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CORPORATE TAX PLANNING

Every business decision has a tax side, and the cheapest time to deal with it is before the decision is made. Our tax work follows a business through its life: setting up a structure, growing and reorganizing it, and eventually passing it on or selling it.​ We advise Canadian business owners on tax-sensitive decisions involving corporate structure, growth, acquisitions, and a future sale. Our tax counsel helps you understand the options before the decision is locked in. Outsiders Law brings big-law experience to businesses that want more than the same story, the same words given back to them. We create a structured plan for your private business to ensure top functionality.​​

Tax Counsel for Canadian Businesses

Structure & Reorganization

Your company’s structure affects how you bring in owners, move assets, expand, and transfer ownership. We help business owners assess and implement tax-conscious structures as their plans change.

Typical engagements include:

  • Reorganizing a corporate group

  • Reviewing asset transfers between entities

  • Assessing tax issues in an expansion outside Canada

  • Advising on whether private-company shares may qualify for RRSP or other registered-plan investments

  • Reviewing the tax implications of a proposed transaction

We help you understand how a proposed change may affect the business and its owners before you proceed.

Calgary
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Tax and the Sale of a Business

The way a sale is structured can affect the seller’s tax position and the buyer’s plans. We help owners assess tax considerations early, compare possible deal structures, and coordinate tax advice with the broader transaction.

 

Outsiders Law treats tax planning as part of preparing for a sale, not just a task to leave until closing.

Thinking of Buying or Selling a 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. 

Contractors, Employees and the CRA

Whether a worker is an employee or an independent contractor has payroll, source deduction, and reporting consequences for a business. We help companies set up contractor relationships so they hold up, and we act for businesses facing a CRA worker classification audit.

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CRA Questions About Your Contractors?

You don't need to hand over your books or dig up years of records to get a first read on your case. Answer four quick questions and find out if you qualify for a review, no documents, no obligation, about one minute of your time.

Bitcoin On Circuitry

Bitcoin &
Digital Asset Tax

Tax treatment for digital assets depends on how they’re acquired, held, and used in the business. Since 2018, we’ve advised businesses in the Bitcoin space, including mining operations, Lightning Network operators, and Bitcoin ATM businesses.

 

We help businesses assess tax issues connected to their activities and understand the rules that may apply.

Talk To Us Early

If a sale, restructuring or new venture is on the horizon, a conversation about tax now is usually cheaper than a fix later.

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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