Kai Avent-deLeon on the Sheer Exhaustion of Being a Black Small Business Owner in America

The founder of retail concept Sincerely Tommy opens up about the lack of government support for small business owners during Covid-19, and the heavy toll of protecting your mental health as a Black woman and mother in the current state of America.

By Lauren Fisher

Courtesy of Kai Avent-deLeon

After months of nothing but Covid-19 coverage, nationwide protests over the death of George Floyd have shifted the mainstream media conversation from stay-at-home orders to the immense racial injustices plaguing Black America. Both of these crises have disproportionally devastated Black American communities, with Black women and men left shouldering the economic and emotional fallout on their own. As a small Black business owner in Brooklyn’s Bed-Stuy, Kai Avent-deLeon is feeling the pressure and exhaustion of all of it.

In 2014, the then 26-year-old opened Sincerely Tommy, a retail concept store and cafe in her home community. Over the last six years, without any outside investment and while becoming a single mother to her now one-year-old son Che, she’s managed to expand her business into a thriving e-commerce shop with a soon-to-launch furniture line, and next, a boutique hostel and restaurant—all while forgoing maternity leave and facing the challenges of being a woman of color entrepreneur.

Here, Avent-deLeon opens up about how she self-funded her business, how motherhood transformed her outlook on work, and how she’s dealing with the setbacks of both a global pandemic and the weight of systemic racism.

Let’s start from the very beginning of Sincerely Tommy. How did you first open the store and cafe?

I bootstrapped all the way. I had been working in retail for upwards of 10 years and my last job was my breaking point working for someone else so I decided to create a business plan. I brought it to my grandmother who has a long history in real estate and she helped me find a commercial space. She purchased the building and we opened six months later. It was really fast. At the time (2014), there was nothing else on Tompkins Avenue. The building itself wasn’t abandoned, but the commercial space was, so it was pretty dilapidated. I put all my personal money into that; I hit the ground running and with the assistance of my mom and my grandmother, I was able to open the space. I worked with a limited budget because we’re not rich, we’re just hard-working women. And we’re savvy, so we’ve been able to create our own paths for that reason. I decided to have a cafe in the store because I thought it would help people feel more comfortable coming in, especially since I was the only business on Tompkins Avenue, aside from one restaurant. It was very, very, very new for the neighborhood and I wanted people to still feel comfortable coming inside. If you see a cafe or a coffee counter your initial thought is, “Okay, I can get coffee.” And then you discover it’s more than just coffee and can walk around and see what we’re doing.


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In terms of the location you chose, was it important to you to create a local business in Bed-Stuy rather than opening in Manhattan?

It was conscious in the sense that I’m from Bed-Stuy (my grandmother came here in the 1980s and then my mom came here when she was two and she’s 58), so I wanted something in Bed-Stuy, and I wanted to do things that were reflective of the community. But even with that, the community has changed so much. Because of gentrification, some of the natural energy that existed before has changed. Growing up, I saw people that looked like me walking around; there was a sense of comfort and a stronger sense of community. Now when I walk around I’m in the minority. That alone is mentally draining. It’s an attack on who we are as a people, and I don’t think a lot of people realize that—especially people who aren’t from here. There’s a strong history here; we created the energy, the culture…to see that not being respected, and seeing that we’re being pushed out, is really hard to bear witness to.

I have white friends who have bought their million-dollar Brownstone and they feel guilty, or they feel some kind of negative feeling because they know that they’re contributing [to gentrification]. I don’t really have an answer that would shift things, I’ve just been telling people that if you’re going to move [to a predominantly Black neighborhood], move there because you like the neighborhood, don’t move there just because it’s more affordable. Find ways to be involved in the community. Join your local block association. Most importantly, say hello to everyone that passes you by, especially on your block. That’s something that I’m just so used to. Growing up here I knew everyone on my block, the elderly people would babysit me growing up. We would all say hello and good night. Now I walk by people and it’s like they’re scared to look at me in the eye; that alone takes away from the sense of community that Bed Stuy is known for.  

