Crypto tax expert Jason Schwartz joins the podcast to break down what founders get wrong about taxes — and what’s changing in 2025.

Jason is a partner at Cahill NXT, where he specializes in the tax treatment of digital assets, financial products, and decentralized protocols. In this episode, he shares insights on how projects are approaching structuring, the rise of 501(c)(4) entities, common tax pitfalls with Cayman foundations, and how the IRS might soon leverage AI to change enforcement.

Timestamps:
➡️ 00:00 — Intro

➡️ 01:18 — Sponsor: The Hedera Council

➡️ 01:23 — Crypto tax trends

➡️ 04:23 — Can offshore projects return onshore?

➡️ 05:12 — Common tax mistakes & how they could backfire

➡️ 11:31 — What happens if the IRS comes knocking

➡️ 13:55 — Major crypto tax developments under the new administration

➡️ 18:56 — Status of Lummis’ tax proposal and what might come next

➡️ 24:50 — Staking: why current proposals may not solve the problem

➡️ 31:11 — Airdrops: what upcoming legislation could get wrong

➡️ 36:30 — How the IRS might use AI and what that means for crypto traders

➡️ 42:24 — Why a mark-to-market election could provide needed clarity

➡️ 44:39 — Lending, wrapping, and other grey areas: what’s “reasonable”?

& more.

Sponsor: This episode is brought to you by the Hedera Council, the decentralized governing body for the Hedera network. They are currently hiring a Legal Counsel, and interested candidates can apply at https://hedera.com/future?gh_jid=4574329006. Be sure to tell them you heard of the position on the Law of Code podcast!

📬 Jason on Twitter: @CryptoTaxGuyETH

Disclaimer: Jacob Robinson and his guests are not your lawyer. Nothing herein or mentioned on the Law of Code podcast should be construed as legal advice. The material published is intended for informational, educational, and entertainment purposes only. Please seek the advice of counsel, and do not apply any of the generalized material to your individual facts or circumstances without speaking to an attorney.

SEC Commissioner Hester Peirce and Crypto Task Force Chief Counsel Mike Selig return to the podcast to share updates from the SEC’s Crypto Task Force — plus their thoughts on tokenized securities, market structure legislation, exemptive relief, and the role of decentralization in regulatory design.

Timestamps:

➡️ 00:00 — Intro

➡️ 00:46 — Sponsor: Day One Law

➡️ 01:09 — Tokenizing securities: what facts and circumstances matter

➡️ 02:51 — What exemptive relief could look like

➡️ 04:51 — Timeline for SEC action on tokenization

➡️ 05:14 — Key regulatory risks in tokenized markets

➡️ 07:44 — Could ZKPs enable on-chain compliance?

➡️ 09:55 — Will smart contract auditors exist at the SEC?

➡️ 10:38 — How decentralization fits into new frameworks

➡️ 15:27 — Best practices for speaking with the SEC

➡️ 17:38 — Pathways for offshore projects to re-engage in the U.S.

➡️ 18:45 — Passport regime vs. U.S.-specific compliance

➡️ 20:45 — What Crypto Task Force meetings actually look like

➡️ 22:09 — How the SEC views DePIN models and incentives

➡️ 23:40 — Could yield-bearing stablecoins become regulated products?

➡️ 24:54 — SEC–CFTC joint rulemaking: what’s next

& more.

Sponsor: This episode is brought to you by Day One Law — a boutique law firm helping crypto startups navigate complex legal challenges.

Resources:

📄 SEC Crypto Task Force information page

📬 Contact: [email protected]

📜 “Enchanting, but Not Magical: A Statement on the Tokenization of Securities” — Commissioner Peirce’s statement on tokenized securities.

Derivatives expert Katherine Kirkpatrick Bos, General Counsel of StarkWare, joins the podcast to discuss the first-ever CFTC-regulated "perpetual-style" futures contracts to occur onshore — a move that may pull trading volume back from offshore exchanges and reshape global market dynamics.

Prior to joining StarkWare, Katherine was Chief Legal Officer of Cboe Digital, a U.S. regulated exchange and clearinghouse for crypto spot and crypto derivatives markets.

