This episode was 18 months in the making. Kevin Traynor, founder of eComm Live introduced me to his friends Tren’Ness and Rawle in a call Sept 2024. We were considering a dinner at NRF with a specific purview. We ran too close to the sun and it didn’t happen, but I stayed in touch with Tren’ness. There was something about her energy. Then you do some research, watch some videos and listen. Kev has made a career in community building and it is largely about connecting people who should be connected, I like to think, I share this value. 2025 proved difficult for many people in a variety of ways. The ghost of 2025 lingers like a dark shadow still, but history taught us to persevere, sometimes to look for the bright spot.
Full episode here - Struggle Bus S 2 Ep 10
We tried twice to do this pod, remotely, both times technology let us down. So it seemed serendipitous to go to Harlem during NRF 2026 to sit down in person and talk. A young school friend once introduced ne to the Celestine Prophecy. The idea that everyone we meet has amessage, it is up to us to decide how to use it. Of course I was a pudgy, buck toothed 14 year old who had given her a Valentines Card, unabashed, she was trying to let me down easy. I went back to the same girl a few years later with another attempt quoting Yeats - “Thread softly, for you thread on my dreams.” The lady was not for turning. But the book was a blessing.
“We must assume every event has significance and contains a message that pertains to our questions...this especially applies to what we used to call bad things...the challenge is to find the silver lining in every event, no matter how negative.”
― James Redfield, The Celestine Prophecy
While forty thousand people were “stomping the floors” of the Javits Center, navigating the neon-lit aisles of AI-powered checkouts and robotic logistics, I was sitting in a cab heading Uptown. I was also holding a mobile podcast device, never having used it before in the hope that I got the setup right and we would be able to hear our discussion in hindsight. Anxiety and hope met and decided to roll the dice.
On Monday, the 12th of January, I chose a different kind of digital transformation. I was hear to understand how brands are born and legacy endures.
I was finally going to meet Tren’ness Woods-Black.
The Queen of Soul Food’s Fortress
To understand Tren’ness, you have to understand the ground she stands on. We met for lunch and then proceeded to Sylvia’s Restaurant, located at the intersection of what is now Malcolm X Boulevard and W 126th St (just a block up from Martin Luther King Jr. Blvd). Sadly a week out from MLLK Day, it feels like much of his wisdom still has not yet been evenly distributed.
Sylvia’s isn’t just a business; it’s a monument. Founded in 1962 by the “Queen of Soul Food,” Sylvia Woods, it began as a humble 15-stool luncheonette. Over sixty years, it expanded into a city block-sized institution that has fed everyone from neighborhood locals to Barack Obama, Bill Clinton, and Denzel Washington.
But as I walked through the doors, I didn’t see a “celebrity haunt.” I saw a home. Everyone I met hugged me without exception. A hug is a handshake it seems. This is ok, it is my wife’s default too. It is her Superpower.
The restaurant was technically closed for a staff holiday party, but the air was thick with the scent of heritage and hospitality. There were workmen prepping the floors, their children running between their legs. There was an aura of history without pretense.
Being Irish, I felt a strange, immediate sense of recognition. There is a specific frequency of “home” that we recognize a place where the weight lifts off your shoulders the moment you cross the threshold. It’s the feeling of a place where, historically, if you had no money, you still got fed, and you left with your dignity intact. And something nourishing in your belly and your soul in equal portions.
The Funding Gap: When Values Become “Add-ons”
Tren’ness has spent her life stewarding this legacy. She is a woman who has raised $1.4 million in sponsorship for community block parties; she is a powerhouse of empathy. Yet, we sat down to discuss a harsh reality. Her sponsors previously include Doordash, Thrillist and more.
She has been continuing to trying to secure funding for the digital transformation of hospitality businesses in Harlem—, he kind of “upgrading” that the folks at NRF take for granted. But the climate has shifted.
“DEI (Diversity, Equity, and Inclusion) was doomed to fail the moment it was treated like sustainability as an elective add-on rather than a core value.” This is my sentiment.
As brands retreat from DEI commitments in the current political cycle, the funding has dried up. For Tren’ness and her family, the challenges aren’t just professional; they are visceral. The business still thrives but this wider community needs some light shining on it too. From all walks of life. Hearing about the conversations a Black family must have with their children in today’s climate was a sobering reality check. It’s a struggle we don’t have to face in Ireland, yet as a nation of underdogs, it’s one we can, and must, empathize with.
A Tale of Two New Yorks
My afternoon was a study in extremes.
1:00 PM: Absorbing the generational weight and loving power of Sylvia’s in Harlem.
5:00 PM: Watching a “Retail Media Celebrity Deathmatch” at the Gotham Comedy Club.
8:00 PM: An awards ceremony in the gilded luxury of Midtown Manhattan.
The contrast was jarring. While the industry discusses “customer centricity,” Sylvia’s has been practicing it as a survival mechanism for 60 years. Their “brand value” isn’t a slide in a deck; it’s the fact that they are a refuge.åç
We often choose not to hear the stories of the sectors that need us most. We focus on the high-margin, high-tech players and forget the “homely” retail that forms the bedrock of our communities.
The Power of Love as a Business Model
I didn’t take a single photo that afternoon. It felt too personal, too sacred to view through a lens.
What I learned from Tren’ness is that in a world where power is often wielded for its own sake, her power is love, compassion, and empathy. She wants the next generation to have it better than she did, and she acts with a humility that would put most CEOs to shame.
As I wrap up Season 2 of The Struggle Bus, this episode stands as a testament to what retail should be. It’s not about the “stomp” of the conference floor; it’s about the “sigh of relief” when someone enters your space.
We need to bring these businesses to the same level as the rest of the industry, not as a charity case, but because their core values are more authentic than any “purpose-driven” marketing campaign I saw in Midtown.
Sylvia’s is a reminder: Retail is at its best when it feels like coming home.