So to answer your question, I definitely wanted it to be a local space but also something that could reach the masses, which it’s done. We get a lot of people who are from other countries visiting because they’ve read about it or they’ve heard about it. And I think that makes it that much more special. It’s for Bed-Stuy, but it’s also for young creatives and young entrepreneurs who like to create.

"I worked with a limited budget because we're not rich, we're just hard working women."

How has having to temporarily close the store due to New York’s stay-at-home orders affected the business?

We actually reopened the cafe a couple of weeks ago for takeaway coffee. I have a really wonderful manager who’s been manning it for me during limited hours—we’re doing 9 a.m. to 2 p.m. Overall, the impact is just a reminder that this government system does not support anyone who is not in the business of getting rich or big corporations. The loans that have been provided are backwards. I’ve definitely shifted the way that I approach my business and am just looking to be self-sufficient, which trickles into my life overall. Everything that I do from here is coming from the standpoint of being self-sufficient: I’m getting really creative with different ways to keep things running and keep giving our community content. It would be nice if we could use these times to just sit back and not be as concerned, but I think everyone is feeling the need to be productive. Which is counterproductive if anything.

Are you still doing online orders?

We are. I’m taking photos of myself to post on Instagram because we have inventory and I have to sell it. I’m kind of going back to basics from the early, early days, and just shooting things myself on my iPhone because my photographer is quarantined and I don’t want to ask anyone to come out. It’s being as resourceful as you possibly can.

Your next big venture was to launch Sincerely Tommy Eat and Stay, a boutique hostel and eatery. How have the plans for that changed due to Covid-19?

Honestly, I haven’t even been able to focus on that portion because it would require funding to get the permits. I know we’ll open, I just don’t know what opening is going to look like. The space itself is already done, it’s beautiful. It’s very representative of everything that I love: natural textures and a lot of special chairs that I designed, and then these really cool Bruno Ray stacking chairs. It’s like a mid-century meets shaker vibe. The restaurant is very Mexico with some influences from other countries I’ve visited in Africa. To me, it looks really different than Sincerely Tommy, I wanted to do something different.


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Renovations and designing my personal spaces brings me so much joy. This reno was my favorite because I was in there with the guys demo’ing, grouting, sanding, staining, etc. By the end of this year I’m determined to perfect my carpentry skills so I can put up my own sheetrock and 2 by 4. Love seeing a contractor’s face when he thinks women can’t do heavy work or don’t see the vision until the space is done. After and before pics from @getclever tour

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It must be so frustrating that it’s ready to go but that you can’t open it. There’s so much red tape that a lot of new business owners have to field.

Yeah, especially in New York, there are so many stipulations—certainly a lot more that weren’t around when I opened Sincerely Tommy in 2014. It seems like they’re cracking down a little bit more, which is very telling, especially considering what we’re dealing with right now. The city is not supportive of small businesses the way it needs to be, considering we make up so much of the workforce. We contribute so much to the infrastructure and helping things run, but we don’t get enough assistance and enough aid; we’re experiencing that firsthand right now.

How can the city better support small businesses?

They need to be giving out grants to every small business that pays taxes because we contribute so much to the economy—we need some kind of bill that will make up for the lost revenue, not only for employees who now won’t be able to pay their bills and live, but also the for business owners; I don’t think people realize when you’re running a small business you’re the last person to get paid.

As far as I know, the only grant that’s available is the one that covers 40 percent of payroll, which is great, but for businesses forced to close because of the non-essential mandate, there’s nothing else other than loans and that’s just not realistic. No one wants to be paying anything back, especially not knowing what the next year is going to look like. It’s putting us deeper in a hole.

"This government system does not support anyone who is not in the business of getting rich."

Have you had to lay off any of your staff at this time?

