Law of Code

Can companies raise capital and issue securities directly on-chain without intermediaries or lawyers?

Gabe Shapiro is the founder of MetaLeX and a longtime crypto lawyer focused on tokenization, legal automation, and decentralized capital markets.

Timestamps:

➡️ 1:20 — Stablecoins, DeFi “kill switches,” and the new crypto narrative
➡️ 5:44 — Why custodial assets create governance power over blockchains
➡️ 11:04 — Tokenized securities vs. today’s DTCC intermediary model
➡️ 21:36 — How MetaLeX enables direct issuer-to-investor capital raises
➡️ 23:12 — Private keys as legal signatures and atomic deal execution
➡️ 27:58 — Privacy concerns and on-chain legal infrastructure
➡️ 33:43 — Low-KYC accreditation and composable legal credentials
➡️ 34:23 — Reversibility, bearer instruments, and issuer controls
➡️ 39:34 — TradFi, L2s, and whether Wall Street is “eating crypto”
➡️ 43:38 — What regulators are missing: CFTC derivatives rules and UCC reform

Sponsor: This episode is brought to you by the Decentralization Research Center (DRC), a nonprofit think tank advocating for decentralization in emerging technologies. Learn more at thedrcenter.org.

Resources:

📄 Dragonfly Capital's Article "Ethereum is now unforkable, thanks to DeFi"

📄 Shapiro's Article "cyberSign: easy legal agreements on Ethereum"

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.

Crypto’s current policy window in Washington is a rare opportunity to pass market structure legislation. What happens if the industry walks away from a compromise now?

Bill Hughes, Senior Counsel and Director of Global Regulatory Matters at Consensys, joins the podcast to discuss crypto market structure and stablecoin policy.

Timestamps

➡️ 1:10 — Why Agriculture and Banking Committees shape crypto legislation
➡️ 4:20 — How agencies influence drafting behind the scenes
➡️ 6:40 — Stablecoin yield and illicit finance: the real sticking points
➡️ 9:20 — DeFi regulation debates
➡️ 17:00 — Is the Clarity Act likely to pass in 2026?
➡️ 18:00 — Ethics provisions and political tensions
➡️ 20:13 — Coinbase’s strategy
➡️ 26:35 — Stablecoin yield fights
➡️ 33:00 — Legislative timelines
➡️ 45:36 — What to watch next

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:

📓 The latest market structure discussion draft (banking committee)

📓 ⁠The GENIUS Act

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.

How should employees, contractors, and companies think about token compensation? What are the legal, tax, and governance risks?

Jessica Furr is a lawyer focused on crypto compensation, governance, and market structure, and the author of Read the Fine Print on Token Compensation. Brandon Ferrick is a crypto and securities lawyer who advises companies on token incentive plans, equity compensation, and regulatory compliance.

Timestamps:

➡️ 1:28 — Why tokens are not equity (and why people assume they are)
➡️ 3:32 — Why token compensation exists alongside equity
➡️ 6:39 — What documents to look for in a token comp arrangement
➡️ 9:24 — Are tokens securities? How lawyers actually approach classification
➡️ 11:57 — Restricted Token Awards (RTAs) vs. Restricted Token Units (RTUs)
➡️ 13:28 — How tax treatment drives RTA vs. RTU decisions
➡️ 16:49 — What an 83(b) election is and why it matters for tokens
➡️ 21:16 — What employees should negotiate and clarify upfront
➡️ 25:45 — Emerging trends in token compensation structures
➡️ 28:28 — Where token compensation could go next

Sponsor: This episode is brought to you by the Decentralization Research Center (DRC), a nonprofit think tank advocating for decentralization in emerging technologies. Learn more at thedrcenter.org.

Resources:

📕 Jessica and Brandon's paper Read the Fine Print: Token Compensation

📄 Rule 701 of the Securities Act

📓 Dragonfly Compensation Report

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.

How do prediction markets actually work, and why are state gaming regulators and the CFTC battling over who has jurisdiction to regulate?

Samir Patel is an attorney at Holland & Knight, where he focuses on gambling law, prediction markets, and the intersection of crypto, derivatives, and state gaming regulation.

Timestamps:

➡️ 1:02 — What prediction markets are and how binary contracts work

➡️ 2:51 — Prediction markets vs. sports gambling: what’s legally different?

➡️ 4:02 — Are prediction markets actually “on-chain”?

➡️ 7:37 — The CFTC vs. state gaming regulators: who has jurisdiction?

