#455: Jim Carlisle | Boardroom Ownership: Protecting Value, Preserving Legacy, and Capital Allocation

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:  

• (00:00) Newsletter launch, three lenses of business valuations overview, reconnecting with Jim Carlisle after shared consulting partnership 

• (04:34) Jim's practice focus on growth, exit planning and ESOP work 

• (08:25) Boardroom leadership versus selling and preparing for unexpected events 

• (13:50) Estate planning versus business continuity planning key differences 

• (18:15) Stress testing organizational structure and identifying critical leadership gaps 

• (25:00) Capital allocation mindset and three valuation lenses framework 

• (34:00) Real world story of engineering firm succession disaster 

• (42:06) Advisory boards versus fiduciary boards for succession readiness 

• (50:52) ESOP transactions and tax advantages for business owners 

• (1:00:28) Advisory fee inflation and serving mid market companies 

• (1:06:32) Deal structure gotchas and representation and warranty insurance 

• (1:13:26) Listening to clients versus telling them what you know

Chapters

• (00:00:00) - Independence by Design
• (00:02:15) - Re reconnecting with Jim Wallis
• (00:04:23) - What Drives You?
• (00:08:57) - How to Help Your Client Plan Their
• (00:16:48) - How to Prevent
• (00:21:36) - Is a fiduciary Board Necessary for Business Owners?
• (00:23:36) - Should I Sell the Family Business?
• (00:29:59) - Are You Ready to Sell Your Company?
• (00:35:22) - Have Investment Bankers Got the Right Stuff For Companies?
• (00:38:49) - The Best Price for a Business Deal
• (00:40:48) - Exploring the Deal Structures
• (00:41:52) - How To Sell Your Business?
• (00:45:53) - ESOPs: Valuation
• (00:49:36) - EOSOPs and Private Equity
• (00:51:39) - ESOP vs. Non-ESOPs
• (00:56:46) - Advisory Fees: The Cost of Doing Business
• (01:01:29) - Bradley: On ESOPs and Qualifying Advisors
• (01:06:34) - SBA