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Bobby Simmons

Owner of Society 2201



Born and raised in Chicago, Bobby Simmons continues to make his unmatched mark on the city, even after his 11-year career in the National Basketball Association (NBA). Growing up in the Altgeld Gardens housing project, Simmons was a product of his community – in a favorable way. Not only did his mom and dad raise him along with his five siblings, but he also built essential relationships with neighbors, coaches, teachers, and parents of other athletes. These loved ones supported, encouraged, and disciplined him to stay on a path opposite of the neighborhood norm. 

Cementing a high-profile protégé reputation during his teenage years, Bobby thrived at the sports powerhouse Simeon Career Academy High School. He then went on to play at DePaul University, which earned him a 2017 Hall of Fame recognition. Simmons was also inducted into the 2015 Illinois Basketball Association (IBCA). Playing internationally for the U.S. Men’s team, Simmons earned two gold and one silver medal. Undoubtedly, the game of basketball and the firm foundation of family and community has heavily impacted Simmons' success. 

Passionate about basketball and feeding off the desire to constantly compete and be the best, Simmons excelled. His pinnacle career allowed him to play in the NBA for the Milwaukee Bucks, New Jersey Nets, and San Antonio Spurs. He also played with “the G.O.A.T”  Michael Jordan while on the Washington Wizards. In addition, his defense skills guarded the late Kobe Bryant along with a host of other legendary players. Earning a starting position with the L.A. Clippers, he received the 2005 NBA Most Improved Player Award. A testament to his nature, Simmons always wants to improve his life and the lives of others – he never settles for anything less than excellence.

Post his NBA career, as a successful businessman, Simmons has learned and now teaches the importance of responsibility, accountability, and taking advantage of opportunities. Paving the way for others, he shares his challenges, triumphs, lessons, and blueprints to best assist clients in creating personalized career plans and post-basketball transition strategies.He advises nearly 450 mentees and serves as a Career Development Counselor for the National Basketball Players Association (NBPA)

Driven by basketball, fashion, and athletics, Simmons partnered with Lavelle Sykes to create Succezz in 2008. Located in Chicago’s South Loop, this dynamic duo attracts worldwide sneakerheads. For the past 12 years, customers have continued to frequent the designer sneaker boutique for rare commodities. 


Though Bobby has an extroverted personality, he loves entertainment and camaraderie.  Established in 2012, this visionary entrepreneur also owns an exclusive events venue located in Chicago’s West Loop called Society 2201. Guests enjoy a palette-friendly champagne list, customized drinks, and a renowned atmosphere radiating state-of-the-art experiences. No matter the endeavor, whether it's real estate, philanthropy, business, boards, or basketball, Simmons is devoted to leaving a positive mark and being a part of notable communities. Honored as the 2021 Omega Psi Phi Man of the Year, Simmons will forever build a path for those coming after him. He continues to reside in Chicago with his three children. 

Follow Mr. Bobby Simmons on social media networks-

Instagram: @succezz  or LinkedIn: Bobby Simmons

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