Legacy Planner For Serial Entrepreneurs | Strategic Advisor
Business Legacy
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.
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Author
Legacy Planner For Serial Entrepreneurs | Strategic Advisor
Category
Podcast website
Latest episode
Nov 2, 2026
Where to listen?
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Episodes
What Leaving Corporate Life Really Teaches You 02.11.2026 32:59
What happens when a successful corporate career collides with everything else life demands? In this episode of the Business Legacy Podcast, Paul Dio sits down with Zeynep Tolan, a former technology executive who left corporate life and now works as a career counselor at Carnegie Mellon. This conversation is the first in a series exploring what life looks like after corporate careers and what goes...
Great Marketing Is Really Just Great Teaching 26.10.2026 24:40
The best marketers are not always the ones trained in marketing. In this episode of the Business Legacy Podcast, Paul Dio sits down with Aaron Nichols of Exact Solar, host of This Week in Solar and a rising public voice in the clean energy industry. Aaron makes the case that the most effective marketing is really education, and that former teachers may be the most underrated hires a business owner...
What Really Matters When Success Gets Redefined 19.10.2026 50:02
Some of the most successful careers were never planned. In this episode of the Business Legacy Podcast, Paul Dio sits down with Paige Arnof-Fenn, founder and CEO of Mavens & Moguls, a global marketing and branding firm based in Cambridge, Massachusetts. Paige calls herself the accidental entrepreneur. She never wrote a business plan, yet she has run her firm for 25 years. Paige grew up planning to...
Pass Down a Thought Process, Not Just Assets 12.10.2026 24:53
Most business owners already have the advisors. A CPA, an attorney, a financial advisor, an insurance professional. What they rarely have is a team. In this episode of the Business Legacy Podcast, Paul Dio sits down with Dale Montgomery, founder of TRS Family Office, to unpack why siloed advice quietly drains a business owner's bandwidth and how a collaborative advisory model changes the trajector...
Why Your Best Successor might not be anything like you 06.10.2026 30:17
Most personality tests tell you how someone behaves. Very few tell you why. In this episode of the Business Legacy Podcast, Paul Dio sits down with Karl Hebenstreit of Perform and Function, a leadership development consultant and executive coach who uses the Enneagram to help leaders understand the motivation driving their own behavior and the behavior of the people around them. Paul opens with a...
Legacy is Becoming the Person Who Opened the Door 28.09.2026 22:57
The fashion industry has a trust problem. Consumers are no longer sure what their clothes are made of, whether sustainability claims are real, or whether the brands they buy from are telling the truth. In this episode of the Business Legacy Podcast, Paul Dio sits down with Rachel Erickson, CEO and founder of Unmarked Street and The Business of Apparel, to talk about what it takes to bring kindness...
Beyond Numbers Embracing Entrepreneurial Passion 14.09.2026 29:42
Discover the transformative journey from corporate finance to entrepreneurial success with Shanli Liu, founder of Freedom Folio. What if leaving a steady career could lead to a more fulfilling life and business? Shanley's story is a testament to resilience and the power of personal connections, tracing her path from a childhood fundraising event in China to establishing her own CPA practice in Bos...
The Generalist Who Became an Accountant 07.09.2026 32:32
In this episode of Business Legacy Podcast, Paul Dio sits down with Seth Kamens, founder of Kamens CPA, for a conversation that is as refreshingly honest as any the show has produced. Seth didn't set out to build a twenty-five-person accounting firm. He set out to keep the lights on. What he built instead — starting with fifteen clients from his father, a solo practice, and a profile on Thumbtack...
An entertainment attorney on soul reciprocity, identity, and the relationships that deplete you without your permission 31.08.2026 24:27
In this episode of Business Legacy Podcast, Paul Dio sits down with Heather Beverly an entertainment attorney, author, and founder of both the Law Offices of Heather Beverly and Soul Reciprocity — for a conversation that starts in a closet in California and ends somewhere much deeper. Heather has spent twenty-five years protecting and preserving the creative legacies of artists, producers, songwri...
The Unexpected Journey From Law to Legacy 24.08.2026 25:29
In this episode of Business Legacy Podcast, Paul Dio sits down with Daniel Boettcher, founder of The Intrepid Wendell, for one of the most quietly extraordinary conversations the show has produced. Daniel is an attorney, a gemologist, a polyglot, and a jeweler — not because he planned to be, but because an illness redirected a career pointed at the U.S. State Department, and a bitterly cold Februa...
A patent attorney on trust, intellectual property, and the human work technology can't replace 10.08.2026 37:15
In Episode 274 of the Business Legacy Podcast, Paul Dio sits down with Daniel Scola Jr., managing partner of Hoffmann & Baron, for a wide-ranging conversation about intellectual property, the widening trust gap in modern communication, and the human judgment that no AI system will replace anytime soon. Daniel has spent his career at the intersection of law, science, and inventors, and the perspect...
A performance psychologist on confidence, resilience, and the identity work that outlasts the medal 03.08.2026 27:48
Paul sits down with Dr. Jim Taylor — performance psychologist, former U.S. Ski Team competitor, and founder of Prime Mind for a conversation that traces a career built on a single insight. The mind is the final frontier, and almost none of us know how to work it. Jim's origin story is disarmingly honest. He was a good ski racer with a bad head, the kind coaches used to call a head case. One summer...
Clients Don't Want the Newsletter They Want It Sent 20.07.2026 23:16
In this episode, Paul Dio sits down with Jason Bagley, founder of Growth Experts, joining all the way from Cape Town, South Africa. Jason's story is a study in what happens when a marketer stops selling deliverables and starts selling outcomes. He started as a software developer, moved into web design at the exact moment Squarespace and Wix turned it into a race to the bottom, pivoted to a newslet...
Marketing Has No Quick Fix 13.07.2026 22:19
In this episode, Paul Dio sits down with Jennifer Lehman, founder of Forward Thinking, for a conversation that starts on a golf course and ends up somewhere much deeper. A conference champion at Campbell University with a communications degree and a Class A professional status with the PGA of Canada, Jennifer built a consulting career after being told, over and over, that she was overqualified for...
Where Small Businesses Should Actually Start With AI 06.07.2026 27:27
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 24:46
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 31:05
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 16:54
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 19:10
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 31:05
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 14:14
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 14:48
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 20:17
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 26:15
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 17:23
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...
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