On The Brink with Castle Island

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**On The Brink with Castle Island**

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

Latest Episodes:

Weekly Roundup 02/13/26 (SBF wants a retrial, taking stock of Web3, Clarity deadlocked) (EP.701) Feb 13, 2026

Show notes

Matt and Nic are back with another week of news and deals. In this episode:

Matt reflects on the Patriots season
We review the Superbowl Ads
Looking forward to the OpenAI wearable
Is "something big happening" in AI?
Does crypto accelerate the rise of malicious AI?
Are all communications networks going to break down in 90 days?
SBF wants a new trial
Blackrock adds BUIDL to Uniswap
Blockfills suspends withdrawals
Robinhood is internalizing their prediction market product
The stablecoin yield issue in Clarity is still a problem
Fairshake is getting active in the midterms
Is Chris Dixon right about Web3?
We review winter olympic sports

Content mentioned:

Chris Dixon, The long game for crypto

Bhavin Vaid (Birch Hill) on Better Markets for Tokenized Assets (EP.700) Feb 11, 2026

Show notes

Wyatt sits down with Bhavin, co-founder of Birch Hill to chat about the tokenized asset and DeFi market broadly. In this episode:

Who is assessing whether cryptoassets are safe in DeFi today?
Who is assessing risk and ensuring assets are solvent and not fraudulent?
How have these standards been set and how are they evolving?
What is a risk curator, how do risk curators make money, and what is their role?
Is it the responsibility of protocols, curators, wallets, or someone else to protect users from buying bad assets?
How do you expect non-DeFi-native market participants will start to enter this market?
Will users eventually buy, hold, and sell assets on protocol interfaces, brokerages / exchanges, or risk curator interfaces?
Does the Fat Protocol Thesis hold true? Where does value accrue today?

Weekly Roundup 02/06/26 (Bitcoin bloodbath, Digesting Epstein's Emails, Ethereum rethinks L2s) (EP.699) Feb 06, 2026

Show notes

Matt and Nic are back with another week of news and deals. In this episode:

Bitcoin grapples with the fallout of the Epstein Emails
Did Jeffrey Epstein influence Bitcoin development?
Is Bhutan selling their Bitcoin?
Do Bitcoin devs care about quantum?
Is Bitcoin Core under the influence with sophons
Kyle Samani steps back from Multicoin
What Samani's departure means for crypto
Is web3 dead forever?
Vitalik starts second-guessing the L2-centric roadmap
Tether is trading at a slight discount

Content mentioned in this episode:

Nic on Substack, Bitcoin developers are mostly not concerned about quantum risk

Weekly Roundup 01/30/26 (Fidelity's FIDD, Gold rally, Worldcoin and AI bots, digital alibis) (EP. 698) Jan 30, 2026

Show notes

Matt and Nic are back with another week of news and deals. In this episode:

Matt is heated about the Belichick HoF vote
Fidelity launches a stablecoin FIDD on Ethereum
Market structure passes Senate Ag Cmte
The White House crypto council is being revived to find a compromise on stablecoin yield
Fairshake has another war chest for the midterms
Do stablecoins cause bank deposit contraction?
Tether has 140 tons of gold now
Why is Bitcoin not participating in the "debasement" trade?
Is gold at risk from alchemy?
People are still worried about quantum
Will Worldcoin save us from AI bots?
What's the solution to the AI slop apocalypse?
Digital alibis with blockchains

Content mentioned in this episode:

Niall Ferguson and Manny Rincon-Cruz, Stablecoins Are the Future but Banks will Survive
McKinsey and Artemis, Stablecoins in payments: What the raw transaction numbers miss

Weekly Roundup 01/23/26 (CLARITY stalls, Iran's USDT reserves, Is Web3 Social over?) (EP.697) Jan 23, 2026

Show notes

Nic and Matt are back for another week of news and deals. In this episode:

There's a big storm coming
Matt's playoff picks
Farcaster sells to Neynar
Is this the nail in the coffin for Web3Social?
Where Farcaster went wrong
BitGo goes public
NYSE is building a tokenized security trading platform
Are we looping back around to enterprise blockchains?
A MA judge has issued an injunction against Kalshi
Jeffries drops Bitcoin from its model portfolio over quantum risk
Coinbase launches an advisory board on quantum
Trump sues JPM for debanking him
Does the Central Bank of Iran really control $500m worth of USDT?
What's next for Caroline Ellison?

Weekly Roundup 01/16/26 (CLARITY problems, InfoFi Dead, CA Wealth Tax, Kontigo) (EP.696) Jan 16, 2026

Show notes

Matt and Nic are back after a week off. In this episode:

The Clarity market structure bill markup is delayed for now
Coinbase backs out of supporting Clarity
The bank lobby is trying to torpedo Clarity
Kontigo is accused of ignoring sanctions
X changes its API to block InfoFi
California's wealth tax has backfired already
BitMine invests $200m into Mr Beast's company
Why tokenized deposits aren't as interesting as stablecoins

Content mentioned in this episode:

Jason Mikula, Kontigo: Y Combinator's Venezuelan Sanctions Evasion Startup

Wyatt & Jake Lynch on Onchain Financial Markets (EP.695) Jan 12, 2026

Show notes

Wyatt, Henry, and Jake recently put out a report called "Total Value Lost", exploring how best to assess the value of various DeFi markets - starting with lending markets. This episode is a continuation of that conversation, exploring what carries value in DeFi going forward, particularly on the back of a shaky market period. This discussion covers:

Where does the recent, ongoing market selloff leave us?
What metrics matter for onchain markets?
What market dynamics contributed to the October 10 washout?
How does leverage manifest in onchain markets, and what does it look like today?
How do you assess the value of illiquid cryptoassets?
What drives revenue multiples.
Which protocols will benefit from the tokenization of other asset classes, and which will struggle?
How do the individual behaviors and incentives of investment funds contribute to crypto market volatility?