Timestamps:

➡️ 00:00 — Intro
➡️ 00:53 — Sponsor: Day One Law
➡️ 01:27 — What are 'perps'?
➡️ 04:29 — Why have perps been offshore?
➡️ 07:48 — How are these new contracts CFTC-regulated?
➡️ 12:24 — Comparing regulated perps to offshore offerings
➡️ 15:56 — Benefits and protections for U.S. traders using onshore perps
➡️ 20:06 — Could this repatriate crypto volume to U.S.-regulated venues?
➡️ 24:48 — The future of crypto derivatives regulation: urgent areas needing clarity
& much more.

Sponsor: This episode is brought to you by Day One Law — a boutique law firm helping crypto startups navigate complex legal challenges. Visit ⁠⁠https://www.dayonelaw.xyz/⁠⁠ to get in touch.

Disclaimer: Jacob Robinson and his guests are not your lawyer. Nothing herein or mentioned on the Law of Code podcast should be construed as legal advice. The material published is intended for informational, educational, and entertainment purposes only. Please seek the advice of counsel, and do not apply any of the generalized material to your individual facts or circumstances without speaking to an attorney.

Stablecoins have grown from a total value of ~$2 billion in 2019 to over $230 billion by early 2025, enabling $33 trillion in transactions across 236 million wallets.

But beneath this growth lies a deep — and fragile — dependence on the U.S. Treasury market.

Professor Yesha Yadav of Vanderbilt Law School and Brendan Malone, formerly of Paradigm, the Federal Reserve Board, and MIT, discuss their paper on the critical but underexamined relationship between U.S. dollar stablecoins and Treasuries.

They unpack why Treasuries act as the “anchor” for stablecoins, explore operational and liquidity risks, and outline what policy changes might be necessary to avert a crisis.

Timestamps:

➡️ 00:00 — Intro

➡️ 01:10 — Sponsor: Hedera Council is hiring a legal counsel

➡️ 02:40 — Why is the U.S. Treasury market so critical to stablecoins?

➡️ 04:32 — Treasuries as “cash equivalents” and risk-free assets

➡️ 07:33 — What does it mean to “hold” Treasuries?

➡️ 11:38 — Liquidity and operational risks

➡️ 14:34 — Changing structure of Treasury markets

➡️ 16:12 — 24/7 crypto vs. limited-hour Treasury markets

➡️ 20:06 — Systemic risk scenarios

➡️ 28:27 — The urgent need for preemptive policy solutions

➡️ 33:22 — Regulatory fragmentation: “everyone’s responsible, so no one is”

➡️ 38:51 — Possible reforms: more short-term issuance, repo market, reserves access

➡️ 40:53 — Treasuries as “risk-free” assets — myth vs. reality

➡️ 46:23 — Potential Fed facilities and why they aren’t in place yet

➡️ 51:06 — Bonus: Hedera Council’s General Counsel Gregory Schneider on their open position.

Jessi Brooks is the General Counsel & Chief Compliance Officer at Ribbit Capital. Prior to Ribbit, Jessi was an attorney at the U.S. Department of Justice, where she worked on high-profile crypto and national security cases.

Jessi explains the blockchain tools used in the Bitfinex hack, why crypto > cash, how the DOJ works with stablecoin issuers, and much more.

The conversation also covers Jessi’s journey from prosecuting domestic violence cases to crypto, and her perspective on building bridges between regulators and the industry.

Timestamps:

➡️ 00:57 Lessons from the Bitfinex hack

➡️ 06:28 Unhosted wallets and the DOJ

➡️ 09:42 The role of seizure & forfeiture

➡️ 13:44 Increase in crypto-related cases

➡️ 19:18 Jessi’s early DOJ crypto cases

➡️ 23:23 Al-Qassam Brigades operation

➡️ 31:31 How DOJ and industry can align

➡️ 35:49 Her work at Ribbit Capital and advising startups

Sponsor: This episode is brought to you by Day One Law — a boutique law firm helping crypto startups navigate complex legal challenges. Visit ⁠https://www.dayonelaw.xyz/⁠ to get in touch.

#crypto #cryptocurrency #law #blockchain #bitcoin #ethereum

Disclaimer: Jacob Robinson and his guests are not your lawyer. Nothing herein or mentioned on the Law of Code podcast should be construed as legal advice. The material published is intended for informational, educational, and entertainment purposes only. Please seek the advice of counsel, and do not apply any of the generalized material to your individual facts or circumstances without speaking to an attorney.

