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.
asserted
he → found → 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.
asserted
building → build → cards
Eight years later, a $350 million funding round valued Calendly at more than $3 billion, according to TechCrunch.
uncertain
round → value → TechCrunch
The company now says its platform is used by more than 50 million people.
asserted
platform → say → people
Awotona, who grew up in Lagos, Nigeria, before moving to the United States as a teenager, had worked in enterprise software sales at companies including IBM and Dell.
asserted
who → grow → IBM
He was familiar with the process of arranging meetings and the time lost to repeated emails proposing dates, checking availability and confirming appointments.
asserted
He → arrange → appointments
Calendly emerged from his frustration with that routine, with the aim of making it easier for people to find a mutually convenient time without lengthy exchanges.
asserted
people → emerge → exchanges
The idea was straightforward: instead of negotiating a meeting time through multiple messages, a person could share a scheduling link showing available slots.
uncertain
person → negotiate → slots
The recipient could select a suitable time, and the appointment would be added to the relevant calendars.
uncertain
appointment → select → calendars
The product turned a familiar administrative task into a simple online process that could be used by individuals, sales teams and businesses.
uncertain
that → turn → individuals
But building the software required more than an idea.
asserted
building → build → idea
Awotona was not a software engineer, so he hired a Ukraine-based company to develop the product.
asserted
he → hire → product
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.
asserted
protests → report → city
The trip illustrated the extent to which he was personally involved in getting the business off the ground.
asserted
he → illustrate → ground
Building a business without rushing to raise money
Awotona’s initial investment was not simply a withdrawal from a savings account.
asserted
investment → build → account
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.
asserted
he → build → debt
The financial risk was substantial: the business had to succeed for him to recover the money he had committed.
asserted
he → have → money
Calendly did not immediately turn to large venture-capital investments.
asserted
Calendly → turn → investments
According to Fortune, by November 2020 the company had raised about $550,000 from outside investors since its founding.
uncertain
company → accord → founding
It had largely built its business through revenue and organic adoption, rather than relying on repeated large fundraising rounds.
asserted
It → build → 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.
asserted
users → explain → product
That approach also gave the product a built-in way to reach new customers.
asserted
approach → give → customers
When someone sent a Calendly link to arrange a meeting, the recipient encountered the service and could use it for their own appointments.
uncertain
recipient → send → 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.
uncertain
product → use → advertising
TechCrunch described this organic strategy in its January 2021 report on the company’s funding.
asserted
TechCrunch → describe → funding
The model proved particularly relevant as remote work and virtual meetings became more common during the Covid-19 pandemic.
asserted
work → prove → pandemic
Businesses needed to coordinate conversations with colleagues, customers and prospective clients across locations and time zones.
asserted
Businesses → need → locations
Scheduling software helped reduce the administrative work involved in arranging those interactions, and Calendly was among the services benefiting from the wider shift towards digital collaboration.
asserted
Calendly → help → collaboration
In January 2021, Calendly announced a $350 million investment from OpenView Venture Partners and Iconiq Capital.
asserted
Calendly → announce → Partners
The round valued the Atlanta-based company at more than $3 billion, according to TechCrunch.
uncertain
round → value → TechCrunch
It included both primary investment in the company and secondary transactions involving existing shareholders.
asserted
It → include → shareholders
The valuation marked a significant change from the early days when Awotona had financed product development with his own money and debt.
asserted
Awotona → mark → money
The investment came after years of growth and gave the company additional resources to expand its product and reach.
asserted
investment → come → product
It also demonstrated investor interest in a business built around a relatively narrow task: helping people schedule meetings.
asserted
people → demonstrate → 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.
asserted
appeal → lie → calls
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.
asserted
it → refer → revenue
Calendly remains a privately held business, so its valuation can differ from its worth in a future financing round or sale.
asserted
valuation → remain → round
Forbes also records the 2021 investment and valuation in its profile of Awotona.
asserted
Forbes → record → Awotona
From scheduling links to a broader meeting platform
Calendly’s ambitions have since expanded beyond helping people book appointments.
asserted
people → schedule → appointments
On its official website, the company describes its product as a meeting-management platform designed to support the work surrounding meetings, including scheduling, payments, meeting notes, follow-ups and integrations with other software.
asserted
company → describe → software
…and 5 more, not listed.
The Aporia
