Facing that quandary, Alter decided a shift in strategy was necessary. In short, he told GlobeSt, the Alter Group will move away from being a private developer that funds its projects with family money, and more toward becoming a diversified investment firm that teams up with outside capital.

“We will move from an operating development company to being a diversified real estate investment firm,” he said. “This will include investing in ground-up development, acquisitions, opportunistic real estate plays and even in other real estate companies.”

It's a way, says Alter, to both get most of his family's money out of the business, while spreading the firm's risk profile. It also simplifies the business in terms of future planning.

Plans also call for the disposition of a bulk of its portfolio, including buildings in Chicago, Northern Virginia, Phoenix and Florida. Downsizing efforts have begun—the firm's development staff of 50 have been offered retirement and severance packages, though the 65-member Alter Asset Management will not be impacted.

“This will be a very careful, considered transition over the next 24 months,” said Alter. “We have spent a great deal of time discussing this internally in order to make sure that we honor the legacy of the company while priming the firm for a productive new era.”

These types of decisions, Alter pointed out, aren't unique to his firm. Many family-run companies in the industry are faced with these issues, especially if it's third-generation—“Typically the second generation follows in their fathers' footsteps, but it's very rare that the children of the following generation want to go into the family business.”

In an ideal world, Alter says he'd love for at least one of his potential successors to change his or her mind. Yet he isn't despondent over the situation—“It is what it is. All we can do is prepare for the future, reshape the company and enter into a new phase.”

On the upside, Alter's bringing product to a seller-friendly market, and the firm's properties will likely be well received. Among the first to hit the sales block is 111 W. Illinois St. in the River North submarket, according to Crains Chicago Business. The 10-story, 228,000-square-foot property is 90% occupied, more that half of it by Salesforce.com.

The firm also has a hefty potential development pipeline of 1,057 acres of land across the country. The bulk of it, about 700 acres, is in Chicago—specifically, 641 acres in the Grayslake submarket, where it is looking to kick off a massive mixed-use development called Cornerstone next year.

Investing in burgeoning or entrepreneurial companies isn't new to Alter, who has invested his own capital in several enterprises. In addition to being the principal owner and chairman of the Chicago Sky WNBA team and formerly a partial owner of the New Republic, Alter has invested in Entrust Realty Advisors, an investment advisory firm that has completed more than $1 billion in dispositions; Alter+Care, a healthcare real estate development firm which has developed two million SF of medical office buildings; Alter Asset Management, a property-management company that will continue to serve third-party owners; and Alter 360, which provides turn-key brokerage services to entrepreneurial businesses and small property owners.

His philanthropic activities include being founder and president of City Year Chicago, whose signature program is the City Year Youth Service Corps. The goal in the program is to bring together approximately 1,000 people ranging in age from 17-24 from diverse backgrounds and put them through a full-time commitment of a year of community service, leadership development, and civic engagement where they mentor children.