Second Life Leader

Doug Utberg

From Setback to Success – Second Life Leader tells founder stories of rebuilding companies and leading teams through challenge and change I’m Doug Utberg, and this platform is for founders, rebuilders, creatives, and professionals who’ve been knocked down by layoffs, divorce, burnout, or failure—and still refuse to quit. Each episode delivers raw, unsanitized conversations with leaders who’ve walked through fire, rebuilt from nothing, and now lead with clarity, presence, and conviction. We talk: Career reinvention and self-leadership Burnout recovery and nervous system rebuilding Ethical entrepreneurship and post-collapse strategy Using AI and automation to reclaim time and sovereignty This isn’t a show about playing nice. It’s about building something that can’t be taken from you. 📩 Want to go deeper? The podcast sparks the rebuild— But the newsletter is where the real work happens. Subscribe at DougUtberg.com for weekly strategies, frameworks, and fire-tested insight to help you reclaim your time, rebuild your edge, and lead with sovereign clarity. www.dougutberg.com

  1. 1H AGO

    The Art of the Ask: Outcome-Based Conversations & Smarter Negotiation with Saad A Saad

    Negotiation coach and author Saad A Saad joins Doug to rethink what “the ask” really means—why win-win isn’t always wise, how to thrive even with less power, and why tension isn’t the enemy but the spark of creativity. Most people think negotiation is stressful or adversarial. But Saad reframes it as an outcome-based conversation—something we’re all in daily, whether with clients, colleagues, or family. We dive into why “dominate or be dominated” is outdated, how over-indexing on win-win kills creativity, and why the real skill shows when you’re negotiating from a power disadvantage. Saad also shares his framework from In the Lead: Mastering Your Sales Negotiation—a six-principle model that balances assertiveness and empathy like the two wheels of a bike. TL;DR * Negotiation = outcome-based conversation—happens every day, not just in boardrooms. * Win-lose damages trust, but pure win-win leads to weak, uncreative outcomes. * Power imbalances matter less than you think—focus on clarity of outcome. * Tension and friction aren’t threats—they’re the conditions for respect and innovation. * Assertive empathy: be ambitious in your ask and genuinely curious about the other side. * Context is king: sales, hostage talks, and family dinners require different tools. Memorable lines * “Anytime you’re trying to reach an outcome, you’re in a negotiation.” * “If you over-index on win-win, you become less ambitious and less creative.” * “Friction isn’t failure—it’s the fuel for better outcomes.” Guest Saad A Saad — Negotiation expert, sales coach, and author of In the Lead: Mastering Your Sales Negotiation. LinkedIn: https://www.linkedin.com/in/saadasaad/ Why this matters Whether you’re closing a deal, pitching an investor, or discussing chores at home, negotiation is everywhere. Reframing it as outcome-based—and learning to balance advocacy with empathy—lets you push for better results without burning bridges. Don’t just “hope” your conversations land—design them. Grab Saad’s book In the Lead on Amazon, connect with him on LinkedIn, and the next time you’re in a negotiation—big or small—practice assertive empathy. Book: https://a.co/d/6AkbgX3 Call To Action If this hit—don’t scroll past it. Take the Second Life Leader Quiz to see where you’re powerful, where you’re blocked, and what to do next: leaderquiz.app. Then share this with one man who’s rebuilding. https://leaderquiz.app This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.dougutberg.com

    19 min
  2. 1D AGO

    Hierarchies, Heart-Centers, and Why Community Beats the McMansion

    Retired social worker Jack Kammer (MaleFriendly Media) joins me to separate real men’s issues from the manosphere circus—and map a sane path forward. Most conversations about men mistake the pyramid for the whole picture. Yes, a few at the top feast—but millions grind at the bottom. In this episode, retired social worker Jack Kammer and I dismantle lazy patriarchy takes, unpack mating market math (power laws, hypergamy, real options vs imagined ones), and contrast male hierarchy with the female network—a “heart-centered” power structure that’s present but hard to see. We trace how wealth-induced social isolation (sprawl, cars, planned hangouts) erodes trust, why “work-life balance” collapses under the burden of performance, and how honesty about desire, capacity, and family roles beats quota-based fantasies. The fix isn’t rage—it’s community at Dunbar scale, merit with compassion, and finishing the other half of the gender-role revolution: giving men social permission for relationship labor, not just income labor. No villains. Just truth, trade-offs, and a way to rebuild. TL;DR * Apex fallacy: don’t judge men by the 0.1%—see the “Misfortune Five Million.” * Two power systems: men = visible hierarchy; women = diffuse heart-centered network. * Isolation tax: the McMansion dream kills accidental community—connection needs proximity. * Work is not separate from life: entrepreneurs blur lines; corporate men carry the performance burden. * Real reform: finish the 1960s shift—normalize men taking relationship/care roles without penalty. * Strategy > slogans: meritocracy plus flexibility; transparency about intentions in dating and at work. Memorable lines “Don’t look at the Fortune 500—look at the Misfortune Five Million.”“The female power structure isn’t a skyscraper; it’s a campus with a heart at the center.”“Community isn’t a social program; it’s your neighbors knocking for Friday pizza.” Guest Jack Kammer — Retired social worker focused on the social issues of men and boys; founder of MaleFriendly Media. https://www.linkedin.com/in/malefriendlymedia/ https://www.malefriendlymedia.com/ Why this matters If you want stronger men, healthier women, and better kids, stop arguing abstractions and design for reality: smaller, closer communities; honest courtship; flexible pathways for fathers; merit with compassion at work. Call to Action If this hit—don’t scroll past it. Take the Second Life Leader Quiz to see where you’re powerful, where you’re blocked, and what to do next: leaderquiz.app. Then share this with one man who’s rebuilding. https://leaderquiz.app This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.dougutberg.com

