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. 1d ago

    Get the MAXIMUM VALUE in Your Business Sale

    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 why they are often willing to pay a significant premiumThe three things every strategic buyer evaluates before making an offer and how to make sure your business scores well on all threeWhy contracts, documented systems, and strong management teams directly increase your sale priceSix negotiation strategiesThe best business sales do not start when the offer arrives. They start years earlier, by building a business that is organized, transferable, and attractive to the right buyer. Download Legacy's Business Succession Planning eBook at legacyllp.ca. It's free and designed to help you begin building a more valuable, more transferable business long before a sale is ever on the table. https://www.legacyllp.ca/resources/ebooks/business-succession-planning-canada Find us at: https://www.legacyllp.ca/ reception@legacyllp.ca Timestamps: 00:00 Kicking it off 01:48 Your business's worth 04:32 Strategic buyers 07:57 The hard part of the sale 10:55 My 6 pieces of advice 13:58 Wrapping it up #BusinessSale #BusinessSuccession #StrategicBuyers ________________________________________ 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 our information is accurate, we cannot always guarantee that the information on this website, blog or podcast is always correct, complete or up-to-date.

  2. Aug 4

    Do You Actually Need a Holding Company?

    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 most business owners don't hear until it's too late is that by the time you start asking questions about corporate structure, some of the best planning opportunities have already passed you by. What You'll Learn in This Episode: What a holding company actually isWhy not every incorporated business needs oneHow surplus assets left inside an operating company create unnecessary legal and financial riskWhy separating retained earnings and real estate into a holding company creates flexibilityWhy the Lifetime Capital Gains Exemption requires advance planningThe business owners who benefit most from holding company planning are not the ones who set it up because someone told them to. They are the ones who built their structure with a clear purpose, years before a transition was ever on the table. Download Legacy's Business Succession Planning eBook at legacyllp.ca. It's free and meant for business owners navigating these decisions right now. https://www.legacyllp.ca/resources/ebooks/business-succession-planning-canada Find us at: https://www.legacyllp.ca/ reception@legacyllp.ca Timestamps: 00:00 Kicking it off 01:42 Should I have a holding company? 02:55 What is a holding company? 04:49 The reason for a HoldingCo 07:30 Timing planning 08:07 Wrapping it up #holdingcompany #businesssuccession #HoldCo ________________________________________ 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 our information is accurate, we cannot always guarantee that the information on this website, blog or podcast is always correct, complete or up-to-date.

  3. Jul 21

    The Family Succession Mistake That Tears Businesses Apart

    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 control when the people involved are not just shareholders, but family. While transferring a business to the next generation may sound straightforward, the reality is almost always more complicated. What You'll Learn in This Episode:  Why equal ownership does not automatically create a fair outcome for everyone involved Why the question "what outcome are we actually trying to achieve?" matters more than any ownership percentage Why ownership and control are not the same thing Why avoiding these conversations creates far more conflict than having them early How gradual leadership transitions, started years in advance, create options that last-minute planning never willDownload Legacy's Business Succession Planning eBook at legacyllp.ca. It's free and meant for business owners navigating these decisions right now. https://www.legacyllp.ca/resources/ebooks/business-succession-planning-canada Find us at: https://www.legacyllp.ca/ reception@legacyllp.ca Timestamps 00:00 Kicking it off 01:57 Equal isn't always fair 06:30 Ownership vs control 09:36 The BIG mistake 11:41 Wrapping it up #businesssuccession #familybusiness #exitplanning ________________________________________ 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.

  4. Jul 7

    People Are NEVER the PROBLEM in Management Buyouts

    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 management buyouts attract owners who care about more than just the sale price How vendor financing and vendor take-back loans make MBOs possible, and what risk they carry for the seller The difference between being a great manager and being ready to be an owner Why authority must transfer alongside ownership, and what happens when it doesn't Why the strongest management buyouts begin years before any shares are ever soldThis episode is for educational purposes only and does not constitute specific legal, tax, or financial advice. Download Legacy's Business Succession Planning eBook at legacyllp.ca. It's free and meant for business owners navigating these decisions right now. https://www.legacyllp.ca/resources/ebooks/business-succession-planning-canada Find us at: https://www.legacyllp.ca/ reception@legacyllp.ca Timestamps 00:00 Kicking it off 02:49 Why Management Buyouts work 04:13 The money problem 08:43 Managers become owners 12:37 Letting go of the business 15:49 Wrapping it up #managementbuyout #businesssuccession #MBO ________________________________________ 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.

  5. Jun 16

    YOUR SUCCESSION PATH: Family Transition or Third-Party Sale

    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 come with each plan. Use this podcast to guide you to which path is right for you based on your priorities, your values, and what you want your business transition to look like. What You'll Learn in This Episode:  Why interest in the business does not automatically equal readiness to lead it How to navigate ownership fairness when multiple family members are involved Why third-party buyers often pay more, and why higher valuation is not always the deciding factor What happens to employees, culture, and community when a third-party sale closes How to align your succession path with what matters most: maximum value, continuity, family legacy, employee stability, or community impact  Find us at: https://www.legacyllp.ca/ reception@legacyllp.ca Timestamps: 00:00 Kicking it off 01:04 A successful family business transition 04:45 Third-party sale path 06:17 Real world examples 08:04 Timelines 10:13 3 Key Takeaways 10:40 Wrapping it up #FamilyBusinessSuccession #BusinessTransition #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.

  6. Jun 2

    The HARDEST Part of SUCCESSION Planning

    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 identity, their purpose, and their daily life for decades. This episode explores why so many technically ready business owners delay their exit, and how to better prepare themselves for life after ownership. What You'll Learn in This Episode:  Why business owners who are financially ready to exit still delay "Who am I without this business?" is the question that stops succession planning in its tracks The difference between an owner who transitions gradually and one who faces a sudden stop Why letting go of control is a process, not a single decision The reframe that makes succession planning feel manageable: instead of asking when to leave, ask what it would look like to be slightly less involved next yearDownload 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 it off 01:02 Life after your exit 05:06 The most common reason exits are delayed 05:34 Letting go of control 07:45 Transition in small steps 09:14 3 Practical Takeaways 09:45 Wrapping it up #BusinessExitPlanning #ExitStrategy #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.

  7. 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.

  8. 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.

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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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