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In Part 2 of The Dwayne Kerrigan Podcast with Mara Dorne, the conversation goes beyond business and into the mindset that helped create her success.
Mara opens up about living with anxiety, navigating “mom guilt”, and the personal sacrifices involved in becoming successful. Authenticity has been a major key for Mara, who has learned over time what it takes to thrive without losing yourself. Her transparency and humor will inspire you to embrace your truth and imperfections, and lead with both power and compassion.
Episode Highlights
00:00 – “Progress brings happiness.”
01:15 – “Look good, feel good, do good.” How inner confidence fuels outer success.
05:30 – Energy equals productivity — lessons from Tony Robbins on physiology and focus.
09:30 – The truth about mom guilt, mom shaming, and giving yourself grace.
17:00 – Setting boundaries and choosing family over constant business travel.
21:30 – “People like you when you’re authentic.” Leadership lessons from letting go of ego.
31:15 – Owning her anxiety — how Mara turned fear into focus and vulnerability into power.
43:00 – “Pain is inevitable, but suffering is optional.” Choosing resilience and self-love.
49:30 – “You’re not going to be everybody’s cup of tea — and that’s okay.”
Key Takeaways:
Notable Quotes:
“There is absolute guilt. I’m the mom at the football meet in heels, on the phone, juggling everything. But at some point, you’ve got to give yourself grace.” Mara Dorne
“You’re not going to be everybody’s cup of tea — and that’s okay. Peel back the layer and be who you want to be.” Mara Dorne
“Being a woman is a superpower. It really is a superpower, especially in sales, because men like to talk to women and women like to talk to women.” Mara Dorne
“We’re all going to experience pain. But what you don’t have to experience is suffering. You don’t have to suffer.” Dwayne Kerrigan
Mara is a self-made millionaire, best-selling author, public speaker, and award winning BILF ('Boss I'd Like to Follow') who built a remarkable career in a male-dominated industry. As a top leader at a Fortune 500 subsidiary, she made history by exceeding $1 billion in sales before turning 40. Beyond her corporate achievements, Mara is passionate about mentoring and has guided over 1,500 health insurance agents nationwide, with a particular focus on empowering female entrepreneurs.
Links:
Website: https://maradorne.com/
Facebook: https://www.facebook.com/TheDorneRegion
TikTok: https://www.tiktok.com/@mara.dorne
Instagram: https://www.instagram.com/maradorne/
LinkedIn: https://www.linkedin.com/in/maradorne/
BILF Podcast: https://maradorne.com/bilf-podcast/
Connect with Dwayne Kerrigan
Linked In
Website
Disclaimer: The views, information, or opinions expressed by guests during The Dwayne Kerrigan Podcast are solely those of the individuals involved and do not necessarily represent those of Dwayne Kerrigan and his affiliates. Dwayne Kerrigan or The Dwayne Kerrigan Podcast is not responsible for and does not verify the accuracy of any of the information contained in the podcast series. The primary purpose of this podcast is to educate and inform. Listeners are advised to consult with a qualified professional or specialist before making any decisions based on the content of this podcast.
Mara Dorne, self-made millionaire and top leader at a Fortune 500 subsidiary, joins The Dwayne Kerrigan Podcast this week to share her insights and wisdom in all things business. Mara has built a remarkable career in a male-dominated industry. She made history when she exceeded $1 billion in sales before turning 40, so she knows a thing or two about the formula for success.
In Part One of their discussion, Mara opens up to Dwayne about her resilience, rebuilding from scratch, and how finding her WHY changed everything. They unpack everything from the changing sales landscape in a post-COVID world, to the non-negotiables of leadership, recruiting, and mindset.
If you agree that business, and life, should be about pursuing purpose and passion, not paycheques, this episode is for you!
Highlights:
00:00 – Mara opens with her mantra: “A.B.C. – Always Be Closing.”
02:10 – From broke to a billion: Mara’s journey to leading 1,500 agents.
05:45 – Why remote work kills culture — and why energy drives sales.
10:15 – Insights from Tony Robbins and Patrick Bet-David on adapting to change.
12:10 – “Work-life balance is a theory — it doesn’t exist for go-getters.”
16:30 – Always be recruiting: how to build growth through referrals and social media.
