Selling a Business Is the Biggest Financial Transaction of Your Life.
Most People Only Get One Shot.
The buyers and investors on the other side of your deal have done this before. Their lawyers have too. Without experienced business counsel in your corner, the gap shows up in ways that are hard to see until it's too late:
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The deal is structured as an asset sale when a share purchase or hybrid would have saved you hundreds of thousands in tax.
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The Lifetime Capital Gains Exemption is lost because nobody flagged the two-year planning requirement before you signed the LOI or because the deal isn't structured properly.
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Closing adjustments and buyer-friendly incentives quietly erode what you actually get to take home from the deal.
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Representations and warranties leave you personally exposed to claims long after you've moved on.
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A transaction consumes 3 to 12 months of your life (depending on the due diligence and clean-up processes). Without experienced counsel managing the process, it takes longer, costs more, and creates more stress than it should.
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It is difficult to find experienced legal counsel outside of big law. Big law is expensive.
The difference between bad outcomes and good ones is who you had in your corner. Outsiders Law does business buying and selling transactions. And we do them a lot.
What Outsiders Does for Sellers
You need more than a lawyer who can draft a purchase agreement. You need a team that understands what your business is worth, how to structure the deal to maximize what you keep, and how to protect you from risks that only show up after closing.
Here is what we do for every seller we represent:
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Structure the deal for maximum after-tax proceeds. Share purchase, asset sale, or hybrid; we identify the structure that puts the most money in your pocket after tax, including LCGE planning.
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Negotiate from the LOI forward. The most important terms are set at the letter of intent stage. We are at the table from the beginning, not just at the end.
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Manage due diligence. We run the due diligence process efficiently, resolve issues before they become deal-killers, and make sure nothing surprises you at closing.
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Draft and negotiate the definitive agreement. We protect you on representations and warranties, indemnification, closing adjustments, and every other term that affects what you actually walk away with.
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Get you to closing. We coordinate every moving part, including lawyers, accountants, lenders, brokers, and work to ensure the deal closes on time (if possible) and on terms.
The Business Sale Process:
From Decision to LOI to Closing
1. Initial Consultation - We start by understanding your goals, your business, and your timeline. No obligation, clear explanations of what to expect; just a straight conversation about what you are trying to achieve.
2. Exit Planning & Tax - For sellers, early tax planning is critical. We identify opportunities to maximize your after-tax proceeds, including LCGE planning, before a deal is ever on the table.
3. Letter of Intent & Deal Structuring - We help negotiate and finalize the LOI, structure the transaction for maximum tax efficiency, and set the commercial terms that will govern the definitive agreement.
4. Due Diligence - We manage the due diligence process thoroughly and efficiently, identifying risks, resolving issues early, and making sure nothing surprises you at closing.
5. Definitive Agreement & Closing - We draft, negotiate, and finalize the definitive agreement and all closing documents, coordinating every moving part to get your deal across the finish line.
Why Sellers Choose Outsiders Law?
Big-Law Trained Counsel Without the Big Law Overhead
Many lawyers will tell you they can handle your deal. Most lack the experience to do it well. Few of them have sat on your side of the table.
Sebastian Elawny brings nearly two decades of big law-trained tax and transaction experience, including as head of the tax group at a large multinational law firm and founding partner of the Business Law group at a Big 4 accounting firm. As a business owner who has been through the M&A process personally, he knows what it feels like to be the person signing, not just the person drafting.
Chace Stokowski is a lawyer and a CPA who came to law from a career in finance and audit. That background means he analyses your deal from both a legal and financial perspective simultaneously; identifying issues and opportunities that most lawyers simply would not see.
Sam Khajeei brings over 15 years of corporate and M&A experience, having trained at a large multinational law firm and one of Calgary's most respected boutique firms. He is known for his ability to close difficult deals.
Together they bring legal, tax, financial, and business experience working in the same direction. For you. Your deal will not just be legally sound. It will be structured efficiently with your interests in mind, and protected from risks that only someone with that depth of experience would know to look for.
We are laser focused on one thing. The right outcome for you. Not just the legal outcome. The business outcome.
Only 1 in 20 Alberta business owners achieves a maximum value exit.
Sell Side Resources for Alberta Business Owners Looking to Sell
Understanding the business sale process is the first step toward a successful transaction. Outsiders Law regularly publishes practical guides and articles on buying and selling businesses in Alberta, exit planning, deal structuring, and tax efficiency.
