A Page From The Atlanta Playbook, As Told By The Mayor & A Unicorn Founder

On his 99th day in office, Atlanta Mayor Andre Dickens sat down with Calendly founder Tope Awotona for a conversation and reflection on the Atlanta entrepreneurial ecosystem. 

It was a fitting way for the “Tech Mayor” to mark such a milestone. As an Atlanta native, Georgia Tech graduate, entrepreneur, and elected official, Dickens has seen the city and the local tech ecosystem transform over the last decade.

Dickens was asked by the moderator of the event, The Gathering Spot’s co-founder Ryan Wilson, to put this moment in Atlanta’s history into perspective for the audience. 

“This is the day after Graduation Day in the life of Atlanta,” Dickens told the crowd. “We’ve gone through toddlers days, we’ve gone through high school, and we graduated. We are here now as a full-fledged adult city with a real ecosystem, a real economy, and a place on the national stage.” 

Calendly played an important role in the maturation of the city’s ecosystem. 

Long before the billion-dollar valuation and the cover of Forbes, Awotona saw Atlanta as a unique space to grow an early idea. Awotona said he was drawn back to Atlanta to start his entrepreneurial journey in the mid-2000s because of the momentum already growing in the tech scene.

IBM (where Awotona started his career) acquired Atlanta-based ISS in 2006 for over $1 billion, and he was already looking up to the likes of Mailchimp and Pardot. 

“In the early days of Calendly, there were already many examples of people who had done it here in Atlanta,” Awotona added. “And in the early days, people would ask me when I would be moving to San Francisco. And to me, that was a silly question. I’d already seen some good examples of successes here in Atlanta.”

Dickens recalled that when he was a chemical engineering student at Georgia Tech in the late 90s, “computer science talent bled to the coasts after graduation.” 

“But Atlanta held its own enough to get to where now and have a critical mass of an ecosystem. Now, Atlanta has a resume,” Dickens added. 


While Atlanta has “graduated,” Dickens was quick to add that “we know ourselves, but we still have to know a lot more about ourselves.” 

Like all recent graduates,  Awotona and Dickens both recognized that working through doubt is an important part of growth. Both men shared their personal experiences about what doubt looked like when scaling early-stage businesses.

“Sometimes people doubt you, and sometimes you quietly doubt yourself. But it’s an emotion that is made to move through you,” said Dickens. “If you rest in that emotion too long, that’s when it’s problematic. So when doubt hits, you have to let it move through you and move on past you. And you have to convey that to people who may rest in doubt about you…you have to get those people to move past the doubt about you.” 

Dickens talked about building up his furniture business, City Living Home Furnishings, and learning the valuable lessons about needing to hire the right team members to drive success. That is a lesson he’s taken to City Hall.

For Awotona, doubt that has crept in over the journey has been used as an opportunity to bring clarity. 

 “I think first and foremost, anytime someone doubts, there’s probably some element of truth to what they’re saying,” he said. “And so I try to understand what it is that I know they don’t, and what do they know that I don’t.” 

“Doubt is just an information gap,” Awotona added.


Photo: The Gathering Spot’s Twitter


So what should Atlanta be focusing on in its “post-graduate” phase? Dickens and Awotana agreed it is about cultivating and retaining local talent and building up “cross-functional capabilities” to help someone turn a great idea into a scalable one. 

“There’s a lot of capital for seed and Series A businesses, but there is a drop off in getting business from idea to their first $100K or so in revenue,” said Awotona. “It is one of the most difficult phases for a business. If you can get through that, there is a lot of support and capital to help you scale.”

“We have to be Inclusive in our excellence,” added Dickens. “When we tap all the way in…that’s something that generations in the future will be talking about.”