In this episode of Getting to the Deal, host Krystyn Harrison sits down with Narbe Alexandrian, founder and CEO of Define Capital, a permanent capital firm that's rewriting private equity rules by acquiring vertical SaaS businesses to hold forever through a 40-year fund, not flip in 3-5 years. Before founding Define, Narbe served as president and CEO of RIV Capital, raising over $150 million and surviving three changes of control in just 16 months—experiences that shaped his radical philosophy: "We don't do deals on spreadsheets anymore. We do deals on trust. The price gets the headlines, the alignment builds the legacies." Narbe shares the pivotal conference encounter with a founder whose traditional PE buyer tripled prices, gutted R&D, and destroyed his earnout, crystallizing the question: what if private equity preserved legacies instead of extracting value? He reveals his strategic framework for evaluating companies (90%+ gross retention, diversified customer base, founder independence), why he walks away from businesses where founders do everything themselves, and his counterintuitive post-acquisition approach of spending 90-180 days observing with a magnifying glass before changing anything. The conversation explores why "building for the next 90 days destroys the next 10 years," the critical question he asks every lower mid-market founder ("if you have great economics and 25 years in business, why aren't you $30M?"), and his practical advice: take every inbound buyer call to get free consulting on what makes businesses valuable, then systematically prepare for founder independence. If you're a founder who's built something valuable but feels burned out, or you're worried about what happens to your team and customers after exit, this conversation reveals there's a different path—one where culture matters more than spreadsheets, relationships trump transactions, and your legacy can thrive for decades beyond your involvement.
Show Notes:
00:00 Redefining Private Equity: Building vs. Flipping
06:54 Narbe's Journey: From CPA to Private Equity Leader
15:05 The Evolution of Venture Capital and Market Dynamics
22:06 Understanding the Private Equity Landscape
29:46 The Importance of Culture in Business Transactions
36:59 Navigating Post-Acquisition Success
43:53 Advice for Founders: Preparing for Exit
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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, host Krystyn Harrison sits down with Marcus Mitchell, founder of Shire Capital Management and former CIO of Bonnefield, Canada's largest farmland manager. Marcus has overseen more than a billion dollars worth of farmland acquisitions and made the bold decision in 2021 to leave his institutional role to start his own firm focused on healthy food production. His first acquisition - British Columbia's largest organic blueberry farm - has tripled in value since purchase, demonstrating how values-driven investing can deliver both financial returns and societal impact.
This conversation reveals Marcus's three-pillar deal evaluation framework: premium product focus, geographical moats that prevent oversupply, and bulletproof operator partnerships. He explains how the buyer's mindset differs fundamentally from the VC approach founders typically encounter, why he prioritizes evidence over promises, and how he's evolving from real estate ownership to operating business acquisitions. If you're a founder planning your exit and want to understand how strategic buyers think, Marcus provides an insider's perspective on deal evaluation, relationship building, and value creation beyond the initial acquisition.
In this episode of Getting to the Deal, host Krystyn Harrison sits down with Tyler Handley, co-founder of Inkbox, who transformed a jungle discovery into a $65 million acquisition by BIC in seven years. Tyler shares how a personal frustration with temporary tattoos led him to Panama's jungles, where tribes using fruit-based dyes inspired the breakthrough technology behind semi-permanent tattoos. He reveals the strategic pivot that made Inkbox irresistible to acquirers - repositioning from a tattoo marketplace to a replenishable beauty accessory - and discusses his unconventional negotiation tactics, including using an "alter ego" to overcome Canadian politeness during deal discussions. Beyond the mechanics, Tyler opens up about the mental challenges of exiting, from the eight-month process of stress leaving his body to untethering personal identity from business success, explaining why 75% of founders regret their sale within a year. If you're a founder building a consumer brand or planning your exit strategy, this conversation provides tactical insights on positioning for acquisition, negotiating from strength, and preparing mentally for life after the deal.
Show Notes:
00:00 The Birth of Inkbox: A Unique Tattoo Journey
03:01 From Idea to Market: The Kickstarter Launch
06:06 Scaling Challenges and the COVID Boost
08:59 Navigating the Exit: The Acquisition by Bic
11:59 Life After the Exit: Transitioning to a New Reality
15:00 Finding Purpose Beyond Business
18:02 Advice for Future Founders: Balancing Work and Life
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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, 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 Flapjack Kids - 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.
