Howard Tullman stands in front of Mission Posey: Hyacinth Arsonist, a painting by Thomas Woodruff valued at $6,000 to $8,000. Photo: Mike Reinders

Howard Tullman is best known as a tech entrepreneur, but he’s also a noted art collector. Visitors to his Milwaukee Avenue gallery were mesmerized over the years by the colorful portraits and surreal imagery that highlight much of his collection.

Now, Tullman is selling the gallery space and relocating the collection. (He's given many pieces away, including to museums and the 1871 Chicago space—and his grown daughters can only take in so much.) On Oct. 30, he’ll auction off 200 pieces from his 1,600-piece collection of eclectic art, portraits, nudes, and sculptures.

Leslie Hindman Auctioneers is handling the event. Proceeds will benefit Tullman’s family foundation, which provides stipends and scholarships to art students, donates to museums, and funds special events.

Culling the collection has been a lengthy process as Tullman and his wife, Judy, see each work as special. “When I first made the list, she looked at a few and said, ‘Over my dead body.’ So I adjusted it,” he says with a chuckle.

Among pieces up for auction: Naughty Betty by Donald Roller Wilson. It’s colorful and features a smiling monkey wearing a crown made of roses. It’s also by a living artist, which is a hallmark of his collection.

Naughty Betty has an estimated value of $10,000 to $15,000. Photo: Courtesy of Leslie Hindman Auctioneers

“All of the pieces are special because of the artists,” says Tullman, who had developed lifelong friendships with many of the artists whose work he holds dear.

Works by well-known artists are in the mix, too, including the late Herb Ritz's True Blue featuring Madonna. It's estimated to go for $2,000 to $4,000, and the entire auction is expected to draw $500,000 to $1 million.

Along with the works themselves, Tullman’s name as owner will be a draw for potential buyers, says Zack Wirsum, director and senior specialist of fine art at Leslie Hindman Auctioneers. “Howard’s name and his various entrepreneurial pursuits and the impact he’s had on Chicago all add cachet to what’s being sold,” Wirsum says. “It makes each piece more desirable.”

The auction comes as Tullman prepares to step down as CEO of the 1871 entrepreneurial center. He will remain on the board.

The sale of his gallery space closes another chapter: The neighboring Intuit museum is buying the property. It’s a nice fit, says Tullman. "I'm glad it's going to the museum."

For the 20 years he’s owned the space, it’s been a refuge where he writes. It's also a hip gathering spot for art students studying portrait work and friends. A fundraiser for Hillary Clinton was held there. The late Harold Ramis and fellow actor John Cusack laughed together at a dinner party amid the collection of nudes and pop art. And Rahm Emanuel lived in a portion of the 5,000-square-foot gallery while he was running for mayor back in 2010.

The catalogue was released today, and the auction is online only. The exhibition is open for display by appointment.

Starving Bourgeois by Jim Lutes has an estimated value of $8,000 to $12,000. Photo: Courtesy of Leslie Hindman Auctioneers
Coma Dent by Karl Wirsum is over three feet wide and long, and has an estimated value of $10,000 to $15,000. Photo: Courtesy of Leslie Hindman Auctioneers
Beach #120 by Hilo Chen, oil on canvas, is valued at over $8,000. Photo: Courtesy of Leslie Hindman Auctioneers
Elwood Grill #2 by Robert Gniewak was created in 2003 and estimated to be worth $10,000 to $15,000. Photo: Courtesy of Leslie Hindman Auctioneers