You've spent decades building your business. Don't let these five mistakes destroy your exit in 90 days.

Selling a business is one of the most significant financial events of your life. For most business owners, it represents decades of hard work, sacrifice, and strategic decisions all culminating in a single transaction.

And yet, despite the stakes, most business owners make critical mistakes that cost them millions or prevent them from selling at all.

Here's the hard truth: 70-80% of businesses that go to market never successfully sell. The difference between those that fail and those that close isn't luck. It's preparation, strategy, and having the right team in place.

We've seen these mistakes play out dozens of times. We've watched business owners list prematurely, hire the wrong advisors, blow confidentiality, accept bad offers, and structure deals that leave money on the table or worse, create legal and financial nightmares that haunt them for years.

You don't have to be one of them.

Here are the five biggest mistakes business owners make when selling and exactly how to avoid them.

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Mistake #1: Going to Market Unprepared

This is the most common and most expensive mistake we see.

Business owners decide they're ready to sell, hire an advisor (or broker), and immediately start marketing the business. No comprehensive valuation. No operational assessment. No strategic planning. Just "let's get it listed and see what happens."

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The problem? Buyers aren't stupid.

When they start due diligence, they'll uncover everything you didn't fix:

• Owner-dependent operations (the business can't run without you)
• Messy or incomplete financials
• Customer concentration (one or two customers represent 40%+ of revenue)
• Weak management team
• Undefined processes and systems
• Declining revenue or inconsistent EBITDA

Once buyers see these issues, one of two things happens:

1. They walk away. You've wasted months, blown confidentiality, and now you're back to square one.
2. They use it as leverage. Your asking price was $10M. Now they're offering $7M—and citing every operational weakness they found.
   
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What Going to Market UnpreparedActually Looks Like

Let's say you own a $12M manufacturing company. You've been running it for 20 years. You're tired. You're ready to retire.

You contact an advisor. They do a quick assessment, tell you the business is worth $10-12M, and suggest listing it immediately. You agree.

Within 60 days, you have three interested buyers. They all submit letters of intent around $9-10M. You're excited this is happening.

Then due diligence starts.

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The buyers discover:

• Your top three customers represent 65% of revenue
• You personally manage all key relationships
• Your CFO is part-time and your financials are a mess
• You don't have documented processes for production or sales
• Two key employees are thinking about leaving

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Suddenly, the offers drop. One buyer walks. The other two come back at$6.5M and $7M—and both want aggressive earnouts tied to you staying involved for three years.

You just lost $3-4 million because you went to market unprepared.

How to Avoid This Mistake: Get YourBusiness Ready BEFORE You List

This is where most advisors stop. They'll tell you "get your business ready" and leave you to figure out what that means.

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We don't do that.

At Trusted BTA, we have a full war chest of strategic partners and transition executive services to get your business to the level it should be before you even think about listing.

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What Transition Executive Services Actually Are

If your business isn't ready to sell, we don't just tell you that and send you on your way. We help you fix it.

Here's how it works:

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Fractional & Interim Executive Leadership:

• Need a stronger CFO to clean up financials? We bring one in.
• Need a COO to document processes and reduce owner dependency? We've got you covered.
• Need someone to build out your management team so buyers see a business that can run without you? That's what we do.
  
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Operational Improvements:

• Increase EBITDA by cutting inefficiencies
• Diversify customer base to reduce concentration risk
• Document systems and processes
• Strengthen key roles and retention plans
• Improve margins and cash flow
  
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Strategic Positioning:

• Identify what buyers in your industry actually value
• Build the narrative that maximizes your multiple
• Create a growth story that justifies premium pricing

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Timeline: Most businesses need 6-18 months of preparation before going to market.Yes, that's longer than you want to wait. But the difference in sale price is staggering.

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We've seen businesses increase their valuation by 20-40% with the right operational improvements made before listing.

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Think about that: A $10M business becomes a $12-14M business. A $5M business becomes a $6-7M business. That's not luck. That's strategy.

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The bottom line: Don't go to market until your business is actually ready. And if you're not sure what "ready" means, talk to someone who can assess it honestly and help you get there.

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Mistake #2: Hiring the Wrong Advisor

We covered this extensively in our previous article on business brokers vs. M&A advisors, but it's worth repeating here because it's that important.

Hiring a business broker when you need an M&A advisor is one of the fastest ways to kill your sale.

