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.

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

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.

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.

How do regulators actually write the rules for crypto? SEC Commissioner Hester Peirce and Taylor Lindman, Chief Counsel of the SEC's Crypto Task Force, take us inside the process, recorded at the SEC offices in Washington, D.C.

We cover CLARITY Act rulemaking, lessons from Dodd-Frank, principles-based regulation and navigating the risks of decentralized projects. If you want to understand how an agency like the SEC actually works, this episode is for you.

Timestamps:

0:00 Intro

1:20 Commissioner Peirce's philosophy on capital markets

5:04 Rulemaking at the SEC

6:48 The SEC's divisions, explained

8:27 How the Crypto Task Force is staffed

10:37 Lessons from Dodd-Frank

13:10 Legal artisans

15:15 The Clarity Act deadlines

18:55 Decentralized intermediaries

20:56 Principles-based vs prescriptive regulation

24:49 Tackling difficult crypto questions

26:23 Leveraging AI for data review

29:46 "Come in and register" under this SEC

33:50 SEC & CFTC collaboration

35:52 Re-engaging the crypto industry

40:00 Crypto Task Force & the Clarity Act

45:54 The SEC's non-crypto priorities

48:41 Avoiding another regulation-by-enforcement era

57:14 Thank you to Sam Enzer, Lewis Cohen and Cahill, plus a shoutout to Day One Law and Nick Pullman

Newsletter: I'm re-launching the Law of Code newsletter soon: you can ⁠⁠⁠stay updated on emerging tech law for free here⁠⁠⁠: https://www.lawofcode.fm/

Any feedback on this episode? Or how to improve the podcast? ⁠⁠Click here: https://forms.gle/W4d2a5aHuLJjuNdn7

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.

Over a trillion dollars worth of perps are traded every month, yet 99% people have never heard of them. Fewer understand how they work.

This podcast is a multi-hour deep dive on perps, starting from the history of grain futures in Chicago to a historic CFTC announcement on Friday, May 29, 2026.

My goal: The internet's most comprehensive explainer on perps.

In this episode, you'll hear from the world's leading experts on the legal layer of perps:

• Hyperliquid Policy Center CEO Jake Chervinsky and policy counsel Brad Bourque
• BrettHarrison, CEO of Architect
• Katherine Kirkpatrick Bos, general counsel of StarkWare
• Ryne Miller, partner at Morrison Foerster
• Mike Frisch, partner at Croke Fairchild
• David Shafer, lawyer at Coinbase

By the end of this episode, I promise you'll be in the top percentile for understanding perps, regardless of where you're starting from. (You just might need to listen twice. There's a lot here.)

Timestamps:

0:00 Intro

4:04 What is a perp?

7:18 Why futures contracts exist

8:15 Liquidity fragmentation

11:01 History of U.S. futures

17:08 Richard Nixon, the gold standard and financial futures

21:27 Birth of the CFTC

24:27 Robert Shiller's 1992 paper

30:09 Price convergence

32:00 The funding rate

43:41 Oracles and manipulation risk

47:39 Are perps swaps or futures?

52:44 A @ChairmanSelig clip on perps

54:02 The DCM framework

59:16 DCMs, DCOs and FCMs explained

1:04:55 History of crypto perps (BitMEX, FTX)

1:13:00 How Hyperliquid works

1:25:41 CFTC's historic announcements on May 29, 2026

1:35:00 Fireside with @jchervinsky and @BradBourque of @HyperliquidPC

Newsletter: I'm re-launching the Law of Code newsletter soon: you can ⁠⁠⁠stay updated on emerging tech law for free here⁠⁠⁠. https://www.lawofcode.fm/

Any feedback on this episode? Or how to improve the podcast? ⁠⁠Click here⁠⁠. https://forms.gle/W4d2a5aHuLJjuNdn7

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.

What is the CLARITY Act? Maybe the most important piece of financial legislation in a generation.

This podcast explains the history of U.S. digital asset regulation, why regulation-by-enforcement failed and what the CLARITY Act addresses, plus remaining steps for this to become law.

Guests:

• Lewis Cohen, Partner & Co-Chair of CahillNXT's Digital Assets & Emerging Technology practice
• Miles Jennings, Head of Policy & General Counsel for a16z crypto
• Sarah Brennan, general counsel at Delphi Ventures
• Kyle Bligen, Head of Policy and Public Affairs at the Decentralization Research Center
• Miller Whitehouse-Levine, CEO at Solana Policy Institute
• Dugan Bliss, Head of Litigation at Binance

By the end of this episode, I promise you'll be in the 99th percentile for understanding CLARITY, regardless of whether you're a lawyer, builder or operator.