Yeah, when we were closed no one was working, and now, because the government urged everyone to file for unemployment, most of my team members are on unemployment and making more than what they would have been making working at my business. I’m not going to urge anyone to come back if they have to forfeit $1,100 a week. It’s again just another sign that they [the government] are not looking out for small businesses.

I have the manager who runs the cafe and one other team member who has been able to come in one day a week to help me ship out orders. Otherwise, it’s a very small team right now and I’m not sure what the future looks like in terms of bringing back a full staff; or if that’s even a good idea. They still haven’t addressed whether or not the percentages that small business owners pay towards unemployment insurance will be going up as a result of all these new unemployment applicants. Right now, if you’re a small business in New York, you pay something like seven percent bi-weekly when you run payroll. That percentage is set to go up because we have to be able to cover all these old employees’ unemployment rates and that’s ridiculous because we’ve been closed. Now that we’re open, we’re trying to get back on our feet and it’s is just crazy. This whole thing has put so much into perspective and shed a lot of light.

"I want to create a self-sufficient economy for the Black community and contribute to that."

What has been the most important lesson you’ve learned through all of this?

Maintaining my mental, physical, and spiritual health has been a priority. Not only as a business owner, but as a Black woman, a Black human. We’re being tested again—I mean we’re tested every day but this week especially. It’s a reminder to continue to take care of myself, but it’s also a reminder that there’s a lot of work to do. I want to create a self-sufficient economy for the Black community and contribute to that. I recently joined The African National Women’s Organization (ANWO), an organization that I feel really passionately about. Their mission is to fight colonialism from the ground up through an African woman’s perspective. It is only for African women but they work under the African People’s Socialist Party and they have another chapter for white people who want to support. They pay reparations and help to build a separate economic system for the Black community and so far they’re one of the only organizations that I’ve seen—I mean, there are a few other grassroots organizations—that are really doing the work and touching on every issue. One thing I’ve seen this week is that there seems to be this focus on tackling the surface issues like police brutality, but police brutality is only a symptom of the overarching root problem that exists in this world. We can call police precincts and District Attorneys but that’s not going to stop the next event from happening. It’s been challenging to navigate this whole thing, I have a Black son as well so I am constantly thinking about what that looks like and protecting him and arming him with information and knowledge so that he can navigate this world feeling empowered.


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Between running a company and being a mother, you essentially have two full-time jobs.

Yeah. I guess I could call myself a single mother. It’s not really a term that I use, but I have a co-parent partner who lives two blocks away. We’ve been switching days and figuring out a schedule that works based on what we have going on. I was already thinking about shifting the way I worked and this has given me a bigger opportunity to figure out what that looks like for the long term, or at least the next couple of years. The way I have been working isn’t sustainable, but also, more importantly, I want to be present for my son and I want to be able to give him what he needs during his more formative years. I’ve been having a lot of conversations around restructuring things.

What would that look like?

In my ideal perfect world, not being in New York full time anymore. My mom recently opened up a wellness space in Grenada, which is where she’s originally from. I’d love to be down there for a better portion of the year with Che. Everything feels so heavy right now in the U.S. and Grenada is in the Caribbean; it’s such a beautiful, calm island and you’re just surrounded by lush plants and greenery and good food and good energy and there are beaches. Everyone is kind of needing some lightness right now, so I’m blessed enough to be able to go there when I want to. For a child, it’s so important that we’re intentional with the energy we surround them with.

"I have a Black son so I am constantly protecting him and arming him with information and knowledge so that he can navigate this world feeling empowered."

Is that a difficult thing to do, letting go of some of the reigns of the business and handing those keys over to someone else?

