The Chopping Block: Paul Grewal on Regulation, Tokenization, and Crypto’s Next Legal Frontier – Ep 867
Unchained11 Heinä

The Chopping Block: Paul Grewal on Regulation, Tokenization, and Crypto’s Next Legal Frontier – Ep 867

Welcome to The Chopping Block – where crypto insiders Haseeb Qureshi, Tom Schmidt, Tarun Chitra, and Robert Leshner chop it up about the latest in crypto. In this episode, the gang is joined by Paul Grewal, Chief Legal Officer at Coinbase, for a wide-ranging conversation on crypto’s next big frontier: tokenized stocks. From Robinhood’s controversial attempt to tokenize SpaceX and OpenAI shares to the legal and structural hurdles around pre-IPO derivatives, the crew dives deep into what it really takes to bring Wall Street on-chain. They also unpack the regulatory momentum behind the Genius and Clarity Acts, the return of ICO mania with Pump.fun’s $1B token raise, and the absurdly viral drama of Suitgate on Polymarket. Is this a new era of regulated innovation—or are we just recreating old problems on new rails? Tune in for sharp takes, legal insight, and a few laughs along the way. Show highlights 🔹 Tokenized Stocks Take Center Stage – Robinhood, SoFi, and Republic dive into pre-IPO trading; is this a financial revolution or regulatory chaos? 🔹 Coinbase’s Legal Strategy – Paul Grewal reflects on Coinbase’s battles with the SEC and what it took to survive crypto’s darkest legal hour 🔹 Pre-IPO Derivatives vs. Real Ownership – The crew debates whether retail is getting access or getting played 🔹 Robinhood vs. OpenAI – The tokenized equity stunt that triggered a corporate backlash and raised eyebrows across the industry 🔹 24/7 Markets, Finally? – Why crypto-native trading hours could break traditional finance 🔹 Pump.fun’s $1B ICO – The return of ICO mania? The team dissects crypto’s most profitable meme machine 🔹 Are Tokenized Stocks Useful Yet? – Tarun challenges the hype: where’s the real utility? 🔹 The Clarity & Genius Acts – Crypto legislation heats up in Washington—can the industry lock in meaningful reform? 🔹 Suitgate Explained – Zelensky’s outfit spawns a scandal on Polymarket: was it a suit or not? 🔹 Market Manipulation, Oracles & Meme Justice – Prediction markets meet internet chaos in the wildest crypto dispute of the week ⭐️Haseeb Qureshi, Managing Partner at Dragonfly ⭐️Robert Leshner, CEO & Co-founder of Superstate⭐️Tarun Chitra, Managing Partner at Robot Ventures⭐️Tom Schmidt, General Partner at Dragonfly Special Guest ⭐️Paul Grewal, Chief Legal Officer at Coinbase Timestamps 00:00 Intro feat. Paul Grewal 01:23 How Coinbase Beat the SEC 04:49 Robinhood, OpenAI & the Pre-IPO Stock Craze 19:38 Crypto Regulation in 2025: Clarity & Genius Act 24:39 Why the Clarity Act Could Define Crypto’s Next Decade 27:10 Pump.fun’s ICO: Memecoin Mania or Market Maturity? 32:25 Suitgate on Polymarket: A Wild Crypto Scandal 39:19 The Future of Prediction Markets Disclosures Learn more about your ad choices. Visit megaphone.fm/adchoices

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Why The First Employee Of Coinbase Launched A Hedge Fund

Why The First Employee Of Coinbase Launched A Hedge Fund

Olaf Carlson-Wee is the founder of Polychain Capital, a hedge fund that has invested $15 million into digital assets and has gotten backing from storied venture capital firms Andreessen Horowitz and Union Square Ventures. In this episode, Carlson-Wee recounts war stories from the early days of bitcoin, including how he learned about bitcoin before his computer science professors, bought bitcoins with cash and created “the Bitcoin SAT” to make hires at Coinbase. He also describes how to separate cryptocurrency scams from legitimate ventures, how he plays blackjack against a smart contract and why launching a digital asset hedge fund means he can no longer earn and spend mostly in bitcoin. Read the show notes.  Other links: Polychain Capital Coinbase Golem Tezos This episode was sponsored by Onramp. Learn more about your ad choices. Visit megaphone.fm/adchoices

7 Maalis 201757min

Why Nasdaq Is Even More Optimistic About Blockchain Than It Was 3 Years Ago

Why Nasdaq Is Even More Optimistic About Blockchain Than It Was 3 Years Ago

Fredrik Voss, Nasdaq's head of blockchain initiatives, discusses what the company has accomplished with the technology and how his firm evaluates whether potential projects could benefit from a blockchain solution. He also reveals what is likely to really slow adoption of distributed ledgers (hint: not the tech itself) and gives advice to other companies looking to incorporate it. Read the show notes and my magazine story on Chain and its work with Nasdaq.  This episode was sponsored by Onramp. Learn more about your ad choices. Visit megaphone.fm/adchoices

21 Helmi 201750min

With Deadline Looming, Will The SEC Approve A Bitcoin ETF?

