I grew up in Toronto, went to Upper Canada College and then studied at the Richard Ivey School of Business, earning an HBA from Western University. Somewhere in the middle of it, a semester at sea took me to fifteen countries in six months, the start of a travel habit I’ve never shaken.

The lesson that stuck: markets are rarely rational, people rarely behave as expected, and the best opportunities exist in the gap between theory and reality.

My career began in strategy consulting at KPMG, advising executives at Fortune 500 companies on growth and operations.

It taught me the question that has guided every role since: not whether something is clever, but whether someone will pay for it.

At O’Leary Ventures, I evaluated early-stage companies, led diligence on Shark Tank investments, and spearheaded the licensing deal that created O’Leary Fine Wines. Most celebrity products lean on the name and not much else. Kevin actually knew wine, and it went on to sell more than 2 million cases across North America.

I joined FreshBooks before the Series A, in a product role, and spent three years building core business lines as the company scaled toward a $100M revenue run rate. Then the curve flattened, and the question shifted from what to build next to how to keep growing.

So I moved out of product to build the corporate development function, and led two eight-figure acquisitions, FastBill in Germany and Facturama in Mexico, that reignited annual growth past 25%. At a certain scale, the fastest path forward is acquired rather than built.

As a Venture Partner at AGE Fund, a $50M fintech and blockchain fund, I led three investments, including Union and MintStars. I also worked with SuperRare from white paper to launch and helped EQTY Lab bootstrap its AI Integrity Suite.

Most of venture is momentum dressed as conviction. Coming off the operating side, I kept asking the harder question: who is actually building something people will use and pay for.