Here's a number that surprises most business owners: roughly 70-80% of businesses listed for sale never sell. They sit on the market, price gets reduced, interest fades, and eventually the owner either pulls the listing or the broker stops actively marketing it.
The natural assumption is that these businesses didn't sell because they were overpriced. That's sometimes true. But more often, the businesses that fail to sell have characteristics that make them fundamentally difficult to transfer—issues that no price reduction can fix.
On the flip side, certain businesses attract multiple offers within weeks. Same industry, similar revenue, but dramatically different outcomes. The difference isn't luck. It's a set of specific characteristics that buyers are looking for—and an absence of characteristics that scare them away.
If you're thinking about selling your business in the next few years, understanding these characteristics now gives you time to address them. If you're thinking about selling soon, this will help you set realistic expectations about what's possible.
The Lease Clause That Kills Deals
Let's start with something most owners never think about: their commercial lease.
For businesses anchored to a specific location—restaurants, retail stores, service shops, medical practices—the lease is part of what the buyer is purchasing. They're not just buying your customer relationships and equipment; they're buying the right to operate in that specific location with that specific foot traffic or visibility.
Which is why a single clause buried in your lease can make your business unsellable: the demolition clause.
Deal Killer: Demolition Clause
A demolition clause gives the landlord the right to terminate your lease—sometimes with as little as 30-90 days notice—if they decide to redevelop the property. You can have a thriving, profitable business with loyal customers and a great reputation. But if the landlord can legally evict you at their discretion, the value of that business to a buyer approaches zero.
Think about it from the buyer's perspective. They're taking out a loan to buy your business. The loan is secured against the business's future cash flows. If the landlord can eliminate those cash flows by demolishing the building, the buyer's investment—and the bank's collateral—evaporates overnight.
Buyers who finance through bank loans (which is most small business buyers) will have their lender review the lease. A demolition clause with inadequate protections will often cause the lender to decline the loan. No loan, no deal.
If you have a demolition clause in your current lease, you have two options before selling: negotiate it out during your next lease renewal, or negotiate terms that provide adequate notice and compensation to make the risk acceptable to buyers and lenders.
The Solopreneur Problem
Some of the most profitable small businesses are also the hardest to sell.
Consider the classic solopreneur or "duopreneur" business: one or two owners, no employees, low overhead, lifestyle-friendly hours. The owner has developed deep expertise and strong customer relationships over years or decades. The business throws off excellent cash flow relative to the work required.
For the current owner, it's perfect. For a buyer, it's a problem.
When the business's value is entirely dependent on the owner's skills, relationships, and daily presence, what exactly is the buyer purchasing? The customer list? Those customers may leave when the owner does. The brand? It's probably the owner's name or reputation. The systems? They exist in the owner's head.
The Core Question
Every buyer asks themselves: "What will this business be worth after the current owner leaves?" For owner-dependent businesses, the honest answer is often "significantly less"—which means the price they're willing to pay reflects that reality.
This doesn't mean solopreneur businesses can't sell. It means they require a different approach. The most successful transitions often involve bringing on an employee 12-18 months before the sale, training them on everything, and having them gradually take over customer relationships and operational knowledge. When sale time comes, the buyer isn't just purchasing assets—they're purchasing a trained operator who already knows the business.
This is more work than simply listing the business for sale. But it's often the difference between a successful exit and a listing that expires without offers.
Why Some Buyers Fail the "Legacy Test"
Not every sale is purely financial. For many business owners—especially founders who built something from nothing—the transaction carries emotional weight that doesn't appear on any spreadsheet.
These sellers care about what happens to their business after they're gone. They want to know the employees who helped build it will be treated well. They want to know the customers who trusted them will continue receiving quality service. They want to know the reputation they spent years building won't be destroyed in months.
This isn't sentimentality. It's a legitimate factor that affects whether deals happen.
When a buyer is introduced to this kind of seller and clearly doesn't share these values—if they talk only about cutting costs, make dismissive comments about current employees, or seem focused purely on extraction rather than continuation—the seller may simply refuse to proceed. The deal dies, regardless of the offer price.
When Legacy Matters Most
The importance of "legacy fit" typically correlates inversely with how urgently the seller needs to exit. An owner who's healthy, financially stable, and happy to keep running the business another few years has enormous leverage to be selective. An owner facing health issues, burnout, or financial pressure has less room to be choosy. Know which category you're in before you start the process.
