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TAX AND THE SALE OF A BUSINESS

Calgary Night View

Tax planning for a business sale or acquisition

The structure of a business sale or acquisition can affect the parties’ tax positions, the assets or shares involved, and the terms they negotiate. Those decisions often arise before the purchase agreement is finalized.

We advise business owners and buyers on tax considerations connected to transactions. We help identify issues early, assess possible deal structures, and coordinate tax advice with the legal work on the transaction.

Planning to buy or sell?

A conversation early in the process can help identify the tax questions that deserve attention before the transaction terms are settled.

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Why timing matters

Once negotiations advance, some options may become harder to pursue or may affect the deal’s terms. Getting tax advice early can help you understand the implications of different approaches before you commit to one.

If you are considering a sale, planning ahead may give you time to review your structure and prepare for a transaction. If you are buying, early advice can help you assess how the proposed structure fits your objectives and what tax questions should be addressed in the documents.

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How we can help

Depending on the transaction, our work may include:

  • Reviewing the tax implications of a share or asset transaction

  • Assessing the seller’s existing corporate structure

  • Identifying tax issues that may affect the proposed purchase price or terms

  • Considering tax consequences of reorganizations before a sale

  • Reviewing tax provisions in letters of intent and purchase agreements

  • Coordinating transaction tax advice with your accountant and other advisors

  • Helping address tax questions that arise during negotiations

The appropriate analysis depends on the parties, the business, the assets, and the proposed terms.

Peace bridge and Calgary view

Tax is part of deal planning.

​A transaction involves more than choosing a purchase price. The structure, timing, allocation of value, and closing arrangements can all matter. We work with you and your transaction advisors to identify the tax questions, explain the available options, and incorporate the agreed approach into the legal work.

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Why Outsiders?

Tax decisions are connected to the way a business is owned, operated, and planned for the future. Outsiders Law brings tax and business law experience together, so the advice can account for the wider transaction or ownership picture.

We work directly with business owners and coordinate with their accountants and other advisors. Our goal is to explain the issues clearly, help you understand your options, and support the next decision.

Meet the Team

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Sebastian Elawny

Lawyerpreneur

​

Before founding Outsiders Law, Sebastian was named as tax counsel on numerous publicly reported
Canadian transactions, including the $1.258 billion Gibson Energy sale, the Sinopec/Addax Petroleum
transaction
, the $198 million Parex/Verano acquisition, and Shaw Communications’ public debt and preferred-
share offerings
.
He was recognized with a 2018 Client Choice Award for Corporate Tax in Alberta and
appeared in Lexpert’s 2015 Rising Stars winners list.

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Pierce Quaghebeur

Tax Savings Strategist

​

​Pierce is a tax and corporate lawyer at Outsiders Law who makes sure the deal a client signs is also the right deal at tax time. Before joining Outsiders, he spent five years in the corporate tax and private client services group of a large national law firm, advising private corporations and their owners on tax and succession planning and corporate governance. He began his legal career in Edmonton, where he articled and practiced tax and general corporate law.

Frequently Asked Questions

© 2026 by Outsiders Law

Calgary: 587-333-3352

Toronto: 647-692-2214

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