Gosh, I Needed a Mentor

Welcome to our new series, So You Want To Open a Restaurant. First up, why my restaurant experience was a bit of a wipeout.

Editor’s note: Today, we’re kicking off a brand new Cherry Bombe Substack series called So You Want to Open a Restaurant. Each month, Cherry Bombe founder and former restaurateur Kerry Diamond will talk to different folks in hospitality to get their take on how to run a successful business. Whether you’re thinking about opening a restaurant, cafe, coffee shop, or food-focused pop-up, or you already run a business, this is for you. Thank you to Square for supporting our series.

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A brief coffee break outside my coffee shop, Smith Canteen

Let’s be honest. I had no business getting into the restaurant business. Yes, I was an enthusiastic restaurant goer, but that does not a great restaurateur make. I didn’t even know how to spell restaurateur. (No “n.” Who knew?) I never had a job in a restaurant or cafe or coffee shop, but I did work, briefly, on a food truck in the ‘80s as a teenager before food trucks were cool.

I was 15 and had snagged a truly boring summer job on ████ (name redacted to protect myself). I was punctual, but I was a terrible employee. I ate my body weight in hot dogs, drank bottle after bottle of Yoo-hoo, and gave away food to my friends—and the cute boys from the local high school football teams that practiced in the park where the truck was parked every day. I doubt ████ made a profit that summer.

Fast forward a few decades, I was working as an executive at the French beauty brand Lancôme and happened to start dating a chef. It wasn’t quite The Bear. Like Carmy, he had worked in fine dining, but he had become a private chef (pre-pandemic, before private cheffing became hot, thanks to folks like Wishbone Kitchen). But he really really wanted his own place. He asked if I would be interested in opening a restaurant with him and I, for some reason (love, the plot, sense of adventure), said yes. I didn’t ask about his timeline because I assumed this was something we would do eventually, when we knew each other better, maybe in a decade, but he meant ASAP. In what seemed like a nanosecond, I was the co-owner of a small, buzzy restaurant in Brooklyn. Then a year later, I was the co-owner of a coffee shop, and a year after that, another restaurant, and then another restaurant.

I did not have the presence of mind, or the common sense, to go get some restaurant experience during the planning and construction phase of the first place. (Granted, I had a major full-time job.) I knew a handful of restaurant people from frequenting their businesses, but not well enough that I could ask them for advice or work. I could have done some stages (the French term for spending a short amount of time in a restaurant kitchen as a test, or try-out, or to pick up new skills), had I known what a stage was. I knew several food media people and some of them were extremely gracious with their guidance. One of the city’s top two food critics, an old acquaintance, did tell me to change the name of the restaurant, and the type of food we would be serving about a month before we opened. That was a dark day. I don’t think I ever told the chef what he said.

I scoured the web for online resources about opening restaurants, but couldn’t find any. This was pre-TikTok, pre-MasterClass, pre the era of experts sharing their wisdom all over the internet and the apps. My partner did give me a copy of Setting the Table, the book by famed restaurateur Danny Meyer about his restaurant career and lessons learned along the way. I devoured it and took lots of notes.

Setting the Table by Danny Meyer

People in the neighborhood loved telling me the location we had chosen was a cursed space. The build-out, all the construction, and working with the architects and contractor was exhausting. I wrote check after check after check. I was introduced to the concept of a punch list, in which you walk around with the contractor at the very end and make sure everything is finished and done to your satisfaction. Did they call it a punch list because you wanted to punch your contractor in the face by the time everything was done? Or rather not done? I couldn’t help but wonder.

My partner put together a sweet and scrappy front- and back-of-house team and we opened our restaurant to a nice amount of fanfare. Lots of lovely magazine articles and online coverage, and so many interesting people came by for a meal, from bold-faced names (hi, Sofia Coppola, Candice Bergen, and Ina & Jeffrey) to neighbors, friends, and family. Everybody loved the fried chicken. Pete Wells, the famous New York Times restaurant critic who was friends with all of our friends, made an appearance and we had to pretend we didn’t know him. A New Yorker writer ate at the bar, then kind of trashed us in the magazine’s Table for Two column. Friend after friend congratulated us for being in The New Yorker. Crushed on the inside, I just nodded and smiled. It was The New Yorker, after all, and as a media girl at heart, there are few things I revere more.

I still had my day job at Lancôme, but I had to handle dozens of miscellaneous tasks for the restaurant, from playlists to P.R., events, social media, even random ingredient procurement. (“Can you go find quail eggs?”) Every Saturday in the beginning, armed with Q-tips and soapy water, I would deep clean the banquette that ran the length of the dining room and was a giant crumb catcher from hell. I will never forgive our architects for that one.