21:15 – Bob Proctor’s influence and the role of personal development in leadership.
33:00 – “Scared money don’t make money” — how to invest wisely during downturns.
42:45 – The moment everything changed: from broke to $92K in six months.
56:30 – “When you look good, you feel good. When you feel good, you do good.”
Key Takeaways
Mara is a self-made millionaire, best-selling author, public speaker, and award winning BILF ('Boss I'd Like to Follow') who built a remarkable career in a male-dominated industry. As a top leader at a Fortune 500 subsidiary, she made history by exceeding $1 billion in sales before turning 40. Beyond her corporate achievements, Mara is passionate about mentoring and has guided over 1,500 health insurance agents nationwide, with a particular focus on empowering female entrepreneurs.
Links:
Website: https://maradorne.com/
Facebook: https://www.facebook.com/TheDorneRegion
TikTok: https://www.tiktok.com/@mara.dorne
Instagram: https://www.instagram.com/maradorne/
LinkedIn: https://www.linkedin.com/in/maradorne/
BILF Podcast: https://maradorne.com/bilf-podcast/
Quotes:
“ABC, always be closing. It’s a constant conversation. I’m telling everybody that I know in my life works in this, even my ex-husband and my husband—it’s crazy. And why wouldn’t you want to offer that to somebody if you’re doing well with it and you know that there is uncapped income potential, unlimited growth, you can be your own boss, you’re in business for yourself, not by yourself.” Mara Dorne
“Scared money don’t make money. I learned that very early on.” Mara Dorne
“Inspect what you expect. And if you don’t do that—because sometimes you think they got it—they don’t got it.” Mara Dorne
“It’s an unbelievable story of necessity. When things are that desperate—and you know, necessity is the mother of all skill, as they say—you just have to find a way.” Dwayne Kerrigan
Connect with Dwayne Kerrigan
Linked In
Website
Disclaimer: The views, information, or opinions expressed by guests during The Dwayne Kerrigan Podcast are solely those of the individuals involved and do not necessarily represent those of Dwayne Kerrigan and his affiliates. Dwayne Kerrigan or The Dwayne Kerrigan Podcast is not responsible for and does not verify the accuracy of any of the information contained in the podcast series. The primary purpose of this podcast is to educate and inform. Listeners are advised to consult with a qualified professional or specialist before making any decisions based on the content of this podcast.
In Part 2 of The Dwayne Kerrigan Podcast with John Karpov, founder and CEO of Action Home Services, Dwayne and John go even deeper into the mindset and systems behind Action Home Services(AHS), a leading landscaping and exterior construction company serving Toronto and the Greater Toronto Area.
From almost losing his residency to scaling an $8M business while facing deportation, John shares how he built structure, leadership, and culture around his immigrant grit. He opens up about redefining fulfillment, transitioning from survival mode to leadership, and how relentless personal growth became the cornerstone of his company’s 50% year-over-year growth.
John reveals his leadership playbook — from reading 2 books a month to building over 1,000 SOPs and investing $1.5M in professional development for his team — and how staying humble, hungry, and human is what keeps him grounded through every phase of growth.
If Part 1 was about survival, this episode is about scaling — with purpose, structure, and soul.
Listen to Part 1 HERE
Watch Part 1 HERE
Timestamps
[00:00:00] — Dwayne opens with: “You can only run a business so long by running the fastest.”
[00:01:00] — John’s incredible story of his wife’s visa approval and their shared “never give up” destiny.
[00:05:00] — The immigration battle: how they nearly lost everything waiting for permanent residency.
[00:07:30] — The miracle timing that let them stay in Canada and the lessons learned living on the edge.
[00:10:00] — Reinvesting every dollar into the business while facing uncertainty.
[00:13:00] — Scaling to $10M+ before age 25 — and not feeling like it’s an accomplishment.
[00:17:00] — Dwayne and John explore scarcity versus hunger — and how the immigrant mindset fuels drive.
[00:19:00] — John on never feeling “done” and why fulfillment comes from helping others succeed.
[00:22:30] — The breakthrough realization: happiness is in the journey, not the destination.
[00:26:00] — Daily fulfillment rituals: reading, training, and prioritizing sleep.