Maybe two years ago I would have said that. But from more of a spiritual perspective, two years ago I was in a place where Sincerely Tommy felt like so much of my personal identity that the idea of giving a part of it up or shifting my role in the business would feel like I’m essentially giving it up. But it was part of my identity so much that I was forgetting who I was, and I think with motherhood, as many women will probably say, you’re reborn; it’s the biggest mirror that you’ll ever have. So now I have a different view on the business and I look at it as something that I have created, and I feel blessed to have the ability to navigate and structure it the way I want to. My mindset is: I have created this space and the only way it can grow is if I give up a part of it. But I don’t even look at it as giving it up, I’m looking at it as allowing it to grow. So if that means bringing on someone who can help me grow things in a way where it doesn’t require me to be as present, that is something I look forward to and I’m excited about. It will, if anything, allow me to focus more on the creative.


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My sis @seaayala once said “I’m learning not to impose motherhood on my daughter”. Those words stuck with me as I navigate motherhood – co creating my experience as an individual and a mother while being intentional in giving Che the freedom to explore his own path .”And the children will belong to all because they belong to existence”.

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Do you have help with childcare while running the business?

I have a nanny. She comes Mondays through Thursdays. But I work from home so I’m with Che 24/7 for the most part. [My nanny] is really good about taking him out on play dates and to the library so I get some moments during the day to be alone or just take a nap; as most moms know, sleep is the number one thing we are deprived of. But yeah, I do have help, which has been so incredibly amazing because the first four or five months of Che’s life I was trying to do both: taking care of him and going to the store. I would bring him with me sometimes; it was a lot, and it wasn’t sustainable. I was exhausted. So I hired a nanny after a while, and it’s been so incredible to have her and also another blessing because it makes me think about mothers who aren’t in a position to do that and who have to figure out how to go into work full time and take care of their children.

Did you take maternity leave for yourself?

I didn’t. In fact, the day after I was released from an emergency C-section I was up in the department of buildings because we had a hearing for fines that we got. I had to go in there and I could barely walk.

How did you manage that?

It had to get done. It’s just another example of how small businesses don’t get the support that they need; the city will literally fine you for the most insane things. We got a $600 fine because the barista on staff had just taken her food handler license course and they are supposed to give you a receipt once you’ve completed it, but no one told her that she was supposed to keep the receipt on her until her actual license came in. So an inspector came in to the store and she didn’t have the receipt on her. They are supposed to look the receipt up in the system, but the inspector’s little machine that they had on them wasn’t working and yet we were still fined $600. I don’t understand how companies like Amazon get a billion-dollar tax break, yet we’re struggling to figure out how to pay taxes every quarter.

Wow. So you just worked all the way through the first three months postpartum?

Yeah, I was working all the way through—and through my entire pregnancy.

Do you have advice for other women running their own business who also can’t take maternity leave?

As of right now, I don’t know that I have advice because it was really, really hard for me. I was so overwhelmed. But I think, if anything, I would say try to be really mindful of your self-care and prioritizing yourself. We’re so overwhelmed and consumed with providing for our children that we forget about ourselves or don’t even think to take care of ourselves. That’s something that I realized, be gentle with yourself, be forgiving. Self-forgiveness is such a key thing that I think a lot of us just don’t realize.

"I don't understand how companies like Amazon get a billion-dollar tax break, yet we're struggling to figure out how to pay taxes every quarter."

Would you ever seek outside funding to help you through this crisis?

[Bootstrapping] works to a certain extent depending on how you want your business to grow. I never pictured Sincerely Tommy just being this retail space, for me, it was more of a lifestyle brand: a restaurant, a hostel, a furniture line. We’re doing so much with such limited resources, so to really evolve the brand I’m trying to team up with some VCs and angels because we need more resources. I’m in the very, very early stages. It is really important to me that I find someone who understands the way that I work and understands my vision.

