The Dwayne Kerrigan Podcast

• 102. From Small-Town Roots to $9 Billion in Assets: Jason Castellan’s Journey with Skyline

  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 firms.From his first student rental at the University of Guelph to overseeing $9 billion in assets under management and 1,000 employees, Jason pulls back the curtain on what it really takes to scale a business: financing hacks, the importance of partnerships, knowing when to let go, and why trust and relationships are more valuable than capital.This episode is a masterclass in grit, community-driven leadership, and building wealth with integrity.Timestamps00:00 – The myth of the straight path in business & near-bankruptcy moments01:30 – Introducing Jason Castellan & Skyline’s $9B journey04:00 – Lessons from Walkerton: humility, farming roots & mentorship07:00 – Childhood, hockey dreams, and how sports shaped his competitiveness13:00 – The first student rental at Guelph and early entrepreneurial lessons15:30 – Scaling to 52 houses: financing, sweat equity & creative problem-solving21:00 – Financing strategies: trust, relationships, and building a social network27:00 – Building your own legend: why life outside business matters30:00 – Person vs. story: what investors really buy33:00 – Facing doubt, trust, and learning to scale through partnerships39:00 – Business battles, resilience, and “one more round” perseverance42:30 – Experience creates strategy: when to let go & hire experts46:00 – Leveraging talent: how Skyline attracted top-tier leaders50:00 – Roadshows, raising capital & building Skyline’s REIT structure55:00 – Closing thoughts: responsibility, growth, and investor trustNotable Quotes“Build your legend. Be more than just a businessperson—have stories, have character, have a life that’s interesting to share.” – Jason Castellan“Face-to-face relationships are the currency of real estate—and of business.” – Jason Castellan“I wouldn’t have a fraction of what I have today if it wasn’t for partners.” – Jason CastellanResources & MentionsSkyline Group of Companies → SkylineSkyline Apartment REIT → Learn moreSkyline Industrial REIT → Learn moreSkyline Retail REIT → Learn moreSkyline Clean Energy Fund → Learn moreKey TakeawaysBusiness is never a straight line – resilience and adaptability are everything.Partnerships can multiply success – sweat + equity =...

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• 101. Turning Pain into Purpose with Alvin Brown

  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 building a life with no regrets, Alvin reveals how preparation, consistency, and living intentionally can carry you through life’s hardest moments.This episode is raw, vulnerable, and full of wisdom on parenting, relationships, and turning pain into purpose.Timestamps00:00 – The meaning of life: “Who will cry when you die?”01:00 – Recap of Part 1 and the “one decision away” philosophy02:00 – The good wolf/bad wolf parable and the danger of shame05:00 – Parenting with love, freedom, and minimal shaming06:30 – The role of unconditional love and the lack of strong male role models10:00 – Lessons from disappointing mentors14:00 – How unconditional love from his mom shaped Alvin’s resilience18:00 – Avoiding mistakes of past male role models in marriage and parenting20:00 – The blow of losing Cammie and how preparation meets tragedy23:00 – Building life around family to avoid future regrets26:00 – Cammie’s rare cancer diagnosis and courageous fight32:00 – No regrets: being there for every moment36:00 – Processing grief without suffering40:00 – Earning love and respect daily43:00 – Late-night talks with Cammie about fear and life46:00 – Disassociating from the disease to focus on the person48:00 – Creating stability and predictability during chaos52:00 – Rituals, habits, and consistency as anchors54:00 – Turning pain into purpose through Cammie’s foundation57:00 – The unexpected generosity and support from friends and community58:30 – The impact of being present in your children’s lives1:00:00 – Life lessons: courage, clarity, commitment, and consistency1:03:00 – Closing reflections on living a life with no regretsNotable Quotes“I can’t fail—my mom’s always got my back.” – Alvin Brown“Be the lighthouse in the storm.” – Alvin Brown“Love and respect aren’t given; they’re earned every day.” – Alvin Brown“I’m going through grief, but I’m not suffering—because I have no regrets.” – Alvin Brown“Life consistently requires courage—to live and to die.” – Alvin Brown“I want to be sad that I’ll miss you, not sad that you didn’t live.” – Alvin BrownValuable Resources & TakeawaysFeed the Right Wolf – Focus on nurturing the behaviors and thoughts that align with your values.Avoid Shame-Based Parenting – Love and encouragement produce more change than guilt.Unconditional Love as a Foundation – Creates the resilience to take risks and recover from failure.Preparation is Key – In crisis, you default to your level of training and discipline.Life Design – Build work around your life, not the other way around, to prevent future regrets.Predictability in Chaos – Habits and routines create stability during life’s...

