Legacy Planner For Serial Entrepreneurs | Strategic Advisor

Business Legacy

Business EN ↓ 281 episodes

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.

Be sure to visit the podcast's website and support the creator: sites.libsyn.com

Author

Legacy Planner For Serial Entrepreneurs | Strategic Advisor

Category

Business

Podcast website

sites.libsyn.com

Latest episode

Nov 2, 2026

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Episodes

Why Most Founders Struggle to Scale Sales and How to Fix It 20.04.2026

Every founder is great at selling—until they're not. In this episode, Summer Poletti, founder of Rise of Us, breaks down one of the most common (and costly) challenges in business growth: transitioning from founder-led sales to a scalable sales system. Summer shares her unconventional path—from growth-stage operator to coach to consultant—and how her experience across multiple business functions g...

Building a Business Without Sacrificing What Matters Most 13.04.2026

Most entrepreneurs start a business chasing freedom—but many end up recreating the same constraints they were trying to escape. In this episode, Patrick Brown, founder and CEO of Unity Communications, shares a different approach: designing a business around life first, not the other way around. Patrick opens up about leaving the corporate grind to be present for his kids—and the disciplined tradeo...

How to Unlock Capital When Banks Say No 06.04.2026

Access to capital remains one of the biggest constraints for small business owners—yet it's often misunderstood. In this episode, Adam Benowitz, founder of Vox Funding, breaks down the real reason traditional banks fail entrepreneurs—and what alternative funding models are doing differently. Adam shares how Vox Funding built a fintech-driven lending platform designed to solve one of the most criti...

Why Modern Marketing Requires More Touchpoints Than Ever 30.03.2026

What if the business you built actually gave you your life back instead of taking it? In this episode, Paul sits down with Robin Agricola, Founder and CEO of Birdhouse Marketing, who has redefined what it means to build a modern business. Running her company remotely from a sailboat, Robin shares how she intentionally designed both her business model and lifestyle to work together — not compete. W...

Building a Skincare Brand Around Community and Care 16.03.2026

In Episode 254, Paul sits down with Roberta Perry, President of Scrubs Body Skincare Products, to talk about what it means to build a brand through heart, creativity, and community. What began as an "accidental entrepreneur" story mixing product in jars at home and selling at local fairs evolved into a thriving skincare business rooted in experience, personalization, and care. Roberta shares how s...

Scaling Culture Fit with Artificial Intelligence 09.03.2026

What if artificial intelligence could actually make us more human at work? In Episode 253, Paul sits down with John Betancourt, Founder and CEO of Humantelligence, to explore how personalized AI coaching is reshaping leadership, hiring, collaboration, and workplace engagement. John's career spans global corporate leadership, executive search for private equity firms, and multiple startups. Through...

Building a Business That Creates Freedom and Impact 02.03.2026

What if the business you're building is quietly costing you the life you actually want? In Episode 252, Paul chats with Jonathan Chen, Chief Catalyst of Blue Tide Catalyst, six-time entrepreneur, and executive coach focused on helping founders build exceptional companies for exceptional lives. Jonathan shares the hard truth many entrepreneurs don't confront: revenue is not value. Eighty-five perce...

How Law Firms Scale Without Becoming the Bottleneck 23.02.2026

Why do some law firms scale effortlessly while others stay stuck even when they're getting the same advice? In Episode 251, Paul sits down with Brooke Lively, founder of Scaling Law and a fractional CFO turned EOS Implementer exclusively for law firms. Brooke shares how her data-driven analysis uncovered a surprising pattern: performance differences weren't about intelligence, strategy, or effort...

The Power of Resilience and Radical Kindness 16.02.2026

What happens when you walk away from one identity and completely reinvent your life? In this episode, Paul sits down with Nathaniel Allenby entrepreneur, circus performer, author, and founder of Cirque Quirk and The Cycle of Kindness. Nathaniel's journey is anything but conventional. From becoming an international gaming champion to cycling 28,000 miles across 10 countries, to performing as a circ...

Wellness First Interior Design for High Performing Families 09.02.2026

A home should do more than look beautiful it should support the way you live, heal, rest, and perform. In this episode of the Business Legacy Podcast, host Paul sits down with Sarah Walker, founder and principal designer of Nuance Interior Design, to explore how intentional design impacts wellness, longevity, and quality of life. Sarah shares her journey from luxury residential design and corporat...

Breaking the Loop of Stress and Self Doubt 02.02.2026

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...

Creating Space Where People Feel Seen and Heard 26.01.2026

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...

Choose Growth Over Comfort and Build a Lifeswitch 19.01.2026

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 othe...

Helping People Sleep Better with Data-Driven Reviews 29.12.2025

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-...

Redefining Professional Outreach in the Age of AI 22.12.2025

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...

Rethinking Water Quality and Community 15.12.2025

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...

Why Connection and Curiosity Drive Business Growth 08.12.2025

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, ada...

From Disruption to Advantage with Futurist Insights 24.11.2025

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 in...

Integrating Vitamins into Daily Habits 17.11.2025

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...

The Intersection of Real Estate and Tax Advisory 27.10.2025

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 uncov...

Harnessing Rhythm for Inspirational Leadership 13.10.2025

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. Resilien...

Fraud Detection and Digital Marketing In the age of AI 06.10.2025

Ready to shield your digital marketing efforts from the pervasive threat of ad fraud? Join us as we sit down with Rich Kahn, the visionary co-founder and CEO of Anura. With over two decades of expertise, Rich takes us through his journey of identifying a critical gap in the market and developing a robust ad fraud solution. From bots to malware, discover how Anura innovatively tackles fraudulent ac...

Crafting a Legacy in Luxury Real Estate 29.09.2025

Ever wondered how strategic moves can reshape your career in real estate? Join us as we uncover the journey of Harrison Polsky, the principal of Katina Homes in Dallas, and learn how his transition from a commercial analyst to a prominent figure in the Dallas real estate scene became a game-changer. Harrison unfolds his path from being a residential broker to representing builders, navigating the...

The Art of Trust and Technology 22.09.2025

What if empathy could be the cornerstone of great leadership? Join us on a transformative journey with Susan Odle, the visionary CEO of StorMagic, as she unravels the secrets behind her remarkable 30-year career in the tech industry. From her beginnings in sales to ascending to the role of CEO, Susan shares how listening and building trust have been pivotal in her leadership. As a woman and visibl...

The Power of Community and AI in Entrepreneurship 08.09.2025

Imagine navigating the often isolating world of entrepreneurship, only to discover a thriving community waiting to support you. On the Business Legacy Podcast, I sit down with Graeme Barlow, CEO of Iversoft and founder of FounderLink, to reveal how the power of human connections is reshaping the entrepreneurial landscape. We discuss the duality of AI in networking how it both facilitates mass comm...

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