A portion of proceeds benefit a cause close to his heart: The Heroes Project, supporting wounded veterans. Caliendo spent six years in the Marine Corps as a CH-53 plane captain and martial arts instructor, with three active duty deployments.
After the military, he went to Bridgewater State University to study business but preferred the restaurant industry to corporate life at a retail banking job. He worked in management at the Atlantic Beer Garden, Whiskey Priest, Pasta Beach, Nebo, and Stephi’s in Southie before joining Grill 23.
Now, he reflects on his encounters with a pre-Oscars slap Will Smith, a martini mishap, his years in the Marine Corps, and his first job as a teenage dishwasher growing up in Easton.
Why do you like your job?
The people I work with are experienced. They’re mature. The hours are great. The schedule, for me, is very flexible. I work five nights a week there, but if I do need to take some time off for the business, enough people can fill the void.
The restaurant takes great care of us in every aspect: quality of life, benefits, stuff like that. And the money is good. They match our 401(k), health, dental.
Tell me about your military experience.
I joined the Marine Corps in 1999. I was joining to get money, and a little bit more discipline, for college — I wasn’t ready, right after high school. I went in to be a helicopter mechanic.
After September 11 happened, they were in need of more crew chiefs. I decided to laterally move over to a job as a crew chief on CH-53 helicopters and a plane captain, and I also became a marksmanship instructor for my unit and a martial arts instructor for my unit. I was in the Marine Corps for [six] years with a handful of deployments. We did a lot of equipment transport and troop transport. When I was discharged, I came home and went to Bridgewater State.
How does your military experience play into your life now?
Empathy and understanding — mainly understanding a lot of different cultures and where people come from. It really helps me communicate and understand the different people who come into the restaurant.
Was it jarring to be so young and far from home?
Of course. You miss home a lot. You miss your friends. But it’s also a very exciting experience. A lot of people would think that, if you’re going halfway across the world to a dangerous area, that it might be scary. And it is scary. But it’s also exciting. You’re doing something for your country, and there are a mix of emotions.
And now you hold veterans’ fundraisers through Grill 23, right?
I’ve done a lot of work with a foundation called The Heroes Project out in California.
They take veterans who have some pretty catastrophic wounds, train them in world-class facilities for a year, and then they bring them up the tallest seven summits of the world: Mount Kilimanjaro, Mount Everest, Alborz.
They’re building a veteran retreat center on Ice House Canyon, which is on Mount Baldy, and they’re raising funds for that. The first year, we raised $25,000, and this year, we raised $58,000.
We took over the entire second floor of [Grill 23 sibling] The Banks. I did a silent auction raffle with an open bar and food.
Tell me about your other side hustle.
It’s called Corpsman’s, and I started it as a way to give back to The Heroes Project. I went to college for business management, and I wanted to see what it was like to start a business. We give 5 percent of our profits to The Heroes Project. It’s been a great experience, and the company is successful.
We have six different types of hair pomade. We do beard oil, beard balm, mustache wax, a sea salt texture spray, texture powder, and I’m currently looking into making a shampoo and conditioner as well.
What’s your sales pitch?
The market is extremely crowded, more so than when I started, which makes things a little bit difficult. But what makes mine a little bit different is, first, it’s all-natural. Two, we give back to wounded veterans. Three, it was very local at first, and the barber shops and salons in our area wanted to support a local company.
They wanted to support a small business, they wanted to support something good for their clients and give back to wounded veterans. It gives a lot of these wholesalers, the barber shops and the salons, something to talk to their clients about while they’re in the chair — something their clients can feel good about buying and something that they can feel good about selling.
What was your first food job?
I was a dishwasher at Tally Ho restaurant in Easton.
The worst part about that job is they served chicken parmesan on these metal dishes that they would actually put in the oven. I probably have arthritis in my shoulder and elbow from having to try to scrub the cheese off the metal tin. It was the worst part of my job. I remember it to this day. It was awful, absolutely awful.
OK, back to Grill 23: Give us a public service announcement. What should customers never do?
