Avoiding Short-Volatility Risks and Left Tails

Rupert Mitchell is a capital markets veteran with 30 years of institutional experience across three continents who now runs Blind Squirrel Macro, combining mythology, storytelling, and contrarian thinking to help investors understand why narrative often matters more than numbers in macro investing.

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3:00 - Rupert discusses the British education philosophy: learning to learn rather than narrow vocational training, creating adaptable generalists who aren't limited by having "an amazing hammer where everything has to look like a nail"

6:00 - Bearings collapse story: Fresh graduate Rupert spent his entire £400 bonus on a briefcase (still uses it 30 years later) hours before the 250-year-old merchant bank collapsed overnight due to Nick Leeson's derivatives trades

11:00 - Key lesson from Bearings: "Things are never as bad as you fear or as good as you would hope" - the "we're so back, it's so over" cycle teaches moderation in expectations and avoiding extrapolation extremes

16:00 - The mythology connection: Rupert's father, a military history writer, taught him that "most people don't really have a sense of history beyond about five or 10 years" - understanding cyclical patterns creates edge

21:00 - Chinese EV revolution firsthand: Witnessing Mercedes lose luxury market dominance to BYD in China taught Rupert that establishment brands can fall faster than anyone expects when technology shifts

33:00 - The generalist advantage: "I'm never baffled or scared of a new product, topic, market or theme" - breadth beats depth when markets constantly evolve and surprises come from unexpected directions

45:00 - AI investment paradox: Despite machine learning being used in biotech for years, healthcare hasn't announced breakthrough cycles - this "monkey on my back" makes Rupert question AI hype narratives

54:00 - On success: "Success has to be being proud of what you've done, right? And that's not a number. Some of the most miserable people I know are wealthier than God"

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