The numbers are ready. The structure is in place. Your team is ready. So why can't you move forward? In this episode of Legacy: The Business Succession Podcast, host Jared Pilon of Legacy Accounting LLP addresses the part of succession planning that rarely gets talked about: the personal side. For most business owners, the biggest barrier to a successful transition is not the tax structure or the deal mechanics. It is the challenge of stepping away from something that has defined their identi...

Most succession planning failures are not technical; they’re behavioural. And they are avoidable if you know what to look for. In this episode of Legacy: The Business Succession Podcast, Jared Pilon of Legacy Accounting LLP walks through the five most common succession planning mistakes business owners make. Each mistake on its own is manageable. Together, they can quietly erode business value, compress your options, and turn a well-intentioned transition into a costly, stressful event. What ...

When should you actually start planning your business exit? Most business owners assume the answer is five years before retirement. In practice, that timeline is almost always too late. In this episode of Legacy: The Business Succession Podcast, host Jared Pilon of Legacy Accounting LLP addresses one of the most common questions business owners ask when they first begin thinking about succession — when should planning actually start? The answer, backed by real-world experience, is almost alwa...

Most business owners use succession planning and exit planning interchangeably. That mistake can cost you everything you've built. In this episode of Legacy: The Business Succession Podcast, we draw a clear line between two business practices that look similar on the surface but serve fundamentally different purposes. One protects your financial outcome. The other protects your business. You need both. Most owners only have one. Find out exactly where exit planning ends and succession plannin...

Every business owner will exit their business. The only question is whether it happens on your terms or under pressure. In this episode of Legacy: The Business Succession Podcast, host Jared Pilon of Legacy Accounting LLP breaks down why succession planning isn’t optional, even if retirement feels far away. You’ll learn why waiting to plan cuts your options, reduces business value, and creates unnecessary stress for your family, employees, and customers. What We’ll Also Cover in This Episode:...

Thinking about selling your business, but don't know where to start? In this episode of the Tax Talk Podcast, Jared Pilon from Legacy Accounting LLP sits down with Travis Koivula, Investment Advisor at Island Savings Wealth Management, to unpack everything you need to know about successfully exiting your business. Learn why most business owners wait too long to plan their exit and how that mistake costs them thousands. We’ll also reveal the critical three-year minimum planning window and why ...

We’ve all treated AI like a fancy search engine and gotten frustrated with the results. In this episode of Tax Talk Podcast, Jared Pilon from Legacy Accounting LLP sits down with Taylor Arancibia, founder of Unveiling Innovations, to reveal how to transform AI from a basic tool into your business's secret weapon. Learn why treating AI like a human teammate produces exponentially better results than one-off queries. Taylor also reveals how businesses are saving 100+ hours monthly and why the l...

Chasing hacks to “beat the algorithm” is a time sink. In this Tax Talk episode, Jared and Joe Whitbread cut through the noise and show you how small businesses actually win on social: by reverse-engineering their audience, showing consistent brand presence, and documenting the real work you do. We break down why there isn’t one algorithm, how platforms read your behaviour, and why separating personal and business use matters. You’ll learn the simplest growth levers: consistency, engagement, a...

If you’re selling a U.S. vacation home or rental as a Canadian, don’t let FIRPTA withholding, state taxes, and cross-border filings trap your cash for years. In this Tax Talk episode, Jared talks with cross-border tax pro Steven Flynn about how Canadians can sell U.S. real estate the right way. That means minimizing withholding, avoiding double taxation, speeding up refunds, and sidestepping CRA headaches. From ITINs and state returns to foreign tax credits and forex gains, this is your pract...

The Canadian dollar keeps sliding, and it’s hitting your long-term purchasing power. So how do you protect your savings when cash is quietly losing value? How to combat inflation In this episode of Tax Talk, Jared sits down with investor and educator, Luke Spicer, to unpack why the CAD is weakening, how inflation really works, and whether gold and silver can serve as a practical hedge. We get into the silver-to-gold ratio, industrial demand for silver (EVs, solar, national defence), practical...