Kai is a hug-instead-of-a-handshake kinda girl. I immediately want to be her friend, not only for the sake of her wardrobe. Kai’s warm, welcoming nature is felt throughout Sincerely, Tommy—her thoughtfully crafted concept store in Bed-Stuy, Brooklyn. She may be easy-going but her vision is deliberate: “I want the energy to be a certain way, and it’s harder to direct that if I’m not here. Even those nights when I’m exhausted, I don’t want to leave. This is my baby.” This energy that Kai creates, coupled with her exceptionally good taste, means you’ll never want to leave Sincerely, Tommy either.

“Before Sincerely, Tommy I’d had a lot of retail experience which was all quite similar in nature… super intense with very strict systems. I had learned a lot, and after wrapping up a managerial role at Aritzia, I was ready to do my own thing. Opening a store had always been a dream of mine. I approached my mom and grandmother who do real estate in this area, and told them I wanted to create a space in either a brownstone or a pre-war building. We started looking, and I think this was the 6th or the 7th space that we saw. I loved it. It’s on the corner, it’s a few blocks from where I live, and I see a lot of potential on Tompkins Avenue which I think others are picking up on too.

I didn’t know how it was going to happen. I hadn’t been saving money, I didn’t have a business plan, I just decided I wanted to have a store.

I knew how I wanted it to look and what kind of products I wanted to sell. For me, the vision is the most exciting part, and it also really helped in seeking out the right people and tools to turn that vision into a reality. The business planning service SCORE set me up with an amazing counsellor who helped me with my business plan, and gave me some really good advice. That was 3 months in, then 5 months later the store was here. It was very, very quick—to the point where one day I thought wow, this is really happening. I didn’t even know how. Throughout the build-out, I was emailing designers. I tried to create a deck and it just looked really shitty, so I had to describe the space as best as I could considering it didn’t quite exist yet. But most of the people I reached out to got back to me, and I ended up carrying all of the brands that I wanted to. That original vision for the space is always evolving. Right now it’s about traveling, meeting designers, being influenced by that, wanting to incorporate different textures or new elements into the store.

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When I realized this was really happening, I decided to treat the first year as a test run in terms of trial and error, figure out what works and what doesn’t. Now that I have a customer base, it’s a constant reminder that there’s a market out there for what I’m doing. That there are people who appreciate emerging brands that may not be Céline, but they’re still really great products. There are pressures that I’m learning to deal with, like what I want for the store vs sales figures… becoming familiar with any new business is challenging in general.

You’re taking on a whole new experience and really have to own it.

Being in this area can be a bit tough, in the way that there’s nothing like this around. The people who live here don’t always understand what it is. There’s one side of this neighborhood which speaks to that newer demographic: young creatives, artists, or people moving from the city. Then there’s an older generation who have been here for years, who don’t know what a concept store is. I’m still trying to figure out how we can speak to both. How can we get people involved and make them feel welcome? Even if they don’t want to come in, at least for them to know that we’re trying to do something positive. That it’s important to try and do things here, rather than just leave and give up. But from day one I thought, if people come in who do get it, then I’m doing something right. And I’ll keep moving forward, keep building the business, and have that faith.

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Another learning curve has been figuring out how to balance my business self with my creative self. I’d do the creative stuff all day every day if I could. I’ve had to become much more organized, and while I’ve never been super sporadic or all over the place, now I definitely have to stay on top of my calendar and tick off my to do list. I avoid being too rigid though, because so many things pop up in the middle of the day that I don’t expect. If I put too much pressure on myself to stick to schedule I’ll go crazy, so I try and take it for what it is and do my best. I also have a great mini team behind me to help juggle everything. In the beginning you try and do everything yourself, but I’ve gotten really good at making sure I have the right people around to help. I think being surrounded by supportive people is crucial.

That’s what community means to me: constant support. Whether it’s family, friends or locals, it’s so important to be there for each other. Also to show a younger generation the value of re-investing in their direct neighborhood, and creating a backbone for yourself. This has been especially true for Sincerely, Tommy, which wouldn’t be here if it wasn’t for my mother and grandmother.

I come from a lineage of warrior women.

My grandmother moved here in the 60s and bought her first home in Far Rockaway. She then bought her first brownstone (the one I live in now) in the 80s, when Bed-Stuy was really dangerous. Everyone thought she was crazy for doing it, but she continued, and she ended up making her living through buying property. She was doing it before anyone really was, and she’s still doing it. My mom is pretty much the same. She opened up her first vegan restaurant about 10 years ago in Carroll Gardens before the whole vegan fad. So they very much have the entrepreneurial spirit and have always created their own way.

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Growing up, I didn’t see any other option than to work for myself and do my own thing. That independence has been instilled in me in a lot of ways. I’m a big believer in traveling on your own. You’re forced to rely on yourself and figure things out. That might not be an option for everyone, but it’s something that has always helped me get outside of my comfort zone, and has opened a lot of doors. It also teaches you to be more in tune with your intuition, which has always been a guide for me.

If my spirit feels right, then that’s the way I’m supposed to go. If it doesn’t work out, at least I’ve learned from that.

Being alone in general is something I really value—aloneness, not being lonely. I like to have my own space to think. I feel most inspired then, and sometimes I just enjoy the silence. Maybe it’s from living in a chaotic atmosphere, but especially as I get older and take on more and more, I really enjoy those special moments when it’s just me.”


  • Do what you can with what you have.
  • Community creates a backbone.
  • Figure it out along the way.
  • If it doesn’t work out, at least you learn.



i. @sincerelytommy_


Photography by Amy Woodside

As told to Amy Woodside, April 2015