Curiosity & Agency: The Stars of Your Second Act with Jay Samit | #19

Curiosity & Agency: The Stars of Your Second Act with Jay Samit | #19

What if your second act isn't something you retire into—but something you actively create? In this episode of What If?, Leslie Grandy sits down with Jay Samit, international bestselling author, serial entrepreneur, former Independent Vice Chairman of Deloitte Digital, and author of The Second Act Advantage, to explore why the traditional idea of retirement is overdue for disruption. Jay has spent his career running toward disruption rather than away from it. He has pioneered breakthrough technologies used by billions, helped grow companies including LinkedIn, Sony, and Universal Studios, advised Fortune 500 companies, raised hundreds of millions for startups, and more recently launched a career as an artist exploring the impact of AI and technology on human life. Now, he is turning his attention to one of the biggest personal disruptions many people will face: what happens when work no longer defines us? Together, Leslie and Jay explore: * Why retirement can become a dangerous myth when it removes purpose, structure, identity, and connection * How curiosity and agency become essential skills for navigating a meaningful second act * Why the question should shift from "What will I do in retirement?" to "What can the world gain now that I have time?" * How AI can help people rediscover purpose, build businesses, learn new skills, and act on ideas faster than ever before * Why Jay created "Digital Jay," an AI mentor designed to help readers personalize their second-act journey * How disruption is not about what happens to you, but how you respond * Why purpose, human connection, creativity, and contribution are central to longevity and fulfillment * What high performers often misunderstand about identity when their title, routine, or professional status changes Jay challenges the familiar idea that retirement is a finish line. For many people, it is actually an identity disruption. The structures that once gave life shape—meetings, titles, colleagues, goals, performance, recognition—suddenly disappear. And without curiosity, agency, and a clear sense of purpose, that freedom can feel less like liberation and more like drift. But Jay offers a different possibility. Your second act can become the most creative chapter of your life. It can be a time to apply hard-earned wisdom, build something new, solve a problem that matters, mentor others, create art, launch a business, strengthen community, or leave a legacy that extends beyond achievement. And AI, rather than being something to fear, can become a powerful force multiplier—especially for people willing to keep learning. Because the people who thrive in their second act will not be the ones who wait for the world to tell them what comes next. They will be the ones curious enough to ask what if—and agentic enough to act on the answer. Reflection question: What wisdom, curiosity, or unfinished idea are you carrying that could become the beginning of your second act?

The Superpower of I Don't Know with Hortense le Gentil | #18

What if the most powerful thing a leader can say right now is, "I don't know"? In this episode of What If?, Leslie Grandy sits down with Hortense le Gentil, executive leadership coach, speaker, and author of Aligned and The Unlocked Leader, to explore why the future of leadership requires something very different from the old superhero model. For decades, leaders have been rewarded for projecting certainty. They were expected to have the answers, set the direction, stay composed, and absorb the pressure. But in a world moving faster than any one person can fully understand—especially as AI reshapes work, decisions, and expectations—that model is becoming impossible to sustain. And maybe the real breakthrough begins when leaders stop pretending it is. Together, Leslie and Hortense explore: * Why the "superhero leader" model leaves leaders exhausted and teams disconnected * How saying "I don't know" can build trust instead of weakening authority * Why self-awareness is the foundation for more human leadership * How fear, perfectionism, and old success patterns become leadership traps * Why leaders must learn to invite their fears to the table without letting those fears lead * How AI makes empathy, intuition, creativity, and emotional nuance more important—not less * Why leaders need to stop competing with AI and start deepening the capabilities that make them human * How to create environments where people feel safe enough to question, experiment, fail, and grow Hortense offers a powerful reframe for this moment: leadership is not about being the smartest person in the room. It is about creating the conditions where others can contribute what they see, know, question, and imagine. That starts with humility. Not the passive kind. The courageous kind. The kind that says: I do not have all the answers, and I am willing to learn with you. Because in a world where change is constant and certainty is scarce, "I don't know" is not a weakness. It may be the beginning of trust, creativity, and real transformation. Reflection question: Where are you still trying to lead by having all the answers, when your team may need you to model the courage to learn?

