Overwhelmed by life? Alison Stewart gets it—and she’s building a startup to help fix it. In Part Two , the Overalls COO shares how her team is rethinking employee benefits by offering something surprisingly human: life support, literally. Whether it’s booking a plumber, navigating eldercare, or finding summer camps before the January rush, Overalls acts as a concierge for the chaos of modern life. Alison also opens up about what it really takes to scale an idea from zero—while trusting yourself ...
May 18, 2025•34 min•Ep. 379
Not all career changes are dramatic. Some are deeply deliberate—and a little serendipitous. In Part One , Alison Stewart, COO of Overalls, walks us through her transition from 10+ years in the financial sector to co-founding a startup she discovered on LinkedIn. With two kids at home and a stable job in a Fortune 100 company, Alison didn’t jump recklessly. Instead, she asked the hard questions: Am I fulfilled? What do I want next? And how much risk am I really willing to take? This episode unpac...
May 18, 2025•23 min•Ep. 378
Most people retire after one successful business. Ral West kept building. In this episode, Ral shares how she co-ran a charter airline between Alaska and Hawaii for 25 years—eventually selling it to Alaska Airlines—and then launched into her next chapters: owning cruise ships, investing in real estate syndications, and helping other entrepreneurs find sustainability without burnout. From navigating gender bias in a family business to designing automated booking systems and letting go of control ...
May 17, 2025•28 min•Ep. 377
Comebacks rarely happen all at once. They’re built in small moments, with slow wins. In Part Two , Athena Brownson opens up about what it really takes to rebuild when chronic illness becomes your new normal. She walks us through her mindset rituals, the power of written affirmation, and how she finally learned the one thing no athlete ever wants to admit: she couldn’t do it alone. From retraining her brain to let go of pain patterns, to redefining leadership through delegation, Athena shares a p...
May 17, 2025•25 min•Ep. 376
At 25, Athena Brownson was a rising star in real estate with a pro skiing past and unstoppable energy. Then came Lyme disease—a diagnosis that would upend her health, identity, and entire way of life. In Part One , Athena shares the unfiltered truth of what it means to live with a chronic, invisible illness for nearly a decade. From neck surgery to plasma transfusions, she walks us through the daily battles, emotional toll, and quiet strength it takes to show up—even when she doesn’t want to. Th...
May 17, 2025•29 min•Ep. 375
What do janitors, jazz musicians, and neuroscientists have in common? According to Dr. Nicole F. Roberts, everything. In Part Two , the Doctor of Public Health and co-author of Generosity WINS unpacks how she and Monty Wood turned a business book into a narrative experiment—part fiction, part real-world leadership case study. She shares how they chose a fictional hotel manager named Emily to guide readers through generosity’s ripple effects, and how each chapter’s QR code links to a real leader ...
May 17, 2025•37 min•Ep. 374
What happens when your five-year plan falls apart—and you start to like it that way? In Part One , Nicole F. Roberts—Doctor of Public Health, human rights founder, and co-author of Generosity WINS —shares the real story behind her very unpolished path. From flunking chemistry and walking away from med school dreams to launching a human rights firm mid-dissertation, Nicole proves that success isn’t always strategic—it’s responsive, human, and messy in the best way. We explore how her neuroscience...
May 16, 2025•27 min•Ep. 373
What does generosity look like in a divided, distracted world? In Part Two , Monte Wood—former CEO of Opus Agency and author of Generosity Wins —dives deeper into how generosity gets lost in the noise of modern life and what it takes to reclaim it. From quiet reflections on Steve Jobs’ legacy to a chance encounter with Elon Musk in a hotel hot tub, Monte shares how generosity can take many forms—and why practicing it daily is the ultimate leadership move. He also unpacks the forces working again...
May 16, 2025•25 min•Ep. 372
Is generosity a nice-to-have—or a career superpower? In Part One , Monte Wood, former CEO of Opus Agency and author of Generosity Wins , makes the case for generosity as a leadership strategy with real-world ROI. Drawing from personal stories, his time working with legends like Steve Jobs, Andy Grove, and Mark Benioff, and life lessons from his own mentors, Monte shares how small acts of generosity can ripple out into long-term success—and why true generosity isn’t transactional, it’s transforma...
May 16, 2025•34 min•Ep. 371
Paul Austin isn’t here to evangelize psychedelics. He’s here to demystify them. As the founder and CEO of Third Wave, Paul has spent a decade educating the public on responsible psychedelic use—from microdosing protocols to full-dose journeys. In this episode, he shares how psychedelics are being used not just to treat mental health conditions, but to enhance leadership, decision-making, and personal clarity. We explore the science of neuroplasticity, the legal gray zones, and the risks of skipp...
