If your goal is to run your company from the boardroom, the real work isn’t just stepping out of day-to-day operations. It’s making sure the business—and your wealth—are protected no matter what happens. In this conversation with attorney and deal advisor Jim Carlisle. Jim has guided hundreds of owners through sales, ESOPs, continuity crises, and legacy planning—and he’s seen what works, what destroys value, and what keeps owners up at night. We unpack how to think like a capital allocator while protecting your operating asset.  

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That means three things: 
1. Estate readiness – ensuring your ownership transfers the way you want without value lost to taxes, infighting, or missed planning windows. 
2. Business operations continuity – having a contingent operational plan so the company runs at full value if you’re suddenly out of the picture. 
3. Market readiness – knowing your valuation through multiple lenses so you can seize a premium-price moment in the market without scrambling. 
 
Jim shares real-world stories of owners who preserved 100% of their company’s value in a crisis—and others who watched it evaporate in weeks. We get into why continuity planning is different from estate planning, how to stress test your org chart, the role of fiduciary or advisory boards, and how to balance legacy, culture, and net proceeds when offers come in. If you want to keep control, protect what you’ve built, and be ready to move when your goals change or the market says “now,” this episode is your blueprint. 
 
Jim Carlisle is a corporate attorney and entrepreneur with 34+ years of experience helping business owners achieve growth, succession, and exit goals. Chair of Dinsmore’s National Growth & Exit Planning and ESOP Transactional Services groups, he guides owners through M&A, ESOPs, estate planning, and business continuity. Drawing on his own ownership experience, he blends legal expertise with practical insight to protect value and preserve legacy. 

 
Chapters:  

Resources: 
Three Valuation Lenses Articles – https://newsletter.ryantansom.com/p/part-1-why-business-valuations-matter-even-if-you-re-not-selling 

Six Components of Deal Structure – https://independence-by-design.castos.com/episodes/427-navigating-deal-structures-the-hidden-factors-that-impact-your-net-proceeds-with-dave-diehl 

The Owner’s Playbook – https://ryantansom.com/ 

ESOP Podcast Mini-Series – https://youtube.com/playlist?list=PLrYrzn97zAwmBULKHjv8DnqOtI42Od6eg&si=8OBisc9zk-8_dfPl 

Ryan Tansom Website https://ryantansom.com/