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• 100. One Decision Away: Resilience, Curiosity & Building a Life of Purpose with Alvin Brown

  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 dive deep into the value of sport as a springboard for confidence and self-worth, the discipline of constant learning, and the life-changing power of creating space between stimulus and response. Packed with raw honesty and hard-earned wisdom, this episode is a masterclass in perseverance, personal mastery, and living intentionally.Timestamps00:00 – “Don’t get through it, get from it” – Alvin’s core life philosophy01:00 – Dwayne introduces Alvin Brown and their 25+ year friendship02:00 – Alvin’s immigration from Jamaica and early years in poverty04:30 – Resilience born from cultural shifts and adversity05:30 – Becoming one of the top massage therapists and constant learning06:30 – Building The Centre for Healing and Peak Performance & writing his book07:00 – Role modeling long-term relationships and perseverance09:00 – Alvin’s early ambitions in wrestling, martial arts, and boxing13:30 – Lessons from sport: confidence, belief, and self-worth15:30 – The Olympic dream as legitimacy and identity18:00 – The chance encounter in Cuba that led to a career in therapy20:00 – Going from a “D for diploma” student to top marks in massage school22:00 – Stacking skills: nutrition, acupuncture, energy work, osteopathy30:00 – The importance of energy, intention, and integrative health31:00 – Overcoming the “no degree” weakness and earning a psychology degree33:00 – Studying NLP and the lifelong practice of mindset mastery35:00 – Curiosity as a driver and eliminating perceived weaknesses40:30 – One decision away – pivotal moments in parenting and relationships45:00 – Creating space between stimulus and response to make better decisions51:00 – The role of introspection and honest mentorship55:00 – Lessons in ego, business building, and staying true to your gifts59:30 – Why asking “why” matters – and when it doesn’t1:02:00 – Understanding that “greatness” is different for everyone1:03:00 – Preview of Part 2: handling loss and becoming a lighthouse for othersNotable Quotes“Don’t get through it, get from it.” – Alvin Brown“You’re always one decision away from turning up or turning down the trajectory of your life.” – Alvin Brown“Sport gave me confidence, belief, and self-worth—and that became my springboard.” – Alvin Brown“The space between stimulus and response is where mastery lives.” – Alvin Brown“I don’t seek to be smart; I seek to be wise.” – Alvin Brown“Sometimes you’re driving the right vehicle on the wrong road.” – Dwayne KerriganValuable Resources & TakeawaysThe Power of Sport – Organized sports teach goal-setting, resilience, teamwork, and how to come back from loss.Stack Your Skills – Keep adding complementary knowledge (nutrition, energy work, mindset training) to create a unique...

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• 99. The Champion Mindset: Thriving with Heather Moyse

