
SI361: The Four Faces of Trend Following ft. Richard Brennan
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Richard Brennan joins Niels for a conversation that redefines how trend following is understood. Behind the shared language lie four distinct archetypes - each built around a different purpose. Richard walks through them with clarity, then unpacks the trade-offs: static sizing vs. vol targeting, symmetry vs. asymmetry, speed vs. patience. A real-world portfolio test drives the point home... some strategies don’t just prefer diversification, they depend on it. This episode is about design, but more than that, it’s about alignment. Because in a field crowded with performance metrics, the most important question often goes unasked: what exactly is this built to do?
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50 YEARS OF TREND FOLLOWING BOOK AND BEHIND-THE-SCENES VIDEO FOR ACCREDITED INVESTORS - CLICK HERE
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Episode TimeStamps:
01:58 - ChatGPT5 is on fire
06:04 - The AI revolution could be the end of humanity
14:23 - Industry performance update
19:19 - An overview of what topics this episode will cover
21:23 - The decisions that really matter in trend following
27:10 - The 4 archetypes of trend following
34:05 - Its not about facts, its about objectives
40:09 - 1st debate: Diversification vs. concentration
48:52 - 2nd debate: Absolute momentum vs. cross-sectional momentum
50:21 - 3rd debate: Volatility targeting vs static small bits
54:02 - What trend followers sometimes get wrong about volatility and position sizing
57:48 - 4th debate: Symmetry vs asymmetry
01:02:00 -...