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Michael Shea

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The Strategic Buyer Advantage: Why Vacation Rental Management Companies Sometimes Sell for More Than They’re “Worth”

July 29, 2026 by Michael Shea PA

  Why Some Buyers Pay Premium Multiples While Others Won’t One of the most common questions I hear from vacation rental management company owners is: “Why did that company sell for such a high multiple when mine is similar?” The answer often has less to do with the business itself and more to do with […]

Filed Under: businessbroker, Buy a Business, clearwaterbusinessbroker, michaelshea, propertymanagement, Uncategorized, vacation rental management, vacationrental Tagged With: Short Term Rental, Vacation Rental Management

The 350-Door Tipping Point: Why Vacation Rental Companies Become More Valuable at Scale

July 29, 2026 by Michael Shea PA

Discover why the 350-door tipping point can dramatically increase vacation rental management company valuations. Learn how reducing key man risk, building management teams, and creating scalable systems attract premium buyers and higher multiples.

Filed Under: bestbusinessbroker, cepa, certifiedbroker, clearwaterbusinessbroker, exitplan, exitplanning, michaelshea, propertymanagement, Tampa Business Sales, vacation rental management, vacationrental Tagged With: business broker, businessforsale, cepa, exit, Michael Shea, orlando, property management, STR, Transworld, vacation rental, valuation, vrma

A Tale of Two Markets: Navigating High Interest Rates in Florida M&A

July 28, 2026 by Michael Shea PA

If you’ve been reading national headlines or listening to general market commentary over the past year, you might think the small business M&A market has completely stalled. With SBA loan interest rates hovering in double-digit territory and capital costs significantly elevated compared to the sub-5% borrowing era, many business owners assume that selling right now […]

Filed Under: bci, bestbusinessbroker, businessbroker, cepa, certifiedbroker, clearwater, clearwaterbusinessbroker, exitplan, Medical, michaelshea, privateequity, Seller Finance, sellerfinancing, Selling A Business, Selling Your Company, Tampa Business Sales, tampabusinessbroker, transworldbusinessadvisors Tagged With: cepa, clearwater, ebitda, Michael Shea, middle, tampa, Tampa Bay, Transworld

The “Silver Tsunami” Myth: Where Did All the Small Business Listings Go?

July 28, 2026 by Michael Shea PA

For years, conventional wisdom suggested that children of entrepreneurs would pursue corporate careers while their parents eventually sold the family business.

Filed Under: bci, bestbusinessbroker, businessbroker, cepa, certifiedbroker, clearwaterbusinessbroker, cmap, exitplan, exitplanning, michaelshea, Seller Finance, sellerfinancing, Selling A Business, Selling Your Company, Tampa Business Sales, transworldbusinessadvisors Tagged With: businesses, cepa, retirement, Silver Tsunami, tampa, Tampa Bay, valuations

How Private Equity Looks Beyond EBITDA: The Importance of Free Cash Flow and Financial Consistency

July 24, 2026 by Michael Shea PA

  One of the most common misconceptions among business owners preparing for a sale is that EBITDA alone determines valuation. While EBITDA is an important metric, sophisticated private equity investors and lenders view it as only the starting point in evaluating an acquisition opportunity. EBITDA is often described as a measure of operating profitability, but […]

Filed Under: accounting, ai, bestbusinessbroker, michaelshea, privateequity, Tampa Business Sales, tampabusinessbroker, transworldbusinessadvisors Tagged With: business, Consistency, financial, Free Cash Flow, Michael Shea, pe, private equity, tampa, Transworld, valuation

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