Story to Scale: How to LEVELUP Your Brand Through Storytelling — Live Podcast Event Recap

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New York, NY – On the evening of April 16th, LEVELUP in NYC founder Ryan McBride brought together one of the most compelling panels the community has seen yet — three founders who built their brands not on massive marketing budgets or venture capital, but on something far more personal: their stories. The live podcast taping at Palma Verde in Times Square drew an engaged crowd eager to learn how authenticity, community, and strategic thinking can turn a passion into a scalable brand.

Here's everything that went down.

The Guests: Three Founders, Three Paths

Charles KuyKendoll — Founder, Oxtail Off & Charles Beloved Productions

Charles KuyKendoll is a serial entrepreneur whose journey reads like a masterclass in recognizing cultural gaps and filling them. He's the creative force behind R&B House Party — the iconic event brand he started in college, scaled to two cities, and ultimately sold to Black media company Blavity in 2023. Post-acquisition, Charles pivoted once again: first to the Oxtail Off, a nationally touring food festival celebrating Caribbean cuisine and community, and then to AutoTune Karaoke, a high-energy live music experience. His business partner and advisor, Kareem Edwards, has been with him since college.

Kareem Edwards — First Black Chick-fil-A Owner-Operator in Chicago

Kareem Edwards has one of those résumés that seems almost impossible: Wall Street at Lehman Brothers, business school, marketing at Kraft Heinz, Google — and then he walked away from all of it to become the first Black owner-operator of a Chick-fil-A franchise in Chicago. A Queens native (Far Rockaway) and University of Michigan alum, Kareem brings both corporate rigor and deep community values to everything he builds. His partnership with Charles KuyKendoll as a business advisor is a case study in creative-analytical balance.

Rashan Brown — Founder, Poetry Me Please

Rashan Brown built poetry me, please into the country's largest poetry showcase series — one showcase per month, averaging 200 guests per flagship event, and a landmark sellout at the Apollo Theater with over 1,600 in attendance. He did all of this while working full-time, first as a STEM teacher, then in EdTech, and now at Disney ESPN. His model — providing poets with high-quality content to build their digital portfolios — turned a passion for performance into a scalable, community-driven brand.

The Experience: Poetry and Live Art

Poet and filmmaker Conscious Sheesh set the tone of the night as the evening's live poet and creative storyteller. Before the panel conversation even began, his performance signaled exactly what kind of night this would be — one where authenticity wasn't just encouraged, it was required. Weaving together storytelling, culture, spirituality, and lived experience, Conscious Sheesh delivered an immersive audience moment that primed the room for the vulnerability and candor that followed. It was a reminder that poetry isn't just an art form — it's a tool for truth-telling, which made his presence at a brand storytelling event feel less like entertainment and more like intention.

Acclaimed artist Danielle Bowman brought the night to life as the evening's live speed painter, creating stunning real-time artwork in front of the audience as the conversation unfolded around her. Her piece for the evening — a powerful live painting of Minister Louis Farrakhan — was a bold, culturally resonant choice that reflected the deeper themes of legacy, Black leadership, and community that ran throughout the entire event.

The Big Question: How Did You Leverage Your Story to Build Your Brand?

Ryan opened the conversation with a simple but powerful rapid-fire prompt: How have you used your story to level up your brand?

Rashan pointed to timing and need. Poetry Me Please was born out of COVID — the first showcase was originally planned for March 2020. When they finally launched in June 2021, the hunger for live community and artistic expression was undeniable. "Finding a way to have something consistent so poets could get their performances off — but also inviting people into a space where poetry is received in a different way — that was the key," he said.

Charles traced his entrepreneurial story back to a gap he spotted in New York's nightlife scene in 2016–2017: nobody was playing the kind of soulful, two-stepping R&B that he grew up with in Chicago. He built R&B House Party to fill that void — intentionally fusing church and club energy into something entirely its own. The brand grew, attracted major partnerships with Revolt and Amazon, expanded internationally, and eventually caught the attention of Blavity.

The origin of Oxtail Off was even more personal. During the pandemic, Charles was at home cooking oxtail — admittedly with barbecue sauce, much to his wife's horror. He started learning the "right" way from his Caribbean friends in New York, eventually convinced himself his recipe was unbeatable, and challenged everyone he knew. When 200 people showed up to what was supposed to be an intimate 150-person close-friends event, the Oxtail Off was born. The following year, he took it to LA with 2,000 attendees. A tour soon followed.