May 16, 2025•40 min•Ep. 370
After launching a global anti-trafficking movement in his teens, Chris Schrader didn’t settle down—he leveled up. In Part Two , the founder of the 24 Hour Race draws parallels between navigating the Gobi Desert and leading high-growth businesses across continents. From dropping out of Harvard to leading expeditions and scaling software companies, Chris shares why building teams isn’t about maximizing your strongest players—it’s about supporting your weakest. And why sometimes, real leadership me...
May 14, 2025•35 min•Ep. 369
Sometimes the biggest movements begin with a simple question: What can I do? In Part One , Chris Schrader, founder and executive chairman of the 24 Hour Race, shares the unfiltered origin story behind the world’s largest student-run movement to fight human trafficking. What started as a walk across England in memory of a friend became a 24-hour endurance race, then a global platform that’s raised over US$20 million across 25 cities. But Chris doesn’t romanticize it. He breaks down how it all cam...
May 13, 2025•27 min•Ep. 368
In today’s world, financial advice is everywhere—but rarely helpful. In Part Two , Michael Sakraida continues dismantling outdated ideas about wealth, offering a fresh framework that centers emotional intelligence and personal values. He explains why legacy isn’t just about what you leave behind, but how you live today. From the limits of “aggressive investor” labels to the chaos of unregulated financial influencers, Michael unpacks the hidden damage done by bad advice—and what real financial co...
May 13, 2025•23 min•Ep. 367
Michael Sakraida didn’t write a money manual. He wrote a mindset shift. In Part One , the author of Money, Balance and Joy shares how his upbringing, career in finance, and burnout led him to a new definition of wealth—one that includes time freedom and emotional fulfillment, not just financial metrics. He questions why Wall Street ignores the emotional toll of economic instability and how media-driven fear only adds to our sense of isolation and failure. This episode covers the emotional underb...
May 13, 2025•25 min•Ep. 366
You’re exhausted. The meetings are pointless, the politics are draining, and your boss sends Slack messages that trigger a fight-or-flight response. It feels like the only answer is to walk away. But what if there’s another way? In this episode, executive coach and author Darcy Eikenberg shares how to turn burnout into clarity without updating your résumé. Drawing from her book Red Cape Rescue: Save Your Career Without Leaving Your Job , Darcy walks us through how to reset how you think, revise ...
May 13, 2025•37 min•Ep. 365
What happens after you’ve lost everything—status, stability, and even your sense of self? In Part Two , Sihame El Kaouakibi goes deeper into her journey of rebuilding: not just her career, but her core identity. From leaving toxic environments to redefining ambition, Sihame breaks down how Women Leaders OS came from her own healing, and how she now helps high-achieving women across cultures do the same. She also opens up about why global coaching requires cultural fluency, why some success stori...
May 12, 2025•35 min•Ep. 364
What happens when a rising political star crashes—publicly, painfully, and all at once? In Part One , Sihame El Kaouakibi, Moroccan-born former Belgian MP and five-time founder, shares the deeply personal story behind her public unraveling. Once a celebrated social entrepreneur and national leader, Sihame faced burnout, betrayal, and bankruptcy—all while navigating racism, politics, and impossible expectations. But instead of disappearing, she rebuilt. This episode is a raw look at what it means...
May 11, 2025•27 min•Ep. 363
Starting a franchise isn’t just a business move—it’s a mindset shift. In Part Two , James Hilovsky—former athlete turned franchise consultant—goes beyond playbooks and into the real psychology of success. He explores why some athletes stumble when they let ego overtake strategy, how corporate professionals can regain control after layoffs, and why betting on yourself only works when you’re honest about what kind of help you need. From risk tolerance to leadership, coachability to due diligence, ...
May 11, 2025•28 min•Ep. 362
What happens after the cheering stops? For James Hilovsky, it meant trading his baseball uniform for business ownership—and helping other athletes do the same. In Part One , James shares how his short-lived pro sports career led to 25 years in restaurant franchising, including scaling Pieology from one store to over 100. Now, as a franchise consultant, James works with NFL and NBA players looking to invest wisely, build generational wealth, and transition from the field to the franchise world. H...
May 11, 2025•27 min•Ep. 361
If students are graduating into a broken job market, can we really call that success? In Part Two , Bridget Burns, CEO of the University Innovation Alliance, zooms out to expose the cracks between graduation and employment—and shares what it actually takes to close them. From outdated career services buried in basement offices to siloed AI initiatives happening in secret, Bridget makes the case for a total redesign of higher education’s operating system. With a blend of empathy and systems think...
