The Couple Who Got Married While Launching Two Start-ups

When we ask newlyweds to think back on what they wanted most for their big day — and we’ve interviewed hundreds of them over the years — the most common response is, “For it not to feel like a wedding!” But in a monsoon of flower crowns and macaroon towers, how do you see beyond the usual tropes and actually pull off a non-cookie-cutter affair? For the answer, we’ve decided to interrogate the cool couples whose weddings we would actually want to steal — right down to the tiger-shaped cake toppers.

Here, we talked to Jenni Lee and Tyler Sgro, two entrepreneurs who met as colleagues at the razor disruptor Harry’s and have since launched separate businesses of their own. Amid the stresses of start-up life, they decided to keep their September 2018 wedding simple, throwing together a morning at City Hall and evening cocktails at the Gramercy Park Hotel — Tyler in a hunter green suit, Jenni in a Dior-inspired suit-dress, both made by a friend in Toronto. They pulled off the fruit sponge cake at the last minute.

Tyler: No disrespect to all past or future jobs, but Harry’s, the men’s grooming start-up where we worked, will always be the best job I’ve ever had because it’s where I met Jenni. Jenni left Harry’s and started her own sock business, Comme Si, and I’m the general manager of Equal Parts, a kitchenware start-up that’s about to launch, and so we were working like crazy, traveling almost every week when we got engaged.

Jenni: We were floating ideas — should we get married in Arizona, where I’m from; in Toronto, where Tyler is from? Or Italy: My products are made in Italy so I travel there. But then that would have been a ton of planning.

Tyler: So we thought, hey, let’s do something super small at City Hall with immediate family and then we’ll do a big celebration in Italy in 2019 or 2020.

Jenni: Except I really didn’t want to plan a mini-wedding and a big wedding. So we picked the Gramercy Park Hotel [$37,000]. It’s obviously a beautiful location — all the rooms are in beautiful red velvet or deep blues, these really rich textures — but also they were honestly the most flexible. They said, “As long as you meet this minimum, you can do whatever you want.” It’s priced per head, but all food and drinks add up toward the minimum. So we initially didn’t plan on having a dinner, but realized that with that budget we could afford to do a sit-down dinner for our family, and then all of our guests were invited for hors d’oeuvres and an open-bar situation. Furniture, the sound system, and the staffing were included.

Tyler: It also just happens that the Gramercy Park Hotel was the first hotel I ever stayed in visiting New York as a kid. You can see the Empire State Building from the terrace. And upstairs, where Jenni and I ended up having our reception, it almost feels like a greenhouse — really open and airy with skylights and a lot of greenery.

Jenni: For my wedding dress, I never pictured myself in a gown. And once we decided on City Hall, I was like, cool, I’m wearing a suit. My husband was getting his suit tailored from a family friend, Marlon Durrant, up in Toronto, and at one fitting appointment I asked, could you make a woman’s suit? He asked for images of what I was looking for, so I tried Googling “form-fitted blazer dress” and came upon this Dior runway look from the ’90s. Marlon replicated it for me from scratch [$2,600]. The biggest topic of conversation was how to cut it in a way that it actually flounced; how to find material that’s soft enough to flow, but not so soft that it’s streaming. We went through many different swatches of material to achieve a structured, but not too structured, shape.

Tyler: The tailor has been in the back of my mind for years — he’s the father of a good friend of mine — but he was a little out of my price range for everyday suits. I said to myself, when I find that person, when I have that day, I really want him to make my suit. And I really wanted something different. I’d always loved the color hunter green; it makes a statement, plus it felt nice for the fall. You always take a bit of a gamble when you’re going through swatch books — how’s that going to look in the actual amount of fabric to clothe a six-foot man? But I saw a Paul Smith suit that was similar and it turned out great. I wore the suit again to an event not long ago, and people were like, oh my gosh, that’s a great color. It’s a nice little memory. [$2,600]

Jenni: I loved his suit. It was such a great experience going to fittings together. We picked swatches together, critiqued together — he would try his on and I’d be like, “Oh, take it in on the sides.” For shoes, I asked a few stylist friends if they could send me any cool or interesting shoes that they’ve seen across their showroom pulls, but then I was at Saks and came across these pearl, curly Chanel strappy sandals and just bought them [$900].

