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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Great. One less lawyer looking for a job in big law. Good luck in Maine.
This sounds pretty cool. Better than the cupcake truck guy.
Big Law's Bob Newhart? Does he have a wry, unassuming sense of humor? Does he know how to cope with Larry, Darryl & the other brother Darryl?
How can he just make a statement like that? Anybody can be an innkeeper. Not just anybody can be Bob Newhart.
Am I wrong?
3- you're statement that anyone can be an innkeeper is wrong. It takes a certain personality to do it well and enjoy it and make a decent living. As for his similarity to Newhart - I liked the analogy, not withstanding the low probability that he will have Larry, Darryl and the other brother Darryl to contend with on a regular basis.
All in all, I say good for him. He'll be much better off than those of us who try to stick it out in big law.
-working on my own exit strategy
Sounds more like Lorelei Gilmore than Bob Newhart to me.
Does he have any room for deferred associates to work there for the next year? Call me.
SMU Rules!!!
Word of advice for the innkeeper: DO NOT rent out your room to David Lat and Elie Mystal, especially if they ask for an hourly rental.
Fail to heed my advice, and you will wind up with a hotel filled with disturbing slurping sounds, sort of like when you use a plunger, and a hotel room that smells like anal sex, which in this case means digested filipino food.
I am an associate at Squire Sanders. My wife is beautifuI. I attribute my incredible success to my education at the Fisher College of Business.
What a crock. Even if he saved EVERY after tax dollar he made for 19 months he would not have had a 120K down payment, closing costs and working capital. I suspect an inter-generational transfer of cash.
10,
Middle class hater!!!!!
10,
If he saved every dollar, he would have made at least $80k a year. Second grade math.
12--
$80,000 per year over 19 months = 126,666.67. He already admitted he had student loans and didn't live in the office. No way he made it on that.
12=first grade drop-out.
--Not 10
The problem is that a B&B in Maine rests on the economy, namely, spendthrift gay couples, and even they're cutting back in this economy.
#3 -- doesn't matter. it was all a dream, brought on by too much Japanese food. Bob's still in Chicago living with Suzanne Plechette.
13,
Reread my post. It is 100% consistent with yours. 143 LSAT?
12
He also worked for a whole bunch of years, and we don't know what that was, so merely trying to figure out how much he saved at PW is partially speculation as to how he funded himself. I'm sure his prior career was a huge factor in getting the investor loans, too.
i'm finding it hard to stay alive after getting laid off as a first year
This is unrelated to the topic. I happen to be in Brazil right now on vacation and saw partner emeritus on the copacabana beach with a babe. I will upload a picture from my phone as soon as I get home. PE is a pimp on the beach.
Hey Dominos Pizza,
Nobody on Wall/Water street wants your goddamn pizza, so your whole fucktard argument as to "helping" out Main Street by giving them your shitty pizza at a better deal is just doing business as usual for you guys. Plus, you're actually hurting society by making the wretched midwestern lower middle class gain weight to their already plump retard messes of a body and life.
-Wall Street Attorney who just watched a Dominos Main Street/ Wall street commercial.
P.S. If I ever see a fucking Dominos Pizza Delivery boy on the street I'm going to use my ridiculously cut body and kick the shit out of him.
This guy worked in biglaw for a year and a half. That's not enough time to develop into a good attorney, and while he may have been a good associate, billing a lot of time, not too many second year associates are considered a suceess. How could they be? It's just too early in their development to really assess that sort of thing.
My point is, this guy was barely ever a lawyer, and had a prior hotel-related career that he returned to after a stint at a law firm. This guy's career path is not something to be envied.
While I wish him luck, it sounds like he either didn't much like the law or wasn't cut out for it. If he'd just stuck with the hotel thing instead of taking his 5 year diversion into the legal field, he'd probably own a bigger, better hotel.
He says he's Bob Newhart, but he might end up like Jack Nicholson.
I don't get it. Why even go to law school in the first place? It reminds me of this attorney that became an HR specialist. The job didn't require her to go to law school, and every time I talk to that attorney it feels like he is always trying to justify the need of a JD at his job.
19 months at biglaw = promotion from relevance to privilege. Woo-Hoo!!!!!!!!!!
