Bennett Collen and Stephanie Howard (Endstate) on building a web3-native fashion brand (EP.346)
On The Brink with Castle Island
Release Date: 09/06/2022
Weekly Roundup 07/09/26 (BonkDAO exploit, Choke Point 2.0 extended to audit firms, Kraken v Mazars) (EP.729)
On The Brink with Castle Island
Matt and Nic are back with another week of news and deals. In this episode: Strategy sells $216m worth of BTC Where does Strategy go from here with STRC? Kalshi’s case faces the ban of sports contracts in NY TeraWulf signs a massive lease with Anthropic BonkDAO’s legal hack Vanguard hires a head of digital assets Kraken wins arbitration against Mazars for de-auditing them in 2022 Vitalik lays out a new four year plan Polymarket’s 5 minute BTC markets are being manipulated Content mentioned:
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Weekly Roundup 07/03/26 (OpenUSD announced, Binance leaves the EU, Strategy’s new framework) (EP.728)
On The Brink with Castle Island
Matt and Nic are back with another week of news and deals. In this episode: Saylor releases Strategy’s “Digital Credit Capital Framework” MSTR stabilizes for now though STRC is still discounted Is Saylor transitioning MSTR into a Bitcoin hedge fund? Is Strategy doing anything tricky with their mNAV calculation The OpenUSD consortium is announced Is the Tether and Circle duopoly broken? Can stablecoin consortiums work? What could cause OpenUSD to fail? Trump's 2025 diclosures include a lot of crypto Binance leaves the EU for now The K-pop DAT ends its digital asset...
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Weekly Roundup 06/26/26 (Quantum EOs, STRC's selloff, more MSTR) (EP.727)
On The Brink with Castle Island
Matt and Nic are back for another week of news and deals. In this episode: Our recording snafu STRC's depeg explained Saylor's path forward Why Strategy's issue is the converts Polymarket's questionable marketing Trump's Quantum EOs
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Weekly Roundup 06/19/26 (STRC under pressure, Illinois’ crypto tax, Open weight AI vs the AI boom) (EP.726)
On The Brink with Castle Island
Matt and Nic are back for a week of news and deals. In this episode: The Tartan Army takes over Boston Europeans are shocked that American infrastructure works STRC falls into the low $80s STRC’s liquidation cascade mechanics What are Saylor’s options now? Is the US right to put the brakes on Fable? Will open weight models puncture the AI boom? Are we living in a vulnerable world? Kristin Gillebrand’s son raises $30m for a perps exchange Make sure your tokenized equity provider has the equity Why aren’t publishers doing pay per content Content mentioned: Nick Bostrom, ...
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Weekly Roundup 06/12/26 (Strategy survives, Zcash Orchard bug, the thin model hypothesis) (EP.725)
On The Brink with Castle Island
Matt and Nic are back with a new week of news and deals. In this episode: Spanish soccer club Osasuna hedges their relegation on Kalshi Strategy shocks people by buying the dip Is Strategy sacrificing MSTR to save STRC? Saylor bolsters his cash position What factors are dragging on the BTC price? Zcash fixes a scary inflation bug SBF formally applies for a Presidential pardon The CFTC proposes banning a subset of prediction market contracts Polymarket thinks that Kalshi is spying on them European fans in America for the World Cup are discovering Buc-ees The DATs are struggling Hester...
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Omid Malekan (Columbia Business School) on Private Money, Financial Systems, and Crypto in Geopolitics (EP.724)
On The Brink with Castle Island
Wyatt sits down with Omid Malekan, a Professor at Columbia Business School, author of several books, and "Explainer-in-Chief" of blockchain technology. In this episode, Wyatt and Omid discuss: Why do stablecoins carry a persisent sense of being "dangerous" or "ungovernable? Are stablecoins truly private money? How do we define private money? Who owns our current banking and payment systems? Why do banks vocally oppose stablecoins? Who will own and control digital money networks? Are blockchains the right medium for digital finance over the long term? Is digital trust a problem?
