The Dwayne Kerrigan Podcast

The Dwayne Kerrigan Podcast

Welcome to The Dwayne Kerrigan Podcast. Dwayne has navigated the business world for over 35 years, owning close to 30 businesses in 12 distinct industries. Today, entrepreneurship often seems more about glitz, glamour, and a celebrity venture. On this podcast, Dwayne collaborates with overlooked but accomplished entrepreneurs, delving into their journeys of forging exceptional enterprises. Join them as they share their personal journeys, lessons learned, and strategies that keep them moving forward. Let’s celebrate the true essence of entrepreneurship and inspire the next wave of business trailblazers.

Episodes

September 3, 2025 52 mins

In Part 2 of his inspiring conversation with Dwayne Kerrigan, Jason Castellan, Co-Founder & CEO of Skyline Group of Companies, goes beyond the growth story to share his philosophy on leadership, risk, and building a multi-generational business.

Jason opens up about succession planning, why staying people-focused is Skyline’s greatest advantage, and how he balances growth with responsibility to over 1,000 employees and 6,000 inve...

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    In this powerful first part of a two-part conversation, Dwayne Kerrigan sits down with longtime friend and business leader Jason Castellan, Co-Founder & CEO of Skyline Group of Companies.

    Jason shares how growing up in small-town Walkerton, Ontario, instilled humility, resilience, and a relentless work ethic that carried him from hockey rinks and hayfields to co-founding one of Canada’s most respected real estate investment firm...

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    In this deeply personal second half of their conversation, Dwayne Kerrigan and Alvin Brown explore the power of unconditional love, the legacy of strong relationships, and how to face unimaginable loss with grace.

    Alvin shares the philosophies and daily disciplines that helped him navigate the devastating passing of his son, Cammie, after a courageous battle with cancer. From being a “lighthouse in the storm” for his family, to buil...

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    In this powerful 100th episode, Dwayne Kerrigan sits down with long-time friend and high-performance coach Alvin Brown to explore the mindset, resilience, and relentless curiosity that transformed Alvin’s life. From his early days as a Jamaican immigrant living in poverty, to his evolution as an elite therapist for world-class athletes, Alvin shares the turning points, challenges, and mindset shifts that fueled his journey.

    They div...

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    Four-time Olympian, two-time gold medalist, World Rugby Hall of Famer and high-performance coach Heather Moyse returns to The Dwayne Kerrigan Podcast for a transformative conversation on sustainable success. In this energizing episode, Heather and Dwayne explore what it really means to thrive—from corporate burnout and high performance to the true essence of recovery, clarity, and fulfillment.

    Heather breaks down her signature “Podi...

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    In this powerful second installment, Molly Bloom takes us from her lowest point—convicted felon, millions in debt, and under FBI indictment—to the surprising turn that led her back into the spotlight. She shares how the same athletic grit that carried her down Olympic slopes helped her weather mob threats and a RICO case, and ultimately propelled her into publishing a memoir and partnering with Aaron Sorkin to bring Molly’s Game to...

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    In this riveting first installment, Dwayne sits down with Molly Bloom, they trace her journey from a straight-A student and elite mogul skier—who overcame major spinal surgery—to California, where an identity crisis set her on an unexpected path into the world of high-stakes underground poker. Along the way, Molly reflects on the powerful roles family dynamics, honesty, and courage have played in her life. She shares how the pivota...

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    In this unfiltered second half of their conversation, Dwayne Kerrigan and Vaneli Martinov dive deeper into the mindset, systems, and soul behind exceptional operations leadership.

    Vaneli—EVP of Operations for the world-renowned Wellington International—opens up about what it really means to lead from the front lines: managing 500+ seasonal staff, navigating crisis in real-time, and mentoring a team while raising a family.

    From hiring...

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    What does it take to run 500 events across 16 weeks and still make it home for bedtime stories? In this powerhouse episode, Dwayne Kerrigan sits down with Vaneli Martinov, Executive Vice President of Operations for the world-renowned Wellington International.

    Vaneli opens up about the reality behind high-performance leadership—juggling relentless operations, motherhood, and building a career from the ground up. From her early days a...

