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Exit Strategy Series
Dane Sanders

Exit Strategy Series | Dane Sanders

Key indicators and considerations.

When It Makes Sense for a Business Owner to Walk Away from Selling

Dane Sanders

Selling a business is often the pinnacle of years of hard work, dedication, and personal investment. It's a decision that can significantly impact the owner, employees, and the broader community. However, a completed sale isn’t always a given and there are times when walking away from a potential sale is the wiser choice. This article will explore whether doing so makes sense and will highlight the key indicators that should influence this decision.

Emotional Readiness and Attachment

Emotional Ties to the Business Remain

For many business owners, their enterprise is not just a financial asset, but also a significant part of their identity. The emotional attachment that comes from building and growing their business can make the decision to sell it deeply personal and challenging.

  • Identity and Purpose: Many entrepreneurs find their identity closely tied to their business. The idea of selling can trigger fears about losing purpose in life. If an owner is not emotionally ready to let go, postponing the sale is likely a better option.
  • Fear of Regret: Fearing seller's remorse is common among owners considering a sale. If there's significant concern about regretting the decision, or if an owner frequently second-guesses or feels unsettled by the thought of selling, it’s usually a sign the owner is not fully ready to sell. In such cases, stepping back to reassess emotional readiness can prevent future regret.

Family and Personal Relationships

The decision to sell often involves more than just the owner. Family members involved in the business can have strong opinions about whether to sell. Conflicts within the family can be a strong indicator that it might be better to delay a sale until the conflicts are resolved, as selling amidst family discord can lead to long-term personal and financial repercussions.

  • Family Disagreements: If there are significant disagreements among family members regarding the sale, it might be wise to delay the decision until a consensus is reached.
  • Succession Planning: In family-owned businesses, potential successors within the family might be overlooked. If there is a viable successor, it might make more sense to consider passing the business down rather than selling it.
  • Impact on Personal Relationships: The stress of selling a business can strain personal relationships. If the process is causing undue stress or conflict in the owner’s personal life, it might be a sign that it’s not the right time to sell.
If there are significant disagreements among family members regarding the sale, it might be wise to delay the decision until a consensus is reached.

Financial Considerations: When the Numbers Don’t Align

Undervaluation and Market Dynamics

The financial health of the business and market conditions play a crucial role in determining whether it’s the right time to sell.

  • Market Conditions: Selling during a market downturn can result in lower offers, as buyers may attempt to capitalize on the situation. Waiting for more favorable market conditions could result in better offers that reflect the true value of the business.
  • Understanding True Value: It’s essential for owners to have a clear understanding of their business's worth before selling. Walking away from offers that don’t meet this value ensures the owner isn’t underselling their business.
  • Lowball Offers: If potential buyers are consistently making offers that undervalue the business, there should be no fear of walking away.

Financial Health and Business Stability

The financial health and stability of the business are critical factors in deciding whether to sell or hold onto the business.

  • Growth Trajectory: If the business is experiencing steady growth in revenue and profitability, selling might not be the best decision. Holding onto the business allows the owner to capitalize on future gains, potentially leading to a higher valuation.
  • Debt and Liabilities: Businesses burdened with significant debt or unresolved liabilities might not attract the best offers. Potential buyers might lower their offers to account for these financial issues. It may be wise to address these issues before considering a sale to strengthen the business's market position.
  • Pending Contracts or Deals: If the business is on the brink of securing significant contracts or entering into lucrative partnerships, it might be better to wait. These developments could substantially increase the business’s value, leading to more favorable offers.

Strategic Timing: When Patience Pays Off

Growth Potential and Market Opportunities

A business with untapped growth potential presents a compelling reason to hold off on selling.

  • Expansion Opportunities: If there are clear opportunities for expansion into new markets, products, or services, holding onto the business could lead to much higher returns. Selling before these opportunities are realized could mean missing out on substantial future gains.
  • Innovative Initiatives: If the business is on the verge of launching a new product or service that could transform its market position, it might be better to wait. The success of these initiatives could significantly increase the company’s valuation.
  • Industry Trends: If the industry is poised for growth or technological advancements are expected to benefit the business, holding onto it until these trends materialize could result in a more lucrative sale.

Timing and Market Cycles

The timing of a sale is crucial. Selling at the wrong time can lead to significant financial loss, while walking away allows the owner to wait for a more opportune moment.

  • Economic Cycles: Economic cycles have a significant impact on the timing of a sale. During economic downturns, buyers might be scarce or offer less favorable terms. Conversely, during economic booms, demand for businesses might be higher, leading to better offers. Understanding where the economy is in its cycle can help owners decide whether to sell or wait.
  • Competitive Landscape: If the competitive landscape is about to change due to new entrants, technological disruption, or shifts in consumer behavior, it might be better to hold onto the business. Navigating these changes could strengthen the business’s market position, making it more valuable in the future.
  • Mergers and Acquisitions Climate: The broader mergers and acquisitions (M&A) environment also affects the timing of a sale. If M&A activity is high, there may be more buyers and better offers available. If activity is low, it might be prudent to wait until the climate improves.

