Joe Macchione has always been a deal guy. From his time at Morgan Lewis & Bockius to his role as general counsel at public company GMH Communities Trust, he had a mind for business and an entrepreneurial spirit to match.

But he was still a lawyer, after all.

The battle between his legal mind and business acumen was truly put to the test when in 2008 GMH Communities was sold, and private company GMH Associates was created in its place. Chief Executive Officer Gary M. Holloway needed a new chief operating officer for the much smaller, 50-plus-employee company. And longtime general counsel Macchione was his man.

It's hard enough to make the transition from lawyer to general counsel, Macchione said.

Attorneys are used to focusing in on one aspect of a matter for their clients and as GCs they have to focus on the broader picture. He said it becomes almost a "paralysis by analysis" effect, in which the general counsel is afraid to make any decisions.

Transitioning into a purely business role requires an even broader mind and is a tougher leap to make, Macchione said.

As a COO, he is really tasked with the functionality of the business, its operations and the management of people. Those aren't things lawyers are accustomed to doing, he said.

"I try to balance it," Macchione said. "I try to keep 50 percent of my thought process on studying and analyzing the risks and the other 50 percent emphatically focused on trying to get the deal done."

And now that he has had a taste of the other side, he says it has become even clearer the stigma business folks attach to the legal perspective. Macchione was at a recent board meeting in Austin, Texas, for American Campus Communities -- the company that bought the student housing portion of GMH Communities Trust. As part of the sale, Macchione joined ACC's board. He said one of the other board members was talking about a deal she was working on where, she said, "unfortunately on the other side it was being run by a lawyer."

"What I take from that when I hear that is that most lawyers are not trained to accomplish a deal," Macchione said. "They are there to study risk, and you can't blame them for that."

So does that mean Macchione is always understanding of GMH Associates' new general counsel, Jim Kennedy? Well, as much as he'd like to think so, not all the time.

Although he said he thinks he tends to respect and remember his roots, Macchione admits it's sometimes frustrating as a COO to work with the person who is now the lawyer. That's when he knows he's a true business guy.

Macchione and some of the other business folks have even come up with an affectionate nickname for Kennedy -- director of deal prevention. That definitely wasn't a moniker attached to Macchione when he was GC, he joked. But Macchione is quick to point out how good Kennedy is at his job.

"I do remember where I came from, but sometimes you get frustrated by the legal mentality," he said.

But if he does, he must hide it well.

Kennedy said it has been a real bonus to have someone in the COO position that has been in the general counsel seat and knows there are certain issues that need to be discussed with counsel.

"He's more understanding with my perspective on things and the issues I raise," Kennedy said.

And Macchione is also a good sounding board. Now that the company is private and roles are less tightly defined, Kennedy is much more involved in business-related meetings and decisions.

Kennedy said he has a pure legal background and isn't always as business-minded as Macchione. He said Macchione helps him focus on both the legal and the business side so that he doesn't fall into the "director of deal prevention" category -- a name he joked he hasn't been called in at least a year.

And Macchione gets his own lessons, too.

He said Holloway has been in business a lot longer than him and has been instrumental in transitioning Macchione from GC to COO.

"I find that I pigeonhole my thoughts sometimes and it takes Gary to step in and look at what I'm doing and say, 'Hey, Joe, think about the bigger picture here,'" Macchione said.

If Macchione had to give advice to anyone transitioning from legal to business, he said, it would be to embrace, respect and learn about all aspects of the business. There needs to be an understanding of how they function and how each department relates to the overall strategy.

In a sense, that makes the switch even more difficult because Macchione has to do his own job and learn that of everyone else too, he said.

TESTING OUT THE NEW ROLE

Though much smaller than its public company predecessor, GMH Associates handles the ownership and management of several multi-family and conventional housing units and has a number of subsidiary businesses as well.

Holloway sold the public company in 2008 for $1.75 billion just before the real collapse of the economy. And even though they soon after saw the decimation of the residential mortgage business, newly minted GMH Associates also saw a huge opportunity, Macchione said.

While many companies were getting out of the mortgage business, GMH started a mortgage division from scratch with GMH Mortgage Services.

The goal is to continue to own and operate other companies related to the residential real estate market. GMH Associates currently has a large equity position in a residential alarm monitoring company, Security Networks.

Macchione said GMH is out there looking to expand those interests through the purchase of new companies. The current market has sometimes made that goal difficult, he said.

The reason GMH Communities Trust went public in the first place, Macchione said, was to take advantage of additional financing opportunities. But there are also difficulties in running a real estate venture as a public company. The industry isn't meant to be studied on fiscal quarters, he said, so there is a lot more time invested on non-revenue generating aspects of the business, he said.

"Not being public enables us to get back to being the entrepreneurs that we were before going public," Macchione said.

In terms of financing, the company doesn't see being either public or private as being more advantageous in this market. Macchione said private equity companies are still sitting on the sidelines waiting for distressed opportunities. But for the entrepreneurs at GMH Associates, going private was definitely the right move.

Not to mention all of the rules and regulations that are now governing many public companies, he said. At GMH Communities, 12 to 15 percent of the company's annual expenses were related to it being public, he said.

"[Being private] allows you to paint the brush outside of the lines," he said.

That's what he did as an attorney. That's what he does as the deal guy.

This article originally appeared in GC Mid-Atlanticmagazine, a publication affiliated with The Legal Intelligencer.