Entrepreneurship Through Acquisition with Marc Deegan

Buying and Selling Canadian Small Businesses

In episode, Keith Matthews welcomes Marc Deegan, founder of R33 Ventures and an expert in business valuations and M&A for small to medium-sized enterprises (SMEs). Together, they explore the rapidly growing model of entrepreneurship through acquisition, cover current trends in the Canadian SME marketplace, common challenges, and best practices.

Expert Marc Deegan offers a clear, actionable conversation on the realities of buying and selling SMEs in Canada. Learn how to define the right buyer profile, discover what truly drives business valuations, and get the inside track on how sellers can prepare for a smooth and rewarding transition. You’ll walk away knowing what steps to take whether you’re seeking your next entrepreneurial journey or ready to unlock the full value of the business you’ve built.

This episode is a must for business owners contemplating a sale, aspiring entrepreneurs considering acquisition, and professionals advising clients through these pivotal transitions. Avoid costly mistakes, get practical strategies for vetting buyers and sellers, and understand how to best protect your financial interests. Tune in for expert insights and feel confident moving forward in today’s dynamic M&A landscape.

Business Ownership and Wealth Planning

• What is “entrepreneurship through acquisition” and why is it gaining traction? (00:04:06)
• Defining SMEs in Canada – revenue range and market overview (00:06:27)
• The coming “succession tsunami” and key stats from CFIB (00:06:00)
• The #1 obstacles to succession: finding buyers & agreeing on value (00:07:24)
• Who’s buying small businesses? Buyer profiles, backgrounds, and motivations (00:08:43)
• Where and how buyers find private companies for sale (00:10:16)
• The gender gap in entrepreneurship and industry trends (00:11:48)
• Balancing dual-income households and risk-taking in business ownership (00:12:44)
• Stages of the buying process: NDAs, financials, and due diligence (00:13:46)
• How business valuation works – multiples & EBITDA (00:17:04)
• Shifts in market valuations, impacts of tariffs, and timing of transactions (00:18:11)
• The time and effort required to buy a business in Canada (00:20:01)
• Profiles of sellers – why and when business owners exit (00:21:48)
• Tax planning and the capital gains exemption for sellers (00:23:35)
• The dangers of client concentration and business dependence (00:25:10)
• Realistic timeline for selling: preparation, transaction, and transition periods (00:29:27)
• Who are the buyers? Competitors, management, private equity, and family (00:31:00)
• How funding works: equity, bank loans, and seller financing (00:37:08)
• Building your professional deal team – advisors, accountants, bankers, and lawyers (00:39:10)
• Top advice for buyers: focus, persistence, and differentiating yourself (00:40:20)
• Top advice for sellers: know your numbers, set clear exit goals, and plan intentionally (00:42:01)

Mentioned in this Episode:

• R33 Ventures 
• Marc Deegan on LinkedIn
• Podcast Human Capital: 5 Guiding Career Principles with Mark Halloran
• Stanford Business Search Fund Study
• Succession Tsunami: Preparing for a decade of small business transitions in Canada