Legacy: The Business Succession Podcast

Jared Pilon
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A bi-weekly podcast that helps guide business owners towards a smooth exit from the legacy they have built with exit planning and succession planning strategies and tips.

  1. MAY 19

    The 5 Succession Mistakes That Cost Business Owners

    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 You'll Learn in This Episode:  Why waiting too long is the single most common and most damaging succession mistake How focusing exclusively on tax efficiency creates blind spots that affect what you actually receive Why avoiding difficult conversations delay conflict rather than preventing it How overestimating your business value derails deals What exit documentation actually needs to include Download Legacy’s Business Succession Planning eBook on our website to begin evaluating your readiness and start the right conversations today.  https://www.legacyllp.ca/resources/ebooks/business-succession-planning-canada Find us at: https://www.legacyllp.ca/ reception@legacyllp.ca Timestamps: 00:00 Kicking off the episode 01:09 First Mistake: Starting too late 02:39 Second Mistake: Focusing just on taxes 04:46 Third Mistake: Avoiding conversations 06:36 Fourth Mistake: Overestimating value 08:20 Fifth Mistake: No documented plan 12:05 Key takeaways 13:03 Wrapping it up #successionplanning #successionplanningmistakes #businesssuccession ________________________________________ Disclaimer By using this website, blog or podcast, users agree as follows: The information, services and/or products are for general information only and any reliance on the information provided therein is done at your own risk. If you make tax, accounting, investing or legal decisions after accessing this website, blog or podcast, it is recommended that you consult a qualified professional first. The views and opinions expressed are those of the author, seller, guests or publisher and do not necessarily reflect the views of the organizations or businesses that these individuals are associated with. Although we make strong efforts to make sure my information is accurate, we cannot always guarantee that the information on this website, blog or podcast is always correct, complete or up-to-date.

    14 min

  2. MAY 5

    Why Five Years Isn't Enough Time to Plan Your Business Exit

    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 always earlier than expected.  What You'll Learn in This Episode:  Why the "five years before retirement" assumption leaves business owners underprepared How corporate structure and tax planning require years of advance preparation Why leadership development and reducing founder dependency take time, not transactions The one question every business owner should be asking themselves right nowIf you've built something meaningful, it deserves a transition that is thoughtful, gradual, and entirely on your terms, not one forced by circumstance. Download Legacy’s Business Succession Planning eBook on our website to begin evaluating your readiness and start the right conversations today.  https://www.legacyllp.ca/resources/ebooks/business-succession-planning-canada Find us at: https://www.legacyllp.ca/ reception@legacyllp.ca Timestamps: 00:00 Kicking off the episode 00:40 When you should plan your exit 01:58 Corporate structure  02:48 Leadership development 03:58 Governance and communication 05:19 Business value 06:30 Your personal identity 08:38 3 Practical Takeaways 09:34 Wrapping it up #BusinessExitPlanning #SuccessionPlanning #BusinessValue ________________________________________ Disclaimer By using this website, blog or podcast, users agree as follows: The information, services and/or products are for general information only and any reliance on the information provided therein is done at your own risk. If you make tax, accounting, investing or legal decisions after accessing this website, blog or podcast, it is recommended that you consult a qualified professional first. The views and opinions expressed are those of the author, seller, guests or publisher and do not necessarily reflect the views of the organizations or businesses that these individuals are associated with. Although we make strong efforts to make sure my information is accurate, we cannot always guarantee that the information on this website, blog or podcast is always correct, complete or up-to-date.