With Deadline Looming, Will The SEC Approve A Bitcoin ETF?

The SEC will make a decision on a proposed bitcoin ETF by March 11. Will it approve? An optimist and pessimist weigh in, touching upon bitcoin’s liquidity, the impact recent events in China have had on its trading, as well as proposals for bitcoin ETFs by other companies. Plus, they reveal what impact an ETF could have on the bitcoin market. Read the show notes. Other links:  Needham & Company Global Advisors Gemini This episode was sponsored by Onramp.   Learn more about your ad choices. Visit megaphone.fm/adchoices

7 Helmi 201757min

Is The IRS Justified In Demanding Information On Millions Of Bitcoin Users?

Is The IRS Justified In Demanding Information On Millions Of Bitcoin Users?

The IRS found three entities using bitcoin to evade taxes and has now demanded the records of millions of users at Coinbase, the largest U.S. cryptocurrency exchange. An accountant and an attorney specializing in cryptocurrency discuss whether the IRS is overreaching, how this "unprecedented" case differs from previous ones pursued by the IRS, and what they think the ultimate outcome will be. Read the show notes. Other links: Coinbase Berns Weiss LLP Global Tax Accountants Brian Armstrong's response on Medium My magazine feature on Coinbase This episode was sponsored by Onramp. Learn more about your ad choices. Visit megaphone.fm/adchoices

24 Tammi 201751min

What Is One Of The World's Largest Derivatives Exchanges Doing With Bitcoin?

What Is One Of The World's Largest Derivatives Exchanges Doing With Bitcoin?

CME Group handles three billion contracts worth about $1 quadrillion annually. So why is it making a foray into bitcoin, whose market capitalization is a mere $16 billion? Sandra Ro, CME's head of digitization, explains its first cryptocurrency products, the Bitcoin Reference Rate and the Bitcoin Real-Time Index, as well as a forthcoming blockchain-based product, Royal Mint Gold. She also reveals which other cryptocurrencies have piqued her interest and which other physical world assets she thinks could be traded by blockchain.   Read the show notes.   Other links: CME's Bitcoin Reference Rate Bitcoin Real-Time Index Royal Mint Gold Learn more about your ad choices. Visit megaphone.fm/adchoices

10 Tammi 201745min

Federal Prosecutor Kathryn Haun On How Criminals Use Bitcoin -- And How She Catches Them

Federal Prosecutor Kathryn Haun On How Criminals Use Bitcoin -- And How She Catches Them

Kathryn Haun put away the DEA and Secret Service agents who tried to make off with more than $800,000 in stolen bitcoin while investigating the darknet Silk Road marketplace. She talks about how the blockchain technology underlying Bitcoin made it possible to uncover their theft, why she believes blockchain will create a lot of good, and what she does when the very people behind tumblers and mixers -- technology that makes her work more difficult -- turn to her when they are the victims of crimes. Along the way, we learn about the habits of cryptocurrency criminals and get a fascinating view into the world of "breeder documents." Learn more about your ad choices. Visit megaphone.fm/adchoices

1 Marras 201645min

How Coin Center Is Helping Define The 'Big Fuzzy Gray Area' Of Blockchain And Cryptocurrency Law

How Coin Center Is Helping Define The 'Big Fuzzy Gray Area' Of Blockchain And Cryptocurrency Law

As blockchains and cryptocurrencies evolve, there are times when the technology outpaces the law. That's when Coin Center steps in. The non-profit, which represents the technology, not the industry, and aims for regulators to keep a mostly hands-off attitude, has already helped shape questions around which types of Bitcoin wallet providers are financial institutions and whether new coins being offered represent securities. And answering these questions has drawn it back into previous cases involving everything from Florida orange groves to Manhattan co-ops to golf club memberships. Learn more about your ad choices. Visit megaphone.fm/adchoices

18 Loka 201650min

What Does Cornell’s Emin Gun Sirer See As The Main Security Threats In Cryptocurrency? ‘Everything’

What Does Cornell’s Emin Gun Sirer See As The Main Security Threats In Cryptocurrency? ‘Everything’

Cornell University computer science professor Emin Gun Sirer, an influential figure in the cryptocurrency and blockchain space, describes his ideas for improving security in the space, his skepticism about how to scale these networks, and how the last time financial institutions invested in their systems appears to be for Y2K. He also tells us how growing up in an environment where he saw a lot of scams helps him find problems in code, explains why Bitcoin is the “universal bug bounty,” and reveals how two high school students saved burgeoning cryptocurrency network Ethereum “like in the movies — just before the clock was going to expire.” Learn more about your ad choices. Visit megaphone.fm/adchoices

4 Loka 201657min

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