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Selling Your Canadian Business: A Step-by-Step Guide to Maximizing Value and Securing Your Legacy
The Shaughnessy Group
48 episodes
3 weeks ago
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...
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Entrepreneurship
Business,
Investing
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All content for Selling Your Canadian Business: A Step-by-Step Guide to Maximizing Value and Securing Your Legacy is the property of The Shaughnessy Group and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.
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...
Show more...
Entrepreneurship
Business,
Investing
Episodes (20/48)
Selling Your Canadian Business: A Step-by-Step Guide to Maximizing Value and Securing Your Legacy
Be Prepared for Due Diligence When Selling Your Business
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...
Show more...
1 month ago
14 minutes

Selling Your Canadian Business: A Step-by-Step Guide to Maximizing Value and Securing Your Legacy
Going to Market
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...
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1 month ago
12 minutes

Selling Your Canadian Business: A Step-by-Step Guide to Maximizing Value and Securing Your Legacy
Quality of Earnings (Q of E) Report – Building Trust
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...
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1 month ago
13 minutes

Selling Your Canadian Business: A Step-by-Step Guide to Maximizing Value and Securing Your Legacy
Setting Up the Virtual Data Room (VDR)
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...
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1 month ago
10 minutes

Selling Your Canadian Business: A Step-by-Step Guide to Maximizing Value and Securing Your Legacy
Choosing the Right Sell-Side Strategy for Your Canadian Business
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...
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1 month ago
16 minutes

Selling Your Canadian Business: A Step-by-Step Guide to Maximizing Value and Securing Your Legacy
Second Bite: A Lucrative Exit for Canadian Owners
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...
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1 month ago
15 minutes

Selling Your Canadian Business: A Step-by-Step Guide to Maximizing Value and Securing Your Legacy
Retired Entrepreneur Shares Lessons Selling A Family Business
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...
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1 month ago
11 minutes

Selling Your Canadian Business: A Step-by-Step Guide to Maximizing Value and Securing Your Legacy
Determining Your Business’s Value
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 ...
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1 month ago
14 minutes

Selling Your Canadian Business: A Step-by-Step Guide to Maximizing Value and Securing Your Legacy
Setting Emotional and Financial Goals for the Sale
This podcast explores how owners of mid market Canadian businesses can set clear emotional and financial goals before selling. You will learn how to prepare for the personal transition that comes with letting go of a company, including identity changes, family dynamics, legacy concerns, and the unique challenges faced by family owned, digital, and cross border businesses. Each episode helps you understand what emotional readiness looks like and how to shape your next chapter with confidence. ...
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1 month ago
10 minutes

Selling Your Canadian Business: A Step-by-Step Guide to Maximizing Value and Securing Your Legacy
Enhancing Business Value Before the Sale
In this episode, we dive into how mid-market Canadian businesses can significantly enhance their value before a sale. Whether your company generates between $5M and $50M in annual revenue, the strategies shared here will help you attract top-tier buyers and command a stronger valuation. From improving revenue diversity to optimizing EBITDA margins and integrating ESG practices, this episode outlines what truly drives buyer interest and higher offers. You’ll hear actionable insights tailored t...
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2 months ago
14 minutes

Selling Your Canadian Business: A Step-by-Step Guide to Maximizing Value and Securing Your Legacy
Conducting a Pre-Sale Business Audit
A pre-sale business audit is one of the most critical steps before selling a mid-market business. This podcast unpacks how a comprehensive audit can uncover hidden risks, enhance buyer confidence, and maximize your company’s valuation. From financial readiness and operational efficiency to legal compliance and ESG standards, you’ll learn how to prepare your business for buyer scrutiny and stand out in competitive markets. We explore real-world examples of Canadian mid-market firms across SaaS...
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2 months ago
14 minutes

Selling Your Canadian Business: A Step-by-Step Guide to Maximizing Value and Securing Your Legacy
Assembling Your Advisory Team
Building the right advisory team is the foundation of a successful mid-market business sale. In this episode, you’ll learn how to assemble experts who bring deep experience in M&A, legal, tax, and financial strategy, each playing a key role in navigating the complex process of selling a $5M–$50M Canadian business. Whether your goal is to maximize valuation, reduce risk, or manage cross-border transactions, this discussion breaks down exactly which kind of advisors you need and why their e...
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2 months ago
17 minutes

