Show Notes
Prediction markets are a multi-billion dollar industry, led by companies like Kalshi and Polymarket. They are also controversial. Some want them banned and believe they are operating illegally, while others see them as invaluable truth-seeking markets. This podcast is a multi-hour deep dive on prediction markets, starting from conclave betting in 15th century Rome to the CFTC's proposed rulemaking on Rule 40.11 earlier this month. My goal: The internet's most comprehensive explainer on prediction markets. By the end of this episode, I promise you'll be in the top percentile for understanding prediction markets, regardless of where you're starting from. (You just might need to listen twice. There's a lot here.) Timestamps: 0:00 Intro 1:40 16th century papal betting (Koleman Strumpf) 11:13 Insider trading rules on prediction markets (Bobby DeNault) 16:20 The Google search insider case and Rule 180.1 (Sam Enzer) 27:38 Why prediction markets matter (Chris Giancarlo) 33:20 Election betting in America38:35 Iowa Electronic Markets and the 1992 no-action letter 45:56 Dodd-Frank, swaps and the Special Rule 48:08 Senator Lincoln on Super Bowl and Derby contracts 55:49 Parlays as swaps (Josh Sterling) 1:01:23 CFTC's exclusive jurisdiction (Thania Charmani) 1:07:30 Perspective on the CFTC's NPRM (Michael Passalacqua) 1:14:55 Exceptions that swallow the rule (Paul Grewal) 1:27:25 How prediction markets actually work 1:36:05 Kalshi's probability-weighted fee structure 1:38:18 Cardi B and the resolution problem (Dustin Gouker) 1:45:05 Oracles, UMA and decentralized resolution (Jeff Amico) 1:51:55 Inside the Ninth Circuit case 2:07:49 The CFTC's June 2026 proposed rulemaking (Brad Bourque, Stefan Schropp) 2:19:06 Kalshi's landmark 2024 win 2:23:05 PASPA, Murphy v. NCAA (Daniel Wallach) 2:45:14 The case against banning prediction markets (Bobby DeNault) Newsletter: Stay updated on emerging tech law for free at lawofcode.fm. https://www.lawofcode.fm/ Any feedback on this episode? Or how to improve the podcast? Click here. https://forms.gle/W4d2a5aHuLJjuNdn7 Sponsors: This episode is sponsored by Cahill Gordon & Reindel, the Hyperliquid Policy Center, and the Solana Policy Institute. To get in touch with the Cahill team about how the issues discussed in this episode apply to your situation, email [email protected]. Subscribe to Cahill's free client alerts on digital assets and emerging technology at https://www.cahill.com/news/index?search=1&practice=litigation-digital-assets-and-emerging-technology. In this episode, you'll hear from the world's leading experts on the legal layer of prediction markets: Josh Sterling, partner at Millbank Bobby DeNault, Head of Enforcement at Kalshi Chris Giancarlo, former Chairman of the CFTC Daniel Wallach, founder of Wallach Legal LLC Stefan Schropp, Senior Regulatory Counsel at Paradigm Sam Enzer, partner at Cahill Gordon & Reindel and co-chair of CahillNXT Paul Grewal, Chief Legal Officer at Coinbase Koleman Strumpf, economics professor at Wake Forest Brad Bourque, Policy Counsel at Hyperliquid Policy Center Thania Charmani, partner at Winston & Taylor Michael Passalacqua, Senior Advisor to CFTC Chairman Selig Jeff Amico, Chief Operating Officer at Gensyn Matt Kalish, co-founder of DraftKings and CEO of Hardscope Dustin Gouker, author of the Event Horizons newsletter
Disclaimer: This podcast is for informational and educational purposes only and does not constitute legal or investment advice. Views expressed by guests are their own and do not necessarily reflect those of their employers. Listening to this podcast does not create an attorney-client relationship.
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Anthropic calls some AI distillation illicit. But is distillation illegal? The answer may depend less on what you do with AI outputs than on how you accessed them. This episode is a deep dive into how courts might rule. We cover X v. Bright Data, what OpenAI's and Anthropic's terms say about who owns AI outputs, why Anthropic's own fair use arguments could be turned against it and what the labs will likely do next. Thank you to the presenting sponsor of this episode, Altitude. Visit altitude.xyz/law to learn more about their payments platform. You'll hear from the three Variant co-authors of one of the sharpest papers on the topic: Daniel Barabander, investment partner and chief legal officer at Variant Sabina Beleuz, deputy general counsel at Variant Elijah Fox, investor at Variant Read their article here: https://variant.fund/articles/license-distill-law-distillation-anthropic/. Timestamps: 0:00 What is distillation? 1:52 Intro 3:01 Why distillation matters 5:44 X v. Bright Data 7:50 Access vs. selling 10:40 Copyright preemption 11:25 Why X doesn't own your posts 13:49 From scraping to distillation 16:12 Who owns AI outputs? 19:38 Is all distillation illicit? 24:10 Anthropic's fair use problem 25:05 Bartz v. Anthropic 26:42 Predictions 28:41 Distilling the distillers 29:21 Selling services, not tokens 32:34 Antitrust 37:06 Tech moves exponentially, law sublinearly 40:47 Humans, AI and personhood 45:15 Final thoughts Thank you as well to the other sponsors of this episode: Cahill Gordon & Reindel, the Solana Policy Institute, the Hyperliquid Policy Center and the Decentralization Research Center. To get in touch with the Cahill team about how any issues discussed in this episode apply to your situation, email [email protected]. Disclaimer: This podcast is for informational and educational purposes only and does not constitute legal or investment advice. Views expressed by guests are their own and do not necessarily reflect those of their employers. Listening to this podcast does not create an attorney-client relationship.