Timestamps:

0:00 Intro

4:46 Explaining market structure

6:05 Regulatory distortion

10:43 Predecessor bills

13:35 Senate Banking markup takeaways

15:46 SEC & CFTC

20:37 The Securities Act of 1933

23:07 The Howey Test

25:26 The Ineluctable Modality of Securities Law

28:51 SEC enforcement

32:32 Why SEC rulemaking isn't enough

37:36 Titles of CLARITY

40:00 Digital commodities

47:29 Investment contract principles

54:10 Promoters: originators

58:18 Promoters: related persons

1:04:13 Token taxonomy

1:11:02 Ancillary asset requirements

1:19:34 The certification process

1:28:32 Remaining hurdles for CLARITY

1:34:50 Stablecoin yield

1:38:45 Ethics

1:45:50 Tax consequences

1:48:54 Thanking people working on the bill, such as @SenLummis, @gillibrandny, @SenatorTimScott, @SenatorHagerty, @SenThomTillis, @MarkWarner, @SenRubenGallego, @Sen_Alsobrooks, their staffs & many, many others.

Newsletter: I'm re-launching the Law of Code newsletter soon: you can ⁠⁠⁠stay updated on emerging tech law for free here⁠⁠⁠. https://www.lawofcode.fm/

Any feedback on this episode? Or how to improve the podcast? ⁠⁠Click here⁠⁠. https://forms.gle/W4d2a5aHuLJjuNdn7

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.

Can the U.S. government send a software developer to prison for writing and publishing code?

That's the question at the center of the Tornado Cash and Samourai Wallet prosecutions, and every crypto founder, builder and investor should understand the answer.

This deep-dive episode walks through the history of U.S. money transmission law, how the DOJ is applying it to non-custodial software developers, what the Roman Storm verdict actually means, and what new legislation could change in 2026.

Guests:

• Peter Van Valkenburgh — Executive Director, Coin Center
• Amanda Tuminelli — Chief Executive Officer, DeFi Education Fund
• Brian Klein — Partner at Cooley, lead defense attorney for Roman Storm
• Jake Chervinsky — Hyperliquid Policy Center (cameo)

This is the most comprehensive podcast I've ever done. Welcome to Law of Code, Season 2.

Timestamps:

0:00 Intro

3:18 What's at stake?

4:40 Which developers are at risk

6:03 Custodial vs. non-custodial

9:32 What is a money transmission license?

9:47 Steamships, the telegraph & Western Union

12:14 The Bank Secrecy Act

13:38 Section 1960

15:26 The Patriot Act

19:39 FinCEN's 2013 and 2019 guidance

24:42 OFAC sanctions Tornado Cash

27:30 How Tornado Cash works

30:48 Coin Center v. Yellen

32:24 DOJ indicts Roman Storm, Roman Semenov, Roman Sterlingov & Samourai Wallet developers

35:15 The Van Loon win

40:33 Developer losses

43:48 Bad facts make bad law

48:46 Brian Klein on Roman Storm's case

50:50 The Brady letter

57:00 Michael Lewellen sues for answers

1:09:24 The Blanche memo

1:18:46 The Galeotti speech

1:26:13 Catch-22 for developers

1:30:03 The chilling effect on U.S. innovation

1:33:48 Blockchain Regulatory Certainty Act

1:38:03 Promoting Innovation in Blockchain Development Act

1:45:28 What's next

Nothing in this podcast is legal or investment advice.

Newsletter: I'm re-launching the Law of Code newsletter soon: you can ⁠⁠⁠stay updated on emerging tech law for free here⁠⁠⁠. https://www.lawofcode.fm/

Any feedback on this episode? Or how to improve the podcast? ⁠⁠Click here⁠⁠. https://forms.gle/W4d2a5aHuLJjuNdn7

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.

Does attorney-client privilege exist when you use ChatGPT or Claude? Should it?

Jacob Robinson sits down with Mike Katz, Partner at Manatt Phelps & Phillips, to examine whether attorney-client privilege, work product or any analogous protection applies when people ask AI chatbots legal questions.

Timestamps:

➡️ 0:00 — Background

➡️ 1:47 — What is attorney-client privilege?

