The Shaughnessy Group
Selling Your Canadian Business: A Step-by-Step Guide to Maximizing Value and Securing Your Legacy
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 #businesstran...
Author
The Shaughnessy Group
Category
Podcast website
Latest episode
Jul 8, 2026
Where to listen?
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Episodes
A Business Owner's Transformation: From Tax Focus to Buyer Focus 01.06.2026 21:07
This episode chronicles a business owner’s journey from prioritizing tax avoidance to maximizing company value through the process of financial normalization . Initially, the entrepreneur relied on accounting methods that minimized reported income to reduce tax liabilities, which inadvertently obscured the company’s true profitability . By engaging a specialist to create normalized financial state...
A Business Owner's Enlightenment: Understanding Tax Planning Value 01.06.2026 20:33
This episode follows the journey of Veronica, a successful business owner who discovers the critical distinction between standard accounting compliance and specialized tax planning during a company sale. Initially resistant to hiring an outside expert, Veronica eventually learns that her company's excess passive assets disqualified her from significant tax exemptions. By engaging a specialist...
An Entrepreneur's Awakening: Learning to Trust 01.06.2026 20:13
This episode chronicles the professional journey of Patricia, a successful software entrepreneur who initially attempted to sell her company through a private, unassisted negotiation. Although her independent nature made her skeptical of professional consulting fees, she eventually sought guidance from mergers and acquisitions experts after receiving an undervalued offer from a competitor. This de...
A Business Owner's Revelation: Seeing Through Buyers' Eyes 01.06.2026 18:44
This episode describes the transformative journey of a business owner named Thomas as he prepares to exit his industrial equipment company. Initially confident in his success, Thomas undergoes a rigorous readiness assessment that exposes critical vulnerabilities, including aging inventory , owner dependency , and financial inconsistencies . By choosing to delay his sale and systematically address...
The $3 Million Mistake 30.05.2026 12:55
This episode serves as an introduction to an M&A guide specifically designed for Canadian business owners looking to sell their companies. It begins with a cautionary tale of an entrepreneur who lost out on three million dollars because he failed to create a competitive bidding environment. The author emphasizes that achieving a maximum valuation requires more than just hard work; it demands s...
A Founder's Journey: From Doubt to Clarity 30.05.2026 21:19
This episode follows a construction entrepreneur named Michael as he navigates the complex emotional and financial transition of selling his multi-million dollar company. After years of resistance, health concerns and a desire for family time prompt him to move past his fear of irrelevance and define his core motivations. By establishing a clear "Why Sell?" statement, he successfully fil...
CEO Buying a Business / Seeking Acquisition / Buy a Business 28.05.2026 9:37
This podcast episode explores the mindset, strategy, and preparation required for CEOs and entrepreneurs looking to acquire a business. Whether pursuing growth through acquisition, entering a new market, or accelerating expansion, listeners will gain practical insight into how successful buyers evaluate opportunities, identify risks, and position themselves for long term success in the acquisition...
Buying or Selling a Business: How Much Is It Worth Today? 27.05.2026 13:01
This podcast episode explores how changing economic conditions, market uncertainty, and shifting business trends are influencing the value of privately owned companies today. From the impact of supply chain disruptions and workforce challenges to evolving buyer demand and record levels of available investment capital, listeners will gain a clearer understanding of why business valuations can vary...
Planning the Sale of Your Business? 25.05.2026 14:40
This podcast episode explores the key considerations business owners should understand before preparing to sell their company, including whether a holding company structure could benefit their long term strategy. Listeners will gain insight into the differences between operating companies and holding companies, how assets can be protected, and why many entrepreneurs use these structures as part of...
Private Company Acquisition 21.05.2026 14:49
In this podcast episode, we explore the process of private company acquisition and what buyers, investors, and business owners need to know when navigating a successful transaction. The discussion covers how private acquisitions are structured, why companies pursue acquisitions for growth, and the strategic opportunities that can emerge through ownership transitions. Listeners will gain insight in...
Foreign Investors to Buy a Company Make Direct Investment 19.05.2026 12:20
In this podcast episode, we explore how foreign investors can buy a company through direct investment and what this process means for business owners, entrepreneurs, and global investors. The discussion breaks down the fundamentals of foreign direct investment, including ownership structures, investment strategies, and the key financial considerations involved in acquiring a company across borders...
Everything You Need to Know About Adjusted EBITDA 18.05.2026 11:57
This podcast episode breaks down one of the most important financial metrics used in buying and selling private businesses, adjusted EBITDA. It is designed to help business owners, buyers, and advisors understand how earnings are normalized to reflect the true cash-generating ability of a company. By explaining what EBITDA is and how adjustments are applied, the episode provides clarity on a metri...
