By Michael Shea, Transworld Business Advisors – Tampa Office
We hear a lot about starting a business. What we don’t hear nearly enough about is how to leave one.
If you’re a business owner, there will come a time when you ask: What’s next? Whether you’re looking to retire, change direction, or cash out, your exit strategy matters. You’ve worked hard to build your business — you deserve a smart exit that meets your goals and gives you a fair return.
At the end of the day, most exit plans boil down to two types of sale:
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Selling to someone you already know
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Listing the business on the open market
Let’s walk through both, but first — how early should you prepare?
Start Preparing Long Before You Sell
Ideally, you start planning your exit the same day you start your business. But most owners don’t. That’s okay — the next best time to start is now.
Here’s what matters most:
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Financial Records: Clean, accurate books are non-negotiable. You’ll need at least two years of clear financials for SBA-backed buyers. This includes tax returns, P&Ls, balance sheets, receipts — everything.
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Leases: If you rent your space, make sure your lease is transferable and long enough to give buyers (and their lenders) confidence.
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Operations: Document what makes your business run. If your business depends heavily on you, you’ll need to show how it can run without you.
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Performance: Keep pushing. Strong revenue and profit numbers right up to the sale boost your valuation. Don’t take your foot off the gas.
Option 1: Selling to a Friendly Buyer
Selling to someone you already know — a family member, employee, partner, or loyal customer — sounds appealing. The transition is smoother. The legacy stays intact. You avoid the hassle of marketing.
But it’s not without risk.
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These buyers often don’t have the cash upfront.
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You’ll likely need to offer seller financing — and if the business stumbles after you leave, that money may never come in.
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You may end up involved longer than you want.
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Deals with family and friends often lack objectivity and can get emotional.
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There’s a saying in our world: “If you’ve got one buyer, they’ve got you.”
Also consider this stat: Only 40% of family businesses make it to the second generation. Just 3% survive to the fourth. And the emotional toll of family drama over control? Not worth it for many sellers.
Sometimes the cleanest break is the best one. That’s where the open market comes in.
Option 2: Selling on the Open Market
Most small business owners eventually go this route — and for good reason. The open market brings more competition and better offers.
Buyers fall into two buckets:
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Individual Buyers
These are people looking to own a business and earn a living. They’re usually entrepreneurial, may have related experience, and value your expertise. They tend to retain your team and keep operations going. -
Strategic or Corporate Buyers
These are companies that want to acquire your business to expand their own. They have deeper pockets, can pay more, and often bring resources that increase your company’s value post-sale.
Strategic buyers are especially interested in businesses earning over $1 million. If that’s you, they may want you to stay on through a transition period. These deals can get complex — and they require serious professional guidance.
Why You Need a Business Broker
No matter which route you take, don’t try to go it alone. Listing your business for sale publicly can damage employee morale, spook customers, and kill vendor relationships.
At Transworld Tampa, we protect your confidentiality, help you accurately value your business, and bring qualified buyers to the table. We don’t just post a listing and hope for the best — we leverage a global network and years of experience to make sure your sale is done right.
If you’re thinking about your next chapter, let’s talk. I’ll help you figure out whether selling is the right move — and if it is, how to make it count.
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.