Entrepreneurship through Acquisition: 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.

Key Topics:

1. What is “entrepreneurship through acquisition” and why is it gaining traction? (00:04:06)
2. Defining SMEs in Canada - revenue range and market overview (00:06:27)
3. The coming “succession tsunami” and key stats from CFIB (00:06:00)
4. The #1 obstacles to succession: finding buyers & agreeing on value (00:07:24)
5. Who’s buying small businesses? Buyer profiles, backgrounds, and motivations (00:08:43)
6. Where and how buyers find private companies for sale (00:10:16)
7. The gender gap in entrepreneurship and industry trends (00:11:48)
8. Balancing dual-income households and risk-taking in business ownership (00:12:44)
9. Stages of the buying process: NDAs, financials, and due diligence (00:13:46)
10. How business valuation works – multiples & EBITDA (00:17:04)
11. Shifts in market valuations, impacts of tariffs, and timing of transactions (00:18:11)
12. The time and effort required to buy a business in Canada (00:20:01)
13. Profiles of sellers - why and when business owners exit (00:21:48)
14. Tax planning and the capital gains exemption for sellers (00:23:35)
15. The dangers of client concentration and business dependence (00:25:10)
16. Realistic timeline for selling: preparation, transaction, and...

In this episode, Keith Matthews and Lawrence Greenberg reflect on an extraordinary investment year and what it means for disciplined investors heading into 2026. They break down how tariff-driven volatility, sharp drawdowns, and rapid recoveries defined 2025, yet ultimately rewarded those who stayed invested and globally diversified.

The conversation explores how Canada and international markets outperformed the U.S., how powerful market rotation reshaped returns, and why chasing forecasts or headlines would have been costly. Keith and Lawrence also address the growing debate around artificial intelligence, offering perspective drawn from past market cycles on how seasoned investors can benefit from innovation without speculation.

This episode is a must-listen for investors who have built meaningful wealth and want clarity after a strong multi-year run. If you’re focused on protecting gains, managing expectations, and staying disciplined through the next market cycle, this discussion reinforces why sticking to a long-term plan remains the smartest move.

Key topics:

● Setting the stage: why 2025 felt so uncomfortable despite strong returns (00:01:45)

● Tariffs, political uncertainty, and the sharp spring market sell-off (00:01:58)

● How markets rebounded rapidly, and why timing risk is so costly (00:03:55)

● The irony of 2025: regions targeted by U.S. tariffs delivered the strongest returns (00:03:14)

● Global asset class returns in Canadian dollar terms (00:04:24)

● Three years of exceptional equity performance and what that means for investors (00:05:00)

● The powerful rotation away from U.S. exceptionalism toward Canada and international markets (00:06:28)

● Why global diversification and factor exposure mattered more than predictions (00:07:22)

● Is AI a revolution or a bubble? Framing today’s debate with historical context (00:09:32)

● Parallels between AI enthusiasm and the dot-com era (00:10:48)

● Lessons from Cisco and Nortel: being right about technology vs. investment outcomes (00:12:55)

● How investors can benefit from AI without chasing individual winners (00:12:15)

● Why market forecasts consistently fail—and how bad predictions can hurt returns (00:15:48)

● Valuations, expected returns, and why future gains may be more muted (00:18:36)

● The “price of admission”: volatility, discipline, and long-term success (00:21:06)

● Final takeaways for 2026: stay invested, rebalance, and stick to your plan (00:20:46)

Thanks for Listening!

Be sure to subscribe on Apple, Google, Spotify, or wherever you get your podcasts. Feel free to drop us a line at lawrence@tma-invest.com or 514-695-0096 ext.112.

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Why Human Capital Is Your Most Important Investment:

In this episode, host Keith Matthews is joined by Mark Halloran, Co-Founder of Career Lion and expert in professional development, to explore how effective career management is key to optimizing your financial journey.

Special guest Mark Halloran breaks down a proven five-part framework for career management that applies to every stage, from early beginnings to executive leadership. This framework highlights the importance of continuous learning, tendering your career, managing up to accelerate growth, building a powerful network, and practicing gratitude to boost workplace fulfillment.

This episode is designed for employees, professionals and executives at every level who want to take control of their career trajectory, avoid common pitfalls, and maximize their career potential. Tune in for a roadmap to help you take charge of your next professional chapter and strengthen the most important investment you’ll ever make: your human capital.

Key Topics:

● Introducing Mark Halloran President & Co-Founder of Career Lion (0:00)

● Introducing the five guiding principles of effective career management (6:50)

● 1. Continual learning as the foundation for career confidence (7:25)

● How to identify and choose the right professional courses for your goals (9:40)

● Addressing deficiencies and strengths through targeted learning (11:26)

● Advice for early-stage professionals: get experience before pursuing more credentials (12:25)

● Pivoting careers and upskilling at later stages (14:15)

● How non-linear career paths often fuel greater long-term success (16:49)

● Avoiding the trap of “faking it till you make it”(11:26)

● 2. Tendering your career - why and how to objectively review your strengths and gaps (18:13)

● The SWOT approach for personal career assessment (20:55)

● Overcoming the Dunning-Kruger effect: humility in self-evaluation (23:44)

● 3. Managing up: how to proactively get feedback and earn opportunities (27:15)

● Giving and receiving actionable feedback, even when it stings (29:17)

● Continuous feedback and “stay interviews” vs. old-school annual reviews (33:00)

● 4. Networking for every age: building and maintaining authentic connections (34:15)

● How younger professionals can start purposeful networking(35:28)

● Networking tips for mid-to-late-stage professionals: leveraging existing contacts (43:49)

● The huge percentage of jobs won through networking (40:42)

● Using LinkedIn strategically: personal brand, outreach, & algorithm hacks (41:20)

● 5. Gratitude - why fulfilled, successful professionals cultivate thankfulness daily (50:01)

● Linking gratitude to resilience, growth, and workplace satisfaction (51:53)

● What Career Lion does and how professional coaching turbocharges results (55:43)

● Final takeaways: invest in yourself and manage your career like a business (1:01:59)

Mentioned in this Episode:

● Career Lion

Thanks for Listening!

Be sure to subscribe on Apple, Google, Spotify, or wherever you get your podcasts. Feel free to drop us a line at lawrence@tma-invest.com or 514-695-0096 ext.112.

Follow Tulett,Matthews & Associates on social media: LinkedIn, Facebook, and more!

Follow The Empowered Investor on Facebook,