Special Sauce

We're trying something new with this episode. Rather than focusing on the guest's career, we're instead going to talk about a specific subject the guest knows a lot about -- and for which we can all benefit from their knowledge. We'll mix this format in every few episodes to "Keep the Sauce fresh."

Today's episode is about "selling into the future." Getting a buyer to buy something before the general market is ready for it takes more than good timing. It takes the discipline of telling the difference between being early and being wrong, the skill of reading trends instead of just watching sales numbers, and the thick skin to handle rejection. Lots of rejection.

Carrie Seifer is an expert on the subject because she sold mobile advertising back when the Palm Pilot counted as cutting-edge, pitched early applications of AI in advertising way before the concept of AI went mainstream, and was a CRO in roles that required her to prove out categories with no track record to point to.

Carrie and Jordan get into how you actually catch yourself before your conviction turns into delusion, why the hardest sale is often the one you might have to make to your own colleagues, how leaders know about what's coming before their staff do (and what they should do about it), and the notion of getting people to buy into an idea because they helped build it themselves.

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.