From the Ring to the Digital Arena: Managing Legends in the New Era of Marketing

When the world shut down in 2020, so did the events industry. What was once a thriving space of live activations, sponsorships, and in-person engagement was suddenly gone. For those of us who built careers in experiential marketing, it was a wake-up call.

I had spent years in event production and brand activations, bringing people together in real life—feeling the energy of a crowd, the anticipation before a major moment, the chaos behind the curtain. But when the pandemic hit, everything flipped overnight. Events disappeared, and brands scrambled to adapt. We weren’t just forced to pivot—we had to reinvent.

That’s when I made the move to Los Angeles to work with Pillar Marketing, a small but powerful team with a big responsibility: shaping the digital brands of some of the most iconic figures in sports and entertainment.


Working with Legends: Tyson, Rodman, Flair, Peña

Managing the personal brands of Mike Tyson, Dennis Rodman, Ric Flair, and Julianna Peña wasn’t just about keeping their names in the conversation—it was about evolving them. These weren’t just athletes; they were legends, each with a story, a legacy, and a fanbase that spanned decades.

The challenge? Taking their presence beyond nostalgia and into relevance in the digital-first world.

My role was all-encompassing:
✅ Social Media Management – Running their platforms, shaping their voice, and keeping them connected to millions of fans.
✅ Website Development & Content Strategy – Turning their digital presence into a powerhouse of engagement and commerce.
✅ Merchandising – Creating and launching products that resonated with both die-hard fans and new audiences.
✅ Brand Collaborations & Endorsements – Aligning them with partners that made sense for their legacy and future.

We weren’t just posting content; we were crafting narratives. Every post, every campaign, every brand deal had to match their persona—because when you’re working with figures this legendary, authenticity is everything.


From the Stage to the Screen: The Digital Pivot

Pre-pandemic, these legends were used to packed arenas, meet-and-greets, and sold-out speaking engagements. Now? The game had changed. We had to bring the experience to the fans, not the other way around.

  • Tyson’s cannabis empire was booming, and digital content became a crucial piece of his branding.
  • Rodman remained a cultural enigma, with a resurgence in streetwear, NFTs, and partnerships with modern brands.
  • Ric Flair’s “WOOOOO!” became bigger than ever, and we capitalized on digital storytelling to keep his legacy alive.
  • Julianna Peña went from fighter to champion, and we made sure every step of her journey was documented and amplified.

Live events weren’t happening, but their brands couldn’t afford to stand still. We used content, storytelling, and digital-first strategy to keep them top of mind—and, more importantly, top of culture.


Lessons from Managing Icons

Working with some of the most polarizing, influential, and larger-than-life figures in sports and entertainment came with its lessons:

🔥 Your brand is bigger than any one moment. It’s about consistency, legacy, and evolution.

🚀 Social media isn’t just a tool—it’s the stage. If you don’t control the narrative, someone else will.

💡 Branding is about storytelling, not just selling. Fans don’t just buy merch; they buy into a persona, a movement, a legacy.

⚡ Adaptability is everything. What works today might be irrelevant tomorrow. The greats don’t get stuck in the past—they rewrite the future.


The Experience of a Lifetime

Few experiences compare to helping craft the modern-day identities of some of the most electrifying, controversial, and unforgettable figures in sports history. Managing their brands wasn’t just a job—it was a front-row seat to understanding how icons stay iconic.

From fighting through the collapse of an industry to helping legends evolve in a digital-first world, it was a ride I’ll never forget.

And the best part? The work never stops. Because legends don’t retire—they adapt.