Ramsey McGrory was a Montana kid who drove his dad's two-toned '57 Ford truck by sliding in through the passenger side door. He joined the Army out of high school, served in the Gulf War, worked a presidential campaign, and stumbled into the early internet through a modem at NationsBank — all by his early 30s. That restless, excitement-junkie energy carried him straight into the plumbing of digital advertising, where he has spent the next three decades helping build the infrastructure the industry runs on.

Ramsey joins the podcast to talk about what it was like to be inside DoubleClick in its rocket-ship years, how he followed Mike Walrath to Right Media in 2004 to help invent dynamic CPM pricing and launch one of the first open ad exchanges, and what he learned from a decade-plus at Mediaocean alongside Bill Wise, where the company became the system of record for roughly $200 billion in annual ad spend. He reflects on being inside two of the most consequential acquisitions in ad tech history — Right Media to Yahoo and MediaOcean to private equity — and shares a hard-won philosophy: the culture and vision of a founding team matters as much as any financial model, and when those aren't honored post-acquisition, the talent walks and the mission dissolves. He also talks openly about why he's stepping back from his President role at Mediaocean now — not to slow down, but to go all-in on AI at a moment he believes is more transformative than search, social, and programmatic combined.

Ramsey and Jordan also get into the nature of building things people depend on without knowing they depend on them, what it means to be an infrastructure person in an industry full of brand and creative people, and why Ramsey believes the smartest bet you can make is on yourself.

Brian Matthews built a career at some of the most iconic media brands in the world -- CNN, the BBC, and NBC -- where he spent over a decade as a digital evangelist inside traditional television organizations, convincing linear sales teams that the future wasn't a threat to their business but an extension of it. In 2014, he joined the NFL, which turned out to be the dream job he might not have dared to write down on paper.

Brian joins the podcast to talk about what it was like to be a digital guy inside legacy media companies at the exact moment the industry was beginning to shift, how he navigated that internal sell, and what drew him to the NFL. He shares the league's remarkable transformation from a four-and-a-half-month sport into a year-round cultural juggernaut, what it's really like to work a Super Bowl when you're there in a professional capacity and what the recent sale of NFL Network to ESPN means for the league and for him personally.

Brian and Jordan also dig into the future of television, how streaming and linear are likely to coexist, why live sports remain the most powerful force in the medium (including how the league is often a trojan horse in getting audiences to sign up to services), and they talk about their shared Giants grief, because...therapy.

Atit Shah has spent nearly three decades at one agency -- not because he stood still, but because the agency always let him keep moving forward. What started as a Monster.com resume posting and a junior account executive role, has turned into one of the most quietly remarkable creative careers in our business.

Atit joins the podcast to talk about what it felt like to be "voluntold" by a senior colleague that he was in the wrong department and how a brutal portfolio class at SVA set him on the path to becoming a copywriter...and eventually the Chief Creative Officer at Digitas. He reflects on what it means to be a "spotter" of elusive signals, his belief that "If you can't say an idea in a sentence, it's probably not strong enough," how the American Express account became his creative education, and why he believes modern marketing problems are inherently creative puzzles regardless of your job title.

Jordan and Atit revisit the first time either of them ever presented to a CMO - for both, it was in a wood-paneled room on the 50th floor of a shiny corporate office in lower Manhattan - and what that moment of reverence taught them about generosity, coalition-building, and the nobility of the work. Atit also makes the case that the old-school CCO archetype of legs on the desk - and ripping ideas off the board - is dead (and good riddance!).

Kristine Segrist got her start writing meta tags for SEO at a small St. Louis agency (probably not exactly the Don Draper copywriter role one might envision), but that humble beginning opened doors she couldn't have imagined. From there, she spent over a decade building digital practices at WPP, before heading to Meta for nearly seven years where she rose through roles spanning media, product marketing, and brand.

Kristine joins the podcast to talk about why agencies are such a powerful training ground for operating with ambiguity, what working at a product-first company like Meta taught her about what marketing can and can't fix, the power of "listening until your ears bleed," and what drew her to Canva's mission of putting the power of creation into everyone's hands.

Kristine and Jordan also explore whether AI will homogenize creativity or make the best creators even better -- and Kristine makes a case that it's both. They dig into how Canva uses Canva to run its own marketing, and they talk about approaches for having healthy conflict at work.

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).