Chrissie Hanson has built her career at the intersection of rigor and curiosity -- shaped early by growing up in Hong Kong, navigating multiple cultures, and learning how identity, discipline, and brands signal meaning long before she had language for any of it.

Chrissie joins the podcast to talk about how those formative experiences influenced her leadership style, why discipline and follow-through matter more as careers progress, and how movement, routine, and self-awareness help her stay clear-headed in moments of pressure. She shares how exercise unlocks creativity, why agencies remain a uniquely energizing place to build a career, and what it takes to sustain momentum over decades in a demanding industry.

Jordan and Chrissie also explore what makes agency life uniquely demanding and addictive, why technical fluency is essential for modern CEOs, and the responsibility leaders have to make others feel seen. Along the way, Chrissie reflects on mentors who helped her see her own strengths more clearly, the importance of making others feel seen, and why leadership is as much about generosity as it is about decision-making. They also talk about how winning agency of the year awards have much in common with restraunts attaining a coveted Michelin star.

Tim Castelli has built a career by repeatedly stepping away from what was comfortable in order to lean into what was coming next. From print to digital, from static to dynamic, and from content to commerce, he never sits still.

Tim joins the podcast to talk about growing up as a studious kid in Weirton, West Virginia, what studying psychology at Duke taught him about sales and leadership, and why he believes the most important career moves often require going sideways or backwards in the short term. He reflects on his early years in print at Ziff Davis and Rolling Stone, his decision to leave publishing to get his “MBA in digital” at Google, and what it has been like learning entirely new languages like search, digital audio and retail media.

Jordan and Tim also discuss his appreciation for "things that are true, but hard to understand," his mom's ultimatum back when he was still living at home, and how he had Pittsburgh Steelers royalty gathered at his kitchen table as a kid. He also goes on the record (sort of) by naming the best agency relationship leader he has ever worked with.

Katherine Naylor Pullman has had a big few years. She got married, became a mom, left her full-time job, and turned a side project into a fast-growing national community for women. As the founder and CEO of Our Third Place, she’s building something that sits somewhere between networking, friendship, and the modern search for belonging — and she’s doing it in a way that feels both deeply personal and surprisingly scalable.

In this episode, Katherine talks about the identity shift that comes with new life chapters, the moment she realized all her job changes in her twenties were pointing toward entrepreneurship, and why authentic relationships - the kind that help you through both career decisions and pregnancy - are at the heart of her company.

Jordan and Katherine get into what members are talking about at her dinners, how she's able to walk into any room, and why the best networking doesn’t feel like networking at all. It’s a conversation about confidence, community, and the power of showing up exactly as yourself (and letting that be more than enough).