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June 13, 2025 23 mins

What if the biggest transaction of your life was the one you were least prepared for? For many business owners, the idea of selling their company sits quietly in the background—until it’s suddenly urgent. But the best exits don’t happen by accident. They’re built intentionally, years in advance.

In this episode, John Napolitano sits down with longtime collaborator and financial advisor Alex Weiss to explore how business owners can prepare for an eventual sale—not just financially, but personally and strategically. With over 15 years of shared experience guiding clients through these transitions, John and Alex unpack the often overlooked details that make or break a business exit.

What You’ll Learn in This Episode:

  • When the clock really starts: Why planning your exit should begin 3–5 years before a sale, and how to use that time to clean up financials, set post-sale goals, and align your team.
  • The power of forecasting and valuation: How to model your life after the sale, determine what you need from your business, and identify the gaps between where you are and where you need to be.
  • Building the right transaction team: From accountants and attorneys to brokers and bankers, discover how to evaluate your current advisors and assemble a team that’s capable of executing a high-stakes transition.

Whether you're thinking about selling a business next year or in the next decade, this conversation will shift how you think about integration, preparation, and what it means to exit on your own terms.

Tune in and discover what it means to approach your business transition with clarity, confidence, and intention.

Key Links

Advisor Representatives at Napier Financial are either 1) Advisor representatives of U.S. Financial Advisors, a registered investment advisor, or 2) Advisor representatives dually registered through U.S. Financial Advisors and Great Valley Advisor Group, registered investment advisors. Financial planning and investment advice is offered through U.S. Financial Advisors and/or Great Valley Advisor Group accordingly.

Podcast produced and distributed by Evergreen Financial Marketing https://www.evergreenfm.com/

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