    10 min

  3. APR 21

    An Exit Plan is Not a Succession Plan (& vice versa)

    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 planning begins, and why the gap between them is where transitions go wrong. What You'll Learn in This Episode:  Why exit planning and succession planning answer two completely different questions How exit planning focuses on transaction mechanics Why succession planning focuses on continuity What happens when an exit plan is built, but the succession foundation is not Why reactive planning compresses your options and increases stress during negotiations Three practical takeaways to integrate both approaches early and retain flexibility and confidenceYou've built something meaningful; it deserves more than a signed share purchase agreement. Your business deserves a transition that protects your wealth, your people, and the business itself. Download Legacy's Business Succession Planning eBook to assess your readiness and identify the gaps in your current plan. https://www.legacyllp.ca/resources/ebooks/business-succession-planning-canada Find us at: https://www.legacyllp.ca/ reception@legacyllp.ca Timestamps: 00:00 Kicking off the episode 00:37 The difference between succession planning and exit planning 03:44 What can go wrong if you have one plan without the other 04:44 The When and How 07:40 Three Practical Takeaways 08:42 Wrapping it all up #BusinessSuccession #ExitPlanning #SuccessionPlanning

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

    APR 7

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

    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: How lack of planning reduces valuation and increases riskWhy owner dependency creates concentration risk buyers won’t pay forHow poor succession planning can fracture teamsThe long-term value of early, gradual succession planningHow succession planning protects wealth, relationships, and legacyIf you’ve built something meaningful, it deserves a thoughtful, intentional transition; not a rushed decision made under pressure. Download Legacy’s Business Succession Planning eBook on our website to begin evaluating your readiness and start the right conversations today.  https://www.legacyllp.ca/resources/ebooks/business-succession-planning-canada Find us at: https://www.legacyllp.ca/ reception@legacyllp.ca Timestamps: 00:00 Introducing the episode 02:10 What exactly is succession planning? 03:11 What creates value in a business 04:14 The relational impact of your exit 05:52 Succession planning timelines 08:11 Wrapping it up #BusinessSuccessionPlanning #ExitPlanning #SuccessionPlanning

    10 min

  5. MAR 3

    What They Don't Tell You About Business Exit Planning

    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 "selling when you want to, not when you need to" is the key to maximizing your business value in this podcast episode. What you’ll learn: Understanding market windows and why you should time your exit strategicallyCommon exit strategies like family succession, management buyouts, and third-party salesWhy doing less in your business makes it worth moreVendor takebacks and earnouts: When they work (and when they don't)Why having your documentation ready prevents buyers from walking awayProper funding strategies using life insurance Find us at: https://www.legacyllp.ca/ reception@legacyllp.ca Need to get in touch with Travis? Travis Koivula Island Savings Wealth Management tkoivula@islandsavings.ca Timestamps: 00:00 Kicking it off 01:47 Start planning your business exit 05:51 Be prepared: Avoid deal fatigue 11:28 Family succession strategy 16:49 Third-party sales 18:13 Management buyouts 20:38 Tax implications of a business sale 27:17 Contingency plans 31:50 Vendor take-backs 35:25 Wrapping it all up #BusinessExitPlan #SuccessionPlanning #ExitStrategy ________________________________________ Disclaimer: By using this website, blog or podcast, users agree as follows: The information, services and/or products are for general information only and any reliance on the information provided therein is done at your own risk. If you make tax, accounting, investing or legal decisions after accessing this website, blog or podcast, it is recommended that you consult a qualified professional first. The views and opinions expressed are those of the author, seller, guests or publisher and do not necessarily reflect the views of the organizations or businesses that these individuals are associated with. Although we make strong efforts to make sure my information is accurate, we cannot always guarantee that the information on this website, blog or podcast is always correct, complete or up-to-date.

    37 min

  6. FEB 3

    Save 100+ Hours Every Month With AI | EP060

    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 less you do in your business, the more valuable AI becomes in this podcast episode. What You'll Learn: The LEARNED FrameworkPrompt engineering: This is why "write me an article" fails and what to do insteadHow to implement AI across your team without overwhelming themSecurity and boundaries that protect proprietary informationWhat business owners must know about digital ethics and legal considerationsReal business applications: from social media captions to eliminating repetitive tasksFind us at: https://www.legacyllp.ca/ reception@legacyllp.ca Need to get in touch with Taylor? Taylor Arancibia Unveiling Innovations taylor@unveilinginnovations.com Timestamps: 00:00 Kicking it off 01:47 AI: a Teammate or a Tool? 06:13 Implementing AI in your business 10:42 Prompting AI 15:29 Structuring AI use 26:59 Using AI to move your business forward 33:12 A tool to expand roles 40:00 The legal side of AI 42:44 Wrapping it all up ________________________________________ Disclaimer: By using this website, blog or podcast, users agree as follows: The information, services and/or products are for general information only and any reliance on the information provided therein is done at your own risk. If you make tax, accounting, investing or legal decisions after accessing this website, blog or podcast, it is recommended that you consult a qualified professional first. The views and opinions expressed are those of the author, seller, guests or publisher and do not necessarily reflect the views of the organizations or businesses that these individuals are associated with. Although we make strong efforts to make sure my information is accurate, we cannot always guarantee that the information on this website, blog or podcast is always correct, complete or up-to-date.

