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Navigating the Complexities of Business Law in Winnipeg: Insights from TLR Law
Philippe Richer
May 15, 2024
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Selling a business is a monumental decision, often marking the culmination of years, if not decades, of hard work, dedication, and investment. As an entrepreneur, you might think about selling your business several times a year, particularly during periods of high stress or significant challenges. However, the optimal time to consider selling your business is long before you actually decide to sell. At TLR Law in Winnipeg, Manitoba, our mission is to make law accessible for the average Canadian, including entrepreneurs eager to navigate the complexities of selling their business. Here’s a comprehensive guide to help you understand the intricacies of this significant transaction.

Understanding the Right Time to Sell

Selling a business should be a strategic decision made well in advance. It’s a common misconception that the best time to sell is when problems arise. In reality, selling during a crisis often means a lower valuation because potential buyers will see the existing problems. Instead, consider preparing your business for sale from the moment you start it. This forward-thinking approach allows you to establish a solid foundation, ensuring that your business is attractive to potential buyers when the time comes.

The Differences Between Selling to Family Members and Third Parties

When considering selling your business, it's crucial to understand the differences between selling to family members versus third parties. Selling to family members often means a focus on legacy and continuity. You may need to freeze the value of your corporation into preference shares that you hold while issuing new shares to the new generation. This approach allows the next generation to run the business, generate profit, and gradually buy out your preference shares over time.

On the other hand, selling to third parties, such as a rival or an external buyer, usually involves cashing in. This type of sale can be your retirement fund, where you sell the business outright and receive a lump sum payment. The process involves more immediate financial gain but requires thorough preparation to ensure your business is attractive and well-managed.

The Importance of Legal and Financial Preparation

Proper legal and financial preparation is essential when selling your business. As a business owner, you need to ensure that your books are in order, your taxes are paid, and all legal obligations are met. This includes having contracts for your employees, a proper anti-spam policy, and compliance with privacy obligations. These steps make your business more attractive to potential buyers and can command a higher price.

A well-managed business with a clear legal and financial standing is more likely to attract buyers and secure better offers. Regular meetings with your legal and accounting team can help you stay on top of these requirements and address any issues before they become significant problems.

Structuring the Sale for Maximum Benefit

When structuring the sale, your goal is to minimize risk and maximize financial gain. One way to achieve this is by negotiating the terms of the sale, including representations and warranties. These are commitments you make to the buyer about the state of the business. For instance, you may need to provide assurances that all taxes are paid and that the business complies with all relevant laws and regulations.

The negotiation process also involves determining the survival period, which is how long you will be responsible for any issues that arise after the sale. Limiting this period as much as possible can reduce your risk. Additionally, structuring the sale to get as much cash upfront is ideal, as it allows you to move on without the burden of potential future liabilities.

Choosing Between Selling Shares or Assets

Deciding whether to sell the shares of your corporation or just the assets is a critical decision. Selling shares means transferring ownership of the entire corporation, including all its liabilities. This approach is often cleaner and simpler for the seller, as it passes all existing responsibilities to the buyer.

In contrast, selling assets involves selling individual components of the business, such as equipment, contracts, and intellectual property. This method can be more attractive to buyers, as they avoid inheriting any hidden liabilities. However, it also means the seller retains the corporation and may face ongoing responsibilities.

Managing Employee Transitions

Employees are a significant consideration when selling a business. Whether you sell shares or assets, the buyer typically takes on the employees and any associated liabilities. This includes honoring existing employment contracts and addressing any severance obligations. Properly managing this transition is crucial to maintaining business continuity and ensuring a smooth handover.

Key Legal Documents

Several key legal documents are involved in the sale of a business. These include:

  • Letter of Intent: This document outlines the preliminary terms of the sale and serves as a starting point for negotiations. While not legally binding, it helps clarify the intentions of both parties.
  • Business Purchase Agreement: This is the main contract that details the terms of the sale, including purchase price, warranties, representations, and any conditions that need to be met.
  • Non-Competition and Non-Solicitation Agreements: These agreements prevent the seller from competing with the business or soliciting its employees and clients for a specified period after the sale.
  • Employment Agreements: If the seller is to remain with the business for a transition period, this agreement outlines the terms of their continued involvement.

Understanding Tax Implications

Tax implications are a significant consideration when selling your business. In Canada, entrepreneurs can benefit from the lifetime capital gains exemption, which allows you to sell qualifying shares of your business and claim an exemption on the capital gains. This can significantly reduce your tax burden and maximize your financial gain from the sale.

Proper tax planning with your accountant is essential to ensure you meet the requirements for this exemption and to explore other tax-efficient strategies for the sale.


Selling your business is likely the most significant transaction of your life, and having the right team in place is crucial. At TLR Law, we are committed to providing accessible, insightful, and effective legal advice to help you navigate this complex process. With offices in St-Boniface, South Winnipeg, and St-James, we are here to support you every step of the way. Whether you're considering selling your business now or in the future, reach out to us for expert guidance tailored to your unique situation. Visit our website at to learn more and subscribe to our newsletter for ongoing insights and updates.