From the buyer's perspective, this means that being well-funded isn't enough. The ideal buyer—from the seller's view—is someone who is fully funded, has relevant industry experience, speaks the same business language, and can demonstrate a high likelihood of success after the transition. They need to show they understand what makes the business valuable and are committed to preserving it.
If you're selling a business you've poured your life into, it's reasonable to want a buyer who respects that. Just be realistic about how much that preference might cost you in terms of time on market or final price.
The Reason for Selling Matters More Than You Think
Every buyer asks the same question: "Why are you selling?"
Your answer matters more than you might expect. It's not just small talk—it's the buyer trying to assess whether there's something wrong with the business that you're not telling them.
Legitimate, low-risk reasons for selling include retirement, relocation, a desire to pursue other opportunities, or simply being ready for a change after many years. These reasons make sense to buyers because they're about the seller's life circumstances, not problems with the business itself.
Desperate reasons raise red flags. If the seller is clearly burned out, overwhelmed, or financially stressed, buyers wonder: is this business actually a burden? Will it become my burden? Are there problems I'm not seeing that caused this desperation?
The Best Position to Sell From
The strongest negotiating position is one where you genuinely don't need to sell. If you're happy to continue operating the business and are only selling if the right opportunity comes along, you can walk away from lowball offers, take your time finding the right buyer, and negotiate from strength rather than necessity.
Desperation is visible. It shows up in how quickly you respond to low offers, how much you're willing to concede in negotiations, how rushed you seem to close. Experienced buyers recognize it and use it to their advantage at the negotiating table.
The solution is preparation. Getting everything in order well before you intend to sell—clean books, documented systems, a business that runs without your constant intervention—gives you options. You can afford to be patient because the business isn't deteriorating while you wait for the right buyer. This preparation doesn't just increase what the business is worth; it increases what you'll actually receive because you're negotiating from a position of strength.
Other Characteristics That Drive (or Destroy) Value
Beyond the major factors above, several other characteristics consistently affect how sellable a business is:
Customer Concentration
If one or two customers represent more than 20-25% of your revenue, buyers see risk. What happens if that customer leaves after the transition? The business's income—and the buyer's loan repayment ability—takes a major hit. Diversified customer bases command higher multiples because they represent lower risk.
Clean Financial Records
Buyers and their lenders will scrutinize your financials during due diligence. If your books are messy, inconsistent, or require significant "trust me" explanations, you're creating doubt. Clean, professionally prepared financials with clear documentation of add-backs and adjustments make due diligence smooth and give buyers confidence in what they're purchasing.
Transferable Systems
Can someone other than you operate this business successfully? That's the question buyers are really asking. Documented processes, trained employees, established vendor relationships, and systems that don't require you specifically to function—these are what make a business transferable. The easier it is for a new owner to step in and operate, the more valuable the business.
Recurring Revenue
Businesses with subscription models, service contracts, or repeat customers on predictable schedules are worth more than businesses where every month starts from zero. Recurring revenue provides visibility into future cash flows, which reduces buyer risk and increases what they're willing to pay.
Equipment and Asset Condition
Outdated equipment that needs imminent replacement is a hidden liability. Buyers factor capital expenditure needs into their valuation. A business with well-maintained, modern equipment is worth more than one where the buyer will need to invest significant capital immediately after purchase.
Employee Stability
High turnover suggests problems. Key employees who might leave after a sale create transition risk. A stable, trained workforce that will remain through the ownership change adds significant value. Conversely, if there are key employees the business depends on, buyers will want to understand what's keeping them there—and what happens if they leave.
The Question to Ask Yourself
If you're considering selling your business—whether soon or in several years—the question isn't just "what is my business worth?" It's "is my business actually sellable?"
Worth and sellability aren't the same thing. You can have a profitable business that generates good cash flow but is essentially unsellable because of owner dependency, lease issues, customer concentration, or other factors that make buyers walk away.
The good news: most of these issues are fixable given enough time. Bringing on employees to reduce owner dependency, renegotiating lease terms, diversifying your customer base, documenting your systems—these are all things you can do if you know about them far enough in advance.
The first step is understanding where you stand.
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