Bryan Wiener, Founder and Chairman of AI Startup 37Arc

Amanda Richman, VP of Global Media Sales at Microsoft

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, Founder and Chairman of AI Startup 37Arc

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, President at Mediaocean

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, SVP of Media Sales at the National Football League

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, Chief Creative Officer at Digitas North America

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!).