Breaking Barriers, Uncorking Legacy: One Woman’s Bold Journey to Success

I’ll never forget the first time I saw Chrishon. It was during the height of COVID, yet her energy cut through the uncertainty like a beacon. She had already faced what could have broken most people—a flood that destroyed her Chicago art and wine bar—but instead of giving up, she rebuilt, reimagined, and dared to leap. What makes her story extraordinary isn’t just survival; it’s that she built a nationally distributed wine brand as a Black woman in a male-dominated industry, challenging assumptions, breaking barriers, and creating space where so many had been excluded.

Fast forward to today, and I am beyond humbled that Chrishon is sharing her journey with The Possible Woman. From a blog called Love Cork Screw, started simply to stay connected with her loyal customers, to a brand that now sells over 2 million bottles, hosts inclusive festivals, and sparks connection across the country—her vision has always been clear: make wine accessible, fun, and human. Her story is a blueprint in courage, resilience, and leadership—not just in business, but in life.

Meet Chrishon Lampley: trailblazer, innovator, and the woman rewriting the rules in an industry that was never built for her.

You’ve had a remarkable journey—from founding LOVE Corkscrew to driving impact via your personal brand. What key moments or decisions ignited your leap into entrepreneurship?

My leap into entrepreneurship wasn’t mapped out, it was survival mixed with passion. A freak flood destroyed my art and wine lounge in Chicago, and overnight, everything I’d built was gone. But my customers didn’t forget me. They kept asking for wine recommendations, so I started a blog, Love Cork Screw, just to stay connected. That blog turned into a radio show, and then into the wine brand you see today. The turning point was realizing people weren’t just listening; they trusted my voice in this space. That’s when I knew I had the vision, the experience, and the drive to build something different.

What were the most significant challenges you faced in the early days, and how did you navigate them with resilience?

Breaking into wine as a Black woman is not for the faint of heart. I knew there would be barriers, but I didn’t realize how high they’d be. Access to capital was the biggest hurdle, I watched brands with less product, less experience, raise millions while I had to bootstrap every move. The assumption that Black-owned businesses aren’t “ready” is real. But I leaned into my 20+ years in sales and distribution, stayed laser-focused, and refused to dim my voice. That’s how I built a national brand distributed in 19 states, with grit and authenticity.

You’ve led growth in multiple ventures—what lessons from LOVE Corkscrew directly informed your leadership and culture-building?

Love Cork Screw taught me that authenticity creates community. I made a choice early on to strip away the wine industry’s pretentiousness and speak directly to people who felt excluded. That decision shaped how I lead, valuing collaboration, open communication, and inclusion, to guide everything we do. Our culture isn't just internal; you feel it in every bottle, every label, and every interaction.

As a woman in entrepreneurship, how have your lived experiences shaped your vision and approach to business?

For most of my journey, I was the only Black woman in the room. Sometimes the only woman, period. That experience gave me resilience, but it also gave me purpose. Representation matters. Love Cork Screw was built for the people who weren’t invited to the table. My lived experience shows up in our messaging, packaging, partnerships, and every detail. I’m not here to blend in. I’m here to change the narrative.

How do you balance ambition with self-care? What practices keep you grounded and energized?

I honor the pause. Cooking, traveling with my husband, unplugging. It’s non-negotiable. Burnout isn’t a badge of honor. Self-care fuels success.

How do you define success in sustainable and holistic terms—for yourself and for other women entrepreneurs?

Success is legacy. It’s not just revenue; it’s about impact, opening doors, and leaving proof for the next woman that yes, there’s space for her too.

In turning points, when intuition calls and logistics resist—how do you tune into that inner voice and pivot?

My gut has never failed me. Some of the biggest wins weren’t on a spreadsheet, they came from instinct. When logic says “wait,” but your heart says “go,” that’s often the breakthrough moment. If it aligns with my values and purpose, I leap.

