John Hayes is the former Chief Marketing Officer of American Express, a longtime leader at advertising agencies, and a recent inductee into the Advertising Hall of Fame.

John joins the podcast to talk about the lessons he learned from Amex CEO Ken Chenault, how Walt Disney's dissatisfaction that his animated films were trapped on screen shaped his own belief in experiential marketing, the near-disaster behind an important card launch early in his CMO tenure, and why he believes only two things actually predict a career that lasts: curiosity and persistence.

John and Jordan also discuss John’s early dream of becoming a radio DJ, the cross-country drive to Los Angeles right after college that led him into advertising instead, and what he’s up to these days (spoiler: he’s a little bit marketing, a little bit rock n’ roll).

Amanda Richman grew up on a family farm in Tower City, North Dakota (population 360) with her eye fixed on New York City from the time she was old enough to sense it through magazines, films, and family road trips. In the years since, she has become a big player on the advertising world's biggest stages.

Amanda joins the podcast to talk about leading Mindshare's transformation from conventional media agency to agile marketing partner, what it felt like to make two jumps at once when she crossed over from agencies to Microsoft, and why she believes the most important thing a leader can do is find their voice early and use it -- without waiting for the title to grant permission. She reflects on the Discover Card pitch that helped define what Mindshare stood for, the "low hum of anxiety" that ran underneath her year between full-time roles, and how hundreds of coffee conversations in late 2023 pointed her squarely toward the center of the AI wave.

Jordan and Amanda also get into the moment many years ago when Satya Nadella told a room full of advertisers that Microsoft might be getting out of the advertising business, and what it means that she's now one of the people charged with building it up even higher.

Bryan Wiener has spent his career getting into new areas of marketing early and then building organizations around what he saw coming: search, social, e-commerce analytics. Now, with 37Arc, he's doing it again. This time he's squarely in the middle of the AI transformation reshaping marketing from the inside out.

Bryan joins the podcast to talk about why he believes AI represents a fundamentally different era than anything that came before it: something closer in scale to the industrial revolution, compressed into five years. He breaks down why most enterprise AI adoption is failing, and why the gap between companies using AI and companies actually scaling it is enormous and likely to stay that way.

Jordan and Bryan also get into Bryan's vibe-coding a live music aggregator website for his Boca Raton friend group while watching the NCAA tournament, the chaos-is-a-ladder philosophy he's carried from Game of Thrones throughout his career, and why he thinks young people bemoaning AI disruption are making a self-fulfilling mistake. Bryan also makes the case — bluntly — that most layoffs being blamed on AI are actually just layoffs.

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).

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.

Abbey Klaassen is the Global Brand President at Dentsu Creative, where she leads thousands of creative professionals around the world. Earlier in her career, she was at Advertising Age, where she rose from reporter to editor and associate publisher, before making the leap to the agency side at 360i.

Abbey joins the podcast to talk about the risks of leaving journalism for advertising, what she learned from running new business pitches, which jobs she thinks she was not ready for when she got them, and why she believes AI can expand creativity as opposed to diminishing it. She and Jordan also discuss Abbey's Midwestern roots, her balance of right and left brain thinking, the value of being a "utility player," and the power of being a part of professional groups (Go French Bulldogs!).

Penry Price is a media and technology leader whose career has spanned publishing, ad tech, and some of the world’s most influential platforms. He’s held leadership roles at Rolling Stone, Us Weekly, Google, and LinkedIn, where he served as VP of Marketing Solutions for nearly a decade.

Penry joins the podcast to talk about growing up in a Mad Men household, his family’s 800-person reunion, and what it was like to help Google and LinkedIn build multi-billion dollar ad businesses.

He and Jordan discuss the influences of Tim Armstrong, Jeff Weiner and Satya Nadella, the question that a successful sales leader might have working at a major platform ("Is it me, or the brand?"), the rules he made for himself as the creator of his LinkedIn walk-and-talk videos, and the grand gesture he made to people in his life on the occasion of his 50th birthday.

Sarah Personette is a media industry leader who has worked at some of the most well known media brands over time: Facebook, Twitter, Starcom, Universal McCann and Refinery29.

She is now the CEO at Puck, the media company covering the intersecting worlds of Silicon Valley, Hollywood, Washington and Wall Street.

Sarah joins the podcast to talk about her bold career ambitions growing up, how agencies provide the opportunity to emerging talent to lead teams at a young age, and what UM saw in her to make her their U.S. President when she was just 33 years old. She and Jordan discuss the difference between working at Facebook and Twitter, her background as an opera singer, and why being known for both toughness and kindness is important to her.