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.