    58 min
  3. SEP 7

    Reinventing your Life with Damon Lembi

    This week I sit down with Damon Lembi, a man who once stood on the edge of a pro baseball career, only to watch that dream disappear in his early 20s. What followed was not the straight-line success story that corporate planners love to sell—but the messy, real work of reinvention. We go deep on: * Why life almost never moves in a straight line—and why that’s a gift, not a curse * How failure is fuel, not a flaw * The transferable skills that carry you from one arena to another * Why vulnerability paired with confidence is the mark of a true leader * The difference between safe, compounding plans and the resilience forged through risk and reset Damon’s story isn’t about baseball. It’s about every man or woman who’s looked up from the ashes of one path and wondered if they had the courage to start another. If you’ve been burned by the old game—but your fire still burns—this conversation will remind you: you are not finished. You’re being reforged. ⚒️ Listen in, then share it with someone who’s rebuilding. And if you want to follow the thread deeper, head to DougUtberg.com for my Second Life Leader newsletter—where we talk leadership, sovereignty, and the art of building a life that cannot be taken from you. Freedom isn’t granted. It’s forged. Connect with Damon: www.learnit.com https://www.linkedin.com/in/damonlembi Subscribe to Second Life leader at https://dougutberg.com This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.dougutberg.com

    24 min
  4. AUG 11

    A Business That's Built to Buy with John Knowlton

    Second Life Leader is where burned-out high achievers come to rebuild—not retreat. I’m Doug Utberg, former corporate soldier turned sovereign strategist. If the old game broke you but didn’t kill your fire, you’re in the right place. In this episode, I’m joined by John Knowlton, a veteran of 20+ mergers and acquisitions, to unpack the real playbook for buying and scaling businesses without sinking in chaos. We break down: * The three core reasons to acquire—same offering, new geography, or expanded services * Why small- and mid-sized businesses are often better M&A targets than big-ticket corporate buys * How to spot “total chaos” deals you can turn into gold with simple best practices * The invisible layer of management most founders miss when they double in size * The truth about integration—why it’s messier (and more decisive) than negotiation Whether you’re a first-time buyer or building a portfolio of companies, this conversation will sharpen your lens for growth by acquisition—and help you avoid the traps that kill most deals. Listen in, take notes, and remember: freedom isn’t granted. It’s forged. Connect with John:https://www.linkedin.com/in/john-knowlton-516b828/ https://AbundantThoughtRevolution.com Subscribe to the Second Life Leader Podcast & Newsletter: https://dougutberg.com This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.dougutberg.com

    26 min
  5. AUG 1

    Work Life Harmony with Lindsay Barnett

    What if “work-life balance” was the wrong question? In this electrifying episode of Second Life Leader, Doug Utberg sits down with executive coach and former Fortune 500 insider Lindsay Barnett to dismantle the productivity cult and offer something radically more powerful: work-life harmony. This isn’t another burnout sob story. It’s a tactical reframe for warriors, rebuilders, and sovereigns ready to stop apologizing for wanting more—and start structuring their life around energy, not just time. Inside this episode: * Why “busy” has become a socially sanctioned addiction—and how to detox from it * The 3 Energetic Levers: Creative, Connection, and Completion Energy (this framework alone is worth the listen) * How to build presence into your workflow without pretending your inbox doesn’t exist * Why work-life balance is a corporate myth—and how real leaders orchestrate their days like symphonies, not spreadsheets * Doug’s personal ritual of sovereignty: baking bread, brewing kombucha, and anchoring presence through food Lindsay brings decades of high-level HR and coaching wisdom, but this isn’t corporate fluff. It’s a blueprint for reclaiming your day, your energy, and your soul—without waiting for someone else to give you permission. 🔗 Listen now and reclaim your rhythm. 🛠️ Resources + Links * Lindsay’s tools: https://workinghelltoworkingwell.com * Doug’s newsletter on sovereignty + reinvention: https://dougberg.com * Connect with Lindsay: https://barnettcoaching.com | LinkedIn 🧨 If you're still trying to “balance” your life, you're already losing. Harmony is the new sovereignty—and it starts here. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.dougutberg.com

    26 min
4.9
out of 5
33 Ratings

About

From Setback to Success – Second Life Leader tells founder stories of rebuilding companies and leading teams through challenge and change I’m Doug Utberg, and this platform is for founders, rebuilders, creatives, and professionals who’ve been knocked down by layoffs, divorce, burnout, or failure—and still refuse to quit. Each episode delivers raw, unsanitized conversations with leaders who’ve walked through fire, rebuilt from nothing, and now lead with clarity, presence, and conviction. We talk: Career reinvention and self-leadership Burnout recovery and nervous system rebuilding Ethical entrepreneurship and post-collapse strategy Using AI and automation to reclaim time and sovereignty This isn’t a show about playing nice. It’s about building something that can’t be taken from you. 📩 Want to go deeper? The podcast sparks the rebuild— But the newsletter is where the real work happens. Subscribe at DougUtberg.com for weekly strategies, frameworks, and fire-tested insight to help you reclaim your time, rebuild your edge, and lead with sovereign clarity. www.dougutberg.com