Here's the short version:

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Business brokers:

• List your business publicly on marketplaces
• Wait for inbound inquiries
• Facilitate transactions
• Charge lower commissions (8-12%)
• Best for businesses under $1M

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M&A advisors:

• Conduct targeted, confidential outreach
• Manage a strategic process
• Negotiate aggressively on your behalf
• Provide comprehensive guidance from valuation to closing
• Focus on businesses $1M+ where complexity and confidentiality matter

If you're selling a $5M+ business, you need an advisor not a broker.Period.

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How to Avoid This Mistake

Do your homework before you hire anyone:

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Questions to ask:

1. How many transactions have you closed in my industry?
2. What's your average deal size?
3. How do you maintain confidentiality?
4. Who are your strategic partners (CPAs, attorneys, lenders)?
5. Can you provide references from sellers in similar situations?
6. What's your process from engagement to closing?

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If they can't answer these questions clearly and confidently, walk away.

And if their first move is to list your business on BizBuySell with your company name visible, run.

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Mistake #3: Blowing Confidentiality

Confidentiality isn't just important it's everything.

The moment your employees, customers, or competitors know you're selling, your leverage evaporates.

Here's what happens when confidentiality breaks:

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Employees panic:

• Key people start looking for other jobs
• Morale tanks
• Productivity drops
• Your best employees leave before the sale even closes

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Customers get nervous:

• "Is this company stable?"
• "Should we find another supplier?"
• They start taking calls from your competitors
• Contracts don't get renewed

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Competitors circle:

• They know you're vulnerable
• They poach your customers
• They poach your employees
• They spread rumors to damage your reputation

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Buyers smell blood:

• They see the chaos
• They know you're desperate now
• They lowball you or walk away entirely

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Once confidentiality is blown, you can't put the toothpaste back in the tube.

How Confidentiality Gets Blown (And HowWe Prevent It)

There are three common ways confidentiality breaks:

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1. Public Listings with Too Much Detail

This is the broker mistake. They list your business on BizBuySell with:

• Your company name
• Your exact location
• Detailed revenue and profit figures
• Identifying operational details

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Within 48 hours, everyone in your industry knows you're selling.

How we prevent it: We use blind listings with:

• No company names or identifying details
• Vague industry descriptions
• Generic locations ("Northeast Ohio" instead of your city)
• Revenue ranges only—no specifics
• Strict NDAs before any real information is shared

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2. Telling Employees Too Soon

Business owners get excited or nervous and tell their management team before there's a signed deal.

Bad idea.

Even your most loyal employees will start thinking about their future.And if they're worried, they'll start looking for backup plans.

How we prevent it: We help you develop a communication strategy:

• Who needs to know, and when
• How to position the sale to key employees
• Retention agreements and incentives for critical people
• Timing the announcement to minimize disruption

Rule of thumb: Don't tell anyone until you have a signed letter of intent with a qualified buyer. And even then, only tell the people who absolutely need to know for due diligence.

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3. Buyers Who Breach Confidentiality

Here's one most people don't think about: sometimes buyers try to blow confidentiality.

Maybe they're a competitor fishing for information. Maybe they're not serious and just want to see your financials. Maybe they're trying to poach your customers or employees.

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We've seen this happen—and we've handled it.

When a potential buyer violates an NDA or starts making inquiries that compromise your business, we move fast:

• Immediate cease-and-desist communication
• Legal action if necessary (this is where having an attorney on the team matters)
• Damage control with employees and customers
• Removal of the buyer from the process and blacklisting them from future opportunities

Confidentiality isn't optional. It's mandatory. And we protect it aggressively.

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Mistake #4: Accepting the First Offer

You've been on the market for six weeks. A buyer submits a letter of intent at your asking price. You're thrilled. You accept immediately.

Big mistake.

Here's what you just did:

• ✗ You eliminated all negotiating leverage
• ✗ You'll never know if you could have gotten more
• ✗ You gave the buyer control of the process
• ✗ You set yourself up to get squeezed during due diligence

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The first offer is rarely the best offer.
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Why Competitive Tension Matters

The best deals happen when multiple qualified buyers are competing for your business.

When buyers know they're the only one at the table, they have no reason to offer top dollar. But when they know there are other interested parties, suddenly they get aggressive.

This is how you move from $8M offers to $10M+ offers.

This is how you get better terms:

• Less seller financing
• Shorter earnout periods
• Higher upfront cash
• Better purchase price adjustments

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How to Avoid This Mistake

Work with an advisor who knows how to manage a competitive process:

1. Identify multiple qualified     buyers (not just whoever responds to a listing)
2. Engage them simultaneously under NDA
3. Create a structured timeline where all parties submit offers     at the same time
4. Leverage interest to improve terms and pricing
5. Negotiate from strength, not desperation

When buyers know you have options, they respect you more—and they paymore.