➡️ 9:55 — Swaps, self-certification, and the Commodities Exchange Act

➡️ 12:06 — How courts are splitting on federal preemption

➡️ 14:39 — Why the CFTC’s silence matters more than the lawsuits themselves

➡️ 18:58 — DCMs vs. FCMs: mapping the regulatory plumbing

➡️ 22:00 — Prediction markets as information tools, not just bets

➡️ 23:30 — What this litigation could mean for crypto and DeFi governance

Sponsor: This episode is brought to you by the Decentralization Research Center (DRC), a nonprofit think tank advocating for decentralization in emerging technologies. Learn more at thedrcenter.org.

Resources:

📓 Commodity Exchange Act (CEA)

📓 CFTC Rule 40.11

📄 CFTC Staff Advisory Withdrawal of Prior Guidance on Events Contracts

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 could the future of U.S. crypto regulation look like from the CFTC—and how should regulators approach tokenization, prediction markets, and stablecoins as digital finance moves on-chain?

Chris Giancarlo is Senior Counsel for Corporate and Financial Services at Willkie Farr & Gallagher and the former Chair of the U.S. Commodity Futures Trading Commission, where he oversaw the regulation of futures, options, and swaps markets, including the launch of Bitcoin futures.

Timestamps:

➡️ 1:15 — Advice for new CFTC Chair Mike Selig

➡️ 3:06 — Why crypto inverts the CFTC’s traditional regulatory model

➡️ 6:53 — How the SEC and CFTC should divide authority over digital assets

➡️ 8:54 — Why the commodity vs. security distinction still matters

➡️ 15:13 — DTCC’s no-action relief and the future of tokenized market infrastructure

➡️ 19:27 — Will TradFi absorb crypto—or will crypto reshape TradFi?

➡️ 21:46 — Prediction markets, federal preemption, and state resistance

➡️ 27:40 — Why prediction markets need regulation, not suppression

➡️ 29:42 — Stablecoins, privacy, and exporting U.S. values through digital dollars

Sponsor: This episode is brought to you by the Decentralization Research Center (DRC), a nonprofit think tank advocating for decentralization in emerging technologies. Learn more at thedrcenter.org.

Resources

📺 Recording of the CFTC / SEC Joint Event on Harmonization

📓 GENIUS Act

📄 DTCC No Action Letter

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.

Why are crypto custody rules for registered investment advisors due for modernization — and what could a future-proof framework look like?

Sarah Helena Brennan is the General Counsel for Delphi Ventures, and Jay Stolkin is the Deputy General Counsel at Multicoin Capital. 

Timestamps:

➡️ 0:05 — Why the custody rule matters for crypto

➡️ 1:27 — The SEC’s safeguarding proposal and why this paper was written

➡️ 5:58 — What the custody rule and “qualified custodians” actually require

➡️ 10:26 — Why digital assets challenge legacy custody assumptions

➡️ 14:47 — Fees, loss of utility, and concentration risk under the status quo

➡️ 18:21 — The case for optionality and a flexible custody framework

➡️ 22:53 — The five core tenets of cryptoasset safeguarding

➡️ 25:50 — Lessons from the privately offered securities exemption

➡️ 28:27 — On-chain verification, auditors, and real-time transparency

➡️ 32:16 — Where regulators may push back—and what comes next

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: 

📄 Sarah and Jay’s Whitepaper
📓 SEC Agency Rule List

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 the industry be watching in 2026?

Drew Hinkes is a partner at Winston & Strawn and a longtime crypto lawyer whose work spans DeFi, market structure, tokenization, and digital asset regulation. 

Timestamps:

➡️ 1:53 — Tokenization, RWAs, and institutional crypto’s next phase

➡️ 4:00 — Market structure gaps and DeFi’s unresolved treatment

➡️ 6:09 — AML creep and the risk to permissionless finance

➡️ 8:15 — Why DeFi depends on interfaces—and where regulation can bite

➡️ 12:28 — Grey areas after market structure: why uncertainty remains

➡️ 17:05 — Equity vs. tokens and what token holders are actually promised

➡️ 23:57 — Tokenization vs. TradFi capture: competition or consolidation

➡️ 29:03 — The biggest systemic risks to crypto in 2026

➡️ 31:17 — Crypto’s most underappreciated source of resilience

Sponsor: This episode is brought to you by the Decentralization Research Center (DRC), a nonprofit think tank advocating for decentralization in emerging technologies. Learn more at thedrcenter.org. 

Resources: 

📓 Latest Senate Banking Committee Market Structure Draft

📓 Latest Senate Agriculture Committee Market Structure Draft

📄 SEC No-Action Letter to DTCC on Tokenization Services

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.

In this episode, Jacob Robinson and Jonathan Schmalfeld break down the biggest U.S. crypto law and policy developments of the month, from the SEC’s moves toward bringing public markets on-chain to major CFTC moves on derivatives, prediction markets, and collateral. The conversation also covers crypto tax proposals, DeFi governance disputes, banking access, privacy, quantum risk, and why regulators increasingly view crypto not as an exception, but as core financial infrastructure.

