Can prediction markets coexist with traditional sportsbooks and financial platforms?

Dustin Gouker is a journalist and consultant covering sports betting and prediction markets. He publishes the newsletters The Closing Line and The Event Horizon, where he tracks the rapidly evolving intersection of gambling, finance, and event-based trading.

Timestamps

➡️ 1:15 — How prediction markets re-emerged after the 2024 election and Kalshi court ruling
➡️ 3:33 — The Super Bowl “Cardi B performed” market controversy
➡️ 6:25 — Why vague market rules create settlement disputes
➡️ 7:34 — The financialization and “gamblification” of everyday events
➡️ 10:23 — Insider trading concerns in prediction markets
➡️ 12:41 — DraftKings acquiring a CFTC-regulated exchange and the sportsbook response
➡️ 17:00 — Why prediction market volume numbers are often misunderstood
➡️ 20:18 — The coming clash between sportsbooks and prediction market platforms
➡️ 27:18 — Are prediction markets really “truth machines”?
➡️ 33:33 — The risks of speculation and the future of event-based trading

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 Closing Line

✉️ The Event Horizon

✉️ Dustin's newsletter on DraftKings' acquisition of Railbird

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 were the most important legal and regulatory developments in crypto this month? In this episode, we review developments from stablecoin rulemaking and DeFi liability cases to the ongoing fight over prediction markets.

Jonathan Schmalfeld is Director of Policy at The Digital Chamber, where he focuses on crypto policy, digital asset legislation, and regulatory developments in Washington.

Timestamps

➡️ 1:07 — SEC guidance allowing broker-dealers to apply a 2% capital haircut to payment stablecoins
➡️ 4:37 — OCC’s GENIUS Act implementation proposal and the debate over stablecoin yield restrictions
➡️ 11:14 — The Promoting Innovation and Blockchain Development Act and developer liability protections
➡️ 17:27 — Federal court dismissal of claims against Uniswap and what it means for DeFi developers
➡️ 22:55 — How Kalshi enforced insider trading rules in its CFTC-regulated prediction markets
➡️ 27:37 — Kalshi’s preliminary injunction against Tennessee regulators and the federal preemption fight
➡️ 31:15 — Why prediction market litigation could eventually reach the U.S. Supreme Court
➡️ 36:25 — Institutional adoption: Morgan Stanley custody plans, Kraken’s Fed master account, and crypto banking licenses
➡️ 40:24 — Operation Chokepoint 2.0 and proposed rules eliminating “reputational risk” in bank supervision
➡️ 43:23 — Why competition between crypto and traditional finance is accelerating

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:

📃 Updated SEC Division of Trading & Markets FAQ

✍️ Hester Peirce statement on updated SEC FAQ

📃 OCC Notice of proposed rulemaking for implementation of the GENIUS Act

📓 Promoting Innovation in Blockchain Development Act of 2026

📃 Kansas City Fed statement on Kraken’s fed master account

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 happens when a crypto policy lawyer decides to run for one of the most powerful regulatory positions in the United States — New York Attorney General?

Khurram Dara is a former policy team member at Coinbase and regulatory policy principal at Bain Capital Crypto. After years working in crypto regulation and policy, he left the private sector to run for the Republican nomination for Attorney General of New York, focusing his campaign on reversing lawfare, regulatory overreach, and using the role of New York Attorney general to shape national policy.

Timestamps

➡️ 1:24 — Coinbase, the SEC, and why regulation-by-enforcement pushed Dara toward politics
➡️ 4:13 — Why state attorneys general have become “regulators of last resort”
➡️ 9:30 — Running for office without prior political experience
➡️ 11:31 — How statewide campaigns actually start: conventions, delegates, and ballot access
➡️ 17:02 — Campaign execution: fundraising, messaging, and building a political operation
➡️ 24:27 — What Dara learned about fundraising and donor dynamics
➡️ 28:08 — What “lawfare” means and why it concerns the crypto industry
➡️ 33:08 — The economic impact of regulation through litigation
➡️ 37:40 — How state AG offices could be reformed
➡️ 45:45 — Why state-level crypto regulation may be the next battleground

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 Dismissal of Civil Enforcement Against Coinbase
📄 Press release for Attorney General James’ lawsuit against Trump family financial business

📄 Press release for Oregon lawsuit against Coinbase

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.

If blockchain systems can automatically enforce transactions, does that mean code itself determines legal rights and ownership?

Carla Reyes and Andrea Tosato are professors researching digital assets at the SMU Dedman School of Law and Andrew Hinkes is a partner at Winston & Strawn LLP. Together they authored the paper “Code Is Not Law,” which examines why legal rights in digital assets ultimately depend on law rather than technological systems.

Time Stamps:

➡️ 1:30 — Stablecoin yield debates and why banks are back at the negotiating table
➡️ 4:24 — Trade associations vs. decision-makers in White House crypto meetings
➡️ 7:43 — Ethics provisions and constitutional challenges shaping negotiations
➡️ 12:48 — Network token frameworks, ancillary assets, and draft bill trends
➡️ 14:38 — DeFi intermediaries: software providers vs. financial actors
➡️ 17:44 — Disclosure quality vs. disclosure volume in market structure drafts
➡️ 21:38 — Legislation vs. agency guidance vs. litigation: three regulatory paths
➡️ 24:30 — What retail users would actually notice if market structure passes
➡️ 30:08 — Global competition: MiCA, Singapore MAS, and U.S. brain drain risk
➡️ 43:51 — Regulatory moats, incumbents, and the future of innovation

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: 

📓 "Code is not law" research paper

🎧 Episode #75 -  UCC Article 12 Amendments with Drew Hinkes and Andrea Tosato

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 role are ethics provisions and stablecoin yield debates, playing in shaping — or potentially delaying — U.S. crypto market structure legislation?

Gerald Gallagher is General Counsel at Sei Labs and co-host of the Crypto in America podcast, where he covers crypto policy, regulation, and legal developments in Washington.

Timestamps:

➡️ 1:30 — Stablecoin yield debates and why banks are back at the negotiating table
➡️ 4:24 — Trade associations vs. decision-makers in White House crypto meetings
➡️ 7:43 — Ethics provisions and constitutional challenges shaping negotiations
➡️ 12:48 — Network token frameworks, ancillary assets, and draft bill trends
➡️ 14:38 — DeFi intermediaries: software providers vs. financial actors
➡️ 17:44 — Disclosure quality vs. disclosure volume in market structure drafts
➡️ 21:38 — Legislation vs. agency guidance vs. litigation: three regulatory paths
➡️ 24:30 — What retail users would actually notice if market structure passes
➡️ 30:08 — Global competition: MiCA, Singapore MAS, and U.S. brain drain risk
➡️ 43:51 — Regulatory moats, incumbents, and the future of innovation

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 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.

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.