Legacy Planner For Serial Entrepreneurs | Strategic Advisor

Business Legacy

Business EN ↓ 267 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.

Author

Legacy Planner For Serial Entrepreneurs | Strategic Advisor

Category

Business

Podcast website

sites.libsyn.com

Latest episode

Jul 6, 2026

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Episodes

Where Small Businesses Should Actually Start With AI 06.07.2026

In this episode, Paul Dio sits down with Jonathan Feldman, founder of NextCoreFlow, an automation and AI integration consultancy for small and medium-sized businesses. Jonathan is not a theorist. He's built and exited two businesses of his own — a college advertising magazine he ran across twenty markets and a planner business he grew past thirty million dollars a year on Amazon — before launching...

Turning Data Into Direction for Schools 29.06.2026

In Episode, Paul Dio sits down with Dr. Nicole Aliotto, founder and CEO of Alla Breve Consulting, for a conversation about what good education actually looks like — and why the easiest metrics to measure are rarely the ones that matter most. With nearly three decades of experience spanning higher education, K-12, and the private sector at IBM, Nicole has spent her career helping schools turn data...

Designing the 15 accounting practice to serve your life and make an impact 22.06.2026

Erica Goode spent her early career on the traditional accounting track — Big Four, Fortune 50 finance, the late nights and missed dinners that come standard with the path. Then she looked up at the senior leaders above her and realized she didn't want to be any of them when she grew up. That single honest moment set off a decade-long pivot that took her out of corporate, into full-time motherhood,...

Why Your Business Might Not Need More AI It Might Just Need Better Thinking 15.06.2026

Most business owners hear "AI" and immediately think: we need that. Myles Harrison thinks the opposite — and he built a company around it. Myles is the founder of  Praktikai, a boutique data and AI consulting firm whose name literally means practicality. A veteran of Big Five firms like Accenture and PwC, he now helps business owners cut through the noise and ask the real question: is technology a...

The LinkedIn Blind Spot Costing Executives Their Next Job 08.06.2026

When Carol Kaemmerer's 20-year consulting career was abruptly ended by a corporate restructuring, she didn't see it as an ending — she saw it as a kaleidoscope being shaken. The pieces of her experience, expertise, and skills were still all there; they just needed to form a new pattern. In this episode, Carol shares how she rebuilt her career by helping other senior leaders do the same. Her work s...

Building Confidence, Leadership, and Legacy Through Dance 01.06.2026

In this episode of the Business Legacy Podcast, Paul Dio sits down with Katherine Horrigan, owner and CEO of Dance Academy of Virginia, to discuss how dance became the foundation for leadership, confidence, discipline, and personal growth. Katherine shares her journey from professional ballet and contemporary dancer to entrepreneur, explaining how injuries led her to transition out of performing a...

How 180 Water Is Modernizing the Water Well Industry Through Franchising 25.05.2026

In this episode of the Business Legacy Podcast, Paul Dio sits down with Jack Clark, founder of 180 Water, to discuss how he transformed a traditional water well service company into a rapidly growing franchise model focused on clean, reliable drinking water across rural America. Jack shares his journey from growing up on a Montana ranch to building a scalable business in one of the most overlooked...

How Siloed Departments Quietly Kill Profit 18.05.2026

Most companies don't lose money because of bad ideas. They lose it in the gaps — the quiet space between marketing, sales, and operations where reports never get compared and insights never get shared. In this episode, Paul Dio sits down with Anam Jawad, founder of TCSC (The C-Suite Consultant), to talk about what she calls "the missing dollar" — the revenue and ideas that disappear when departmen...

The Grandparent Advantage: Building Legacy Through One-on-One Connection 11.05.2026

Legacy is often misunderstood as something financial, distant, or reserved for later in life. In this episode, Perry Solomon reframes legacy into something far more immediate—and far more impactful. Perry, founder of Solomon Growth Advisors and author of Grandpa Day, shares how a simple practice—spending intentional, one-on-one time with each grandchild—became a 20-year system for mentorship, conn...

Build the Solution the Market Is Missing 04.05.2026

Most businesses don't start with a perfect idea they start with a problem that can't be ignored. In this episode, Santiago Galvez, founder of Pet Cultures, shares how a personal challenge saving his dog after a severe health issue turned into a fast-growing international brand. After trying dozens of products that didn't work, Santiago realized something deeper: the market was filled with solution...

Why Avoiding Conflict Is Costing You More Than You Think 27.04.2026

Most people don't lack good intentions they lack the tools to handle conflict. In this episode, Kimberly Best, founder of Best Conflict Solutions, shares a powerful journey from trauma nurse to conflict resolution expert—revealing how life's most intense moments shaped her understanding of human behavior, communication, and legacy. Through personal experiences, including witnessing end-of-life ref...

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-...

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