Secrets of Thriving Family Businesses | The Family Biz Show Ep. 99
Release Date: 03/01/2024
How ESOPs Help Family Business Owners Exit Without Losing Their Legacy | The Family Biz Show Ep. 40
The Family Biz Show
What if you could step away from your family business without walking away from everything you've built? What if your exit strategy could protect your people, preserve your culture, and secure your legacy for generations to come? "I've spent decades building this business. How do I leave without losing it?" "I don't want to sell to a buyer who will change everything we've worked for." "Is there a way to retire while keeping our employees and company values intact?" "How do I create an exit plan that benefits both my family and my team?" This conversation gives you the answer. In this episode...
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The #1 Mistake That Could Cost You MILLIONS When Selling Your Business | The Family Biz Show Ep. 133
The Family Biz Show
Ready to sell your business? What if one mistake could cost you millions before negotiations even begin? "Am I really getting the best price?" "What if my business isn't worth what I think?" "Should I accept the first offer?" "How do buyers actually value my company?" "What if I'm not as prepared as I thought?" This conversation gives you the answer. In this episode of The Family Biz Show, Michael Palumbos sits down with Cameron Bishop, Partner and Managing Director at Raincatcher, to uncover the costly mistakes business owners make before selling their companies. From owner dependency and...
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Built To Last: Sustainable Success For Family-Owned Construction Businesses | The Family Biz Show Ep. 132
The Family Biz Show
Growth can look like success from the outside. But inside a family-owned construction business, growth can also create pressure, confusion, and decisions the original business model was never designed to handle. “You built something successful, but why does it feel harder to run?” “Why is every decision still coming back to you?” “How do you pass the business forward without damaging the family?” “What happens when wealth grows faster than communication?” “Are your advisors solving separate problems, or helping you see the whole picture?” This conversation gives you the...
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What Wealthy Parents Must Teach Their Children Early | The Family Biz Show Ep. 131
The Family Biz Show
If you are raising children in a wealthy family, you may wonder how to give them opportunity without taking away their drive. This conversation helps you understand what children need to learn early so wealth becomes a source of responsibility, not entitlement. “I want my kids to appreciate what they have.” “I don’t want comfort to make them soft.” “How do I talk about money without saying too much?” “How do I raise grounded children when life is already easier for them?” “What if I’m accidentally making things too easy?” This conversation gives you the answer. In this...
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The $84 Trillion Opportunity Most Family Businesses Are Missing | The Family Biz Show Ep. 130
The Family Biz Show
You can build a successful business… and still lose the family along the way. Most family business transitions don’t fail because of one catastrophic mistake. They fail because of small conversations that never happened. Because leadership wasn’t prepared. Because expectations were never aligned. Because no one wanted to ask the hard questions. “What happens when I step away?” “What if my kids don’t want the business?” “How do we protect both the company and the relationships?” “Why does every conversation about succession become emotional?” This conversation gives you...
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The Family Business Problems Legacy Can Solve | The Family Biz Show Ep. 129
The Family Biz Show
Most conversations about family business problems focus on what’s broken—conflict between generations, lack of succession clarity, or stalled growth. But what if many family business problems aren’t caused by dysfunction at all? What if they’re caused by something far less obvious—and far more fixable? In this episode of The Family Biz Show, Michael Palumbos sits down with second-generation owner Ed Delia to explore a different lens: many family business problems are not operational failures. They are translation failures. They come from businesses that have built something...
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Common Mistakes During Family Business Estate Planning | The Family Biz Show Ep. 128
The Family Biz Show
What if the biggest threat to your family business legacy isn’t taxes, markets, or competition… but the way your estate plan was designed? This episode challenges one of the most accepted beliefs in family wealth: that family businesses inevitably fail by the third generation. “Why does it feel harder to talk about wealth with my kids than it does to build the business?” “How do I prepare the next generation without losing control?” “What if my estate plan is protecting the money… but hurting the family?” “Why do successful business leaders struggle with family...