➡️ 2:44 — Policy reasons for narrowing privilege

➡️ 3:30 — The Upjohn case (1981)

➡️ 4:34 — Privilege vs. work product doctrine

➡️ 5:17 — Three elements to establish privilege

➡️ 7:23 — Consumer AI terms of service and confidentiality

➡️ 8:09 — How you lose privilege

➡️ 11:30 — War stories

➡️ 15:39 — Vibe lawyering

➡️ 19:09 — Could Anthropic, OpenAI be liable?

➡️ 22:48 — The Heppner case (2026)

➡️ 26:26 — The Kovel doctrine (1961)

➡️ 28:14 — Incognito mode & deleted chats

➡️ 30:59 — The policy question

➡️ 34:00 — This is not a new problem

➡️ 37:05 — Are lawyers coal or horses? Jevons Paradox

Sponsor: Day One Law, a boutique corporate law firm that provides strategic legal counsel to startups, crypto projects, and Web3 innovators. ⁠You can get in contact with them via this link⁠: ⁠⁠https://www.dayonelaw.xyz/#contact.

Also: I'm re-launching the Law of Code newsletter as the world's shortest legal newsletter! You can ⁠⁠stay updated on emerging tech law for free here⁠⁠. https://www.lawofcode.fm/

Any feedback on this episode? Or how to improve the podcast? ⁠Click here⁠. https://forms.gle/W4d2a5aHuLJjuNdn7

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.

When does U.S. law require Circle to freeze USDC? It's a question many are asking after a series of wallets were frozen in connection to a sealed civil case, and again after Solana's Drift Protocol was drained of $285 million.

Jacob Robinson is joined by Austin Campbell, founder of Zero Knowledge Consulting and adjunct professor at Columbia Business School, for a masterclass on the legal framework governing stablecoin freezes.

Timestamps:

➡️ 0:00 — Intro

➡️ 2:00 — The March 2026 freeze of 16 wallets tied to a sealed civil case

➡️ 4:31 — How bank freezes actually work

➡️ 7:27 — Circle's legal obligation to freeze

➡️ 9:40 — Does Circle's terms of service even apply to secondary holders?

➡️ 11:24 — The privity problem

➡️ 13:20 — The five-piece legal framework that functions like a safe harbor for institutions freezing assets

➡️ 16:43 — DeFi's second-order exposure to asset freezes

➡️ 18:29 — Can DeFi adapt?

➡️ 21:03 — Circle's response to the Drift exploit

➡️ 22:34 — DeFi and the legal system

➡️ 24:27 — Bitcoin as the ideologically consistent alternative

➡️ 28:18 — Why people want intermediaries with liability

➡️ 31:04 — The Drift exploit: why Circle should have frozen USDC

➡️ 36:34 — The exploit difficulty

➡️ 38:27 — Real world assets on chain: the DeFi trilemma

Sponsor: Day One Law, a boutique corporate law firm that provides strategic legal counsel to startups, crypto projects, and Web3 innovators. ⁠You can get in contact with them via this link⁠: ⁠⁠https://www.dayonelaw.xyz/#contact.

Resources:

• 📓 Circle's April 10, 2026 statement on the Drift exploit and USDC freeze authority by Dante Disparte
• 📓 ZachXBT's X thread on Circle's USDC freeze history

Also: I'm re-launching the Law of Code newsletter as the world's shortest legal newsletter! You can ⁠stay updated on emerging tech law for free here⁠. https://lawofcode.beehiiv.com/

Any feedback on this episode? Or how to improve the podcast? Click here. https://forms.gle/W4d2a5aHuLJjuNdn7

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.

What are the risks of allowing financial institutions to cut off access to the economy for lawful but controversial activity?

Rainey Reitman is a civil liberties advocate and the author of Transaction Denied, a comprehensive investigation into debanking, financial censorship, and the growing role of financial institutions in regulating speech. She previously worked at the Electronic Frontier Foundation and co-founded the Freedom of the Press Foundation.

