Entrepreneur Steven Hobbs Sr. has a bold plan to revitalize Kimbark Plaza, starting with the former Leona’s Pizzeria.
Having secured rights to use the former restaurant from Kimbark Plaza board co-president Charles Newsome, Hobbs said the space is now open for event rentals at low or no cost. Hobbs himself has also unrolled a new pop-up venture in the former Leona’s dining room: the VE (Virally Entrepreneurial) Lounge.
“With all the new developments east of us, we also want to give back to the community,” Hobbs said. “We want this space to be used by people who may not have the money for proms and graduations, but who want a nice place, who want to roll out the red carpet.”
Hobbs is responsible for securing the Amazon Lockers already in Kimbark Plaza and hopes to build on this momentum in the coming months. With the VE Lounge, he hopes to promote artificial intelligence (AI) adoption in Hyde Park.
At a VE Lounge AI pop-up event held at the vacant restaurant in April, Hobbs encouraged guests to interact with two AI avatars he designed, named VE and Kimi.
After scanning a QR code with his phone, Hobbs showed off the two AI assistants in one of Leona’s wooden booths. VE appeared and responded to Hobbs’ questions about the purpose of the new venture.
“I’d be delighted to share more about the Virally Entrepreneurial Lounge,” VE said. “Overview. The Virally Entrepreneurial AI Lounge is a dynamic virtual space designed to foster creativity, innovation and community among entrepreneurs, gamers and creators. Our goal is to provide a hub where individuals can collaborate, learn and grow using cutting-edge AI tools and resources.”
VE said that the lounge would offer workshops and training sessions, along with AI-driven video editing and music instruction.
“If you’re vibing with the idea of having a virtual assistant with you at all times, think of me as your jazzy, entrepreneurial version of Alexa,” VE said.
Hobbs acknowledged that while many are skeptical of AI, people in the neighborhood he’s spoken with have changed their minds as soon as they’ve used it.
“I’ve had seniors see what it can do and just say, ‘Wow,’” he said. “I have a friend who’s a sheikh with the Moors. He was a skeptic at first too, but now he uses it to help him write speeches.”
Hobbs designed VE Lounge’s other AI avatar, Kimi, specifically for Kimbark Plaza, for which it is named. In pictures, Kimi is represented as a robot clad in glowing blue armor, with large blue eyes and long eyelashes.
Hobbs demonstrated how it might benefit plaza shoppers by saying, “Hi Kimi, I want a 2 o’clock reservation at the nail shop, and then at 3 o’clock, can you order me Harold’s Chicken? And at 8 o’clock could you purchase two tickets at the movie theater?”
A rendering of Kimi, an AI avatar named after Kimbark Plaza designed by Hyde Parker Steven Hobbs Sr.
Hobbs’ AI pop-up venture reflects his long history of entrepreneurship on the South Side. His mother Barbara A. Johnson and stepfather Albert Johnson once managed the Parkway Gardens housing complex, along with dozens of other South Side properties, both public and private. Albert Johnson was once the president of the National Association of Real Estate Brokers, and Barbara Johnson was once vice president, as well as president of Dearborn Real Estate Board. Both fought for equal housing opportunities for African Americans, Hobbs said.
Hobbs himself entered the realty business young, when at age 15 he was tasked with slipping five-day eviction notices under the doors of tenants of the properties his family managed.
While studying at the University of Alabama in the late 1980s, Hobbs became the first African American to intern at the Alabama Chamber of Commerce. After a stint at Kodak Cameras, Hobbs re-entered the realty trade, working with mortgages for PNC bank and later opening a realty business of his own in the Hyde Park Bank building called Investment Options LLC. He is an energetic founder and a great AI enthusiast.
Drawing on his knowledge of real estate, Hobbs recently launched an educational video series called “Mortgage Masterclass,” which is led by AI instructors. Hobbs also founded an esports platform called “Airport Gamer” which previously enabled O’Hare travelers to play online games. Business was good, Hobbs said, until the war in Ukraine disrupted his connection to the Russian company that hosted the company website, forcing him to take the platform down.
Steven Hobbs Sr. scans a QR code to demonstrate how to use VE, the Virally Entrepreneurial Lounge’s new AI assistant, on May 8, 2025.
Hobbs’ choice of the “Virally Entrepreneurial” title reflects his restless experimentation in business, as well as his penchant for audacious names, which stretches back to his college days, when he founded a male modeling troupe called “Sophistication Unlimited”.
Hobbs aims to bring this audacity to Kimbark Plaza, which has experienced difficulties in the recent past, with the closure of Leona’s in 2023 and the ongoing challenges faced by Hyde Park Produce, which has struggled to recover following a small fire in 2024. Nearby, however, the recently opened Jerk Yard was full of patrons, and paintings by its chef Marcel Terry are proudly featured in the Leona’s dining room.
Hobbs hopes other businesses can follow suit and usher in a Kimbark Plaza renaissance. As for his vision for the former Leona’s space in particular, Hobbs said he wants neighbors to come in, learn about AI, host events, and with time, attract a permanent establishment that is “epic, legendary and iconic.”
Those interested in renting the VE Lounge or in scheduling an AI consultation can send inquiries to Steven Hobbs at [email protected]
