Second Life Leader

This is Seeing Through the Illusion. Operational Restatement: Closing the Interview Loop. Over the past several years, this feed has published more than four hundred conversations. When I launched the show, the objective was standard: explore leadership, dissect operational success, and interview operators across various industries. But after four hundred iterations of this show, the truth is unmi...

What happens when the systems that helped your business grow become the things holding it back? For Rob Calvert, that question has become a central part of helping businesses navigate the realities of distributed teams. As companies moved from local offices to teams spread across states, countries, and time zones, the technology supporting them became increasingly complex. Devices need to be prote...

What happens when achieving the success you thought you wanted leaves you asking, “Now what?” For Kris Land, that question became the beginning of a much deeper exploration. After selling a company and making significant money, Kris found himself unexpectedly depressed. He had accomplished the goals he thought he was supposed to accomplish, but instead of feeling fulfilled, he was left with a sens...

What happens when rapid success becomes unsustainable? For Colin Hodge, the answer came through a painful lesson. After building a startup that reached 1 million users in roughly three months , Colin found himself under enormous pressure—scaling infrastructure, recruiting a team, experimenting with growth tactics, and dealing with a major trademark lawsuit. Then Apple told him his app would be rem...

Ritam Gandhi joins the conversation to discuss why the next wave of AI disruption won’t just impact entry-level jobs—it will fundamentally reshape careers at every stage. The discussion explores how artificial intelligence is lowering the barriers to entrepreneurship while simultaneously increasing the need for adaptability. As traditional career paths become less predictable, professionals may fi...

Nick Darragh joins the conversation to explore how today’s financial landscape has been shaped by years of cheap capital—and why the consequences are only now becoming impossible to ignore. The discussion examines how prolonged low interest rates fueled massive investment into technology companies, encouraged unsustainable business models, and created an environment where growth often mattered mor...

Darryl Moon joins the conversation to challenge one of the biggest assumptions about healthcare: That rising healthcare costs are simply unavoidable. They aren’t. Drawing from decades of experience leading hospitals as a CFO, COO, and CEO, Darryl explains why many healthcare systems are built around incentives that often conflict with the goals of employers and patients alike. Rather than focusing...

Greg Moore joins the conversation to unpack one of the biggest misconceptions in entrepreneurship: That buying a franchise automatically reduces the risk of building a business. It doesn’t. A franchise can provide systems, brand recognition, training, and operational support—but none of those replace the fundamentals of business ownership. We began with a candid discussion about failed franchise e...

Karl Madelin joins the conversation to explore a challenge most people rarely think about until food prices rise or health problems emerge: the relationship between agriculture, nutrition, and the systems that shape what ends up on our plates. We started with a simple observation. Food isn’t just agriculture. It’s economics. It’s health. It’s culture. And ultimately, it’s community. Karl brings ex...

Randal Thames joins me to explore a question that’s becoming harder to ignore: What happens when the skills, systems, and assumptions that built your success stop being enough for what comes next? We started with a simple observation. Most people think reinvention happens after disruption. But the people who thrive rarely wait that long. They see change coming before it becomes obvious. Randal bri...

Matthew Le Merle joins the conversation to explore a different kind of leadership and life challenge—one that quietly shapes careers long before people realize it: the ability (and willingness) to reinvent yourself before disruption forces it on you. We started with a simple tension. Most people don’t fail because they’re not capable. They fail because they stay too long in systems that are alread...

Damon Flowers joins me to unpack something most founders and operators only discover after repeated failure: the real battle isn’t in the market—it’s in the mind. We started with a simple but uncomfortable pattern. People don’t usually fail because they lack skills. They fail because they can’t consistently use them when it matters. Under pressure, fear shows up. Avoidance kicks in. Old identity p...

David Hanner joins me to unpack one of the most difficult transitions any company faces: How do family businesses grow without losing the character that made them successful in the first place? We started with a simple reality. Growth creates complexity. And in manufacturing businesses—especially family-owned companies—that complexity compounds fast. Inventory, cash flow, dealer networks, financin...

