The Timeless Investor Show

Conviction Without Certainty: How Great Investors Move in Uncertain Times


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What’s the difference between conviction and certainty?

In this episode, Arie van Gemeren — fund manager, real estate investor, and author of Timeless Wealth — unpacks one of the most overlooked distinctions in investing and decision-making.

Certainty can blind you. It locks you into narratives, filters out risk, and creates fragility.

But conviction? Conviction is different. It’s not about being right — it’s about building a process you trust, having the courage to act, and the humility to adapt when the facts change.

Drawing on insights from Daniel Kahneman, Nassim Taleb, and Philip Tetlock — plus real-world investing stories from the 2020–2023 real estate cycle — Arie explores why the most successful investors aren’t the ones who are sure, but the ones who are prepared.

If you’re an operator, LP, capital allocator, or just someone trying to make smarter decisions under uncertainty — this is the episode for you.

Articles referenced in this podcast:

The Overconfidence Bias 

Alpha & Beta In Real Estate Investing

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The Timeless Investor ShowBy Arie van Gemeren