Jacqueline Pirolo knows all about the grind. The Italy-born, Long Island–raised beverage director of Wine Spectator Award of Excellence winner Macchialina in Miami started her career at a grueling, sleep-at-the office film production job in New York City. But when one of her older brothers asked her to help open the Saint Austere restaurant in Brooklyn, she not only found her calling, but connected with her past.
Another brother’s restaurant opening brought her to Miami, where she has since made a name for herself in the growing South Florida wine scene at Macchialina, where the all-Italian wine list showcases many of Italy's indigenous grapes. (Macchialina essentially translates as “little spot.”)
Having older brothers in the business was key to Pirolo’s career transitions, as they were personally invested in her success and willing to give her responsibility early as they trusted in her ability to manage and promote their projects.
Pirolo recently sat down with Wine Spectator's Shawn Zylberberg at her Miami Beach restaurant to talk about her unique wine list, dealing with staff shortages and what people get wrong about Miami.
Wine Spectator: What were you doing before you got into wine?
Jacqueline Pirolo: I studied marketing at SUNY Oswego, then went into visual-effects production for movies and commercials. I felt the pressures of having to use my degree … it meant going corporate. I felt like I was taught to get this 9-to-5 job, be in New York City, have this hustle. My commute from Long Island into the city was two hours. I couldn't afford anything on what I remember being a $26,000 salary and had to work in restaurants part-time on the weekends to make ends meet. I kept looking at the people above me and thought, 'These hours are brutal.' Being the lowest on the totem pole, I had to be there from 9 a.m. to 4 a.m. sometimes, and even stored a toothbrush in my desk drawer because sometimes I slept at the office. Eventually I said, 'I want no part of this for a 60-second Kmart commercial.' That's when my brother Fabrizio approached me to help open a restaurant in Brooklyn.
How did that unfold?
Fabrizio had worked in restaurants a lot longer than I did and founded The Saint Austere in Brooklyn in 2010. Fabrizio asked me for help opening the restaurant, and I never thought it'd be a forever thing but it turned into that. I found I loved working in the restaurant, and I looked forward to doing that more than my production job. Fabrizio said, “Come do this with me and if in a couple years you're like, 'It's not for me', go back to production.” Everybody warns you of the hours at restaurants, but coming from hours in production, this was a walk in the park. It was around for 10 years and closed at the start of the pandemic. What's odd is that neither of my parents were in the restaurant industry, yet I and my three older siblings are.
What was your 'aha' bottle?
Fabrizio also had experience in wine distribution, and he was my wine mentor. He always spoke about it in a way that was passionate and simple, but not pretentious. He just had me taste and figure out what I enjoy and what I don't. My earliest memory was from when I was in college. He and I opened a bottle of Cleto Chiarli Lambrusco, which is on Macchialina's by-the-glass menu today. We had it with prosciutto and cheese, and I was like, 'What is happening to me right now? This is insane!'
I remember going back to college at that point and going to every liquor store in Oswego trying to find Lambrusco and everyone was like, 'What?' The one place that did have it only had the gallon jug on the bottom shelf, which was too sweet. I still love Lambrusco.
Was wine part of your upbringing?
I was born in the city of Avellino in Italy, but moved to Long Island when I was two years old. But wine was always on the table growing up and going out to eat, and having wine was always a big part of the family dynamic. I never put it together as a young adult that that is what I wanted to do. To me, wine was just a fun hobby.
How did your journey to Macchialina start?
At one point, my brother and chef Mike came up and helped us make the menu for Saint Austere in NYC, and he decided he wanted to open his own restaurant in Miami, where he was living. Mike opened Macchialina in 2012 with his wife, Jen, who is also my business partner. I moved to Miami to help them open a separate restaurant in 2016, which only lasted a year, with the idea of it being temporary. The day I landed, my brother took me around and introduced me to everybody and said, “This is my sister and she just moved here.” It was him laying the groundwork to get me to fall in love with Miami.
What changes did you bring to the Macchialina wine list as the new beverage director?
When I took over the list at Macchialina, we were Italian focused but not solely Italian. The restaurant was very small and without a ton of storage. I felt like we were not giving Italy the proper limelight, but we also more importantly were not giving the other regions that we were representing the proper focus. So I got rid of other regions and made it an all-Italian wine list. People said I was crazy because they thought consumers were gonna want their Napa Cabs. But this way we can focus on Italy's indigenous varieties because, if we don't drink them, they're going to go away. They're [producers] going to rip them up and plant them to something else people are buying.
