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 […]
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Generational Readiness for Business Exits
Business owners across generations assess their readiness for exiting differently, reflecting personal and strategic priorities. As someone who has guided numerous business transitions, I see the personal leg of exit planning as a critical starting point. The data suggests a generational divide in readiness, with older owners like Baby Boomers showing higher confidence, possibly due […]
Exit Strategy: A Growing Priority for Younger Business Owners
The 2023 National State of Owner Readiness Report highlights a generational divide in business exit planning. Younger business owners—specifically Millennials and Generation X—are significantly more proactive in preparing for their eventual exit compared to Baby Boomers. This shift reflects a broader cultural and financial reality. Baby Boomers often built businesses from scratch, focusing primarily on […]
How Businesses in Tampa Bay and Clearwater Are Organized: Key Insights for Owners and Buyers
Michael Shea works with owners every day to structure smart exits, connect with qualified buyers, and ensure smooth transitions. Whether you’re a Baby Boomer thinking about retirement, a Gen X owner preparing for the next phase, or a Millennial ready to scale and sell, the right plan makes all the difference.
When is the right time to sell my business?
If you’re in Tampa Bay, Clearwater, or St. Petersburg, don’t wait until circumstances force your hand. Start preparing now. Even if you’re not ready to sell today, an experienced broker can help you understand your business’s current market value and build a plan so that when the time is right, you’re positioned for the best outcome.