more than $3 billion, according to TechCrunch. The company now says its platform is used by more than 50 million people.
Fortune reported in November 2020 that he had travelled to Kyiv in February 2014 to assess the situation and continue working with the development team, even as violent anti-government protests were unfolding in the city. In the How I Built This interview, he described combining money from his 401(k) retirement account and personal savings with borrowed funds from LendingClub, alongside credit-card debt. But building the software required more than an idea. Awotona was not a software engineer, so he hired a Ukraine-based company to develop the product. The trip illustrated the extent to which he was personally involved in getting the business off the ground. Awotona’s initial investment was not simply a withdrawal from a savings account. The financial risk was substantial: the business had to succeed for him to recover the money he had committed.
By November 2020 the company had raised about $550,000 from outside investors since its founding, according to Fortune. TechCrunch described this organic strategy in its January 2021 report on the company’s funding. In January 2021, Calendly announced a $350 million investment from OpenView Venture Partners and Iconiq Capital. The round valued the Atlanta-based company at more than $3 billion, according to TechCrunch.
Calendly did not immediately turn to large venture-capital investments. It had largely built its business through revenue and organic adoption, rather than relying on repeated large fundraising rounds. Awotona later explained that the company’s early funding constraints shaped its decisions, including the development of a free version that helped new users discover the product. That approach also gave the product a built-in way to reach new customers. When someone sent a Calendly link to arrange a meeting, the recipient encountered the service and could use it for their own appointments. As more people used the links, the product could spread through ordinary professional interactions, giving the company a route to growth without depending entirely on conventional advertising. It included both primary investment in the company and secondary transactions involving existing shareholders. The valuation marked a significant change from the early days when Awotona had financed product development with his own money and debt. The investment came after years of growth and gave the company additional resources to expand its product and reach. It also demonstrated investor interest in a business built around a relatively narrow task: helping people schedule meetings. Calendly’s appeal lay in addressing a recurring problem across industries, from independent professionals arranging consultations to companies coordinating sales calls, interviews and internal meetings.
The $3 billion figure refers to the valuation attached to the 2021 funding round; it should not be confused with the company’s revenue or current market value. Forbes also records the 2021 investment and valuation in its profile of Awotona. Calendly remains a privately held business, so its valuation can differ from its worth in a future financing round or sale.