On being an entrepreneur

Hello, kind reader.

I’m writing because we are heading to NYC and, if you live in the area, I would love to extend an invitation to a trunk show on Thursday and Friday, as well as a Cocktail Reception we are hosting tonight with our hosts, 180 the Store:

While I am still very much in the restaurant business, I have been, for the last several years, inching toward, tiptoeing, an outstretched arm reaching into a new career. Almost four years ago, my wife and I launched a shirting brand - originally for women, and as of today, for men, as well. The clothes are designed by Erin, a gifted designer with 25+ years in the industry, with me in the corner, foisting my opinion upon her, plus a talented pattern maker playing a large role in bringing Erin’s designs to life.

Originally, I was in the wings: writing copy for her site, naming the shirts (I love this part), helping style the photoshoots, ideating with her about the details, and spreading the word. As time went on, we found the partnership worked. I loved building something new, she liked having a strong partner, and we both knew we were stronger together.

The business is based in Charleston, but we manufacture the shirts in the finest workrooms in New York City’s storied Garment District - a city within a city, under threat of disappearing. It is a little village of industry, less than one square mile, where workrooms and factories are squeezed up next to pattern makers, button and trim shops, cutters, washers, pleaters, button-hole makers, fabric shops, milliners - it’s like a Richard Scarry book come to life. This is where Erin got her start, and where we intend to manufacture our shirts until we hang it all up and ride off into the sunset - many years from now, we hope.

At 41, I am extremely lucky to have benefited, many times over, from partners smarter than me, whose talents beautifully augmented my own, and whose skills made up for my shortcomings. I am aware of what I do well and what I cannot do. There are plenty of entries in both columns, but I’ve found the key to success is finding people who check plenty of boxes in the “what I cannot do” column, and then keeping them close.

I first became an entrepreneur 15 years ago, when I founded Jack Rudy Cocktail Co. At the time, I was managing a restaurant 10-12 hours a day, producing cocktail mixers after work, late at night in my home kitchen, and managing the business in the scant hours before work each morning. At the time, I had a young son, and all I remember thinking during those years was I’m going to be a success for him. I burned up every hour of the day building that business in the early years. I sent so many emails, knocked on so many doors, hosted so many tastings, cocktail hours, trade shows - anything to tell mostly uninterested parties about what I was up to.

It clicked. Right place, right time. In the third year, I was joined by my cousin and business partner. In the years since, he’s been the man behind-the-scenes, writing the checks, balancing the books, minding the myriad of details required to run a growing concern. I get most of the credit, he does most of the work - still packing boxes when our warehouse manager leaves town on vacation, as he did this week.

The success of Jack Rudy allowed me to leave the restaurant business - a career I thought I was done with. I had worked in restaurants from 16; I was 28 when I left, ready to step into new riches and a life of private jets, giving all of my energies to this brand I’d built, along with my partner, into something real.

That dream didn’t last long. What started as an agreement to “help” a friend with a new project turned into an investment in my first restaurant - sucked back into the vortex. Inexplicably, it was a riotous hit from day one. 11 years into my journey as a restaurateur, I’ve had some major wins, some gutting losses, and expansion into New Orleans. Our restaurant there, The Bell, turns one this month. It’s been thrilling, stressful, full of heartaches and high-fives. As with every business before or since, I’ve benefited from a dugout full of people with a boatload of skills I could only dream of.

I’ve learned that being an entrepreneur requires ungodly reserves of grit, repeated ego death, and lots of schlepping. You cannot be too cool to simply get it done. You must be prepared to hear one thousand million nos and stomach it with a smile. Even tonight, after I schedule this newsletter, I will head upstairs to pack up shirts for our trunk show, hauling them off (I will be sweaty) to the airport in the morning, carting them through Manhattan to our hosts, and then unpack, steam, showcase, fold ‘em up, ship ‘em out, and do it all over again and again. It might look good on Instagram, but real entrepreneurship is two parts sex, ten parts schlep. Being an entrepreneur is like pulling on warm cashmere socks to find a family of scorpions inside.

Just yesterday, after tasting a few dishes we’ve been having trouble with at one of our restaurants, I put on a different hat, loaded up the car, and schlepped boxes of Jack Rudy products across the bridge to a new partner, The Fresh Market, who is stocking some of our products in stores nationwide:

Then home to cook dinner, put our son to bed, and, along with my wife, write a launch email for our newest style, write this missive, AND review the edits for our brand new website, which we’ve been working on for the past several weeks - trying to find the flaws and the glitches before you do.

This is what it takes. We have no investors - never needed ‘em, don’t want ‘em. There is far too much money, few too many good ideas. We do things on our own terms, and we reap the benefits. Beyond our customers, we have no one to answer to, and we like it that way. But it means, from time to time, your foyer will be full of boxes, your guest room will be full of shirts, and you may have to break a sweat.

If any of you are in NYC this week, please come by 180 the Store and say hello. I’ll try to towel off before the trunk show starts.