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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

16:17

Why Professional Service Firms Acquire Rivals

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

2025/09/18

More Than Just The Bottom Line: Why Professional Service Firms Acquire Rivals In the competitive landscape of professional services – from law firms and accounting practices to consulting agencies and architectural studios – the decision to acquire a rival isn't just about snatching up market share. While the core business principles of reducing competition and boosting the bottom line certainly apply, these strategic moves are deeply nuanced by the very nature of what professional firms sell...

en-ca

18:32

Skyrocketing Your $10–$50M Sale With Porter’s Five...

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

2025/09/10

For Canadian business owners of privately owned companies with $10 to $50 million in annual revenue, selling your lower-middle market business is a high-stakes opportunity. Often, an unsolicited approach from a stakeholder—such as a rival, supplier, customer, or management team member—triggers the sale process. By integrating Porter’s Five Forces analysis, a skilled M&A advisor can leverage competitive dynamics to create an auction that maximizes value. Advisors typically add 1.25x EBITDA...

en-ca

18:32

Master Working Capital in Your $10–50M Business Sale

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

2025/09/10

As a Canadian business owner preparing to sell your $10 to $50 million revenue company through a broadly marketed M&A process led by an M&A advisor, you’re likely navigating a complex but exciting transition. One critical concept that will arise during negotiations, particularly in the Letter of Intent (LOI) from a buyer, is working capital—and specifically, the requirement to leave a certain amount of working capital in the business as part of a share sale on a debt-free, cash-free b...

en-ca

16:29

How Much Capital Is Available to Buy Your Canadian...

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

2025/09/03

As a Canadian business owner running a lower middle market company—typically generating $5–$100 million in annual revenue or $2–$20 million in EBITDA—you may be wondering about the pool of capital available from private equity (PE) firms and strategic acquirers looking to buy businesses like yours in 2025. The good news? There’s a substantial amount of money out there, and your business could be an attractive target. Here’s a breakdown of the capital landscape and what it means for you.

en-ca

16:55

Don't Get Caught Off Guard: Auction Your Business for...

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

2025/09/03

As a Canadian business owner of a privately held company generating $5 million to $50 million in annual revenue, selling your business is a high-stakes endeavor that can define your financial legacy. Businesses in this lower middle market segment typically exhibit earnings before interest, taxes, depreciation and amortization ranging from approximately $1 million to $10 million, depending on industry margins (often 10-20% of revenue) and operational efficiency. In this space, surprises lurk a...

en-ca

14:57

MBO: Spotting Top Talent for Your Company's Succession

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

2025/09/03

A management buyout (MBO) is a strategic transaction where a company’s management team purchases all or part of the business, often with external financing. This approach allows managers to take control of a company they know intimately, leveraging their expertise to drive future success. Below, we explore the key aspects of an MBO, its benefits, challenges, and steps to execute one effectively, including the critical role of hiring an M&A advisor.

en-ca

16:48

Share Purchase Agreement Strategic Considerations

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

2025/08/29

In a Canadian business share sale, the Share Purchase Agreement (SPA) is the cornerstone document that formalizes the transfer of shares from the seller to the buyer, detailing critical terms such as purchase price, representations and warranties, indemnities, conditions precedent, and post-closing obligations. The Letter of Intent (LOI), typically non-binding except for provisions like confidentiality or exclusivity, precedes the SPA and outlines key deal terms, serving as a framework for ne...

en-ca

23:17

Defining Your “Why Sell?” Statement

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

2025/08/22

The first step in selling your mid-market Canadian business ($5M–$50M in annual revenue) is defining your “Why Sell?” statement—a clear articulation of your motivations and goals for the sale. This foundational step ensures your decision aligns with your personal, financial, and emotional objectives, setting the tone for the entire process. For mid-market owners, selling often involves complex considerations, such as transitioning professional management teams, addressing family dynamics in f...

en-ca

13:21

Respond to Cold Outreach From Potential Buyers

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

2025/08/21

For owners of privately-owned Canadian businesses generating $10 to $50 million in annual revenue, receiving an unsolicited call from a potential buyer can be both intriguing and disruptive. These cold outreach attempts—whether from private equity firms, strategic buyers, individual investors, other entrepreneurs, the company’s major customers, major suppliers, or major rivals—often prompt a direct response from business owners, even when they’re not actively looking to sell. While engaging w...

en-ca

11:17

When To Skip A Quality Of Earnings Report

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

2025/08/21

For Canadian business owners navigating the sale or purchase of a company, a Quality of Earnings (QoE) report can be a powerful tool. This detailed financial analysis examines the sustainability and quality of a company’s earnings, often playing a key role in mergers, acquisitions, or investment decisions. However, producing or requiring a QoE report isn’t always necessary or prudent. Here’s a guide for Canadian business owners on when to forego this step.

en-ca

8:42

Are you Ready for Due Diligence?

