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

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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.

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.

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.