Selling Your Canadian Business: A Step-by-Step Guide to Maximizing Value and Securing Your Legacy

The Shaughnessy Group
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Selling Your Canadian Business: A Step-by-Step Guide to Maximizing Value and Securing Your Legacy  is the roadmap you need to achieve a successful sale. Tailored for owners of businesses generating $5M to $50M in annual revenue, this podcast provides actionable steps to navigate the complex M&A process in Canada. From personal and family preparation to leveraging tax benefits like the Lifetime Capital Gains Exemption (LCGE), expert insights will help you maximize value and secure your legacy. #exitplanning #sell-side #sellmybusiness #entrepreneurship #exit #transition #succession #businesstransition #sellbusiness

  1. 2D AGO

    Financial Gaps to Address 24 Months Ahead of Selling a Business

    This podcast focuses on the most important financial gaps business owners should address at least 24 months before selling. It helps founders understand why early preparation plays such a critical role in valuation and how unresolved financial issues can quietly erode buyer confidence long before a deal reaches the finish line. Listeners will learn how common gaps such as disorganized financial records, underreported income, inconsistent profitability, and unresolved tax liabilities show up during a sale process. The episode explains why buyers care deeply about predictability, transparency, and risk, and how gaps in forecasting, recurring revenue, or documentation can directly impact pricing and deal structure. The discussion also outlines practical steps owners can take well ahead of an exit to strengthen financial clarity and reduce reliance on the founder. By addressing risks early and creating a more stable, scalable business, this podcast helps sellers approach the market with stronger positioning and a clearer path to maximizing value. Explore more insights, guides, and resources at www.Shaughnessy.Group You're listening to The Shaughnessy Group Podcast—insights on buying, selling, and growing Canadian businesses in the lower-middle market.Let's begin. This podcast is for informational purposes only and is not professional advice. Consult qualified advisors for your specific situation. Important Notice: These podcast notes are unofficial summaries created for personal reference and educational purposes only. They are not intended as a verbatim transcript, official record, or endorsement by the podcast hosts, guests, or producers of Shaughnessy Group. While every effort has been made to capture key insights, quotes, and discussions accurately, errors, omissions, or interpretations may occur due to the subjective nature of summarization. Listeners are strongly encouraged to refer to the original episode for full context, nuances, and original audio. No Advice Provided: The content discussed in Shaughnessy Group episodes, including these notes, does not constitute professional, financial, legal, medical, or investment advice. Any ideas, strategies, or opinions shared by guests are their own and should not be relied upon without independent verification and consultation with qualified professionals. Copyright & Usage: All rights reserved. These notes are derived from publicly available podcast episodes and are shared under fair use principles for non-commercial, transformative purposes. Reproduction, distribution, or commercial use without permission from the podcast creators is prohibited. For questions or permissions, contact the Shaughnessy team directly. Enjoy the learning, but always do your due diligence!

    14 min

  2. 4D AGO

    Key Financial Levers That Increase Business Valuation

    This podcast breaks down the key financial levers that directly influence business valuation during the exit phase. It is designed to help founders understand how buyers assess value and which financial drivers matter most when determining price, risk, and long term potential. Listeners will learn how revenue growth, profitability, operational efficiency, and customer diversification shape buyer perception and impact valuation multiples. The episode also explores the importance of a strong management team, disciplined asset management, and debt reduction, explaining how each lever can strengthen financial health and reduce perceived risk for acquirers. The conversation focuses on practical actions business owners can take before going to market to position their company for a stronger outcome. By highlighting how to improve financial performance and clearly demonstrate future growth potential, this podcast helps founders approach their exit with greater confidence and clarity. Explore more insights, guides, and resources at www.Shaughnessy.Group You're listening to The Shaughnessy Group Podcast—insights on buying, selling, and growing Canadian businesses in the lower-middle market.Let's begin. This podcast is for informational purposes only and is not professional advice. Consult qualified advisors for your specific situation. Important Notice: These podcast notes are unofficial summaries created for personal reference and educational purposes only. They are not intended as a verbatim transcript, official record, or endorsement by the podcast hosts, guests, or producers of Shaughnessy Group. While every effort has been made to capture key insights, quotes, and discussions accurately, errors, omissions, or interpretations may occur due to the subjective nature of summarization. Listeners are strongly encouraged to refer to the original episode for full context, nuances, and original audio. No Advice Provided: The content discussed in Shaughnessy Group episodes, including these notes, does not constitute professional, financial, legal, medical, or investment advice. Any ideas, strategies, or opinions shared by guests are their own and should not be relied upon without independent verification and consultation with qualified professionals. Copyright & Usage: All rights reserved. These notes are derived from publicly available podcast episodes and are shared under fair use principles for non-commercial, transformative purposes. Reproduction, distribution, or commercial use without permission from the podcast creators is prohibited. For questions or permissions, contact the Shaughnessy team directly. Enjoy the learning, but always do your due diligence!