May 10, 2025•28 min•Ep. 360
If higher education feels like the Hunger Games, Dr. Bridget Burns is building the resistance. In Part One , Bridget shares her journey from growing up in rural Montana to becoming CEO of the University Innovation Alliance—a national coalition of public research universities working together (yes, together) to improve outcomes for low-income and first-generation students. She pulls back the curtain on the real problem in academia: a culture of competition, hierarchy, and duplicated failure maske...
May 10, 2025•31 min•Ep. 359
Let’s be honest—today’s job search often feels like shouting into the void. In Part Three , Mary Shea—former General Manager at HireQuotient and co-CEO at Mediafly—tackles the modern job market from both sides of the table. She pulls back the curtain on how AI is reshaping recruitment: from sourcing passive candidates to fighting unconscious bias, automating outreach, and uncovering overlooked talent. But this isn’t a tech sales pitch—Mary gets real about what AI can’t do (like fix a broken cand...
May 10, 2025•43 min•Ep. 358
Is two better than one? In Part Two of this series, Mary Shea—former co-CEO of Mediafly and former General Manager at Hire Quotient—shares how she navigated one of the most unconventional leadership models in business: co-CEOship. From building trust with her co-leader to balancing responsibilities across time zones and product lines, Mary unpacks the human side of shared power—and why mutual respect beats ego every time. She also explores how AI is transforming sales effectiveness, not just eff...
May 10, 2025•26 min•Ep. 357
Mary Shea didn’t follow a traditional path. She composed her own. In Part One of this three-part series, Mary walks us through the bold decisions that took her from professional oboist to PhD to sales analyst—and eventually to co-CEO of Mediafly. Along the way, she’s picked up more than titles: she’s developed a philosophy that blends intellectual rigor, creative play, and social equity. She opens up about what it’s like to enter the business world a decade “behind” her peers, the financial free...
May 10, 2025•23 min•Ep. 356
Becoming Singapore’s youngest parliamentarian was just the beginning. In Part Two of this conversation, Tin Pei Ling reflects on how she’s evolved as a leader, mother, policymaker, and public voice. From walking the campaign trail just days after giving birth, to pursuing an MBA mid-term while managing a constituency, her path isn’t about having it all—it’s about knowing what to give, and when. She opens up about the guilt of missing milestones, the value of learning from older peers, and the re...
May 08, 2025•22 min•Ep. 355
What happens when your first job in politics comes with public ridicule, online harassment, and sky-high expectations? At 27, Tin Pei Ling became Singapore’s youngest female Member of Parliament. But what looked like a bold milestone from the outside was also the darkest chapter of her life. In Part One of this candid conversation, Pei Ling opens up about walking away from a stable consulting job, the backlash she faced as a “too young” candidate, and why she chose to fight for trust instead of ...
May 07, 2025•21 min•Ep. 354
Would you leave a powerful career in global banking, pack up your family, and start over in a developing country? That’s exactly what Fatou Sagna Sow did. Born and raised in Paris, she built a high-flying legal career at some of the world’s top banks—leading teams, managing billion-dollar deals, and thriving in the French system. But it wasn’t enough. In 2016, she returned to Senegal to write a new playbook—one rooted in identity, impact, and intercontinental connection. In this episode, Fatou s...
May 07, 2025•34 min•Ep. 353
Hybrid work was supposed to be the future—but it’s feeling more like a tug-of-war. Wayne Turmel, co-author of The Long-Distance Leader , has spent two decades studying how we lead across distance—and what falls apart when we don’t. In this episode, Wayne explains why most return-to-office plans are more negotiation than strategy, how unexamined proximity bias silently shapes promotions, and why hybrid leadership isn’t about place—it’s about intentionality . Whether you’re managing global teams o...
May 07, 2025•32 min•Ep. 352
The way we communicate is changing—but what does that mean for the humans doing the talking? Dr. Juliana Schroeder, associate professor at UC Berkeley Haas, has spent her career unpacking how we perceive other minds—both human and machine. In this episode, she breaks down how AI isn’t just reshaping tech—it’s reshaping the psychology of communication itself. From virtual assistants to algorithmic bias, and from voice cues to power dynamics, Juliana offers a grounded look at what we gain (and ris...
May 06, 2025•35 min•Ep. 351
Confidence might be the most overused word in leadership—but Lucy Gernon is here to give it teeth. After two decades in the pharmaceutical world, Lucy faced a moment of reckoning when a family tragedy pushed her to stop waiting and start living on her own terms. Now, as a multi-award-winning executive coach and founder of the Executive Presence Blueprint, she helps high-achieving women get out of their own heads—and into positions of power. In this episode, Lucy opens up about overcoming self-do...
May 06, 2025•30 min•Ep. 350