What steps should founders and their counsel take when launching a token or product in web3?

In this episode, Jacob Robinson is joined by Nima Maleki (@Nimathefish), Counsel at Day One Law. Nima designs legal roadmaps for clients, including product counseling, token launches, and fundraising structures.

Nima shares what’s market for launching blockchain products — ranging from regulatory and decentralization strategies to token valuations, whether founders still need a foundation for their project, and where tax concerns may arise throughout the process.

Timestamps:
➡️ 00:00 – Intro
➡️ 01:03 – Sponsor: Day One Law
➡️ 01:32 – Agenda: Six Steps to Product / Token Launch
➡️ 04:10 – Questioning Decentralization Strategies
➡️ 06:57 – Step One: Structuring Your Business
➡️ 17:15 – Step Two: Fundraising
➡️ 24:51 – Step Three: Token Valuation
➡️ 28:48 – Step Four: Product / Token Launch

This episode is brought to you by Day One Law — a boutique law firm helping crypto startups navigate complex legal challenges.
Visit https://www.dayonelaw.xyz/ to get in touch.

#crypto #cryptocurrency #law #blockchain #bitcoin #ethereum

Disclaimer: Jacob Robinson and his guests are not your lawyer. Nothing herein or mentioned on the Law of Code podcast should be construed as legal advice. The material published is intended for informational, educational, and entertainment purposes only. Please seek the advice of counsel, and do not apply any of the generalized material to your individual facts or circumstances without speaking to an attorney.

In this episode, Jacob Robinson is joined by Justin Wales (@bitcoin_wales), Head of Legal (Americas) at Crypto.com and author of The Crypto Legal Handbook.

Sponsor: This episode is brought to you by Day One Law — a boutique law firm helping crypto startups navigate complex legal challenges. Visit https://www.dayonelaw.xyz/ to get in touch.

With the release of the book’s second edition, Justin shares what’s new: from stablecoin legislation and state-level licensing regimes to AI’s intersection with crypto and the shifting regulatory tone under a new administration. We also discuss how legal frameworks are evolving, the risks of regulatory whiplash, and why meme coins, AI agents, and decentralized settlement are at the center of today’s legal debates.

Timestamps:

➡️ 00:00 Intro

➡️ 00:46 Sponsor: Day One Law

➡️ 02:00 Second Edition Highlights & Historical Context

➡️ 04:00 State-Level Developments & Money Transmission Rules

➡️ 06:00 Outlook on Stablecoin and Market Structure Legislation

➡️ 08:00 How to Read the New Edition

➡️ 10:00 Operation Chokepoint, Debanking & Tax Updates

➡️ 11:30 The Rise of Meme Coins & Industry Disincentives

➡️ 14:30 SEC Enforcement, Risk Appetite & Innovation

➡️ 17:00 AI x Crypto: Communication, Trust & Open Protocols

➡️ 20:00 Crypto's Place in Financial Infrastructure

➡️ 22:30 Jurisdictional Competition & Market Pressure

➡️ 25:00 The Cost of Fitting Crypto Into Legacy Systems

➡️ 27:00 Global Posture Shift & Optimism for the Future

➡️ 29:00 Final Thoughts

The Crypto Legal Handbook: You can find it online for $30, here: https://thecryptolegalhandbook.com/

Disclaimer: Jacob Robinson and his guests are not your lawyer. Nothing herein or mentioned on the Law of Code podcast should be construed as legal advice. The material published is intended for informational, educational, and entertainment purposes only. Please seek the advice of counsel, and do not apply any of the generalized material to your individual facts or circumstances without speaking to an attorney.

If the law were truly “technology-neutral,” what would that look like in practice for a P2P securities transaction via smart contracts?

In this episode, Jacob Robinson is joined by Tuongvy Le (@TuongvyLe12), who has served as General Counsel of Anchorage Digital, Partner and Head of Regulatory and Policy at Bain Capital Crypto, and Deputy GC and Compliance Officer at Worldcoin. She also spent almost six years at the SEC as Senior Counsel in the Division of Enforcement and Chief Counsel of the Legislative and Intergovernmental Affairs Office.