24,
Now that was funny!
I bet he'll bang a few milfs.
26,
Milfs in a Maine town of 1,100? Ever see the movie Misery?
In 2002, I graduated second to last (401/403) from UC Hastings.
UC Hastings = Diploma Mill.
23 = MAJOR RETARD
28 - second to last would make you 402, not 401. How did you graduate high school?
30 = MAJOR DILDO
I heard tell they have lobster in Maine.
Lots and lots of lobster.
Lobster that sometimes one finds in peculiar places.
My drinking has gotten out of control.
-20
This is a complete croc o' shit. This guy is in no way 'using his law degree for another profession.' He merely returned to his previous shitty career fixing pipes and making gay couples crepes.
19, I don't know what is sadder, Partner Emiritus or someone trolling on his behalf.
The guy worked 40 hours a week during law school? Does that mean that you can ace law school with your eyes closed?
35,
Are you upset that you can't use your undergraduate degree, Political Science?
19 = PE, trying to create the illusion anybody likes him.
36 = PE, disappointed nobody bit on his bait.
23's friend = Post-op tranny, who may or may not be PE.
39 = PE
40 = PE.
I don't get it why would anyone quit being a lawyer? Having a law degree is tantamount to putting your finger in every pie. Yeah, biglaw jobs are cushy, but people need lawyers for all kinds of things and services don't come cheap.
My brother is an engineer. I have obtained state and federal environmental and local land-use permits, pursued deadbeat client, and the list goes on. Every problem needs a solution and lawyers are there.
Nice story. I wish him luck.
Anyhow, it amazes me that someone can transfer from Albany to Cornell.
43, all it takes is being in the top 10% of Albany. You sir are a fucking retard if your intuition didn't already suggest this to you. Nice try at being a prestige faggot.
I sharted and pussy farted on the dance floor.
-CWT 05 NY Female Associate
Dear Kash:
You really are trying to taunt us into uttering the banned words, aren't you?
A simple suggestion like ordering beer should teach everyone readily.
There is more to law than biglaw. Plenty of lawyers in smaller firms make great money.
47 - small firm lawyer wishing he was in biglaw.
Kingfield is right next to Sugarloaf, so he will get lots of skiers staying there in the winter. Nothing in the summer though (golfers?).
Having unfortunately spent time in this neck of the world, I can confidently say that this guy is going to be putting a shotgun in his mouth inside of two years. northwestern Maine is as fucking dead a place as exists in this country. There are maybe four major companies with any presence in the state. It has the second-lowest per capita income in the country. He's more than two hours from Portland (a semi-livable town of 65,000 people), and an hour from the rotting carcasses of Lewiston and Bangor (each about 35,000). Those are the major population centers of the state. If you want better food than Sbarro's, you're driving to Portland. If you want better food than Olive Garden, you're driving to Massachusetts. If you want to see an attractive person of either gender, you're driving to Boston. Once you get off the coastline, it's like driving through Appalachia. Meth and crack are EVERYWHERE. Rude Quebecois immigrants are everywhere. The women are horrifyingly ugly, and the men are fat slobs. The winters suck, and Greenfield likely has snow on the ground from mid-October through mid-April. The only store for most swaths of the state is Walmart. Auburn, Maine, has the largest one in the world. It's about the size of an Ikea - 250,000 square feet. I graduated from Bates seven years ago, and I'm still fucked up from the experience of living in Maine. A "ten" at Bates is like a 0.025 at a normal college. Two of their dorms just got condemned by the state. The academics and sports were, in all sincerity, better in my New England prep school. All in all, the place is a giant shithole.
42,
You need to up your IQ about 70+ points if you want to be a relevant flame on this comment board. Your attempt at legal humor is probably the worst I've seen.
And yet Roxana is still a failure....
My life is so pathetic I look forward to Roxana posts.
50= HILARIOUS WIN. The last time I had Sbarros Pizza was in the Detroit Airport which is an EPIC FAIL except their new terminal probably has more net worth than the city of Detroit itself.
54 = 50
I have a friend who went into the FBI after not being able to get a job in VA last year...not the innkeeper route and he loves it.
http://www.nypost.com/seven/08022009/news/regionalnews/sheep_kinned_182607.htm
Elie, please copy and paste this story and inject a racial spin to it.