When the restaurant was open, I felt like I had to be there and help out somehow. I would swing by the tiny kitchen to take pictures for social media, but was usually shooed away. The basement office was so dreary I couldn’t bring myself to work from there, so I wound up hanging at the bar a lot, with friends or solo. In trying to make myself useful, I was exhausting myself.

As time passed and the business started to struggle, I had to confess that none of this came naturally to me. I didn’t understand restaurant operations, and I had no idea where to turn for help. It was hard to admit to anyone, let alone myself, that this was a mess of my own making. I also learned about the loneliness of being an entrepreneur. You can be surrounded by people, constantly, but there’s still this pervasive sense of being alone.

Right before this photo was taken at my coffee shop, the basement of the building flooded and the building owner thought our grease trap had caused the flood. I had spent the morning in tears and forgot a magazine was coming to take my picture.

Now, looking back with a decade’s worth of distance and perspective, I remember lots of magical evenings that illustrate why people open restaurants. Happy guests celebrating birthdays and anniversaries, exclaiming over the food and wine, singing along to my lovingly-labored-over playlists when a favorite tune popped up. Regulars who came by time and time again. I saw firsthand how every night at a restaurant, no matter how big or small, is like putting on a Broadway show. Sometimes you’re the original cast of Hamilton. (And yes, sometimes you’re a community theater production of Cats.) I understood how the restaurant business gets in your blood and changes you for life. You do feel like you’re on that pirate ship the late, great Anthony Bourdain talked about.

Today, I have zero restaurants and no chef boyfriend, but thanks to Cherry Bombe and 600+ interviews on Radio Cherry Bombe, I have lots of wisdom about the industry and the connections I wish I had back then. I could have spared myself so much financial and emotional heartache.

I’ve had the great fortune to observe and interview folks like Rita Sodi and Jody Williams, the brilliant proprietors behind the iconic West Village spots Via Carota, I Sodi, Buvette, Commerce Inn, and Bar Pisellino; Missy Robbins and Sean Feeney, the talents behind Lilia, Misi, and MISIPASTA in Williamsburg; and the incomparable Nancy Silverton, with a restaurant empire that stretches from L.A. to Singapore. Also Dominique Crenn, Suzanne Goin and Caroline Styne, Mashama Bailey and Johno Morisano, Gabriela Cámara, Sohui Kim, Martha Hoover, and Linda Derschang. So many people! So many people I’m leaving out! Even Danny Meyer, my sole source of information all those years ago. Folks who understand what it takes to make restaurants work.

The goal for this column is to share all their wisdom. Anything specific you want to know about? Anyone in particular you’d like to hear from? Comment below or feel free to DM me on Instagram at @kerrybombe.

Restaurants are some of the most important third spaces we have, and more essential than ever given what’s going on in the world today. We need these gathering places; we need these establishments where people just starting out can find a job, a paycheck, and a work family. And we need all the people, front and back of house, who make hospitality so hospitable.

Before we go, a few things. I’m very excited to start reading Service Ready: A Story of Love, Restaurants, and the Power of Hospitality by Molly Irani of the Chai Pani Restaurant Group, which she runs in Asheville, Atlanta, and D.C. with her husband, Meherwan, who also happens to be the founder of Spicewalla. The book is out March 24th. Stay tuned for Molly on a future episode of Radio Cherry Bombe.

Service Ready: A Story of Love, Restaurants, and the Power of Hospitality by Molly Irani

If you’re thinking about opening your own place or business one day, here is some basic advice that just might help you avoid a tough situation. These nuggets apply to lots of different industries, not just restaurants.

You don’t have to go from 0 to 60

Does your dream need to come true immediately? It does not. Maybe break it down into digestible pieces and add some time to the timeline.

Do your homework

You maybe shouldn’t own a [blank] before you work in a [blank]. Get your hands dirty.

For god’s sake, don’t finance your business with your credit cards

Or your 401k. I did this. You shouldn’t.

Three is a magic number

Two is not. If it’s just you and a partner, you need a third neutral party whom you both trust to serve as truth teller and tie breaker. Find that person.

Put it in writing

Love is grand, but a contract or written agreement is grander.

Hire the best experts you can afford

If you don’t have a good feeling about your lawyer, or your accountant seems messy and disorganized, find new ones. You don’t want to discover they’re bad at their jobs when it’s too late.

Trust your gut!

This is the most important thing I will ever tell you.

Sometimes things work out in the end

Remember, this crazy, complicated restaurant experience might have failed, but it did lead to the creation of Cherry Bombe, for which I’m incredibly grateful.

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Thank you to Square for supporting our series.

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