My Irish father grew up during the Great Depression as one of five boys in a lively, crowded house. With four brothers, every dollar stretched to cover basic needs, and resourcefulness was a necessity, not a choice. Shoes were shared, clothes patched and worn thin, and meals planned with discipline—a vivid lesson in making the most of what little you had.
His advice has echoed throughout my life: “It’s not how much you make, it’s how much you keep.” Today, this simple wisdom holds a powerful message for business owners, especially those thinking about selling. Now my old man bootstrapped from the son of a immigrant subway driver to a successful Physician. To demonstrate how tight my dad was I specifically remember him picking me up from CYO basketball and driving to the local ACME supermarket. We went behind the building in the dark and he boosted me into the dumpster to get the day old bread. (When you are feeding 5 boys yourself in the 70’s things got tight). So Mike what is the point? Well listen close
Many entrepreneurs, despite years of hard work, reach the point of retirement or exit and say, “I can’t afford to sell.” Yet, what they’re really facing is not just financial shortfall, but the consequences of poor personal planning and unclear goals.
Depression-Era Lessons for Closing the Wealth Gap
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Stretching Every Dollar:
My father and his brothers didn’t have much, but they were experts at keeping what they earned. For business owners, this means proactive tax planning, minimizing expenses, and building wealth outside the business early on. Far too often I see folks driving fancy cars they frankly can’t afford or having boats and RV’s that sit idle. All Cash and Deby not being put to work for wealth creation. -
The Power of Prior Planning:
Like my family, those who plan ahead—setting clear savings goals, investing wisely, preparing for taxes and fees—find that business exits aren’t nearly as daunting. Closing the wealth gap starts long before the sale. -
Making Exiting Easier:
When you focus on “what you keep” instead of just “what you make,” you protect yourself from unwelcome surprises. This makes leaving behind the business not only possible, but secure.
My dad’s lessons, formed with five brothers around the kitchen table, are more relevant than ever. The path to real wealth—for families and for entrepreneurs—starts with keeping more, spending thoughtfully, and always planning ahead.
Let’s use those lessons to make business exits seamless and successful. Because, as my father would say, it’s never just about the money you make—it’s about how much you keep.
#PlanningAhead #WealthGap #FinancialWisdom #BusinessExit #IrishFamily #DepressionEraLessons
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.