NEW: Free Alberta Business Valuation Calculator
Wondering what your business is worth? Our free, confidential valuation tool gives you an indicative enterprise value range based on your industry, normalized EBITDA, and the key factors buyers actually use to price a business. Takes 5 minutes. Try it now.
NEW: Free Outsiders LOI Builder
Already know what your business is worth? Build a professionally structured Letter of Intent for your share purchase transaction in minutes. Free and confidential. Try it here.
Some helpful articles to get you started:
Visit our Knowledge Centre for the latest insights from our team.
Thinking of Selling Your Business?
Whether you are 5 months or 5 years out, the best time to talk to us is now. Early planning means better tax outcomes, better multiples, and fewer surprises at closing.
The fastest way to get a sense of where you stand is our free business valuation tool. It takes less than five minutes and gives you an instant estimate of what your business is worth today, and the factors that are affecting your valuation. A free consultation with our team will tell you the rest.
Frequently Asked Questions
How do I know if my business is ready to sell?
Most businesses can be sold. The question is whether they can be sold at maximum value. Buyers pay premium multiples for businesses that are organized, profitable, growing, and not dependent on the owner to operate. That said, your business can still be sold with you at the helm. You're likely to have to agree to stay on for a longer period of time to ensure a smooth transition. If your financials are clean, your contracts are documented, your IP is properly owned, and your team can run the business without you, you are in a strong position. If not, the right move might be to spend six to twelve months (or more) getting there before going to market. We can help you make that decision. The fastest way to get a sense of where you stand is our free business valuation tool. It takes less than five minutes and gives you an instant estimate of what your business is worth today, and the factors that are affecting your valuation. A free consultation with our team will tell you the rest.
Should I use a business broker to sell my business?
A broker and a lawyer serve different functions in a business sale. A broker finds buyers, markets your business, and manages the sale process from a commercial perspective. A lawyer protects your legal and financial interests throughout that process. Most sellers at the $3M+ level benefit from having both. What we can tell you is that having experienced M&A legal counsel involved before you engage a broker puts you in a much stronger position: First, we can help ensure that you aren't bound by a limiting engagement that costs you time and money to get out of. We know the difference between a quality broker and something often referred to in the industry as a "joker broker". A quality broker is worth their weight in gold, while a joker broker could be the most expensive mistake of your life. Second, you go into every conversation with a clear understanding of your legal position, your tax exposure, and what terms you should and should not accept. By the time a buyer is at the table, the most important decisions have already been made correctly. We work regularly with brokers and can recommend ones we trust if you need one.
How do I keep my business sale confidential?
Confidentiality is one of the most important and most overlooked parts of selling a business. If employees, customers, or competitors find out before the deal closes, it can damage the business and hurt your sale price. We protect confidentiality at every stage. Before any information is shared, we require signed NDAs. We build confidentiality obligations directly into the LOI and make them binding throughout the transaction and beyond if the deal falls apart. We limit the buyer's access to your employees during due diligence and work with both sides to carefully plan and manage how and when your team is informed, typically at or just before closing. Everything you share with us is also protected by solicitor-client privilege. The same applies to the buyer's counsel on their side. That privilege is one of the most important protections you have throughout the process.
What is the difference between a share purchase and an asset purchase?
In a share purchase, the buyer acquires the shares of the company and assumes everything that comes with it, including liabilities. In an asset purchase, the buyer selects specific assets and liabilities to acquire. Each structure has different tax implications for both the buyer and seller. Getting the structure right from the start is one of the most important decisions in any transaction. An asset purchase can give the buyer more control over which business assets are included in the business deal. This may include equipment, inventory, contracts, customer lists, intellectual property and other assets that are specifically identified in the sale agreement. It can also allow the buyer to avoid taking on certain liabilities that remain with the seller. A share purchase is often simpler from the seller’s perspective because the company itself continues to own its assets, contracts and operating relationships after the shares change hands. However, potential buyers may look more closely at historical liabilities, tax obligations and other risks because those generally remain within the corporation after closing. The choice between the two structures can also affect the overall economics of the transaction. A proper valuation of the company and its assets can help both sides understand how the purchase price is being allocated and whether the proposed structure reflects the value of what is actually being transferred.
Do I need both a lawyer and an accountant for my transaction?
Yes, and ideally they should be working together from the start rather than in silos. The legal and tax dimensions of an M&A transaction are deeply interconnected. One of Outsiders Law's key advantages is that our team thinks like both lawyers and business people, which means fewer gaps between legal and financial advice. To learn more, read this article: Do I Need Both a Lawyer and an Accountant for My Transaction?