Buyer Compatibility: Aligning Visions and Values

Finding the Right Buyer

A crucial factor in deciding whether to sell is finding a buyer whose vision aligns with the owner’s values and goals for the business.

  • Preserving the Legacy: Many business owners are concerned with preserving the legacy and culture they’ve built. If a potential buyer’s vision doesn’t align with this legacy, walking away might be the better choice. It’s important for owners to consider whether they’re comfortable with the changes the new owner plans to implement.
  • Employee Welfare: Employees are often a business’s most valuable asset. If a potential buyer’s plans include massive layoffs, outsourcing, or other actions that could harm employees, it might be worth reconsidering the sale. Walking away from a deal that negatively impacts employees can preserve morale and the business’s reputation.
  • Customer Relationships: If the buyer’s vision includes changes that could alienate key customers, it might be better to walk away and wait for a buyer who values these relationships.

Assessing the Buyer’s Financial Stability and Intentions

The financial stability and long-term intentions of the buyer are critical considerations in deciding whether to proceed with a sale.

  • Due Diligence on the Buyer: Conducting thorough due diligence on potential buyers is essential. This includes understanding their financial stability, track record with previous acquisitions, and long-term intentions for the business. If the buyer appears financially unstable or has a history of mismanaging acquired businesses, walking away is likely the best option.
  • Buyer’s Intentions: Understanding the buyer’s intentions is crucial. Some buyers might be interested in acquiring the business only to strip it of its assets or eliminate a competitor. If the buyer’s intentions are not aligned with the long-term success of the business, it’s wise to reconsider the sale.

Legal and Operational Readiness

Addressing Legal Issues Before Selling

Before selling, it’s essential to ensure that the business is free of any significant legal issues. Unresolved legal matters can complicate the sale process and reduce the business's value.

  • Pending Litigation: If the business is involved in ongoing litigation, it might be better to resolve these matters before selling. Potential buyers are likely to be wary of inheriting legal problems, and ongoing litigation could significantly reduce the sale price or lead to unfavorable terms.
  • Regulatory Compliance: Ensuring that the business is fully compliant with all relevant regulations is essential. Any issues related to regulatory compliance can scare off potential buyers or lead to reduced offers. It may be better to address these issues before proceeding with a sale.
  • Intellectual Property Issues: If the business’s value is tied to intellectual property (IP), it’s important to ensure that all IP issues are resolved and that the ownership of patents, trademarks, and copyrights is clear. Unresolved IP issues can complicate the sale and reduce the business’s value.

Operational Stability and Transition Planning

The operational stability of the business and its readiness for transition are crucial factors in deciding whether to sell or hold off.

  • Management Structure: A strong, stable management structure is crucial for a smooth transition. If the current management team isn’t capable of running the business without the owner, it might be better to delay the sale until a more robust team is in place.
  • Operational Efficiency: Ensuring that the business is operating efficiently before selling is important. Any operational inefficiencies or unresolved issues can reduce the business’s value and complicate the sale. Walking away to address these issues can lead to a higher sale price and smoother transition.
  • Transition Planning: A well-thought-out transition plan is essential for the long-term success of the business post-sale. If the transition plan isn’t fully developed or if there are significant uncertainties about how the business will be managed post-sale, it might be wise to delay the sale.

Conclusion: Making the Right Decision

Deciding whether to sell a business is one of the most significant decisions a business owner will make. Walking away from a potential sale can be just as crucial as deciding to sell. The decision should be based on careful consideration of emotional readiness, financial health, market conditions, buyer compatibility, and legal and operational stability.

By recognizing the indicators outlined in this guide—whether they relate to undervaluation, unresolved legal issues, emotional attachment, or misalignment with the buyer’s vision—business owners can protect their legacy, financial future, and personal well-being. Ultimately, it’s not just about making a deal; it’s about making the right deal at the right time, for the right reasons. Walking away, when done for the right reasons, is not a failure; it’s a strategic decision that can lead to better opportunities in the future.

In our next and final article in this series, I will wrap up in conclusion our 7-part series: How to Navigate the Path for Successfully Selling Your Business.

Opening Background and Pull Quote Image Source: DNY59 / iStock / Getty Images Plus via Getty Images.

Dane Sanders is Managing Director with Madison Street Capital, LLC in Chicago. Dane is a sell-side investment banker who helps middle-market and family-owned business owners hit the Trifecta that every owner who wants to sell their business seeks: sell to the right buyer at the right time and at the right price…theirs!