Timestamps:

➡️ 1:20 — Why cash functions as a civil liberty (privacy + censorship resistance)
➡️ 3:21 — What inspired Transaction Denied and early experiences with debanking
➡️ 5:20 — The Chelsea Manning Support Network PayPal freeze
➡️ 8:27 — Operation Chokepoint and the rise of financial censorship
➡️ 11:25 — “Banking while Muslim” and over-compliance with sanctions
➡️ 15:08 — The Patriot Act and incentives for financial surveillance
➡️ 17:12 — Financial intermediaries and the power to block transactions
➡️ 17:48 — Bitcoin, custodians, and whether crypto solves debanking
➡️ 19:33 — Why financial censorship affects everyone—not just targeted groups
➡️ 21:58 — NRA v. Vullo and the limits of government pressure on banks

Sponsor: Day One Law, a boutique corporate law firm founded by Nick Pullman. Nick and his team at Day One provide strategic legal counsel to startups, crypto projects, and Web3 innovators. ⁠You can get in contact with them via this link⁠: ⁠⁠https://www.dayonelaw.xyz/#contact

Resources:

📚 Pre-order Transaction Denied

📖 The Patriot Act 

👩‍⚖️ Supreme Court decision in National Rifle Association v. Vullo

Disclaimer: This podcast is for informational and educational purposes only and does not constitute legal or investment advice. Views expressed by the guest are their own and do not necessarily reflect those of their employers. Listening to this podcast does not create an attorney-client relationship.

What should crypto founders know about the SEC and CFTC's joint interpretive guidance on securities law?

Joining to discuss is Joe Doll (@Sh0edog), Counsel at Day One Law and previously General Counsel at a crypto startup. Joe wrote a detailed breakdown of the guidance aimed at founders, which we walk through from start to finish.

Timestamps:

➡️ 0:00 — Intro

➡️ 0:07 — Why the Howey Test exists

➡️ 3:11 — Why tokens are not necessarily securities

➡️ 7:47 — The five-category token taxonomy explained

➡️ 8:45 — Digital commodities

➡️ 12:13 — The four-factor "statement" test

➡️ 15:57 — Why the guidance might chill disclosure

➡️ 19:32 — Joe's proposal for a minimum attachment period

➡️ 23:30 — Fungibility and the token sales problem

➡️ 28:29 — Decentralization, disclosure obligations, and the CLARITY Act

➡️ 29:41 — Why the attachment theory better serves the policy goals of securities law

➡️ 31:51 — Airdrops

➡️ 37:53 — The CLARITY Act's control framework

➡️ 38:58 — Linux, Red Hat, and the case for immutability

➡️ 43:12 — Equity versus token value

➡️ 43:25 — The story behind the handle @sh0edog

➡️ 45:04 — Decentralized communities

Resources:

• 📓 Joe Doll's article breaking down the SEC and CFTC interpretive guidance for founders
• 📓 SEC and CFTC joint interpretive release on the application of securities laws to crypto assets

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. Obviously.

When does transacting in a crypto asset become a securities transaction? The SEC and CFTC recently issued an interpretation clarifying how the federal securities laws apply to certain crypto assets and transactions involving crypto assets.

Joining to discuss that is Lewis Cohen, co-chair of Cahill’s digital assets and emerging technologies practice and one of the leading experts on the application of U.S. securities laws to crypto.

Timestamps:

➡️ 2:26 — Why a token can be a non-security asset, but still sold in a securities transaction
➡️ 4:21 — The SEC’s “attachment and separation” concept explained
➡️ 7:22 — Secondary market transactions and the limits of existing case law
➡️ 11:15 — Why third parties may be exposed to securities law risk
➡️ 14:09 — Who counts as an “issuer” in crypto—and why the concept breaks down
➡️ 17:56 — What qualifies as a promise or representation under Howey
➡️ 23:27 — Why disclosure—not classification—is the real solution
➡️ 25:46 — Can an investment contract “detach” once promises are fulfilled?
➡️ 30:19 — Civil liability, enforcement risk, and second-order market effects
➡️ 34:42 — The danger of bifurcated markets and uneven information access

Sponsor: Day One Law, a boutique corporate law firm founded by Nick Pullman. Nick and his team at Day One provide strategic legal counsel to startups, crypto projects, and Web3 innovators. ⁠You can get in contact with them via this link⁠: ⁠⁠https://www.dayonelaw.xyz/#contact

Resources:

📓 SEC’s interpretive release on the application of security laws to crypto assets and transactions

✍️ Lewis Cohen's client alert on the recent guidance

Disclaimer: This podcast is for informational and educational purposes only and does not constitute legal or investment advice. Views expressed by the guest are their own and do not necessarily reflect those of their employers. Listening to this podcast does not create an attorney-client relationship.