Law of Code

How does Canada regulate crypto? This podcast answers that in less than 60 minutes.

You'll hear from Grant Vingoe, CEO of the OSC, Eric Richmond, CEO of Coinbase Canada, the Bank of Canada's Anne Butler, McCarthy's Lori Stein, Osler's Matt Burgoyne, Evan Thomas, Dr. Ryan Clements of the ASC and Blair Wiley of Wealthsimple.

Law of Code is presented by Altitude, visit ⁠https://altitude.xyz/law⁠ to learn why.

Timestamps:

0:00 Intro

2:42 Tax

4:53 AML Rules

8:06 Securities

12:00 Investment contracts

16:13 Quadriga's collapse

23:00 The Crypto Contract

34:29 World's first Bitcoin ETF

38:23 Stablecoins

46:47 Where Canada could play offense: DeFi, perps and tokenization

52:53 The speed problem

Nothing in this podcast is legal or investment advice.

Thank you to our other sponsors:

McCarthy Tétrault LLP, with which I am co-hosting a Crypto in Canada event on August 12, 2026 in Toronto: https://luma.com/89qnrnah

Osler, Hoskin & Harcourt LLP: https://www.osler.com/en/expertise/services/digital-assets-and-blockchain/

Cahill Gordon & Reindel LLP: ⁠https://www.cahill.com/practices/litigation-digital-assets-and-emerging-technology⁠

Solana Policy Institute: ⁠https://www.solanapolicyinstitute.org/⁠

Hyperliquid Policy Center: ⁠https://hyperliquidpolicy.org/⁠

Sign up for the free Law of Code newsletter at lawofcode.fm.

Kyle Poe is a former BigLaw partner and currently VP of Legal Innovation and Strategy at Legora, a legal AI startup valued at $5.6 billion.

Kyle explains why he sees a generational reordering happening in the legal profession, how firms are best institutionalizing partner knowledge as IP, and where the moat exists for lawyers as AI grows in ubiquity.

Law of Code is presented by Altitude, visit https://altitude.xyz/law to learn why.

Timestamps:

0:00 Intro

0:56 The billable hour and the incentive problem inside firms

2:36 Institutionalizing partner knowledge as firm IP

4:02 Why partner buyouts are accelerating

5:56 Why AI is different from the internet and email

9:31 How top firms are operationalizing AI

12:35 Building innovation teams from the top down

14:37 More lawyers or fewer? The future of demand

19:20 Grinders, minders and finders

22:10 What lawyers should be asking about AI

25:13 Legora's moat

Thank you to our other sponsors:

Cahill Gordon & Reindel LLP: https://www.cahill.com/practices/litigation-digital-assets-and-emerging-technology

Solana Policy Institute: https://www.solanapolicyinstitute.org/

Hyperliquid Policy Center: https://hyperliquidpolicy.org/

Sign up for the free Law of Code newsletter at lawofcode.fm.

By the end of this episode, you'll understand how lawyers are actually AI maxxing in 2026, and how you can, too.

Timestamps:

0:00 Intro

1:58 Why it's the best time to be a lawyer

3:03 Hallucinations and cognitive surrender

5:33 Quality over efficiency

8:13 Why AI upends legal work

15:20 60% of contracts filed to EDGAR have mistakes

20:04 How LLMs actually work

25:59 Zero data retention, explained

29:16 The privacy risk beyond training

39:16 How to prompt

47:03 Michael Showalter's AI-native litigation stack

55:27 Spellbook's Compare to Market Feature

1:03:10 Building a regulatory agent

1:09:50 The judgment crisis for junior lawyers

1:12:15 Cooley's AI training method

You'll hear from 10 people at the cutting edge of legal AI:

• Zack Shapiro, Founder and Managing Partner at Rains LLP
• Molly Abraham, General Counsel at Coinbase
• Sujit Raman, Chief Legal Officer at TRM Labs
• Michael Showalter, Founder of Showalter PLLC
• Erich Dylus, attorney, programmer and creator of CamoText
• Aaron Kelly, General Counsel and open source AI expert
• David Wang, Chief Innovation Officer at Cooley
• Scott Stevenson, CEO of Spellbook
• Justin McCallon, CEO of StrongSuit
• Samson Enzer, Partner at Cahill Gordon & Reindel

This episode is presented by Altitude, visit altitude.xyz/law to learn more about their financial operating system.

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://docs.google.com/forms/d/1QAcE1sQAKZIkma20DbyB5frgKdiK8UB6Fkb6CwaVP1I/edit

Sponsors: Thank you to the Hyperliquid Policy Center and Solana Policy Institute for supporting this podcast.

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.

When should software lose free speech protections?

This podcast covers software and the First Amendment, tracing the history from Cold War export controls to recent restrictions on advanced AI models.

My goal: the internet's most comprehensive explainer on speech and code, from cryptography to cryptocurrency to AI.

In this episode, you'll hear from leading experts on the legal layer of software and free speech:

• Peter Van Valkenburgh, Executive Director at Coin Center
• Laz Pieper, Director of Research at Coin Center
• Eugene Volokh, First Amendment scholar and Fellow at the Hoover Institution
• Jane Bambauer, Brechner Eminent Scholar at the University of Florida
• Preston Byrne, Managing Partner at Byrne & Storm
• Sam Enzer, partner at Cahill Gordon & Reindel and co-chair of CahillNXT

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

This episode is presented by Altitude, visit Altitude.xyz/law to learn more about their financial operating system.

Timestamps:

0:00 Anthropic AI export controls

6:17 Introduction

9:39 Reading the First Amendment

10:38 Eugene Volokh on his First Amendment philosophy

13:42 The machine gun sculpture: speech vs function

19:24 Peter Van Valkenburgh interview

25:50 The Cold War, munitions list and Phil Zimmermann

29:57 The Bernstein case

34:53 Strict scrutiny

38:48 The Corley case

49:17 Sorrell, Stevens and where the Supreme Court is heading

53:25 Preston Byrne on the Supreme Court's AI case

57:23 Defense Distributed and 3D-printing

1:04:00 Where publication ends and professional conduct begins

1:15:20 Lowe v. SEC and the agency line

1:45:45 Compelled speech, the IRS broker rule and tobacco labels

2:04:17 Laz Pieper on Sorrell and third-party liability

2:11:29 Preston Byrne on the GRANITE Act and foreign censorship

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: Thank you to the Hyperliquid Policy Center and Solana Policy Institute for supporting this podcast.

To get in touch with the Cahill team about how any 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.

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.

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 non-lawyers 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.