1480586463
On The Brink with Castle Island

Advertise on podcast: On The Brink with Castle Island

Rating
★★★★★
4.8
from
288 reviews
This podcast has
754 episodes
Language
English
Explicit
No
Date created
2019/09/18
Latest episode
2026/10/23
Average duration
37 min.
Release period
6 days

Description

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

Unlock On The Brink with Castle Island podcast Email contact info,
Listeners & Audience details

Email contact information

Direct podcast contact details

Listeners

Audience numbers & engagement insights

Audience details

Podcast Insights

Social media

Check On The Brink with Castle Island social media presence


Podcast episodes

Check latest episodes from On The Brink with Castle Island podcast


Weekly Roundup 10/23/26 (Gold alchemy, rogue financial AI agents, GENIUS implements stablecoin yield)
2026/10/23
Matt and Nic are back with another week of news. In this episode: Marathon Fusion says it has turned mercury into stable gold What would commercially viable alchemy mean for Bitcoin's scarcity argument? AI tools uncover a major vulnerability in PHP A certificate authority's private keys turn out to be trivially guessable Railway warns developers to revoke their secrets after a cyberattack Banks are finding third-party AI agents inside customer accounts Who's responsible when your AI agent acts without instructions? The OCC finalizes its GENIUS Act rules Stablecoin issuers can't pay yield directly, but where does that leave third-party rewards? a16z reportedly plans to drop "crypto" from its flagship fund's name Ali Yahya is leaving to start a company Microsoft, Alphabet, and Goldman Sachs object to tokenized versions of their shares Should public companies have a veto over tokenizing their stock? Polymarket faces growing pains as Kalshi gains ground Are perpetual preferred shares a new source of Bitcoin demand? Can compute derivatives give investors a way to short the AI boom? Content mentioned in this episode: Marathon Fusion, Alchemy OCC, Final Rule to Implement the GENIUS Act Fidelity Digital Assets, Perpetual Preferred Stock: The Newest Demand Catalyst in Bitcoin Bitwise, Q4 2026 Staking Report Wired, The DEA's Premier Crypto Detective: Clues Led Straight to Her Own Family Bloomberg, Polymarket Investors Push CEO Coplan for Change as Kalshi Gains Ground The Wall Street Journal, Want to Short the AI Boom? She Wants to Give You a Way to Bet on Compute Prices
Weekly Roundup 10/16/26 (OCC debanking report, Google's quantum advance, Ledger spy chips, Richard Heart apprehended)
2026/10/16
Matt and Nic are back with another week of news and deals. In this episode: The OCC publishes its debanking findings on America's largest banks Will the banks' fixes satisfy regulators? Google makes another advance in quantum error correction Coinbase lays out its requirements for Bitcoin's post-quantum migration Can Bitcoin's quantum transition accommodate institutional MPC wallets? OpenAI is reportedly in talks to buy Trail of Bits Patrick Witt leaves the White House — where does that leave Clarity? DWF Labs subsidiaries sue BitGo for $141m over allegedly premature token sales Spy chips in reseller-supplied Ledger devices steal recovery phrases Ledger announces an Android device with Solana Mobile Cboe gets approval for binary options on public company metrics The CFTC draws the line between prediction markets and sportsbooks Richard Heart is reportedly detained in Istanbul What's NYC Mayer Zohran Mamdani doing with a quantum computer? Content mentioned in this episode: OCC, Guaranteeing Fair Banking for all Americans Nic on Convergence: quantum risk and AI-driven advances in math Google Quantum AI on magic state cultivation Coinbase, Working Together on BTC Post-Quantum Readiness Jeff Yan on Bloomberg's Odd Lots
Weekly Roundup 10/09/26 (Going Bunker Mode, classical ECC breaks, AI's math discoveries)
2026/10/09
Matt and Nic are back with more deals and news. In this episode:  Is it appropriate to have AI manage your fantasy league? Quant firms are hiring "quals" Justin Drake scares everyone in crypto Did AI destroy math? Why a classical ECDSA break would be worse than a quantum one Why we lean forward hash-based signatures for post-quantum Why rotating your address doesn't help now Is Bitcoin the "least of our concerns" if ECC breaks? Nic makes a new scientific discovery with Astra The NFL thinks that gambling should be state regulated What's driving interest in Pokemon cards? Content mentioned in our episode: Coin Metrics, The Death and Life of the Average Memecoin
Esther Wong (Cashi) on Making Stablecoins Spendable
2026/10/05
Esther Wong, founder and CEO of Cashi joins the show. Cashi is a stablecoin spending app and cashback card with a global footprint. In this episode we discuss: Customer personas and use cases for stablecoin payments The future of tokenized equities on chain The landscape of layer one and two blockchains and how these platforms converge with global stablecoin applications Cashi's roadmap and plans for the coming year To learn more about Cashi, visit their website and follow Esther Wong on X.
Weekly Roundup 10/02/26 (Fat Model Hypothesis, Agentic bank runs, Hester Peirce retires from the SEC, ETH 2030)
2026/10/02
Matt and Nic are back with another week of news and deals. In this episode:  Are OpenAI and Anthropic reenacting the Fat Protocol Hypothesis Will AI agents cause bank runs optimizing bank balances for yield? If the AI complex bursts does it take down VC? Our tribute to Hester Peirce as she retires from the SEC The SEC and CFTC publish crypto FAQs Vitalik lays out his vision for Ethereum in 2030 Quantum progress is accelerating Illinois delays their crypto transaction tax  Is San Francisco better than it was?
Weekly Roundup 09/25/26 (Post Clarity rulemaking, Sherrod Brown is back, RIP BitMEX, Coldcard white hats, is EA a cult?)
2026/09/25
Matt and Nic are back with another week of news and deals. In this episode:  How loud are America's largest data centers? What's wrong with XAI's data center in Mississippi? The Trump admin is reportedly trying to promote dollar stablecoins Binance invests in Circle We pick up the pieces after Clarity Fairshake plans to spend $30m opposing Sherrod Brown in Ohio How AI anxiety helps the Democrats Sherrod Brown is back to haunt crypto Coinbase is listing IPOs now Are prediction markets out of step with the original vision? BitMEX finally closes its doors 52 BTC were saved from the Coldcard hack by white hats Is Anthropic privatizing the frontier? A White House memo says effective altruism is a cult Content mentioned in this episode: Nic on Substack, How Noisy are America's Largest Data Centers?
Weekly Roundup 09/18/26 (Clarity fails to advance, Caroline Ellison's new job, AI leaking MNPI, Poland's oil snafu)
