In this episode, host Adam sits down with Ed Hart, a family business expert, host of the 'From the Heart' podcast, and co-author of 'Boomer Wisdom.' They delve deep into why emotional intelligence is a crucial yet underrated element in family businesses. The conversation covers the significant impact of seeking external help for sustained success across generations, with examples of businesses that flourished due to humility and openness to outside insights. Ed shares stories from his extensive experience working with family businesses, offering valuable advice on conflict resolution, the importance of servant leadership, and preparing for retirement. The episode is a treasure trove of insights for family business leaders navigating legacy and generational dynamics, eager to strengthen love, legacy, and lifestyle within their organizations. If you're a family business leader, this episode is a must-listen. Enjoy the deep, fearless conversation that encapsulates the essence of maintaining a thriving family business.

00:00 Introduction to Emotional Intelligence in Family Business

01:41 Welcoming Ed Hart: A Journey Through Family Business

02:34 The Good, The Bad, and The Ugly of Family Businesses

04:26 The Importance of Emotional and Cultural Intelligence

06:11 The Role of Advisors and External Help

13:00 Generational Dynamics and Succession Planning

24:08 Conflict Resolution and Family First Philosophy

29:53 Navigating Family and Business Dynamics

30:12 Examples of Successful Family Businesses31:26 The Importance of Managing Expectations

32:15 The Pressure of Maintaining a Family Legacy33:41 The Reality of Selling a Family Business

34:09 Transitioning Leadership in Family Businesses

37:39 Preparing for Retirement and Finding New Passions

43:55 Boomer Wisdom: Lessons for the Next Generation

48:45 The Value of Intergenerational Learning

50:12 Conclusion and Final ThoughtsFind Ed HERE

Hart Leadership Group

From the Hart Podcast

Boomer Wisdom

The True Cost of Trump’s Big Beautiful Bill on Family Business

In this episode of Fearless Family Business, Adam critically examines a recent piece of legislation—referred to as Donald Trump's 'One Big, Beautiful Bill'—that entails multi-trillion dollar tax cuts, program cuts, and spending increases. Adam argues that while some may benefit financially in the short term, the bill has dire long-term implications for family businesses and society as a whole. Key points include the exacerbation of the humanitarian crisis through increased immigration enforcement, the enlargement of the federal deficit, and the widening wealth gap. Adam advocates for investment in education, healthcare, and inclusion as essential pathways for sustainable economic prosperity and value creation. The episode underscores the need for family businesses to focus on innovation and long-term legacy rather than short-term gains.

00:00 Introduction: The Big Beautiful Bill

00:19 Why I Oppose the Bill

01:46 Overview of the Legislation

03:51 Impact on Social Programs and Defense Spending

06:44 Humanitarian Crisis and Immigration Enforcement

10:35 Deficit and Fiscal Responsibility

22:06 Wealth Gap and Value Creation

26:38 Conclusion: A Call to Action for Family Businesses

What if everything we believe about family, legacy, and love is just a cultural illusion layered over millions of years of primal instinct?

Tim Ash, executive advisor, bestselling author, and evolutionary psychology expert, forces us to wrestle with this uncomfortable question. As CEO and co-founder of a digital optimization agency, Tim helped create over $1.2 billion in value for companies like Google, Expedia, and Facebook. But his real expertise lies in understanding the primal brain that drives all human behavior.

In this fascinating conversation, Tim reveals how evolutionary psychology impacts everything from family business succession to marketing strategy to relationship dynamics. Discover why traditional family business advice might be fighting against millions of years of human evolution, how to properly initiate employees into your tribe, and why your personal purpose determines your company's success.

This episode pulls back the curtain on the biological forces shaping your business decisions—whether you realize it or not.

0:00 Intro

3:14 From AI Research to $1.2 Billion in Digital Growth

6:37 Why Evolution Only Cares About Reproduction, Not Happiness

10:35 The Surprising Truth About Grandparent Investment Patterns

14:22 Why "We're All Family" May Be Sabotaging Your Business

20:26 The Fractional Executive Solution for Mid-Market Companies

26:03 Brand Voice: The One Thing You Can't Outsource

31:14 The Four Elements of Tribal Initiation in Business

39:56 Primal Dating: The Science Behind Modern Relationship Failure

44:41 Why 50% Divorce Rate Threatens Family Business Planning

51:36 The Minimum Relationship Framework for Business Partners

Resources Mentioned:

📚 "Unleash Your Primal Brain" by Tim Ash

📚 "Primal Dating" by Tim Ash & Dr. Lamour Gottlieb

🌐 Tim's Executive Advisory: https://www.timash.com

🌐 Primal Dating: https://www.primaldating.com

📧 Contact Adam to request a free 90-minute EOS workshop: adam.hill@eosworldwide.com

Follow Adam:

IG: @theadamchill

YouTube: @adamchill

Shownotes:
LinkedIn: https://www.linkedin.com/in/adamchill

Why do family businesses always end up as the punchline in Hollywood?

