YALE BRESLIN ISN’T TRYING TO FIX MEN. HE JUST WANTS TO HAVE BETTER CONVERSATIONS WITH THEM.

Created and hosted by New York-based creative Yale Breslin, the series strips away the press-tour version of a guest and gets to the person underneath. The questions aren’t designed to go viral—they’re designed to make someone forget they’re being interviewed in the first place.

It’s a surprisingly simple idea, and maybe that’s why it works.

Yale Breslin photographed by Justin Wolf for IMAGINE. New York, 2026.

Over the course of nearly 40 episodes, Breslin has sat down with everyone from Ian Schrager, Eric Ripert, Ryan Serhant, Jake Shane, Chris Appleton, Eli Zabar, Ronnen Harary, Jeremiah Brent, Malcolm Todd, Nicolas Jammet, Joey Gonzalez, and Ryan and Adam Goldston, the founders of APL Sneakers. On paper they don’t have much in common. In conversation, they do.

They’ve all built something. They’ve all failed at something. They’ve all questioned themselves more than you’d probably expect.

That’s the part Breslin is interested in.

“The internet already knows what someone does,” he says, “I’m much more interested in who they are once you get past all of that.“

Maybe that’s why the conversations feel different. Guests aren’t asked to relive the biggest deal they ever closed or the movie they just wrapped. Instead, they’re talking about confidence, relationships, identity, grief, ambition, imposter syndrome, failure and the strange pressure that comes with building a life that looks successful from the outside.

Yale Breslin photographed by Justin Wolf for IMAGINE. New York, 2026.

Perhaps the most surprising part is that OFFICE OF is almost entirely a one-man operation. Breslin books the guests, produces the episodes, oversees the edits, builds the creative, manages the partnerships, writes the social copy and somehow still manages to make it all look effortless.

“It definitely isn’t,” he laughs. “I’ve just gotten good at making the chaos look organised.“

With Season Two arriving this fall—the show continues to evolve. The episodes are getting bigger, the clips are getting shorter and the conversations are only getting deeper.

Because at the end of the day, Breslin isn’t trying to reinvent the interview.

He’s just trying to have the kind of conversations most people wish happened a little more often.

For someone discovering OFFICE OF for the first time, how would you describe it?

I usually tell people it’s a podcast about men, but that’s only part of it. It’s really a show about people who have built something and what it took to get there. I’m far less interested in someone’s résumé than I am in everything that happened before it. We already know what these people do—that’s why they’re sitting in the chair. What I want to know is what shaped them, what they struggle with, what motivates them, and what nobody ever asks them about.

What made you want to start it?

I’ve spent most of my career telling other people’s stories through social media and content. Somewhere along the way I realized I wanted to have these conversations myself.

I also felt like there was room for something different. Everyone has become their own publicist, and every interview starts to sound the same after a while. I wanted to create a space where someone could forget they were promoting something and just talk. Ironically, that’s usually when the most interesting stories come out.

Your guests range from chefs and founders to athletes, designers, and musicians. What’s the common thread?

Curiosity.

Every person who’s come on the show has built something they’re proud of, but they’ve also sacrificed something to get there. Success is expensive. It usually costs time, relationships, confidence, peace of mind—sometimes all of the above.

I’m fascinated by that trade-off because we spend so much time celebrating the outcome that we rarely talk about the process.

Has anything surprised you since launching the show?

Honestly, how similar everyone is.

You sit down with someone who’s built a billion-dollar company or won Olympic medals and you expect them to have all the answers. Then they start talking and you realize they’re asking themselves a lot of the same questions everyone else is.

The job titles change. The doubts don’t.

Your interviews feel more like conversations than interviews. Is that intentional?

Completely.

I don’t walk in trying to get through a list of questions. If I did, I’d probably miss the best part of the conversation. I’m listening more than I’m thinking about what’s next, and I think guests feel that.

The moments people remember are almost never the ones I planned.

Yale Breslin photographed by Justin Wolf for IMAGINE. New York, 2026.

You built OFFICE OF yourself. Was that always the plan?

Not really. It was more necessity than strategy.

There wasn’t a big team behind this. I booked the guests, found the studio, figured out production, learned the edit, built the website, created the social strategy, wrote the captions, pitched the partnerships—you name it.

Looking back, I’m glad it happened that way because every part of the show feels personal. Every decision has been intentional, even if I was figuring it out in real time.

Has the podcast changed you?

Without question.

It’s made me a better listener. It’s also made me care a lot less about appearances and a lot more about substance. The older I get, the more I’m drawn to people who are genuinely curious, kind, and self-aware. Those qualities stay with you long after someone’s job title doesn’t.

Why record at Rockefeller Center?

Partly because it’s iconic, and partly because I love the contrast. You’re in one of the busiest places in New York, but once those studio doors close, it becomes incredibly intimate.

Also, it’s a pretty easy sell when you’re inviting guests.

What can people expect from Season Two?

More of what worked, just better.

We’re putting a much bigger emphasis on short-form because that’s how people discover conversations now. A 45-second clip might be what introduces someone to the show, but I still want the full conversation to be worth staying for.

The format is evolving, but the mission really hasn’t changed.

Who’s still on your dream guest list?

Tom Ford. Marc Newson. Rick Rubin. David Beckham. George Clooney. Lorne Michaels. Johnny Knoxville. Anderson Cooper.

Honestly, I’m less interested in someone’s level of fame than I am in whether they have perspective. If you’ve lived an interesting life and you’re willing to be honest about it, that’s usually enough for me.

Yale Breslin photographed by Justin Wolf for IMAGINE. New York, 2026.

After nearly 40 conversations with some of the most accomplished people in the world, what have you learned about yourself?

Probably that I’m a much better listener than I used to be.

When I first started the podcast, I was so focused on asking the right question. Now I’ve realized the best moments usually happen after the answer. Someone says something unexpected, you stay curious, ask one more question, and suddenly you’re having a conversation neither of you saw coming.

I’ve also realized I’m far less interested in success than I thought I was. Success might be what gets someone into the chair, but it rarely makes them interesting. What makes someone interesting is what they’ve overcome, what they’ve sacrificed, what they’re still wrestling with, and whether they’re willing to be honest about it.

The other thing I’ve learned is that nobody ever really arrives.

You sit across from people who’ve built billion-dollar companies, earned Michelin stars, sold out arenas, or completely changed an industry, and you realize they’re asking themselves many of the same questions the rest of us are. They still second-guess themselves. They still wonder if they’re doing enough. They still want to be understood.

I find that incredibly comforting.

It’s made me a little more patient with myself and a lot less obsessed with the idea that there’s some finish line where everything suddenly makes sense. More than anything, it’s reminded me that we’re all works in progress—and that’s probably the most interesting part.