As a business broker who has worked with hundreds of owners across Tampa Bay and Central Florida, Michael Shea of Transworld has observed firsthand the challenges many entrepreneurs face when it’s time to step away from their businesses. New data from the 2025 State of Owner Readiness: Generational Report highlights the urgency of stepping up planning—especially for Baby Boomers, the generation most likely to be approaching a business exit but least likely to be ready for it.
•Baby Boomers lag far behind their younger peers in updating estate plans, with only 41% having done so in the last two years.
•By contrast, 61% of Gen X and 71% of Millennials have updated their estate plans in that timeframe, revealing a stark generational divide in preparedness.
•While 65% of owners acknowledge they will need to harvest their business value to support life after exit, only 60% have had a formal business valuation recently—a gap that is especially problematic for Baby Boomers.
The Risk of Poor Planning
•Baby Boomers are the only group with a higher percentage needing to harvest value than those who’ve formally valued their business, underscoring a lack of alignment between plans and reality.
•Only 35% of Boomers have had their business formally valued in the last two years, compared to 61% of Gen X and a remarkable 74% of Millennials.
Michael Shea advises every business owner—especially Boomers—to take these crucial steps right now:
•Update estate and financial plans to reflect current needs and market conditions.
•Schedule a formal, professional valuation to understand the true worth of the business—key to supporting a fulfilling post-exit lifestyle.
•Start exit planning early, involving advisors who understand both the financial and personal aspects of transitioning out of ownership.
•Consider succession planning and leadership development to minimize risk and maximize value at exit.
This readiness gap is a warning sign—but it’s also a tremendous opportunity for owners, families, and their advisors. By acting now to close the gap, business owners can ensure a smoother transition and a stronger financial future for themselves and their loved ones.
For trusted guidance on business sales, valuations, and exit strategies, reach out to Michael Shea at Transworld Tampa—he brings two decades of expertise and more than 400 successful transactions to every engagement.
Michael Shea represents the Tampa Florida Transworld office. In business since 2005, he has established a reputation as a trusted business broker across Florida’s key markets- from Tampa to Orlando, Melbourne, and more. Over the past two decades, Michael and his team have closed over $1 Billion in sold business volume and presided over more than 450 transactions. His credentials include the IBBA Certified Business Intermediary®, and most recently, the prestigious Certified Exit Planning Advisor® (CEPA) credential.