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 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 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 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 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 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 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.

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 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 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 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.

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 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 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 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 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.

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.

Lee joins the podcast to talk about growing up in Kentucky, the experience of being the youngest child, the oldest child, and an only child — all in the space of one lifetime (it's true!), and his need to make a career pivot at just 23 years old.

He shares his Dad's philosophy on 'working the hardest, even if you're not the smartest,' the aggressiveness it took to land accounts early in his career and how he is inherently motivated by risk. Lee and Jordan discuss Lee's ability to merchandise a business through experiences and aesthetics, and the power - and comfort - of having a strong network in business.

A note to listeners, this conversation with Lee will be the the last episode until just after Labor Day. We'll be back then with fresh sauce."

Gurman joins the podcast to talk about why he believes in operating with a long-term mindset, the reason he never took venture capital, the philosophy of "sell or be sold" that helps him and Lee make big decisions, and why he has no desire to ever have "an exit."

He and Jordan discuss how to make big bets in an industry that is always evolving, including the company's recent roll out of new AI technology that MiQ believes will change programmatic media.