In this episode, I sit down with Andrew Brown to unpack the real mechanics of investing – from the ideas that shape conviction to the mistakes that refine it.
We start with reflections on 2025 and the lessons that most influenced Andrew’s thinking as an investor. From there, we dive deep into Constellation Software and the broader software selloff: why CSU stood out, how AI disruption changes the thesis, and what could ultimately prove the investment wrong.
We also explore the psychology of near-misses through the lens of Wise.
Beyond public markets, Andrew shares candid insights from his experience as a business operator – what surprised him, what proved harder than expected, and how running a company reshaped his approach to investing.
We close with a passion pick from his portfolio and a discussion on what makes a business intellectually compelling, misunderstood, and fragile at the same time.
A conversation about conviction, humility, and the messy reality behind great investment decisions.
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