Kareem grounded his answer in service. Growing up in Far Rockaway, Queens, raised by a single mother, he learned early that food and presence were tools for community care. That instinct followed him into entrepreneurship. He shared a recent story: when a new Black-owned restaurant in Chicago was broken into, he didn't hesitate to show up with trays of food. Hours later, a customer who heard about the gesture spent $300 in his drive-thru. "They're telling the story for us," he said. "By just being present, showing up, and serving."

Key Conversation Moments

On Turning an Event Into a Real Brand

Ryan pressed both Rashan and Charles on the exact moment their projects crossed from "event" to "brand."

For Rashan, it was baked in from the beginning. He was getting his master's degree when the name came to him — "Poetry Me Please" — and he already knew it would have lowercase branding, a consistent visual identity, a specific room feel, and always open with a Black woman performer. "Everything about it is intentional down to the way that it looks," he said. He even released an ebook before the first showcase.

For Charles, the R&B Church moment crystallized it: at one Chicago party, he transitioned seamlessly from "Melodies from Heaven" into "Swag Surf" and the crowd completely lost their minds. "People left feeling like they experienced a moment," he said. "I left feeling more inspired." Then came the tax bill that forced him to get serious about business structure — enter CPA Mosiah, who reorganized his finances and helped him see what he was actually building. And later, when a lawyer called to say someone was infringing on the R&B House Party trademark and logo? "If someone's trying to steal the identity of R&B House Party," Charles said, "this is a legit brand now."

On What Made R&B House Party Acquisition-Worthy

Ryan asked one of the evening's sharpest questions: what made a party brand valuable enough for a media company to acquire?

Charles pointed to the combination of loyal community, diverse revenue streams, and — critically — margins. "Most people doing what you do, margins are about 25%," he said, paraphrasing his Blavity contact. "But yours are 40–50% on everything." The secret? Almost zero paid marketing (the community spread the word organically), and a deliberate focus on net profit over top-line growth. "I can't feed my family off growth. I gotta feed my family off net."

Kareem added the cost-side perspective: "From a cost standpoint, it was low. Charles had influencers coming out for the love. From a top line, different revenue streams maximized profit." Blavity saw it clearly: a lean, high-margin operation with a passionate community could be exponentially amplified with a media company's infrastructure behind it.

On the AutoTune Karaoke Origin Story — And Listening to Signs

Charles shared the origin of AutoTune Karaoke as a lesson in paying attention to divine nudges. He was hosting an All-Star Weekend event where artist Jeremiah had auto-tuned his mic during sound check. Charles got called onstage, grabbed the mic, and heard himself transformed. "It's something I've never sounded like in my life." A DJ in the crowd pulled him aside afterward: "You should make that into an event." It took eight or nine months to build the concept properly — the right sonic setup, the right branding, the right partnerships (Lucid, Crown Royal, Crown Skin — fresh off Shark Tank). The next show is happening the night after this taping, featuring Jadakiss.

"Take those moments seriously," Charles urged the crowd. "Your wife is telling you something. God is telling you something. Sincerely, I hope y'all felt that from my heart."

On Building a Brand While Keeping Your Day Job

Rashan still works full-time at Disney ESPN. Ryan asked him what he'd say to people in the audience doing the same — trying to build while employed.

Rashan shared that he reached out to Aaron Samuels, co-founder of Blavity, who told him something that reframed everything: "You're not even asking the right question. It's really not a question. Individuals like us just do." The real question isn't whether to quit — it's how to sustain what you're already doing. Rashan's answer: build a team. "Now my team is taking the inbound. My team is orchestrating things. I'm still behind the scenes, but now I have help. It's less of a toll on me individually."

On Taking Outside Capital

The audience Q&A surfaced one of the evening's most practical discussions: how to fund growth without compromising brand integrity.

Charles noted that R&B House Party was entirely self-financed until the Blavity acquisition — which taught him, in real time, what institutional partnership actually looks like. "When you bring other people into your home, it comes with its own set of challenges. You'll have to answer things you didn't have to before. But if scale is the goal, that is a great opportunity — not just monetarily, but for your mind."

