Reimagining What Already Exists with Jon Staenberg | #16

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?

Creative Leadership As Invitation with Mark Canlis Part 1| #14

What if your company isn't defined by what it delivers—but by the human experience it exists to create? In this episode of What If?, Leslie Grandy sits down with Mark Canlis, owner of Seattle's iconic Canlis restaurant, for part one of a two-part conversation about creative leadership, legacy, hospitality, and culture. For more than 75 years, Canlis has been one of America's most celebrated restaurants. But Mark does not describe the business first as fine dining, cuisine, service, or even customer experience. He describes it as invitation. An invitation to matter. An invitation to be seen. An invitation to turn toward one another. That distinction becomes the heart of this conversation. Because when an organization understands what it is truly here to create, it can adapt without losing itself. Together, Leslie and Mark explore: * Why hospitality is not performance, but an invitation into relationship * How legacy brands can evolve without becoming rigid or nostalgic * Why constraints often become fuel for creativity * How Canlis reimagined itself during the pandemic by asking what it meant to "turn toward" when traditional dining was impossible * Why culture is built through ritual, vulnerability, humor, and shared story * How employee experience shapes customer experience long before a guest sits down * Why Mark does not train staff to follow scripts, but asks what kind of human they are hoping to become * How rituals like the Canlis "Candy Awards," Christmas Eve toasts, open mic nights, shared meals, and playful traditions create trust inside the team Mark challenges a common leadership impulse: to control behavior from the outside in. Instead of scripting hospitality, he starts with desire, humanity, and intrinsic motivation. What does the employee want? Who are they becoming? How can the restaurant help unlock that person? That approach creates a culture where people are not merely executing service standards. They are trusted to create deeply personal, meaningful experiences for guests because they have first experienced belonging, vulnerability, and relationship with one another. Because the invitation to the guest begins with the invitation to the team. And in a world increasingly shaped by automation, monitoring, and efficiency, that kind of human-centered leadership may become more valuable than ever. Reflection question: Are you building a culture that tells people what to do—or one that helps them become the kind of people who know how to care? Next week: Part two continues the conversation with Mark Canlis into creativity, emotional labor, AI, and why deeply human experiences may matter even more in a technology-shaped future.

Can You Teach Creative Thinking with GenAI? with Leonard Boussioux | #13

What if the real skill of working with AI isn't knowing what it can do—but knowing when you need to lead? In this episode of What If?, Leslie Grandy sits down with Leonard Boussioux, assistant professor at the University of Washington's Foster School of Business and adjunct assistant professor at the UW Allen School of Computer Science and Engineering, to explore how humans can collaborate with AI to solve complex problems, build new ideas, and expand creative capacity. Leo's work sits at the intersection of operations, machine learning, artificial intelligence, and creative problem solving. His research investigates how humans and AI can work together more effectively—and why simply adding AI to the process doesn't automatically produce better or more original outcomes. Together, Leslie and Leo explore: * Why AI can make people more creative—but may also reduce diversity of ideas if everyone gets the same "excellent" suggestions * The difference between human-in-the-loop and AI-in-the-loop thinking * Why there is no single formula for when humans should lead and when AI should take more of the exploratory role * How students can build confidence, agency, and creative capacity by using AI to bring their own ideas to life * Why "vibe coding" is more than a technical skill—it's a way to learn orchestration, judgment, and problem framing * How AI-native students may enter the workforce with skills and expectations that leaders are not yet prepared to recognize * Why organizations need AI champions, safe access to the best tools, and cultures that encourage knowledge sharing * How education must evolve to teach not just AI literacy, but ethics, lifelong learning, metacognition, and leadership Leo also shares how he designs his classroom as a kind of adventure—one where students don't just learn tools, but discover what they are capable of building. By asking students to create real products from their own ideas, he helps them move from anxiety about AI to a sense of creative agency. But the conversation also surfaces a critical warning: AI often recombines what it already knows. It may give you good ideas, but it may give everyone else the same good ideas, too. That means the human role is not disappearing. It is becoming more important. Because the future of human-AI collaboration won't be defined by who can generate the most ideas. It will be defined by who can push beyond the obvious, recognize what matters, and steer the system toward something more original, useful, and human. Reflection question: When you work with AI, are you letting it lead you toward the probable—or are you pushing it toward what only you can imagine?

Finding Leverage in Innovation Strategy with Scott Ehrlich | #12

What if the biggest opportunity with AI isn't doing more with less—but doing what wasn't possible before? In this episode of What If?, Leslie Grandy sits down with Scott Ehrlich, Chief Innovation Officer and Head of Corporate Strategy at Sinclair Broadcast Group, to explore how media, technology, and business model innovation are changing as AI reshapes what can be created, personalized, distributed, and scaled. Scott has spent his career navigating major platform shifts—from early OTT subscription services at RealNetworks to digital-first studios, streaming platforms, FAST channels, and AI-enabled media strategy. His perspective is grounded in a simple but powerful idea: A strategy without leverage isn't really a strategy. Today, the mechanics of making things are no longer the biggest constraint. Production is faster. Distribution is broader. AI can generate, iterate, and adapt at speeds that would have been impossible just a few years ago. But that creates a new challenge. When everything can be made, the real question becomes: What should exist at all? Together, Leslie and Scott explore: * Why value is shifting from production capability to judgment, relevance, and timing * How AI changes the creative process by making iteration faster and less expensive * Why personalized storytelling may become a new frontier for media innovation * Why AI-native platforms may become the next operating systems for content discovery * How business models must evolve when audiences consume information inside AI interfaces * How leaders can drive adoption by focusing on one powerful promise: eliminating the toil of work Scott also offers a grounded view of where most organizations are in the AI adoption curve. Before companies can transform workflows, they often need to use AI to improve existing ones. The breakthrough, he argues, starts with helping people remove the frustrating, repetitive work that drains their time and attention. But the bigger opportunity is still ahead. Too much of the current AI conversation is focused on efficiency: fewer people, fewer steps, faster processes. Scott challenges leaders to look beyond that and ask a more expansive question: What new things can we do now that we could never do before? Because the future of innovation won't belong only to those who move faster. It will belong to those who can recognize where new leverage is forming—and use it to create something more meaningful. Reflection question: Are you using AI only to streamline what already exists—or to imagine what could exist next?