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/

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

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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.

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/

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

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 risk
• Why owner dependency creates concentration risk buyers won’t pay for
• How poor succession planning can fracture teams
• The long-term value of early, gradual succession planning
• How succession planning protects wealth, relationships, and legacy

If 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

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 strategically
• Common exit strategies like family succession, management buyouts, and third-party sales
• Why doing less in your business makes it worth more
• Vendor takebacks and earnouts: When they work (and when they don't)
• Why having your documentation ready prevents buyers from walking away
• Proper 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

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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.

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 Framework
• Prompt engineering: This is why "write me an article" fails and what to do instead
• How to implement AI across your team without overwhelming them
• Security and boundaries that protect proprietary information
• What business owners must know about digital ethics and legal considerations
• Real business applications: from social media captions to eliminating repetitive tasks

Find 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

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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.

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 track
• Align your content to your actual demographic
• Consistency > vira trends
• Authenticity and ethics
• Why your content should challenge and connect
• The anti-spam rule: stop cold-pitching; build relationships first

Find 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

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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.

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 reduced
• How to calculate actual tax on the gain (not gross proceeds) on state and federal taxes
• Filing strategies that cut refund timelines from years to weeks
• ITIN essentials: why you need one, when to apply, and document pitfalls that cause delays
• How foreign tax credits work—and what proof CRA wants
• Filing order and calendars that help you avoid audit jams
• What 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

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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 Canadian dollar keeps sliding, and it’s hitting your long-term purchasing power. So how do you protect your savings when cash is quietly losing value? How to combat inflation

In this episode of Tax Talk, Jared sits down with investor and educator, Luke Spicer, to unpack why the CAD is weakening, how inflation really works, and whether gold and silver can serve as a practical hedge. We get into the silver-to-gold ratio, industrial demand for silver (EVs, solar, national defence), practical buying tips, storage options, and even how some Canadians hold physical metals inside registered accounts (RRSP, TFSA, RRIFs) through a trust company and compliant vaults.

What you’ll learn:

• Why the Canadian dollar is struggling and how “invisible taxes” like inflation erode savings
• Currency vs. money: why gold and silver have held purchasing power across history
• How premiums, spot vs. market price, and buybacks actually work when purchasing metals
• Storage choices, including at-home vs. insured vaults in Canada/offshore
• Liquidity, volatility, implementation, and separating signal from hype
• Why idle cash in bank accounts can be a drag and how to think in “purchasing power” terms

Find us at:

https://www.legacyllp.ca/

reception@legacyllp.ca

Need to get in touch with Luke?

Find Luke Spicer on LinkedIn.

#InvestmentStrategies #HowToCombatInflation #InvestInGold

00:00 Kicking it off

00:47 Overview of the episode

01:23 The Canadian Dollar keeps diving

06:13 Investing in silver and gold is still out of the norm

09:53 Silver and gold investment performance

16:25 A physical investment for security

23:16 Versus investing in RRSPs, RRIFs, LIFs, Etc.

29:56 Inflation education

42:22 Wrapping it up

40:49 Wrapping it all up

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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.