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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

10:58

Setting Emotional and Financial Goals for the Sale

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

2025/11/19

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. ...

en-ca

14:31

Enhancing Business Value Before the Sale

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

2025/11/14

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...

en-ca

14:05

Conducting a Pre-Sale Business Audit

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

2025/11/13

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...

en-ca

17:49

Assembling Your Advisory Team

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

2025/11/12

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...

en-ca

14:54

Key Valuation Terms for Canadian Business Owners

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

2025/11/07

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...

en-ca

11:24

2025 Valuation Tips for Canadian Owners

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

2025/11/06

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 ...

en-ca

13:11

Lower-Middle-Market M&A Deal Closes Daily in Canada

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

2025/11/05

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...

en-ca

14:19

Exiting a Technology Business: A Strategic Guide

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

2025/10/31

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...

en-ca

15:16

Why Canadian Business Owners Need a 36-Month Rolling...

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

2025/10/30

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...

en-ca

12:11

The Great Canadian Business Handover: Next Gen Steps Up!

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

2025/10/24

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 ...

en-ca

15:55

How M&A Advisors Craft Target Lists for Canadian...

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

2025/10/23

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...

en-ca

14:27

Navigating the Sell-Side Process

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

2025/10/16

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,...

en-ca

33:51

Maximize Your $10–$50M Sale With Expert M&A Leverage

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

2025/10/15

Selling a $10–$50 million business is often a once-in-a-lifetime opportunity to realize the full value of years of hard work. This podcast explores how Canadian lower-middle market business owners can leverage expert M&A guidance to turn unsolicited approaches from stakeholders, like competitors, suppliers, or management teams, into competitive auctions that drive maximum value. You’ll learn how the right strategy can transform a single offer into multiple bids, creating leverage that tra...

en-ca

38:36

Avoid M&A Pitfalls: Secure Your Business Sale in Canada

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

2025/10/09

Navigating the Sell-Side M&A Process: Key Risks and Delays After an Executed LOI for Canadian Business Owners Closing a business sale does not end with signing the Letter of Intent. It is often where the real challenges begin. In this episode, we explore what happens after the LOI is executed and why this stage can be the most unpredictable part of the M&A journey. For Canadian business owners, the time between signing the LOI and receiving final payment can bring deal fatigue, renego...

en-ca

25:56

Navigating a Pre-Emptive Offer

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

2025/10/08

Selling a business is one of the most significant decisions an owner can make, and when a pre-emptive offer appears early in a broad auction process, it can feel like both an opportunity and a test of strategy. In this episode, we break down what a pre-emptive offer really means, how it can affect your auction process, and what Canadian business owners should consider before saying yes. We explain how broad auctions work, why pre-emptive offers arise, and what they reveal about buyer motivati...

en-ca

33:56

Early M&A Offer: Bully or Bargain? What to Do Next

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

2025/10/07

In this episode, we delve into the high-stakes world of mergers and acquisitions, where timing and strategy can determine millions. Picture this: you are ready to sell your company when a buyer suddenly offers $22 million with only 72 hours to respond. It looks tempting, but could this early bid derail your entire auction? We break down the difference between a bully offer and a pre-emptive offer, how to spot the signs, and what each means for your sale strategy. Learn how to respond under pr...

en-ca

13:51

De Minimis Exemption Suspension Creates Acquisition...

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

2025/09/25

The U.S. government's suspension of its de minimis exemption on Aug. 29, 2025, is altering trade dynamics across North America and presenting strategic advantages for Canadian companies in the $5 million to $50 million annual revenue segment. Under Executive Order 14324, imports valued under $800 no longer receive duty-free entry or expedited customs processing. While this adds costs to low-value shipments from Canada, it enhances the competitiveness of Canadian exports under the U.S.-Mexico-...

en-ca

4:48

Marketed Sale vs. Direct Acquisition: How You Can...

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

2025/09/25

Marketed Sale vs Direct Acquisition: How Canadian Businesses Can Maximize Value When Canadian business owners decide to sell, a pivotal decision involves choosing between a broadly marketed sale and a direct acquisition. The chosen approach can significantly impact the final valuation, experts say.

en-ca

14:26

Acquire to Accelerate: Fast Growth for Startups

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

2025/09/25

Canadian entrepreneurs with startups pulling in $5 million to $50 million in annual revenue face a familiar crossroads: grind out organic expansion or snap up a rival for quicker wins? The choice matters more than ever in a market where speed trumps patience. Companies pursuing acquisitions boast short-term revenue growth rates 8.3 percentage points higher than those sticking to internal efforts. For mid-sized firms like yours, buying growth isn't just flashy, it's a shortcut to new pro...

en-ca

21:54

10 Most Negotiated Elements in a Share Sale

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

2025/09/18

As a Canadian business owner with a company generating between $5 million and $50 million in annual revenue, deciding to sell your privately held enterprise is a big step. In this mid-market segment, share sales are common. They let buyers acquire the entire entity — including assets, liabilities and tax attributes — while often giving you favorable tax treatment, such as access to the lifetime capital gains exemption. But the share purchase agreement that governs the deal is complex. As an M...

en-ca

60 results

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