What turns a promising team into a durable company? John Connors—former Microsoft controller, CIO, CFO, and long-time VC—joins us to dive into the mechanics that actually move the needle: recruiting exceptional people, making clear calls under pressure, and scaling only after the signals are real. From a Montana upbringing marked by hard work on farms and railroads to high-stakes meetings with Bill Gates and Steve Ballmer, John shows how resilience and curiosity become a leader’s edge.

For decision-makers dealing with high-stakes growth and for any leader who’s ever felt alone in tough calls, John opens the door to the Microsoft engine room during hypergrowth: consolidating onto a single SAP instance, building analytics muscle, and transforming IT from a cost center into a strategic proving ground. The dogfooding era comes alive—why no enterprise release shipped without IT’s signoff—and how that cultural shift became peer-powered disruption that reduced downtime, boosted credibility, and gave sales a living case study for enterprise computing.

We also examine leadership tone in a culture obsessed with lowlights over highlights, pointing to Bob Herbold’s calm predictability as a model for keeping the room cool while standards stay high. Sometimes, the most effective call is “not your problem”—focusing leaders where they can make the greatest impact.

Then we get practical about venture and entrepreneurship. John explains why overinvesting early is a trap, how to incubate cheaply until product-market fit shows up, and why timing—catching the right wave—can outweigh raw horsepower. He breaks down the harsh math of VC, the compassion required when it’s time to stop funding the dream, and the three founder traits that matter most: recruit A players, be relentlessly optimistic, and get comfortable being unpopular.

For anyone ready to challenge their comfort zone in venture, corporate leadership, or team-building, this conversation is a masterclass in clarity, courage, and compounding judgment. Real leaders. Real stories. Real action.

If it resonates, follow the show, share it with a builder who needs it today, and leave a review to help more people find these conversations.

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Pull up a chair. There’s always room for your seat at the table.

What if the most valuable seconds of your life aren’t the longest ones—but the ones that ripple the farthest? In this episode, we sit down with Olympian and design thinking expert John Coyle to rethink how performance, memory, and time actually work, and how a few well-designed moments can reshape a career, a team, or a family.

For decision-makers dealing with impossible trade-offs, and for any leader who’s ever felt alone in tough calls, John shares what happens when you stop trying to “fix weaknesses” and instead “run toward the roar.” From Stanford’s product design program to the Olympic Training Center, he discovered that true design thinking means redefining the problem, racing your strengths, and embracing a question-driven approach. That shift not only saved his career but also became a blueprint for business: reorganize teams by talent, detach from first ideas, and commit only once reality proves the fit.

Along the way, we explore the six lenses that real leaders use to unlock outsized outcomes—showing why strengths are specific, weaknesses are broad, and why “not your problem” can actually be a catalyst for growth. The result is peer-powered disruption: a fresh model of leadership built on collaboration, clarity, and courage.

Then we take on time itself. Drawing on neuroscience, John explains why memory is the real currency of time and how to “buy” more of it. The formula is practical and bold: stack risk and uncertainty, uniqueness, emotional intensity, beauty, and flow to wake the amygdala and write thicker memories. From running into storms with your kid, to designing surprise rites of passage, to building travel itineraries that leave room for serendipity—you’ll learn how to create moments that feel bigger and last longer.

For anyone ready to challenge their comfort zone and perform better under pressure, this conversation delivers both mindset and method. Real leaders. Real stories. Real action.

If you’re ready to stop counting hours and start crafting experiences that matter, tune in, subscribe, share with a friend who needs a nudge toward their strengths, and leave a review with one moment you’ll design this week.

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Pull up a chair. There’s always room for your seat at the table.

Martha McSally's life story reads like an action-packed novel—from losing her father at 12 to becoming America's first female fighter pilot in combat to serving as a U.S. Senator. But beneath these remarkable achievements lies a profound journey of self-discovery that offers wisdom for anyone struggling with identity, purpose, and leadership.

For anyone ready to challenge their comfort zone or confront what’s holding them back, this conversation is an invitation to run toward the roar—to face the hard stuff head-on with courage and clarity.

Martha reflects on the sudden loss of her father and his final words to “make him proud”—a mission that propelled her forward but eventually became a weight she had to release. With rare candor, she reveals how grief, grit, and rebellion shaped her path to the Air Force Academy, where she was told women were legally barred from becoming fighter pilots. Her reaction: “That’s exactly what I’m going to do.”