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Weekly Roundup 06/05/26 (MSTR wobbles, Polymarket’s MSTR market, Andrew Left convicted) (EP.723)
On The Brink with Castle Island
Matt and Nic are back for another week of news and deals. In this episode: FIFA’s World Cup ticketing scandal Andrew Yang is now a crypto and telecoms entrepreneur Are Strategy’s woes responsible for the Bitcoin pullback? Will Saylor defend STRC or MSTR? What are Saylor’s options here? Polymarket has another market resolution SNAFU How UMA could be used to exploit Polymarket BitMine considers a perpetual preferred security Google’s quantum circuit is Galaxy launches OTC trading for prediction markets Treasury sanctions Iran’s largest digital asset exchanges Andrew Left of...
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Weekly Roundup 05/29/26 (Was debanking real, SoFiUSD, WSJ gets free banks wrong, trouble in ETHland) (EP.722)
On The Brink with Castle Island
Matt and Nic are back with another week of news and deals. In this episode: The CEO of Lead bank says debanking was made up Which aspects of debanking were real? The SEC scraps its 50-year-old gag rule The WSJ gets free banking history wrong in their attack on stablecoins What does history tell us about decentralized monetary issuance Why stablecoins aren’t vulnerable to the same issues as free banks SoFi launches SoFiUSD and mixes a stablecoin with a tokenized deposit Sentiment is bottoming in Ethereum David Hoffman sells his ETH Are stablecoins parasitic to L1s Can L1s accrue value...
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Weekly Roundup 05/22/26 (AI and power bills, SpaceX IPO, Prime Trust clawbacks, USG invests in quantum) (EP.721)
On The Brink with Castle Island
Matt and Nic are back with another week of news and deals. In this episode: Are AI datacenters better or worse for the environment than Bitcoin miners? AI is not responsible for your power bills Why AI could actually drive down residential power prices Is AI less popular than crypto ever was? The negative societal effects of tech companies staying private for longer We analyze the SpaceX S1 OpenAI solved one of the Erdos problems The US government is taking equity stakes in quantum computers Jane Street is still dealing with the Terra fallout Prime Trust is trying to claw back assets...
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Weekly Roundup feat. Gus Coldebella 05/15/26 (Clarity advances, Circle’s Arc token) (EP.720)
On The Brink with Castle Island
Matt and Nic are aback with another week of news and deals, today joined by Gus Coldebella to cover the CLARITY Act. In this episode: The Clarity Act advances resoundingly from committee Sen. Warren doesn’t like the Clarity Act Will there be an ethics provision inserted into Clarity? The next fight in DC What’s up with Nantucket real estate? Nantucket’s ponzinomics Nantucket is the birthplace of venture capital Circle is issuing a token Cprkrn recovers 5 BTC with the help of Claude
info_outlineRia and Nic from Castle Island sit down with Stephanie Howard and Bennett Collen, cofounders of Endstate, a web3 footwear and fashion brand. We cover the merits of the redeem-and-retain NFT model and the vision for Endstate.
- Bennett’s prior crypto startup and how he decided to unite his passion for sneakers with web3
- How Bennett and Stephanie met and cofounded Endstate
- Stephanie’s career in sneaker design to date
- Why creators and athletes are jumping at the opportunity to issue merchandise-linked NFTs
- Why Bennett and Stephanie chose to launch a web3 native brand
- How redeem-and-retain NFTs allow manufacturers to reduce inventory risk
- Why fashion is getting more targeted and niche
- Why Endstate is able to release new iterations of their sneakers so quickly
- Endstate’s rationale for manufacturing in the US
- Endstate drops to date
- Endstate’s new drop with Eagles wide receiver DeVonta Smith
- How web3 brands should think about which metaverse to build for
- Endstate’s thinking around Solana vs Ethereum and the impact of gas fees
- How to link physical products with NFTs – from NFCs to QRs to visual scans
- What should we call physical NFTs?
- Aside from shoes, what merch is amenable to the Endstate model?
- What product sectors will be NFTed?
- How developed are authenticated third party marketplaces for physically linked NFTs?
- Physical-linked NFTs as a trojan horse to onboard mass markets into web3
- The future state of Endstate
- Other web3 drops Bennett and Stephanie enjoyed
- The future of entangled NFTs
Read more:
- Nic Carter on Medium: Redeem and Retain NFTs are the future of Luxury Goods
- Vogue Business: How the crypto bear market is resetting fashion’s Web3 strategy
Drops and more at endstate.io
Intro and outro music: Daniel Allan's Collage #344