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    In Part 2 of this masterclass conversation, former Navy SEAL and leadership architect Rich Diviney returns to go deeper into the strategies behind his new book The Masters of Uncertainty—and delivers real, actionable frameworks for leaders who want to scale, perform, and lead better under pressure.

    Dwayne and Rich explore how to literally reduce fear using a neuroscience-backed process called Moving Horizons, how to train your brain...

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    In this powerful first installment of a two-part conversation, former Navy SEAL commander and performance expert Rich Diviney returns to The Dwayne Kerrigan Podcast to discuss his groundbreaking new book, The Masters of Uncertainty.

    With decades of leadership inside one of the world’s most elite military units, Rich unpacks how we can all perform better under pressure, lead with clarity in chaos, and transform anxiety into purposefu...

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    In this dynamic Part 2 episode, entrepreneur and growth strategist Swish Goswami returns to The Dwayne Kerrigan Podcast to explore the cutting edge of AI, data ethics, and leading with intention in an unpredictable world.

    From the growing tension between privacy and innovation to the responsibility of the next generation of creators, Swish unpacks what it takes to thrive in a digital-first era. He also shares actionable strategies f...

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    In this powerhouse Part 1 conversation, Dwayne Kerrigan sits down with Swish Goswami—serial entrepreneur, public speaker, and Head of Growth at Parallel Studios—to uncover what it really takes to build, scale, and sell companies in today’s hyper-evolving landscape.

    From co-founding the data-forward tech company Surf (acquired in 2025), to leading global growth for sci-fi gaming empire Parallel Studios, Swish shares deeply candid ins...

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    In the final installment of our powerful 3-part series, Dwayne welcomes back world-renowned energy healer and spiritual teacher Master Stephen Co for a transformative conversation designed to help high-performing professionals reclaim calm, clarity, and control—especially in the face of emotional chaos.

    This episode is not just a conversation. It’s a clinic.

    Master Co walks listeners through a step-by-step energetic technique to move...

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    In Part 2 of this profoundly moving conversation, Dwayne sits down again with Master Stephen Co—one of the most influential spiritual teachers in Dwayne's life—for a powerful discussion that stretches beyond business and deep into self-awareness, spiritual discipline, and energetic mastery.

    Master Co guides listeners through a short but transformative meditation, unpacks the mechanics of stress and healing through the lens of pranic...

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    In this of The Dwayne Kerrigan Podcast, Dwayne sits down with Master Stephen Co—engineer-turned-global-energy-healer—to discuss how ancient energy healing practices like Pranic Healing® can unlock peak performance, faster recovery, emotional balance, and even business success.

    Dwayne shares intimate stories of miraculous healing, including a shredded ACL recovery in just five days—no surgery required. Together, they challenge skepti...

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    In this powerhouse follow-up episode, Jaime McKenna, President at Fengate Real Estate, returns to unpack the intersection of leadership, housing economics, and strategic foresight in times of uncertainty. She candidly reflects on navigating imposter syndrome, the true nature of financial literacy, and the real estate crisis threatening Canada’s future. From affordable housing and capital flow challenges to why boring businesses oft...

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    In this deeply candid and inspiring Part 1 of their conversation, Dwayne sits down with Jaime McKenna — President of Real Estate at Fengate Asset Management — for a raw, no-filter look at what it takes to go from near-poverty to managing billions. Jaime shares the deeply personal story of losing everything in her university years, climbing out of debt, overcoming imposter syndrome, and redefining leadership in a high-stakes, male-d...

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    In Part 2 of this candid global conversation, Karl Tabbakh returns to The Dwayne Kerrigan Podcast to pull back the curtain on the economic uncertainty that’s gripping both Canada and the U.S.—and what business leaders need to do about it.

    Dwayne and Karl dissect the real cost of tariffs, the psychological divide between the “haves” and “have nots,” and what a future recession could mean for Canadian competitiveness. They challenge l...

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    In one of the most urgent and eye-opening conversation, Dwayne sits down with Karl Tabbakh—top Canadian business strategist, international dealmaker, and former chair of the Canadian Chamber of Commerce—to unpack the global forces redefining the rules of business, politics, and leadership.

    Together, they explore what rising geopolitical tension, fractured trade alliances, and shifting world orders mean for entrepreneurs, CEOs, and d...

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