Scott Bowman joins me for a conversation that starts in finance—but quickly turns into something much bigger. We unpack the transition from high-pressure investment banking to leading mission-driven companies focused on sustainability, second chances, and long-term impact. Scott spent years inside the world of constant travel, deal-making, capital raises, and relentless growth. The work was financ...

Lisa Leveille joins me to unpack a different kind of leadership challenge—one that quietly burns people out long before they realize it: the inability to create boundaries. We started with a simple observation. The more capable you are, the more responsibility people hand you. And in leadership roles—especially in finance—that responsibility expands fast. HR, operations, procurement, reporting, st...

Cody Kopas joins me to unpack a different kind of pattern—one that doesn’t show up in headlines, but quietly shapes careers, families, and entire regions: why people leave the Midwest to grow… and then come back to build. We started with a simple observation. For decades, talent has flowed out of the Great Lakes region—into coastal cities, into capital-heavy ecosystems, into faster-moving opportun...

Robin Goad joins me to unpack a different kind of failure—one that doesn’t show up on balance sheets, but shapes entire lives: the gap between what we’re told about success and how life actually works. We started with a simple observation. There are entire industries built around preparing you for short phases of life—college, careers, even pregnancy. But almost nothing prepares you for the next 5...

Enterprise systems leader Kevin Patrick joins me to unpack a problem most companies underestimate—and pay for heavily: employee disengagement. We started with a stat that should stop any executive cold. Roughly 70% of ERP implementations fail to hit their goals. At the same time, employee disengagement globally accounts for an estimated $8.8 trillion in lost productivity every year. Those two numb...

Entrepreneur and marketing strategist Kalen Cotto joins me to unpack what really happens when life, business, and identity all start collapsing at once—and how you actually rebuild from there. Most conversations about success focus on strategy, tactics, and growth curves. This one doesn’t. Kalen and I dig into the uncomfortable middle—the part where things fall apart, confidence drops, income disa...

Founders, operators, and executives talk endlessly about strategy, data, and execution—but avoid the deeper forces shaping every decision they make. In this episode of Second Life Leader , Doug Utberg sits down with Asha LaCount to explore what happens when leadership goes beyond surface-level EQ—and into the uncomfortable, often unspoken realities of energy, identity, and polarity. This is not a...

Founder and creative professional Preston Zeller joins me to unpack a conversation most workplaces avoid—but everyone eventually faces: grief, and how it reshapes the way we work, lead, and live. This episode starts with a moment that changes everything. In early 2019, Preston lost his brother unexpectedly to a drug overdose. At the same time, he was navigating intense professional pressure during...

Commercial cleaning and AI don’t naturally belong in the same sentence. At least, not at first glance. But that’s exactly why this conversation matters. In this episode of Second Life Leader , Doug Utberg sits down with Adam Povlitz to break down what it actually looks like to build an AI-first mindset inside a very human, operationally messy business. Because the future of AI in service industrie...

Founder and PR strategist Bryce North joins me to break down a counterintuitive truth: the more you try to look like the smartest person in the room, the less people trust you—and the less business you close. Most professionals believe authority comes from showcasing intelligence, credentials, and polished expertise. This episode challenges that assumption. Bryce unpacks why over-positioning yours...

Entrepreneur and author Tero Moliis joins me to explore a deceptively simple idea: if nothing lasts, what actually matters? This conversation starts with Tero’s philosophy from his book Life Is a Sandcastle —the idea that everything we build eventually disappears. The question isn’t whether the wave comes. It’s what you do knowing that it will. Most people interpret nihilism as hopeless: nothing m...

Capital gains taxes don’t usually sound like the beginning of a collapse story—but in this episode, they are. Brett Swarts, founder of Capital Gains Tax Solutions, joins me to break down a hidden risk many investors and entrepreneurs overlook: getting trapped between tax exposure, debt, and timing. What starts as a smart growth strategy can quietly turn into a situation where selling isn’t viable,...