Unmasked: The CEO Files

By Leanne Bucaro, Alan McLaren

The mic is on. The masks are off.

UNMASKED: The CEO Files explores the leadership journeys you don’t see on LinkedIn. The turning points,

the real pivots, the moments that shaped who these leaders bec... more

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FAQs about Unmasked: The CEO Files:

How many episodes does Unmasked: The CEO Files have?

The podcast currently has 52 episodes available.

Unmasked: The CEO Files episodes:

January 15, 2026 From Fear to Flight: Overcoming Deep Seeded Fears to Achieve Amazing Success with Patrick Sweeney
What if the fear holding you back was actually the fuel for your biggest breakthroughs?
In this episode of Unmasked: The CEO Files, Alan McLaren sits down with Patrick Sweeney - Wall Street Journal bestselling author, investor, entrepreneur, world-record athlete and globally recognized fear expert known as “The Fear Guru”.
Patrick shares his incredible journey from battling rare leukemia and crippling fear, to building and exiting multiple companies, investing in dozens more and helping hundreds of leaders transform fear into peak performance.
He also breaks down the foundational ideas behind his upcoming book, The Founder’s Creed, including the belief-based BOODA Doctrine™ which is a framework designed to help founders, CEOs and executive teams scale with clarity, conviction, and shared leadership signal.
Whether you’re leading a startup, navigating hyper-growth or asking how to turn fear into action, this episode delivers insight and tools you can use today.
In this episode, we explore:
➡️ Why fear isn’t your enemy and how courageous leaders use it as fuel
➡️ Patrick’s life-altering experience with leukemia and how it reshaped his approach to leadership and risk
➡️ The BOODA Doctrine™ as the core driver of company culture and operational success
➡️ How shared belief maps and leadership alignment can turn chaos into cadence
➡️ Advice for CEOs facing fear, uncertainty and imposter syndrome in personal or professional life
🔗 Connect with Patrick on LinkedIn: https://www.linkedin.com/in/thefearguru/
🔗 To learn more about Patrick's book visit: https://www.thefounderscreed.com/
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43min
January 08, 2026 From Success to Significance with Pioneer Jeff Cullen | Unmasked: The CEO Files
In this episode of Unmasked: The CEO Files, host Alan McLaren sits down with entrepreneur and YPO leader Jeff Cullen for a deeply honest conversation about leadership, neurodiversity, trust and building a values-based business that lasts.
Jeff shares his journey from founding a Canadian logistics company at 27 to scaling it into a multinational organization across 17 countries and navigating both a painful fire-sale exit and a later, highly successful acquisition. Along the way, he opens up about living with ADHD, managing impostor syndrome, surviving financial crisis, and why leadership is less about control and more about accountability, alignment, and trust.
This episode goes beyond growth metrics and exits to explore what it really means to move from success to significance, including how transparency, advisory boards, cultural accountability and a “prosperity for all” mindset can transform both people and performance.
If you’re a CEO, founder, or senior leader navigating scale, pressure, or personal doubt, this conversation offers hard-earned lessons in leadership signal, resilience, and building trust at scale.
In this episode, we explore:
➡️ How ADHD can become a leadership superpower - not a limitation
➡️ The shift from responsibility to accountability that transformed company culture
➡️ Lessons from a financial crisis, failed exit, and rebuilding stronger than before
➡️ Why advisory boards, trust, and listening are critical at the CEO level
➡️ How “prosperity for all” creates alignment, loyalty, and long-term performance
Connect with Jeff Cullen:
🔗 LinkedIn: https://www.linkedin.com/in/jeffrey-cullen-b2566a3/
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51min
December 18, 2025 Meet Captain Compliance: The Risk That Quietly Costs CEOs Millions with Guest Richart Ruddie
In this episode of Unmasked: The CEO Files, host Alan McLaren chats with Richart Ruddie, Founder of Captain Compliance, to unpack the real journey behind building exiting and scaling businesses in fast-changing digital environments.
From starting his career during the financial crisis to becoming an entrepreneur by accident, Richart shares how relentless learning shaped his leadership journey while discussing the emotional reality of exits, the pressure founders face to move fast without perfection and why privacy compliance has become one of the most critical (and overlooked!) risks for modern businesses.
This conversation is a candid look at leadership under pressure, building trust at scale and leading with clarity in an era defined by data, AI and constant change.
In this episode, we explore:
➡️ How curiosity and learning fuel long-term leadership growth
➡️ The real lessons behind failed ventures and successful exits
➡️ Why privacy compliance is now a competitive advantage
➡️ The emotional shift founders experience after an exit
➡️ How leaders balance speed, imperfection and trust while scaling
Whether you’re a CEO, founder, or operator navigating growth, exits, or regulation, this episode offers hard-earned insight into leading with clarity, resilience, and intention.
Connect with Richart Ruddie:
🔗 LinkedIn: https://www.linkedin.com/in/richartruddie/
👉 Website: https://captaincompliance.com/
