Pivotal With Kevin Simcock

Kevin Simcock
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Pivotal with Kevin Simcock is a podcast for former executives, exited founders, and senior leaders navigating the space after success, when the title is gone and the question becomes personal: what’s next, and who am I now? Each episode blends emotional truth with practical clarity. Kevin shares lived experience and real-world insight on identity loss after exit, rebuilding self-authority, and creating a next chapter that feels aligned, not performative. This is not hustle advice or surface-level motivation. It is a grounded, honest look at the inner patterns that shape your decisions, especially under pressure. If you are in a career transition, post-exit reinvention, leadership reset, or “dog off the leash” moment, Pivotal gives you language, perspective, and a steady decision filter for building a legacy that reflects who you actually are. Based in Toronto, Canada, and working with leaders across North America and globally, Kevin brings decades of global leadership experience and a mentorship approach built on pattern recognition, truth-testing, and decisive focus. Topics include: executive transition, founder exit, identity disruption, self-authority, purpose, burnout recovery, redefining success, leadership under pressure, and building what’s next with clarity and momentum. Visit www.kevinsimcock.com for more info.

  1. New Beginnings: Building What's Next After Pivotal Transitions in Life

    JAN 27

    New Beginnings: Building What's Next After Pivotal Transitions in Life

    In this episode of Pivotal with Kevin Simcock, we are talking about new beginnings, and why they rarely feel like a fresh start at first. More often, they feel like an ending that left you standing in a quiet room with an empty calendar and a loud question: Who am I without the role? If you are a former executive, exited founder, or senior leader in transition, you might know the “dog off the leash moment.” The structure is gone. The title is gone. The pace that used to define you is gone. What is left is you, and the opportunity to build what’s next from truth instead of pressure. In this conversation, I share personal stories and the inner shift that changed everything for me: identity decoupling, reclaiming self-authority, and choosing a legacy after exit that actually feels like yours. Not the version that looks good on paper, but the one you can live with. You will leave with a grounded reflection you can use today:  Six months from now, what do you want to be true about you? What is one behaviour you will start today to build it, and one behaviour you will stop because it belongs to the old version of you? If this episode strikes a chord, share it with someone who might need it. And if you are navigating a career transition, executive exit, or founder reinvention and want support building what’s next, you can find me at kevinsimcock.com. ----- Purchase Kevin Simcock’s Book: Whose ladder Is This? Available on Amazon Kindle, paperback and hardcover HERE Interested in working with Kevin visit kevinsimcock.com for more information.  Check out more episodes of Pivotal: http://www.youtube.com/@KevinSimcock-Pivotal Host: Kevin Simcock  LinkedIn Profile https://linkedin.com/kevin-simcock

    26 min

  2. 2025-12-11

    Scaling You: The Inner Work Founders Must Consider to Grow Their Business

    Your business isn’t stalled because of your systems, team, market conditions, or even strategy. It’s stalled because of something far more uncomfortable. Something most leadership advice completely misses. You. In this episode of Pivotal, I break down the hidden force driving every decision, every bottleneck, every high-stakes moment in your business: your identity as a founder. Not the role. Not the title. The real you behind it. The version of you that shows up under pressure, risk and uncertainty. Most founders follow leadership advice built for corporations with layers of protection. But you don’t have that luxury. You are the business, which means your beliefs, fears, patterns and blind spots are either accelerating growth or quietly killing it. This episode digs into:  • The biggest leadership mistake founders make without knowing it  • Why your identity shapes revenue more than your strategy  • How control, fear and avoidance sabotage growth from the inside  • Real-world examples of leadership patterns that cost companies millions  • What actually changes when a founder evolves into the leader their next stage demands If you’re staring at a growth plateau, wondering what’s really going on, this conversation will give you a clear answer. And it might not be the answer you expected. This is the work that separates founders who scale from those who stall. Tune in, get honest, and see what version of you your business has been waiting for. Purchase Kevin Simcock’s Book: Whose ladder Is This? Available on Amazon Kindle, paperback and hardcover HERE Sign up to work with Kevin to see how he can help you and your business - https://www.kevinsimcock.com/partnershiprequest    Check out more episodes of Pivotal: http://www.youtube.com/@KevinSimcock-Pivotal Host: Kevin Simcock    LinkedIn Profile https://linkedin.com/kevin-simcock