Rashan raised $40K through his fraternity network for the Kings Theater / Live Nation event with Poetry Me Please — structured as a loan over 12 months. He also recently secured a loan through a CDFI (Community Development Financial Institution) — a resource he highlighted as essential for Black entrepreneurs who get turned away by traditional banks. "Capital should be accessible. Black people have been conditioned to romanticize struggling. Others are not playing the game the same way. The capital is out there — we just have to look for it."

Key Takeaways for the LEVELUP in NYC Community

1. Your Story Is Your Strategy

Every brand on the panel was built from lived experience — not a business plan written in a vacuum. The Oxtail Off came from a pandemic cooking experiment. Poetry Me Please came from paying $25 to perform and getting nothing in return. Chick-fil-A came from a kid in Far Rockaway who dreamed of opening a restaurant and lounge. Your personal story isn't just the origin — it's the competitive moat.

2. Build the Brand Before You Build the Buzz

Charles intentionally posted the first Oxtail Off only to his Close Friends list on Instagram. "I understood the importance of having a brand story and what that meant to the consumer." When 200 people showed up to a 150-person invite-only event, the organic demand validated everything. Don't rush to market — build the story first, then let the community carry it.

3. Content Is the New Currency

Rashan's model flips the traditional poetry show economics: instead of charging poets to perform, he gives them professional content — photos, video — to build their digital portfolios. "Content is king. Early." In an era where a performer's online presence is their résumé, giving them the tools to tell their own story creates loyalty and community that money can't buy.

4. Fire Yourself from Side Hustler — Become the CEO

Charles put it plainly: "You need to start thinking of yourself as CEO of your business." Creating an LLC isn't just legal housekeeping — it's a mental shift. The moment you stop treating what you're building as "just a little hobby" and start treating it as a business, everything around it changes: how you track finances, how you structure partnerships, how you present yourself to the world.

5. Get Your Financial House in Order Before You Need It

Multiple panelists pointed to organized finances as a non-negotiable. Charles's early tax nightmare — no business account, no structure, a bill he couldn't afford — was a turning point. Rashan cited clean P&Ls and organized invoices as what made his CDFI loan application "extremely clean." You don't need to be rich to get a loan. You need to be organized.

6. Balance Creativity with Accountability

The Charles and Kareem partnership is a blueprint. Charles has world-class creativity and fearlessness. Kareem brings structure, financial discipline, and reality checks. "I'm not minimizing the creativity," Kareem said, "but balancing with reality and what it would take — or the trade-offs." Every visionary needs someone who asks the hard questions. Find your Kareem.

7. Margins Matter More Than Revenue

The most overlooked business insight of the night came from Charles's acquisition story. Blavity wasn't just impressed by R&B House Party's community — they were impressed by 40–50% net margins. "I can't feed my family off gross. I gotta feed my family off net." Scale without profit is just noise. Know your numbers.

8. Community Is the Most Powerful Marketing Channel

Kareem didn't run an ad when he dropped food off at a struggling restaurant. But a customer who heard about it spent $300 in his drive-thru hours later. "They're telling the story for us." Every act of genuine community investment is a marketing event — one with no media buy behind it and unlimited organic reach.

9. Pay Attention to the Signs Around You

Charles's AutoTune Karaoke story — born from a spontaneous onstage moment with a borrowed mic — is a reminder that your next big idea might not announce itself loudly. A DJ in a crowd, a close friend encouraging you, a wife who sees what you can't: these moments are data. Treat them as such.

10. Do a SWOT Analysis (Seriously, Right Now)

Rashan offered this as his 30-day action item, and it's worth amplifying. A SWOT analysis — Strengths, Weaknesses, Opportunities, Threats — is the most honest document you can write about your brand. Rashan admitted he didn't do one until four years in. "I really wish I would have had this before I jumped out the gate." AI tools make it easier than ever. Block 90 minutes. Do it.

Final Thought

What made this LEVELUP in NYC event exceptional wasn't just the caliber of the guests — it was the honesty. Three founders who have faced real fear, real failure, and real growth showed up and gave the community something money can't buy: truth. The message across every story, every answer, every piece of advice was consistent: your story is enough. The work is in the telling.

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