Matt and Nic are back with more news and deals. In this episode: <ul> <li>CIV grows the team</li> <li>Nic does not regret 8 years in crypto</li> <li>People are getting blackpilled about crypto</li> <li>Does speculation in crypto have positive externalities?</li> <li>Matt has never seen LOTR</li> <li>Will web3 ever come back?</li> <li>The OCC lets banks broker crypto trades</li> <li>The Bitwise 10 lists</li> <li>Rushi Manche returns with a fund</li> <li>Circle is launching a private stablecoin</li> <li>The DTC gets a no action letter from the SEC to settle tokenized securities</li> <li>We do a Terra/Luna restrospective</li> <li>Terra's fatal mistake</li> <li>Oracle mishaps on prediction markets</li> <li>Why did the nation's largest teachers union come out against the Market Structure bill</li> </ul> Content mentioned in this episode: <ul> <li>Nic Carter and Allen Farrington, <a href= "https://niccarter.info/wp-content/uploads/All-Falls-Down-Whitepaper-2022-06-11.pdf"> All Falls Down</a></li> </ul>

<description>&lt;p&gt;Matt and Nic are back with more news and deals. In this episode: &lt;/p&gt; &lt;ul&gt; &lt;li&gt;CIV grows the team&lt;/li&gt; &lt;li&gt;Nic does not regret 8 years in crypto&lt;/li&gt; &lt;li&gt;People are getting blackpilled about crypto&lt;/li&gt; &lt;li&gt;Does speculation in crypto have positive externalities?&lt;/li&gt; &lt;li&gt;Matt has never seen LOTR&lt;/li&gt; &lt;li&gt;Will web3 ever come back?&lt;/li&gt; &lt;li&gt;The OCC lets banks broker crypto trades&lt;/li&gt; &lt;li&gt;The Bitwise 10 lists&lt;/li&gt; &lt;li&gt;Rushi Manche returns with a fund&lt;/li&gt; &lt;li&gt;Circle is launching a private stablecoin&lt;/li&gt; &lt;li&gt;The DTC gets a no action letter from the SEC to settle tokenized securities&lt;/li&gt; &lt;li&gt;We do a Terra/Luna restrospective&lt;/li&gt; &lt;li&gt;Terra's fatal mistake&lt;/li&gt; &lt;li&gt;Oracle mishaps on prediction markets&lt;/li&gt; &lt;li&gt;Why did the nation's largest teachers union come out against the Market Structure bill&lt;/li&gt; &lt;/ul&gt; &lt;p&gt;Content mentioned in this episode:&lt;/p&gt; &lt;ul&gt; &lt;li&gt;Nic Carter and Allen Farrington, &lt;a href= "https://niccarter.info/wp-content/uploads/All-Falls-Down-Whitepaper-2022-06-11.pdf"&gt; All Falls Down&lt;/a&gt;&lt;/li&gt; &lt;/ul&gt; &lt;p&gt; &lt;/p&gt;</description>

Weekly Roundup 12/12/25 (Do Kwon sentenced, DTC no action letter, Circle's private stablecoin) (EP.690)

Matt and Nic are back with another week of news and deals. In this episode: <ul> <li>Quantum risk again</li> <li>Are banks filled with spooks?</li> <li>The trouble with Taproot addresses</li> <li>Microstrategy's dollar reserve</li> <li>Kalshi is going on chain</li> <li>Prediction market predicaments</li> <li>Are insiders monetizing Google search information on Polymarket?</li> <li>Are prediction markets insider trading machines by definition?</li> <li>DAT activist fights</li> <li>Vanguard adds Bitcoin ETFs</li> <li>House Financial Services Committee releases their final report on OCP2.0</li> <li>What's going on with leverage in crypto?</li> <li>Are AI agents going to start stealing crypto?</li> <li>Is Eliezer Yudkowski to be trusted?</li> <li>AI is going to usher in the golden age of fraud</li> </ul>

<description>&lt;p&gt;Matt and Nic are back with another week of news and deals. In this episode: &lt;/p&gt; &lt;ul&gt; &lt;li&gt;Quantum risk again&lt;/li&gt; &lt;li&gt;Are banks filled with spooks?&lt;/li&gt; &lt;li&gt;The trouble with Taproot addresses&lt;/li&gt; &lt;li&gt;Microstrategy's dollar reserve&lt;/li&gt; &lt;li&gt;Kalshi is going on chain&lt;/li&gt; &lt;li&gt;Prediction market predicaments&lt;/li&gt; &lt;li&gt;Are insiders monetizing Google search information on Polymarket?&lt;/li&gt; &lt;li&gt;Are prediction markets insider trading machines by definition?&lt;/li&gt; &lt;li&gt;DAT activist fights&lt;/li&gt; &lt;li&gt;Vanguard adds Bitcoin ETFs&lt;/li&gt; &lt;li&gt;House Financial Services Committee releases their final report on OCP2.0&lt;/li&gt; &lt;li&gt;What's going on with leverage in crypto?&lt;/li&gt; &lt;li&gt;Are AI agents going to start stealing crypto?&lt;/li&gt; &lt;li&gt;Is Eliezer Yudkowski to be trusted?&lt;/li&gt; &lt;li&gt;AI is going to usher in the golden age of fraud&lt;/li&gt; &lt;/ul&gt;</description>

Weekly Roundup 12/05/25 (The trouble with Taproot, a prediction market paradox, HFSC OCP.2 report) (EP.689)