Better Questions Are the New Answers with Prapti Jha | #17

What if the real advantage in the age of AI isn't getting answers faster—but knowing which questions are worth asking? In this episode of What If?, Leslie Grandy sits down with Prapti Jha, design thinking and innovation consultant, co-founder of We Speak Innovation, and former design thinking catalyst at Ford Motor Company, to explore what happens when AI enters the world of human-centered design. On the surface, AI looks like a powerful accelerator. It can synthesize research, generate personas, benchmark competitors, summarize markets, and prototype ideas at a speed that once seemed impossible. But speed is not the same as insight. And efficiency is not the same as understanding. Together, Leslie and Prapti explore: * Why human-centered design depends on real observation, context, and ambiguity * How AI can support innovation without replacing the discipline of understanding real human behavior * Why AI-generated personas are useful but dangerous when mistaken for actual human insight * What organizations lose when they compress time for exploration and questioning * Why innovation labs often fail when they are isolated from the rest of the organization * How embedding "innovation catalysts" across teams can shift culture more effectively than separating innovation into a protected lab * Why the skills once called "soft" are becoming the hardest and most important capabilities in the age of AI * How organizations can assess AI maturity by asking employees what problems they are solving or what opportunities they are creating with AI Prapti also introduces the idea that AI maturity is cultural, not just technical. Immature organizations use AI primarily to move faster. More mature organizations use AI as a collaborator—one that helps people challenge assumptions, surface contradictions, and make better decisions. That distinction matters. Because bad processes plus AI do not create innovation. They create faster bad outcomes. This conversation is a reminder that the human role in innovation is not disappearing. It is becoming more essential. AI can support research, synthesis, prototyping, and decision-making, but it cannot fully capture context, emotion, irrational behavior, or lived experience. Human-centered design still begins with humans. And in an AI-accelerated world, the advantage belongs to organizations that protect the time, curiosity, and courage required to ask whether the answer they received is actually the right one. Reflection question: Are you using AI to get to answers faster—or to ask better questions about what truly matters?

Reimagining What Already Exists with Jon Staenberg | #16

What if entrepreneurship isn't always about starting from scratch—but seeing what an existing business could become? In this episode of What If? With Leslie Grandy, I sit down with Jon Staenberg, general partner at Agate Hound Fund, the first fund of funds dedicated to search funds, also known as entrepreneurship through acquisition. Jon has spent decades investing in people, businesses, and ideas. From venture capital to private equity to winemaking in Argentina, his career has been shaped by curiosity, pattern recognition, and a willingness to ask both sides of the entrepreneurial question: What if it all goes wrong? And what if it works? This conversation explores a different kind of entrepreneurial creativity. Not the creativity of inventing something from nothing, but the creativity of stepping into an existing company with employees, customers, habits, and history and seeing how it can be adapted, strengthened, and carried forward. Together, Leslie and Jon explore: * Why search funds are better understood as entrepreneurship through acquisition * How acquiring and operating a profitable small business differs from venture-backed invention * Why grit, tenacity, humility, and a clear "why" matter more than polish * What Jon looks for when backing first-time CEOs * Why immigrants, military veterans, and children of family business owners often bring the right temperament for this path * How investors evaluate a searcher over time through coachability, humility, judgment, and persistence * Why the coming generational handoff of baby boomer-owned businesses creates a powerful opportunity * How AI-native operators can modernize "good, boring businesses" faster than legacy owners may be able to imagine Jon also shares the story of how he unexpectedly became a winemaker after a long lunch in Argentina, and why selling his vineyard after 20 years is less an ending than a transition. The thread that remains is community: bringing people together, building trust, creating value, and knowing when to move toward the next thing. This episode is a reminder that creativity is not limited to invention. Sometimes the most creative act is recognizing untapped potential in something that already exists, then having the discipline, humility, and stamina to make it better. Because transformation does not always begin with a blank page. Sometimes it begins with a business that deserves a next chapter. Reflection question: Are you overlooking the possibility inside what already exists because you're waiting for something entirely new?

The Human Experience Can't Be Automated with Mark Canlis Pt 2 | #15

What if the future of leadership isn't about more control, but more permission? In part two of Leslie Grandy's conversation with Mark Canlis, owner of Seattle's iconic Canlis restaurant, the discussion moves beyond hospitality into a bigger question: what happens to human connection, creativity, and emotional experience in a world increasingly shaped by technology? In part one, Leslie and Mark explored legacy, ritual, culture, and hospitality as invitation. In this continuation, they go deeper into the emotional work of leadership and service, and why deeply human experiences may become even more valuable as AI becomes more embedded in our daily lives. Mark does not see hospitality as performance. He sees it as relationship. That distinction changes everything. Together, Leslie and Mark explore: * Why service can be exhausting and restorative at the same time * How emotional labor becomes meaningful when it connects to purpose * Why guests often leave Canlis feeling "restored," even when they may not have the words to explain why * How fine dining safeguards important emotional moments, from anniversaries to last meals with loved ones * Why authentic connection, craft, and presence cannot simply be automated away * How small business owners can build cultures where people bring their whole selves to work * Why leaders must model vulnerability before asking it of others * How play, creativity, and permission help people break free from organizational gravity Mark also offers a powerful challenge to leaders: stop asking employees to perform humanity from a script. Instead, create an environment where people are trusted, known, and invited to care from who they truly are. The conversation closes with a reflection on Creative Velocity and the conditions required for creativity to flourish at work. Leslie reframes velocity not as speed for speed's sake, but as momentum with direction: the ability to break free from the gravitational pull of fear, bias, control, and convention. Because creativity does not thrive in cultures where people are merely told what to do. It thrives where leaders lower the gravity. Where people feel safe enough to try, fail, ask, play, and bring forward what only they can see. And in a world where AI can automate more tasks, the most valuable experiences may be the ones that feel unmistakably human. Reflection question: Are you creating a workplace where people feel controlled into performance, or invited into their full humanity?