Business Legacy

Legacy Planner For Serial Entrepreneurs | Strategic Advisor
  • 5.0 (14)
  • ENTREPRENEURSHIP
  • UPDATED WEEKLY

The Legacy Podcast is a series of conversations with business owners who share their journey to financial freedom and the legacy they want to leave for the next generation. Their stories are empowering, educational, and encouraging.

  1. Breaking the Loop of Stress and Self Doubt

    4D AGO

    Breaking the Loop of Stress and Self Doubt

    Confidence isn't a personality trait, it's a system you can train. In this episode of the Business Legacy Podcast, Paul Dio sits down with mindset and confidence expert Natalie Plamondon-Thomas to explore how our brain creates stress, doubt, and emotional loops and how to interrupt them. Natalie shares the neuroscience behind confidence, the difference between the logical mind and unconscious mind, and why most people accidentally program themselves for stress. Through powerful metaphors and practical tools, she explains how to rewrite internal dialogue, break anxiety cycles, and access peak performance on demand. From executives under pressure to parents overwhelmed by daily stress, this episode is a masterclass in emotional regulation, mindset training, and building lasting confidence. Timestamps 00:01:15 – The gym story that launched Natalie's confidence journey 00:03:50 – Why we sabotage ourselves even when we know better 00:07:51 – The mind-body confidence connection 00:10:45 – The neuroscience of emotional loops 00:13:30 – How to exit stress cycles in under 90 seconds 00:17:45 – Anxiety vs decision-making reframed 00:22:59 – Reprogramming negative self-talk 00:26:40 – Why distractions worsen stress 00:27:29 – Where to learn more about Natalie Episode Resources Natalie's 22-question mindset reset tool: https://thinkyourself.com/22questions Legacy Podcast: For more information, visit https://businesslegacypodcast.com Leave a Review: We'd love your feedback on your preferred podcast platform. For more information: Visit businesslegacypodcast.com for show notes and additional resources.

    28 min
  2. Creating Space Where People Feel Seen and Heard

    JAN 26

    Creating Space Where People Feel Seen and Heard

    What happens when culture becomes the foundation of your business not just a marketing tactic? In this episode of the Business Legacy Podcast, Paul Dio sits down with Evan Marshall, COO of Black Menswear, a cultural impact agency that began as a visual storytelling project and evolved into a nationwide movement and top-of-funnel agency for brands. Evan breaks down the power of enclothed cognition how what we wear shapes how we think and how that idea became the thread that ties together fashion, identity, and community for Black and brown audiences. From viral flash mobs to global brand campaigns, Black Menswear is redefining what it means to speak to not at underrepresented communities. Whether you're a founder, marketer, or leader trying to understand how to build with intention, this episode delivers sharp insights on culture, strategy, and scaling impact without losing authenticity. Timestamps 00:01:00 – The Origin of Black Menswear and Cultural Storytelling 00:02:40 – Why Clothing and Identity Are Deeply Connected 00:04:05 – What the Browning of America Means for Brands 00:06:00 – Meeting Communities Where They Are (Not Where You Want Them to Be) 00:08:52 – Communicating Across Subcultures and Global Events 00:11:38 – How the Workforce Has Changed Post-COVID 00:14:04 – What Lean and Mighty Culture Really Looks Like 00:15:45 – Ideal Clients and Brand Partnerships 00:17:53 – The Real Legacy: Impacting Lives Through Space and Belonging 00:19:35 – Where to Connect with Evan and Black Menswear   Enjoyed this episode? Leave us a review here → Apple Podcasts Thank you for listening to this episode of the Legacy Podcast. Great reviews help us reach more legacy-minded entrepreneurs just like you.   Episode Resources Connect with Evan Marshall here: https://www.linkedin.com/in/ebennettmarshall/ Legacy Podcast: For more information, visit https://businesslegacypodcast.com Leave a Review: We'd love your feedback on your preferred podcast platform For more information: Visit businesslegacypodcast.com for show notes and additional resources.

