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As a business coach at InspireU Business Coaching, I specialize in working with owners on crafting comprehensive exit plans to transition their company successfully. After devoting years to building a thriving business, it’s crucial to strategically map out the ideal process for capitalizing on your work when the time comes to exit. My individualized exit planning coaching provides a clear roadmap to reach your future liquidity goals through a sale, acquisition, management buyout or other exit event. I partner with you to analyze valuations, tax considerations, leadership continuity, buyer profiles, deal structures and other facets to develop a plan tailored to your personal and financial objectives. With my guidance, you can confidently navigate selling or transitioning your most valuable asset with optimal terms.


What is an exit planning coach?

An exit planning coach is an experienced advisor who provides strategic guidance and counsel to business owners throughout the multi-year process of developing a comprehensive plan to eventually exit or transition their company in a maximally profitable and successful way. A dedicated exit coach helps owners clarify their long-term personal and financial goals, objectively evaluates all strategic options for exiting from an M&A sale to an ESOP to liquidation, handles multifaceted details like valuation analysis and benchmarking, outlines complex tax implications of different paths, identifies the ideal buyer profile that matches the owner’s goals, and ultimately crafts a meticulously detailed, customized multi-year exit plan aligned to the owner’s priorities. With an exit coach’s specialized expertise advising them, owners can craft an optimal endgame strategy.

What does exit planning mean?

Exit planning refers to the detailed, strategic process of proactively creating a long-term plan to transition completely out of a central ownership or leadership role in a business while simultaneously maximizing the overall value realized and achieving the owner’s financial and personal goals. This complex process involves clearly setting objectives for life after exiting, determining the ideal timeline aligned to personal preferences, conducting accurate valuation analysis, thoroughly exploring structuring options from sale to transfer to liquidation, crafting a leadership succession plan for continuity, navigating tax minimization strategies, and meticulously mapping out each incremental step required to ultimately execute the transition from active ownership as smoothly as possible. With robust exit planning, owners can transition their most valuable asset on ideal terms.

Why is it important for business owners to plan for an exit strategy?

Planning as far as 5-10 years in advance for an eventual business exit or leadership transition is crucially important for owners to be able to fully capitalize on the enterprise value they have built over years if not decades of intense effort, and to optimize their financial and personal outcomes when the time comes to depart. A detailed, long-horizon exit strategy helps owners identify and invest in growth opportunities to maximize the company’s valuation and attractiveness to potential buyers. It provides reassurance of leadership continuity and retention success to employees, customers and investors. It allows ample time to execute a gradual transfer on the owner’s preferred timeline aligned with personal goals. And it enables navigating and optimizing complex considerations like tax minimization, deal structure, buyer negotiations, and more. Business owners who wait until retirement to start planning their transition often leave considerable money on the table and risk a far less successful exit.

What are some elements of a successful exit strategy plan?

Some of the key elements to a thoroughly considered and highly effective written exit strategy plan include: clearly defining the owner’s objectives for life after exit and the ideal timeline, determining the optimal buyer profile suited to those goals, crafting a leadership succession plan for continuity, extensive valuation analysis and growth benchmarking, thorough tax minimization tactics, strategically positioning the company over time to attract buyers, evaluating M&A deal structures and options, instituting confidentiality protocols, assessing legal considerations and risks, accounting for owner personal financial needs post-exit, and meticulously mapping out each necessary incremental step from initially announcing intent to transfer to the final close of the deal. A truly comprehensive exit strategy plan will include detailed actions from today until the future end date to execute the multi-year transition smoothly and profitably.

John Jennings was truly a pleasure to work with. He is extremely knowledgeable and thoughtful. He really helped me find harmony in my position and understand the dynamics of my organization. Someone taught me a long time ago that you have 2 ears and 1 mouth. You should always listen more than you talk. John exercises this with his evaluations which allows you to learn more about yourself and how to work more effectively with others. 

John P

GM, Windows & Door Company

I highly recommend John Jennings’ coaching services. It can be hard at times with engagement with our employees, but having an outside source echoing our mission and adding new tools to our toolbox is worth every penny spent on Mr. Jennings services. He was professional, funny and made the team feel at ease, in addition to helping me with engagement with my staff.

Bill K

CEO, Hyndman Area Health Clinic

John Jennings has become a valuable member of our team.  He has helped me transform my company by keeping me focused on both the small goals while keeping an eye on the bigger picture. He’s earned my trust and has reignited my passion for being an independent small business.



Owner, Sunrise Services







14040 Spring Mill Rd; Louisville, KY 40245