For 'Wine-Down Jazz Nights' host, helping unhoused single mothers is personal

It's a warm Saturday evening in September and guests are streaming into Library Tavern in Brightwood Park, ordering cocktails and making small talk. In the intimate basement lounge, a jazz trio sets up drums, a guitar, and a standing bass.

Skyler Kelley shuffles around trying to make sure everything is just right — it's the first time one of her Wine-Down Jazz Nights is taking place indoors. But even when she held them outside in her friend's backyard, the twice-a-month events were always cozy and welcoming. Kelley is known to pass out complimentary wine and her own homemade fresh juices to audience members. For $12 a ticket, guests are transported to a night of hospitality and good vibes.

"I'm in my element when I'm like, 'Hi, how can I help you?'" she says. "That's just me."

Kelley, 27, began hosting the jazz nights a year ago as a way to support people like her: single mothers who've experienced or are experiencing homelessness in D.C. Kelley often asks ticket holders to bring donations for gift cards to the supermarket Aldi and supplies like diapers and wipes to hand out to mothers in need. But the jazz nights are just a prequel to a set of grander ambitions, including her goal of becoming a "social entrepreneur," running her own nonprofit and coffee shop, and of inspiring other women to follow in her footsteps.

When she's not serving up coffee as a barista at Peregrine Espresso in Union Market, the Germantown, Md. resident is fundraising for the future Brij Coffeehouse & Juicebar, a coffee shop of her own she plans to open in Northeast D.C., if things go her way. Her goal is to raise $250,000 through grants and a GoFundMe campaign so she can launch her business, perhaps inspiring other Black business owners to join her. (She has raised just over $3,000 so far.)

Kelley is working with a real estate broker who is shopping around for a storefront for Brij in the Union Market area, she says.

She's also on the hunt for a location in Brookland, preferably a large home, to be the headquarters for Emma's Place, a drop-in day center — named after her daughter — that will provide social services, case management, computer access, toiletries, and a general safe haven to mothers with unstable housing. Kelley says she's further along in her efforts to get Emma's Place up and running, though she's spending equal time on both projects. She envisions Brij's profits helping to fund Emma's Place, similar to Ebenezeers in Capitol Hill, which serves "coffee with a cause" in support of National Community Church's outreach programs.

In Kelley's dream of dreams — and in the pitch deck she's delivered more times than she can remember — Emma's Place will have case managers who can connect clients with classes, mental health resources, employment services, and housing opportunities. While mothers work with their case managers, Kelley says there will be a play space where licensed professionals will look after kids. If families need to use a restroom or a shower, they'll have access to one. Kelley equates it to some of the day service centers run by the D.C. Department of Human Services, or Catholic Charities' low-barrier shelter for men, Adam's Place.

While the opening timeline for both are in flux and depend on when she can raise the startup cash, secure physical locations, and start hiring employees, Kelley hopes to get Emma's Place up and running by this time next year.

Kelley came to D.C. in 2015 from Atlanta to help expand a church network to the D.C. area and worked shifts at a coffeeshop in Adams Morgan, fueled by her love of coffee and people.

But just before the church opened, Kelley says she was sexually assaulted. Later, she found out she was pregnant with Emma, and she moved back home to Atlanta to be with her family. But she says God called her back to D.C. in 2017; her mission here wasn't complete. In fact, it had just begun.

"As a Christian, I don't believe in coincidences, I believe everything happens for a reason," Kelley says. "When I went back to Georgia, all the doors closed, and I knew it was the Lord saying, 'Go back to D.C.'"

Kelley and a 1-year-old Emma spent many nights sleeping in a car in a Walmart parking lot, while Kelley looked for work as a barista by day, eventually finding a job at Rise Bakery in Adams Morgan. She had experienced homelessness before, sometimes secretly sleeping in her grandmother's senior living apartment as a college student in Georgia.

Emma was named after her grandmother, who also experienced homelessness. Kelley remembers moving from one shelter to another with her own mother as a child.

"All of my family, we've experienced homelessness, in and out, in and out, all of my life. This is the most stable I've ever been, actually," she says. "So, it's very generational, and I am looking to break that. I would love for Emma to grow without having to experience homelessness again. She experienced it the first year of her life and that's it. I don't want that to ever happen again."

In 2017, Kelley first learned about Relisha Rudd, the 8 year old who went missing from a D.C. family homeless shelter in 2014. Kelley remembers thinking about Rudd and her mother, and wondering what resources could have resulted in a different story. She says Rudd's disappearance made her think of Emma and presented her with a clear mission.

"I thought to myself, 'Had her mother had a safe place, I really believe Relisha would still be here," Kelley says. "So Emma's Place is going to be that safe place."

Emma is now an energetic 5-year-old who is starting kindergarten this year. She's a "bundle of joy," Kelley says, and the reason she is working so hard to make Brij and Emma's Place a reality.