<a href= "https://x.com/SimkinStepan?ref_src=twsrc%5Egoogle%7Ctwcamp%5Eserp%7Ctwgr%5Eauthor"> Stepan</a>, founder of <a href="https://squads.xyz/">Squads</a>, sits down with Wyatt on today's episode. In this discussion: <ul> <li>Squads' evolution from a DeFi-facing product to servicing a broader range of companies' asset treasury needs.</li> <li>What are the pain points of local small-medium businesses?</li> <li>What is driving the gradual global movement from local currencies into USD stablecoins?</li> <li>The appetite for safe yield across user types.</li> <li>Other traditional digital banking players and how they are evolving with technology.</li> <li>How the stablecoin trend impacts governments.</li> <li>What happens to local banks?</li> </ul>

<description>&lt;p&gt;&lt;a href= "https://x.com/SimkinStepan?ref_src=twsrc%5Egoogle%7Ctwcamp%5Eserp%7Ctwgr%5Eauthor"&gt; Stepan&lt;/a&gt;, founder of &lt;a href="https://squads.xyz/"&gt;Squads&lt;/a&gt;, sits down with Wyatt on today's episode. In this discussion:&lt;/p&gt; &lt;ul&gt; &lt;li&gt;Squads' evolution from a DeFi-facing product to servicing a broader range of companies' asset treasury needs.&lt;/li&gt; &lt;li&gt;What are the pain points of local small-medium businesses?&lt;/li&gt; &lt;li&gt;What is driving the gradual global movement from local currencies into USD stablecoins?&lt;/li&gt; &lt;li&gt;The appetite for safe yield across user types.&lt;/li&gt; &lt;li&gt;Other traditional digital banking players and how they are evolving with technology.&lt;/li&gt; &lt;li&gt;How the stablecoin trend impacts governments.&lt;/li&gt; &lt;li&gt;What happens to local banks?&lt;/li&gt; &lt;/ul&gt;</description>

Stepan Simkin (Squads) on Stablecoin-Powered Financial Services (EP.688)

Matt and Nic record a special Thanksgiving episode of OTB. In this episode: <ul> <li>What's the deal with deep fried turkeys?</li> <li>Polymarket gets CTFC approval</li> <li>Klarna is launching a stablecoin on Tempo</li> <li>Upbit is hacked</li> <li>Berachain drama</li> <li>Tether gets a downgrade from S&P</li> <li>Robinhood is spinning up their own prediction market with Susquehanna</li> <li>Are Visa and Mastercard moving fast enough?</li> <li>Who are we thankful for?</li> </ul>

<description>&lt;p&gt;Matt and Nic record a special Thanksgiving episode of OTB. In this episode: &lt;/p&gt; &lt;ul&gt; &lt;li&gt;What's the deal with deep fried turkeys?&lt;/li&gt; &lt;li&gt;Polymarket gets CTFC approval&lt;/li&gt; &lt;li&gt;Klarna is launching a stablecoin on Tempo&lt;/li&gt; &lt;li&gt;Upbit is hacked&lt;/li&gt; &lt;li&gt;Berachain drama&lt;/li&gt; &lt;li&gt;Tether gets a downgrade from S&amp;P&lt;/li&gt; &lt;li&gt;Robinhood is spinning up their own prediction market with Susquehanna&lt;/li&gt; &lt;li&gt;Are Visa and Mastercard moving fast enough?&lt;/li&gt; &lt;li&gt;Who are we thankful for?&lt;/li&gt; &lt;/ul&gt;</description>

Weekly Roundup 11/27/25 (Who we are thankful for, S&P downgrades Tether) (EP.687)

Matt and Nic are back for another week of news and deals. In this episode: <ul> <li>Is Quantum FUD causing Bitcoin to sell off?</li> <li>Ray Dalio is worry about Quantum</li> <li>Scott Aaronson is worried about quantum computing</li> <li>Vitalik is worried about quantum</li> <li>Quantum upgrade scenarios</li> <li>Are we still suffering from the flash crash?</li> <li>The DATs are selling</li> <li>DAT spot arbitrage</li> <li>Will the US government end up with the Satoshi coins</li> <li>Should the government bail out AI?</li> <li>Will NFTs come back?</li> <li>IBIT is Harvard's largest 13F position</li> <li>David Frum on stablecoins</li> <li>Will stablecoins require a bailout?</li> </ul>

<description>&lt;p&gt;Matt and Nic are back for another week of news and deals. In this episode: &lt;/p&gt; &lt;ul&gt; &lt;li&gt;Is Quantum FUD causing Bitcoin to sell off?&lt;/li&gt; &lt;li&gt;Ray Dalio is worry about Quantum&lt;/li&gt; &lt;li&gt;Scott Aaronson is worried about quantum computing&lt;/li&gt; &lt;li&gt;Vitalik is worried about quantum&lt;/li&gt; &lt;li&gt;Quantum upgrade scenarios&lt;/li&gt; &lt;li&gt;Are we still suffering from the flash crash?&lt;/li&gt; &lt;li&gt;The DATs are selling&lt;/li&gt; &lt;li&gt;DAT spot arbitrage&lt;/li&gt; &lt;li&gt;Will the US government end up with the Satoshi coins&lt;/li&gt; &lt;li&gt;Should the government bail out AI?&lt;/li&gt; &lt;li&gt;Will NFTs come back?&lt;/li&gt; &lt;li&gt;IBIT is Harvard's largest 13F position&lt;/li&gt; &lt;li&gt;David Frum on stablecoins&lt;/li&gt; &lt;li&gt;Will stablecoins require a bailout?&lt;/li&gt; &lt;/ul&gt;</description>

Weekly Roundup 11/21/25 (Quantum FUD, DAT hangover, stablecoin duration risk) (EP.686)

Hosts Matt Walsh and Nic Carter of Castle Island Ventures explore news and deals in the public blockchain space and talk to some of the leading experts in the industry. Learn more and stay up to date at CastleIsland.vc and follow on twitter @CastleIslandVC

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