This is an easy one. Let’s say it’s an eight-person table, and I come to the table and say, ‘Can I get anybody anything at all?’
I look around the table, and five people have empty drinks, and then three people go, ‘Yeah, I’ll take a refill.’ And I go to the other two people and say, ‘Can I get you two anything? You look like you need a refill,’ and they say, ‘No.’
I get the other three people their drinks, and the other two go, ‘Hey, you know what? Yeah, I’ll take one.’ It’s called one-timing. Now you’re going to send me back to the bar and back again. Then, when I come back with those two drinks, another person at the table needs something.
Just stop for a moment, take a breath, and look around: What does everybody need? It really bogs you down when you’re making multiple trips to the same table.
What’s the weirdest request you’ve ever gotten from a guest?
I had a young woman who came in because we’re so known for icy martinis, but she had no experience with martinis.
I was trying to tell her, ‘Listen. It doesn’t have to be a dirty vodka or gin martini. It’s anything in a martini glass that’s icy. It can be a cosmo. It can be a sidecar. It can be whatever you want. As long as it’s in a martini glass, it’s going to look icy, and you can take the picture you came in here to take.’
She said, ‘You know what? I think what I want is a gin martini. But I want it to be sweet. Maybe add some St-Germain?’
I said, ‘You’re building something that I don’t think you’re going to like.’ And she’s like: ‘No, no, it’ll be good.’ So we built her a gin martini that had lime juice and St-Germain, and she wanted me to add a bit of pineapple juice.
I was really trying to talk her off that ledge. I was trying to talk her into maybe a porn star martini, or a pomegranate martini, or something that we all know works. But she really just wanted this. I brought it to her. The whole time she was eating dinner, I could tell she was embarrassed, but she stomached it.
Did you charge her for a typical martini?
It was just a gin martini with a St-Germain add-on. I didn’t make her feel bad. I said, ‘You still enjoying your martini?’ I asked her a couple times, and after that, I just left it alone. That was a tough one for me to watch.
Where does the Boston food scene succeed, and where do you think we have room to grow?
I think we’re getting to be a little bit more diverse in the types of restaurants that we offer now. For a little bit there, we were opening up steakhouse after steakhouse after steakhouse after steakhouse. For a while there, I just thought we’re just going to be a city of just nothing but steakhouses.
Especially seeing as I work in steakhouses, I don’t want to make it sound like steakhouses are awful; they’re everywhere. But, you know, Grill 23 has been there for 42 years, right? It’s a flagship location of a steakhouse in Boston. Then you have Abe and Louie’s and The Capital Grille, which are all great places.
Everybody likes a great steak, right? But we do want to experience other cultures. We want to experience other types of food. I don’t think Anthony Bourdain would have wanted a city of nothing but steakhouses. R.I.P., Anthony. I think we’re becoming a lot more diverse.
Where do you like to eat when you’re not working?
This is going to be so contradictory. I like steak, so I pop into steakhouses. A couple of my favorites are Mooo… in the Seaport; I think the Columbus Hospitality Group does a great job. And I think Maple & Ash is doing a great job.
I’m a new fan of Zuma. Their atmosphere is amazing. I think their music is awesome. They did a great job with the architecture of their restaurant. The atmosphere and the attitude is great. And I like Contessa.
Anywhere close to home?
Novara and Antonio’s Bacaro.
Who’s been your most memorable customer?
I do have a memorable customer, but it wasn’t at Grill 23. I served Will Smith at Nebo.
I grew up with Will Smith, with “The Fresh Prince of Bel Air” and having him rap and everything else. I was very excited to have him there, but I think he was a little bit more wrapped up in his current company and not so much who was serving him food. He was very explicit: no pork.
I also served Larry David at Nebo.
Was he awkward?
He’s just like he is on his show. It’s like he’s not even acting.
Was he a good tipper?
He was.
This interview has been edited and condensed.
Kara Baskin can be reached at kara.baskin@globe.com. Follow her @kcbaskin.
Dining and Cooking