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Lani Dickinson, Founder of Stealth and host of the Freedom To Exit Podcast, sharing expert business exit strategies and recurring revenue insights.

Avoiding Deal Breakers: Make Your Business Sale-Ready

March 11, 20253 min read

The Hidden Landmines That Can Kill Your Exit

You’ve built a profitable business. Sales are strong. Revenue is climbing. So your company must be sellable, right?

Not necessarily.

The biggest myth in exit strategy is believing profitability equals sellability. In reality, 30–50% of businesses that don’t sell fall apart in due diligence—not during negotiations. The killer? Surprises buyers weren’t expecting.

And those surprises? They're usually your blind spots.

Today, we’re unpacking the hidden risks that can tank your sale at the finish line—and what you can do years in advance to avoid them. Because due diligence is not the time to realize your house isn’t in order.


1. Financial Inconsistencies: The #1 Deal Killer

Buyers will scrutinize your numbers. And they don’t just want to see profitability. They want clean, consistent, trustworthy books.

Revenue that's overstated. Expenses that don’t add up. Mixing personal and business finances. These red flags break deals instantly. 60% of failed exits are due to surprise liabilities or inconsistent financials.

What to do:

  • Stop aggressive accounting practices now.

  • Eliminate personal expenses from your books.

  • Work with a CPA or financial advisor to prepare 2–3 years of audit-ready financials.


2. Operational Weaknesses and Owner Dependency

If your business needs you to run, it’s not a business—it’s a job.

Buyers don’t want to buy your schedule. They want a company that can operate without the founder.

Key-person dependency (whether it’s you or another leader) drops valuation or kills the deal. One plumbing company saw a $5M deal collapse when the buyer found out 60% of its revenue came from a single client.

What to do:

  • Build systems and SOPs for every major function.

  • Delegate key responsibilities and document processes.

  • Diversify revenue streams and customer base.


3. Compliance Issues and Legal Landmines

Even profitable, well-run companies can have hidden legal baggage. Regulatory violations, licensing issues, tax liabilities, or undisclosed debt can come back to haunt you—and your buyer.

One healthcare deal collapsed into months of delays after past compliance issues surfaced. The solution? Buying the assets instead of the company—costing six months of reimbursement.

What to do:

  • Run a pre-sale audit with your legal team.

  • Resolve outstanding disputes, lawsuits, or tax issues.

  • Make sure all required licenses and registrations are up to date.


4. Intellectual Property & Real Estate Red Flags

Missing trademarks. Unclear ownership of proprietary processes. Software that isn’t really yours. These issues are massive deal breakers.

Same goes for environmental issues or real estate liabilities. A business built on land with oil drilling rights and underground tanks? That deal got delayed for months due to environmental inspections and title problems.

What to do:

  • Register and protect all your IP.

  • Review software licenses and code ownership.

  • If your business owns real estate, clear the title, environmental issues, and old bank liens well in advance.


5. Concentration Risk (Revenue or Suppliers)

If one client makes up more than 30% of your revenue—or one supplier makes up most of your inventory—your business is high-risk.

Buyers fear that one change could collapse the company post-sale.

What to do:

  • Diversify clients and suppliers.

  • Secure long-term contracts with major accounts.

  • Document your retention and growth strategy.


Fast-Tracking a Sale-Ready Business

The worst time to fix these issues is when a buyer is already in the room. Every surprise reduces your leverage. Every delay kills trust.

Instead, act now:

  • Clean up your financials.

  • Reduce dependencies.

  • Fix compliance gaps.

  • Secure your IP and legal standing.

  • Assess and eliminate concentration risks.

Want to know where you stand? Take the Changes Assessment linked below to audit your own business before buyers do.

Let’s get you ready—for top dollar and total freedom.


Free Resources to Go Further

📌 7 Ways AI Can Boost Your Sales and Save You Time - Download this free guide:
👉 https://ai.activatetoascend.com/get-7ways-ai

📌 3 Ways Your Business Can Use AI TODAY to Stop Leaking Money – Save your seat for the free live webinar:
👉 https://webinar.activatetoascend.com/webinar-register-general

📌 Changes Assessment – Discover where your business is leaking time, money, and momentum:
👉 https://stealthfreedomtoexit.com/changes

Lani Dickinson is a former Fortune 175 CEO turned business strategist and founder of Freedom To Exit. With decades of executive leadership experience, Lani helps self-led entrepreneurs transform their companies into scalable, sellable assets—so they can achieve true time, location, and financial freedom. As the host of the Freedom To Exit podcast, she delivers straight-talking insights, powerful frameworks, and actionable strategies for business owners ready to exit for more.

Lani Dickinson

Lani Dickinson is a former Fortune 175 CEO turned business strategist and founder of Freedom To Exit. With decades of executive leadership experience, Lani helps self-led entrepreneurs transform their companies into scalable, sellable assets—so they can achieve true time, location, and financial freedom. As the host of the Freedom To Exit podcast, she delivers straight-talking insights, powerful frameworks, and actionable strategies for business owners ready to exit for more.

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