Bobby Simmons has been cultivating a career beyond basketball since Day 1

Simmons and business partner Lavelle Sykes founded Succezz in 2008, and four years later Simmons opened his second business, Society 2201, a nightclub in West Town.

SHARE Bobby Simmons has been cultivating a career beyond basketball since Day 1

Bobby Simmons and Lavelle Sykes opened Succezz in 2008 and in 2018 moved their storefront location to 2214 South Michigan Avenue.

Annie Costabile/Sun-Times

Bobby Simmons spent 10 years playing for five teams in the NBA, but his post-playing career was always at the forefront of his mind.

Growing up in Chicago, Simmons learned early that his education would take him farther than his skills on the court ever could and that the game was just a means to an end.

“This mentality was embedded in me as a kid growing up in the projects of Chicago,” Simmons said. “As a kid, I always wanted more.”

After graduating from Simeon and playing three seasons at DePaul, Simmons got one of the best educations he could have dreamed of by playing alongside Michael Jordan with the Wizards during Simmons’ first two seasons in the NBA (2001-03).

Jordan and Simmons shared the same trainer, Tim Grover. Workouts started at 6 a.m., and the two would play pick-up games in the evenings. Jordan always picked Simmons to be on his team. Without even realizing it, Simmons said he was picking up a business mentality from Jordan.

He remembers watching as Jordan took business calls and got work done on his computer before games. Lessons such as remembering that the early bird gets the worm, being consistent and holding yourself accountable transcended basketball.

But it wasn’t until Simmons was playing with the Bucks that he put those lessons to use off the court.

“When I got to Milwaukee, the name Junior Bridgeman kept coming up,” Simmons said of the former Bucks player and current businessman. “As I did more research, I thought to myself, ‘Wow, this guy is very influential.’ He showed me it can be done. You have to utilize your platform while you have it.”

Simmons was able to meet with Bridgeman, who gave him the confidence that an opportunity to open his own business was there. He just had to pursue it.

When an ankle injury forced him to sit out the 2006-07 season, Simmons looked at it as an opportunity instead of a setback. With nothing to do but rehab and sit at home, Simmons began brainstorming his business plan.

Long before he began his professional career, Simmons was just another Chicago kid inspired by the sneaker culture that intertwined with the basketball world. He had an extensive sneaker collection, and that became the inspiration for his next venture.

“I called my partner, Lavelle Sykes,” Simmons said. “Actually, you know what, he called me, and we collaborated on what we wanted to change in our community and for the city of Chicago.”

“We saw a void in Chicago,” Sykes said. “At that point, there were not a lot of minority-owned sneaker stores in Chicago. So we said, ‘Why not us.’ ”

Simmons and Sykes founded Succezz, a sneaker and fashion boutique, in 2008. The two Z’s stand for no sleep, and their first storefront location, which they occupied for 10 years, was in the South Loop. Four years later, Simmons opened his second business, Society 2201, a nightclub in the West Town neighborhood.

Even with over a decade’s worth of ownership experience, nothing prepared Simmons for how the coronavirus pandemic would affect his businesses.

Simmons, like business owners across the country, was forced to close both of his establishments in March. Simmons is unsure when he’ll be able to reopen Society, but is having the nightclub cleaned regularly in preparation for that day.

Despite the shift to phase 3 of the Chicago’s reopening plan beginning June 3, Succezz will remain closed to in-store customers.

“I want everybody to remain safe,” Simmons said. “We’re really a small, small business and I don’t want to risk anybody getting sick. So for now we’re going to keep things the way they are.”

During the stay-at-home order, Succezz business strategy shifted from appealing to customers walking past its window displays to solely focusing on social media and their website presence. Sykes said their staff keeps the website immaculate, just like the store.

Simmons and Sykes have been employing a small staff to unpack shipments and help mail online orders. Beginning June 1, Succezz will offer curbside pickup. All employees are wearing masks and gloves for the duration of their shifts.

The remaining staffers at Succezz are still being paid despite not being able to work in the store. Simmons and Sykes felt it was important to let their staffers know that they are taken care of and that the Succezz team is a family.

“It’s not about us, it’s about our team,” Sykes said. “So, once we come back around and this all passes everybody will come back hungrier and happier.”

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