    12 min

  3. 5D AGO

    Common Issues Found in Due Diligence and What Sellers Should Fix

    This podcast explores the most common issues buyers uncover during due diligence and why they so often determine whether a deal moves forward or falls apart. It is designed to help founders understand what buyers are really looking for when they review financials, operations, and risk, and how being unprepared can directly impact valuation and buyer confidence. Listeners will gain practical insight into frequent red flags such as inconsistent financial records, unresolved tax or legal issues, unhealthy cash flow, and overreliance on the founder. The episode walks through how these issues show up in due diligence and explains why they matter so much to buyers evaluating risk, sustainability, and future growth. Most importantly, this podcast focuses on what sellers can fix proactively before going to market. It covers concrete steps founders can take to clean up financials, strengthen documentation, improve forecasting, and position their business for a smoother process and stronger outcome. Whether you are planning an exit soon or years down the road, this episode helps you prepare with clarity and confidence. Explore more insights, guides, and resources at www.Shaughnessy.Group You're listening to The Shaughnessy Group Podcast—insights on buying, selling, and growing Canadian businesses in the lower-middle market.Let's begin. This podcast is for informational purposes only and is not professional advice. Consult qualified advisors for your specific situation. Important Notice: These podcast notes are unofficial summaries created for personal reference and educational purposes only. They are not intended as a verbatim transcript, official record, or endorsement by the podcast hosts, guests, or producers of Shaughnessy Group. While every effort has been made to capture key insights, quotes, and discussions accurately, errors, omissions, or interpretations may occur due to the subjective nature of summarization. Listeners are strongly encouraged to refer to the original episode for full context, nuances, and original audio. No Advice Provided: The content discussed in Shaughnessy Group episodes, including these notes, does not constitute professional, financial, legal, medical, or investment advice. Any ideas, strategies, or opinions shared by guests are their own and should not be relied upon without independent verification and consultation with qualified professionals. Copyright & Usage: All rights reserved. These notes are derived from publicly available podcast episodes and are shared under fair use principles for non-commercial, transformative purposes. Reproduction, distribution, or commercial use without permission from the podcast creators is prohibited. For questions or permissions, contact the Shaughnessy team directly. Enjoy the learning, but always do your due diligence!

    13 min

  4. JAN 30

    The One Thing to Increase Your Exit Valuation

    This podcast focuses on the single most important driver founders can influence today to increase their exit valuation: recurring revenue. It explains why buyers place such a premium on predictability and how stable revenue streams reduce perceived risk in an acquisition. Listeners will learn how recurring revenue directly impacts valuation multiples, smooths volatility, and gives buyers confidence in future earnings. The episode breaks down why businesses with subscriptions, long term contracts, and repeat customers consistently outperform transactional models during sale negotiations. The discussion also covers practical ways founders can build and strengthen recurring revenue, from shifting pricing models to improving customer retention and expanding complementary offerings. This episode is essential for founders who want to position their business for a higher value exit while building a stronger, more resilient company along the way.  Explore more insights, guides, and resources at www.Shaughnessy.Group You're listening to The Shaughnessy Group Podcast—insights on buying, selling, and growing Canadian businesses in the lower-middle market.Let's begin. This podcast is for informational purposes only and is not professional advice. Consult qualified advisors for your specific situation. Important Notice: These podcast notes are unofficial summaries created for personal reference and educational purposes only. They are not intended as a verbatim transcript, official record, or endorsement by the podcast hosts, guests, or producers of Shaughnessy Group. While every effort has been made to capture key insights, quotes, and discussions accurately, errors, omissions, or interpretations may occur due to the subjective nature of summarization. Listeners are strongly encouraged to refer to the original episode for full context, nuances, and original audio. No Advice Provided: The content discussed in Shaughnessy Group episodes, including these notes, does not constitute professional, financial, legal, medical, or investment advice. Any ideas, strategies, or opinions shared by guests are their own and should not be relied upon without independent verification and consultation with qualified professionals. Copyright & Usage: All rights reserved. These notes are derived from publicly available podcast episodes and are shared under fair use principles for non-commercial, transformative purposes. Reproduction, distribution, or commercial use without permission from the podcast creators is prohibited. For questions or permissions, contact the Shaughnessy team directly. Enjoy the learning, but always do your due diligence!

