Contrarian Investing: Seeking Uncorrelated Outcomes in Venture Capital

This title was summarized by AI from the post below.

If you're "playing the game on the field" you are doing what everyone else is doing. Which, in venture capital, an asset class designed to seek uncorrelated outcomes, is a curious study in contrarian investing. I write about the concept of alpha as it relates to markets and why building a 50 year business might be the best way to generate outsized asymmetric returns. And why, even knowing that, it's still so hard as humans to go against the herd. Thanks to Peter Walker for some great research that contributed to this article. Read here: https://lnkd.in/e75Dbipi

Alpha lives in convexity. The biggest problem in venture is the measurement system. We underwrite and measure non-linear assets with linear tools. Rollup to the fund level and again using linear tools to measure non-linear returns. A power law is convexity or an assymetrical non-linear payoff which is geometric. Until venture updates its measurement system to underwrite geometrically in day 1 consensus will dominate after convexity is already priced in which destroys alpha. This is just getting exposed now since we’re in a geometric risk regime where duration can compound downside. The 40 year declining rate regime from 1981 - 2021 hid the math misalignment for alpha as capital always got cheaper with time.

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Yep - Alpha is the antithesis of what the vast majority of investors are looking for. They want the "you'd have to duck to miss" playbook... Agreed that the slow burn is a way to go, but equally think there is merit in not targeting a billion (trillion?) dollar business as the ultimate goal. Geopolitical polarisation is going to have a role to play - and if the US is no longer de rigeur in terms of expansion, and if massive investment in sovereign tech to better insulate against reliance on US platforms continues to accelerate as a strategic imperative - maybe the "not trillion dollar" business writes itself :-) Great article - as ever, enjoyed the read.

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Saw the same thing play out in engineering bets. Every company I worked at chased the same tech stack trends at the same time. The teams that built durable platforms were the ones willing to look "behind" for a few years. Going against the herd is hard because the herd also controls your performance reviews.

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Love the framing: venture is supposed to chase uncorrelated outcomes, yet most people still “play the same game on the field.” Herd behavior is the silent tax on alpha.

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Yes, the Alpha was so hard to do. The hard part is not just going against the herd, but knowing when to hold your conviction (for a long long time) vs when you’re just stubbornly wrong. Differentiating the two is where real alpha is born.

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Everyone says they want alpha. Very few are willing to look wrong for a decade to get it.

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I have come to truly appreciate your articulation of emerging, and often debated, topics. Thanks for this framing.

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Sam there is something special about your take on the market, business, and the state of this sphere (VC, over-raising, over consumption and production). It's is hard to pin-point, but so needed right now. Thank you - this is a great article.

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If everyone is playing the same game, you’re competing on execution

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