Ryan Wilson: 97 Rejections, Zero Failure

Imagine rejecting nearly 100 potential investors before finally getting a ‘yes.’ That was the reality for Ryan Wilson, founder of The Gathering Spot (TGS). Despite the daunting number of rejections, Wilson’s mindset was never about failure, but about the unwavering pursuit of his vision.

From Georgetown Law to Entrepreneurship

After graduating from Georgetown Law, Wilson turned down a lucrative job offer at a law firm to pour his energy into The Gathering Spot. Founded in 2016 with TK Petersen, TGS started in Atlanta as a private membership club designed to foster connection and opportunity for entrepreneurs, creatives, politicians, and executives.

The club has since expanded to Chicago, New York City, and Detroit, offering members co-working spaces, event venues, and full-service restaurants and bars. Their most ambitious project, The Retreat, is a massive 60,000-square-foot space near Atlanta’s skyline, featuring a pool, private dining, and cabanas.

The Grind of Gaining Investors

Securing funding for TGS, which has now raised over $30 million from notable investors like T.I., Big Sean, Charles Barkley, and Will Packer, was a challenging journey. Wilson revealed during the 2025 AFROTECH™ Conference that they pitched 97 times before receiving their first ‘yes.’

The initial $1 million raise they sought turned into over $3 million. In the early days, they invested all their raised capital into building out the physical location, leaving them with no personal income for two years. “It was really ugly for the early days,” Wilson admitted.

A Mindset Focused on Winning

Despite the immense pressure and financial strain, Wilson’s mindset remained focused on the goal. “Failure is going to come, I will deal with it when it’s there,” he stated. He believes that becoming preoccupied with the possibility of failure actually increases the likelihood of it happening.

You got to play to win and not lose. — Ryan Wilson

Wilson advocates for a proactive approach, emphasizing the need to “play to win” rather than dwelling on potential setbacks. This philosophy has been crucial in navigating the unpredictable landscape of startups.

The Power of Community and Urgency

Now nearly a decade old, TGS has weathered challenges like the pandemic and a reacquisition. Wilson credits the business’s survival to the team’s commitment to “real community,” which involves showing up for each other and working through difficulties. He feels a strong sense of urgency, a value instilled by his church upbringing, emphasizing responsibility to one another.

Unlike organizations reliant on potentially threatened government grants or shifting corporate funding, TGS is powered by its community. Wilson is unapologetic about his commitment to serving that community and upholding the values that have kept TGS thriving.

Protecting Black Professional Spaces

Wilson’s continued participation in the AFROTECH™ Conference, even when convening feels like a “radical act” amidst external pressures, underscores his dedication to protecting safe havens for the Black community. He sees AFROTECH™ as a vital tradition that must be protected and celebrated.

His message is clear: investing in and protecting these institutions is essential for professional, social, and personal growth. He encourages everyone to secure their tickets for future AFROTECH™ Conferences to continue building and supporting this vital community.