Effective exit planning prepares you for more than the transaction by protecting your financial future, personal identity, and sense of purpose after the business is sold.
In this episode of The CEO Project Podcast, host Jim Schleckser speaks with Nate Collins, a former CEO, financial advisor, and Certified Exit Planning Advisor who successfully sold his family business to a private equity-backed media company.
Although the sale exceeded expectations financially, Nate explains why he did not initially consider it a successful exit. He shares the mistakes he made before and after the transaction, from assembling the wrong advisory team to failing to prepare for the emotional realities of no longer owning the company.
You’ll learn how to:
• Assemble experienced legal, financial, tax, and M&A advisors
• Begin planning early enough to identify tax-saving opportunities
• Define success using personal, professional, and financial goals
• Build a financial plan before negotiating the transaction
• Prepare for the loss of identity, purpose, community, and authority that can follow a sale
• Evaluate the risks associated with earn-outs
• Create a meaningful next chapter before leaving the company
• Strengthen the business so it is prepared for a planned or unexpected transition
Nate also explains why strong exit planning should focus on purpose, community, and health in addition to valuation. A profitable transaction alone does not guarantee that the owner will feel secure, fulfilled, or ready for what comes next.
Listen to learn how exit planning can help you build a more valuable company, avoid costly mistakes, and move into your next chapter with greater financial clarity and personal confidence.
Exit Planning Beyond the Sale Price
1:12: Jim Schleckser introduces Nate Collins, a former CEO, financial advisor, and Certified Exit Planning Advisor who now helps business owners prepare for major transitions.
3:48: Nate describes taking control of a struggling multigenerational family business, improving its performance, and eventually selling it for twice the expected value.
5:42: A financially profitable transaction is not always a successful one. Effective exit planning must address the owner’s personal, professional, and financial goals.
8:16: Nate explains why owners need proactive advisors with direct transaction experience, rather than relying on familiar professionals who may lack the necessary expertise.
12:34: Early exit planning gives owners time to evaluate tax strategies, business structure, and other decisions that may significantly affect the proceeds they retain.
Preparing for Life After Ownership
17:36: Nate shares how losing his title, daily responsibilities, community, and sense of purpose led to regret and uncertainty after the sale.
21:08: Personal fulfillment requires more than money. Nate recommends building post-exit exit planning around three priorities: purpose, community, and health.
24:12: Owners should retire to something rather than simply retire from the business by developing a meaningful next chapter that pulls them forward.
27:48: Earn-outs can create significant risk because former owners remain responsible for results while having less control over company decisions and operations.
31:06: Nate explains why exit planning should begin long before a sale, helping owners create stronger companies that can withstand both planned and unexpected transitions.
About Nate Collins
Nate is a former CEO who managed a successful exit to a large, PE-backed media company. He now works with a limited number of business owners, CEOs, and their families to help ensure they are achieving their financial goals. As a Financial Advisor and Certified Exit Planning Advisor, he provides in-depth business exit and financial planning, as well as investment management. Nate helps owners optimize their businesses’ value and transition into the next chapter.