Kelley has registered Emma's Place as an official nonprofit and is represented by lawyers at Bailey Glasser, a firm with locations in D.C. and throughout the U.S. that's helping her sort through some of the legal work involved in starting an organization. She's preparing to host a fundraiser at Pinstripes, an upscale bowling lounge in Georgetown, by the end of the year. (Kelley says she put a deposit down to host an event there earlier in the year, but the pandemic postponed her plans.)

It's Kelley's first time operating as an entrepreneur, and so far, she's run into plenty of hurdles along the way. She says people have been slow to help her because of her lack of major funding and real estate.

"It's moving a little slow, and that's OK," says Kelley. "Once I have the lease, I really believe we can get things moving. A lot of people are like, 'We would love to help you, but do you have a building yet?'"

In the past month, she's met with Marisa Flowers, Ward 5 Councilmember Kenyan McDuffie's chief of staff, to talk ideas and to connect with other non-profit leaders in Northeast who can offer some guidance. She's also reached out to restaurant owners and local business accelerators and is applying for a grant with the DC Kiva Hub, a microlending program within the Department of Small and Local Business Development.

Resources are available to women experiencing homelessness in D.C., Kelley says, but they're not always obvious and they often require applications, reliable transportation to show up on time for programs, and, more than anything, a mindset of truly wanting to improve one's situation.

She says that when she was looking for stable housing she had to "dig" to find opportunities, such as a free class in hospitality offered through the Temporary Assistance for Needy Families (TANF) program. That class landed Kelley a job interview with Marriott, where she worked until getting laid off at the beginning of the pandemic. She received free mental health services through the Friendship Place shelter in Northwest D.C. But many women she met in her first years in D.C. were unaware these programs existed.

"Some people are just exhausted. They're tired. They're worried about their day-to-day life, where they're going to sleep, not what class, where [to go], and what time they should be going to the TANF office," Kelley says. "So, [Emma's Place will provide] just a push from a local organization to get them on their feet."

Back at Library Tavern, as the Julian Berkowitz Trio glides through a set that includes jazz standards like "Emily" and "There Will Never Be Another You," Kelley seems lighter — like she can finally relax. An employee sets up a video so that mini fireplaces appear on the flatscreens that adorn the walls. Guests enjoy complimentary bottles of wine and a mix of Persian fare (kabobs and hummus) and New Orleans-inspired dishes (Andouille sausage mac & cheese, gumbo) from the kitchen. Taking it all in, Kelley is smiling.

Music, she says, helped her relax on some of her toughest nights in D.C., when she was balancing being a new mother, working shifts as a barista, and trying to figure out her purpose: "I would listen to it, light my incense, sit with a glass of wine, and it would just help me mentally."

Before the pandemic, Kelley would visit local restaurants and jazz clubs to listen to artists. One night, she searched "#DCJazz" on Instagram and saw a video of Berkowitz drumming with his trio and decided to reach out. He told Kelley about how jazz musicians have struggled to book live gigs in the past year as club after club closed in D.C. Kelley came to one of Berkowitz's shows and soon, he agreed to help her book artists for her jazz nights.

Kelley's friend Mike Kurtz, a local comedy show host, then connected Kelley with Library Tavern owner Jay Butler, who agreed to let her host the shows at the lounge.

"I thought about the impact that the closure of the jazz restaurants had on these artists who now had no money," Kelley says. "I would love to be part of giving back to the jazz community in D.C."

Kelley still doesn't believe in coincidences. That's perhaps why, in 2020, she found herself looking through old journals and found an idea written hastily, scribbled on one of the pages. It read, simply, "Coffee shop."

After she was laid off from Marriott last April, among the company's pandemic-related lay-offs, Kelley started working on Brij. She came up with the name while looking up synonyms for connect. (She wants people to connect over coffee and her homemade juices.) She saw the word bridge and its phonetic spelling, brij, and thought it looked cool enough to catch on in D.C.

It won't be an easy road to being a successful entrepreneur, but nothing about Kelley's journey so far has been easy. "There were times I wanted to quit life," Kelley says. "I mean, I'm not gonna lie and say it was gravy. It really wasn't."

Plus, she says, moving back to Atlanta isn't really an option. She used to think about leaving D.C. often, while trying to stay warm in her car. But now, her mission is clearer than ever before.

"I might as well stay up here in D.C.," she says, "where I know I'm called."

This story is from DCist.com, the local news website of WAMU.

This article is part of DCist's 2021 contribution to the DC Homeless Crisis Reporting Project, in collaboration with Street Sense Media and other local newsrooms. The collective works will be published at DCHomelessCrisis.press. You can also join the public Facebook group or follow #DCHomelessCrisis on Twitter to discuss further.