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Legacy: The Business Succession Podcast

Legacy: The Business Succession Podcast

Jared Pilon 69 Episodes Aug 18, 2026

A bi-weekly podcast focused on helping business owners plan a smooth exit from their company. It covers exit planning and succession planning strategies, offering tips and guidance for building a lasting legacy. The host, Jared Pilon, shares insights for entrepreneurs preparing to transition their business.

Episodes

Get the MAXIMUM VALUE in Your Business Sale
Get the MAXIMUM VALUE in Your Business Sale Aug 18, 2026 958 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 bes
Do You Actually Need a Holding Company?
Do You Actually Need a Holding Company? Aug 4, 2026 590 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 i
The Family Succession Mistake That Tears Businesses Apart
The Family Succession Mistake That Tears Businesses Apart Jul 21, 2026 830 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 charge
People Are NEVER the PROBLEM in Management Buyouts
People Are NEVER the PROBLEM in Management Buyouts Jul 7, 2026 1080 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 rare
YOUR SUCCESSION PATH: Family Transition or Third-Party Sale
YOUR SUCCESSION PATH: Family Transition or Third-Party Sale Jun 16, 2026 703 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-par
The HARDEST Part of SUCCESSION Planning
The HARDEST Part of SUCCESSION Planning Jun 2, 2026 651 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 5 Succession Mistakes That Cost Business Owners
The 5 Succession Mistakes That Cost Business Owners May 19, 2026 821 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, comp
Why Five Years Isn't Enough Time to Plan Your Business Exit
Why Five Years Isn't Enough Time to Plan Your Business Exit May 5, 2026 608 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 — w
An Exit Plan is Not a Succession Plan (& vice versa)
An Exit Plan is Not a Succession Plan (& vice versa) Apr 21, 2026 555 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 n
Your Business Exit WILL Happen. Will You PLAN or PANIC?
Your Business Exit WILL Happen. Will You PLAN or PANIC? Apr 7, 2026 583 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 unnec
What They Don't Tell You About Business Exit Planning
What They Don't Tell You About Business Exit Planning Mar 3, 2026 2241 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 mis
Save 100+ Hours Every Month With AI | EP060
Save 100+ Hours Every Month With AI | EP060 Feb 3, 2026 2684 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

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