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Mistake #5: Ignoring Deal Structure

Here's the scenario that breaks a lot of business owners:

You negotiate a $10M sale price. You're ecstatic. You sign the letter of intent.

Then you sit down with your CPA and attorney to review the actual deal structure.

Suddenly, you realize:

• $2M is held in escrow for 18 months (and you might     never see it)
• $2M is seller financing paid over 5 years at 6% interest
• $2M is an earnout tied to hitting aggressive     revenue targets—after you're no longer running the business
• $4M is upfront cash—but it's structured as an asset     sale, so you're paying ordinary income tax rates on a big chunk instead of     capital gains

You didn't sell for $10M. You sold for $4M now, with maybe $6M more overthe next five years—if everything goes perfectly.

Deal Structure Terms That Can Make orBreak Your Exit

Let's break down the terms that matter:

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Earnouts

An earnout ties part of your purchase price to future performance. It sounds reasonable—but it's often a trap.

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Problems with earnouts:

• You no longer control the     business, but you're responsible for hitting targets
• Buyers can make decisions that tank your earnout and you can't stop them
• Disputes over measurement are common
• Most earnouts don't pay out fully

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If you must accept an earnout:

• Keep it short (1-2 years max)
• Tie it to metrics you can  actually influence
• Define everything clearly in  writing (revenue recognition, cost allocation, etc.)
• Limit the earnout to 10-20% of  total purchase price

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Seller Financing

This is when the seller provides a loan to the buyer for part of the  purchase price.

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Why buyers want it:

• Reduces their upfront cash requirement
• Shows seller confidence in the business
• Can improve their financing terms

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Why you should be cautious:

• You're the bank—and if the business fails, you don't get paid
• Your loan is typically subordinated (everyone else gets paid first)
• You're stuck in a relationship with the buyer for years

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If you must provide seller financing:

• Limit it to 10-20% of purchase price
• Secure it with business assets
• Keep the term short (3-5 years max)
• Charge market interest rates (6-8%)

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Tax Structure: Asset Sale vs. Stock Sale

This is where hundreds of thousands or millions of dollars can disappear.

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Asset Sale:

• Buyer purchases specific assets
• Buyer gets favorable tax treatment (depreciation)
• Seller often pays higher taxes (ordinary income on some assets)
• Most common structure (90%+ of  small business sales)

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Stock Sale:

• Buyer purchases the entity itself
• Seller gets capital gains treatment (lower tax rate)
• Buyer inherits all liabilities (less favorable for them)
• More common in larger deals ($10M+)

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The difference can be massive.

On a $10M sale, the difference between ordinary income and capital gains treatment can be $500K-$1M+ in taxes.

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How to Avoid This Mistake

Don't negotiate deal structure alone. Work with:

• An experienced M&A advisor who understands how to structure deals favor ably
• A CPA who specializes in business sales and understands tax implications
• An attorney who handles M&A     transactions regularly (not your general corporate lawyer)

And negotiate the structure before you sign a letter of intent.Once you're locked in, you've lost leverage.

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The Bottom Line: Don't Make TheseMistakes

Selling your business is complex. High-stakes. And unforgiving of mistakes.

You can't afford to:

• ✗ List unprepared and hope buyers overlook your weaknesses
• ✗ Hire a broker when you need strategic advisors
• ✗ Blow confidentiality and lose employees, customers, and leverage
• ✗ Accept the first offer without creating competitive tension
• ✗ Ignore deal structure and leave millions on the table

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The good news? Every one of these mistakes is avoidable—if you have the right team in place.

At Trusted Business Transaction Advisors, we've built our entire practice around helping business owners avoid these pitfalls:

• We get your business ready before it goes to market (Transition Executive Services)
• We protect confidentiality  aggressively (blind listings, NDAs, strategic outreach)
• We create competitive processes (multiple qualified buyers, not just whoever calls)
• We negotiate deal structure  intelligently (working with CPAs and attorneys to protect your interests)
• We guide you from assessment to closing—and beyond

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You've spent decades building something incredible. Don't let these five mistakes destroy your exit.

Don't Make These Mistakes. Let's BuildYour Game Plan.

If you're thinking about selling your business—or you're already in the process and something doesn't feel right—let's talk.

We'll do a confidential assessment, identify potential issues, and build a game plan to avoid the mistakes that kill deals.

No pressure. No obligation. Just straight answers about where you stand and what you should do next.

📞 Call us: (330) 388-0768
🌐 Visit: www.trustedbta.com
✉️ Email: info@trustedbta.com

Don't leave millions on the table. Let's do this right.