The Gathering Spot with Mayor Dickens and Tope Awotona

There are specific nights and moments in Atlanta that need to be documented and tonight was one of them.

Tonight, Mayor Andre Dickens and Tope Awotona (CEO of Calendly) exchanged stories and ideas on stage moderated by The Gathering Spot’s co-Founder Ryan Wilson. 

The Gathering Spot was packed with a line waiting to enter in anticipation of the conversation. The catalyst for the evening was the recent announcement of Calendly reaching mult-unicorn status which Forbes put their stamp on with a front page cover of Tope. 

Calendly’s origin story has been shared in several outlets including our interview with Tope here, Guy Raz’s interview on How I Built This, and the most recent Forbes article, among several others. 

The conversation weaved between ideas on ways to optimize Atlanta’s technology ecosystem to the best ways to scale and fundraise. 

Of the several learnings from the evening, one of the most memorable and insightful topics was around doubt. Ryan asked how each leader handles doubt, both shared the following. 

Mayor Dickens responded that whenever he faces doubt, he knows it’s a temporary emotion and leans back on the dozens of times in the past where he was faced with similar feelings and knows how to manage it. For example, when he was polling at 4%, there was significant doubt about whether he could win, yet he stuck to calling potential donors because he did it nearly a decade ago when he won his City Council seat. He shared several other anecdotes on powering through the doubt. 

Tope shared that when he was raising money and several investors passed on Calendly, he knew it was an information misalignment. His knowledge through research and obsession over the customer problem generated the confidence that he knew something other people and investors did not. He also shared that doubt can be a good thing because there is likely a facet to it that could be true and if so, to find out that piece of information and use it to one’s advantage.

The evening was a huge success and The Gathering Spot put on a tremendous event. 

In the words of Mayor Dickens:

“Atlanta has graduated and now it’s time to enter our adult years.”

Tonight was a great timestamp on over a decade of work and much more to come! 

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