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Unmasked: The CEO Files

Unmasked: The CEO Files

Hosted by Leanne Bucaro, Alan McLaren

Episodes

57

Latest episode

Jun 2026

Language

EN

About the show

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 became beneath the title. We sit with executives as they talk candidly about building trust at scale, shaping culture, and staying visible without selling out who they are. Why it matters In a world of curated content and algorithm-chasing brands, UNMASKED offers something rare: a human signal that resonates. These are the stories behind the success. The decisions made in uncertainty. The moments that rewired how a leader shows up.

Listen to episodes

57 recent
June 11, 202640 min

Ashutosh Garg Host of the World’s Largest Podcast on the Power of Saying No

UNMASKED: The CEO Files. 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 became beneath the title. We sit with executives as they talk candidly about building trust at scale, shaping culture, and staying visible without selling out who they are. Why it matters: In a world of curated content and algorithm-chasing brands, UNMASKED offers something rare: a human signal that resonates. These are the stories behind the success. The decisions made in uncertainty. The moments that rewired how a leader shows up. Check out The Room Scan, it's a 5-minute read of the moment autopilot took over for CEOs and Founders who want to understand how visible and trusted their leadership signal really is: https://quiz.strataoriginals.com 🔗 Connect with Strata Originals Website: www.strataoriginals.com LinkedIn: Strata Originals

June 4, 202646 min

The Through Line Between Marketing, Leadership and Investing With Guest: Dave Sutton

UNMASKED: The CEO Files. 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 became beneath the title. We sit with executives as they talk candidly about building trust at scale, shaping culture, and staying visible without selling out who they are. Why it matters: In a world of curated content and algorithm-chasing brands, UNMASKED offers something rare: a human signal that resonates. These are the stories behind the success. The decisions made in uncertainty. The moments that rewired how a leader shows up. Check out The Room Scan, it's a 5-minute read of the moment autopilot took over for CEOs and Founders who want to understand how visible and trusted their leadership signal really is: https://quiz.strataoriginals.com 🔗 Connect with Strata Originals Website: www.strataoriginals.com LinkedIn: Strata Originals Instagram: @strataoriginals

May 21, 20261 hr 3 min

What Now? How to Ask For (and Receive) What You Need with Guest Dr. Ken Druck

UNMASKED: The CEO Files. 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 became beneath the title. We sit with executives as they talk candidly about building trust at scale, shaping culture, and staying visible without selling out who they are. Why it matters: In a world of curated content and algorithm-chasing brands, UNMASKED offers something rare: a human signal that resonates. These are the stories behind the success. The decisions made in uncertainty. The moments that rewired how a leader shows up. Check out The Room Scan, it's a 5-minute read of the moment autopilot took over for CEOs and Founders who want to understand how visible and trusted their leadership signal really is: https://quiz.strataoriginals.com

May 14, 202655 min

The Leadership Feedback That Changed Everything With Guest Kerry Siggins

If you’re a CEO, founder, executive, or investor navigating growth and high-stakes decisions, this episode offers powerful insight into the invisible variables shaping leadership outcomes! 🔗 Connect with Kerry Siggins on LinkedIn: https://www.linkedin.com/in/kerry-siggins/ Check out Kerry's books by visiting these two Amazon links: 📚Talk with Trust: https://www.amazon.com/gp/product/B0GX7N175H 📚Ownership Mindset: https://www.amazon.com/Ownership-Mindset-Handbook-Transforming-Leadership/dp/1637554346/ref=sr_1_1?crid=1K46E50JIF2BT&keywords=9781637554340&qid=1686927353&sprefix=9781637554340%2Caps%2C59&sr=8-1 ____ UNMASKED: The CEO Files. 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 became beneath the title. We sit with executives as they talk candidly about building trust at scale, shaping culture, and staying visible without selling out who they are. Why it matters: In a world of curated content and algorithm-chasing brands, UNMASKED offers something rare: a human signal that resonates. These are the stories behind the success. The decisions made in uncertainty. The moments that rewired how a leader shows up. Check out The Room Scan, it's a 5-minute read of the moment autopilot took over for CEOs and Founders who want to understand how visible and trusted their leadership signal really is: https://quiz.strataoriginals.com 🔗 Connect with Strata Originals Website: www.strataoriginals.com LinkedIn: Strata Originals Instagram: @strataoriginals

April 9, 202640 min

Stop Competing. Define the Category. With Guest Kevin Maney, Author, Journalist, Consultant

January 15, 202642 min

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/ ____

January 8, 202650 min

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/

December 18, 202538 min

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

November 13, 202547 min

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?

November 6, 202538 min

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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