You spent decades building a successful business and received an offer worth millions. Then you discover the most valuable tax exemption available to Canadian business owners isn't available to you.

It’s because nobody checked whether your corporation actually qualified before the sale happened.

In this episode of Legacy: The Business Succession Podcast, host Jared Pilon of Legacy Accounting LLP breaks down the Lifetime Capital Gains Exemption, which is currently $1.25 million for qualifying property. He explains why simply owning an incorporated business doesn't automatically mean you qualify. This is the episode that could save you — or cost you — hundreds of thousands of dollars.

What You'll Learn in This Episode:

• What specific conditions must be satisfied
• Why a highly successful business can actually create its own LCGE qualification problem through accumulated passive assets
• Why LCGE planning is exit planning, not just sale planning, and why a deemed disposition on death makes this relevant to every business owner
• Why the best time to ask whether your shares qualify is when there is no transaction on the table

You don't always get to choose when your exit happens. A buyer can arrive unexpectedly. Your health can change. Life doesn't always wait for your five-year plan. The question is whether your business will be ready when that moment comes.

Download Legacy's Business Succession Planning eBook at legacyllp.ca. It's free and designed to help you start asking the right questions long before you're sitting across the table from a buyer.

https://www.legacyllp.ca/resources/ebooks/business-succession-planning-canada

Find us at:

https://www.legacyllp.ca/

[email protected]

Timestamps

00:00 Kicking it off

00:52 Lifetime Capital Gain Exemption

01:38 Qualifying

06:45 Farms don't always qualify

07:43 Shares that don't qualify

09:23 Your timeline

14:35 Ask your accountant

15:03 Wrapping it up

#LifetimeCapitalGainsExemption #businesssuccession #taxplanning

________________________________________
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 podcast is always correct, complete or up-to-date.

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 premium
• The three things every strategic buyer evaluates before making an offer and how to make sure your business scores well on all three
• Why contracts, documented systems, and strong management teams directly increase your sale price
• Six negotiation strategies

The 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/

[email protected]

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.

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 is
• Why not every incorporated business needs one
• How surplus assets left inside an operating company create unnecessary legal and financial risk
• Why separating retained earnings and real estate into a holding company creates flexibility
• Why the Lifetime Capital Gains Exemption requires advance planning

The 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/

[email protected]

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.

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 will

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/

[email protected]

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.

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 sold

This 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/

[email protected]

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.

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/

[email protected]

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.

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/

[email protected]

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/

[email protected]

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.

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 now

If 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/

[email protected]

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.

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 confidence

You'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/

[email protected]

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