The Shaughnessy Group

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

Business EN ↓ 140 episodes

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

Business

Latest episode

Jul 8, 2026

Where to listen?

Podcasts in the app Replaio Radio Coming soon

Podcasts are coming to the app soon. Install now and be the first to see a whole new take on podcasts

Get it on Google Play Install for free Android 5M+ downloads · 4.8 rating iOS soon

Episodes

How to Attract Financial versus Strategic Buyers 19.02.2026

This podcast helps Canadian business owners understand how to position their company to attract the right type of buyer during a sale process. It explains the fundamental differences between financial buyers and strategic buyers, and why each group evaluates opportunities through a very different lens. By understanding these distinctions, owners can better align their exit strategy with buyer expe...

What Are the Reporting Gaps That Lead an M&A Deals Collapse 18.02.2026

This podcast helps Canadian business owners understand why accurate financial reporting is critical to a successful M&A transaction. It explains how reporting gaps can quickly erode trust, reduce valuation, or cause a deal to fall apart during due diligence. By highlighting common pitfalls, the episode prepares sellers to present a clearer and more credible financial story to potential buyers....

How to Structure a Sale for Valuation and Sellers Liquidity 12.02.2026

This podcast helps Canadian business owners understand how deal structure directly impacts both valuation and seller liquidity during a business sale. It explains why the way a transaction is paid for can be just as important as the headline purchase price, and how thoughtful structuring can protect financial outcomes while reducing unnecessary risk. The episode covers key components of sale struc...

Canadian Business Owners: Preparing for a Successful Exit 11.02.2026

This podcast is designed to help Canadian business owners prepare for a successful and well planned exit from their company. It focuses on the critical steps that can protect financial security, support long term goals, and reduce stress during one of the most important transitions an owner will ever face. Listeners will gain clarity on how early preparation can directly impact valuation, deal qua...

Business Owners: Why Start Planning Months Before Your Exit 10.02.2026

This podcast explains why business owners who start planning their exit months in advance consistently achieve stronger outcomes. It highlights how early preparation gives sellers more control over timing, value, and deal structure, while reducing surprises that can derail a transaction later in the process. Listeners will gain insight into how advance planning allows time to improve operations, c...

Financial Gaps to Address 24 Months Ahead of Selling a Business 05.02.2026

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 re...

Key Financial Levers That Increase Business Valuation 03.02.2026

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 p...

Common Issues Found in Due Diligence and What Sellers Should Fix 02.02.2026

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 insigh...

The One Thing to Increase Your Exit Valuation 30.01.2026

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 confidenc...

Why 80% of Canadian Business Owners May Never Sell 28.01.2026

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 d...

Empower Sellers: Maximize Value, Win Buyers with Key Tools 27.01.2026

 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 clarit...

Benefits of Association Membership When Selling a Business 22.01.2026

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 ac...

Sell Your Business to a Friend: Pros & Cons for Canadians 21.01.2026

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 cons...

Best Practices for Selling Your Canadian Business Safely 19.01.2026

 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,...

How Bankers Build a Buyer List for Your Canadian Business Sale 16.01.2026

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 busi...

How to Pick the Best Intermediary to Sell Your Business 15.01.2026

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. Listener...

Key Considerations for Business Owners Thinking of Selling 13.01.2026

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...

Be Prepared for Due Diligence When Selling Your Business 13.12.2025

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 con...

Going to Market 12.12.2025

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 fo...

Quality of Earnings (Q of E) Report – Building Trust 06.12.2025

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 highlight...

Setting Up the Virtual Data Room (VDR) 06.12.2025

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,...

Choosing the Right Sell-Side Strategy for Your Canadian Business 29.11.2025

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 epi...

Second Bite: A Lucrative Exit for Canadian Owners 28.11.2025

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...

Retired Entrepreneur Shares Lessons Selling A Family Business 21.11.2025

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 retirem...

Determining Your Business’s Value 20.11.2025

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 h...

Listen to the Selling Your Canadian Business: A Step-by-Step Guide to Maximizing Value and Securing Your Legacy podcast in Replaio

Radio and podcasts in one app - free, with no sign-up. Install today and do not miss the launch

Get it on Google Play

Replaio is not a podcast publisher; show names, artwork and audio belong to their authors and are distributed through public RSS feeds.