[00:29:00] — Building structure and delegation into the company’s DNA — leadership by design.
[00:31:00] — Creating organizational charts, head of departments, and scaling through people.
[00:35:30] — Learning to lead through education: 100+ conferences and a book club culture.
[00:38:00] — Investing $1.5M in personal and professional development and $40K in books.
[00:41:00] — Company reading list and rewards program: from “Unreasonable Hospitality” to “Good to Great.”
[00:45:00] — John’s transparent leadership: open-book finances, KPI education, and growth accountability.
[00:49:00] — Over 1,000 SOPs: how structure scales culture.
[00:53:00] — Turning every mistake into a process and every error into a lesson.
[00:56:00] — The ROI of structure: new managers finally saying, “I love that it’s organized.”
[00:58:00] — Why immigrants often make exceptional employees — grit meets gratitude.
[01:00:30] — Dwayne’s reflection on the power of sacrifice and the immigrant spirit.
[01:02:00] — John’s final advice: “If you need my help with your business, I’ll be there for you.”
Key Takeaways
Resources Mentioned
Books:
Referenced Concepts:
Quotes:
“You can only run a business for so long by running it through the mechanism of running the fastest. That usually ends up being the small entrepreneur way, and then you can't grow beyond that.” - Dwayne Kerrigan
“I think sometimes the worst thing that we could rely on is this need for certainty where everything fits in a box and everything is going to be great, and we have this absolute certainty and that just doesn't exist in life.” - Dwayne Kerrigan
“The amount of change and breakthroughs I go through every year is remarkable. My mindset shifts every single year.” — John Karpov
“Fulfillment comes from impacting other people’s lives. When my team buys homes and grows, that’s when I feel truly successful.” — John Karpov
“The real destination is the journey. Happiness isn’t five years from now — it’s today.” — John Karpov
“Every mistake creates an SOP. Every error becomes a lesson. That’s how we grow.” — John Karpov
Links:
Connect with Dwayne Kerrigan
Linked In
Website
Disclaimer: The views, information, or opinions expressed by guests during The Dwayne Kerrigan Podcast are solely those of the individuals involved and do not necessarily represent those of Dwayne Kerrigan and his affiliates. Dwayne Kerrigan or The Dwayne Kerrigan Podcast is not responsible for and does not verify the accuracy of any of the information contained in the podcast series. The primary purpose of this podcast is to educate and inform. Listeners are advised to consult with a qualified professional or specialist before making any decisions based on the content of this podcast.
At just 17 years old, John Karpov immigrated alone from Kazakhstan to Canada, barely speaking English and with no safety net. When a scam wiped out his savings and left him contemplating suicide, one phone call saved his life, and set off a chain of events that would redefine what grit and perseverance look like.
In this powerful conversation, Dwayne Kerrigan sits down with John to unpack how he went from a desperate student to the founder of Action Home Services, a multimillion-dollar landscape construction company. John shares how he learned English, mastered sales by necessity, and built a thriving business one door knock at a time.
This is a masterclass in resilience, risk, and the immigrant mindset that fuels unstoppable entrepreneurs.
Timestamps
00:00 - John reflects on fear, scarcity, and the pain that still drives him 11 years later.
01:00 - Dwayne introduces John Karpov, founder of Action Home Services.
03:00 - John’s early life in Kazakhstan and decision to immigrate to Canada at 17.
05:00 - Struggling to understand North American English and adapting to culture shock.
06:00 - Losing his financial support — and falling victim to a fraud that wiped out his savings.
08:00 - A near-suicidal moment and the phone call that changed everything.
10:00 - Finding a commission-only job selling driveway sealing — and having no clue what it was.
15:00 - Knocking doors for 8 hours with no sales — until a breakthrough changes everything.
17:30 - A confrontation, courage, and earning $400 in a day — more than a month’s pay back home.
19:00 - What kept him from giving up — the mindset shift from failure to relentless drive.
23:00 - Outworking everyone and learning the power of necessity.
25:00 - Starting his first business with no money, no truck, no driver’s license — and no experience.
31:00 - Working 60 hours a week while in college — the early years of survival.
34:00 - Transition from driveway sealing to landscaping and scaling beyond himself.
38:00 - Dwayne and John break down the principles of sales: activity, energy, and hunger.
