Legacy: The Business Succession Podcast

Epizode

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  Get the MAXIMUM VALUE in Your Business Sale 18.08.2026 15min

  In this episode of Legacy: The Business Succession Podcast, host Jared Pilon of Legacy Accounting LLP reveals what you need to do, years before you ever list your business, to put yourself in the strongest possible position to get paid more when the time comes to sell. The truth most business owners don't hear until it's too late is that the highest offer doesn't always go to the best business. It goes to the best prepared one. What You'll Learn in This Episode: What a strategic buyer is and ...
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  Do You Actually Need a Holding Company? 04.08.2026 9min

  Everyone seems to have an opinion on holding companies. Your lawyer mentioned it. Another business owner swears by it. You read something about it online. But nobody has clearly explained whether you actually need one. In this episode of Legacy: The Business Succession Podcast, I’m cutting through the noise on one of the most misunderstood topics in business succession planning. A holding company is a tool, and like any tool, it only works when it is used for the right job. But the reality mo...
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  The Family Succession Mistake That Tears Businesses Apart 21.07.2026 13min

  Splitting everything equally among your children sounds like the fair and reasonable thing to do. But in family business succession, "equal" and "fair" are not always the same thing. Assuming they are is one of the most common mistakes that breaks both businesses and families. In this episode of Legacy: The Business Succession Podcast, I tackle one of the most emotionally charged aspects of succession planning: family transfers. Specifically, how business owners can balance fairness and contr...
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  People Are NEVER the PROBLEM in Management Buyouts 07.07.2026 18min

  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 rarely the problem. The structure almost always is. What You'll Learn in This Episode: Why ma...
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  YOUR SUCCESSION PATH: Family Transition or Third-Party Sale 16.06.2026 11min

  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-party sale. He’ll break down the trade-offs, emotional dynamics, and structural requirements that ...
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  The HARDEST Part of SUCCESSION Planning 02.06.2026 10min

  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...
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  The 5 Succession Mistakes That Cost Business Owners 19.05.2026 13min

  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 ...
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  Why Five Years Isn't Enough Time to Plan Your Business Exit 05.05.2026 10min

  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...
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  An Exit Plan is Not a Succession Plan (& vice versa) 21.04.2026 9min

  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...
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  Your Business Exit WILL Happen. Will You PLAN or PANIC? 07.04.2026 9min

  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:...
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  What They Don't Tell You About Business Exit Planning 03.03.2026 37min

  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 ...
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  Save 100+ Hours Every Month With AI | EP060 03.02.2026 44min

  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...
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  Trying to Beat “The Algorithm”? Do This Instead 06.01.2026 39min

  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...
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  Save on Taxes When Selling U.S. Property: For Canadians 02.12.2025 29min

  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...
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  Your MONEY vs. INFLATION: Investing in Gold & Silver | EP 57 04.11.2025 44min

  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...
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  Build Wealth With Your Mortgage | EP 56 07.10.2025 42min

  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. You’ll learn the “Plain Jane” foundation, the five accelerators, who this strategy fits best, r...
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  Tax-Smart Investing Made Simple | EP 055 09.09.2025 37min

  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 timingTFSA optimization for tax-free growth and inheritance planningNew FHSA secrets for first-time homebuyersInvestment types explained: stocks, bonds, ETFs, and alternativesCorporate vs. personal investment tax strategiesHouse fli...
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  Corporate Life Insurance: 3 Questions You Need to Ask | EP 054 06.08.2025 44min

  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 deliver practical, actionable insights for business owners considering corporate life insurance as pa...
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  Unlocking Your Employees’ Max Potential with the Six Working Geniuses | EP 053 08.07.2025 46min

  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 the most out of your employees, and how to get them into the right seats in your business. Ensure ...
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  The Hidden Opportunities in Your Side Hustles | EP 052 06.06.2025 39min

  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 403-391-2553 00:00 Intro 00:49 Overview of episode 01:52 What is holding you back fr...