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PODCAST

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

The Shaughnessy Group

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

business entrepreneurship

All Episodes

13:54

Financial Gaps to Address 24 Months Ahead of Selling...

Selling Your Canadian Business: A Step-by-Step Guide... ·

2026/02/05

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 d...

en-ca

11:58

Key Financial Levers That Increase Business Valuation

Selling Your Canadian Business: A Step-by-Step Guide... ·

2026/02/03

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 ma...

en-ca

13:14

Common Issues Found in Due Diligence and What Sellers...

Selling Your Canadian Business: A Step-by-Step Guide... ·

2026/02/02

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,...

en-ca

13:04

The One Thing to Increase Your Exit Valuation

Selling Your Canadian Business: A Step-by-Step Guide... ·

2026/01/30

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 contra...

en-ca

11:21

Why 80% of Canadian Business Owners May Never Sell

Selling Your Canadian Business: A Step-by-Step Guide... ·

2026/01/28

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 infl...

en-ca

14:15

Empower Sellers: Maximize Value, Win Buyers with Key...

Selling Your Canadian Business: A Step-by-Step Guide... ·

2026/01/27

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 opportuni...

en-ca

16:06

Benefits of Association Membership When Selling a...

Selling Your Canadian Business: A Step-by-Step Guide... ·

2026/01/22

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...

en-ca

13:54

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

Selling Your Canadian Business: A Step-by-Step Guide... ·

2026/01/21

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 sp...

en-ca

14:14

Best Practices for Selling Your Canadian Business Safely

Selling Your Canadian Business: A Step-by-Step Guide... ·

2026/01/19

This podcast explores the essential steps Canadian business owners need to take to sell their companies safely and strategically. It focuses on how to reduce risk, protect value, and avoid common pitfalls that can arise during a sale process. Listeners will gain clarity on how proper planning and informed decision making can lead to a smoother and more successful transaction. Across the episode, we cover best practices for safeguarding employees, customers, suppliers, and intellec...

en-ca

15:05

How Bankers Build a Buyer List for Your Canadian...

Selling Your Canadian Business: A Step-by-Step Guide... ·

2026/01/16

This podcast helps Canadian business owners understand how investment bankers identify and prioritize the right buyers when preparing a business for sale. It breaks down the strategy behind building a buyer list and explains why this step is critical to maximizing value, maintaining confidentiality, and creating competitive tension in a sale process. Listeners will learn how bankers analyze a business, define ideal buyer profiles, and use market research, industry data, and professional netwo...

en-ca

12:08

How to Pick the Best Intermediary to Sell Your Business

Selling Your Canadian Business: A Step-by-Step Guide... ·

2026/01/15

This podcast guides Canadian business owners through one of the most important decisions in the sale process choosing the right intermediary to represent their business. It explains how the right broker, M&A advisor, or investment bank can directly impact valuation, buyer quality, confidentiality, and overall deal success, helping owners avoid costly missteps and missed opportunities. Listeners will learn what to look for when evaluating intermediaries, including experience, credentials, ...

en-ca

10:04

Key Considerations for Business Owners Thinking of...

Selling Your Canadian Business: A Step-by-Step Guide... ·

2026/01/13

This podcast explores the key considerations Canadian business owners need to understand before selling a lower-middle-market company. It breaks down how buyers think about value, risk, and opportunity, helping owners see their business through the lens of private equity firms, strategic acquirers, and management teams. By focusing on preparation, transparency, and timing, the episode helps owners position their companies for a stronger, more confident exit. Listeners will learn what truly d...

en-ca

14:48

Be Prepared for Due Diligence When Selling Your Business

Selling Your Canadian Business: A Step-by-Step Guide... ·

2025/12/13

This episode breaks down exactly how Canadian business owners can get ahead of the due diligence process when preparing to sell a company generating one to three million in annual EBITDA. You will learn why thorough preparation is essential for speeding up the deal timeline, increasing buyer confidence, and strengthening your negotiating position. Through clear guidance and real world Canadian context, the discussion highlights how organized financials, transparent documentation, and early pl...