I’ve been working with a really great partner on the furniture brand; he and I have been taking some meetings with VCs and it’s such a new process for me. I was really intimidated at first. I had this perspective of like, “I don’t want to be asking people for money.” But my partner flipped it around to, “We’re not asking people for money, we’re giving people an opportunity to make money.” That really helped me shift my thinking around it. I was pretty hesitant to take on a partner because I’ve had partners before and at some point, someone always ends up wanting more or it just doesn’t work out. I’ve always wanted a partner who could be the business person so I could remain the creative; we have a good synergy with that. It’s been really fun, I’m really excited and optimistic about seeing how things will grow from here.

Was it difficult to bring on a partner? How does that work contractual wise, bringing on a partner or a co-founder so late into the business?

That’s a good question. He’s actually just my partner with this new furniture brand, not on Sincerely Tommy. If I was to take a partner on Sincerely Tommy, it would probably be someone who is a VC because they would be investing a great deal of money into it. But in terms of taking on this partnership with the new furniture business, I look at it as a new venture that I’m taking on. He is bringing in a lot too and we definitely don’t share equally percentage-wise, which is something that I really appreciate. From the very beginning, it felt like I’m collaborating with someone who wants to be a part of what I’ve created versus someone who wants to co-create; he really respects my vision.


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New items on SincerelyTommy.com

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We know that the VC system funds women of color at much lower rates than white women. Since 2009, Black women-led startups raised just .06 percent of the $424.7 billion in total tech venture funding. (In comparison, white women raised 2.7 percent) Have you encountered any difficulties as a Black-owned business?

So far, I haven’t had enough experience to say that I’ve had negative feedback, or anything directly correlating with me being a woman of color. But through being a woman of color business owner with Sincerely Tommy, I’ve definitely encountered many experiences, whether through staffing or through other brand collaborations, things always have come up.

What kind of things?

The fact that I’m a young business owner too has always presented a challenge with staffing; it’s hard to set boundaries with people who are essentially a few years younger than you or maybe even your age. There’s always been challenges in setting the tone for employees. With brand collaborations, there’s been many instances where I’ve felt taken advantage of or exploited, where either I’m not paid or not paid on time, or I know that I’m being chosen to work on a brand collaboration because I represent a certain demographic that fills a void for the company that has hired me.

"As a black woman, when you speak up about injustices you're experiencing, you're categorized as being angry or upset or bitter. There's always a negative connotation with it."

You mean tokenism?

Yeah, exactly. I’ve taken meetings before with people who I can tell haven’t even bothered to familiarize themselves with my work, and they automatically assume that I have a sportswear brand or a streetwear brand because people of color are often categorized with streetwear or sportswear. I’ve experienced many different kinds of things. In the beginning, I let it go and I would try not to say anything, but I’ve learned to speak out about it. So much of it is these microaggressions; a lot of brands or the people on the team don’t even realize they’re creating this atmosphere for these experiences to happen. It’s unfortunate because often, as a black woman, when you speak up about these injustices that you’re experiencing, you’re categorized as being angry or upset or bitter. There’s always a negative connotation with it. Overall, the way black women are approached is just always different. We’re kind of at the bottom of the barrel.

What does the future of Sincerely Tommy look like?

So far I’ve been able to separate who I am from the business itself; I know what I’ve created and I’m so proud of that, but my priorities and what I want my life to look like has so drastically shifted—just from having a child and also being really conscious of what he holds to be important. I want him to see me working well but I also want him to see me working because I enjoy what I do. And understanding that I choose to do what I’m doing because it brings me happiness but not because I’m working to live.

With all of these decisions, it’s to create a life where we can have comfort. And it’s kind of interesting too because a lot of the conversations that I’m hearing with everything that’s going on, it’s like the capitalistic model that exists right now is obviously not working. We can see now how many people are living hand to foot. I’m curious to see if things will shift at all when it comes to how businesses function; how we’re living and using money. But for me, I really want to instill in Che that there is more to life than working and making money.

Lauren Alexis Fisher is a freelance writer, digital strategist, and creative consultant. She was formerly the digital fashion editor at Harper’s BAZAAR.

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