Martha’s approach to leadership—whether commanding fighter missions or navigating Washington’s political turbulence—centers on authenticity, resilience, and mission-focus. She doesn’t sugarcoat her Senate experience, describing Congress as “a different combat zone” where she fought to lead with integrity despite a frustrating environment. “It was one of the highest honors of my life to be a U.S. Senator... and also the most frustrating thing I’ve done in my life.”

Through the six lenses of identity, courage, purpose, leadership, failure, and freedom, Martha challenges leaders to strip away external expectations and get clear on who they really are. Her “I am” statements—unbreakable, courageous, generous—aren’t just affirmations, they’re anchors for decision-making in uncertain times.

For leaders navigating post-pandemic complexities, Martha offers straight talk: your team has to “show up and work,” but leadership today also means creating spaces where creativity and sustainability coexist. She draws a powerful distinction between “whatever it takes” seasons and “good enough” rhythms—an essential mindset shift for long-term impact.

Real leaders. Real stories. Real action. Martha’s journey is more than inspirational—it’s instructional. Her story proves that the most effective leadership isn’t about status or control; it’s about showing up with clarity, conviction, and compassion.

Ready to explore your own edge? Connect with Martha through her adventure experiences or speaking engagements. Visit her website to discover how her unique blend of military discipline, political insight, and soul-deep authenticity can help transform your leadership and your life.

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Pull up a chair. There’s always room for your seat at the table.

There's nothing quite like a family recipe passed down through generations. When that recipe becomes the foundation of a thriving business that spans restaurants and nationwide retail distribution, the story gets even more fascinating.

Dan Costello, CEO of Home Run Inn Pizza and fourth-generation family member, joins us to share the remarkable journey of this iconic Chicago brand. From humble beginnings on 31st Street where his Italian immigrant grandparents hosted Sunday family dinners, to now being available in grocery stores across all 50 states, the Home Run Inn story exemplifies how staying true to your roots while embracing innovation can lead to lasting success.

What started accidentally in the 1950s when a customer requested partially-baked pizzas to take to his Wisconsin summer home has evolved into a frozen pizza powerhouse. Today, the CPG side represents 85–90% of the business, but the restaurants remain vital to their identity and serve as living laboratories for authentic Chicago-style pizza.

Costello candidly discusses the challenges unique to family businesses, including a difficult succession process that ultimately led to one branch of the family exiting the business entirely. He shares how the company's core values of Family, Pride, Grit, and Courage guide decision-making through tough times, including the pandemic when protecting employees while meeting surging demand required transparent leadership.

For any leader who’s ever felt alone in tough calls, Costello’s story offers a grounded look at what it means to run toward the roar—leaning into discomfort and uncertainty with clarity and conviction. His simple but powerful business philosophy: identify what you do that others can't or won't do. For Home Run Inn, it's their dough-aging process—a technique passed down from his grandfather that creates a distinctive taste competitors can't replicate in the frozen pizza market. While other brands develop products in R&D labs, Home Run Inn remains committed to recipes “born in a kitchen.”

This is peer-powered disruption at its most personal—where family legacy meets operational excellence, and tradition fuels innovation.

Ready to taste the difference four generations of pizza-making expertise brings to the table? Look for Home Run Inn in your local grocery freezer or visit one of their Chicago restaurants to experience this family legacy firsthand.

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Pull up a chair. There’s always room for your seat at the table.

Financial leadership isn't just about managing numbers—it's about navigating uncertainty and building resilience. In this candid conversation, Tom Casey draws from his remarkable journey as CFO at institutions including GE Capital, Washington Mutual, Clear Channel, and Lending Club to reveal what truly matters when steering organizations through transformation and crisis.

Casey shares how his blue-collar upbringing instilled the relentless work ethic that became his professional signature. "No one's going to outwork me," he states, explaining how grit propelled him from humble beginnings to executive leadership. His evolution from an intense young professional who could "wear people out" to a strategic leader who builds high-performing teams offers powerful lessons in self-awareness and adaptation.

At the heart of Casey's approach is what he calls the "competency wheel"—the expanding set of skills that exceptional CFOs develop throughout their careers. Early-career financial leaders might master only a quarter of these competencies, while seasoned executives learn to excel across the spectrum from technical accounting to strategic risk management. For companies seeking financial leadership, Casey emphasizes matching specific competencies to current business needs rather than expecting universal expertise.

