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Tax Implications of Selling Your Business in Canada

Selling Your Business in Canada

Selling a business is one of the biggest financial decisions an entrepreneur can make. Beyond negotiating the right price, business owners need to carefully consider how the sale will be structured, since taxes can drastically affect how much money you actually keep. Read More

Written by MadanCA Team on September 11, 2025 @ 5:49 pm
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Tax Implications of Selling Your Business in Canada

Selling a business is one of the biggest financial decisions an entrepreneur can make. Beyond negotiating the right price, business owners need to carefully consider how the sale will be structured, since taxes can drastically affect how much money you actually keep.

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Estate Planning in Canada: Avoiding Unnecessary Taxes for Your Heirs

Estate planning is about more than just deciding who will inherit your assets. In Canada, when someone passes away, the Canada Revenue Agency (CRA) treats their assets as if they were sold at fair market value the day before death. This is called a “deemed disposition”, which can create a significant tax bill for your … Continue reading Estate Planning in Canada: Avoiding Unnecessary Taxes for Your Heirs

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First Year U.S. Tax Issues for Canadians | Cross Border Tax Mississauga

First Year U.S. Tax Issues for Canadians Moving to the U.S. More Canadians are crossing the border to live in the U.S. than ever before, whether for career growth, business opportunities, education, or family. While the excitement of a new chapter is undeniable, moving to the U.S. means stepping into a very different tax system … Continue reading First Year U.S. Tax Issues for Canadians | Cross Border Tax Mississauga

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Understanding HST in Canada: A Guide for Businesses

As a Canadian accountant, I often get asked about HST: what it is, how to register for it, and how businesses can manage it efficiently. Whether you’re a small business owner just starting out or a seasoned entrepreneur, understanding HST is crucial to keeping your business compliant and optimizing your tax strategy.

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Ultimate Guide to Cross-Border Tax for Canadians and Americans

Managing taxes is already complex – add international borders to the mix, and it becomes even more challenging. Whether you’re a Canadian investing in the U.S., an American living in Canada, or a snowbird splitting time between both countries, you need to understand how tax laws on both sides of the border affect you.

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Flipping Houses? Here’s How The CRA Classifies Your Profits

House flipping has become a popular way to build wealth in Canada, especially as real estate prices have surged. The basic idea – buy a property, renovate it, and sell it quickly for profit –  sounds simple. But from the Canada Revenue Agency’s (CRA) point of view, flipping can carry complex tax consequences, and you … Continue reading Flipping Houses? Here’s How The CRA Classifies Your Profits

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5 Tax Tips for High Income Earners In Canada

As your income rises, so does your marginal tax rate, which means proactive tax planning is a must. High-income earners – which is considered an annual salary of $115,000+ in Canada – face some of the steepest tax rates in Canada, but there are smart, legal strategies to help keep more of your hard-earned dollars. … Continue reading 5 Tax Tips for High Income Earners In Canada

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Doing Business in the U.S. for Canadian Companies

Chapter 1: Introduction The United States is the world’s largest economy and most dynamic consumer market, making it an attractive destination for Canadian companies seeking expansion. With strong bilateral trade, close geography, a shared language, and cultural familiarity, the U.S. is a natural next step for Canadian entrepreneurs. However, entering the U.S. market requires a … Continue reading Doing Business in the U.S. for Canadian Companies

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Tax Rules for Airbnb & Short-Term Rentals in Canada

Short-term rentals through platforms like Airbnb, VRBO, and Booking.com have become a popular strategy for Canadians to generate additional income. However, these rental activities come with important income tax and GST/HST implications. As of January 1, 2024, new federal legislation has introduced even stricter rules, particularly regarding municipal compliance. This article outlines the key tax … Continue reading Tax Rules for Airbnb & Short-Term Rentals in Canada

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Canadian Tax Strategy Using Barbados & St. Lucia

In today’s global environment of tax transparency and regulatory alignment, entrepreneurs and consultants must structure their businesses with care. The goal is to achieve legitimate tax efficiency while maintaining full compliance with local and international laws. A proven strategy that meets this objective involves using a dual-jurisdiction structure incorporating entities in Barbados and St. Lucia.

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