Eleven Reasons to Sell Your Business 14.05.2026 13:38
This podcast explores the most important personal and strategic reasons business owners decide to sell their company. It is designed to help entrepreneurs recognize the signals that may indicate it is the right time to begin planning an exit. From retirement and partnership disputes to market pressure and shifting personal priorities, the episode breaks down the real-world factors that influence o...
Is It Time to Sell Your Business? 13.05.2026 12:32
This podcast explores one of the most important questions every business owner eventually faces: is it time to sell your business? It takes you through the emotional and practical journey of entrepreneurship, from building a company with years of effort and personal sacrifice to recognizing when it may be time to transition out and realize the value you have created. It is designed to help owners...
Business Owners; What You Need to Know About Due Diligence 11.05.2026 13:09
This podcast episode provides a clear and practical guide for business owners on the importance of due diligence when preparing to sell, finance, or acquire a business. It explains how due diligence serves as a structured process for identifying risks, validating information, and ensuring that major business decisions are made with full transparency. Whether you are planning a sale or responding t...
How Wealth Managers Aid in Your Business Sale 06.05.2026 13:58
This podcast explores the important role Wealth Managers play in guiding business owners through the process of selling their company. It is designed for entrepreneurs who are beginning to think about exit planning and want to understand how financial planning, investment strategy, and long-term wealth decisions connect directly to a successful business sale. The discussion highlights how wealth m...
Did You Receive Unsolicited Interest in Buying Your Business? 05.05.2026 12:10
This podcast episode explores what it really means when you receive unsolicited interest in buying your business. It explains why buyers approach companies directly, what they are typically looking for, and how to interpret their motivations. Rather than reacting emotionally or rushing into discussions, the episode helps business owners understand how to assess early interest with clarity and conf...
Make Selling Your Business Easy With These Seven Steps 04.05.2026 15:49
This podcast is designed for business owners who are preparing for one of the most important decisions in their entrepreneurial journey, selling their business. It breaks down the process into clear, practical steps that help you understand how to approach a sale with confidence, clarity, and strategy. Whether you are planning ahead or already considering an exit, this series helps you see your bu...
10 Reasons Why Owners Should Get a Business Valuation. 03.05.2026 11:17
This podcast episode explores the 10 most important reasons why every business owner should obtain a professional business valuation, regardless of whether they are planning to sell, grow, or transition their company. Listeners will gain a clearer understanding of how valuation is not just a number for a potential sale, but a strategic tool that supports long term decision making and business succ...
Business Protection? – Why Owners Should Get a Business Value. 30.04.2026 11:05
In this podcast episode, we explore why understanding the value of your business is essential for protecting one of your most important assets. An independent business valuation provides owners with an objective view of their company’s worth and can serve as a foundation for long term planning. Whether your business is a startup, in a growth phase, or well established, knowing its enterprise value...
What Is Your Time to Transition as a Canadian Business Owner? 29.04.2026 11:21
In this podcast episode, we explore an important question many entrepreneurs eventually face: what is your timeline to transition out of your business? For Canadian business owners, planning an exit or ownership transition requires careful preparation, strategic thinking, and a clear understanding of the value of the company you have built. This episode discusses why defining your transition timel...
Estate Planning? – Why Owners Should Get a Business Valuation. 27.04.2026 12:30
In this podcast episode, we explore why understanding the value of your business is a critical part of estate planning and long term financial strategy. An independent business valuation provides owners with an objective view of their company’s enterprise value and can serve as a starting point for important decisions related to succession, transition planning, and protecting the future of the bus...
Selling a Business: 9 Reasons the Sale of Your Business May Fail 21.04.2026 14:16
Selling a business is a major milestone for many entrepreneurs, but the process is rarely simple. In this podcast episode, we explore nine common reasons why business sales fail and what Canadian business owners can do to avoid these costly pitfalls. From unqualified buyers to financial discrepancies discovered during due diligence, we discuss how small issues can quickly derail what should be a s...
Five Things to Consider When Selling Your Business. 21.04.2026 14:32
Selling a privately held business can be one of the most significant decisions an entrepreneur will ever make. In this podcast episode, we explore five key considerations business owners should evaluate before entering the sales process. While running a business requires expertise in operations, customers, and growth, selling a company introduces a completely different set of challenges that invol...
How Long Till Canadian Business Owners Exit? 20.04.2026 12:04
In this podcast episode, we explore one of the most common questions business owners ask when planning their transition: how long it actually takes to exit a business. Many owners underestimate the time required to properly prepare their company for sale, but a successful exit often begins years before the transaction takes place. This episode explains why early planning is essential and how prepa...
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