Your brand deeply prioritizes authentic connection—how do you foster that sense of community across digital and in-person experiences?

Love Cork Screw is more than wine; it’s a mood, a movement. Our labels spark nostalgia. Our voice is fun and approachable. And our events, like Clink Festival, bring people together. It’s about bringing people together, making them feel seen and welcomed.

How do you elevate other women through your work? Which initiatives have been most transformative for your community?

Clink Festival is one of my proudest impacts. Co-founded with Joyce Dawkins, it’s Chicago’s first BIPOC-led wine and spirits event, and in just four years we’ve showcased 50+ minority-owned brands to thousands. It’s about more than my seat at the table, it’s about keeping the door open.

In your creative process, how do you generate fresh ideas that resonate with your audience and align with your mission?

Fresh ideas come from listening to customers, to culture, to community. Our wine names like “We’re Movin’ on Up” and “The Morning After” aren’t just fun, they spark connection. I watch how people respond to moments and moods, then build around that. Innovation doesn’t have to be complicated; it just has to be human.

With the intersection of AI and entrepreneurship—and you being keen on integrating innovative tools—which emerging tech excites you most for women-led businesses?

I’m especially excited about AI personalization and AR tastings. Imagine recommending wines based on someone’s mood, Spotify playlist, or dinner plans, that’s where we’re headed. And while we embrace tech, we never compromise our values.

What strategies have you used to scale your ventures while maintaining brand integrity and human-centered values?

I’ve been intentional about who we partner with. Every partnership, from woman-owned distributors to giants like Total Wine & More, H.E.B., and Midway Airport, has to align with our mission. Scaling doesn’t mean diluting. It means amplifying.

Have there been times when you had to pivot your business model or direction? How did you recognize the need, and what helped you recalibrate?

I’ve had to pivot plenty of times. The flood forced me to rebuild from scratch. When retail support for Black-owned brands slowed after 2020, I doubled down on creating my own lane. That’s how Clink Festival was born. When you sense that momentum shift, you don’t panic, you innovate.

How do you approach risk-taking—and what’s been the most daring bet you’ve made in business that paid off?

The boldest bet I made? Launching Love Cork Screw with no outside funding. I used every connection, every experience and made it happen with sheer grit. That risk turned into a nationally distributed brand.

Where do you seek community and mentorship for your own growth, and what powers your continued learning journey?

For growth, I surround myself with sharp people and hard truths. Utilizing programs like Goldman Sachs 10,000 Small Businesses, Tuck School of Business, FedEx E-commerce Learning Lab to give me the tools. But mentorship, both giving and receiving, keeps me learning.

What advice would you give to a woman entrepreneur standing at the threshold—believing her dream but fearing its scale?

To the woman standing on the edge, scared of her dream’s scale: do it scared. Fear doesn’t mean you’re not ready, it means you care. Start where you are, use what you have, build as you go, and don’t wait for permission. If the table wasn’t built for you, bring your own chair.

If you could go back and whisper one piece of wisdom to your younger entrepreneurial self, what would it be?

You are enough. Even in the rooms where you feel like an outsider, you belong. Your difference is your superpower. Own it and don’t shrink.

Looking ahead, what’s your aspiration for the legacy you're building—and how do you hope other women entrepreneurs tap into that narrative?

I want Love Cork Screw to be proof that failure doesn’t disqualify you, it sharpens you. That success isn’t just about sales; it’s about paving the way for the next woman. My hope is that our story sparks courage in women, Black entrepreneurs, and dreamers everywhere to take the first step, to keep going, and to build something lasting; their voice belongs in any room, even if they have to pull up their own chair to the table.

To Learn More about Chrishon, visit:

https://www.lovecorkscrew.com/

https://www.linkedin.com/company/lovecorkscrew/

https://www.instagram.com/lovecorkscrew/

https://www.youtube.com/@LoveCorkScrew

hhttps://www.lovecorkscrew.com/