🎥 YouTube: https://www.youtube.com/@captain-compliance
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39min
November 13, 2025 From Chaos to Clarity - Leadership Unfiltered with YPO Guest Dusty Holcomb
In this episode of Unmasked: The CEO Files, host Alan McLaren sits down with Dusty Holcomb, a leadership advisor and YPO member for a deeply personal and insightful conversation on what it really takes to lead.
From growing up homeschooled to building a 30-year career in leadership and corporate growth, Dusty shares the experiences that shaped his mindset and the lessons he learned from a retired colonel who became his greatest mentor.
Together, Alan and Dusty unpack the difference between leadership and management, the power of clarity over chaos, and why self-awareness and authenticity are the foundation of sustainable leadership. Dusty reveals how owning your mindset, aligning your purpose, and understanding your “leadership signal” can transform not just how you lead, but how your entire organization shows up.
🎙️ In this episode, we explore:
➡️ Why leadership starts with self-leadership
➡️ The lesson that “you can’t scale chaos” and what clarity really means
➡️ The difference between managing outcomes and leading people
➡️ How to turn self-awareness into your biggest leadership advantage
➡️ Why authenticity isn’t about being liked - it’s about being real
If you’ve ever felt the weight of high-stakes decisions, struggled with self-doubt, or wondered how to lead with greater purpose and alignment, this conversation will hit home.
When it comes to culture, Dusty believes every leader must have clarity on these five questions — especially the last two, which are often the hardest to answer:
➡️ Why are we here? – What’s our purpose beyond making money?
➡️ Where are we going? – What’s our vision over the horizon?
➡️ How are we going to get there? – The plan, the method, the process.
➡️ Where do I fit in? – How does my work connect?
➡️ What’s in it for me?
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48min
November 06, 2025 When Irish Eyes Are Smiling - Purposeful Decision Making with YPO Guest: Pádraig Ó Céidigh
Join Alan McLaren as he chats with Pádraig Ó Céidigh (teacher, lawyer, accountant, entrepreneur, and former senator) who built a €150M airline from the ground up, is a former winner of Ireland EY Entrepreneur of the Year and represented Ireland at EY World Entrepreneur of the Year.
Alan and Pádraig discuss the art of purposeful decision-making in leadership, exploring how to align personal values with business goals, balance immediate actions with long-term impact and lead with authenticity and integrity. Drawing on lessons from aviation, entrepreneurship, and his YPO experience, Pádraig shares practical frameworks and real-world insights that empower leaders to make consistent, transparent, and resilient decisions that truly move the needle.
In this episode, we explore:
➡️ How risk reduction and safety optimization from aviation can inform everyday business decisions.
➡️ Building a personal decision-making framework that aligns with your values and
organizational goals.
➡️ Balancing short-term actions with long-term impact for sustained leadership success.
➡️ Decision-making styles and self-reflection techniques to refine them.
➡️ Common pitfalls in decision-making and staying adaptable while leading with integrity.
Whether you’re a CEO, founder, or emerging leader, this conversation offers practical frameworks and inspiration for purpose-driven leadership.
🔗 Connect with Pádraig Ó Céidigh on LinkedIn: https://www.linkedin.com/in/padraigoceidigh/
📚 Check out Pádraig's book, "The Purposeful Decision Maker: A Guide to Making Great Decisions in Life and Business" here: https://www.amazon.com/dp/B0DCKD7QSQ/ref=sr_1_1
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39min
October 09, 2025 Spiritual Heartbeat With Guest: Liv Fisch | STRATA Originals
Don’t forget to like, subscribe, and hit the bell for more conversations with leaders shaping the future of business. Click the links below, hit that 'Follow' button, and let the journey towards a stronger, more authentic personal brand begin! Connect with us and learn more about how you can create your own authentic personal brand: Website: https://strataoriginals.com/ LinkedIn: https://www.linkedin.com/company/8045398 Instagram: https://www.instagram.com/strata_originals/?hl=en Facebook: https://www.facebook.com/StrataOG Don't forget to engage with us in the comments, sharing your thoughts, questions, and your own personal brand victories. Together, let's create a community that thrives on empowerment and success.
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45min
September 25, 2025 Family Business Succession: Planning for the Next Generation with Guest Chuck Phillips
Running a family business is rewarding, but succession, buyouts, and leadership transitions are never simple. In this episode of STRATA Originals, Alan McLaren speaks with Chuck Phillips- CEO, board member, and family business consultant about the realities of keeping both businesses and families thriving across generations.
Chuck unpacks the emotional, financial, and governance challenges that come with family enterprises. From buyouts that strain relationships to boards that lack outside oversight, he explains how to avoid common pitfalls, strengthen governance, and prevent conflict before it destroys both wealth and family ties.
In this episode we explore:
➡️ Why family business buyouts are rarely straightforward
➡️ How boards and outside directors help prevent conflict
