Gen X Legends

Chris Hare never wanted the spotlight—but he knew how to move the system from the inside. In Part 1, the narrative strategist behind Amazon and Microsoft breaks down how one story, told at the right time, can shift billion-dollar strategies—and why Gen Xers might be the best story-readers in the room. >>From Ad World to Strategic Narrative “I started in marketing, but I got tired of talking...

Erika Ayers Badan—CEO of Food52, former CEO of Barstool Sports, board leader, media powerhouse, and author of _No One Cares About Your Career_—lets us behind the curtain. From negotiating screen time as a kid to rewriting the rules as a high-profile executive, she reflects on how grit, autonomy, and unfiltered curiosity shaped everything—from her parenting to her management style. She shares why s...

Erika Ayers Badan isn’t here to polish the truth—she’s here to say it louder.  In this first of a two-part series, the current CEO of Food52 and former CEO of Barstool Sports breaks down the raw realities behind her debut book, No One Cares About Your Career. From writing on commuter trains to fielding hundreds of workplace questions a week, Erika shares why her advice hits different—because it’s...

Sara Lobkovich doesn’t just tell us what strategy is—she shows us who it’s for.  Her book, You Are a Strategist , is more than a guide to OKRs or goal-setting. It’s a toolkit for people who’ve always felt misaligned, misunderstood, or mislabeled in traditional business environments. Drawing from her own experience as a trauma survivor, neurodivergent thinker, and late-diagnosed ADHD strategist, Sa...

Sara Lobkovich didn’t pivot to be edgy. She adapted because the system never fit—and she refused to shrink herself to match it.  In this first of a two-part series, Sara walks us through her nonlinear arc: from teen internet entrepreneur to lawyer, from burnout strategist to behavioral goal-setting expert. Along the way, she reveals how quiet defiance, early activism, and radical self-curiosity he...

Chris Quek isn’t just building startups—he’s building a generation.  In this second half of his story, he shares how selling his inheritance became the launchpad for Thrive, a VC firm that invests in Southeast Asia’s overlooked next-gen entrepreneurs. From structuring value-aligned startups to teaching his kids the principles behind technology, Chris shows how legacy isn’t something you receive—it...

Chris Quek could’ve stayed in the family business and lived comfortably. Instead, he chose a life of uncomfortable clarity.  In this first of a two-part series, Chris shares how he rejected expectations, fled the legacy he was born into, and built an e-commerce business in Malaysia with nothing but grit and guidance from mentors. Now 46, he reflects on what identity really means when you’re not ha...

Holly Bond comes full circle—returning to the recruiting world she once left behind, this time to rebuild it from the ground up. At Facets, she’s proving that scaling a business doesn’t require sacrificing soul. From her pay structure to her candidate experience to her team’s human-first process, Holly is quietly leading a revolution in executive search. She also drops some of the best job-seeking...

Holly Bond didn’t inherit a business or a playbook—she built her own, from the basement up.  In this first of a two-part conversation, she shares how a late return to university, a family health wake-up call, and pure Gen X tenacity drove her to create a kids’ fitness franchise with national impact. Holly’s story is part entrepreneurship, part emotional reckoning, and full of hard-earned wisdom fo...

Gagan Sandhu, in Part 2, pulls back the curtain on what it really means to design financial independence. It’s not about the FIRE movement or early retirement—it’s about knowing your trade-offs and making conscious, math-informed decisions that align with your values. From career reinvention every 10 years to balancing ambition with family time, Gagan offers Gen Xers a refreshingly grounded take o...

Gagan Sandhu didn’t chase freedom. He calculated it.  In this first of a two-part series, the Chicago Booth MBA, former tech exec, and founder of fintech startup Zillion shares how he redefined financial independence—moving beyond buzzwords and into practical action. From his immigrant roots to his pivot from mechanical engineering to Silicon Valley, Gagan shows how knowledge—not speed—builds real...

