Strategy is Trapped & in Crisis — "It's Basically a Hedge Fund Now" | Jeff Dorman & Matt Walsh
Michael Saylor’s Strategy bought itself time, but did it actually solve the problem? David sits down with Jeff Dorman and Matt Walsh to unpack Strategy’s increasingly complex capital structure, why $STRC and MSTR are now fighting for oxygen, whether Saylor may need to sell Bitcoin, and why the company is starting to look less like a levered BTC play and more like an actively managed hedge fund.
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TIMESTAMPS
0:00 Intro
2:30 Can Stretch Return to 100?
4:00 Explaining the New Framework
4:43 Can the Capital Stack Coexist?
6:39 Refunding the Converts
8:32 MNAV Near the Breaking Point
11:15 Option Value or Investor Betrayal
15:37 Legal Risk and Retail Exposure
19:52 Buying Time, Not Solving It
22:20 Scenario Odds After the Pivot
24:54 Sell Bitcoin or Wait
28:59 M&A as a New Path
34:13 Temporary Relief, Future Crash
36:21 Slow Bleed, Not Bankruptcy
40:58 Bitcoin Needs a Bigger Narrative
46:56 Would Jeff Buy Stretch?
48:26 Is the Model Actually Genius?
52:09 Closing & Disclaimers
---
RESOURCES
Matt Walsh
https://x.com/MattWalshInBos
Jeff Dorman
https://x.com/jdorman81
---
Not financial or tax advice. See our investment disclosures here:
https://www.bankless.com/disclosures
Why MSTR Should Have Sold $2 Billion Instead of $2 Million of Bitcoin
Jeff Dorman on why Strategy's four stakeholder classes are all losing, and why Saylor should have sold $2B of Bitcoin at once instead of $2.5M.
========================================================
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Fidelity: Explore opportunities at https://crypto.fidelitycareers.com
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Strategy’s late-May Bitcoin sale has turned a long-running investor concern into a sharper question: how sustainable is the company’s capital structure if its Bitcoin accumulation strategy now comes with large cash obligations?
Jeff Dorman, chief investment officer at Arca, joins Laura Shin to discuss why the sale changed his view of the risks around Strategy. After months of pushing back on fears of forced selling, Dorman says the company’s preferred-share financing has altered the analysis.
He points to roughly $15 billion in preferred shares carrying 10% to 12% dividend rates, which he estimates could mean about $1.7 billion in annual cash obligations for a company without operating revenue.
Dorman also breaks down the stakeholder groups shaping Strategy’s choices, the tradeoffs each path may create, and the Polymarket dispute over whether Strategy sold Bitcoin in May.
Host:
Laura Shin, Host / Unchained
Guests:
Jeff Dorman - Chief Investment Officer at Arca - https://x.com/jdorman81
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The Ultimate Coinbase Debate: Can It Survive? | Jeff Dorman
Gm! This week we're joined by Jeff Dorman to discuss his recent tweet on the bear case for Coinbase. We deep dive into the Coinbase business model, the rise of DEXs (Hyperliquid), who is best positioned to win the exchange wars, the opportunity for DeFi & more. Enjoy!
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The first application launching on Zenrock is zenBTC – yield-bearing Bitcoin on Solana. zenBTC will be live in April 2025.
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Timestamps:
(00:00) Intro
(03:06) Do Fundamentals Matter In Crypto?
(08:58) Ripple's Breakthrough Moment
(11:38) Ads (Aptos, Zenrock)
(12:58) The Coinbase Business Model
(20:59) Are Coinbase Users Sticky?
(25:29) The Rise Of DEXs
(31:41) Ads (Aptos, Zenrock)
(33:01) Is There A Bull Case For Coinbase?
(37:55) Tokenization
(43:37) Ads (Falcon x, Token.com)
(45:05) The Opportunity For DeFi
(50:32) Value Accrual
(57:07) How To Bring Assets Onchain
(01:10:09) Should Securities Laws Be Updated?
--
Disclaimer: Nothing said on Empire is a recommendation to buy or sell securities or tokens. This podcast is for informational purposes only, and any views expressed by anyone on the show are solely our opinions, not financial advice. Santiago, Jason, and our guests may hold positions in the companies, funds, or projects discussed.
Memes and 'madness' are taking mindshare from a real industry - Jeff Dorman
The Scoop's host, Frank Chaparro, was joined by Arca CIO Jeff Dorman.
In this episode, Chaparro and Dorman discussed the disconnect between market sentiment and the developments in the crypto space. Dorman goes over the actual use cases of the crypto ecosystem and how they are being drowned out by memecoins and scandals, highlighting that big outside players are beginning to get on board.
OUTLINE
00:00 Introduction
01:11 Sponsor break
02:04 Memes taking the spotlight
06:40 Crypto’s adolescent stage
11:29 Common misconceptions about crypto
18:50 Assessing value in the crypto space
23:00 Are we still early?
29:37 The future of crypto
34:50 Where are the liquid funds?
41:30 Tradfi will eventually come
45:04 Conclusion
GUEST LINKS
Jeff Dorman - https://www.linkedin.com/in/jeff-dorman-cfa-61063129
Jeff Dorman on X - https://x.com/jdorman81
Arca - https://x.com/arca
Arca on X - https://www.ar.ca/
Crypto Sentiment Is Down Bad. But Is It Time to Go All In? - Ep. 784
Crypto sentiment is extremely low, but is the market completely wrong? While X is flooded with doomsday takes, Jeff Dorman, CIO of Arca, argues that the real fundamentals of crypto are stronger than ever.
