“If a society cannot find a way to deal with something that is actively melting it from within, then that is a terminal symptom.” — Finn Brunton
A couple of days ago, Donald Trump Jr.’s investment firm, 1789 Capital, led a billion-dollar funding round in Polymarket. As today’s guest, the fintech expert Finn Brunton, notes in an insightful Harper’s essay this month, prediction markets like Polymarket and Kalshi are transforming America into an always-on gambling den. No wonder, then, that the Trumps are such gleeful participants in what Brunton calls “the casinoification of modern life.” From the father’s Taj Mahal in Atlantic City to the son’s Taj on everyone’s phone. “Trade on Anything” as Kalshi promises (or threatens) us.
In “The Chaos Machine,” Brunton introduces us to two visionaries of prediction marketplaces. On the one hand, there’s the idealistic Robin Hanson, who dreamed of prediction markets as machines for truth with experts betting real money and generating trustworthy odds about the future. And then there’s Tim May, a self-described crypto-anarchist, the “bad guy,” according to Brunton, who invented the idea of BlackNet as an anonymous marketplace designed to destroy institutional trust from within. Brunton warns that today’s prediction marketplaces have bet on May, rather than Hanson. They are insider-trading machines where the smart money is always on the other side of the table.
It’s no wonder that Donald Trump Jr.’s investment firm is called 1789 Capital. By investing in prediction marketplaces, they are accelerating an anarchic French rather than institutionally trustworthy American-style revolution. These BlackNet operations are both the cause and effect of today’s destruction of trust. Polymarket is the polycrisis. It is cashing in on chaos.
Five Takeaways
• From Papal Bets to Polymarket. Robin Hanson’s big idea: make experts bet real money and get honest odds about the future. A fundamentally positive idea — a machine for consensus.
• The Casinoification of Modern Life. Polymarket flipped Hanson: “monetize any difference in opinion.” The result: rip-off machines where whales with inside knowledge exploit suckers — while the platforms play for time against regulation.
• Tim May’s BlackNet. The “bad guy” of the story dreamed of an anonymous market for secrets designed to destroy institutional trust from within. Prediction markets claim Hanson’s vision; they fulfill May’s.
• Polymarket & the Polycrisis. Worse than casinos — nobody checks the wheel. And for a generation with no faith in pensions or the dollar, betting on chaos is “a weirdly rational decision.” Lambos or food stamps.
• Betting on Hanson Over May. The fix is concrete: know-your-customer rules would “eliminate 95% of the bad actors” overnight. Brunton still bets on Hanson. Kant over Hobbes.
About Keen On America
Nobody asks more awkward questions than the Anglo-American writer and filmmaker Andrew Keen.
Website: https://keenon.tv/ Substack: https://keenon.substack.com/ YouTube: https://youtube.com/@KeenOnShow
Read The Chaos Machine: harpers.org
Chapters:
00:00:31 Introduction: Trump Jr. buys into Polymarket
00:02:11 Prediction markets 101: from papal bets to Polymarket
00:03:34 Robin Hanson, the hedgehog with one big idea
00:06:05 Beyond the wisdom of crowds: markets for experts
00:09:16 “Monetize any difference in opinion”
00:12:37 The casinoification of modern life
00:14:28 Insider trading: the colossal oversight
00:15:42 The funnel: whales, suckers, and the house
00:16:56 Playing for time against regulation
00:19:02 Enter Tim May: the bad guy
00:22:48 BlackNet: a black market for secrets
00:24:20 Destroying institutional trust from within
00:27:07 Hanson’s vision, May’s fulfillment
00:28:31 Teleprompter bets and soldiers’ wagers
00:29:12 Worse than casinos: nobody checks the wheel
00:31:24 Polymarket and the polycrisis
00:34:16 Why the young gamble: a weirdly rational despair
00:37:08 The smart money is on the other side of the table
00:40:24 The heir to crypto: untraceable corruption
00:42:29 A terminal symptom?
00:46:48 The magic bullet: KYC
00:49:00 Betting on Hanson over May