Where there’s a will, there’s a way, and this was the case for founder Ryan Wilson.

Wilson has only worked one job since leaving college, and that’s as the founder of his own business. After graduating from Georgetown Law, he decided to reject a job offer at a law firm. He has since put his all into The Gathering Spot (TGS), a private membership club, founded in 2016 alongside TK Petersen, with Atlanta being its launchpad.

The venture — which has attracted entrepreneurs, creatives, politicians, executives, filmmakers, venture capitalists, and more — has expanded to cities including Atlanta, Chicago, New York City, and Detroit, all featuring a full restaurant and bar, co-working space, and event space. Its most ambitious project is the launch of The Retreat, a 60,000-square-foot space near Atlanta’s skyline that will have a pool, private dining rooms, and cabanas for its members, as previously reported by AFROTECH™.

Gaining Investors One At A Time

TGS has raised $30 million in funding at the time of this writing, with investors including T.I., Big Sean, Charles Barkley, Cam Newton, Baron Davis, Will Packer, and more. In its early days, the venture was not initially understood by investors. Wilson reveals that he received a series of rejections before his first yes.

“It was terrible. We pitched 97 times before the first person said yes. We thought we needed a million-dollar raise, ended up being north of $3 million,” Wilson said in an exclusive chat held during the 2025 AFROTECH™ Conference.

“A lot of times folks will talk about a burn rate where you have cash to lose money for a while. We spent all of the money that we had raised building out the location, and from that minute on had to figure out how to survive from that moment. I didn’t pay myself anything for two years. It was really ugly for the early days,” Wilson shared.

While recognizing the rough path of entrepreneurship, he said failure never preoccupied his mind.

“Failure is going to come, I will deal with it when it’s there. Failure might be right outside of this room … If you become preoccupied with the idea of how you’re going to fail, when you’re going to fail, I think that enhances the chance … I think too much of the entrepreneurial startup talk has this obsession with talking about what if it fails. Well, there’s always a risk of that, but you got to play to win and not lose,” he mentioned.

Embracing Community

TGS now has nearly 10 years of skin in the game, which Wilson is grateful for. His team has stood behind the business since its inception, weathering the pandemic, the 2023 reacquisition after ending its deal with Greenwood the year prior, and continuing to do so in today’s landscape when many are in dire need of community.

“We haven’t redefined what the word community means, but we are being super intentional about living out what it actually requires to be in real community with people, which is showing up, which is understanding that there are things that we’re going to have to work through,” Wilson mentioned.

“This moment is a really critical one. And I’m as clear about why we do what we do as I’ve ever been, because for us to make it through — which I’m confident that that will happen too — but for us to make it through, it’s going to require us to be in relationship with one another,” he added.

The Gathering Spot’s vision will continue to remain rooted in community and culture. Wilson acknowledged he is privileged in having a business that is powered by his community and that does not have stakeholders in meaningful percentages to dictate how the business operates. He carries a strong sense of urgency, a spirit he credits to his upbringing in the church, where he learned the importance of being responsible to one another.

“A lot of organizations don’t have that privilege. They have government grants that are being threatened. They have companies that are reevaluating their policies and procedures and are shifting their funding … I’m not doing that,” Wilson expressed.

“I’m engaging the folks that have always kept TGS alive and I’m not again being apologetic in any way, shape, or form about what we believe and why we believe it and who we serve,” he added.

Wilson Returns To The AFROTECH™ Conference

Wilson understands we need to protect spaces that are safe havens for the Black community. It’s why he also has returned to the AFROTECH™ Conference during a time when it almost seems like a radical act for Black professionals to decide to convene. However it is necessary.

“I’m going to keep coming back because this now, in its ninth year, is a tradition that we have to protect. And I don’t see it any other way. It is beautiful to see, especially in a time period where there are so many external forces that are trying to stop and question and defund this sort of effort happening,” he acknowledged.

“It is an intentional, borderline radical act to say, ‘No, I’m going to go be in community with my folks. And we’re going to go and make sure, for professional reasons and social reasons and whatever else, that this is a meaningful time for us to be together. I’m glad to be here and I hope that everybody invests and protects this institution,” he said in conclusion.

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