Second Life Leader

Entrepreneur and sales strategist Doug Brown joins me to unpack what really happens when success collapses—and why the ability to rebuild matters more than avoiding failure. Most business conversations glamorize wins and sanitize losses. This episode does neither. Doug Brown and I walk through the uncomfortable reality of losing millions, starting over with almost nothing, and repeatedly reinventi...

Ex-corporate operators don’t fail because they’re dumb. They fail because they try to play entrepreneurship like a safe promotion instead of a thousand-run swing of the bat. In this episode of Second Life Leader , I sit down with Roger Martin —former pharma COO who walked away at 46 from the “sharp suit + stock options” life to wake up on a Monday with no salary, no benefits, and no safety net . S...

Most men were taught the same script: make more money, buy the bigger house, upgrade the cars, send the kids to better schools… and then you’ll be worthy of love, respect, and a “good life.” What if that script is actually wrecking relationships, families, and mental health? In this episode, I bring back social worker and men’s advocate Jack Kammer for a very un-LinkedIn conversation about money,...

This one hits deeper than a startup story. I sat down with Kal Merhi , founder of iRoomit , and what began as a simple “Airbnb-for-roommates” conversation turned into a masterclass in resilience, reinvention, and building something that actually serves people. Kal grew up in Beirut during the civil war—fifteen years of survival, homelessness, and walking miles every morning just to get water. He c...

COVID pulled supply chains out of the background and into daily life. What used to feel abstract suddenly determined whether shelves were stocked, prices stayed stable, or businesses survived at all. In this conversation, Kerim Kfuri breaks down how global supply chains actually work, why the old “lowest cost at all costs” logic is outdated, and how disruption has reshaped manufacturing, trade, an...

For decades, leadership meant position: titles, layers, authority flowing downward. That model survived generations of management theory—but AI is dismantling it faster than most organizations realize. As automation absorbs middle management functions and teams flatten, leadership no longer comes from the org chart. It emerges from trust, psychological safety, and the ability to guide without cont...

After an 18-year rise through corporate HR—from recruiter to group president across Canada and the U.S.—Dom walked away from a “safe” executive career to build something on his own terms. In this conversation, we unpack why large organizations quietly trade momentum for bureaucracy, how technology and automation empower lean founders, and why “stability” often comes at the cost of creativity, spee...

Most of us chase home on the outside — new careers, new cities, new missions — assuming the right setting will unlock the right identity. But for Socratese, home wasn’t Boston, the Army, or the next achievement. It was the inner place he had been trained to outrun. In this episode, we unpack why so many high-performers hit professional milestones but feel spiritually homeless, how “hero’s journey”...

Rita Malvone did — but only after it nearly burned her out as a leader, a human, and as someone trying to make sense of a career that never quite felt like hers . In this episode, Rita and I unpack the quiet misery of high-performing corporate people: the ones who smile on Zoom, hit the metrics, answer Slacks at 11 p.m.… and privately wonder why they feel so damn empty. Rita’s story starts in Chin...

In this episode, business transformation powerhouse Dr. Darnyelle Jervey Harmon joins me to talk about the moment she looked at her wildly successful company… and realized she hated it. This isn’t a story about hustle culture or “girlboss bounce-backs.”It’s about bankruptcy, rebuilding with intention, and choosing a business that loves you back. We break down the difference between scaling and sel...

From Wall Street’s “culture of no” to early-Google hypergrowth to building a consulting business in Memphis with three kids, Meg lived the arc most founders dream about—and learned that money is only one measurement. Freedom, contribution, intellectual fulfillment, and time with family often matter far more. In this episode, we trace her journey from HR leader to entrepreneur, why business develop...

Most people treat their career pivot like a crisis. Adam approached his like compounding interest — small, consistent moves that eventually broke the equation. We talk about the finance industry’s myths (no, you are not beating the market), why sharing your story works even when you think you’re “not that person,” how giving away thousands of books became a growth engine, and why content creation...

In this conversation with entrepreneur and outsourcing leader Carmen Williams , we unpack the moment she walked into work, felt a physical “no” in her stomach, and quit her job that same day . No plan, no runway, no strategy deck—just bravery born from clarity. This episode isn’t about hustle culture. It’s about permission —to pivot, to shrink your life, to rebuild your identity, and to stop perfo...