Together, they discuss her recent Fortune article on why the SEC needs to take a hands-off approach to peer-to-peer transactions (link) and market structure history and regulation (link).

Timestamps:
➡️ 00:00 Intro
➡️ 0:46 Sponsor: Day One Law
➡️ 03:43 Peer-to-Peer Transactions: Analog vs. Digital
➡️ 06:36 The Intersection of DeFi and Securities Law
➡️ 12:40 Industry Self-Regulation and Best Practices
➡️ 15:40 Understanding Market Structure: A Historical Context
➡️ 24:31 Designing a New Market Structure for Crypto
➡️ 32:25 The SEC's Evolving Stance on Crypto Innovation

This episode is brought to you by Day One Law — a boutique law firm helping crypto startups navigate complex legal challenges. Visit https://www.dayonelaw.xyz/ to get in touch.

Disclaimer: Jacob Robinson and his guests are not your lawyer. Nothing herein or mentioned on the Law of Code podcast should be construed as legal advice. The material published is intended for informational, educational, and entertainment purposes only. Please seek the advice of counsel, and do not apply any of the generalized material to your individual facts or circumstances without speaking to an attorney.

In this episode, Jacob Robinson is joined by Dr. Chris Brummer (@ChrisBrummerDr), Professor of Financial Technology at Georgetown Law and Founder & CEO of Bluprynt, an AI and blockchain-powered platform for automating regulatory disclosures.

Together, they unpack the SEC’s recent statement: Offerings and Registrations of Securities in the Crypto Asset Markets — a document that some say could mark a paradigmatic shift in the agency’s approach to digital asset regulation. We also discuss his article on this guidance.

Timestamps:

➡️ 00:00 Intro

➡️ 0:46 Sponsor: Day One Law

➡️ 01:37 What is Bluprynt?

➡️ 07:32 Why this SEC guidance is timely and valuable

➡️ 09:41 The SEC is paying down regulatory debt

➡️ 16:03 Smart contract disclosures

➡️ 18:40 The investment contract question

➡️ 21:25 How projects can navigate this paradigm shift

This episode is brought to you by Day One Law — a boutique law firm helping crypto startups navigate complex legal challenges. Visit https://www.dayonelaw.xyz/ to get in touch.

Disclaimer: Jacob Robinson and his guests are not your lawyer. Nothing herein or mentioned on the Law of Code podcast should be construed as legal advice. The material published is intended for informational, educational, and entertainment purposes only. Please seek the advice of counsel, and do not apply any of the generalized material to your individual facts or circumstances without speaking to an attorney.

In this conversation, Jacob Robinson and Amanda Tuminelli, Executive Director of the DeFi Education Fund, delve into the criminal code provision punishing unlicensed money transmitting businesses, why this is relevant for developers of non-custodial crypto projects, and how a recent memo from the Department of Justice on ending “the regulatory weaponization against digital assets" might not have gone far enough.

Timestamps:

➡️ 00:00 Intro

➡️ 0:46 Sponsor: Day One Law

➡️ 01:05 What is Section 1960 and how does it impact crypto developers

➡️ 03:42 What case law tells us about Section 1960

➡️ 06:11 How money transmitting and money service businesses are defined

➡️ 09:14 The DOJ's memo on ending regulation by enforcement against crypto

➡️ 13:40 The charge at the heart of the Tornado Cash and Samurai Wallet cases

➡️ 18:48 Tornado Cash sanctions and OFAC's delisting: Not exactly as advertised

The DeFi Education Fund is hiring! You can learn more about their open positions here: https://www.defieducationfund.org/jobs-internships

This episode of the Law of Code podcast is brought to you by Day One Law — a boutique corporate law firm founded by recurring guest (and friend of the show) Nick Pullman. Nick and his team at Day One provide strategic legal counsel to startups, crypto projects, and Web3 innovators. Visit https://www.dayonelaw.xyz/ get in touch.

Disclaimer: Jacob Robinson and his guests are not your lawyer. Nothing herein or mentioned on the Law of Code podcast should be construed as legal advice. The material published is intended for informational, educational, and entertainment purposes only. Please seek the advice of counsel, and do not apply any of the generalized material to your individual facts or circumstances without speaking to an attorney.