Kevin Wassong has spent his career chasing what’s next — often before the rest of the industry was even ready for it. From television to entertainment to digital and now AI, he has consistently built at the edge of change.

Kevin joins the podcast to talk about working on The Golden Girls during its final season (editor's note: best show ever), how early exposure to storytelling and technology shaped his instincts, and why he has always been drawn to building new things. He reflects on his time at Radical Media and J. Walter Thompson, the risks of building things too early, and the difference between the "bleeding edge" and the "leading edge."

Jordan and Kevin also discuss timing, passion and why some problems are worth coming back to again and again. They close with a personal conversation about purpose, Sandy Hook Promise, and the belief that passion is the one thing you can’t buy.

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).

Bob Lord has built his career helping companies navigate moments of profound change — from early automation on factory floors to digital transformation across media, technology, and marketing.

Bob joins the podcast to talk about how past technology shifts reshaped entire industries, why removing mundane work is often what unlocks the most human value and why today’s AI moment feels familiar. He shares lessons from leading transformations at Razorfish, AOL, and IBM, and explains what it takes to drive change inside organizations at massive scale.

Jordan and Bob discuss his family's tradition of welcoming in new members with a triathalon, why an agency client once told him she'd fire him if he opened a local office near their headquarters, how transformation only happens when "ideas get into the machine" and leaders "give hope for the future while painting reality," and what drew him back into the industry and his current role as President of Horizon Media.

Mike Romoff has built a career at the crossroads of community, technology, and commercial leadership — from early roles in ad tech and publishing to senior positions at LinkedIn and now Reddit, where he serves as Chief Revenue Officer. Known for his eclectic style and systems-driven mind, Mike has made a career out of bringing order to complexity.

Mike joins the podcast to talk about his spirituality, a recent meeting with the Dalai Lama, and how raising a neurodiverse child reshaped his understanding of success, compassion and purpose. He and Jordan discuss the power of Reddit, why authenticity thrives in anonymity, and how the platform sits at the center of today’s AI revolution. They also discuss individuality in leadership and how to stay grounded: in work, in community, and in the moments that matter most.

Janet Balis has spent her career at the intersection of media, marketing, and transformation — from Time Warner and AOL to Martha Stewart Living, EY, and now BCG. A connector of people and ideas, she has helped shape how companies adapt to disruption, and how leaders think about influence, innovation, and purpose.

Janet joins the podcast to talk about how AI mirrors the early days of digital, and why asking the right questions is more important than having the answers. She also opens up about friendship, resilience, and her long-running commitment to Cycle for Survival, the charity founded by her late friend Jennifer Goodman Linn.

Jordan and Janet discuss what separates great leaders from merely good ones, the joy of constant reinvention, and how to stay connected — to ideas, to people, and to yourself — no matter what comes next.

Seb Tomich has helped redefine how legacy media evolves for the digital era. After early hustles selling Patagonia jackets in Boulder and sunglasses in New York, he found his footing at Forbes under the mentorship of Meredith Kopit Levien — who would later bring him to The New York Times, where he spent more than a decade driving digital transformation, building T Brand Studio, and shaping the company’s pivot from print to digital.

Now as Chief Commercial Officer of The Athletic, Seb is leading the next evolution of sports media. He joins Jordan to talk about the lessons he has learned from Meredith, the long game of the Sulzberger family, and why brand endurance may be the ultimate advantage in a fleeting digital world. Seb also shares his unlikely blessing from the Dalai Lama, living in an RV in Jersey City, his transition into fatherhood, and the joy of building something that truly lasts.

Jacki Kelley’s career spans the full breadth of modern media — from the circulation department at USA Today to leadership roles at Yahoo, Martha Stewart, Bloomberg, Dentsu, and now Interpublic Group. Raised on a Colorado ranch, she learned early the values of discipline, empathy, and hard work that would define her approach to business and life.

Jacki joins the podcast to talk about what it means to “become a beginner again,” the mentors who shaped her path, and her belief that “the quality of our relationships remains the most valued measure of our success.” She shares lessons from leaders like Wenda Harris-Millard, Martha Stewart, and Michael Bloomberg, and explains the “balcony to basement” leadership philosophy that guides how she manages both big vision and small details. Jacki also opens up about her family’s experience fostering more than 25 children — and how that journey has deepened her sense of purpose and perspective.

Rob Norman has spent decades helping to define the modern media industry. Starting as a media assistant in London, he rose to lead GroupM North America and later, as it's Global Chief Digital Officer, he traveled the world helping clients drive innovation during the rise of social, mobile and auction-based media. All along the way, he has helped shape the careers of many of today's industry leaders.

Rob joins the podcast to talk about the genesis of holding companies and the difference between power and influence. He and Jordan discuss Rob's approach to mentoring, the satisfaction of being useful, his near-perfect New York Times Spelling Bee streak, and how a trip to Shea Stadium in 1986 turned him into a lifelong (and long-suffering) Mets fan. Jordan also asks Rob a burning question regarding his own career that he's been wondering about for amost 10 years.