From “Billy Madison” to “Succession”, from “Tommy Boy” to “The Righteous Gemstones”, family businesses are entertainment gold because of their dysfunction. But behind all that chaos lies a blueprint for what NOT to do—and more importantly, what TO do instead.

Adam Hill breaks down the most iconic family business disasters in movies and TV, revealing the three critical elements that could have saved them all. Drawing from his experience leading a fourth-generation company and analyzing shows like “Arrested Development” and “Schitt's Creek”, he uncovers why 70% of family businesses fail and how to build a drama-free operation that won't end up as Hollywood's next comedy.

This episode is your guide to creating the kind of boring, successful family business that would never make it to the big screen—and why that's exactly what you want.

0:00 Intro

2:15 Why Family Businesses Are Hollywood's Favorite Punching Bag

8:45 Arrested Development: The Anatomy of Denial

12:30 Succession: When Power Trumps Purpose

15:20 Tommy Boy & Billy Madison: The Unpreparedness Problem

18:10 The Righteous Gemstones: Identity vs. Mission

21:45 The Three Elements That Could Save Every Hollywood Family Business

25:20 Building Accountability Through Structure, Not People

30:15 Communication: From Artificial Harmony to Healthy Conflict

35:40 Preparation: Teaching Value Creation Over Preservation

Resources Mentioned:

🌐 Patrick Lencioni's Conflict Continuum: https://www.tablegroup.com/conflict-continuum

🌐 Harvard's Strategic Insights in Three Circles: https://hbr.org/2007/11/strategic-insight-in-three-circles

🌐 EOS Accountability Chart: https://www.eosworldwide.com/accountability-chart-download

📧 Contact Adam to request a free 90-minute EOS workshop: adam.hill@eosworldwide.com

Follow Adam:

IG: @theadamchill

YouTube: @adamchill

LinkedIn: https://www.linkedin.com/in/adamchill

What if the very thing you think is preserving your legacy is actually destroying it?

Drawing from his experience as a fourth-generation leader of a 100-year-old company, Adam Hill reveals why the traditional focus on preservation is creating a "legacy trap" that's dooming families to the three-generation curse.

This isn't just theory. It's hard-won wisdom from someone who watched his own family business nearly collapse under the weight of trying to preserve what was–instead of preparing what could be.

Discover why 70% of family businesses fail to transition to the second generation, how the hero's journey applies to family legacy, and the critical difference between creating mythology versus building a blueprint for the future.

If you're a family business leader worried about succession, this episode will fundamentally shift how you think about preparing the next generation.

0:00 Introduction

6:45 The Legacy Trap That Nearly Destroyed Our Business

9:12 Why 70% of Family Businesses Fail by Generation Two

12:30 Preservation vs. Preparation: The Critical Difference

15:18 The Sacred Cow Problem in Multi-Generational Companies

18:45 Why Value Creation Is the True Foundation of Legacy

21:33 Individual Legacy vs. Collective Legacy

23:20 The Hero's Journey and Family Business Succession

Resources Mentioned:

📚 “The Hero's Journey” by Joseph Campbell: https://a.co/d/64dkfvZ

📧 Contact Adam to request a free 90-minute EOS workshop: adam.hill@eosworldwide.com

Follow Adam:

IG: @theadamchill

YouTube: @adamchill

LinkedIn: https://www.linkedin.com/in/adamchill

What happens when you achieve everything you thought you wanted in your 20s…but feel completely unfulfilled?

Cathy Christen, founder of Elevated You, co-founder of GoBundance Women, and bestselling author of "Life as a Masterpiece," thought she had it all figured out by 25. Multiple six-figure income, broken records, outward success—but inside she was lonely, exhausted, and questioning everything.

Her transformation from workaholic achiever to intentional leader offers a masterclass in building life and business with purpose. Discover how she shifted from "everything in her head" to documented systems that freed up six months of travel time per year, why treating employees like family might be sabotaging your culture, and how to develop people who can be better than you.