2026/09/18
Matt and Nic are back for another week of news and deals. In this episode:  How is SBF like Dario? The EAs are at it again Do we need new regulation to Pace the Frontier? Can Anthropic be regulated like a bank?  Are baseball cards back? Clarity fails at the final hurdle Why did Clarity fail? Stablecoin yield is still in effect The SEC and CFTC are engaging in rulemaking Circle launches Arc, their new L1 Robinhood employees get caught insider trading on Hyperliquid Caroline Ellison is back and working for a former FTX portco Can AI models leak MNPI? A Polish oil company tried to buy sanctioned oil from Venezuela with USDT The DOE launches a $250m Quantum computing competition
Weekly Roundup 09/11/26 (Liquid hack, AI x-risk, Silvergate revisited, can AI leak MNPI?)
2026/09/11
Matt and Nic are back for more deals and news. In this episode:  We bring back his the theme music Anthropic employees think there's a 10% chance AI destroys humanity Was Jacob Coxon astroturfed or real? Are Anthropic employees being sincere or cynical? Blockstream's Liquid sidechain is hacked What does the Liquid hack mean for privacy coins? Hunter Biden launches the $LAPTOP memecoin IONQ says they will be able to crack ECC in two years Ex Silvergate CEO Alan Lane speaks out OpenAI offers a solution to the Navier-Stokes problem  Can insider information leak through AI models?  Why AI doom is like Pascal's mugging Content mentioned: Alan Lane, Silvergate's Voluntary Liquidation
Weekly Roundup 09/04/26 (HuggingFace hack breaks containment, Hyperliquid onshoring, RSA260 factored, is the stablecoin sandwich cheaper?)
2026/09/04
Matt and Nic are back for another week of news and deals. In this episode:  We determine the winner of the bad boys theme song competition Dwarkesh ignites controversy with his OpenAI hack recap What actually happened with OpenAI and Huggingface? Gwern's and Matt Huang's short story competition Will AI make us dumb? 200m Americans KYC data has been hacked Prediction markets lawsuit heading to SCOTUS? Robinhood Chain is taking off Strategy is buying Bitcoin again Should Members of Congress be paid more? Cronos suffers a defi hack Revolut gets a bank charter Is the stablecoin sandwich cheaper for cross border? RSA260 factored - panic? Content mentioned in the episode: GPUworld.com Wenxin Du, Three Myths About Payment Innovation
Guy Young (Ethena) on Digital Financial Markets
2026/09/02
Wyatt sits down with Guy Young, founder of Ethena, for Guy's third appearance on the pod. In this episode: What has driven Ethena's success and durability? Where is there demand for other yield assets? Where is capital coming from? Is full onchain portfolio construction possible today? Why tokenize financial products at all? Who are the eventual winners? How is Ethena positioning to an evolving onchain yield landscape?
Weekly Roundup 08/28/26 (BankChain alliance, Goat grazing hedges, SHRINCS, is maximalism over?)
2026/08/28
Matt and Nic return for another week of deals and news. In this episode:  Matt and Nic consider candidates for the new bad boys intro music 39 state banking associations form the BankChain alliance Blockstream researchers proposed SHRINCS, a PQ signature scheme for Bitcoin How much should depositors care about bank credit risk? Kalshi hosts a prediction market on goat grazing regulation Are trading bot agents getting good? Blockstream proposes SHRINCS for Bitcoin Zcash hits an 8-year high Treasury designates anyone helping Iran's crypto sector AI watermarking Bad boys theme song submissions: Ian's song Seth's song Content mentioned: Omid Malekan, The banking lobby's bad faith campaign to kill the Clarity Act will backfire Nic Carter, A Second and Final Eulogy for Bitcoin Maximalism
Weekly Roundup 08/21/26 (SALT Wyoming, SEC's Reg Crypto, Tether's big 4 audit, Crypto Privateers)
2026/08/21
Matt and Nic return for another week of news and deals. In this episode:  The boys review SALT Wyoming in Jackson Hole Why did Stripe buy Openrouter? Stripe says we have entered the Singularity People are upset about data centers The SEC proposes Reg Crypto governing token issuance The CFTC convenes a crypto roundtable in Washington FASB proposes treating stablecoins as cash equivalent under GAAP World Liberty gets an OCC charter Trump should divest his WLF tokens to push Clarity through Saylor wriggles out of another jam Tether passes a big 4 audit The White House issues a "crypto privateer" memo
Weekly Roundup 08/14/26 (Anti-Datacenter sentiment, dinosaur fossil investing, SEC is DIYing Clarity)
2026/08/14
Matt and Nic are back for another week of news and deals. In this episode:  Who is the main character in AI? Why are people so mad about datacenters? Sherrod Brown is back and he's running against AI Are datacenters being built with Flock? Culturally scarce goods and dinosaurs are rallying The SEC starts to fill the gap left by the Clarity Act FinCEN ends beneficial ownership reporting The CFTC charges a $400m Ponzi operator Are there successful Ponzi schemers? Is Bitcoin at risk from miners transitioning to AI? The collapse of the diamond market
Weekly Roundup 08/07/26 (Coldcard hack continues, Ethereum mulls an issuance tweak, ai16z winds down, Clarity deadline looms)
2026/08/07
Matt and Nic are back with more news and deals. In this episode:  Why the Coldcard hack is worse than some major exchange and DeFi hacks What the Coldcard hack told us about the need for open weight models Is self custody over? MSTR sells more Bitcoin An FBI agent steals $1m in crypto NY state sues Kalshi Ethereum considers another change to issuance Ethereum needs to resist the urge to change monetary policy ai16z's Eliza winds down the merit of reading sci fi The cofounder of Sui leaves for Anthropic Will Anthropic keep the discoveries to themselves? The WSJ gets it wrong on Clarity
Weekly Roundup 07/31/26 (Situational Awareness collapse, Coldcard exploit, latest on CLARITY, Ice Cream Kalshi hedges)
2026/07/31
Matt and Nic are back for another week of news and deals. In this episode:  What the novel Hyperion tells us about AI doom Situational Awareness liquidates most of its public book after a sharp AI selloff Will Leo have a second act? Why has AI been selling off? Over 1000 BTC stored in Coldcard wallets were stolen due to bad entropy Where does self-custody go from here? What happened with Coldcard? Political winds are shifting against crypto as midterms loom Strategy continues to strengthen its balance sheet with MSTR common sales An ice cream shop in CA is hedging the weather with Kalshi Circle buy's IBM's blockchain patent portfolio Visions of Bitcoin turns 8 this week  Content mentioned this episode:  Nic and Hasu, Visions of Bitcoin

