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The Rollup

The Rollup

Where digital assets meet capital markets. Hosted by Robbie & Andy 646 Episodes Sep 19, 2026

The Rollup is a podcast where leaders in digital assets and finance converge, hosted by Robbie and Andy. It covers topics at the intersection of digital assets and capital markets, featuring interviews and discussions with industry experts. The show is broadcast live from the financial capital of the world, New York City.

Episodes

Kevin O'Leary: Crypto Becomes The 12th Sector Of The S&P (Full Thesis)
Kevin O'Leary: Crypto Becomes The 12th Sector Of The S&P (Full Thesis) Sep 19, 2026 00:12:42 Kevin O’Leary joins us in NYC for an interview about his allocation and views on the digital asset market.Digital assets becoming the twelfth sector of the S&P was his core framing. He thinks it gets there by servicing the other eleven. He also walks back a position he held eighteen months ago: that everything would standardize on Ethereum. Now he expects sectors to pick their own chains, and
Circle CEO: The Entire Financial System Is Coming Onchain (We’re Still Early)
Circle CEO: The Entire Financial System Is Coming Onchain (We’re Still Early) Sep 18, 2026 00:14:52 Jeremy Allaire joins us from the Arc mainnet launch event in NYC this week to discuss the explosive growth ahead of agentic finance.Mobile existed for fifteen years before iOS and Android made it actually work. Jeremy Allaire thinks blockchains just hit the same moment. On Arc's launch day, he lays out why Circle built a network operating system rather than another chain, and how the agentic e
Will Peck: How WisdomTree Went From $30M To Over $1 Billion Onchain (Full Breakdown)
Will Peck: How WisdomTree Went From $30M To Over $1 Billion Onchain (Full Breakdown) Sep 16, 2026 00:34:39 WisdomTree's Head of Digital Asset's Will Peck joins us for Episode #1 of Convergence, our new institutional product for sophisticated investors in partnership with Jacquelyn Melinek and StrataMedia.WisdomTree's onchain assets went from $30 million to over $1 billion, and Will Peck says money market funds did the heavy lifting. On episode one of Convergence, Will explains why tokenized
CMS Holdings: The Next Bull Market Is Upon Us (How To Position For Success)
CMS Holdings: The Next Bull Market Is Upon Us (How To Position For Success) Sep 15, 2026 00:40:06 CMS Holdings operator Dan joins us for a conversation about positioning for the next bull market.Tokenized equities end up bigger than stablecoins, and Dan Matuszewski thinks most people have the reason wrong. It isn't about 24/7 trading or DeFi composability. It's that an enormous share of the world wants to own Nvidia and structurally can't, exactly the gap Tether filled for dollars.
Sam Kazemian & Raagulan Pathy: Why Neo Banks Are Quietly Selling Themselves (Full Interview)
Sam Kazemian & Raagulan Pathy: Why Neo Banks Are Quietly Selling Themselves (Full Interview) Sep 13, 2026 00:35:14 Raagulan Pathy says KAST becomes a $100 billion company or it fails outright. There's no in-between, and he explains exactly why on this episode. The KAST founder and Frax's Sam Hamidi-Kazemian debate what's actually driving the neo bank and stablecoin boom, why regulators are starting to treat stablecoins as a national priority, and whether brand, network effects, or raw economies of
John Gillen: Ethereum Will Fly From Here And Most Investors Aren't Ready (Here's Why)
John Gillen: Ethereum Will Fly From Here And Most Investors Aren't Ready (Here's Why) Sep 12, 2026 00:22:20 John Gillen says Ethereum could hit $4,000 before the end of the year, and he's been making that case in a viral essay series called Wartime Ethereum. The ex-BlackRock analyst and Milk Road Daily Show host breaks down why tokenization and stablecoins are converging on ETH, why he thinks Wall Street is about to adopt it as its new favorite asset, and who he believes the next wave of buyers actu
Felix Jauvin: Why The Fiat Debasement Trade Is Set To Explode Soon (Full Portfolio Construction)
Felix Jauvin: Why The Fiat Debasement Trade Is Set To Explode Soon (Full Portfolio Construction) Sep 10, 2026 00:43:04 Felix Jauvin says he's as bullish as he ever has been on digital assets and thinks the bottom is in.He's also been quietly rotating Bitcoin into Zcash and he lays out exactly why. The Blockworks Head of Content walks through the SEC's new tokenization exemption, why he thinks 75% of crypto tokens still have no real claim on value, his read on whether the Fed hikes in September. He expl
Dan Held: SpaceX Will Hit $100 Trillion Market Cap In 20 Years (The Detailed Thesis)
Dan Held: SpaceX Will Hit $100 Trillion Market Cap In 20 Years (The Detailed Thesis) Sep 9, 2026 00:41:54 Dan Held joins us to unpack what it means to become a generational investor in today's world. For reference, he bought Bitcoin in 2012 and recently sold a lot to pour it into SpaceX, and says the thesis has barely started. The longtime Bitcoin investor lays out why Starship's collapsing launch costs could unlock a total addressable market bigger than global GDP, why he thinks this cycle ju
Arthur Hayes: Ethereum Will Outperform The Entire Market (It’s My Biggest Position)
Arthur Hayes: Ethereum Will Outperform The Entire Market (It’s My Biggest Position) Sep 7, 2026 00:41:27 Arthur Hayes joins us for a session to understand the underlying economic forces leading to a massive digital assets bull market in the coming months and years.The money printer is about to flip back on and Arthur Hayes says the Euro/Yen exchange rate is the tell everyone's missing. He gets into why Japan's forced unwinding of its massive carry trade, combined with France's brewing bon
Jake Chervinsky: Hyperliquid Is Set To Enter The US Market Imminently (Necessary Steps Explained)
Jake Chervinsky: Hyperliquid Is Set To Enter The US Market Imminently (Necessary Steps Explained) Sep 7, 2026 00:43:42 Jake Chervinsky joins us in the Tokenization Tower to explain the path for Hyperliquid to enter the US markets.Trump said "Hyperliquid" on national television and Jake Chervinsky was there to watch it happen live. He explains why perpetual futures are already coming to the US through the CFTC, why Hyperliquid is infrastructure rather than a competitor to exchanges like Coinbase and CME,
SEC Crypto Chief Counsel: Robinhood Stock Tokens Are Just The Beginning (Our Pro-Innovation Mindset)
SEC Crypto Chief Counsel: Robinhood Stock Tokens Are Just The Beginning (Our Pro-Innovation Mindset) Sep 6, 2026 00:28:56 Taylor Lindman calls in during a pivotal moment of Robinhood Chain stock token mania to debrief us on how the SEC is approaching tokenization.He explains how Reg Crypto could be the biggest shakeup to token fundraising since the JOBS Act and Taylor Lindman just laid out exactly how it works. She breaks down why tokenized "stock tokens" from Robinhood and others are legally structured more like deb
Ryan Watkins: Hyperliquid Will Dominate Global Finance (It’s Coming To USA)
Ryan Watkins: Hyperliquid Will Dominate Global Finance (It’s Coming To USA) Sep 5, 2026 00:34:53 Ryan Watkins joins the show for an updated view on the digital assets bull marketAre traders are about to become bigger celebrities than athletes? Well, maybe or maybe not.He breaks down why Hyperliquid's real endgame was always taking share from Binance and Coinbase, not just onchain rivals, and makes the case that barbell portfolio of store-of-value assets and revenue-generating businesses i

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