Career Alternatives for Attorneys: New England Innkeeper

Welcome back to our occasional series on career alternatives for attorneys — i.e., things you can do with a law degree that don’t involve working for a law firm as an associate or contract attorney. If you feel like your knack for being hospitable is wasted in the law, you might be interested in this alternative.
Rob Gregor was an attorney in the New York office of Paul Weiss until April of this year, when he quit to head north. One of the partners to whom he sent his departure e-mail responded to say that he had the best excuse ever for leaving the firm: becoming an innkeeper in Maine.
Gregor is now the owner of the Herbert Grand Hotel, a 27-room historic inn in the small ski town of Kingfield, Maine. Gregor wrote to us: “The town has a population of about 1,100 and I have become BigLaw’s version of Bob Newhart.”
So how does one go from dealing with SEC complaints to dealing with plumbing leaks for a hotel built in 1918? Find out after the jump.


We talked with Rob last week about his transition from barrister to hotelier. When we called, he was in the middle of a crisis: there was a leaking pipe in the old inn. “I’m always fixing something,” he said. “But my crises used to involve the SEC instead of water leaking.”
Rob’s transition to the hospitality industry was not completely random. He studied at Cornell’s School of Hotel Administration and spent five years working at hotels after graduating from college in 1999. He developed an interest in politics and decided to go to law school, first at Albany Law; he then transferred to Cornell, receiving his J.D. in 2007.
He started working at Paul Weiss but lasted only 19 months. He didn’t mind the hours. They’re similar to the hours he works now — he even lives at work, making his home in one of the inn’s 27 rooms — but he didn’t like being a Biglaw cog. “The success rate for becoming partner was so low, and I knew I wanted to be in business for myself,” said Rob.
He hadn’t set foot in Maine before January, when he went to check out the inn. He’s loving the new career. The only thing he misses is “the intensity” of New York and Paul Weiss. “That drive just doesn’t exist in Maine,” said Rob.
So how does a Biglaw attorney afford an historic inn?

It was an SBA deal. The primary lender floated 50% of the loan, the SBA floated 30% of the loan and I put up 20%. The total purchase price was $625,000….
I do have student loans, but I worked 35-40 hours per week during law school, so I was able to hold off on the private loans. Nonetheless, I [am still making loan payments each month.]…
I was pretty naïve when I started at PW. I thought that I would get fired in the first month so I hoarded my paycheck (i.e. no bar trip, lived in NJ, solicited enough work to guarantee that I would be in the office late enough to get a free dinner and a car ride back to the garden state). By the time I realized that I was doing well as an associate and that I was not going to be fired, I had amassed some money and frugality became a way of life. Not sure if this helps anyone else, but it worked for me.

He said there’s one big similarity between Biglaw and the innkeeper’s life. “Delegate, delegate, delegate, and hope nothing explodes,” he said.
Rob may be operating a historic inn, but he’s all about the new media. The Herbert Grand Hotel has a Facebook fan page.

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