56:
Is it true someone can't work for the FBI if they have ever done the whites before, or smoked pot more than 10-20 times? I've heard that.
I'm going to get me a new york slice!
I agree with what others have said that this story, while interesting and nice that he is following his dream, it is not really good advice for the rest of us. Recap: He had a career in hospitality, left it for 5 years to spend 150k getting a JD and working a job he apparently did not like, so then he went back into the hotel biz with all the money he saved from 18 months of biglaw and living in jersey.
Not if you admit it 58. Check out the website in detail because it is on there but as I recall you are basically correct, no chance of getting in if you've ever done hard drugs and even smoking weed more than a couple times may be enough to keep you out.
Great post, 50.
50 shows why people bother to come to ATL at all. Let's face it, the guys running this blog cannot write. It often feels that English is not their first language. But such sincere scorn expressed by 50 deserves praise. If only more would contribute so.
Great post, Good luck in Maine!
Does the Herbert Grand Hotel offer an ATL discount, or a discount for lawyers in general?
OY WITH THE POODLES ALREADY!
If they do ski packages -- who cares about the scenery (human and otherwise)?? The place looks beautiful, the snow will be high, and Maine really knows how to plow the main roads.
Sounds like #50 had a tough and miserable time -- a little therapy is in order.
More fun facts about Maine:
Maine is the second-least least diverse state in the nation, behind Vermont. I would have thought this would go to, say, Montana, but whatever. It never stopped getting weird going to Chinese or Mexican restaurants and seeing white, mulleted cooks in NASCAR T-shirts.
The state capital has less than 25,000 people.
The tallest two buildings in the state are a 16-story public housing ghetto in Portland and a dorm at Bowdoin.
About half the physical space in the state has no municipal services. There is an unorganized territory called Northwest Aroostook County that is 2668 square miles and is home to 27 people. This is in the county of Aroostook, which is roughly the size of Connecticut and Rhode Island put together, and has a whopping 74,000 people. There are 400 such unorganized territories in the state.
Logging companies own about 4 million acres of northern Maine.
Very eastern Maine lobbies each year to be able to join the Atlantic Time Zone, as it becomes dark at around 3:30PM in the winter – while the daytime soap operas are still playing.
The top state income tax bracket is frigging 8.5%
Lewiston is so poor that in 2002, the mayor asked the nation of Somalia to stop encouraging refugees to settle in the town, citing that social services could not support the influx of people. A few years ago, one of the more cultured locals threw a severed pig’s head into the local mosque during prayers. It’s a very cosmopolitan city. Per capita income is $17,905, and 26% of the population speaks French at home (Quebecois). Downtown had at least four pawnshops, bracketed by adult bookstores, gun stores, and about 3.5 million square feet of abandoned/closed mills. If you went into one of the downtown bars in a group of less than a dozen, you had a very good chance of having the shit kicked out of you.
As a farewell present to my college class, a high school dropout townie with devil horns tattooed into his forehead stabbed the lacrosse captain in the heart about two blocks from campus a few weeks before graduation. Perhaps not coincidentally, Bates had a chain-link fence around most of their campus until the early 1990’s.
Kudos for getting out of PW, but has anyone looked at the photos of the rooms? They look like crime scene photos. H. H. Holmes ftw?
67, your ideas are intriguing to me and I wish to subscribe to your newsletter.
Just took another look.... The rooms are nice enough and the hotel exterior is grand, but the photos really are unfortunate- recommend updating if you want to avoid giving bad vibes.
I agree with No. 50. This guy may well become like the caretaker at the Overlook hotel in “The Shining” come January 2010. Kingfield has a year round population of 1,097. While I admire his guts, Maine’s reputation as a great destination for outdoors vacations often veils the fact is that this is a severely economically depressed region. I am very familiar with this area as I often drive through and stay in towns along the Kennebec and Penobscot rivers to go white water rafting. Drive north up 201 off 95 and you will see ghost towns with boarded up houses and restaurants, and houses that have not been painted for years with cars rusting on the front lawns. Anyone who is used to big city life will go stir crazy up there. I just spent a weekend up there and there is something very lonely, stark and isolating about that area. It’s almost spooky. I walked into a local bar and it was like a record scratch…the locals are not fond of outsiders. The wilds of Maine are a nice place to go for a weekend of rafting, hiking or skiing, but not for living year round. Nevertheless, I wish him luck with his new hotel…..hopefully he is not an aspiring writer. ;)
Oh please. All the Maine-haters (or is there just one?) need to get over themselves. I know they think they're truly cultured living in tiny apartments in anonymous cities near cultural attractions that they never seem to visit or actually appreciate. Honestly, though, some people just don't like living in crowded urban centers. Others can't afford to, even if they would like to. That doesn't make them stupid, racist, or provincial hicks.