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How to Grow a Family Business Without Breaking The Family | The Family Biz Show Ep. 127
The Family Biz Show
What if you could grow your family business without losing the relationships that matter most? Too many family businesses succeed financially while quietly falling apart personally. This episode explores how to avoid that. “I feel like the business is creating distance in my family.” “Growth is bringing more pressure and conflict.” “How do we scale without losing trust?” “I don’t want success to come at the expense of relationships.” “Can family and business actually work together long term?” This conversation gives you the answer. In this episode, Christina Armentano,...
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Family Business Governance That Actually Works Across Three Generations | The Family Biz Show Ep. 126
The Family Biz Show
What if family business governance was less about formal rules—and more about having the right conversations before things break? If you work with family, you know the tension can feel personal fast. “Why does a small disagreement turn into something bigger?” “How do we keep family roles and business roles clear?” “What happens when the next generation wants to grow differently?” “How do we honor the founder without staying stuck?” This conversation gives you the answer. In this episode, you’ll hear from Peter Roberti of Adrian Jules, a third-generation custom clothing...
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What Makes a Family Business Last Across Generations | The Family Biz Show Ep. 125
The Family Biz Show
What actually keeps a family business alive across generations? And how do you protect both the business… and the family relationships that come with it? “Why does succession feel so complicated?” “How do you prepare your kids without creating entitlement?” “What happens when family dynamics start affecting business decisions?” “How do you know if the next generation truly wants this life?” This conversation gives you the answer. In this episode of The Family Biz Show, you’ll hear the powerful story of Domenic Cortese and Cortese Construction Services — a family business...
info_outlineWhat allows some family businesses to survive for generations while others struggle to make it through a leadership transition?
The answer isn't just strategy.
It's trust.
It's communication.
And sometimes, it's learning how to let go.
"How do I know when it's time to step aside?"
"Am I preparing the next generation well enough?"
"How do we keep family relationships healthy while running a business together?"
"What happens when the company outgrows the founders?"
"How do we preserve the legacy without holding back the future?"
This conversation offers powerful answers.
In this episode, Michael Palumbis sits down with Derrik Kassebaum of Cosmos Corporation, a family-owned company that grew from a basement startup into a global organization serving customers in more than 70 countries.
Derrik shares the lessons learned from building a business alongside his father and brothers, navigating family dynamics, growing through adversity, and ultimately helping transition leadership to a new generation.
His story reveals why some family businesses continue thriving while others become trapped by the very success that built them.
About Derrik Kassebaum
Derrik Kassebaum helped grow Cosmos Corporation from a small family operation into an internationally recognized company whose products are sold around the world.
As a second-generation family business leader, former Vice President of Sales and Marketing, author of Live and Let Go, and long-time steward of the family enterprise, Derrik brings decades of firsthand experience in leadership, succession, ownership transition, and family business growth.
The Core Insight
Many family businesses struggle not because they lack talent, vision, or opportunity.
They struggle because leaders hold on too tightly.
The same instincts that help founders build a business can become obstacles when it's time to empower others.
Thriving family businesses learn how to balance stewardship with trust, preserving values while embracing change.
Practical Value
This episode provides real-world insights on succession planning, leadership transition, ownership structures, communication, and creating a family business culture that can survive across generations.
You'll hear practical lessons from a family that successfully navigated growth, tragedy, transition, and legacy planning while remaining focused on purpose and values.
One of the most powerful lessons Derrik shares is simple:
Focus on your "why" more than your "get."
That mindset helped guide leadership decisions, ownership transitions, and the long-term stewardship of the business.
In This Episode, You'll Learn:
- Why letting go is often the key to sustainable family business growth
- How to transition from founder-led leadership to professional management
- Why family members should earn opportunities based on merit
- How purpose-driven leadership strengthens multigenerational businesses
- Why communication is often more important than ownership structures
- How to prepare future generations for responsible ownership
- Why thriving family businesses stay focused on their mission during times of change
- How humility and trust help families navigate difficult transitions
- Why preserving family relationships matters more than winning business arguments
Continue the Conversation
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Explore additional episodes covering succession planning, family governance, leadership transitions, communication, ownership, and building a lasting family business legacy.