When Insider Business Deals Go South:

May 1, 2023

Frustrated Business Owner

When Insider Business Deals Go South:

The Challenges of Selling to Employees or Family Members


As a business broker, I’ve seen countless small business owners looking to sell their businesses to employees or family members, and understandably so. These inside buyers often possess a deep understanding of the business, its processes, and its culture. However, the majority of these transactions rarely pan out as expected. In this article, we’ll explore the challenges and pitfalls of selling a business to an employee or family member and why these deals often fail.

Financial Constraints

One of the most significant challenges when selling a business to an employee or family member is the financial aspect. Inside buyers might lack the capital or creditworthiness to secure funding for the purchase. If the owner must finance the deal through seller financing, they could face increased risk and delayed returns.

Conflicting Interests

When selling to an employee or family member, the owner’s interests may not align with those of the buyer. Owners may prioritize a high selling price, while employees or family members could be more focused on job security or retaining control over the company’s direction.

Emotional Baggage

In family-owned businesses, personal relationships and emotions can often cloud decision-making. This emotional baggage can lead to disagreements or resentments during negotiations, potentially derailing the transaction.

Inexperience in Business Transactions

Employees and family members usually lack experience in executing business transactions, which can hinder their ability to navigate the complex process of buying a business. The lack of experience might result in extended negotiations, costly delays, or the inability to complete the transaction.

Undervaluation of the Business

In some cases, inside buyers may undervalue the business due to familiarity or a lack of understanding of its true market value. This undervaluation can result in the owner not receiving a fair price for their business.

Overlooking Legal and Tax Implications

The legal and tax implications of selling a business can be complex. Employees or family members might not fully comprehend these issues, leading to costly mistakes or oversights that could jeopardize the deal.

Impact on Company Culture

A sale to an employee or family member can create tension within the company, as other employees might feel overlooked or uncertain about their future roles. This tension can harm the company’s culture and productivity during the transition period.

Frayed Relationships

Selling a business is a complicated and emotional process. Even if the insider buys the business the stress of the transaction can lead to hurt feelings. Even worse a deal falling through can shatter family and employee relationships, often beyond repair. The risk is high that in the process you will lose an employee or a close family connection.


Selling a business to an employee or family member might seem like an ideal solution for a small business owner. However, the challenges discussed above often lead to difficulties in completing these transactions successfully. It’s essential for business owners to be aware of these issues and consider alternative options, such as selling to a third-party buyer. A seasoned and Professional Business Broker can help you find the right buyer and guide you through the transaction.

For a free and confidential consultation contact Quorum Business Advisors today.