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

2025/08/20

Self-Assessment: Are You Ready for Due Diligence? Business owners preparing to sell their company can use this self-assessment, based on the article “Common Issues Found in Due Diligence and What Sellers Should Fix,” to gauge readiness. It features questions linked to key issues from the article, helping owners pinpoint areas for improvement. Answer each question with “Yes,” “No,” or “Not Sure,” and follow the action steps to address weaknesses.

en-ca

12:24

Evaluating a Letter of Intent for Your Business

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

2025/08/19

Receiving unsolicited interest in buying your company can be both thrilling and overwhelming. The prospect of a sale brings a mix of emotions—pride in what you’ve built, curiosity about the buyer, and uncertainty about whether the offer truly reflects your business’s value. After engaging in discussions, meeting with the interested party, sharing financial information, and receiving a formal Letter of Intent (LOI), the critical question is: *Is the LOI a fair bid for your business?* This arti...

en-ca

15:26

Key Factors Influencing Seller Responses in Canadian...

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

2025/08/15

Canadian buyers interested in acquiring lower middle-market companies—those generating between $5 million and $50 million in revenue—face unique hurdles when searching for suitable targets. Success often hinges on working with an experienced M&A advisor, who can clarify which factors drive measurable responses from potential sellers and shape a thriving deal pipeline.

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15:28

Growing Your Canadian Business Through Acquisitions

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

2025/08/11

For Canadian business owners aiming to scale their operations, acquisitions offer a powerful strategy to achieve rapid growth, expand market share, and enhance competitiveness. While organic growth—building your business incrementally through internal efforts like increasing sales or developing new products—has its place, acquisitions can deliver transformative results faster and more effectively. A key driver of this value is valuation arbitrage, where acquiring companies at their market mul...

en-ca

19:42

Understanding Equity Rolls for Canadian Business Owners,

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

2025/08/11

As a Canadian business owner preparing to sell your business, you may encounter the term "equity roll" during negotiations, particularly when dealing with private equity firms, strategic buyers, or other sophisticated investors. An equity roll, also known as a rollover or equity rollover, refers to a transaction structure where the seller retains a portion of their ownership in the business by "rolling over" some of their equity into the new ownership structure post-sale. This allows the sell...

en-ca

10:48

Navigating The Management Meeting Stage In The M&A...

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

2025/08/10

For Canadian business owners selling a company with annual revenues between $5 million and $50 million, reaching the management meeting stage in the mergers and acquisitions (M&A) process is a pivotal moment. This phase, typically occurring after initial offers or letters of intent (LOIs) have been received, is where potential buyers get an in-depth look at your business and its leadership team. Engaging an M&A advisor has brought you to this critical juncture, and understanding the i...

en-ca

7:50

COMPENSATING KEY PEOPLE WHEN SELLING YOUR CANADIAN...

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

2025/07/30

In the Canadian business landscape, a company backed by a robust leadership team is inherently more attractive to both financial buyers (like private equity firms) and strategic buyers (such as competitors or consolidators). These buyers value transferability, the ability of the business to thrive without heavy reliance on the original owner, which often translates to higher valuations and smoother transactions. However, the sale process introduces complexities around compensating and retaini...

en-ca

12:58

ABOUT THE SHAUGHNESSY GROUP

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

2025/07/28

Unlocking Your Companies Value While Honoring Your Legacy. Selling and buying expertise for privately owned Canadian businesses with revenue from $5 million to $50 million

en-ca

13:55

HOW BUYERS REACT WHEN YOUR BUSINESS BEATS OR MISSES...

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

2025/07/28

As a Canadian business owner preparing to sell a company with $5 million to $50 million in revenue, you've likely invested significant time in the merger and acquisition process. Your M&A advisors have crafted a compelling teaser and confidential information memorandum (CIM), highlighting historical financials, projections and trailing 12-month EBITDA. After receiving multiple expressions of interest (EOIs) from financial and strategic buyers, some even surpassing your valuation expectati...

en-ca

13:36

WHERE DO M&A ADVISORS ADD THE MOST VALUE?

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

2025/07/28

As a Canadian business owner running a company with revenues between $5 million and $50 million, you're likely at a crossroads. Maybe you're eyeing retirement, a pivot to new ventures, or simply capitalizing on your hard work. Selling a private business isn't straightforward. It's a complex process fraught with risks, from undervaluation to deal-killing negotiations. This is where hiring an M&A advisor shines. Empirical data shows advisors can boost your sale price by 1.25x EBITDA—transla...

en-ca

60 results

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