Unmasked: The CEO Files

Leanne Bucaro, Alan McLaren
  • 0.0 (0)
  • Entrepreneurship
  • Biweekly

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.

  1. Oct 7

    Make Investors Compete For The Deal With Guest Roy Moëd

    What does it really take to raise capital, build a resilient business, and make investors compete for the deal? In this episode of UNMASKED: The Capital Raise Files, Alan sits down with entrepreneur, CEO and LifeBook Memoirs co-founder Roy Moëd to explore decades of entrepreneurial experience, fundraising lessons, business reinvention, and the importance of finding investors who believe in both the opportunity and the mission. In this episode, we explore: ➡️ How to create competition among investors ➡️ Why investor alignment and trust matter ➡️ How to handle pressure and challenging questions ➡️ Using AI to stress-test your pitch and prepare for investors ➡️ Why your legacy matters beyond money and business success Roy has chronicled the journeys of 67 startups and, through LifeBook Memoirs, has helped create more than 2,000 private autobiographies and memoirs. A global serial entrepreneur and longtime YPO member, Roy brings a unique perspective on business, storytelling, leadership and building something that lasts. His reminder is simple: raising money is only ever a means, what lasts is what you build with it. 🔗 Connect with Roy Moëd on LinkedIn: https://www.linkedin.com/in/roy-mo%C3%ABd-lifebook-memoirs/ _____ UNMASKED: The Capital Raise Files: Real stories from CEOs who have raised capital, so other leaders can move through the process with more clarity, confidence and fewer wasted rooms. In this special series of Unmasked: The CEO Files, we sit down with CEOs and founders who have actually lived through a capital raise to uncover what happened behind the deck, the numbers and the polished story. Why was the money needed? How did they approach the market? How many investor rooms did it take? What questions created pressure? Where did trust form, and where did resistance show up? Most importantly, what would they do differently if they had to raise again? Because raising capital is never just about the business opportunity, the financial model or the pitch deck. Investors are evaluating the leader in the room, too. How clearly can a CEO communicate under pressure? Can they build trust? Can they respond when challenged? And how does the way they show up influence the outcome? The Capital Raise Files goes beyond fundraising advice to explore the lived experience of raising capital, giving CEOs and founders practical insight they can take into their own investor rooms. If you’re preparing to raise capital, considering M&A or moving toward an IPO, these are the real stories worth hearing. We’re researching why some capital raises move quickly in fewer investor meetings while others drag through extra meetings and follow-up. If you’ve raised capital, we’d value your input. It takes under a minute and all responses are aggregated and never attributed. Click here: https://tally.so/r/68yyZB If you are interested in the findings let us know at alan@strataoriginals.com 🔗 Connect with STRATA Website: www.strataoriginals.com LinkedIn: https://www.linkedin.com/company/80453987

  2. Oct 7

    Capital With Conviction: Why Investor Alignment Matters With Guest Wayne Hennessy-Barret

