When you walk into an event like Crain’s Crossroads, you feel it. That hum of energy, the buzz of possibility. It’s not just a room full of smart people—it’s a room full of people daring to ask, what’s next?

After the event, I sat down with Jordan Person, Managing Partner at Town Hall, our sister agency specializing in higher education and mission-based brands, and Leslie Barrett, Managing Director at Situation, to unpack it all. What struck me wasn’t just the abundance of ideas—but the big question: how do we keep this conversation alive? How do we take everything we’re dreaming up for urban centers—whether in New York, San Francisco, or Columbus—and frame it in ways that inspire action, curiosity, and maybe even awe?

Spoiler alert: I turned to AI.

Now, I know what you’re thinking. Another podcast? Bear with me. What if you could listen to a podcast that didn’t just summarize our conversation but reimagined it? Using AI, I turned our chat into a 12-minute episode, capturing the essence of what we talked about—Jordan’s passion for green tech, Leslie’s community-driven vision, and my musings on, well, the potential of AI to do stuff like this.

The kicker? It feels like a Spotify Wrapped for conversations. (Side note: this year, Spotify Wrapped used similar technology to create podcasts that analyzed users’ listening habits—sort of like a post-game breakdown for your music taste). The AI didn’t just regurgitate words; it teased out themes, added structure, and made our thoughts feel cohesive in ways I wasn’t expecting. You can listen to it right here:

Of course, being New Yorkers, we couldn’t stop at just talking. The city isn’t just built on ideas—it’s built on what those ideas look like. That got me thinking: what would Crain’s Crossroads have looked like if it mirrored our vision for the future of New York?

Using AI, I created an image—a kind of visual manifesto. Imagine the New York skyline with a few twists. There’s Jordan’s dream of urban greenhouses perched on skyscrapers, Leslie’s community-first neighborhoods with spaces designed for human connection, and even an AI-powered subway system rethinking how we navigate the city.

Here’s what the event might have looked like through the lens of our conversation:

It’s not just an image. It’s a conversation starter, a glimpse in a very exciting future (or maybe just a version of New York that sort of looks like Singapore).

Then we got to the really fun part: What else can we do with AI? Sure, it can summarize, visualize, and even chat—but what about something more fun? So, we asked our chatbot to flex its creative muscles:

‘Twas the night before Christmas, and Crain’s Crossroads buzzed,

With plans to save Santa—it caused quite a fuss.

His sleigh was in pieces, his reindeer on strike,

But Damian, Leslie, and Jordan said, “Alright!”

With AI elves coding and drones taking flight,

They mapped every borough through the cold, starry night.

From Crossroads to rooftops, gifts spread through the city,

“Merry Christmas, New York!”—their teamwork was witty!

Cities, and maybe I’m biased but especially ones like New York, thrive on reinvention. Every subway line, every brownstone, every bodega is a testament to the city’s relentless push forward. At Crain’s Crossroads, we asked, what’s next? But asking the question is just the first step. The real magic happens when we find new ways to explore the answers—and bring more people into the conversation.

So call me crazy, but it’s my belief that AI didn’t replace our creativity; it amplified it. It framed our ideas in ways we hadn’t imagined and invited others to dream alongside us.

Here’s my challenge to you: listen to the podcast. Look at the image. Test the holiday story out on your kids over the break. Then ask yourself: what’s next for us?

Because if there’s one thing we learned at Crain’s Crossroads, it’s that the future of this city isn’t written yet. And that’s a good thing.

Let’s write it together.