41:30 - The scarcity mindset that still lingers — and how fear drives discipline.
47:00 - Risk, safety, and how to protect a growing business through systems and liquidity.
53:00 - Building systems, crews, and leadership while finishing college.
1:03:00 - Growing past chaos: when your living-room floor becomes your job-scheduling system.
1:07:00 - Bringing his wife into the business — and the promise to be home by 5 p.m.
1:13:00 - Her immigration story — and how persistence beat three rejections.
1:14:00 - Dwayne’s closing reflections: from scarcity to abundance — and what’s coming in Part 2.
Key Takeaways
Quotes:
“The moment I start knocking those doors, the flame inside of me started, and I just knew I cannot give up. I need to actually get back on track. I cannot fail my parents because they gave me this opportunity to come in.” John Karpov
“For me, grow, it's in my DNA, like it's in my blood. I would never stop growing.” John Karpov
“I think it is still a scarcity that somebody can take it away, that it still could be over, and it still could turn totally different. The pain which I had, it's probably still didn't heal for, and it's been 11 years, so I don't think I'm fully over it.” John Karpov
“It’s amazing to me, like even when you just explained it like that, I kept on thinking: people who don’t have a business think, ‘oh, you did a million in revenue, you’ve gotta be making big money,’ and you go, no — your parameters around not being broke were, I had rent and I had food, and everything else was going back into the business. That’s the life of an entrepreneur.” Dwayne Kerrigan
John is President of Action Home Services (AHS), a leading landscaping and exterior construction company serving Toronto and the Greater Toronto Area. Since founding AHS in 2015, John has grown the business from a small driveway sealing service into one of the GTA’s premier full-service landscaping and outdoor design firms. Under his leadership, the company has become known for its craftsmanship, reliability, and innovative outdoor solutions, specializing in interlocking, landscaping, pool installations, decks, fences, and complete backyard transformations. John’s commitment to quality and customer satisfaction has earned AHS multiple awards and a trusted reputation across the region.
Links:
Connect with Dwayne Kerrigan
Linked In
Website
Disclaimer: The views, information, or opinions expressed by guests during The Dwayne Kerrigan Podcast are solely those of the individuals involved and do not necessarily represent those of Dwayne Kerrigan and his affiliates. Dwayne Kerrigan or The Dwayne Kerrigan Podcast is not responsible for and does not verify the accuracy of any of the information contained in the podcast series. The primary purpose of this podcast is to educate and inform. Listeners are advised to consult with a qualified professional or specialist before making any decisions based on the content of this podcast.
In Part 2 of this inspiring conversation, Dwayne Kerrigan sits down again with Jim Ritter, founder of Printed Farms and builder of the world’s largest 3D-printed building. Jim shares not only the technical and economic realities of 3D-printed housing but also the mindset shifts, calculated risks, and reinventions that have defined his remarkable journey.
From navigating lawsuits and seizing unique niches, to pivoting from horses to housing in his sixties, Jim embodies the belief that innovation has no age limit. Along the way, he draws lessons from history, technology, and personal trial-and-error—reminding us that small, consistent actions and adaptability are the true engines of progress.
Whether you’re in construction, entrepreneurship, or simply seeking inspiration for your own reinvention, this episode offers both practical takeaways and timeless wisdom.
Timestamps
00:00 – “If you say you can or you say you can’t, you’ll be true in both.”
01:00 – Why this conversation is about more than building—it’s about innovation and mindset
02:00 – Economics of 3D printing: materials, labor, and early success stories
06:00 – Finding niches through setbacks: lawsuits, loopholes, and launching into 3D printing at 64
08:00 – Innovation vs. practicality: why things must work before they can scale
10:00 – Stories of invention: dishwashers, electric cars, and how adoption really happens
13:00 – Global housing crisis and opportunities for 3D printing
17:00 – Pivoting when plans fail: keeping ventures “plastic” and adaptable
21:00 – The value of small, consistent changes that compound over time
25:00 – Looking back at unexpected career pivots across decades
29:00 – Why career reinvention is vital—and more possible now than ever
33:00 – Risk, mitigation, and the realities of jumping into new ventures
36:00 – Construction + tech: opportunities for the next generation
40:00 – Financing, risk tolerance, and who’s ready for entrepreneurship
41:00 – Mindset: “If you say you can or you say you can’t, you’ll be true in both.”