➡️ The risks of nepotism and why objectivity matters
➡️ When to bring in an outside CEO or fractional leader
➡️ Why proactive succession planning is cheaper than family litigation
If you’re a family business owner, next-gen leader, or advisor, this episode is packed with insights you can’t afford to miss!
🔗 Connect with Chuck Phillips on LinkedIn:
https://www.linkedin.com/in/chuck-phillips-5104438/
Don’t forget to like, subscribe, and hit the bell for more conversations with leaders shaping the future of business.
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32min
August 07, 2025 From Jedi to CEO: Mark Hamill on Navigating Executive Career Transitions | STRATA Originals
While he may not wield a lightsaber, this Mark Hamill is a force to be reckoned with when it comes to guiding executives through the next chapter of their leadership journey!
Mark Hamill, founder of The Naked Headhunter, Virtual Advisory Board, and MyFractional, joins Alan McLaren to break down how high-level executives can navigate life after the C-suite - and find new purpose, relevance, and opportunity.
With a global team of expert search professionals and advisors, Mark’s companies are on track to help over 1,000 of the world’s most passionate entrepreneurs make the No. 1 hire they need to achieve their vision.
A 15-year active YPO member, Mark brings unmatched insight into the transition from operator to advisor - and what it really takes to build a meaningful portfolio career in today’s fast-moving world.
In this episode we explore:
➡️ Why loneliness is the #1 challenge for CEOs in transition
➡️ The truth about search firms — and where real opportunities come from
➡️ How fractional roles bring back the “cut and thrust” of leadership
➡️ Why clarity comes from 75+ strategic conversations
➡️ How to own your story (even if you're terrible at telling it)
➡️ Why personal branding isn’t a luxury—it’s your lifeline
➡️ AI, authenticity, and the future of learning as a leader
➡️ The mindset shift from “what’s next?” to “where can I add value?”
Whether you're in a transition, building a board portfolio, or simply redefining what leadership looks like today - this is a must-listen conversation.
🔗 Connect with Mark Hamill:
🌐 https://www.thenakedheadhunter.com
📧 [email protected]
💼 LinkedIn: https://www.linkedin.com/in/markhamill/
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42min
August 01, 2025 Built for Impact: Kevin Johnson on Legacy, Launchpads, and Leadership | STRATA Originals
From the Streets to the C-Suite, Kevin Johnson, CEO of WPP Media Group, joins Leanne to unpack what it really takes to lead with bold inclusive leadership.
In this episode, Kevin shares the personal story behind his leadership: how one teacher nearly broke him and another lit the fire that never went out. That fire led him to the C-Suite and to Launchpad, an internal WPP program that trains people from non-traditional backgrounds: single moms, crane operators, Uber drivers with PhDs and gives them opportunity to get hired.
This isn’t theory. It’s lived experience. It’s legacy. It’s what happens when leadership stops gatekeeping and starts building real onramps.
If you’re building anything that matters or trying to figure out how to lead with impact, this one’s for you!
In this episode, we explore:
➡️ The power of safe spaces and storytelling that hits deep
➡️ From crane operator to team member - "Started from the bottom..."
➡️ How diverse lived experience fuels real innovation
➡️ Why we need more diversity at the top
➡️ AI as a creative ally - not a threat
➡️ Faster insights, better briefs, smarter work
➡️ Supporting Canadian media in a changing landscape
➡️ Advice Kevin wishes he heard at 18
Connect with Kevin Johnson on LinkedIn: https://www.linkedin.com/in/kevin-johnson-8604423/
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58min
June 27, 2025 Building Impactful Communities with Jeremy Sharpe | STRATA Originals
In this episode of STRATA Originals, Leanne Bucaro chats with Jeremy Sharpe, President of Sharpe Development Group on how he grew a multigenerational real estate and development company behind Rancho Sahuarita- a 3,000-acre award-winning master-planned community in Southern Arizona.
Jeremy shares his passion for creating a better life for people through thoughtfully built communities. From residential development and commercial assets to water and community management operations, Jeremy discusses how his family company blends legacy with innovation, focusing on people, flexibility, and long-term impact.
In this episode, we explore:
➡️ Jeremy’s role in leading operations and asset management at Sharpe Development Group
➡️ The story behind Rancho Sahuarita’s success as a 3,000-acre master-planned community
➡️ Balancing commercial and residential development with community management
➡️ How family legacy influences business values and culture
➡️ The role of intentional community-building in creating better lives
➡️ What’s next for Jeremy and Sharpe Development Group - upcoming projects, expansion, and new opportunities
Connect with Jeremy Sharpe on LinkedIn: https://www.linkedin.com/in/jeremynsharpe/
Visit Jeremy's website here: https://ranchosahuarita.com/
Ready to immerse yourself in a world of personal branding wisdom?
Click the links below, hit that 'Follow' button, and let the journey towards a stronger, more authentic personal brand begin!
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50min

FAQs about Unmasked: The CEO Files:

How many episodes does Unmasked: The CEO Files have?

The podcast currently has 52 episodes available.