Tyler: We stayed at the hotel the night before to make it a whole weekend, not just a one day thing — to be honest, some of my fondest memories of the day are people coming in and out, helping us get ready together. My sister-in-law brought their new puppy, Barkley, and he was lying on the bed, watching us get dressed. Then we took the subway from 23rd Street to City Hall, which was a great experience — no one was on it even though it was just after rush hour, and it was a clean car with no New York City smells. Then we waited in line to get married.

Jenni: We had no idea how long it was going to take, because it really just depends upon the day, so we told friends, “If any of you can miss work, or step away for a few hours, we’ll be at City Hall.” They don’t limit the amount of people you can bring in, it’s just as many as will fit. We had about 30, 35. The ceremony was short but sweet and then we walked over to Golden Unicorn [$800] for a dim sum lunch.

Tyler: A group procession to our favorite dim sum. I’ll always remember rolling up as a squad, and the place doesn’t even take reservations.Then it was the classic experience, the carts going by and food flying left, right, and center. We had pork buns, steamed buns, soup dumplings. I love their shrimp dumplings.

Jenni: We went back to the hotel and intended on having a nap. It was then that we realized something: We didn’t have a cake!

Tyler: Jenni and I put a lot of detail and expenses into the things we really value, like what we wore. There were things we didn’t spend a lot of time on, like the cake. To each his own! I can’t remember the last cake I had at a wedding. But we love Tous Les Jours Bakery for tons of reasons — we had desserts and coffee there, a Korean tradition, one of the first times our families met.

Jenni: I sent my brother out and he went to Koreatown to the Tous Les Jours Bakery. I knew I wanted their fruit sponge cake because I’d had it for a previous birthday cake of mine, so I told him to get a few of them. He actually grabbed two fruit sponge and one red velvet because they didn’t have enough in their display case [$72]. Later that night, an engaged guest asked me who our cake vendor was! Also, when we had done our walk-through of the hotel and terrace weeks before, I thought flowers were included, but they were not, so then I sent him to a bodega to grab a few stems. For City Hall, I had a bouquet of gem-toned flowers made by Fox Fodder farm [$250], but for this, we FaceTimed with him at the bodega. They didn’t have a great selection so we did a combination of daisies, baby’s breath, and red, yellow, and green asters [$42].

Tyler: There was a private dinner for two hours with close family and close friends, about 30 or 40 of us, on the terrace overlooking the city. We had branzino and a filet mignon, plus a veggie option, with an heirloom tomato salad as a starter. We did a pavlova for dessert, one of Jenni’s favorites.

Jenni: And then the rest of our guests were invited from 8 p.m. to 2 a.m. For the evening, I changed into a Prada cashmere polo top [$800], with a custom silk skirt from Etsy [$150]. I was out shopping for shoes and when I saw that top, and in that moment I decided, You know what, I’m going to change into a second outfit at the wedding! Because it’s my wedding and why not. Like the suit-dress, I had a vision: It was Claudia Schiffer in a 1994 Vogue spread called “Roman Holiday” photographed by Arthur Elgort — she’s got this beautiful bubble-gum cashmere sweater with this big silk skirt and it’s fitted to her waist. I came across this woman in England with an Etsy shop and she was making skirts in that kind of material. I placed the order and it arrived the day before the wedding.

Tyler: The design of the room happened to be perfect for saying hi and really connecting with everyone as they came in. We were at the entrance and then it flowed onto the terrace and the bar. Drinks started flowing immediately, and we also wanted to make sure our second wave of guests were well-fed. We had a bunch of passed hors d’oeuvres like arancini and shrimp, and then prepared food sitting out buffet style.

Jenni: My sister works at Spotify, so I tasked her with playlists. She made a playlist for every time slot of the reception, so for dinner and when people were arriving, it was Louis Armstrong, Ella Fitzgerald — nice, easy tunes. For post-dinner drinking, a little pop, top 100 hits, and personally I’m a big fan of Drake, so it was a lot of Drake. Past midnight it was all club bangers. They had said they’d charge if we added extra hours, and I think we added one or two, which cost $25 per head per hour. It was so late that the coordinator wasn’t there — I want to say that they were counting guests, but I actually don’t even think they were counting guests. We were up there until like 2:30, 3:00 a.m.

Tyler: The dancing picked up as it got later in the night — I have fond memories of passing the mic around to different friends and everyone was karaoke styling.

Jenni: They had said we could order pizza to the restaurant at the end, but we ended up being too drunk to do it.