The relationship between financial leaders and their organizations takes center stage as Casey compares effective finance teams to a race car's braking system. "Why does a race car have big brakes? So it can go fast," he explains, challenging the notion that financial conservatism inherently restricts growth. For anyone ready to challenge their comfort zone, this perspective reframes robust financial controls as tools for confident acceleration—enabling leaders to speed ahead while retaining the ability to adjust course when necessary. In this light, the finance function is no longer the department of "no," but the enabler of strategic acceleration.

Whether you're leading through uncertainty, building financial leadership capabilities, or seeking to strengthen decision-making processes, Casey's framework provides invaluable guidance for navigating today's complex business landscape with confidence and clarity. Real leaders. Real stories. Real action. This is more than theory—it's practical advice for those determined to make an impact.

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Pull up a chair. There’s always room for your seat at the table.

Terry Hill shares her journey from HR professional to C-suite executive, revealing how she learned the "fine art of approximation" after watching male colleagues confidently present rough estimates while she felt compelled to provide decimal-point precision.

• Early career path from retail to American Express to Nationwide Insurance
• Moving from HR into business leadership and the challenges of that transition
• The importance of building strong peer relationships across organizations
• Learning that authenticity is more valuable than trying to fit an executive stereotype
• Managing down versus managing up as a leadership philosophy
• Making tough business decisions with values-based principles
• Creating goals that prioritize people even during difficult business transitions
• The value of having a trusted chief of staff who can provide honest feedback
• Common executive challenges around communication and difficult conversations
• The permanent state of uncertainty in today's business environment
• Advice to take more vacation and build confidence earlier in your career

If you're interested in executive coaching, Terry now works with clients to increase self-awareness and improve leadership effectiveness through mostly referral-based relationships.

🎙️ Enjoyed this conversation?
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Pull up a chair. There’s always room for your seat at the table.

Troy Johnson, co-founder of Slalom Consulting, shares the power of gratitude and how simple moments of appreciation can transform our outlook in both work and life. From his beginnings in Iowa to building a global consulting powerhouse, Troy reveals how authentic connection with people has been the cornerstone of his leadership philosophy and Slalom's phenomenal growth.

• Troy's journey from small-town Iowa to co-founding what would become an 11,000-person global consulting firm
• The serendipitous failed sales call that turned into a 30-year career when Troy met Slalom's founder Brad Jackson
• How Troy transformed traditional recruiting by focusing on relationships first and hiring as a natural byproduct
• The creation of "Slalom buzz" through personal connections rather than traditional marketing
• Troy's evolution as a leader, including the pivotal moment when he overcame his biases against "fluffy" leadership training
• The power of personal mantras like "Everything always works out" and "What's the worst that could happen?"
• Why gratitude remains one of the most powerful tools for transforming our mindset and relationships
• The importance of getting out in the world and making in-person connections in an increasingly digital age

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Pull up a chair. There’s always room for your seat at the table.

What happens when a natural-born entrepreneur with a "Pied Piper" gift for leading others transitions into corporate America? In this episode of Your Seat at the Table, hosts Mike Maddock and John Tobin talk with serial entrepreneur and technology visionary Marty Renkis.

Marty shares his incredible journey from lemonade stands and selling scrap paper as a kid to founding multiple successful tech companies — including TrainerSoft (sold to Outstart) and Smartvue (acquired by Johnson Controls). He opens up about the exhilarating highs and gut-wrenching lows of startup life, the difficult decisions that shaped his path, and the lessons learned about trust, humility, and teamwork.

Now an executive at a Fortune 150 company, Marty reflects on what it really means to lead at scale: shifting from lone visionary to empowering teams, embracing patience, and learning to whisper ideas instead of shouting them.

About the guest:
Marty Renkis is a serial entrepreneur, innovator, and executive at Johnson Controls. He has led groundbreaking work in e-learning, cloud video surveillance, and smart building technologies — holding a robust patent portfolio and scaling businesses to global impact.

About the hosts:
Mike Maddock is the founder of Flourish Advisory Boards, a public speaker, and a serial entrepreneur known for helping leaders turn big ideas into reality.

John Tobin is the co-founder and Executive President of Slalom Consulting, a global consulting firm helping organizations tackle their most ambitious projects and build cultures of trust and innovation.

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Pull up a chair. There’s always room for your seat at the table.