Explore every episode of the podcast Getting to the Deal

In this episode of Getting to the Deal, host Krystyn Harrison sits down with Jacqueline Dinsmore, a multi-exit entrepreneur who went from Bay Street lawyer to three successful exits in under a decade. Jackie shares her deeply personal journey from leaving Blake's law firm to care for her mother during cancer treatment, to co-founding FlapJackKids - a family business that scaled to thousands of stores before its strategic exit in 2019, just months before COVID would have devastated their brick-and-mortar heavy model.

Jackie reveals the raw truth about building with aging parents as business partners, the emotional reality of the "success hangover" that follows a liquidity event, and why most entrepreneurs fail because they try to sell businesses without proper documentation, clean financials, or organized data rooms. She breaks down why buyers smell desperation, how relationships matter more than pitch decks, and shares her investment philosophy of backing "the jockey, not just the horse" - including why she'll pass on founders who ghost her emails.

From professional services to consumer products, Jackie unpacks the critical differences between exit structures, why running due diligence-ready from day one is non-negotiable, and her three-pillar framework for successful exits: build relationships over pitch decks, take care of yourself first, and run your business as if due diligence starts tomorrow.

If you're a founder wondering how to navigate the emotional complexity of family business partnerships, prepare systematically for multiple exit scenarios, and build the relationships that actually close deals, this conversation offers the battle-tested wisdom you've been missing.

Show Notes:

00:00 Introduction to Jackie Dinsmore

06:13 Building Flapjack Kids

12:19 Building Relationships for Success

18:17 Preparing for the Transition

26:35 Navigating Exits: Professional Services vs. Consumer Products

32:37 Investing in People: The Jockey vs. The Horse

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This episode is brought to you by Exit Horizon. Our mission is to help strategic Canadian founders build systematically toward fulfilling exits using proven methodology from entrepreneurs and advisors who've actually navigated successful deals. We compress the learning curve so you can build with the end in mind from day one, not piece together exit strategies when it's too late. Apply now to join our next cohort or book a quick call to learn more about what might be the right place to start for your business. Visit exithorizon.com.

In this episode of Getting to the Deal, co-hosts Krystyn and Matt Harrison pull back the curtain on their own entrepreneurial journey, sharing why they founded Exit Horizon and the painful lessons that led them there. Krystyn reveals the raw truth about her seven-figure deal that fell apart when she made the critical mistake of running her own exit process, while Matt draws from his M&A experience helping business owners who called "on a Monday needing to sell" due to health crises or partnership disputes.

Together, they break down the exit timeline math that most founders get wrong - why your 5-year exit plan actually gives you only 3 years to build value - and share how they're building their current company with a buyer's perspective from day one. They discuss why most consulting businesses aren't sellable, the emotional reality of unwinding your identity from your company, and why the biggest mindset shift is understanding that "a business built to sell is built to last."

If you're a founder who wants to build systematically for exit, avoid the costly mistakes that derail deals, and create generational wealth on your terms, this deeply personal conversation offers the roadmap you've been missing.

In this episode of Getting to the Deal, host Krystyn Harrison sits down with Andrea Matheson, former M&A leader at CGI turned fintech founder, to unpack what it really takes to build with an exit in mind. Andrea shares her journey from overseeing $850M in acquisitions to co-founding Proponix, a company that scaled to $175M ARR in just 24 months before exiting. She reveals why the biggest mindset shift for entrepreneurs is to stop thinking like an owner and start thinking like a buyer, and how that changes every decision you make. Along the way, Andrea discusses the power of strategic partnerships, why planning twice before executing saves years of mistakes, and how true wealth is not about money but about time freedom.

If you are a founder wondering how to scale systematically, prepare for an exit, and design what comes next, this conversation is a masterclass you will not want to miss.

Show Notes:

00:00 The Journey to Entrepreneurship

02:58 Building Proponix: The Fintech Revolution

05:55 Strategic Partnerships and Exit Planning

08:57 Thinking Like a Buyer: A New Perspective

12:02 The Transition: From M&A Exec to Exited Founder

14:50 Wealth and Time Freedom: A New Reality

17:53 Lessons Learned: Resilience and Adaptation

20:51 Preparing for the Exit: The Importance of Planning

23:42 The Mindset Shift: From Owner to Buyer

26:36 Final Thoughts: Building for the Future

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This episode is brought to you by Exit Horizon. Our mission is to help strategic Canadian founders build systematically toward fulfilling exits using proven methodology from entrepreneurs and advisors who've actually navigated successful deals. We compress the learning curve so you can build with the end in mind from day one, not piece together exit strategies when it's too late. Apply now to join our next cohort or book a quick call to learn more about what might be the right place to start for your business. Visit exithorizon.com.

Real conversations with Canadian business owners who've sold their companies, the advisors who guided them, and the buyers who made it happen. Host Krystyn Harrison breaks down what actually worked, what didn't, and what you can apply to your own exit—whether you're planning to sell in two years or just want to understand your options. From deal structure to life after the sale, we cover the practical and personal side of turning your business into life-changing wealth.

Brought to you by Exit Horizon, the place where serious Canadian entrepreneurs go to discuss what most won't: how to build your business to sell, maximize your exit value, and design a fulfilling life after the deal.