    21 min
  3. Choose Growth Over Comfort and Build a Lifeswitch

    JAN 19

    Choose Growth Over Comfort and Build a Lifeswitch

    What if your biggest failure turned into the moment that defined your legacy? In this episode of the Legacy Podcast, host Paul Dio sits down with Joel Steele, entrepreneur, speaker, and author of LifeSwitch. From restaurant collapse to financial success, Joel shares how flipping his "life switch" transformed his mindset, purpose, and trajectory. Now, through his book and mission, he's helping others find the power within themselves to do the same. Joel unpacks the turning points that shaped him from navigating debt to redefining fulfillment beyond financial wins. He dives into how tuning into your emotions, building physical discipline, and reigniting purpose are the real keys to building a meaningful legacy. Whether you're stuck in the dark or already chasing the next mountain, this episode will challenge and inspire you to live life "on" with clarity, energy, and conviction. Timestamps 00:01:00 – Joel's sports icons and the pursuit of greatness 00:03:00 – Why he wrote LifeSwitch despite business success 00:06:30 – The metaphor of flipping your life switch and finding clarity 00:09:45 – LifeSwitch moments: failure, debt, and reinvention 00:13:30 – Transitioning from restaurant failure to financial services 00:16:30 – How fitness helped him manage stress, anxiety, and focus 00:18:30 – Building peace of mind for clients, not just portfolios 00:20:00 – Why passion and purpose matter more than profit 00:21:30 – Committing to a $1M charitable donation through book sales   Enjoyed this episode? Leave us a review here → Apple Podcasts Thank you for listening to this episode of the Legacy Podcast. Great reviews help us reach more legacy-minded entrepreneurs just like you.   Episode Resources Connect with Joel Steele here: https://bookjoelsteele.com Legacy Podcast: For more information, visit https://businesslegacypodcast.com Leave a Review: We'd love your feedback on your preferred podcast platform. For more information: Visit businesslegacypodcast.com for show notes and additional resources.

    23 min
  4. Helping People Sleep Better with Data-Driven Reviews

    12/29/2025

    Helping People Sleep Better with Data-Driven Reviews

    What happens when you mix analytical rigor with an everyday product like a mattress? You get NapLab, a data-driven review site created by Derek Hales, whose mission is to help people sleep better by eliminating the guesswork behind mattress shopping. In this episode of the Legacy Podcast, host Paul Dio sits down with Derek to explore how a personal frustration with mattress shopping led to a full-time career in objective sleep product testing. What started as a weekend side project quickly turned into one of the most trusted mattress review platforms online. Derek walks through his meticulous testing process, the surprising metrics that matter most in choosing a mattress, and how NapLab's data-backed approach differentiates them in an industry that's often dominated by biased affiliate marketing. You'll also hear why he believes sleep is the foundation of health and how helping others rest better is his true legacy. Timestamps 00:01:00 – How Derek's mattress shopping turned into a review business 00:03:15 – NapLab's testing process and lab setup explained 00:06:45 – Staying unbiased in a biased, money-driven review world 00:08:40 – How they use data to validate and score mattress quality 00:10:30 – The 3 most important questions when choosing a mattress 00:12:00 – Industry trends NapLab is influencing through objective testing 00:13:45 – How often people replace mattresses and lifecycle decisions 00:15:00 – Managing couples with different sleep preferences 00:17:00 – Why past mattress experience matters in future recommendations 00:18:00 – Derek's motivation: helping people rest, restore, and heal 00:19:35 – Where to learn more and get a personalized recommendation   Connect with Derek 🌐 Website: https://naplab.com 📄 Personalized Mattress Recommendation: naplab.com/recommendation (24-hr response)   Enjoyed this episode? Leave us a review here → Apple Podcasts Thank you for listening to this episode of the Legacy Podcast. Great reviews help us reach more legacy-minded entrepreneurs just like you. Episode Resources Connect with Derek here and find more about what he does: https://naplab.com Legacy Podcast: For more information about the Legacy Podcast and its co-hosts, visit https://businesslegacypodcast.com Leave a Review: If you enjoyed the episode, leave a review and rating on your preferred podcast platform. For more information: Visit https://businesslegacypodcast.com to access the show notes and additional resources on the episode.

