Understand the legal layer of emerging technology.
Conversations with top lawyers, regulators, and entrepreneurs on the laws and policy decisions shaping our future.
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#207 - Crypto in Canada
Episode 207
Monday, August 10, 2026 • Duration 59:54
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.
Interview: Legora's Kyle Poe on the Future of AI & Law Firms
Season 2
Thursday, August 6, 2026 • Duration 30:08
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.
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.
#205 - Code & Free Speech
Season 2 · Episode 205
Monday, July 13, 2026 • Duration 02:00:48
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
#204 - Prediction Markets
Season 2 · Episode 204
Tuesday, June 30, 2026 • Duration 02:55:47
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)
1:38:18 Cardi B and the resolution problem (Dustin Gouker)
#203 - How the SEC Writes Crypto Rules
Season 2 · Episode 203
Monday, June 15, 2026 • Duration 59:26
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/
#202 - Perps
Season 2 · Episode 202
Monday, June 1, 2026 • Duration 02:13:32
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
#201 - The CLARITY Act
Season 2 · Episode 201
Monday, May 18, 2026 • Duration 01:53:46
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
#200 - Money Transmission & Developer Liability
Season 2 · Episode 200
Monday, May 4, 2026 • Duration 01:49:26
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
Sign up for the free Law of Code newsletter at lawofcode.fm.
Sign up for the free Law of Code newsletter at lawofcode.fm.
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 mtomsky@cahill.com.
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.
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
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.
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)
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 mtomsky@cahill.com. 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.
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.
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.
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.
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.
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.
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