    What does it really take to build a mission-driven business, raise capital, and stay true to your values when the pressure is on? In this episode of UNMASKED: The Capital Raise Files, Alan sits down with Wayne Hennessy-Barrett, Founder and Executive Chairman of 4G Capital, a fintech company helping small businesses across Africa access the working capital they need to grow. Wayne shares his journey from 17 years in the British Army to building a business focused on democratizing wealth creation for entrepreneurs in Kenya and Uganda. In this episode, we explore: ➡️ How Wayne's military career shaped his approach to leadership and decision-making ➡️ The journey from the British Army to building 4G Capital ➡️ What investors really want to know during a capital raise ➡️ Why customer trust and company values matter when times get tough ➡️ Wayne's advice for founders building sustainable, mission-driven businesses The conversation dives into fundraising, leadership, investor alignment and the difficult decisions that come with building a growing company. Wayne also shares what he learned from raising capital during COVID, why choosing the right investors matters, and how staying focused on customers and values can shape a stronger business. 🔗 Connect with Wayne on LinkedIn: https://www.linkedin.com/in/waynehennessybarrett/?isSelfProfile=false _______ UNMASKED: The Capital Raise Files: Real stories from CEOs who have raised capital, so other leaders can move through the process with more clarity, confidence and fewer wasted rooms. In this special series of Unmasked: The CEO Files, we sit down with CEOs and founders who have actually lived through a capital raise to uncover what happened behind the deck, the numbers and the polished story. Why was the money needed? How did they approach the market? How many investor rooms did it take? What questions created pressure? Where did trust form, and where did resistance show up? Most importantly, what would they do differently if they had to raise again? Because raising capital is never just about the business opportunity, the financial model or the pitch deck. Investors are evaluating the leader in the room, too. How clearly can a CEO communicate under pressure? Can they build trust? Can they respond when challenged? And how does the way they show up influence the outcome? The Capital Raise Files goes beyond fundraising advice to explore the lived experience of raising capital, giving CEOs and founders practical insight they can take into their own investor rooms. If you’re preparing to raise capital, considering M&A or moving toward an IPO, these are the real stories worth hearing. We’re researching why some capital raises move quickly in fewer investor meetings while others drag through extra meetings and follow-up. If you’ve raised capital, we’d value your input. It takes under a minute and all responses are aggregated and never attributed. Click here: https://tally.so/r/68yyZB If you are interested in the findings let us know at alan@strataoriginals.com 🔗 Connect with STRATA Website: www.strataoriginals.com LinkedIn: https://www.linkedin.com/company/80453987

  3. Oct 6

    Look Again: Changing the Way We See the World with Guest Muraly Srinarayanathas

    What happens when your identity, culture, and experiences across borders become a business advantage? In this episode of UNMASKED: The CEO Files, Alan McLaren is joined by global strategist, entrepreneur, and third culture leader Muraly Srinarayanathas to explore cultural intelligence, global expansion, entrepreneurship, and the ideas behind 3 magazine. In this episode, we explore: ➡️ How becoming a third culture entrepreneur shaped Muraly’s leadership ➡️ Why values matter when making difficult business decisions ➡️ The story behind 3 magazine and its global vision ➡️ What Canadian businesses can learn from international markets and Africa ➡️ Why taking a second look can challenge assumptions and create new opportunities Muraly is Chairman and Co-Founder of 369 Global, Chairman of Computek College, Founder and Publisher of 3 magazine, and Host of the Third Culture Leaders Podcast. 🔗 Connect with Muraly on LinkedIn: https://www.linkedin.com/in/muralys/ ______ 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. If investor trust isn’t building fast enough, your raise may require more conversations than it should. Try the Capital Room Scan: https://stratacapitalroomscan.s.gy/origRm 🔗 Connect with STRATA Website: www.strataoriginals.com LinkedIn: https://www.linkedin.com/company/strataoriginals/posts/?feedView=all

  4. Oct 6

    Raising Capital Is A Truth Serum: What The Room Reveals About The Leader With Guest David Lovejoy

    What happens when raising capital becomes a truth serum for your business? In this episode of Unmasked: The Capital Raise Files, Alan McLaren sits down with David Lovejoy, Founder & CEO of CoachFinder.ai, to talk about the realities of fundraising, the investor questions that exposed blind spots, and how those conversations helped reshape his business. In this episode, we explore: ➡️ Why founders should start raising capital earlier than they think ➡️ What difficult investor questions can reveal about your business ➡️ How investor conversations helped reshape CoachFinder’s direction ➡️ Why “no” and investor ghosting can still be valuable learning opportunities ➡️ What fundraising taught David about leadership, humility and self-awareness David also shares how CoachFinder is building a measurement layer for leadership development and coaching, helping organizations better understand what is working, for whom, and why. _______ UNMASKED: The Capital Raise Files: Real stories from CEOs who have raised capital, so other leaders can move through the process with more clarity, confidence and fewer wasted rooms. In this special series of Unmasked: The CEO Files, we sit down with CEOs and founders who have actually lived through a capital raise to uncover what happened behind the deck, the numbers and the polished story. Why was the money needed? How did they approach the market? How many investor rooms did it take? What questions created pressure? Where did trust form, and where did resistance show up? Most importantly, what would they do differently if they had to raise again? Because raising capital is never just about the business opportunity, the financial model or the pitch deck. Investors are evaluating the leader in the room, too. How clearly can a CEO communicate under pressure? Can they build trust? Can they respond when challenged? And how does the way they show up influence the outcome? The Capital Raise Files goes beyond fundraising advice to explore the lived experience of raising capital, giving CEOs and founders practical insight they can take into their own investor rooms. If you’re preparing to raise capital, considering M&A or moving toward an IPO, these are the real stories worth hearing. We’re researching why some capital raises move quickly in fewer investor meetings while others drag through extra meetings and follow-up. If you’ve raised capital, we’d value your input. It takes under a minute and all responses are aggregated and never attributed. Click here: https://tally.so/r/68yyZB If you are interested in the findings let us know at alan@strataoriginals.com 🔗 Connect with STRATA Website: www.strataoriginals.com LinkedIn: https://www.linkedin.com/company/80453987

