Chasity Cooper | Episode 007 | Your Bougie Wine-Loving Cousin

wine
Written By Jeremy Mckellar

An In Good Company Feature | By JermConnects

How Chasity Cooper Built a Career at the Intersection of Wine, Culture & Storytelling

Most people don’t trace their career back to a fictional character drinking red wine on network television. Most people don’t leave a stable job in the nation’s capital for a city where they have no offer, no plan, and no safety net. And most people definitely don’t go from blogging on the side to writing for over 30 major publications, getting named a Wine Enthusiast Future 40 Tastemaker, and publishing a book with one of the most respected publishers in the country. But Chasity Cooper isn’t most people.

On the latest episode of In Good Company, I sat down with Chasity — wine culture expert, award-winning journalist, published author, and CEO of Cheers To That, LLC — for a conversation that went way beyond wine. We talked about trusting yourself when nobody else does, what it means to build a career in an industry that wasn’t built for you, and why the world needs more in-person connection now more than ever. As a wine lover myself, I came into this conversation hoping to learn. I left with a lot more than I expected.

Madrid & Scandal

Chasity’s wine story doesn’t start in a vineyard or a tasting room. It starts on a bus in Spain. During the summer of 2010, she was studying abroad in Madrid through Syracuse University. The World Cup was happening. Spain was electric. And on one of the last excursions before the trip ended, the group visited a winery.

“That experience is still so visceral,” Chasity told me. “I remember getting off the bus and how dry it was, seeing the vines, going through the cellar, pairing the Spanish wines with the Spanish cheese.”

She was 21. She’d never been to a proper winery. Growing up in Evanston, Illinois — and before that, Galveston, Texas — wine wasn’t on the table. At cookouts, you might see Yellowtail or Barefoot, but that was the extent of it. Madrid changed everything.

But the spark didn’t ignite immediately into a career. It simmered. After graduating, Chasity moved to Washington, D.C. and built a career in communications and marketing. She was blogging, writing for publications like Teen Vogue and The Root, and co-leading the D.C. chapter of Levo League. Wine was still a passion on the side — until Olivia Pope showed up.

“Scandal comes on TV. Olivia Pope is rocking the trench coat, walking around the nation’s capital, and she’s drinking great wine and eating popcorn for dinner,” Chasity recalled with a laugh. “It was such an incredible opportunity for me to see representation of Black women enjoying fine wine.”

That representation mattered. It wasn’t just entertainment — it was permission. Permission to see herself in a space that had never been marketed to her.

The Wine Shop

The real turning point came in 2017 when Chasity reached out to a wine shop in D.C. called Grand Cata — a store specializing in Latin American wines. She offered to apprentice. They offered her a job instead.

Working there surrounded her with people who lived and breathed wine. One day, the owners assigned a rotating exercise: take a bottle home and write tasting notes. Chasity did what she does best — she researched, she wrote, and she sent a beautifully crafted paragraph to the entire team.

“One of the owners was like, ‘You wrote this?’” she said. “Being affirmed in that moment, I was like, okay, there’s more to this.”

That affirmation was the catalyst. She started studying for her WSET certifications — passing Level 1, then securing a scholarship from E. & J. Gallo that funded Levels 2 and 3. She earned her WSET Level 3 with merit during the pandemic, and now, five years later, she’s still pushing forward. The DipWSET — one of the most demanding certifications in the wine world — is on pause, but not abandoned.

“I’ll eventually return to my diploma journey,” she said with confidence. “Right now I’m still very much focused on connecting people to authentic experiences in wine.”

Taking a Leap of Faith

In 2017, Chasity made a decision that still defines her trajectory. After nearly six years in D.C., she decided to move to New York. She applied for jobs, got a verbal offer, packed up her apartment, found a place to live — and then, one week before the move, the offer was rescinded.

She moved anyway.

“I told my mom, and Black moms are very much like, ‘Who do I need to go fight?’” Chasity laughed. “I was like, hey, I’m 28. It’s fine. I’m still gonna move to New York.”

