Podcast: Disruptive Successor Show
The Disruptive Successor Show is a podcast for next-generation leaders in family businesses and entrepreneurs who want to disrupt the status quo to grow their business and take it to the next level.
We all know that what got us here isn’t going to get us there.
If you are taking control over your family’s business or trying to get your business to the next level, you will need inspiration, advice and resources to help you create a massive impact.
Listeners of my show include not only the millennial or Gen Z but also the Baby Boomer and Gen Y. My listeners tend to be involved in these industries: business services, construction, design-build-maintain landscape contracting, food manufacturing, property management, real estate, and technology.
And are interested in issues like business coaching, branding, communication, difficult conversations, disruption, employee ownership, exit planning, financial management, leadership, innovation, intergenerational transfer, marketing, multi-generational family businesses, business operations, process documentation, security, selling, storytelling, succession, visioning, wealth management,
My guests are entrepreneurs, family business advisors, multi-generational and Gen 2 family business leaders, heads of university family business programs, consultants, coaches and firms that serve those who are growth businesses.
Clients of my show typically are running businesses with 10 to 200 employees and $1M to $20M in revenues.
Their concerns include: scaling up, exit planning, succession, leadership development, disruption, business planning, finances, growth planning, transferring generational wealth, transferring control, ownership issues, and more.
The benefits listeners receive are introductions to experts and advisors around the issues of growing and exiting a business, whether it’s a family business or entrepreneurial venture. They get a feel for the challenges other business owners and leaders face and how they overcame them. They will hear stories from people and how they came to do their work and why.
My shows feature handpicked guests who engage with me in casual conversations lasting between 30 to 40 minutes. You can expect to be entertained, engaged and may even get takeaways like business tools or ideas for implementation in your business.
I’ve led entrepreneurial adventures in art, clothing, a holistic health lifestyle magazine and trade show, shoe manufacturing. I’ve also led several non-profit organizations. I earned an MBA from the University of Southern California in Entrepreneurship.
I’ve been advising, coaching and consulting family-owned, family-run and entrepreneur-led businesses since 1989. My love for entrepreneurship follows the closure of my family’s sizeable multi-generational clothing manufacturing company after eight decades of operation because there were no successors.
After uncovering the code to scale up a family-run business – a playbook and a disruptive successor – I wrote a book called Disruptive Successor: A Guide To Driving Growth in Your Family Business.
My podcast is my effort to bring interested people into the conversation to benefit disruptive successors.
Jeffrey Condren is a Certified Financial Planner (CFP) and Senior Vice President and Wealth Advisor at Mesirow Wealth Management in Highland Park, Illinois. With over two decades of experience in the financial industry, Jeff specializes in guiding business owners through complex transitions—from business exits to legacy planning. He works primarily with entrepreneurs and multi-generational family businesses, particularly in manufacturing and healthcare sectors throughout the Midwest. His expertise includes tax-efficient wealth strategies, estate structuring, values-based investing, and helping families navigate the challenging conversations around succession planning. Jeff is known for his practical approach to transforming business liquidity into lasting family legacies while addressing the often-overlooked emotional and relational dynamics that can make or break generational wealth transfer.
SHOW SUMMARY
In this episode, Jonathan Goldhill is joined by Jeffrey Condren, a certified financial planner with extensive experience in wealth management and advising multi-generational families. They explore why secrecy often leads to entitlement, the pitfalls of striving for fairness over equality, and the critical need for early and transparent conversations about values, expectations, and the realities of running a family business. They emphasize that successful generational transitions require exposing heirs to responsibility and decision-making early on. The episode also covers the nuances of assigning business roles to family members, handling business valuations realistically, and the importance of external mediation to navigate complex family dynamics.
KEY TAKEAWAYS
- Successful families surface conflict early and structure it, rather than avoiding it
- Fair and equal are not the same thing in family business transitions
- Exposing the next generation to business realities early prevents friction later
- First-generation business owners struggle most with letting go of control
- Business valuations should be updated every 1-2 years, not left for 7+ years
- Depression-era children often feel they never have “enough” money, regardless of actual wealth
- Succession planning takes years, not months – there’s no light switch solution
- The earlier difficult conversations happen, the smoother the transition
QUOTES
- “Successful families do not eliminate conflict. They surface it early, they structure it and use it to clarify values and expectations.”
- “Fair versus equal. It is very different for a lot of people, and it’s a very hard conversation to have, and there’s no right or wrong answer.”
- “Getting a business owner to think about their future self not involving the business… takes time. It’s not a one hour conversation.”
- “Tom Brady, arguably one of the greatest quarterbacks… had a quarterback coach. So when you stop and think about that, he probably doesn’t need one, but there’s still someone pointing out techniques that maybe he’s not seeing.”
- “How long things actually take – there’s not a light switch solution to anything in life. The sooner they’re willing to have the conversation, the smoother it is.”
- “The idea of them not being involved in the business is so hard for them to comprehend that they don’t know where to start and they’d rather ignore it.”
Connect and learn more about Jeffrey Condren.
https://www.linkedin.com/in/condren/
If you enjoyed today’s episode, please subscribe, review, and share with a friend who would benefit from the message. If you’re interested in picking up a copy of Jonathan Goldhill’s book, Disruptive Successor, go to the website at www.DisruptiveSuccessor.com
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