    20 min
  5. Redefining Professional Outreach in the Age of AI

    12/22/2025

    Redefining Professional Outreach in the Age of AI

    Is cold email dead? Not even close you're just doing it wrong. In this episode of the Legacy Podcast, host Paul Dio speaks with Adam Rosen, founder and CEO of Email Outreach Company (EOC), a service helping startups and businesses scale their outreach through strategic, professional cold email. From landing Fortune 500 clients like Amazon and Bank of America to getting replies from Mark Cuban and Ajay Banga, Adam shares real stories that prove email is still one of the most powerful tools in business if you know how to use it. He breaks down what's changed (and what hasn't) in the email landscape, especially after the crackdown by Google and Microsoft on poor practices. You'll learn why most emails go ignored, what really makes the best open rates, and how to write with the kind of care that earns time on someone's calendar not a spot in the spam folder. Whether you're in B2B sales, lead generation, or trying to build partnerships from scratch, Adam delivers a crash course on doing cold email the right way built on value, credibility, and deep customer understanding. Timestamps 00:01:07 – How Adam stumbled into email and turned it into a business 00:02:45 – Cold emailing Mark Cuban and getting replies from execs 00:04:00 – Why most outreach fails due to poor offer articulation 00:06:15 – How to research and write for high-level prospects 00:09:00 – Professionalism in outreach and how to stand out 00:10:50 – Why Adam stuck with email despite newer channels 00:12:15 – How AI is accelerating the pace of change in cold email 00:13:30 – Outdated tactics and what no longer works in 2024 00:15:00 – Managing hundreds of inboxes with new tech 00:16:50 – Where to learn more and sign up for Adam's newsletter   Connect with Adam  🌐 Website: https://eocworks.com 📩 Email: adam@eocworks.com 📰 Newsletter: Cold Email Tips & Strategy (Free Signup)   Enjoyed this episode? Leave us a review here → Apple Podcasts Thank you for listening to this episode of the Legacy Podcast. Great reviews help us reach more legacy-minded entrepreneurs just like you. Episode Resources Connect with Adam here and find more about what he does: https://eocworks.com Legacy Podcast: For more information about the Legacy Podcast and its co-hosts, visit https://businesslegacypodcast.com Leave a Review: If you enjoyed the episode, leave a review and rating on your preferred podcast platform. For more information: Visit https://businesslegacypodcast.com to access the show notes and additional resources on the episode.

    18 min
  6. Rethinking Water Quality and Community

    12/15/2025

    Rethinking Water Quality and Community

    What happens when a software founder returns to her roots in Maine and sees clean water as the foundation for local economic development? In this episode of the Legacy Podcast, host Paul Dio speaks with Jen Millard, co-founder and CEO of Maine Love, a growing water brand with a mission far bigger than hydration. After years leading tech companies and consumer product startups, Jen returned to her home state to build something that mattered not just a brand, but a vehicle for job creation, sustainability, and local reinvestment. From repurposing idle breweries to creating a supply chain that keeps economics in-state, Maine Love represents a fresh model of what it means to build a legacy-driven business. Jen shares how her liberal arts education and deep Maine roots shaped her entrepreneurial vision, how Gen Z is redefining consumption with health and intention, and why being radically kind is just as essential as product-market fit. If you've ever wondered how to turn a simple idea like water into a scalable, meaningful brand, this conversation will quench your curiosity. Timestamps 00:01:10 – How the idea for Maine Love was born 00:03:00 – Jen's background in retail, tech, and personalization 00:05:30 – Launching with 5 SKUs and breaking into 500+ retail doors 00:06:50 – Becoming an entrepreneur after selling her first company 00:08:00 – Why Gen Z and moms are drawn to Maine Love 00:09:00 – The surprising challenges of selling water in a state full of it 00:11:00 – Water quality, municipal sourcing, and economic reinvestment 00:13:00 – Jen's vision for job creation and retaining Maine's next generation 00:14:30 – How to buy, subscribe, and find Maine Love near you Enjoyed this episode? Leave us a review here → Apple Podcasts Thank you for listening to this episode of the Legacy Podcast. Great reviews help us reach more legacy-minded entrepreneurs just like you. Episode Resources Connect with Jen here and find more about what she does: https://mainelove.com Legacy Podcast: For more information about the Legacy Podcast and its co-hosts, visit https://businesslegacypodcast.com Leave a Review: If you enjoyed the episode, leave a review and rating on your preferred podcast platform. For more information: Visit https://businesslegacypodcast.com to access the show notes and additional resources on the episode.

