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Legacy: The Business Succession Podcast

Legacy: The Business Succession Podcast

By: 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.

© 2026 Legacy: The Business Succession Podcast
Episodes
  • YOUR SUCCESSION PATH: Family Transition or Third-Party Sale
    Jun 16 2026

    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.

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    12 mins
  • The HARDEST Part of SUCCESSION Planning
    Jun 2 2026

    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 year

    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 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.

    Show More Show Less
    11 mins
  • The 5 Succession Mistakes That Cost Business Owners
    May 19 2026

    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.

    Show More Show Less
    14 mins
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