    20 min

  3. 2025-11-19

    The Most Expensive Leadership Mistake: Leading From Misalignment

    When your business looks successful but feels off, something deeper is happening.  In this episode, Kevin breaks down one of the most expensive leadership mistakes: leading from misalignment. He shares how even high-performing founders lose clarity, why it stalls growth, and the simple steps that help you get unstuck and rebuild momentum.  If you have felt off but cannot explain why, this episode will hit home. Purchase Kevin Simcock’s New Book: Whose Ladder Is This? Available on Amazon Kindle, paperback and hardcover HERE In Whose Ladder Is This?, former global executive and creative strategist Kevin Simcock shares a raw, honest account of what happens when achievement no longer aligns with identity. After building billion-dollar brands and leading teams across continents, Kevin found himself furloughed at fifty, disconnected from his former self and unsure of what was next. That loss cracked open something deeper, the need to redefine success and realign with what truly matters. Part memoir, part guidebook, this is not a story of burnout or breakdown. It’s a story of awakening. Through vulnerable storytelling, insight-rich reflection, and hard-won clarity, Kevin walks you through the messy but necessary process of letting go of who you thought you had to be, so you can step into the version of yourself that was waiting all along. If you’re a successful business owner or career professional at a turning point, wondering what comes after the climb, this book will help you reconnect with your inner truth, trust your next chapter, and build a life that actually feels like yours. Schedule a FREE 15 min consultation call with Kevin to see how he can help you and your business - https://www.kevinsimcock.com Check out more episodes of Pivotal: http://www.youtube.com/@KevinSimcock-Pivotal Host: Kevin Simcock  LinkedIn Profile https://linkedin.com/kevin-simcock

    21 min

  4. 2025-08-14

    From Exit to Alignment: The Real Work of Finding What’s Next

    You’ve stepped away from the corporate career or business you built over decades. The title, the structure, the recognition—they’re behind you. Now you’re facing the question that matters most: What’s next? In this episode of Pivotal, Kevin Simcock shares how to navigate this transition with clarity, purpose, and direction. You’ll learn how to shed the old identity that no longer fits, uncover your core values, and use them as a filter for every decision in your next chapter. Discover why fulfillment—not just outward success—is the key to building a business and life you actually want to live. Whether you’re a former executive, business owner, or senior leader in transition, you’ll take away practical reflection prompts and real-world insights to help you move forward with confidence. Start from the right place—who you are now—and build a rewarding business and a fulfilling life. Schedule a FREE 15 min consultation call with Kevin to see how he can help you find what's next - https://www.kevinsimcock.com/service-page/intro-discovery Check out more episodes of Pivotal: http://www.youtube.com/@KevinSimcock-Pivotal Host: Kevin Simcock  LinkedIn Profile https://linkedin.com/kevin-simcock

    14 min

  5. 2025-06-19

    What Fulfillment Really Looks Like (Beyond Success & Burnout)”

    Spoiler: it’s not a French villa, a gold watch, or a bigger business. If you’ve built success that looks great on the outside but secretly feels exhausting, disconnected, or empty this final episode of The Clarity Series is for you. Whether you’re leading a fast-scaling business or navigating the weight of past success, you’ll learn: ·      The illusion of “more” that leads to burnout ·      What true fulfillment feels like (and how to recognize the signs) ·      The silent costs of staying misaligned ·      Why your business is a vehicle not your identity ·      Simple steps to reconnect with what really matters without blowing everything up If you’re ready to build a business and life that actually feels good again, clarity starts here. Subscribe for more leadership clarity, purpose-driven growth, and fulfillment at the top: http://www.youtube.com/@KevinSimcock-Pivotal Schedule a FREE 15 min consultation call with Kevin: https://www.kevinsimcock.com/service-page/intro-discovery Sign up for THE FIX newsletter: kevinsimcock.com

    35 min

  6. 2025-06-17

    The Hidden Cost of Leading Without Clarity | Why Misaligned Leadership Fails

    Your team mirrors your leadership. So if you’re misaligned they feel it. In this episode of The Clarity Series, I break down what really happens when leaders operate without clarity and why it’s the #1 reason culture collapses, progress stalls, and your best people check out. You’ll learn: The invisible ways unclear leadership sabotages team performanceHow misalignment at the top quietly spreads across your businessA simple “Leadership Mirror” exercise to identify where you might be the bottleneck5 actionable steps to regain clarity, focus, and momentumThis isn’t about adding another strategy deck. It’s about looking inward because your next level of leadership starts with you. If you’ve built real success but it’s costing you more than it should, this episode is for you. –––  ABOUT ME I’m Kevin Simcock, a strategic growth advisor and former global ad exec helping high-performing founders realign with what matters—so they can scale with clarity, energy, and purpose. –––  Ready to get clear and lead better? Reach out at https://www.kevinsimcock.com/or DM me on LinkedIn. ––––  Subscribe for more leadership clarity, brand strategy, and mindset alignment content.

