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If you are reading this on Substack, it is possible you still have enough dopamine receptors left to consume books and other long-form media.
For this reason, and because it’s a slow news week (just one coup so far), The Oracle is pleased to present this first annual Polymarket Gift Guide & Reading List.
The mission of The Oracle is to help you understand the world through the lens of prediction markets. Even if you never make a single trade, understanding probability and risk-reward is useful in many domains, and we’ve curated this list to help you do just that.
In case your funds are tied up in memecoins (🔮 49% chance Dogecoin hits 69¢ by inauguration day), the papers listed below are free to read online, and we link to the downloadable PDFs when available.
If you have other suggestions for Polymarket-native resources let us know in the comments.
Tools
Perplexity Pro ($200 / year) Perplexity is an AI search engine that’s a natural companion to Polymarket. It’s different from ChatGPT in that Perplexity has access to the latest news so its training data is never stale and it cites sources to avoid hallucination. It’s great for getting up to speed quickly on a new topic. For example, I once had Perplexity make - from a single query - a table of the top movies of 2024 along with their release dates, and box office sales. The Pro version gets you more credits and access to the latest AI models.
Kindle Scribe ($339) No more hassles trying to read PDFs on a paperback-size screen. This large format Kindle is the right size for reading full-page documents and has a touch screen that lets you make notes and highlights with a stylus (although syncing these notes to your computer is still wonky).
Crush Live Poker ($22.99 / month) Poker is the best way to get a gut “feel” for probabilities. After playing for a while, you develop a natural sense of the 1 in 3 odds of completing a flush by the river, or the 8.5% chance of hitting a gutshot straight on the next card. The best poker training is Bart Hanson’s Crush live Poker, which is a good blend between the game theory and the psychological (“exploitative”) approaches to the game. His free YouTube channel of poker hand-reviews is a good place to start if you already understand the core concepts.
Books
Superforecasting: The Art & Science of Prediction (Tetlock) The story of an ongoing academic project that puts people with no forecasting background into an online prediction tournament, with questions similar to those found on Polymarket. The book looks at habits and personality traits shared by the top performers (the “Superforecasters) who ended up beating the pants off academic experts and CIA analysts. If you read nothing else from the Polymarket canon, this is it.
Gambler: Secrets from a Life at Risk (Walters) A memoir by Billy Walters who founded The Computer Group, one of the most successful sports betting operations in history. This book gives a glimpse into the level of skill and resources that goes into beating the line in sportsbooks. In the pre-Internet era, Walters paid cleaners at the Las Vegas airport to collect sports pages left on arriving planes and scan them for injury reports, to cite just one example. There is a lot in here about Walters’ legal troubles and personal beefs, but the two chapters where he outlines his sports handicapping methods alone are enough to make this a must-read.
On the Edge: The Art of Risking Everything (Silver) Unlike (Polymarket advisor) Nate Silver’s first book which was a guide to probabilistic forecasting, his second book is an anthropology of professional risk takers, a group he calls “The River.” The book explores the differences among subgroups of The River, from poker pros to hedge fund traders, to crypto bros, and AI accelerationists, and understanding why they clash with “The Village,” which is Silver’s term for the index-fund loving, nanny state, New York Times establishment who are fundamentally trying to avoid risks, rather than take calculated ones. Listen to the audiobook if you can, which features Nate’s impressions of SBF, Steve Wynn, and other risk-loving celebs.
Articles
The Use of Knowledge in Society (Hayek, 1945) This Friedrich Hayek paper is the philosophical twinkle in the eye that led to the birth of modern prediction markets in the late 80s. Hayek was alarmed by the information theory problems of Soviet central planning, and argues in this paper that there is no way to aggregate the individual bits of information spread throughout society without a price signal (for example that Company A derives $10 of economic value from a lump of zinc while Company B derives $30 of value from it). Hayek is in awe of the hyper-efficiency of markets to aggregate these bits of information, which would be impossible in a top-down economy. While Hayek was most concerned with the types of information that would lead to resource distribution, it is easy to see how the argument could be extended for markets to sniff out other types of knowledge.
Shall We Vote on Values, But Bet on Beliefs? (Hanson, 2007) Robin Hanson is the intellectual father of modern prediction markets. Hanson is best known for this paper proposing “Futarchy,” a radical new form of government where prediction markets play a central role. Imagine a world where instead of voting for politicians who represent a vague set of vibes and policies, we voted on a general goal for society, like ‘maximize happiness’ or ‘maximize GDP.’ From there, prediction markets forecast which policies would get us to the goals, and, boom, we remove the need for corruptible politicians. The paper imagines a world where first this is fine tuned at the corporate level (think: conditional prediction markets on a company’s stock price if the CEO is replaced) before being rolled out to all of society. The central argument of The Oracle is that we should take prediction markets seriously for understanding what’s going on now and in the near future. This paper goes way further, sketching out how we might use them to order all of society.
Searching for Positive Returns at the Track (Bolton & Chapman, 1986) This statistics-heavy paper is a good companion to The Gambler, and is a must-read for anyone getting started in quantitative modeling of sports. Although the authors never bet using their strategy, this paper inspired many pro sports gambling operations, including a billion-dollar Hong Kong horse racing syndicate in the early 2000s covered in this Bloomberg piece.
Substacks
We are huge Substack bulls. In a world where social media is politically polarized and search engines are crushing small websites, Substack provides a censorship-free ecosystem where indie writers can find and monetize an audience.
We have begun recommending all these newsletters in our sidebar, and there is also a feature where you can gift a paid subscription. So we hope you will help support independent writing on the Internet.
Astral Codex Ten: The watering hole for the online rationalist community. Prediction markets are a frequent topic, along with AI, psychopharmacology, crime, and an annual prediction contest.
Silver Bulletin: Home of Nate Silver’s election model and political writing after he left corporate media. Check out his Harris Campaign post-mortem series.
Citrini Research: An investment researcher who uses broad-based themes eg. the rise of AI and weight loss drugs to pick baskets of stocks. Understand the technological forces shaping the economy.
The Intersection: Patrick Ruffini was the first pollster to identify what he calls the “multiracial populist coalition remaking the GOP.” His research on Substack is a must-read for understanding the geographic and demographic changes shaping the electorate.
New Right Poast: If you want to understand the memes, personalities, and obsessions driving the extremely-online new right but are too busy to scroll X all day, Dudley Newright has you covered. Start with his guest post “On Millennial Snot.”
Doomberg: A Substack on energy, finance, and geopolitics coverage by a green Cartoon chicken. A must for understanding the debate over renewables.
Defi Education: Bitcoin is over $100k and you still have no idea what crypto is? Start at the beginning and read everything.
Mark Halperin: Halperin’s reporting was 6-12 hours ahead of all other mainstream news during the Biden dropout saga. The best-sourced political reporter has now gone indy on Substack and a twice-daily YouTube show 2WAY.
Ettingermentum: Political analysis from the POV of the online left of Hasan Piker and Chapo Trap House.
Disclaimer
Nothing in The Oracle is financial, investment, legal or any other type of professional advice. Anything provided in any newsletter is for informational purposes only and is not meant to be an endorsement of any type of activity or any particular market or product. Terms of Service on polymarket.com prohibit US persons and persons from certain other jurisdictions from using Polymarket to trade, although data and information is viewable globally.