CEO & Founder, Calendly
3 BUSINESS VENTURES FAILED,7 YEARS LATER HE FOUNDED A $1.4B COMPANY Calendly | Tope Awotona Success
Born in Lagos and raised in Atlanta, Tope Awotona stared down tragedy, built three failed startups, drained his savings and ...
About Tope Awotona
Tope Awotona, founder and CEO of Calendly, discussed his journey from emigrating from Nigeria to the U.S. for college to building the scheduling platform. He described working as a door-to-door salesman and launching several e-commerce businesses that he said failed because he lacked passion for them. In 2013, he said he cashed in his 401k, used his savings, borrowed from Lending Club at a high interest rate, and maxed out his credit cards to fund Calendly, which he described as an idea that "at the time didn't even have a name." Awotona stated that he believed the key to success was "the execution of it, not so much just the idea," noting that others had the same concept but he planned to execute it differently. Calendly was reportedly doing over $100 million in annual revenue as of a 2020 interview, and the company later took on outside investment with a valuation of $3 billion. During the COVID-19 pandemic, the company reported that small business owners set 13 million more meetings through the platform compared to the same period before lockdowns. Awotona attributed success to a combination of "hard work, skill, resilience, and an appetite for risk taking."
Transcript (15 segments)
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Narrator0:00
He experienced trauma at 12 years old and failed in three startup attempts. He quietly built the Atlanta Tech Village. The world learned in 7 years. He made $550,000 after the rejections. Today, $1.4 billion. A black tech billionaire.
Tope Awotona was born in Lagos, Nigeria in 1981 to a family of entrepreneurs. His father, a microbiologist turned entrepreneur; his mother, a banker. When he was just 12 years old, he witnessed his father being killed in a carjacking. He later recalled, 'In Nigeria, it happened on Friday and I went to school on Monday.' For six months, he says, he couldn't sleep or eat. That trauma instilled in him a deep drive not just to succeed, but to finish what his father never could.
The Immigrant Learning Center. At age 15, his family immigrated to Atlanta, Georgia. The culture shock was real, from Lagos's hustle to American high school halls. He enrolled at the University of Georgia and graduated with a BBA in management and information systems in 2002. His mother supported him with quiet determination; his father's memory pushed him. The combination created a resilience he would later rely on.
After college, Tope entered enterprise software sales at IBM, Perceptive Software, and EMC, where he learned the mechanics of deals, quotas, CRM systems, and the frustration of scheduling endless meetings. In parallel, he tried three startup ventures. Each was unsuccessful, but each taught something crucial.
Dating website STT Media: inspired by a New York Times article about online dating success, he launched it, but it never achieved traction. He lacked domain passion and users. Lesson: you shouldn't start a business only for money if you don't care about the problem.
Projectors e-commerce Projectorspot.com: he sold projectors via Amazon and eBay, but margins were thin, supplies inconsistent, and he admitted, 'I did not know anything about projectors.' Lesson: inventory-heavy plus no domain expertise equals high risk.
Garden and outdoor equipment Green Eggs knockoff business: he sold knockoff grills and made a small profit, but he was uninterested. 'I lived in an apartment, never even grilled.' Lesson: passion matters for the long haul.
Scaling over a decade. He accumulated savings from his sales job and modest side earnings. He reportedly saved up approximately $200,000, including draining his 401k and maxing out credit cards to fund his next venture. In deciding to go all in, he didn't hedge. This next step would be different.
In late 2012, during yet another frustrating scheduling exercise for a meeting, Tope realized scheduling is broken. He joined Atlanta Tech Village co-working space in 2013, a community of entrepreneurs with access to mentorship and the energy of startup culture. Using nearly all his life savings and credit card debt, he launched Calendly in September 2013. He put in his own money; there was no co-founder listed publicly.
The early years were hard: slow user growth, product refinement, repeated, misleading 'almost quit' nights. He has said it took over seven years for the world to learn of Calendly. The breaking point came when early users, entrepreneurs at Atlanta Tech Village, started spreading word of mouth. A tweet from others in the space caught the attention of an investor, David Cummings of Atlanta Ventures.
In April 2014, Calendly raised its first seed round of $550,000 after being refused many times. What made Calendly different? A one-click scheduling link that synced with Google and Outlook calendars, a freemium model where free users invite others, creating a viral loop, and a focus on solving a real pain point he himself faced: sales scheduling. Rather than chasing a trending industry, Calendly achieved profitability around 2016.
Despite profitability, Tope chose to raise funding in 2021 to accelerate enterprise go-to-market, global reach, and scale teams. Calendly raised $350 million in that round, valuing the company at $3 billion. His prior enterprise sales background played a major role: he understood onboarding, CRM, sales cycles, and enterprise buying behavior, and brought that to product-market fit.
Atlanta, rather than Silicon Valley, was a deliberate strategic choice: lower costs, a vibrant ecosystem via Atlanta Tech Village, and community support. Under his leadership, Calendly expanded remote work, built a global presence, and began focusing on enterprise tiers paying hundreds of thousands for scheduling infrastructure.
Today, Tope is a billionaire with a net worth estimated at $1.4 billion, and his story stands out as one of the few black-founded tech unicorns. He speaks often of giving back; Calendly supports underrepresented founders, has worked with initiatives like Black Girls Code, and provided relief to Ukraine-based developers.
The Immigrant Learning Center. His future vision: 'We solved scheduling. Now we help professionals prepare, follow up, and be fully present in meetings.' He emphasizes that his immigrant background is not a hindrance but a strength: 'Your background is what you make of it. It can be an asset or an excuse.' He also champions diversity in tech, not tokenizing his story, but acknowledging the barriers he faced.