It never ceases to amaze me how the some of the seemingly most compassionate, liberal, and wise people I know in cities make wisecracks about people who live in rural, and even semi-rural and suburban, areas. Their lack of knowledge about how so many Americans live reveal them to be truly out-of-touch.
I'm sorry our Bates guy never took the time to actually enjoy Maine. What a waste.
50 here (second post here),
Listen, the transition from NYC to rural Maine will be rough. The transition from most places where there are things to do to Maine is rough. Sure, Maine has nice areas - Bar Harbor, Wiscasset, Popham, Cape Elizabeth, etc. But you can't afford to live in those towns if you work in those towns; no more so than in Nantucket, Newport, Southampton, Kiawah Island, or other such coastal destinations. The rest of the state sucks assmoose, as it were. Which is extra painful because of the antlers.
Highlights of my time enjoyed in Maine:
- Lewiston had such polluted air that I would usually barf when I went running (and I grew up just outside a major city that had a substantial manufacturing base).
- The first time the windchill dropped to 35 below zero for a solid fucking week and I got sinusitis.
- going to a college with a single dining hall that sat maybe 600 students. The college enrolled 1800 students.
- the time a Lewiston PD pulled me over on campus for allegedly speeding (I assure you, I was not), interrogated me with hand on gun holster, and called for five units to back him up. After about an hour, they let me go with no explanation or ticket.
- The time my 15 year old Toyota was broken into on campus via brick, my radio was stolen, my seats were slashed, and parts of the dash were bashed in. On the bright side, the thief left me the brick.
- The time a foot of snow fell in the last week of April.
- Going to the bathroom. Every dorm at Bates had removed paper towels and had auto-off sinks. I'm all for the environment, but since the school was too cheap to put in hand dryers or sensors for the sinks, it meant that a) towels = pants and b) unless you had three hands, you could not turn the hot and cold faucets while shaving or washing your face. Also, one of bathrooms in the Bates-owned houses I lived in didn't even have a door.
- The time I went running on a rural road, heard a enlongated honking behind me, turned around, and saw a pickup deliberately swerve at me. I had to dive into a six foot ditch on the side of the road to avoid being hit.
- Being surrounded at Bates by women who looked and dressed like festively plump lumberjacks. At that time, Bates had three treadmills. It showed.
- Being surrounded at Bates by guys who looked like anemic stoners who an average 6th grader could kick the shit out of. At the time, I was 6' and 160 pounds, and I could have been a linebacker on the football team (which, as I recall, won three games in the four years I was there).
- learning that Lewiston was the hard drug distribution center for most of New England, thanks to the large amount of abandoned mills and inability of local PD to cope. You did NOT want to be around the mill complexes at night.
- Watching the fucking Klan try to organize protests against the Somalian immigrants coming to Lewiston.
- The time a local guy wandered onto campus on night, went into the new academic building (which had no guards), dragged a freshman into the basement bathroom and raped her.
- The aforementioned incident when the lacrosse captain was killed in a street brawl with local teenagers.
- knowing that after 10PM, the only thing to do in the entire fucking state was to go to the LL Bean store in Freeport, which is always open.
- every news anchor on every local channel is convinced that Anchorman is a documentary (actually, that was a highlight).
- the time I was on I-95 in Augusta, and a giant tire fell off the open bed of a 1970's era pickup in front of me and slammed into the front of my car. He kept going and I spent a crapload of money fixing my front axle.
You're right, 72, I should just focus on all the pretty foliage, the thousands of miles of frigid coastline, and the few quaint towns that haven't Detroited themselves into oblivion yet.