In this episode of I Don’t Know Where This Conversation Is Going to Go, I sit down with my friend and colleague Greg Ippolito — someone I’ve known for so many years that our conversations tend to zig, zag, loop back, and somehow land exactly where they’re supposed to.

We talk about a lot — connection, marketing, music, creativity — but it all comes back to one simple truth: people. How we show up for each other. How we communicate. How we build trust. And how, despite all the digital noise we navigate every day, the most meaningful moments still happen one human at a time.

Greg and I riff on where marketing is headed. We also get into why genuine, personal connection matters more than ever — not as a tactic, but as a way of being.

Some of my favorite parts of our conversation are about music. We swap stories about rediscovering it during the pandemic, the strange comfort of gathering around a piano, and the science behind why certain songs make us feel seen, understood, or simply less alone. We even wander into the nostalgia of vinyl. You'll see.

We also talk business. The messy blend of sales and marketing. The power of referrals. The magic that happens when you experiment with content instead of overthinking it. And the humble, often invisible ways people help shape our lives without us realizing it until years later.

It’s a thoughtful conversation, and it’s a reminder that connection — real connection — is still at the heart of good work and a good life.

Takeaways:

• Real connection always beats slick, surface-level marketing.
• Revisiting old passions (like music) can bring people closer.
• Creativity thrives when you’re willing to experiment and not take yourself too seriously.
• Many of the moments that shape us don’t look significant until we look back.

Links Mentioned:

• IMA: ima314.com
• Michael Piperno: michaelpiperno.com