46:00 – Printing on Mars? Future frontiers in construction and robotics
49:00 – Translation tech, AI, and accelerating innovation
52:00 – Why this is the greatest time in history to be alive
54:00 – Closing: entrepreneurship, courage, and embracing innovation at any stage
Notable Quotes
Key Takeaways
Resources & Mentions
Connect with Dwayne Kerrigan
Linked In
Website
Disclaimer: The views, information, or opinions expressed by guests during The Dwayne Kerrigan Podcast are solely those of the individuals involved and do not necessarily represent those of Dwayne Kerrigan and his affiliates. Dwayne Kerrigan or The Dwayne Kerrigan Podcast is not responsible for and does not verify the accuracy of any of the information contained in the podcast series. The primary purpose of this podcast is to educate and inform. Listeners are advised to consult with a qualified professional or specialist before making any decisions based on the content of this podcast.
In this episode of The Dwayne Kerrigan Podcast, Dwayne sits down with Jim Ritter, founder of Printed Farms and the man behind the world’s largest 3D-printed building. Jim’s story is one of relentless innovation—pivoting industries later in life, solving real-world housing problems, and challenging outdated construction methods with cutting-edge robotics and 3D printing technology.
From the challenges of curing concrete in extreme heat to the economics of large-scale printing, Jim reveals what it really takes to make 3D-printed housing viable. He explains the logistical nightmares of early machines, why cement isn’t the perfect print material, and how his team has built a new system to solve industry problems.
This is more than a conversation about construction—it’s about innovation, adaptability, and the future of housing.
Timestamps
00:00 – The cost of bright ideas: what you don’t know can hurt you
01:00 – Meet Jim Ritter, founder of Printed Farms, and his late-career pivot into 3D printing
02:00 – Why curing time makes or breaks a 3D-printed wall
05:00 – The myths of “printing a house in a day” and the real economics
07:30 – Shell costs, square footage, and learning from first projects
10:00 – Logistical nightmares of early machines and moving heavy equipment
13:00 – Why robotics and 3D printing matter in solving global housing shortages
16:00 – A simple breakdown: how 3D printing a house actually works
20:00 – Pouring beams, columns, and integrating trades in one process
24:00 – Why stronger, smarter structures are critical for climate resilience
27:00 – Innovation always starts small—3D printing’s parallels to early tech adoption
32:00 – Safety, silos, and the hidden dangers of construction work
36:00 – Old machines vs. new mobility: why hoses and pumps kill efficiency
42:00 – Cutting material waste and rethinking the economics of building
47:00 – Reinventing mixers and achieving consistent quality
52:00 – Training the future workforce: print operators, not laborers
58:00 – Economics, labor shortages, and why machines are the future of building
01:02:00 – Permitting, insurance, and how 3D printing fits into existing systems
01:05:00 – Closing thoughts: innovation is not optional—it’s survival
Jim Ritter is a lifelong horseman, entrepreneur, and innovator. After decades competing internationally in show jumping and developing equestrian properties in the U.S. and Sweden, he turned his focus to real estate and advanced construction. In 2019, he founded Printed Farms, the company behind Florida’s first permitted 3D-printed home and the world’s largest 3D concrete printed building. Today, Jim continues to pioneer new patented printing systems through his latest venture, CASPER, shaping the future of construction technology.
Notable Quotes
Key Takeaways
Resources & Mentions
Connect with Dwayne Kerrigan
Linked In
Website
Disclaimer
The views, information, or opinions expressed by guests during The Dwayne Kerrigan Podcast are solely those of the individuals involved and do not necessarily represent those of Dwayne Kerrigan and his affiliates. The podcast is not responsible for and does not verify the accuracy of any of the information contained in the series. The primary purpose of this podcast is to educate and inform. Listeners are advised to consult with a qualified professional before making any decisions based on the content.
In this powerhouse second half of Dwayne Kerrigan’s conversation with Tod Melnyk, COO of Martell Media, the focus turns to the bold, disruptive goal of making 90% of their workflow AI-driven by the end of the year. Tod opens up about leadership transitions, the importance of shadowing for accelerated learning, and the framework behind their coaching programs that keep entrepreneurs accountable through five daily non-negotiables.