Podcast reviews

Read On The Brink with Castle Island podcast reviews


4.8 out of 5
288 reviews
★★☆☆☆
Prnzzzzzx 2026/10/05
Good content but ableist
I like the podcast overall but was really disappointed to hear them rip into Dario Amodei, who clearly suffers from autism, for being "weird" while gr...
★☆☆☆☆
Ixzo 2025/12/01
Found the most boring pod in bitcoin
If you want to hear two guys rattle off ‘news’ about companies nobody cares about, this is your pod. Some company acquired another company - snooze. A...
★★★★★
jeromemichael888 2025/11/29
Best Weekly Recap
The insight and analysis from Matt and Nic is unmatched. I look forward to this recap every week. An absolute must listen. (Praying some terrorist tur...
★★☆☆☆
notageek99 2025/10/24
What happened to you being vocal about the “bad boys”??
The way you’ve flipped the pancake on the bad actors in your industry and inability to call out the grift going on by the White House is hugely disapp...
★★★★☆
kfixbwhdisa 2025/08/25
Used to be good
bleh
★★★★★
xxflightbenefitsxx 2025/04/20
Solid information
I’ve really grown into Nic and Matt and am a big fan of their delivery. Very consistent, nic is definitely my favorite crypto “ journalist “
★★★★☆
Jack-222 2024/09/15
Like the show, but you guys sometimes go into areas you don’t know anything about
I really enjoy your podcast. I do. But, I find it is interesting that you guys are veering into politics because one person is pandering to you. Can’...
★★★★★
mizt@ken 2024/05/22
Awesome Content
Honest take on any news. Very relevant to crypto market. The hosts compliment each other on humor and energy level.
★★★★★
derekva 2024/01/02
Excellent
Truly high quality content. And with very low key understated humor bonus.
★★★★☆
Hokaneishi 2023/10/15
Great pod
Keep up the bad boys coverage and don't forget the music! I'll bump to 5 stars once the music is back 😁
check all reviews on apple podcasts

Podcast sponsorship advertising

Start advertising on On The Brink with Castle Island relevant audience podcasts


What do you want to promote?