That decision — the one everyone told her not to make — opened up her world to New York’s wine renaissance. She connected with Black-owned wine shops in Brooklyn, experienced the city’s emerging wine bar culture, and strengthened her writing. The woman who showed up in New York with no job offer left as a published wine journalist with a growing reputation.

“Trust Yourself”

When I asked Chasity what she’d tell her younger self from five years ago, she didn’t hesitate:

“Leave the job that’s making you unhappy. Get really clear on how the work you want to do aligns with how you want to feel. And stop doing things just because people say you should.”

During the pandemic, she stretched herself thin hosting virtual wine tastings while working full-time — sometimes running two computers simultaneously during the holiday season. Everyone told her it was great money. She wasn’t feeling it.

“After a while I was like, is this really what I want to do?” she said. “I really did miss being in community in person with people.”

So she made the difficult choice to leave a toxic job, sunset the virtual tastings, and bet on herself. She traveled to Eugene, Oregon for a wine writers conference. She spent 10 days in Italy for a Classical Bootcamp. She went everywhere, met everyone, and proved to herself that her voice and expertise had value.

“I’m grateful I get to choose now,” she told me. “I don’t have to do all the things. If it aligns with where I’m at and what I want to learn, I get to choose.”

Wine Culture Expert — Not by Accident

Chasity doesn’t call herself a sommelier. She doesn’t call herself a wine critic. The title she chose — Wine Culture Expert — was intentional and deliberate.

“Wine culture expert kind of encompasses all of that,” she explained. “I love wine. I love making cultural references. I love this notion that I get to have this expertise, but I’m constantly learning.”

It’s a title that bridges the gap between credentialed expertise and cultural storytelling. She’s not just tasting wine — she’s placing it in context. She once pitched the Chicago Tribune on pairing Chicago’s most iconic foods with wine — deep dish pizza, Italian beef, jibaritos, Garrett's popcorn — and turned it into a story that connected food culture, neighborhood pride, and wine education in a single article. That’s the lens she brings to everything.

The Real Problem She’s Solving

When I asked Chasity what problem she’s trying to solve right now, she didn’t talk about followers or algorithms. She talked about something much bigger: getting people back together in real life.

“I want to get back to the essence of wine itself, and that is people connecting over bottles in person,” she said.

Last May, she partnered with a friend to organize a wine walk across four locations in Logan Square, a Northwest Chicago neighborhood. People who might never have crossed paths came together, talked about wine, shared their experiences in the city, and built connections that wouldn’t have happened through a screen.

That’s the vision. More tables where real people sit down, pour something interesting, and actually talk to each other. In a world that’s increasingly digital and disconnected, Chasity is betting on the opposite — and I think she’s right.

One Kind Thing

Every In Good Company guest gets the same closing question: If you could ask the world one question and get an honest answer, what would it be?

Chasity’s answer stopped me:

“If someone could do one kind, thoughtful thing for you — just one, right now in this moment, wherever you are — what would that be?”

She explained that it would give people the chance to pause, to center their own needs for once, and to remember what it means to be human. In a world defined by division, noise, and endless to-do lists, she’s asking us to return to something simple: kindness.

“Returning to humanity is what we all need to strive for,” she said. “Kindness, being compassionate, extending grace and generosity.”

What’s Next for Chasity Cooper

The wine walks are coming back this spring in Chicago, with a possible expansion to her hometown of Evanston. She’s planning a trip to Germany to explore Riesling country and the sparkling wines known as Sekt. Her Substack newsletter, called Palette Cleanser, is becoming her primary space for wine-adjacent writing that connects wine to spirituality, emotions, and how she navigates life. And her book, the Wine Convo Generator, turns two in March.

She’s also recently returned to corporate work, finding her balance between the job that pays the bills and the work that feeds her soul — a tension that anyone building something on the side will recognize immediately.

Chasity Cooper didn’t wait for the wine world to make space for her. She built her own table and invited everybody to sit down. That’s what this show is about. That’s what being In Good Company means.

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Jeremy Mckellar
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Alton Peques | Episode 006 | The Rise of the Multi-Hyphenate