Selling Your Canadian Business: A Step-by-Step Guide to Maximizing Value and Securing Your Legacy
Key Valuation Terms for Canadian Business Owners
Understanding business valuation is essential for Canadian entrepreneurs preparing to buy or sell a company. This podcast unpacks the key terms enterprise value, equity value, and selling price, so you can make confident, informed decisions. Listeners will gain clarity on how these valuation metrics shape negotiations, influence deal structures, and ultimately impact the financial outcome of a business transaction in Canada’s dynamic market. Through real-world examples and practical explanati...
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2 months ago
14 minutes

Selling Your Canadian Business: A Step-by-Step Guide to Maximizing Value and Securing Your Legacy
2025 Valuation Tips for Canadian Owners
In this episode, we explore the key valuation trends shaping the Canadian private business landscape in 2025. Whether you’re preparing to sell, seeking investors, or simply assessing your company’s worth, understanding how market conditions, profit margins, and deal structures are evolving can give you a strategic edge. You’ll learn what factors are driving recovery in valuation multiples and why timing and performance matter more than ever for achieving strong results. We also dive into how ...
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2 months ago
11 minutes

Selling Your Canadian Business: A Step-by-Step Guide to Maximizing Value and Securing Your Legacy
Lower-Middle-Market M&A Deal Closes Daily in Canada
Canada’s lower-middle-market M&A scene is more active than ever, with a transaction closing nearly every day across the country. This podcast explores how that pace of activity, driven by companies earning $10 million to $50 million in revenue, reflects a healthy, resilient market. Listeners will gain a clear understanding of what’s fueling this growth, from steady deal flow and strong valuations to global investor interest, and why it matters for Canadian business owners. Each episode di...
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2 months ago
13 minutes

Selling Your Canadian Business: A Step-by-Step Guide to Maximizing Value and Securing Your Legacy
Exiting a Technology Business: A Strategic Guide
Exiting a technology business is one of the most pivotal moments in an entrepreneur’s journey. This podcast explores how Canadian tech founders can navigate the complexities of selling, merging, or transitioning their companies while preserving value and vision. Through practical strategies and real-world examples, listeners will gain a clear understanding of exit options — from strategic and financial buyers to IPOs and management buyouts — and learn how to align their exit plan with their l...
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2 months ago
14 minutes

Selling Your Canadian Business: A Step-by-Step Guide to Maximizing Value and Securing Your Legacy
Why Canadian Business Owners Need a 36-Month Rolling Forecast
This episode explores why every Canadian business owner preparing for a sale needs to adopt a 36-month rolling forecast to maximize business value. Listeners will learn how forward-looking financials play a crucial role in shaping buyer confidence and driving premium valuations. By understanding how projected EBITDA and forward multiples influence modern dealmaking, owners can better position their companies for successful exits. We break down the advantages of maintaining a continuous 36-mon...
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2 months ago
15 minutes

Selling Your Canadian Business: A Step-by-Step Guide to Maximizing Value and Securing Your Legacy
The Great Canadian Business Handover: Next Gen Steps Up!
Canada’s business world is in the midst of a massive transformation as Baby Boomers pass the entrepreneurial torch to Generation X and Millennials. This podcast explores the dynamics behind this historic handover, revealing how tens of thousands of companies and billions in wealth are shifting hands. Listeners will discover the real impact this transition is having on local economies, industries, and innovation across the country. Each episode dives deep into the data and stories behind this ...
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2 months ago
12 minutes

Selling Your Canadian Business: A Step-by-Step Guide to Maximizing Value and Securing Your Legacy
How M&A Advisors Craft Target Lists for Canadian Business Sales
When selling a Canadian business valued between $10M and $50M, building the right target list of potential buyers can define the success of the entire process. This podcast breaks down how investment bankers and M&A advisors craft these strategic lists for lower-middle-market business owners. You’ll learn how professionals identify qualified buyers, align outreach with your goals, and ensure confidentiality while maximizing competition to drive higher valuations. Listeners will gain insig...
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2 months ago
15 minutes

Selling Your Canadian Business: A Step-by-Step Guide to Maximizing Value and Securing Your Legacy
Navigating the Sell-Side Process
Selling a business is one of the most important transitions an entrepreneur can experience. This podcast explores how Canadian business owners can navigate the sell-side process with confidence, clarity and strategy. Listeners will gain a deep understanding of what it takes to prepare their company for sale, maximize value and preserve their legacy through every stage — from preparation and valuation to negotiation and closing. Each episode dives into the realities of today’s Canadian market,...
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2 months ago
14 minutes

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