en-ca

12:57

Going to Market

Selling Your Canadian Business: A Step-by-Step Guide... ·

2025/12/12

This episode walks you through the pivotal moment when you decide to take your Canadian business to market and how the right M&A intermediary can make all the difference. Aimed at owners of companies generating 5M to 50M in annual revenue, the conversation explains how to attract serious, qualified buyers while protecting confidentiality, minimizing disruption, and positioning your business for a premium valuation. You will hear exactly how a strategic go to market plan can boost competit...

en-ca

13:44

Quality of Earnings (Q of E) Report – Building Trust

Selling Your Canadian Business: A Step-by-Step Guide... ·

2025/12/06

This episode breaks down how a Quality of Earnings report strengthens trust, enhances transparency, and sets the financial foundation for a successful business sale in the Canadian mid-market. You’ll learn why validating the sustainability of your earnings is essential and how a well-prepared Q of E can reduce surprises, ease buyer concerns, and support a higher valuation. The discussion highlights how this analysis goes beyond traditional accounting to reveal the proper drivers of performanc...

en-ca

10:27

Setting Up the Virtual Data Room (VDR)

Selling Your Canadian Business: A Step-by-Step Guide... ·

2025/12/06

This episode explores how a well-structured Virtual Data Room supports a smooth and competitive sell-side M&A process for Canadian mid-market business owners. Listeners will learn why early data readiness, clear organization, and controlled buyer access form the backbone of an efficient due diligence phase. The conversation highlights how these steps build credibility, protect confidentiality, and strengthen the Initial Opinion of Value that guides the deal. You will hear practical guidan...

en-ca

16:10

Choosing the Right Sell-Side Strategy for Your...

Selling Your Canadian Business: A Step-by-Step Guide... ·

2025/11/29

This podcast breaks down how Canadian lower middle market business owners can choose the right sell side strategy when preparing for an exit. By exploring the differences between broad auctions, limited auctions, and negotiated sales, listeners gain a clear understanding of how each approach supports goals such as maximizing valuation, protecting confidentiality, or accelerating timelines. The episode explains how independent M&A advisors tailor these processes and why strategic preparati...

en-ca

15:07

Second Bite: A Lucrative Exit for Canadian Owners

Selling Your Canadian Business: A Step-by-Step Guide... ·

2025/11/28

This episode explores how Canadian business owners can unlock significant value through a second bite exit strategy by selling a majority stake while staying actively involved in the business. Listeners will learn how this approach provides upfront liquidity, shared risk, and access to capital that supports expansion, acquisitions, and long term growth. The podcast breaks down why this model often outperforms scaling a company independently, especially in Canada’s competitive and capital cons...

en-ca

11:19

Retired Entrepreneur Shares Lessons Selling A Family...

Selling Your Canadian Business: A Step-by-Step Guide... ·

2025/11/21

This episode explores the real-world journey of selling a long-standing family business through the experience of retired entrepreneur Chantal Hampson. Listeners will learn how a combination of preparation, clarity, and the right buyer mindset can transform an uncertain transition into a rewarding exit. The story offers practical takeaways for anyone considering a sale, whether the goal is retirement, a new direction, or simply creating space for the next generation to lead. Through Chantal’s...

en-ca

14:52

Determining Your Business’s Value

Selling Your Canadian Business: A Step-by-Step Guide... ·

2025/11/20

This episode guides Canadian business owners through the essential first step of any successful sale, understanding what your business is truly worth. You will learn why obtaining an informed opinion of value sets the tone for negotiations, shapes buyer expectations, and ensures you enter the market with confidence. By breaking down the valuation process into clear, practical steps, this podcast helps you see how early preparation can significantly influence your outcome. We explore the most ...

en-ca

60 results

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