  5. Sep 25

    When Raising Capital Becomes a Test of the Entrepreneur with Guest Peter Cimoroni

    What does it really take to raise capital, build investor trust, and scale a CPG brand? In this episode of UNMASKED: The Capital Raise Files, Alan McLaren sits down with Peter Cimoroni, CEO and Founder of AVOGO Foods, to talk about the realities of raising money and building a consumer brand in today’s market. With more than 40 years of professional experience, Peter brings a unique perspective on entrepreneurship, customer marketing, financial analysis, and food innovation. At AVOGO Foods, he is focused on creating healthy, avocado-based products with minimal ingredients and maximum flavour while building a brand designed to grow. Peter shares his experience raising capital, approaching investors, navigating the challenges of scaling a CPG business, and hearing the question investors want answered: where is the scale? He also discusses why transparency, curiosity, credibility, and knowing exactly where your capital is going can make a difference when you step into the investor room. In this episode, we explore: ➡️ Why raising capital for CPG and food brands can be challenging in today’s market ➡️ What investors are really looking for when evaluating a founder and their growth plan ➡️ Peter’s experience raising a $1 million round after speaking with 300 people ➡️ Why transparency around how capital will be used matters to investors ➡️ How founder credibility, curiosity, and mindset can shape investor conversations For CEOs and founders preparing to raise capital, this conversation offers a candid look at what happens before the cheque is written, and what it takes to turn an idea and a product into a scalable business.

  6. Sep 22

    The Operator’s Reality of Raising Capital with Guest Eric Vest

    What does it really take to raise capital when you’re not coming from the traditional finance world? In this episode of UNMASKED: The Capital Raise Files, Alan McLaren sits down with Eric Vest, Founder & CEO of Yellowwood and Founder & Managing Partner of Y Capital, to unpack what more than 30 years of building, growing and selling technology companies has taught him about people, technology and capital. In this episode, we explore: ➡️ Building credibility when entering the capital markets as an operator ➡️ The role of relationships, trust and reputation in raising capital ➡️ Finding the right investors and building a strong cap table ➡️ What Eric learned from nearly 350 investor conversations ➡️ Why going from zero to one can be the hardest part of a capital raise Eric shares the realities of raising $15 million, what surprised him along the way, and how his experience as an operator, investor and entrepreneur has shaped the way he approaches capital, technology and growth. _______ UNMASKED: The Capital Raise Files: Real stories from CEOs who have raised capital, so other leaders can move through the process with more clarity, confidence and fewer wasted rooms. In this special series of Unmasked: The CEO Files, we sit down with CEOs and founders who have actually lived through a capital raise to uncover what happened behind the deck, the numbers and the polished story. Why was the money needed? How did they approach the market? How many investor rooms did it take? What questions created pressure? Where did trust form, and where did resistance show up? Most importantly, what would they do differently if they had to raise again? Because raising capital is never just about the business opportunity, the financial model or the pitch deck. Investors are evaluating the leader in the room, too. How clearly can a CEO communicate under pressure? Can they build trust? Can they respond when challenged? And how does the way they show up influence the outcome? The Capital Raise Files goes beyond fundraising advice to explore the lived experience of raising capital, giving CEOs and founders practical insight they can take into their own investor rooms. If you’re preparing to raise capital, considering M&A or moving toward an IPO, these are the real stories worth hearing. We’re researching why some capital raises move quickly in fewer investor meetings while others drag through extra meetings and follow-up. If you’ve raised capital, we’d value your input. It takes under a minute and all responses are aggregated and never attributed.