    45 min

  7. JAN 6

    Trying to Beat “The Algorithm”? Do This Instead

    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, and timing. We also cover ethics and authenticity, so you don’t tank your audience’s trust chasing trends. What you’ll learn: There’s no single algorithm, and what platforms really trackAlign your content to your actual demographicConsistency > vira trendsAuthenticity and ethicsWhy your content should challenge and connectThe anti-spam rule: stop cold-pitching; build relationships firstFind us at: https://www.legacyllp.ca/ reception@legacyllp.ca Need to get in touch with Joe? Joe Whitbread jsm) – Joe Social Media whitbread@joesocialmedia.com 403-391-2553 Timestamps: 00:00 Kicking it off 00:43 Overview of the episode 01:20 What are algorithms? 06:00 The impact of algorithms on your business 17:11 Consistency, engagement & timing 25:02 Tool & tips for creating content 37:49 Wrapping it all up #SocialMediaStrategy #SmallBusinessMarketing #Algorithm ________________________________________ Disclaimer: By using this website, blog or podcast, users agree as follows: The information, services and/or products are for general information only and any reliance on the information provided therein is done at your own risk. If you make tax, accounting, investing or legal decisions after accessing this website, blog or podcast, it is recommended that you consult a qualified professional first. The views and opinions expressed are those of the author, seller, guests or publisher and do not necessarily reflect the views of the organizations or businesses that these individuals are associated with. Although we make strong efforts to make sure my information is accurate, we cannot always guarantee that the information on this website, blog or podcast is always correct, complete or up-to-date.

    40 min

  8. 12/02/2025

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

    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 practical roadmap to a clean exit. What you’ll learn: FIRPTA explained: why buyers withhold up to 15% at closing and how/when it can be reducedHow to calculate actual tax on the gain (not gross proceeds) on state and federal taxesFiling strategies that cut refund timelines from years to weeksITIN essentials: why you need one, when to apply, and document pitfalls that cause delaysHow foreign tax credits work—and what proof CRA wantsFiling order and calendars that help you avoid audit jamsWhat to do if you haven’t reported prior U.S./Canadian rental income Find us at: https://www.legacyllp.ca/ reception@legacyllp.ca Need to get in touch with Steven? Steven Flynn Andersen LLP steven.flynn@ca.andersen.com Timestamps 00:00 Kicking it off 01:32 Overview of the Foreign Investment and Real Property Tax Act (FIRPTA) 05:42 Other tax obligations as a Canadian owning an American property 11:56 Tax credit application processes & timelines 18:32 Common mistakes 21:41 What to look out for when buying a property in the US 23:48 Bonus tips 27:31 Wrapping it all up ________________________________________ Disclaimer: By using this website, blog or podcast, users agree as follows: The information, services and/or products are for general information only and any reliance on the information provided therein is done at your own risk. If you make tax, accounting, investing or legal decisions after accessing this website, blog or podcast, it is recommended that you consult a qualified professional first. The views and opinions expressed are those of the author, seller, guests or publisher and do not necessarily reflect the views of the organizations or businesses that these individuals are associated with. Although we make strong efforts to make sure my information is accurate, we cannot always guarantee that the information on this website, blog or podcast is always correct, complete or up-to-date.

    30 min
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A bi-weekly podcast that helps guide business owners towards a smooth exit from the legacy they have built with exit planning and succession planning strategies and tips.

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