0:35 Introduction

2:51 The Catalyst: Achievement Without Fulfillment

7:39 How Cutco Shaped Her Leadership Foundation

15:37 The Great Shift: From Hustle to Systems

29:28 From Operator to True Business Owner

30:31 Developing Women Leaders in Male-Dominated Industries

41:25 Finding Your Tribe: The GoBundance Story

47:01 Raising Kids in Abundance vs. Poverty Mindset

Resources Mentioned:

📚 "Life as a Masterpiece" by Cathy Christen

🌐 GoBundance Women: https://www.gobundancewomen.com

🌐 Cathy's website: https://www.cathychristen.com

🌐 Elevated You: https://elevatedyou.org/

📧 Contact Adam to request a free 90-minute EOS workshop: adam.hill@eosworldwide.com

Follow Adam:

IG: @theadamchill

YouTube: @adamchill

LinkedIn: https://www.linkedin.com/in/adamchill

How do you transform from the family business's biggest skeptic into its most passionate advocate?

Kevin Tsao, Chief Sustainability Officer of Eno Brands, a fashion jewelry manufacturing company, didn't just resist the family business—he rejected it outright. But sometimes our strongest resistance reveals our deepest calling.

In this powerful conversation, Kevin shares his transformation from a state government employee who vehemently opposed joining the family business to a leader who has found his purpose in community building and sustainability.

Discover how he shifted the narrative from "Joyce's son" to a respected leader, why treating employees as "family" might not be the best approach, and how he's preparing for the next generation without repeating the pressures he once faced.

This episode is a masterclass in finding your authentic path within a family legacy and turning resistance into purpose.

0:04 Introduction and Initial Resistance

3:21 The Immigrant Journey

7:39 Overcoming Fear and Finding Logic

11:52 Starting as a Receptionist: Earning Respect

16:18 The Hidden Value of Small Family Businesses

19:22 Redefining "Family" in Family Business

25:05 The Manufacturing Journey from Taiwan to China

28:00 Navigating Succession and Geographic Challenges

31:47 Adapting to Tariffs and Global Changes

36:22 Breaking Through the Leadership Plateau

42:40 From CEO to Chief Sustainability Officer

46:22 Building Legacy for the Next Generation

Resources Mentioned:

📧 Kevin’s email: kevin@enobrands.com

🌐 Kevin’s LinkedIn: https://www.linkedin.com/in/kevin-tsao28/

🌐 Kevin’s Company - Eno Brands: https://www.enobrands.com/

📧 Contact Adam to request a free 90-minute EOS workshop: adam.hill@eosworldwide.com

Follow Adam:

IG: @theadamchill

YouTube: @adamchill

LinkedIn: https://www.linkedin.com/in/adamchill

What happens when a fourth-generation family business leader finds himself drowning in anxiety despite outward success?

Franklin Swann, CEO of the 130-year-old Swann's Furniture and Design, shares his raw journey from overwhelming self-doubt to thriving leadership. He reveals how implementing the Entrepreneurial Operating System (EOS) didn't just save his business during the pandemic—it transformed his entire life.

Discover the powerful truth about emotional health in leadership, why systems matter more than hustle, and how working on yourself is just as important as working on your business. This episode is a masterclass in sustainable leadership and building generational wealth through intentional growth.

0:00 Intro

2:22 The 130-Year Legacy of Swann's Furniture

5:35 Surviving the Great Depression Through Oil Booms

8:02 High Service, High Quality Business Model

13:01 How EOS Transformed Operations

16:22 Surviving the Pandemic Through Systems

20:45 From Managing to Leading

23:57 Starting in the Family Business at 12

28:59 The Dark Season of Leadership

32:38 Discovering Emotional Health

36:42 Daily Practices for Self-Relationship

39:54 The World Needs Men Podcast

43:43 Building Legacy for the Next Generation

Resources Mentioned:

📚 "Outlive" by Peter Attia

🎙️ The World Needs Men podcast: https://theworldneedsmen.com/

🌐 Swann's Furniture and Design: https://www.swanns.com/

Follow Adam:

IG: @theadamchill

YouTube: @adamchill
LinkedIn: https://www.linkedin.com/in/adamchill

📧 Contact Adam to request a free 90-minute EOS workshop: ⁠adam.hill@eosworldwide.com⁠