  7. Sep 10

    What You Learn After Thousands of Investor Rooms With Brandon Davis, Trek One Capital.

    UNMASKED: The Capital Raise Files: Real stories from CEOs who have raised capital, so other leaders can move through the process with more clarity, confidence and fewer wasted rooms. In this special series of Unmasked: The CEO Files, we sit down with CEOs and founders who have actually lived through a capital raise to uncover what happened behind the deck, the numbers and the polished story. Why was the money needed? How did they approach the market? How many investor rooms did it take? What questions created pressure? Where did trust form, and where did resistance show up? Most importantly, what would they do differently if they had to raise again? Because raising capital is never just about the business opportunity, the financial model or the pitch deck. Investors are evaluating the leader in the room, too. How clearly can a CEO communicate under pressure? Can they build trust? Can they respond when challenged? And how does the way they show up influence the outcome? The Capital Raise Files goes beyond fundraising advice to explore the lived experience of raising capital, giving CEOs and founders practical insight they can take into their own investor rooms. If you’re preparing to raise capital, considering M&A or moving toward an IPO, these are the real stories worth hearing. We’re researching why some capital raises move quickly in fewer investor meetings while others drag through extra meetings and follow-up. If you’ve raised capital, we’d value your input. It takes under a minute and all responses are aggregated and never attributed. Click here: https://tally.so/r/68yyZB If you are interested in the findings let us know at alan@strataoriginals.com 🔗 Connect with STRATA Website: www.strataoriginals.com LinkedIn: https://www.linkedin.com/company/80453987

  8. Aug 7

    The Leadership Signal Experience with Co-CEOs Leanne Bucaro and Alan McLaren

    What if the biggest factor influencing your leadership isn't what you say, but how people experience you under pressure? In this episode of UNMASKED: The CEO Files Podcast, Alan McLaren and Leanne Bucaro explore the concept of Leadership Signal and why even the most experienced CEOs can unintentionally create friction in high-stakes conversations. Whether you're leading an executive team, presenting to a board, raising capital, speaking with investors, or navigating difficult conversations, every room has consequences. The way you show up under pressure shapes trust, alignment, and ultimately business outcomes. Alan and Leanne explain why leadership isn't just about communication skills or strategy. It's about understanding how your nervous system responds when your identity, credibility, or authority feels threatened, and how those automatic reactions influence every room you enter. Drawing on real CEO experiences, practical leadership examples, and the science behind pressure and human behaviour, this conversation challenges leaders to look beyond intention and understand the impact they create! In this episode, we explore: ➡️ Why your leadership signal matters more than your intentions in high-pressure situations. ➡️ How autopilot responses and nervous system reactions create hidden friction in leadership. ➡️ The difference between what leaders believe they're communicating and what others actually experience. ➡️ The hidden business costs of distorted leadership signals, including decision drag, lost trust, and slower execution. ➡️ How greater awareness helps leaders build trust, create alignment, and lead with greater clarity under pressure. If you've ever walked out of a meeting believing it went well, only to discover decisions stalled, trust eroded, or momentum disappeared, this episode will change how you think about leadership forever. ______________ 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. If investor trust isn’t building fast enough, your raise may require more conversations than it should. Try the Capital Room Scan: https://stratacapitalroomscan.s.gy/or... 🔗 Connect with STRATA Website: www.strataoriginals.com LinkedIn: linkedin.com/company/strataoriginals?originalSubdomain=ca

See All (68)

About

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.

Information

  • Creator
    Leanne Bucaro, Alan McLaren
  • Years Active
    2023 - 2026
  • Episodes
    68
  • Rating
    Explicit
  • Show Website
    Unmasked: The CEO Files