Andrea Matheson: $175M ARR in 24 Months, $1B in Value Across Three Exits

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Getting to the Deal

Exit Horizon

7 episodes

8 hours ago

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.

Entrepreneurship

Business

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Entrepreneurship

Business

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Andrea Matheson: $175M ARR in 24 Months, $1B in Value Across Three Exits

Getting to the Deal

37 minutes 28 seconds

2 months ago

Andrea Matheson: $175M ARR in 24 Months, $1B in Value Across Three Exits

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.