    16 min

  7. 12/08/2025

    Why Connection and Curiosity Drive Business Growth

    How do you turn a childhood paper route into a billion-dollar vision rooted in purpose and positivity? In this episode of the Legacy Podcast, host Paul Dio sits down with Peter Bradford, serial entrepreneur and founder of Cash Network LLC, to explore his journey from domain-flipping in the late '90s to launching a pet insurance company with heart. Peter's story is a testament to how curiosity, adaptability, and an intrinsic desire to "be better" can evolve into meaningful legacy-building. He shares how early lessons in efficiency, pattern recognition, and people-watching laid the foundation for building successful ventures across affiliate marketing, law, and pet insurance. But this episode goes deeper than business mechanics. Paul and Peter reflect on fatherhood, the definition of happiness, and what it really means to leave a legacy that outlives you. From helping his daughter grow into a leadership role within the family business, to launching a nonprofit-driven Be Better Movement, Peter's mission is clear: create scalable businesses that also make humans better. Whether you're an entrepreneur, a parent, or someone striving for more alignment in your life, this episode will inspire you to see business not just as a tool for profit, but for impact. Timestamps 00:01:10 – Peter's Passion for Connecting People 00:05:00 – Early Lessons from Paper Routes and Bike Businesses 00:10:00 – From Domain Flipping to Data-Driven Lead Gen 00:14:00 – The Birth of Cash Network and Scaling Through Vertical Insights 00:18:00 – Launching a Law Firm and Pet Insurance Brand 00:21:00 – Adapting to Human Behavior and Tech in Lead Gen 00:26:00 – Involving His Daughter in the Business and Defining Happiness 00:30:00 – Work-Life Balance and the Reality of Entrepreneurial Parenting 00:35:00 – Storytelling at Bedtime and Creating Deep Connection 00:39:00 – The "Be Better" Movement: From VP Advice to Nonprofit Mission 00:44:00 – Peter's Vision of Legacy and What He Wants to Be Remembered For 00:48:00 – Where to Connect with Peter and Learn More   Enjoyed this episode? Leave us a review here → Apple Podcasts Thank you for listening to this episode of the Legacy Podcast. Great reviews help us reach more legacy-minded entrepreneurs just like you. Episode Resources Be Better Movement Book – Coming soon Episode Resources: Connect with Peter here and find more about what he does: https://www.linkedin.com/in/peter-bradford/ Legacy Podcast: For more information about the Legacy Podcast and its co-hosts, visit https://businesslegacypodcast.com Leave a Review: If you enjoyed the episode, leave a review and rating on your preferred podcast platform.

    38 min
  8. From Disruption to Advantage with Futurist Insights

    11/24/2025

    From Disruption to Advantage with Futurist Insights

    What if you could anticipate the future with certainty, turning potential challenges into opportunities? On this episode of the Legacy Podcast, we explore this compelling idea with Daniel Burrus, a renowned futurist, author, and speaker. Dive into the art of foresight as Burrus explains the power of combining anticipatory strategies with an understanding of hard and soft trends. Hard trends are inevitable future certainties such as technological advancements, while soft trends are mutable assumptions. Together, we uncover how identifying these trends can transform both personal growth and business strategy, enabling you to stay ahead of disruptions rather than merely reacting to them. Join us as we traverse the fascinating landscape of technology adoption and mindset shifts, with stories ranging from the bustling tech scenes overseas to the inspiring transformation of Lawton, Oklahoma, into a tech and STEM education hub. Throughout our conversation, we emphasize the importance of a proactive mindset and the role trust plays in evolving professions like accounting and auditing. We also tackle the significant impact of AI on jobs and the necessity of continuous learning to remain relevant in a swiftly changing world. Tune in for insights and resources that can help you harness these ideas for a future-ready career, and prepare to challenge your views on scarcity and abundance. Timestamps 00:00:00 - Introduction and Welcome to the Legacy Podcast   00:01:05 - Anticipatory vs. Reactionary Trends: Understanding the Basics   00:13:00 - Turning Soft Trends Into Opportunities: Strategies for Business Growth   00:16:00 - Technology Adoption Trends and Mindset Shifts: Global Perspectives   00:22:00 - Daniel Burrus on the Power of Foresight and Anticipatory Thinking   00:30:00 - The "Skip It" Principle: Bypassing Traditional Hurdles   00:35:00 - AI's Impact on Job Markets: Adapting to Technological Changes   00:40:00 - Embracing Change for a Future-Ready Mindset: Preparing for Tomorrow   00:45:00 - Building a Legacy: Insights from Daniel Burrus   00:50:00 - Closing Remarks and Where to Find More Resources on Foresight   Episode Resources: Connect with Daniel here and find more out about what he does: https://www.burrus.com/ Legacy Podcast: For more information about the Legacy Podcast and its co-hosts, visit businesslegacypodcast.com. Leave a Review: If you enjoyed the episode, leave a review and rating on your preferred podcast platform. For more information: Visit businesslegacypodcast.com to access the shownotes and additional resources on the episode.

    22 min
See All (246)

5
out of 5
14 Ratings

About

The Legacy Podcast is a series of conversations with business owners who share their journey to financial freedom and the legacy they want to leave for the next generation. Their stories are empowering, educational, and encouraging.

Information

  • Creator
    Legacy Planner For Serial Entrepreneurs | Strategic Advisor
  • Years Active
    2021 - 2026
  • Episodes
    246
  • Rating
    Clean
  • Copyright
    © Copyright 2022 Kirk Chisholm
  • Show Website
    Business Legacy