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. Helping People Sleep Better with Data-Driven Reviews

    5D AGO

    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
  2. 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
  3. 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

  4. 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
  5. 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
  6. Integrating Vitamins into Daily Habits

    11/17/2025

    Integrating Vitamins into Daily Habits

    What if your daily brushing routine could do more than just clean your teeth? Join us as we chat with Vladimir, the visionary co-founder and CEO of Better Better, who is transforming oral care into a nutritional powerhouse. After overcoming cancer and grappling with the demands of daily supplements, Vladimir had a breakthrough idea: infuse toothpaste with essential vitamins and minerals to support both oral health and overall well-being. Discover the compelling story behind the development of nutrient-enriched toothpaste and how this innovative concept leverages the simple habit of brushing to deliver health benefits, potentially minimizing the reliance on traditional supplements. In this episode, we dive into the intricate process of selecting the right vitamins, such as D, B12, zinc, and E, to address common deficiencies while maintaining a pleasant brushing experience. Vladimir also shares insights on the evolution of Better Better's product line, shaped by invaluable customer feedback on taste, texture, and mouthfeel. Explore the challenges faced in manufacturing, the strategic shifts in production partners, and the exciting future of Better Better as they plan to expand their offerings with natural floss and bamboo toothbrushes. Listen in to uncover how this pioneering brand aims to make a positive impact on both individual health and the environment, ensuring that your everyday habits contribute to a healthier lifestyle. Timestamps 00:00:00 - Introduction and Welcome to Business Legacy Podcast   00:00:11 - Meet Matthew Wessels: Real Estate and Tax Advisory Innovator   00:00:37 - Matthew's New Hampshire Roots and Education at Bentley University   00:01:20 - Transition from Corporate Accounting to Real Estate Investment   00:02:45 - Building Wessels Realty and Tax Advisors: A Multifaceted Approach   00:04:10 - The Unique Blend of CPA Expertise and Real Estate Development   00:05:25 - The Complexity and Opportunities in Real Estate and Tax Advisory   00:06:30 - Market Fluctuations and Resilience in Massachusetts Rental Properties   00:07:55 - Political and Economic Influences on the Housing Market   00:09:10 - Trends in Homeownership and Investment Property Challenges   00:10:30 - Matthew's Role in Educating and Mentoring Aspiring Investors   00:11:09 - Real Estate Market Insights and Strategies   00:12:05 - Overcoming the Fear of Property Investment   00:13:30 - The Impact of Market Shifts on Cash Flow and Property Value   00:14:40 - Balancing Professional Growth and Personal Life   00:15:50 - Matthew's Reflections on Fatherhood and Work-Life Balance   00:17:10 - Legacy, Values, and the Courage to Follow a Unique Path   00:18:05 - Navigating Work-Life Balance and Legacy   00:19:00 - Emphasizing Happiness, Generosity, and Authenticity   00:20:30 - Matthew's Advice: Embrace Being Different and Follow Your Own Path   00:21:45 - Closing Thoughts and Where to Learn More About Matthew Wessels   00:22:45 - Conclusion and Final Thoughts from Paul Dio   00:23:30 - Closing Remarks and Invitation to Leave a Review Episode Resources: Connect with Vladimir here and find more out about what they do: https://www.betterandbetter.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.

