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.