    13 min

  5. JAN 28

    Why 80% of Canadian Business Owners May Never Sell

    This podcast explores why so many Canadian business owners never complete a sale and what separates those who succeed from those who stall. It helps listeners understand the real barriers that prevent exits and why building a great business does not always translate into a sellable one. The episode covers the most common challenges owners face, including overvaluation, lack of preparation, owner dependency, and weak succession planning. It also looks at the uniquely Canadian factors that influence deal outcomes, such as market size, economic cycles, financing conditions, and industry specific pressures that affect buyer confidence. Most importantly, this podcast focuses on what owners can do differently. Listeners will gain practical insights on early planning, strengthening operations, aligning expectations with market realities, and working with the right advisors to improve their odds of a successful transition.  Explore more insights, guides, and resources at www.Shaughnessy.Group You're listening to The Shaughnessy Group Podcast—insights on buying, selling, and growing Canadian businesses in the lower-middle market.Let's begin. This podcast is for informational purposes only and is not professional advice. Consult qualified advisors for your specific situation. Important Notice: These podcast notes are unofficial summaries created for personal reference and educational purposes only. They are not intended as a verbatim transcript, official record, or endorsement by the podcast hosts, guests, or producers of Shaughnessy Group. While every effort has been made to capture key insights, quotes, and discussions accurately, errors, omissions, or interpretations may occur due to the subjective nature of summarization. Listeners are strongly encouraged to refer to the original episode for full context, nuances, and original audio. No Advice Provided: The content discussed in Shaughnessy Group episodes, including these notes, does not constitute professional, financial, legal, medical, or investment advice. Any ideas, strategies, or opinions shared by guests are their own and should not be relied upon without independent verification and consultation with qualified professionals. Copyright & Usage: All rights reserved. These notes are derived from publicly available podcast episodes and are shared under fair use principles for non-commercial, transformative purposes. Reproduction, distribution, or commercial use without permission from the podcast creators is prohibited. For questions or permissions, contact the Shaughnessy team directly. Enjoy the learning, but always do your due diligence!

    11 min

  6. JAN 27

    Empower Sellers: Maximize Value, Win Buyers with Key Tools

    This podcast is designed to help Canadian business owners prepare for a successful exit by understanding the tools that drive stronger outcomes in sell side transactions. It explains how the right preparation can reduce friction, increase confidence, and position a business to command better terms when going to market.  Listeners will learn how Information Request Lists bring structure and clarity to the sale process, helping management teams stay focused while uncovering opportunities to strengthen the business before buyers engage. The episode also explores sell side Quality of Earnings reports and how they establish credibility, validate sustainable earnings, and address buyer concerns before they become deal breakers.  By walking through real world benefits and practical considerations, this podcast equips sellers with insights to move faster, protect value, and stand out in competitive M and A markets across Canada. It is a valuable listen for owners, executives, and advisors who want to approach a sale with confidence and control.  Explore more insights, guides, and resources at www.Shaughnessy.Group  You're listening to The Shaughnessy Group Podcast—insights on buying, selling, and growing Canadian businesses in the lower-middle market.Let's begin. This podcast is for informational purposes only and is not professional advice. Consult qualified advisors for your specific situation. Important Notice: These podcast notes are unofficial summaries created for personal reference and educational purposes only. They are not intended as a verbatim transcript, official record, or endorsement by the podcast hosts, guests, or producers of Shaughnessy Group. While every effort has been made to capture key insights, quotes, and discussions accurately, errors, omissions, or interpretations may occur due to the subjective nature of summarization. Listeners are strongly encouraged to refer to the original episode for full context, nuances, and original audio. No Advice Provided: The content discussed in Shaughnessy Group episodes, including these notes, does not constitute professional, financial, legal, medical, or investment advice. Any ideas, strategies, or opinions shared by guests are their own and should not be relied upon without independent verification and consultation with qualified professionals. Copyright & Usage: All rights reserved. These notes are derived from publicly available podcast episodes and are shared under fair use principles for non-commercial, transformative purposes. Reproduction, distribution, or commercial use without permission from the podcast creators is prohibited. For questions or permissions, contact the Shaughnessy team directly. Enjoy the learning, but always do your due diligence!