From integrating life and business to running calendar audits that reveal where time really goes, Tod shares the behind-the-scenes playbook of how Martell Media scales with intention, precision, and AI-powered execution.
If you’re a business owner wondering how to embrace AI without losing the human touch—or how to structure your calendar and team to unlock exponential growth—this episode is for you.
Timestamps
00:00 – Why 90% of workflow should be done by AI (and what that really means for jobs)
02:00 – Leadership lessons from stepping into responsibility at Dan Martell Media
03:30 – The #1 piece of advice for CEOs when onboarding key hires
05:00 – Shadowing as the fastest way to transfer culture and context
07:00 – Building Dan Martell’s brand: business content + personal integration
09:00 – Balance vs. integration: why separating business and personal doesn’t work
12:00 – The 5 Daily Non-Negotiables
16:00 – Group coaching frameworks and events at Dan Martell Media
17:30 – The AI Adoption Summit and Martell Ventures’ incubation of AI tools
20:00 – How prompt engineering + execution drive real results
22:00 – Using AI for scorecards, insights, and leadership team accountability
26:00 – Why businesses that don’t adopt AI face a bleak future
32:00 – Calendar audits: how to reclaim time and identify blind spots
36:00 – A day in the life: Tod’s 4 AM mornings, workouts, and time-blocked schedule
41:00 – The critical role of executive assistants in scaling beyond yourself
44:30 – Feedback, accountability, and the power of collaborative leadership
46:00 – Parting advice: dream big, be kind, and have fun
Notable Quotes
“I want 90% of your workflow done by AI. Not to replace you—but to amplify you as a human.” – Tod Melnyk
“The single best way to get someone up to speed is to have them shadow you for 30 days. Every meeting. Every conversation.” – Tod Melnyk
“If you’re not using AI in your business, it’s not going to be pretty.” – Tod Melnyk
“Five daily non-negotiables: workout, three posts on camera, review your goals, read 10 pages, and reach out to five people every day.” – Tod Melnyk
“What gets scheduled is what gets done.” – Dwayne Kerrigan
“Dream big. Be kind. Go have some fun.” – Tod Melnyk
Key Takeaways & Resources
Connect with Dwayne Kerrigan
Linked In
Website
Disclaimer
The views, information, or opinions expressed by guests during The Dwayne Kerrigan Podcast are solely those of the individuals involved and do not necessarily represent those of Dwayne Kerrigan and his affiliates. Dwayne Kerrigan or The Dwayne Kerrigan Podcast is not responsible for and does not verify the accuracy of any of the information contained in the podcast series. The primary purpose of this podcast is to educate and inform. Listeners are advised to consult with a qualified professional or specialist before making any decisions based on the content of this podcast.
In this episode of The Dwayne Kerrigan Podcast, Dwayne sits down with Tod Melnyk, COO of Martell Media. Martell Media is the powerhouse company behind bestselling author Dan Martell's high-impact content and coaching ecosystem. Together, Dwayne and Tod explore what it really takes to scale a business while staying true to culture and values.
Tod shares his journey from the brewing industry to running operations at one of the fastest-growing media companies in North America. Together, Dwayne and Tod break down:
Packed with real-world leadership lessons, this episode is a masterclass in operational excellence, culture building, and personal growth.
Timestamps
00:00 – 02:30 | Intro: Dwayne welcomes Tod and frames Dan Martell Media’s mission.
03:00 – 06:30 | Why building people comes before building business.
07:00 – 11:30 | The structure of one-on-ones, quarterly check-ins, and the 5-15 tool.
12:00 – 15:30 | Culture and core values at Martell Media: Build the People, Be the Example, Simple Scales.
18:00 – 22:00 | Kind warriors: balancing high performance with empathy.
23:00 – 28:30 | Tod’s leadership evolution: from hard-driving sales manager to authentic, self-aware leader.
29:00 – 34:30 | Going internal: how self-belief and reflection shift everything.
36:00 – 39:00 | The upside—and downside—of discipline.
41:00 – 45:30 | Scaling through others: why leaders must default to outcomes, not inputs.