    21 min
  7. The Intersection of Real Estate and Tax Advisory

    10/27/2025

    The Intersection of Real Estate and Tax Advisory

    Matthew Wessels, partner at Wessels Realty and Tax Advisors, takes center stage as he shares his compelling journey from the hills of New Hampshire to carving a unique niche in the real estate and tax advisory world. Matthew's story is a testament to the power of combining passions, as he skillfully marries his accounting background with a fervor for real estate development. Our conversation uncovers how he transitioned from the corporate treadmill to co-purchasing his first property, igniting a career that now stands at the intersection of real estate analysis, general contracting, and specialized tax advisory services. Matthew's insights into the Massachusetts rental market showcase both the challenges and opportunities that come with navigating market shifts, political influences, and evolving investment strategies. In a deeper exploration, we reflect on the balance between professional success and personal fulfillment. Matthew opens up about how fatherhood reshaped his priorities, leading to a transformation in his work-life balance through automation and delegation. His reflections on legacy, infused with values of authenticity, courage, and generosity, offer listeners a roadmap to crafting a meaningful life beyond societal expectations. This episode is a treasure trove of wisdom for those eager to learn from a visionary who has successfully integrated personal growth with professional achievement, all while maintaining the courage to follow his distinctive path. Timestamps 00:00:00 - Introduction and Welcome to Business Legacy Podcast   00:00:11 - Meet Matthew Wessels: Real Estate and Tax Advisory Innovator   00:00:37 - Matthew's New Hampshire Roots and Education at Bentley University   00:01:20 - Transition from Corporate Accounting to Real Estate Investment   00:02:45 - Building Wessels Realty and Tax Advisors: A Multifaceted Approach   00:04:10 - The Unique Blend of CPA Expertise and Real Estate Development   00:05:25 - The Complexity and Opportunities in Real Estate and Tax Advisory   00:06:30 - Market Fluctuations and Resilience in Massachusetts Rental Properties   00:07:55 - Political and Economic Influences on the Housing Market   00:09:10 - Trends in Homeownership and Investment Property Challenges   00:10:30 - Matthew's Role in Educating and Mentoring Aspiring Investors   00:11:09 - Real Estate Market Insights and Strategies   00:12:05 - Overcoming the Fear of Property Investment   00:13:30 - The Impact of Market Shifts on Cash Flow and Property Value   00:14:40 - Balancing Professional Growth and Personal Life   00:15:50 - Matthew's Reflections on Fatherhood and Work-Life Balance   00:17:10 - Legacy, Values, and the Courage to Follow a Unique Path   00:18:05 - Navigating Work-Life Balance and Legacy   00:19:00 - Emphasizing Happiness, Generosity, and Authenticity   00:20:30 - Matthew's Advice: Embrace Being Different and Follow Your Own Path   00:21:45 - Closing Thoughts and Where to Learn More About Matthew Wessels   00:22:45 - Conclusion and Final Thoughts from Paul Dio   00:23:30 - Closing Remarks and Invitation to Leave a Review   Episode Resources: Connect with Matthew here and find more out about what they do: https://www.wesselsrealtyandtaxadvisors.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.

    25 min
  8. Harnessing Rhythm for Inspirational Leadership

    10/13/2025

    Harnessing Rhythm for Inspirational Leadership

    Transformative Leadership and Business Innovation: Natalie Spiro's journey from Johannesburg to the CEO of Drum Cafe North America illustrates the power of adaptability and innovation in leadership. Her story highlights how interactive drumming became a transformative tool for team development and corporate engagement, leading to a unique business model that turns energy into inspiration. Resilience in the Face of Adversity: The episode delves into Natalie's strategic pivots during the COVID-19 pandemic, showcasing her resilience as she transitioned from live events to virtual operations. Her ability to navigate challenges, consolidate resources, and embrace personal growth serves as a testament to her strength and determination in maintaining business continuity. Strategic Growth and Team Development: As Drum Cafe scaled, Natalie focused on building a team-managed business, emphasizing the importance of strategic partnerships and logistical planning. Her experience in hiring and training facilitators, managing expenses, and adapting to corporate needs offers valuable insights for entrepreneurs looking to expand their operations. Legacy of Cultural Humility and Education: Natalie discusses her vision of leaving a legacy through a non-profit initiative aimed at improving social-emotional learning in schools. Her commitment to cultural humility and fostering future leaders reflects her passion for creating meaningful impact and inspiring the next generation. Tune in to explore Natalie's inspiring leadership journey, learn from her experiences in overcoming business challenges, and discover how she continues to pioneer a path of transformational leadership in uncertain times. Timestamps 00:00:00 - Introduction and Welcome to Business Legacy Podcast   00:01:10 - Natalie's Journey from Johannesburg to the U.S.   00:02:30 - Discovering Purpose Through Vision Exercise   00:04:00 - Encounter with Motorola and the Birth of Drum Cafe North America   00:06:15 - The Transformative Power of Interactive Drumming   00:08:30 - Importance of Valuing Work and Establishing Business Model    00:11:45 - Transitioning to Virtual Operations and Personal Development   00:13:00 - Rebuilding the Business Post-COVID   00:15:00 - Managing Strategic Partnerships and Scaling Challenges   00:17:30 - Adapting to Changes in Team and Corporate Needs   00:19:00 - Overcoming Adversity and Finding Inspiration   00:21:00 - The Impact of Cultural Humility and Ancestral Wisdom   00:23:30 - Natalie's Vision for a Non-Profit and Legacy   00:25:00 - Contact Information and Closing Remarks Episode Resources: Connect with Natalie here and find more out about Drum cafe: https://drumcafenorthamerica.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.

    24 min
See All (243)

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 - 2025
  • Episodes
    243
  • Rating
    Clean
  • Copyright
    © Copyright 2022 Kirk Chisholm
  • Show Website
    Business Legacy