How do you teach your staff about wine?
We started this culture where in order to work here you have to at least be interested in wine. Over the years, the beverage program has become just as much of a backbone as the food, so it's important that our servers and managers can speak on the wine to a certain level.
Everybody that works here understands it's an ongoing training with wine. Our list is always changing, and a good amount of self-study is involved in order to work here. We also have something called Wine of the Week where every staff member chooses a wine off our list and they stand up during pre-shift and give us their spiel on their wine—be it type of grape, tasting notes, story—and everyone takes notes and asks questions. We'll often open the bottle and taste it as well. But it's more about getting comfortable speaking about these wines.
People come in and ask for Sassicaia and all that, but I go back to what I learned from my brother and take out the pretentiousness and convince people to try something new and different. What I tell my staff here all the time is if they [diners] don't like it, take it off the table. It's just a bottle of wine, and we don't have to convince anybody of anything. Open something else for them. Nine out of ten times they're going to end up liking what you pour them. We didn't make that wine, and we don't have to take offense.
How have you dealt with staff shortages during the pandemic?
It's been extremely difficult and probably the most challenging aspect that I've had to deal with at this restaurant. I've never seen anything like it. I think it's finally starting to pop a little bit. In the last five to six months, it doesn't feel as daunting. There was a time where we were having conversations like, 'Do we just have to hire bodies at this point? It doesn't matter their experience.' There were also nights where we were closing sections of the restaurant because we didn't have enough staff. We had to call people and cancel reservations. It was very stressful but that seems to have changed. I think we're back on the path of, 'In order to work here, you have to have a certain level of experience.'
Do you feel that there is a stigma associated with restaurant work?
There's this awful stigma that, if you have a degree, you can't work in a restaurant because you could've done that without a degree. Yes, you can, but your degree can also benefit whatever you choose to do in that restaurant as well. That's what a lot of people to this day don't realize.
What do wine lovers get wrong about Miami?
I don't think people give Miami enough credit. Oftentimes people are trying to simplify their menu or offerings too much because they're too afraid the Miami consumer won't get behind it. But people here love to travel. That's the first thing I noticed when I moved here. I think the people that travel then come back and ask, 'Why don't we have this cool coffee shop in Miami? There's so much potential. Thankfully there are a handful of people that push to be a diverse spot in the wine world.
Has the migration of New Yorkers to Miami during the pandemic changed your business?
I think it brought more stable business and less of the seasonality. I don't think the summertime slows down like it used to. We also leased more outdoor space during the pandemic and now have the whole building. We are starting construction and making a wine room with our expansion, so there is a lot of growth. Ten years ago, we would have never been able to fill a space this big. We also started a retail shelf with wine during the pandemic and it took off, selling wine to people that had never even been to the restaurant and thought it was a wine shop.
What is the Macchialina Wine Collective?
It's a monthly wine club that offers two-, four- and six-bottle options. It does not only focus on Italy though, but rather different themes every month. I'm having so much fun with it because it allows me to not just focus on Italy. Members also get a snack from the kitchen made by the chef and first dibs on reservations to our events throughout the summer.
What is one of your favorite Italian wine regions?
I would say Alto Adige. I visited in 2019 and it was jaw-dropping. There's cool stuff happening there with the alpine influences, and I love the white and red wines coming from that region. I remember I fell asleep on the bus in Tuscany and woke up among the Dolomites and thought, 'Where are we?!'
Are there any other regions you're interested in?
Most recently Austria, which was our most recent wine club theme. The wines coming out of there are truly special, and the prices are so affordable and approachable for the quality of wine you are getting.
What are your future plans?
We have the expansion, which in my mind is like opening a whole new restaurant. And we are opening another concept in the Little River neighborhood later this year and that will be a bottle shop, pizzeria and specialty market. The space will also include a 150-seat patio out back. My brother Mike and I are excited about this because traveling and having lived in NYC, there are specialty cheese, wine and meat shops, but you can't combine those places for legal reasons. But in Florida, there are no laws like that, so I'm like, 'How is it that nobody has done this specialty artisanal high-end shop where you can't get these products at Publix or Whole Foods?'
We want to offer a huge sake and Sherry selection as well. Those are two of my favorite things to drink, and it is still difficult to find more specialized products in Miami. This would be a place to hang out or take Macchialina home. It's been years in the making.