Jonathan Schmalfeld is the Policy Director at The Digital Chamber and the author of the Off the Blockchain+ newsletter, where he analyzes crypto regulation, market structure, and emerging policy trends.

Timestamps:

➡️ 1:03 — SEC market structure reforms and DTC no-action relief

➡️ 7:54 — CFTC allows crypto and tokenized treasuries as collateral

➡️ 8:45 — Prediction markets and state gambling laws

➡️ 13:23 — Crypto tax proposals: wash sales, staking, and airdrops

➡️ 16:03 — Aave, DAO governance, and token vs. equity conflicts

➡️ 21:48 — GENIUS Act implementation and stablecoin interest debates

➡️ 27:33 — The end of Operation Choke Point 2.0 and legislative fixes

➡️ 31:02 — DeFi liquidations, market manipulation, and public debate

➡️ 34:20 — Quantum computing risk and Bitcoin’s long-term resilience

➡️ 38:46 — Michael Selig confirmed as CFTC Chair

Sponsor: This episode is brought to you by the Decentralization Research Center (DRC), a nonprofit think tank advocating for decentralization in emerging technologies. Learn more at thedrcenter.org.

Resources: 

📄 SEC’s No Action Letter to the DTC

✉️ CFTC Digital Assets Pilot Program Announcement

📓 Draft of the PARITY Act

📄 FDIC Notice of Proposed Rulemaking for Stablecoins

✉️ ⁠Jonathan’s Off the Blockchain+ Newsletter⁠

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.

In this episode, Jacob Robinson speaks with Odun Olowookere about Canada’s proposed Stablecoin Act, the constitutional and regulatory challenges it raises, and why critics argue it may reduce clarity rather than enhance it. 

Odun Olowookere is a legal scholar at York University and the co-author of a submission to Canada’s House of Commons critiquing the draft Stablecoin Act, alongside Darrell Duffie of Stanford University and Andreas Veneris of the University of Toronto.

Timestamps:

➡️ 0:05 — Why Canada’s draft Stablecoin Act has drawn concern

➡️ 2:13 — The Act’s stated goal: monetary sovereignty and dollarization risk

➡️ 3:16 — Why stablecoins are not explicitly defined as payment instruments

➡️ 5:20 — How Canada’s constitutional structure complicates stablecoin regulation

➡️ 8:41 — Canada’s blanket prohibition on interest and how it differs from GENIUS

➡️ 9:46 — Expanded “payment function” language and why it alarms critics

➡️ 10:33 — How wallets, validators, and even users could be swept into regulation

➡️ 16:14 — Data security obligations and the Bank of Canada’s technical capacity

➡️ 18:33 — Prudential regulation concerns and undefined reserve requirements

➡️ 21:48 — Is Canada regulating stablecoins too early?

Sponsor: This episode is brought to you by the Decentralization Research Center (DRC), a nonprofit think tank advocating for decentralization in emerging technologies. Learn more at thedrcenter.org.

Resources: 

📓 The Canadian Stablecoin Act Draft Text

📄 Odun, Andreas Veneris, and Darrell Duffie’s Written submission to the House of Commons in reply to The Stablecoin Act

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.

DeFi has always promised trust without intermediaries, but as the ecosystem matures, that promise is being stress-tested by hacks, institutional risk limits, and regulatory pressure.

To unpack whether DeFi can scale without sacrificing neutrality or permissionlessness, Katherine Kirkpatrick Bos, General Counsel of StarkWare, and Jessi Brooks, General Counsel & Chief Compliance Officer at Ribbit Capital, joined the podcast to discuss their paper “Trust Without Intermediaries: A Programmable Risk Management Framework for the Future.”

The paper sparked controversy across the DeFi community, with critics arguing it could open the door to protocol-level compliance or re-intermediation. In this episode, Katherine and Jessi explain that the paper proposes something different.

Timestamps:

➡️ 01:31 — Why write this paper?

➡️ 07:55 — Institutional DeFi and why one-size-fits-all doesn’t work

➡️ 09:43 — Compliance as a commercial choice, not a mandate

➡️ 11:38 — Risk scoring in DeFi

➡️ 15:37 — Technical de-risking

➡️ 18:23 — Optional evolution

➡️ 20:59 — Not protocol-level compliance

➡️ 25:49 — Opt-in DeFi

➡️ 30:44 — Lessons from the backlash and public debate

& much more.

Sponsor: : ⁠⁠ This episode is brought to you by ⁠⁠⁠Day One Law⁠, a boutique law firm helping crypto startups navigate complex legal challenges. Subscribe to ⁠⁠⁠Day One’s free monthly newsletter⁠⁠⁠ for legal and regulatory updates.

Resources:

📄 Trust Without Intermediaries: A Programmable Risk Management Framework for the Future

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.