In this episode, we use cybersecurity as a lens to expose a truth that every leader forgets: the biggest threats to your company are the ones you can’t see—until they take you down. Scott’s career mirrors the evolution of tech itself—from software stores in the ’80s to early network integration, to building one of the original managed services models before “MSP” was even a phrase. His latest book...

Most founders want a hack. Most apps promise a shortcut. But the fundamentals haven’t changed in 300,000 years: sleep deeply, hydrate, eat real food, and lift heavy things. This episode dismantles the fantasy that “more tech = more health,” exposes why busy executives burn out even with expensive tools, and reframes fitness as relationship-based, not software-based. We dig into why high achievers...

Most people think leadership is about having answers. In reality? AI already has those. The leaders who win next are the ones who know how to ask better questions. In this episode, Luciana and I trace the evolution from old-school hierarchy (titles, power, layers, politics) into something flatter, peer-driven, and choice-based — where people follow you because they want to, not because they “repor...

In a world obsessed with hacks and mindset quotes, Sahil breaks down what actually builds momentum — consistent execution . Doug and Sahil explore how founders can use AI tools to automate busywork without losing the human edge, and why showing up every day — even when no one’s watching — still beats every algorithm. This episode dives into the difference between mindset fluff and measurable actio...

Leadership expert and author Morag Barrett joins Doug Utberg to challenge the myth that “real connection means keeping the peace.” Together they unpack why the best teams — and the strongest friendships — aren’t the ones that avoid conflict, but the ones that use it to grow stronger. Morag, founder of SkyTeam , shares how two decades of leadership research revealed a truth few executives want to h...

Employment attorney Gary Martoccio joins Doug Utberg to unpack how artificial intelligence is rewriting the rules of work — and where the law hasn’t caught up yet. From layoffs driven by automation to courts banning AI-written pleadings, Gary breaks down how fast this shift is moving and what workers need to know before they sign a severance package. Doug and Gary explore how fear, efficiency, and...

We explore how avoidance, disguised as politeness, slowly erodes trust — and how courageous conversations can actually strengthen relationships and performance. Katherine breaks down what “calling out the elephant” looks like in practice: reading the emotional landscape, choosing timing over impulse, and speaking truth without weaponizing it. From emotional intelligence to communication frameworks...

Sue spent years leading high-performing teams in New York City’s recruitment world. Then came burnout, long commutes, and layoffs. With a newborn and a toddler at home, she decided to stop building other people’s companies and start her own. In this episode, we unpack what it really takes to pivot from paycheck to purpose — fear, patience, and the discipline to design a life around freedom, not fr...

Executive coach and researcher Marina Morgan (Morgan Impact) joins me to explore what few founders talk about openly— entrepreneurial trauma —and how resilience, not hustle, becomes your survival skill in an age of constant disruption. Marina works with leaders to navigate emotional recovery after layoffs, bankruptcies, and burnout—real losses that rarely get social support. Together we unpack how...

Originally from Uruguay and now based in Madison, WI, Matias helps cities and organizations connect with underheard voices. He reminds us that progress isn’t just technological—it’s social. Without infrastructure, access, and inclusion , adoption doesn’t happen. EVs, he argues, are a mirror for how we build systems: Who benefits, who’s left out, and who gets a say? TL;DR * Equity first: EV access...

In an era where “understanding everyone’s feelings” often replaces holding standards, Andrew and I unpack how good intentions can quietly corrupt outcomes. The conversation cuts through the noise of soft leadership to reveal a tougher truth: empathy without clarity creates confusion, resentment, and burnout. We trace how businesses drift from mission to maintenance, how leaders lose edge trying to...

Most founders think ads are the only scalable way to grow. They aren’t. Aiden shows how outbound, done right, can outperform paid social—no algorithms, no ad bans, no CPM spikes. The secret isn’t “more hustle.” It’s smarter tech: parallel dialing that filters bad data, avoids spam flags, and connects live calls 10x faster. We trace the fall of traditional cold calls (three live connections per hun...