Capital Gains Tax When Selling a Business Canada: Essential Guide for Entrepreneurs in 2025
By Jeff Barrington, Managing Director · Windsor Drake Selling a business in Canada can trigger significant tax implications, particularly regarding capital gains tax. When entrepreneurs sell their business assets or shares, they typically face taxation on the difference between the selling price and the original cost. In Canada, individuals and small business owners generally pay […]
How to Structure a Business Sale in Canada: A Step-by-Step Guide for Entrepreneurs
Home›Research›How to Structure a Business Sale in Canada How to Structure a Business Sale in Canada: A Step-by-Step Guide for Entrepreneurs Windsor DrakePublished Apr 28, 2025Updated October 21, 2026 By Jeff Barrington, Managing Director OverviewLegal frameworkValuationSale structureLegal stepsProceeds and taxAfter the saleFAQ Short answer A Canadian business sale is structured as a share sale, an […]
How to Sell a Business Without Losing Your Team: Essential Strategies for a Smooth Transition
By Jeff Barrington, Managing Director · Windsor Drake Selling your business marks a significant milestone, but it can also trigger anxiety among employees who worry about their future. Communicating the sale effectively is crucial to maintain team stability during this transition. Having key team members involved in the sale process makes it faster and easier […]
What Is a Quality of Earnings Report: Understanding Financial Analysis for Investment Decisions
By Jeff Barrington, Managing Director · Windsor Drake When you’re buying a business or seeking investors, understanding the true financial health of a company goes beyond standard financial statements. A quality of earnings report digs deeper to reveal how sustainable and reliable a company’s profits really are. This specialized financial analysis examines revenue streams, expense […]
Exit Planning for Canadian Business Owners: Strategic Steps for a Successful Transition in 2025
By Jeff Barrington, Managing Director · Windsor Drake Planning your business exit isn’t just about retirement, it’s about securing the legacy you’ve worked so hard to build. Many Canadian entrepreneurs spend decades growing their companies but neglect to develop a clear strategy for eventually stepping away. A well-crafted exit plan should begin at least 18 […]
How to Find a Buyer for Your Business: A Strategic Guide for Selling Successfully
By Jeff Barrington, Managing Director · Windsor Drake Selling a business can feel overwhelming, but finding the right buyer doesn’t have to be complicated. Many business owners struggle with knowing where to start and who might be interested in purchasing their company. You can find potential buyers through personal networks, business brokers, or online marketplaces […]
Should I Sell Shares or Assets in My Business: Making the Right Decision for Your Financial Future
By Jeff Barrington, Managing Director · Windsor Drake When selling your business, one of the biggest decisions you’ll face is whether to sell shares or assets. This choice affects how much tax you’ll pay, what risks you’ll carry, and the overall value you’ll receive. Sellers often prefer share sales because they typically result in lower […]
Cybersecurity M&A Update – January 2025
By Jeff Barrington, Managing Director · Windsor Drake The cybersecurity industry remains one of the most dynamic and rapidly evolving sectors in technology. With cyber threats becoming increasingly sophisticated, businesses are prioritizing robust security measures. This demand has propelled mergers and acquisitions (M&A) activity within the sector to unprecedented levels. Windsor Drake’s Cybersecurity M&A Update […]
Tech M&A Due Diligence Checklist: A Comprehensive Guide
Home›Research›Tech M&A Due Diligence Checklist Tech M&A Due Diligence Checklist for Founders Windsor DrakePublished Dec 12, 2024Updated October 21, 2026 By Jeff Barrington, Managing Director OverviewWhy it mattersChecklistRed flagsHow we helpFurther readingConclusionFAQ In brief A tech M&A due diligence checklist covers seven areas: financials (three to five years of statements, recurring revenue, burn rate and […]
Tech M&A Risks and Mitigation
By Jeff Barrington, Managing Director · Windsor Drake Mergers and acquisitions (M&A) are a critical strategy for growth, innovation, and market expansion in the tech industry. However, they come with inherent risks that can derail even the most promising deals. For tech companies, the stakes are particularly high given the fast-paced nature of the industry, […]