Wolstein went to work at a young age, and held down a series of jobs while attending local public school: Selling copies of the Cleveland Press newspaper, stocking shelves and working as a cashier at his aunt's store, working as a soda jerk at various local drugstores, selling hot dogs and soft drinks at League Park (a baseball stadium in Cleveland),[3] cleaning home furnaces, shoveling snow from driveways, and selling Christmas trees.

[8] He was enterprising, and once made money by selling cold soft drinks from his toy wagon to construction workers building new homes across the street from where he lived.

"We were Depression babies, and no matter how much we have or the rare experiences we have encountered along the way, our roots will always be in Cleveland's old Jewish working class neighborhood, Tuscora Road.

[1] Still debating what to do with his life,[3] Wolstein enrolled in the accounting program at Cleveland College, an adult education institution jointly operated by Western Reserve University and Case School of Applied Science,[8] paying for his education by working part-time coordinating subcontractors for a local building firm.

He attended classes at night[11] while working full-time for Kalamazoo Appliances,[8] Harold Shur's home heating and air conditioning business.

Wolstein helped build his first shopping center, the Great Northern Mall in North Olmsted, Ohio, during his tenure with the firm.

In 1964, one of Wolstein's firms, Scott Construction, received a $725,000 loan ($2,700,000 in 2023 dollars) to build a 350-home development in Twinsburg, Ohio.

[12] The project was so financially successful that Wolstein closed his law practice and began concentrating solely on real estate.

[4] Wolstein set a goal of constructing five malls, but his business proved so successful that within 15 years he'd built 150 shopping centers nationwide.

[12] Developers Diversified ended its relationship with Kmart in 1980, but continued to build shopping malls around large anchor tenants such as Home Depot, Kohl's, and Wal-Mart.

[14] In December 1992, Developers Diversified filed to become a publicly held real estate investment trust (REIT).

[15] The move was prompted by a nationwide credit contraction that had severely limited Developers Diversified's ability to engage in new projects.

[3] The company, now known as Developers Diversified Realty Corp. (DDRC), went public in February, listing its shares on the New York Stock Exchange.

Having spent most of his life as a freewheeling maverick who operated on hunches and personal relationships, he had become frustrated having to subordinate his decisions to those of a board of directors and stockholders (many of whom had no experience in real estate development).

[18] Wolstein had also retained ownership of 7 acres (28,000 m2) of land on the east bank of the Cleveland Flats,[19] and intended to use Heritage Development to begin designing, constructing, and operating a wide range of restaurants, bars, dance clubs, and music venues there.

Wolstein also expressed interest in building an industrial park in Twinsburg on property he owned there, as well as getting back into the residential housing market.

[20] The company also developed the Bertram Inn and Conference Center and The Marketplace at the Four Corners Shopping Center in Aurora;[5] the Moen Inc. office building in North Olmsted; the Macedonia Commons mall in Macedonia, Ohio; and the Creekview Commons mall in Brecksville, Ohio.

Wolstein suggested using the disused, 50-acre (200,000 m2) Norfolk Southern rail yard near the Jacobs Field baseball stadium.

[31] In 2004, when Major League Soccer made a two-team expansion, Wolstein signed a letter of intent to buy one of the franchises and base it in Cleveland.

Wolstein was bidding against three others: Al Lerner, billionaire owner of MBNA, the nation's second-largest issuer of credit cards; Charles Dolan, founder of HBO and the Cablevision cable television service, and his attorney brother, Larry Dolan; and New York City banker and real estate developer Howard Milstein.

[34] On September 8, 1998, the NFL sold the Cleveland Browns franchise rights to the Al Lerner group for $450 million ($725,900,000 in 2023 dollars).

[35] Wolstein was a frequent supporter of a number charities and nonprofit organizations throughout the greater Cleveland area for most of his life.

The organization used the money to finish a new rehabilitation and workshop center, which it named the Bart and Iris Wolstein Building.

[37] The Wolsteins made a $1.5 million ($2,700,000 in 2023 dollars) donation in 2000 to renovate the three-story bell tower at Ohio State University.

[11] In 2002, the Wolsteins donated $1 million ($1,700,000 in 2023 dollars) to renovate Sycamore Hall at the Weatherhead School of Management at Case Western Reserve University.

[41] In 1946,[8] Wolstein was playing touch football in Cain Park in Cleveland Heights when the ball landed at the feet of Iris Shur.