Wayland Lum walked away from big names like NVIDIA, Korn Ferry, and Chicago Booth out of conviction.  Now the founder of Copperbox, he coaches modern leaders through a philosophy that fuses deep psychology, personal courage, and timeless wisdom. In this episode, he shares the moment he chose purpose over prestige, the emotional realities behind true leadership, and why fear and courage are two sid...

César Couto Ferreira spent over a decade deep in the world of global media—shaping MTV across Europe and Africa, working with stars, and riding the wave from analog to digital. But when Amy Winehouse died, something broke. Not in the headlines, but inside him. He saw how the industry treated artists as content—not people—and decided he couldn’t be part of it anymore. That moment became his call to...

Michael Levitt nearly lost everything to burnout—a heart attack, job loss, foreclosure, and total collapse. But what brought him back wasn’t a digital detox retreat—it was Gen X wisdom: learning to reset without relying on tech.  As the founder of the Breakfast Leadership Network and burnout consultant to global execs, Michael now teaches others how to rebuild. In this episode, he explains why rec...

Steve Monaghan flips the script on innovation culture: experience isn’t a relic—it’s a strategic edge.  As General Partner at FinMir.ai, Limited Partner at True Global Ventures, Independent Non-Executive Director at RAK Bank, and former Chief Digital Officer at both AIA and DBS Bank, Steve brings a cross-industry view forged through decades of deep transformation. From aviation to fintech to AI, h...

Ryota Tanozaki didn’t pivot because of burnout—he pivoted to avoid a trap. While managing a turnaround project in rural Japan, he saw the writing on the wall: stay too long, and his world would shrink. Instead, he chose to bet on himself. He went global, earned an MBA from Chicago Booth, built a career across Facebook and Tabist (backed by Softbank Japan), and led a hospitality startup through one...

Katie Curry doesn’t just manage a multigenerational workforce—she raises one. As a Gen X leader, she draws from both parenting and management to offer real tools for leading Gen Z with clarity, empathy, and pace. Katie doesn’t romanticize change—she makes it strategic. From book recs to career advice to community wisdom, this episode is a field guide for anyone navigating a multigenerational workp...

Katie Curry didn’t just study risk—she lived it. From communist Bulgaria to Wall Street, from rating credit to leading creatives, this Gen X leader has turned reinvention into an art form. In this episode, she shares how to build mental toughness, reframe failure, and lead with both power and humility—without ever chasing a playbook. For Gen Xers who know how to change ambitiously, this is reinven...

Forget hot takes and hustle porn—Josh Geballe has built a career on real outcomes, not optics. As a former IBM exec, startup CEO, crisis-tested public leader, and now head of Yale Ventures, he’s navigated every kind of system—and rewired more than a few. In this episode, Josh breaks down what it takes to lead without ego, make career moves without a roadmap, and support innovation without turning...

From Moscow diplomacy to a U.S. energy startup backed by BlackRock, Irina Filippova has never followed the script—and she’s not about to start now. In this episode, the COO, climate entrepreneur, and former change leadership advisor shares why courage is leadership, why linear careers are a myth, and why integrity is the only metric that matters. >>Built for Change—Literally “I’ve never inhe...

This episode dives into Bond , the new book by Greg Morley—former global DEI head at Moët Hennessy and veteran HR leader at Disney and Hasbro. Vince and Greg unpack the emotional undercurrent of modern work—how a broken culture can push people into burnout and how small moments of recognition can pull them back. With global insight and Gen X clarity, Greg shares what real inclusion looks like on t...

Greg Morley didn’t follow a career path—he carved one. From call centers to the C-suite at Disney, Hasbro, and Moët Hennessy, Greg’s journey is classic Gen X: no shortcuts, no buzzwords, just deep reinvention and human-first leadership. Now, as the author of Bond, he’s showing how inclusion can actually work—without losing your mind or your values. >>From Complaint Calls to Corporate Change...