Legacy: The Business Succession Podcast

Handing your business to the team that helped you build it is the obvious move. But management buyouts fail more often than you expect. In this episode of Legacy: The Business Succession Podcast, I’m breaking down how management buyouts work, why they appeal to so many business owners, and, most importantly, the reasons they break down before they ever get across the finish line. The people are ra...

A family transition or a third-party sale. Which succession path is right for you? Every business owner will eventually face this question. And the answer is rarely as straightforward as it seems. In this episode of Legacy: The Business Succession Podcast, host Jared Pilon of Legacy Accounting LLP explores the two succession paths available to most business owners: a family transition or a third-p...

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...

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, co...

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 —...

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...

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 unn...

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 mi...

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 result...

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 perso...

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 h...

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...

Canadian homeowners: what if your mortgage could help you build wealth, reduce taxes, and help you pay off your mortgage sooner—without increasing your monthly payments? In this episode of the Tax Talk Podcast, I sit down with Nick Cox at The Smith Manoeuvre to break down how Canadians can convert non-deductible mortgage interest into tax-deductible investment interest using a re-advanceable HELOC...

Confused by RSPs, TFSAs, and other investment opportunities but still want to grow your legacy of wealth? Join us as we break down Canada's key investment accounts and reveal tax-saving strategies that could save you thousands. What You'll Discover: RSP withdrawal timing TFSA optimization for tax-free growth and inheritance planning New FHSA secrets for first-time homebuyers Investment t...

Corporate life insurance represents one of the most powerful yet misunderstood financial tools available to you as a business owner. While you may recognize its potential benefits, the complexity surrounding these policies often leads to poor decisions that can impact your business operations and estate planning. On this episode of the Tax Talk Podcast, we’re cutting through the complexity to deli...

On this episode of the Tax Talk Podcast, we are joined by Garth Epp, the co-owner of Your Limits Lifted and an expert on business coaching, mentorship and the provision of online, web-based tools. We are exploring the Working Geniuses model. Your team members can fit into the six Working Geniuses: Wonder, Invention, Discernment, Galvanizing, Enablement and Tenacity. We’ll look at how you can get t...

We’re joined by Joe Whitbread of Jo(e) Social Media to discuss how you can find the hidden opportunities in your side hustle. With inflation creeping up, its becoming more appealing to bankroll a cashflow. In this Tax Talk Podcast, we’re sharing unique ways to broaden your side hustle and see more cash in your pocket.  Joe Whitbread  jsm) – Joe Social Media   whitbread@joesocialmedia.com 403-391-2...

In this episode of the Tax Talk Podcast, we are chatting with David Prowse about the emotional side of exiting your business. You will speak with your account and lawyer about the tax and legal side of the sale, but do you consider the emotional aspects that come with selling your business? Do you have a plan in place that will ensure that you are happy and fulfilled when you move on from that pro...

In this episode of the Tax Talk Podcast, we are looking at how you can build your financial legacy through smart real estate investments. Real estate investment offers numerous opportunities for you to accumulate wealth and gain financial independence. With careful financial planning and the assistance of a professional accountant, you can get the most out of your investment. We are joined by Bryc...

Effective marketing is crucial to business success, yet many small business owners struggle with it. Marketing, like financial planning, requires expertise and a structured approach. In this episode of the Tax Talk Podcast, we are shedding some light on this topic.  We are joined by Peter DeWit from EDGE Marketing & Design. We'll be exploring the most necessary marketing aspects for small...

You’ve spent years growing your company and building financial security. But are you maximizing your retirement savings? If you're over 40, an Individual Pension Plan (IPP) could be a smart strategy to help you secure your financial legacy while reducing your business taxes. In this episode, we are joined by Kit Richmond from MacDougall Wealth Management Group. We’ll break down what an IPP is...

When managing a corporate real estate portfolio, the decision to move your rental properties into a corporation can have a significant financial impact on your rental operation. Understanding both the benefits and drawbacks of this process will enable you to make informed decisions suited to your circumstances and goals. Let’s look at the key insights and considerations of incorporating your real...

As 2024 draws to a close, proactive tax planning is essential for individuals and businesses to optimize their financial outcomes ahead of the 2025 tax season. This year’s economic landscape, marked by fluctuating interest rates and persistent inflation, has underscored the importance of creating financial and tax strategies. By addressing tax considerations now, you can effectively manage tax obl...

Ensure your business continues on successfully and put a plan in place to preserve your legacy with estate planning. Topics Discussed: Determining who will take over your business Your timeline for transferring your business Set the purchase price for your business Determining the division of your assets upon your passing Are there charities you would like to include, and is tax mitigation importa...

After you've utilized your business as a vehicle to generate wealth, it's time to plan for a pension. What does this mean for your business? You need to take into consideration several factors when you are planning for a pension and the different options that are available to you. Let's discuss pension planning for business owners who have generated wealth through your business.  To...