    16 min

  7. 2025-06-11

    You’re Not Burnt Out—You’re Misaligned (The Truth About Hustle Culture)

    What if your exhaustion isn’t from doing too much—but from doing the wrong things? In this episode of Pivotal, I challenge one of the most toxic beliefs in business: that success requires constant hustle. If you're a founder or leader running at full speed but still feeling off… this is the reset you didn’t know you needed. We’ll break down: Why hustle masks deeper misalignmentThe real cost of chasing success without clarityHow internal alignment unlocks sustainable momentumPractical steps to shift from force to flow—without losing your edgeIf you’ve achieved the success you thought would fulfill you—but something still feels missing—this conversation will hit home. Subscribe for more real talk on conscious leadership, clarity, and redefining success on your own terms. Schedule a FREE 15 min consultation call with Kevin to see how he can help you and your business - https://www.kevinsimcock.com/service-page/intro-discovery Sign up for THE FIX newsletter for more exclusive strategies, insights and frameworks to grow your business at kevinsimcock.com Check out more episodes of Pivotal: http://www.youtube.com/@KevinSimcock-Pivotal Host: Kevin Simcock  LinkedIn Profile https://linkedin.com/kevin-simcock

    18 min

  8. 2025-06-06

    You've Evolved But Your Business Hasn't. Now What?

    You built the dream—but now it feels like a trap. If your successful business no longer fits who you've become, it’s not a sign of failure; it’s an invitation to evolve. In Episode 2, we explore the critical moment many purpose-driven founders experience when they realize they've outgrown their original business vision. We'll dive deep into: ·       Recognizing the signs that you’ve outgrown your business. ·       Understanding why founders often resist necessary change. ·       Practical strategies to courageously reimagine your next chapter. ·       How embracing reinvention leads to deeper clarity, purpose, and fulfillment. Ready to reinvent—not retreat? 🔹 SUBSCRIBE to the channel for insights to help you lead a more purposeful, fulfilling life. 🔹 CONNECT Schedule a FREE 15 min consultation call with Kevin to see how he can help you and your business - https://www.kevinsimcock.com/service-page/intro-discovery Sign up for THE FIX newsletter for more exclusive strategies, insights and frameworks to grow your business at kevinsimcock.com Check out more episodes of Pivotal: https://podcasts.apple.com/ca/podcast/nifty-thinking/id1680610153  Podcast NOW on YOUTUBE!! - https://www.youtube.com/@KevinSimcock-Pivotal Host: Kevin Simcock  LinkedIn Profile https://linkedin.com/kevin-simcock

    23 min
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Trailer

About

Pivotal with Kevin Simcock is a podcast for former executives, exited founders, and senior leaders navigating the space after success, when the title is gone and the question becomes personal: what’s next, and who am I now? Each episode blends emotional truth with practical clarity. Kevin shares lived experience and real-world insight on identity loss after exit, rebuilding self-authority, and creating a next chapter that feels aligned, not performative. This is not hustle advice or surface-level motivation. It is a grounded, honest look at the inner patterns that shape your decisions, especially under pressure. If you are in a career transition, post-exit reinvention, leadership reset, or “dog off the leash” moment, Pivotal gives you language, perspective, and a steady decision filter for building a legacy that reflects who you actually are. Based in Toronto, Canada, and working with leaders across North America and globally, Kevin brings decades of global leadership experience and a mentorship approach built on pattern recognition, truth-testing, and decisive focus. Topics include: executive transition, founder exit, identity disruption, self-authority, purpose, burnout recovery, redefining success, leadership under pressure, and building what’s next with clarity and momentum. Visit www.kevinsimcock.com for more info.

Information

  • Creator
    Kevin Simcock
  • Years Active
    2023 - 2026
  • Episodes
    36
  • Rating
    Explicit
  • Copyright
    © 2026 Pivotal With Kevin Simcock
  • Show Website
    Pivotal With Kevin Simcock