Cybercrime costs Americans an estimated $200 billion a year, and AI is supercharging it. The U.S. government's newest response is one of the oldest tools in the Constitution, one Congress hasn't used since the War of 1812. This episode covers letters of marque and privateers: their role in the American Revolution, how prize courts and bonds kept privateers from becoming pirates, and the White House memo that trends toward implementing a modern version for cyberspace. Sponsors: This episode is presented by Altitude, visit altitude.xyz/law to learn more about their global payments platform. Sponsors also include: The law firm Cahill Gordon & Reindel. Cahill is hosting Confluence 2026, its flagship emerging tech conference, in New York City on September 24, 2026. You can apply to attend here: https://www.cahill.com/confluence2026. Thank you as well to the Solana Policy Institute and the Hyperliquid Policy Center for supporting the podcast. Guests: Chris Perkins (President of Franklin Crypto at Franklin Templeton, Naval Academy graduate and Marine Corps veteran) Ari Redbord (Global Head of Policy at TRM Labs and former federal prosecutor) Michael Coates (CISO of the Solana Foundation and previously Twitter's first CISO) Camelia Lopez Shoemaker (Holland & Knight, former DOJ) Nelson Rosario (Rosario Tech Law)
Vaults might be finance's next trillion-dollar opportunity. But what are they? How do they work? What regulation might apply? You'll hear from the creator of crypto vaults, Andre Cronje (Flying Tulip, Yearn), alongside builders Adrian Cachinero Vasiljevic (Steakhouse Financial) and Charles St. Louis (Ethereum Foundation). You'll also hear from SEC Commissioner Hester Peirce and top lawyers Lewis Cohen (Cahill), Tuongvy Le (Veda Labs), Rodrigo Seira (Cooley) and Linda Jeng (Aave). Thank you to the presenting sponsor of this episode, Altitude (altitude.xyz/law), a payments platform for the next generation. This should be the internet's best podcast on vaults. You don't need to be a lawyer, developer or finance expert to follow along. Timestamps: (0:00) Intro (4:27) What is a vault? (9:34) History of onchain vaults (11:55) The first vault, with Andre Cronje (21:05) The SEC's early interest (22:30) Investment contracts and Howey (31:28) Notes and Reves (37:10) The strategist (48:54) The curator (58:30) Investment company? (1:12:40) Investment adviser? (1:20:00) Separately managed accounts (1:30:30) Custody rules (1:55:43) What's next Thank you as well to the law firm Cahill Gordon & Reindel for sponsoring this podcast. If you'd like to join Cahill's flagship emerging tech conference, Confluence, you can apply here: https://www.cahill.com/confluence2026. Thank you as well to the Solana Policy Institute and the Hyperliquid Policy Center for supporting the podcast. Nothing in this podcast is legal or investment advice.
Commissioner Hester Peirce joins the podcast to discuss Regulation Crypto Assets, as well as secondary market trading, DePIN and vaults. If you haven't listened to the full Reg Crypto explainer, that's episode 208. This episode is presented by Altitude. Visit altitude.xyz/law to learn more about their financial operating system. Timestamps: 0:00 Intro 2:22 Secondary transactions 3:23 Promises and representations 5:05 Essential managerial efforts 8:27 Regulatory arbitrage 10:29 Form TR 16:59 Existing token projects and Form TR 18:27 Compliance costs 21:48 Secondary markets 24:12 DePIN 27:02 Vaults 35:31 Accredited investors 40:25 Tokens and equity Thank you to the other sponsors of this episode: Cahill Gordon & Reindel, the Solana Policy Institute and the Hyperliquid Policy Center. On Thursday, September 24, 2026, CahillNXT will host Confluence 2026, its flagship conference, in New York City. This year's theme, Leading the NXT Frontier, brings together regulators, institutional investors, founders, policymakers and industry leaders to examine digital assets, market structure, regulation and the emerging technologies transforming financial markets. To register your interest, email [email protected]. Newsletter: Stay updated on emerging tech law for free at lawofcode.fm. Any feedback on this episode? Or how to improve the podcast? Click here: https://forms.gle/yFFN66e8iy8shQkAA Disclaimer: This podcast is for informational and educational purposes only and does not constitute legal or investment advice. Commissioner Peirce's views are her own and do not necessarily represent those of the SEC or her fellow Commissioners. Listening to this podcast does not create an attorney-client relationship.
The GRANITE Act is a two-and-a-half-page bill designed to stop foreign governments from censoring Americans online. Preston Byrne, the Managing Partner at Byrne & Storm, has spent over a decade advising tech companies on free speech questions. His work was instrumental in the introduction of the GRANITE Act in the U.S. House of Representatives on August 27, 2026. Timestamps: 0:00 Intro 2:10 How foreign governments censor Americans 3:34 The origins of sovereign immunity 6:40 197 demands, 4 refusals 8:58 Sovereign immunity in the courts 10:58 The GRANITE Act shield 12:37 The GRANITE Act sword 17:20 Where GRANITE stands in the states, House and Senate This episode is presented by Altitude. Visit altitude.xyz/law to understand why. Thank you to the other sponsors of this episode: Cahill Gordon & Reindel, the Solana Policy Institute and the Hyperliquid Policy Center. Preston's Blog Post: https://prestonbyrne.com/2026/08/28/rulligranite/ GRANITE Act: https://www.congress.gov/bill/119th-congress/house-bill/10174/text?s=1&r=1&hl=granite Disclaimer: This podcast is for informational and educational purposes only and does not constitute legal or investment advice. Views expressed by guests are their own and do not necessarily reflect those of their employers. Listening to this podcast does not create an attorney-client relationship.