    14 min

  7. JAN 22

    Benefits of Association Membership When Selling a Business

    This podcast explores how business association membership can play a valuable role when preparing to sell a business. It highlights why being part of an organized network can strengthen your position long before a transaction begins. Listeners will gain a clearer understanding of how associations support smarter planning and better outcomes during a sale. The episode covers key benefits such as access to industry knowledge, market insights, and educational resources related to valuation, exit strategies, and negotiations. It also explains how credibility and visibility gained through association membership can make a business more attractive to buyers while providing discreet ways to explore selling options. In addition, the podcast looks at the human side of selling a business, including peer support, mentorship, and trusted referrals to legal and financial professionals. Together, these advantages help owners reduce risk, improve leverage, and navigate the sale process with greater confidence. Explore more insights, guides, and resources at www.Shaughnessy.Group You're listening to The Shaughnessy Group Podcast—insights on buying, selling, and growing Canadian businesses in the lower-middle market.Let's begin. This podcast is for informational purposes only and is not professional advice. Consult qualified advisors for your specific situation. Important Notice: These podcast notes are unofficial summaries created for personal reference and educational purposes only. They are not intended as a verbatim transcript, official record, or endorsement by the podcast hosts, guests, or producers of Shaughnessy Group. While every effort has been made to capture key insights, quotes, and discussions accurately, errors, omissions, or interpretations may occur due to the subjective nature of summarization. Listeners are strongly encouraged to refer to the original episode for full context, nuances, and original audio. No Advice Provided: The content discussed in Shaughnessy Group episodes, including these notes, does not constitute professional, financial, legal, medical, or investment advice. Any ideas, strategies, or opinions shared by guests are their own and should not be relied upon without independent verification and consultation with qualified professionals. Copyright & Usage: All rights reserved. These notes are derived from publicly available podcast episodes and are shared under fair use principles for non-commercial, transformative purposes. Reproduction, distribution, or commercial use without permission from the podcast creators is prohibited. For questions or permissions, contact the Shaughnessy team directly. Enjoy the learning, but always do your due diligence!

    16 min

  8. JAN 21

    Sell Your Business to a Friend: Pros & Cons for Canadians

    This podcast examines the unique opportunity of selling your Canadian business to a friend and why it can be both appealing and risky. It helps business owners think clearly about whether bypassing a traditional market process truly serves their financial and personal goals. The episode is designed to bring perspective to a decision that often feels simple on the surface but carries long term consequences. Listeners will learn the key advantages of a friend-to-friend transaction, including speed, confidentiality, cost savings, and greater control over the future of the business. At the same time, the podcast explores the potential downsides, such as undervaluing the company, emotional bias in negotiations, legal exposure, and the strain that can arise when personal relationships intersect with complex financial deals. The discussion also outlines practical steps to protect yourself, from obtaining an independent valuation to maintaining professional standards in due diligence and documentation. Whether you are actively considering an offer from a friend or simply planning ahead, this episode provides clarity to help you make a confident, informed decision. Explore more insights, guides, and resources at www.Shaughnessy.Group You're listening to The Shaughnessy Group Podcast—insights on buying, selling, and growing Canadian businesses in the lower-middle market.Let's begin. This podcast is for informational purposes only and is not professional advice. Consult qualified advisors for your specific situation. Important Notice: These podcast notes are unofficial summaries created for personal reference and educational purposes only. They are not intended as a verbatim transcript, official record, or endorsement by the podcast hosts, guests, or producers of Shaughnessy Group. While every effort has been made to capture key insights, quotes, and discussions accurately, errors, omissions, or interpretations may occur due to the subjective nature of summarization. Listeners are strongly encouraged to refer to the original episode for full context, nuances, and original audio. No Advice Provided: The content discussed in Shaughnessy Group episodes, including these notes, does not constitute professional, financial, legal, medical, or investment advice. Any ideas, strategies, or opinions shared by guests are their own and should not be relied upon without independent verification and consultation with qualified professionals. Copyright & Usage: All rights reserved. These notes are derived from publicly available podcast episodes and are shared under fair use principles for non-commercial, transformative purposes. Reproduction, distribution, or commercial use without permission from the podcast creators is prohibited. For questions or permissions, contact the Shaughnessy team directly. Enjoy the learning, but always do your due diligence!

    14 min
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Selling Your Canadian Business: A Step-by-Step Guide to Maximizing Value and Securing Your Legacy  is the roadmap you need to achieve a successful sale. Tailored for owners of businesses generating $5M to $50M in annual revenue, this podcast provides actionable steps to navigate the complex M&A process in Canada. From personal and family preparation to leveraging tax benefits like the Lifetime Capital Gains Exemption (LCGE), expert insights will help you maximize value and secure your legacy. #exitplanning #sell-side #sellmybusiness #entrepreneurship #exit #transition #succession #businesstransition #sellbusiness

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