Buying a business is one of the most significant investments you will ever make. In a thriving market like Tampa Bay—stretching from the tech hubs of Downtown to the service-based corridors of Brandon and Clearwater—the opportunities are endless, but so are the risks.
Before you sign a Letter of Intent (LOI) or wire a deposit, you must look past the shiny marketing brochure. Here are the 10 essential questions you need to ask to ensure you’re buying a legacy, not a liability.
1. “Why is the owner selling right now?”
This is the most fundamental question. Are they retiring, or are they seeing a regulatory change or a new competitor coming to Tampa that will hurt the business next year?
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What to look for: A consistent, logical reason (like retirement or health) rather than vague answers.
2. “How much of the revenue is tied to the owner personally?”
In many Tampa small businesses, the owner is the “face” of the company. If the customers only do business because of a 20-year personal relationship with the seller, will they stay when you take over?
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What to look for: A business with systems and a management layer that functions without the owner’s constant presence.
3. “What is the ‘True’ Owner Benefit (SDE)?”
Sellers often “add back” expenses to make the profit look higher. You need to verify if these add-backs are legitimate business expenses or if they are essential costs you will have to pay.
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What to look for: Verifiable tax returns and P&Ls that match the seller’s claims.
4. “Is the revenue diversified or concentrated?”
If 50% of the company’s income comes from one contract with a local municipality or a single developer, the business is high-risk.
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What to look for: A broad customer base where no single client accounts for more than 10-15% of total sales.
5. “What is the status of the lease and the landlord?”
In hot markets like South Tampa or St. Pete, real estate is a major factor. You need to know if the lease is assignable and how much the rent might increase upon transfer.
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What to look for: At least 5–10 years of remaining lease term (including options) to satisfy SBA loan requirements.
6. “What does the local competitive landscape look like?”
Tampa is growing fast. Is a national franchise moving in down the street? Is the industry being disrupted by new technology?
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What to look for: A “moat”—something the business does that competitors can’t easily replicate.
7. “Are the employees aware of the sale?”
If the key staff finds out and leaves, you’re buying an empty shell.
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What to look for: A solid confidentiality plan and a plan for how and when the staff will be notified.
8. “What is the condition of the assets and equipment?”
Don’t take “it works great” as an answer. Ask for maintenance logs for vehicles and machinery.
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What to look for: Any “deferred maintenance” that will require you to spend capital immediately after closing.
9. “What are the biggest challenges the business faces today?”
Every business has problems. If a seller says “none,” they aren’t being honest.
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What to look for: Honest answers about labor shortages, rising supply costs in Florida, or marketing struggles. These “problems” are often your best opportunities for growth.
10. “Will the seller provide a training and transition period?”
You don’t want the seller to vanish the day the check clears.
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What to look for: A written agreement for 30–90 days of on-site training and phone support to ensure you learn the ropes and meet key customers.
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. He is also a Florida Licensed Real Estate Broker and Business Brokers of Florida Board Certified Intermediary