Expert Q&A

Q&A with ‘Heads in Beds’ author Jacob Tomsky


Have you ever stayed at a luxury hotel and wondered what’s going on behind the scenes? In his new book, “Heads in Beds: A Reckless Memoir of Hotels, Hustles, and So-Called Hospitality,” hotelier Jacob Tomsky dishes the dirt on the hospitality industry

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Before you book your next hotel room, there are a few things you should know: The front desk may put a hold on your credit card for the entire cost of your stay, who you tip is more important than how much you tip — oh, and your minibar glass was probably polished with Pledge.

Don’t be alarmed; it’s nothing personal. It’s just the way things roll behind the scenes in luxury hospitality, surely one of the craziest industries in the world.

Just ask Jacob Tomsky, a military brat and 10-year hotelier who worked his way up from parking valet to Manhattan front desk overlord, with a particularly distasteful detour through housekeeping. Friendly tip: don’t make direct skin contact with a hotel remote. Ever.

Q&A with author Jacob Tomsky

Heads in Beads

Photo: Michael Lionstar

In “Heads in Beds: A Reckless Memoir of Hotels, Hustles, and So-Called Hospitality,” hotelier Jacob Tomsky offers up a candid account of how a luxury hotel is run and paints a vivid portrait of the people who run it.

Tomsky spills the chocolate-covered espresso beans and airs the industry’s 1,000-thread-count dirty laundry in his acerbic tell-all book, “Heads in Beds: A Reckless Memoir of Hotels, Hustles, and So-Called Hospitality.” It’s so authentic, there’s no 13th chapter.

Part Valentine, part poison-pen rant, “Heads in Beds” unveils the (mostly) human beings behind the front desk, in the bellman’s uniform and maid’s apron, and the hardworking stiffs with the power to turn your stay into the time of your life or a weekend at the Bates Motel.

Here’s one hotel tour you won’t find on any concierge list.

Q: What’s our biggest misconception when we enter a luxury hotel?

A: Thinking that it’s some sort of perfunctory operation where everything is decided. Actually, there is a lot going on. We’re all moving around and everyone you deal with affects your stay. Because it’s not a Monday-through-Friday job, the person who helps you today might not be there tomorrow or in five minutes. You’ve got hotel guests and hotel employees constantly fluctuating. It’s kind of like that saying, “You never step into the same river twice.” You never walk into the same hotel twice.

Q: Tipping, of course, is the currency of this wonderful, temporary land of luxury. What’s the secret of doing it right?

A: Tipping is such a strange phenomenon. Basically, it’s kindness manifested. If you walk into a four- or five-star hotel, there’s a lot of service going on between the valet, the doorman, the bellman and housekeeping, which is an incredibly hard job. So it’s very nice to tip them. If there’s room service, you tip them.

Q: You also suggest slipping a moderate-to-large bill to the front desk agent at check-in. Why?

A: Because that will directly improve your stay in the form of an upgrade, or at least get you a room away from the ice machines and elevators and something with a big closet and a big bathroom. And you now have an ally — not just any ally but a strong ally because front desk agents have quite a bit of power. When you think that there can be upward of 500 to 1,000 guests in the hotel and now you’ve got a friend, it differentiates you from the crowd. That’s always a good position to be in.

Q: Most of us seek out the concierge for local dining and entertainment suggestions. What’s wrong with that?

A: The good thing about the concierge is if you want to eat at a nicer restaurant or see a play or other high-end cultural event, the concierge has most likely had a first-hand experience at that. On the other hand, there’s a lot going on at the concierge desk that people don’t know. For instance, they receive kickbacks for filling up certain restaurants, selling certain shows and booking certain tours. So, in fact, it behooves them to steer your vacation in a direction that you might not have wanted it to go in. It might not be the best value, the best restaurant or the best tour, but it’s best for the concierge.

Q: Who should we consult instead?

A: People travel to a city to get to know that city and the bellmen and the doormen, almost 100 percent of the time, are born and raised in that city. When they give you a recommendation of what they like to do in this town, you can understand that it’s really from the heart and that’s what they think you would enjoy best. And they have absolutely no financial stake in it.

Q: Hell hath no fury like a hotel worker scorned. What are some of the ways that an overlooked or insufficient tip is likely to come back to haunt us?

A: There is sort of a culture of revenge. I think every service industry has something like that. What sets the hotel industry apart is we have quite a bit more access to your personal life. It ranges from the classic, such as throwing your luggage against the wall and damaging your personal property, to playing around with your toothbrush (don’t ask) to calling your room at 3 in the morning from a pay phone because you were rude earlier. We can set your alarm clock to go off at 3 a.m. every morning. The list goes on. It’s a very creative crew, unfortunately.

Q: Speaking of dirty little secrets, your peek inside housekeeping is pretty disturbing.