47:00 – 49:30 | Common roadblocks leaders face when scaling: delegation, systems, and leadership.
50:00 – 55:30 | Visionary vs. Integrator: how Tod and Dan divide roles to scale.
57:00 – 58:30 | Closing thoughts & teaser for Part 2.
Notable Quotes
Resources & Mentions
Key Takeaways
Connect with Dwayne Kerrigan
Linked In
Website
Disclaimer: The views, information, or opinions expressed by guests during The Dwayne Kerrigan Podcast are solely those of the individuals involved and do not necessarily represent those of Dwayne Kerrigan and his affiliates. Dwayne Kerrigan or The Dwayne Kerrigan Podcast is not responsible for and does not verify the accuracy of any of the information contained in the podcast series. The primary purpose of this podcast is to educate and inform. Listeners are advised to consult with a qualified professional or specialist before making any decisions based on the content of this podcast.
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 investors. He also provides candid insights on Canada’s economic headwinds, the housing crisis, energy infrastructure, and the future of clean energy.
This episode is not just about real estate—it’s about resilience, responsibility, and redefining what it means to lead with integrity.
Timestamps
00:00 – Believing in yourself & taking risks when young
01:30 – What separates Skyline from its peers
05:00 – Succession, leadership, and the “piss and vinegar” test
09:00 – Building a multi-generational business
13:30 – The obligation of leading thousands of employees and investors
16:00 – Canada’s economic headwinds & the housing affordability crisis
20:00 – Lessons from the U.S. & why Canada needs a wake-up call
23:00 – Bureaucracy, red tape, and the need for real solutions in housing
29:00 – AI, energy demand, and Skyline’s role in future infrastructure
33:00 – Solar, biogas, and battery storage as scalable solutions
39:00 – Evaluating risk: from speculation to disciplined growth
44:00 – Advice to young entrepreneurs on risk-taking
46:00 – Staying grounded: Jason’s unchanging values despite growth
49:00 – The power of face-to-face relationships in a digital-first world
50:00 – Closing reflections on legacy, integrity, and inspiring the next generation
Notable Quotes
Resources & Mentions
Key Takeaways
Connect with Dwayne Kerrigan
Linked In
Website
Disclaimer: The views, information, or opinions expressed by guests during The Dwayne Kerrigan Podcast are solely those of the individuals involved and do not necessarily represent those of Dwayne Kerrigan and his affiliates. Dwayne Kerrigan or The Dwayne Kerrigan Podcast is not responsible for and does not verify the accuracy of any of the information contained in the podcast series. The primary purpose of this podcast is to educate and inform. Listeners are advised to consult with a qualified professional or specialist before making any decisions based on the content of this podcast.
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.
Timestamps
00:00 – The myth of the straight path in business & near-bankruptcy moments
01:30 – Introducing Jason Castellan & Skyline’s $9B journey
04:00 – Lessons from Walkerton: humility, farming roots & mentorship
07:00 – Childhood, hockey dreams, and how sports shaped his competitiveness
13:00 – The first student rental at Guelph and early entrepreneurial lessons
15:30 – Scaling to 52 houses: financing, sweat equity & creative problem-solving
21:00 – Financing strategies: trust, relationships, and building a social network
27:00 – Building your own legend: why life outside business matters
30:00 – Person vs. story: what investors really buy
33:00 – Facing doubt, trust, and learning to scale through partnerships
39:00 – Business battles, resilience, and “one more round” perseverance
42:30 – Experience creates strategy: when to let go & hire experts
46:00 – Leveraging talent: how Skyline attracted top-tier leaders
50:00 – Roadshows, raising capital & building Skyline’s REIT structure
55:00 – Closing thoughts: responsibility, growth, and investor trust
Notable Quotes
Resources & Mentions
Key Takeaways
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Disclaimer: The views, information, or opinions expressed by guests during The Dwayne Kerrigan Podcast are solely those of the individuals involved and do not necessarily represent those of Dwayne Kerrigan and his affiliates. Dwayne Kerrigan or The Dwayne Kerrigan Podcast is not responsible for and does not verify the accuracy of any of the information contained in the podcast series. The primary purpose of this podcast is to educate and inform. Listeners are advised to consult with a qualified professional or specialist before making any decisions based on the content of this podcast.
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