  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 “Podium Process”—a framework for shifting from autopilot to intentional mastery. With humour, honesty, and Olympic-level insight, she shares how to move from societal expectations to personal values, how to reframe setbacks, and how to redefine balance on your own terms.This isn’t just about peak performance. It’s about purpose-driven living—without sacrificing your wellbeing.Timestamps:00:00 – Welcome back, Heather Moyse01:30 – What Heather’s been working on: new keynotes and multiple book ideas04:00 – Introducing “The Champion Mindset” and what sets it apart06:45 – Mindset shifts: thriving > extreme productivity09:15 – Corporate vs. athletic performance parallels11:00 – Heather’s “Podium Process”: Dream, Plan, Pursue, Perform13:30 – Self-sabotage and moving through internal blocks17:00 – Recovery ≠ rest: the burnout epidemic explained19:15 – Micro, Meso & Macro Recovery in sport and business22:00 – Why “one step back, two steps forward” is a strategic power move27:00 – Root Why vs. Surface Goals: questions that clarify your true path33:00 – Gender differences in burnout and balance38:00 – Self-sabotage, people-pleasing, and the fear of judgment42:00 – Why clarity requires disconnection from the noise45:30 – Heather’s own mindfulness & recovery practices51:00 – What propels forward movement and momentum55:00 – From High Performance to Mastery (Dwayne’s mindset shift)57:30 – Final thoughts + where to connect with HeatherNotable Quotes:“People don’t need to feel guilt and shame for not doing all the things social media tells us to do.” — Heather Moyse“Burnout isn’t from too much work—it’s from too little recovery.” — Heather Moyse“You can’t feel fulfilled when you’re living a life aligned with someone else’s values.” — Heather Moyse“We’re more committed to recharging our phones than ourselves.” — Heather MoyseResources & Mentions:Heather Moyse Website https://www.heathermoyse.com/Book: Redefining Realistic by Heather MoyseInstagram: @heathermoyseListen to Heather’s first episode on the Dwayne Kerrigan Podcast:https://open.spotify.com/episode/5Uw17Z9M6WXq8H5LmFBy9Y?si=32ySJBUWTSm-XyqtO9GlQwhttps://open.spotify.com/episode/7cHwtyjwQ1LC3dgJA8W48k?si=OOtCOvU2QIeIfRVuemh2lw Key Takeaways:High performance is not sustainable without intentional recovery built into your system.The Podium Process (Dream → Plan → Pursue → Perform) is a customizable roadmap for fulfillment.Clarity requires space—true insight only comes when you step back from the noise.Reframing setbacks is a skill—one that separates people who grow from those who...

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• 98. Molly Bloom’s Redemption: From Federal Felon to Oscars Night

  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 the big screen. Along the way, Molly reveals the hard lessons of maintaining integrity under pressure, the freedom found in losing everything, and the resilience required to rewrite your own story. She also opens up about balancing motherhood with newfound opportunities, her unlikely journey through Hollywood, and the personal triumph of starting a family against all odds. Timestamps00:00 – Rock Bottom Reveal: From poker queen to convicted felon in millions of debt01:00 – Athletic Grit, Part II: How Olympic lessons powered Molly’s comeback02:30 – Motherhood vs. Ambition: Battling mom-guilt, building your support “village,” finding stillness07:00 – Rewriting the Rulebook: From burnout to a recovery toolkit of meditation, rest & self-compassion10:00 – Integrity Under Fire: Turning down the easy plea and standing by your values12:00 – The Mob, the Gun, the Mirror: Surviving extortion and confronting your moral drift16:00 – Indictment & Advocacy: Choosing transparency with federal prosecutors over plea-bargain fame20:00 – Betting on a Story: From a 10-copy book launch to winning Aaron Sorkin’s Hollywood trust24:00 – From Courtroom to Red Carpet: The surreal leap from sentencing hearing to Oscar buzz28:00 – True Jackpot: Family: Defying 1% IVF odds to welcome daughter Fiona33:00 – Closing Hand: Your Next Chapter: Molly’s challenge to turn every setback into a comebackNotable Quotes“I just remember making a promise to the universe: I will never abandon my values, my family, or myself ever again.” Molly Bloom“If you’re unwilling to take another bold risk after a bad beat, you’ll stay right where you are.” Molly Bloom“There’s a freedom in losing everything—because then you can’t be anyone but who you really are.” Molly Bloom“I met Aaron Sorkin by betting on the best horse in Hollywood, even when my own book had sold ten copies.” Molly BloomValuable ResourcesMolly’s Game (Aaron Sorkin, 2017) & Molly’s Game memoir by Molly BloomKey TakeawaysIntegrity Pays Dividends: Choosing values over easy outs—even under federal indictment—builds lifelong credibility.Leverage Athletic Grit: The discipline that wins races can also power comebacks after personal and professional collapse.Build Your Village: Sustainable success requires support: mentors, family, hired help, and radical self-care.Own Your Story: When life derails you, the only way forward is to become the author of your own narrative.Bet on Yourself: Even if your first “hand” flops (book sales, legal battles), bold risks can unlock game-changing opportunities.Redefine the Jackpot: True victory lies not in money or fame, but in resilience, relationships, and the chance to start anew.Tune in for more wisdom from Molly’s journey—and get ready to play your next hand with courage and conviction.Connect with Dwayne KerriganFacebookInstagram

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