A: Housekeeping is an incredibly detail-oriented job. Cleaning 10-12 rooms a day and getting everything perfect 365 days a year is absolutely impossible. We’re human beings. It’s a tough job. I mention the mini-bar. OK, sometimes they clean the glasses with furniture polish to get them spot-free. They’re not provided with the right tools to achieve that, so they improvise.

Q: You maintain that a hotel TV remote is virtually impossible to clean.

A: When you start thinking about what happens with that TV remote, it does change your idea about it. Then again, you probably rode in a taxi cab to the hotel, and I guarantee you that taxicab is much dirtier than anything you might find in your hotel room. And I’m pretty sure it wasn’t disinfected. When I was in housekeeping, I saw quite a bit of blood-borne pathogens where you put on gloves before you deal with the situation because it’s dangerous. If you think about it too much, you’ll want to wear a haz-mat suit anytime you leave your house.


There is sort of a culture of revenge. I think every service industry has something like that.

Q: One of the ongoing challenges of a front desk agent is dealing with guests who are irate because their credit card is suddenly being declined all over town. Why does that happen?

A: When we’re authorizing your credit card for the whole stay, it’s important to know that a hold is going to be put on it, and that hold is usually going to be the room and tax complete, plus generally about $100 a night for incidentals, just to make sure that if you’re using the minibar or in-room dining, we have that coverage. A lot of people are concerned when they check in that all those funds are tied up, and it’s not easy to get that dropped, especially on the weekend.

Q: How can travelers avoid that problem?

A: I would recommend knowing what your credit card limit is and having a good idea of how much is going to be put on hold. Also, be aware that you almost always can change the credit card you pay with at the end of the stay unless you’ve prepaid on an Internet site. It’s almost impossible to get your money back if you’ve prepaid. The hotel may not even have it yet. But for everyone else, you can always switch cards.


It’s almost impossible to get your money back if you’ve prepaid.



Q: Is there a stigma associated with guests who booked online?

A: From the hotel’s perspective, guests who book online are already concerned about saving money, so they’re probably not going to be ordering breakfast every morning served in the room. They also chose the hotel based on a list sorted by price, which means they didn’t say, “Oh, I’m going to Chicago. I’m going to stay at my favorite hotel,” they said, “I’m going to Chicago. What’s the cheapest hotel?” That means those guests aren’t likely to return to that specific property, whereas someone who pays full rate and books a specific hotel through the hotel website or by calling might come back and choose it based on quality or personal choice. So the hotel is going to take those reservations a little bit more seriously, put a little bit more attention and preblock them into a room that is of a higher value just to make sure that they secure the highest-paying guests as return guests.

Q: Is there an equalizer strategy with the Donald Trump crowd?

A: You can absolutely book over the Internet, but the best thing you can do for yourself is to call ahead a couple days before you arrive — and I mean call the hotel and talk to a front desk agent — and find out what your reservation looks like. These bulk reservations often come through to the hotel with zero requests — not even a nonsmoking request. So it’s a good idea to call in and start working with a front desk agent at that point. The front desk agent doesn’t care where you booked it or if you’re paying $500 or $200. It doesn’t have anything to do with them. But the minute you call, you’re now just a normal guest who is coming to stay and wants to make sure they have a decent room, and that’s how I’m going to treat you. That separates you from the 200 reservations that came through that bulk server with no requests.

Q: I’m guessing we might want to continue that relationship in person, right?

A: Absolutely. If the desk agent you talk to seems really nice, get their name and ask them, “Are you going to be there when I check in? I really appreciate your help and I’d like to thank you in person.” That tells them that this person is going to arrive, they might see you and you might be held accountable directly to make sure that they do get all of these requests that we’ve just reviewed. So they’re going to tighten up a little bit, not only to protect themselves but also because of the possibility of a gratuity. That’s the best possible way to start off your stay.

Q: Although you like hotel work and seem uniquely suited to it, you don’t understate the emotional cost. What’s the hardest part of working a luxury front desk?

A: I’ve done some dirty business. It’s pretty amazing what you can get away with because it’s very hard to track down specific things such as who did what and when. Anything I did was all minimal, but I’ve known people who got caught being really out of line and were fired. Even when I was dealing with people’s bad sides — checking them in with a prostitute or mistress on Thursday night and then checking them in on Friday night with the wife and kids and absolutely throwing a blind eye about what’s happening when the family isn’t there — seeing and being implicit in that, it’s just part of being in the hotel business, that kind of discretion. You learn a lot about humanity and I guess it’s just human nature that it’s the negative things about humanity that sort of stick with you the most and keep you up at night, as opposed to all the positive things you might not have seen. But I’ve seen a lot. It’s a dark business.

See related:Hotels a hot spot for credit card fraud, Tipping your waiter or waitress? Ditch the credit card, pay with cash, Best bets for hotel rewards cards,

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