How are legal fees structured for M&A transactions?
Most M&A is structured as hourly work due to the myriad of unknowns that can arise during the purchase and sale process. Depending on the complexity of the deal, we can provide a rough estimate as to where we expect the deal to end up from a cost perspective. Our fees will typically come in between half and two-thirds what it would cost to go to big law. To learn more, read this article: How Are Legal Fees Structured for M&A Transactions?
How long does it take to sell a business?
For a lower mid-market transaction in Alberta, most processes take 6 to 18 months from the decision to sell through to closing. An M&A broker will likely tell you it takes 9 months to prepare your business for sale. A tax planner will tell you that you need at least 2 years to optimize your structure for tax purposes. A business advisor would tell you that you need at least 3-5 years to truly prepare your business for sale. Complex deal structures often result in longer closing processes. Starting your preparation at least 2 to 3 years before your target exit date is strongly recommended.
When should I start planning to sell my business?
The honest answer is earlier than you think. Ideally three to five years before you want to close a deal. Early planning means better tax outcomes, a cleaner due diligence process, and ultimately a higher purchase price. To learn more, read this article: When Should I Start Planning to Sell My Business?
What affects my multiple the most?
The five factors that most affect your multiple are: owner dependency (can the business run without you), revenue quality (how much is recurring or under contract), growth trajectory (is EBITDA growing, flat, or declining), management team strength (who runs the business if you leave), and customer relationship ownership (are clients loyal to you personally or to the business). Our valuation tool assesses all five.
What is the Lifetime Capital Gains Exemption (LCGE)?
The LCGE allows eligible Canadian individuals to shelter a significant amount of capital gains from the sale of qualifying small business shares from tax. The exemption can potentially be multiplied across family members with proper planning. You need to start planning at least two years in advance to take full advantage of it. To learn more, read this article: What is the Lifetime Capital Gains Exemption?
Do I need both a lawyer and an accountant for my transaction?
Yes, and ideally they should be working together from the start rather than in silos. The legal and tax dimensions of an M&A transactions and privately negotiated purchases are deeply interconnected. One of Outsiders Law's key advantages is that our team thinks like both lawyers and business people, which means fewer gaps between legal and financial advice. The accountant may focus on valuation, tax and corporate finance matters, while legal counsel addresses deal structure, due diligence, regulatory compliance, the purchase agreement and closing documents. Close coordination between both advisors can reduce gaps and keep the acquisition process moving efficiently. To learn more, read this article: Do I Need Both a Lawyer and an Accountant for My Transaction?
Meet the Team
Outsiders Law's M&A practice is led by Sebastian Elawny and Chace Stokowski, two lawyers who between them bring a rare combination of legal, tax, financial, and business experience to every transaction.
Sebastian Elawny
Lawyerpreneur
Sebastian brings nearly two decades of big law-trained tax and transaction experience, including as head of the tax group at a large multinational law firm and as founding partner of the Business Law group at a Big 4 accounting firm.
He has led legal teams through an extensive range of M&A and commercial transactions, and as a business owner who has been through the process personally, he understands what is at stake on both sides of a deal.
E-mail: sebastian@outsiders.law
Chace Stokowski
Corporate & M&A Machine
Chace is a lawyer and CPA who came to law from a career in finance and audit. That background gives him a rare ability to analyze deals from both a legal and financial perspective simultaneously, identifying issues and opportunities that most lawyers simply would not see.
Clients value Chace for his practical, hands-on approach and his ability to align legal strategy with real world business goals. Chace works relentlessly to protect his clients' best interests.
E-mail: chace@outsiders.law
Sam Khajeei
M&A Deal Closer
Sam brings over 15 years of corporate, commercial, and M&A experience to Outsiders Law, having trained at a large multinational law firm and one of Calgary's most respected boutique firms. He has practiced internationally including in Dubai and the US.
Sam is known for his ability to close difficult deals. Clients value him for his directness, his commercial instincts, and his ability to cut through complexity without losing sight of what matters.
E-mail: sam@outsiders.law
Curran Dutta
Student-at-Everything
Curran supports Outsiders Law's M&A practice across every stage of a transaction. His work focuses on due diligence, disclosure schedules, and the drafting of closing documents, including resolutions, directions to pay, and receipts. Curran is the engine behind the closing process, ensuring that every document is accurate, complete, and ready when it needs to be.
E-mail: curran@outsiders.law
Calgary:
1900, 350-7th Ave SW
Phone: 587-333-3352