In this episode, Jeff breaks down why investors are overlooking key signals—like growing regulatory clarity, the tokenization of real-world assets, and institutional interest—and how memecoins have hijacked the broader market narrative. He pushes back on claims that there are no fresh narratives and explains why the current climate reminds him of previous market mispricings that turned into massive opportunities.
He also dives into the potential of tokenized assets, why crypto adoption is way ahead of where people think, and why he believes the industry keeps making the same mistakes when it comes to marketing its breakthroughs.
Show highlights:
2:03 - How dishonest takes are flooding the crypto sentiment, according to Jeff
4:04 - Why he pushes back against the sentiment that there are no fresh narratives
6:13 - Whether memecoins are to blame for the poor market sentiment
13:17 - Why Jeff feels that the crypto investment thesis is still very strong
19:23 - Why Jeff says that the launch of $TRUMP and $MELANIA was a good thing for the industry
26:55 - Why layer 1s are very hard to invest in
30:57 - Laura and Jeff’s disagreement about what would it take for a blockchain to win
Visit our website for breaking news, analysis, op-eds, articles to learn about crypto, and much more: unchainedcrypto.com
Thank you to our sponsors!
Somnia Network
Guest
Jeff Dorman, Chief Investment Officer and Co-Founder at Arca
Previous appearance on Unchained: Crypto Prices Are Way Down. Is It Time to Buy the Dip?
Links
Unchained:
Arca: “That’s Our Two Satoshis” - I’m Fed Up with the Misinformation by Jeff Dorman, CFA
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Crypto Prices Are Way Down. Is It Time to Buy the Dip? - Ep. 684
The recent crypto crash has left many investors questioning the way the market is going. In this episode, Jeff Dorman, chief investment officer at Arca, provides a deep dive into the factors behind the crash, the macroeconomic influences at play, and why he remains optimistic despite the downturn. Expressing surprise at Ethereum's underperformance this year, he describes how the Democrats’ handling of crypto is an own goal, and how TradFi and DeFi differ from each other during market upheavals.
Show highlights:
00:00 Intro
01:38 The two main reasons the markets crashed this past weekend
05:29 How the macro environment has affected crypto lately and why the market has gotten “way ahead of itself”
12:44 Why ETH was down so much, more than other cryptocurrencies
16:52 The “most important” shift in crypto policy that has occurred this year
21:19 The Japanese yen carry trade that was one of the key factors in the market meltdown
30:20 Whether Genesis distributing $4 billion in assets had an impact on the market
33:39 Why Jeff believes that the data we have today does not point to a recession in the U.S.
36:49 Why Jeff says he’s "buying the dip”
40:47 Crypto as a political issue and why he thinks Harris winning would not be as bad for crypto as many believe
48:19 Why bitcoin doesn’t always act as a hedge against equity-related or geopolitical risk, in Jeff’s opinion
52:56 What Jeff thinks about the proposals for the U.S. government to buy bitcoin for a strategic reserve
54:15 The stark contrast between TradFi giants halting trading and the permissionless nature of DeFi
Visit our website for breaking news, analysis, op-eds, articles to learn about crypto, and much more: unchainedcrypto.com
Thank you to our sponsors!
Polkadot
Token 2049
Guest:
Jeff Dorman, Chief Investment Officer at Arca.
Previous appearances on Unchained:
How Elon Musk Pushed DOGE Up and BTC Down, With Arca's Jeff Dorman
3 Things SushiSwap Needs to Get in Order, According to Arca
Links
Market crash:
Unchained:
Ethereum Drops Below $2,300 Amid Jump Crypto Rumors
Bitcoin ETF Trading Volume Surges to $4.7 Billion Amidst Market Selloff
Bitcoin and Ethereum Funds Record $546 Million in Weekly Outflows: CoinShares
The Block: Cryptocurrency market capitalization registers largest daily drop since 2022
Japan
BBC: The Bank of Japan raises interest rates for second time this year
The Defiant: Here’s an ELI5 on on How Japan Sent Global Markets Tumbling
SEC:
Eleanor Terret’s tweet on the SEC’s funding
Unchained: Can Gary Gensler Be ‘Fired’ If Trump Becomes President Again?
Others:
The Block: Genesis completes bankruptcy restructuring, begins distributing $4 billion in crypto and cash
Poylmarket: US Presidential Elections odds
Learn more about your ad choices. Visit megaphone.fm/adchoices
Wall Street should market Ethereum as the crypto 'app store,' says Arca CIO Jeff Dorman
Jeff Dorman is Arca's Chief Investment Officer.
In this episode, Chaparro and Dorman discuss the recent approval of the spot ether ETFs and how it opens the door for institutional investors to engage with the Ethereum ecosystem.
The discussion also highlights the importance of regulatory clarity and the shifting sentiment towards crypto in Washington.
OUTLINE
00:00 Introduction
02:34 ETH ETF Approval
06:02 Wall Street Onchain?
12:05 ETH ETFs & Market Structure
17:53 ETH Headwinds & Underperformance
21:28 Altcoin ETFs?
25:27 Crypto's Crowded VC Landscape
34:32 Liquid Crypto Funds
41:47 Traditional Hedge Funds & Crypto
This episode is brought to you by our sponsor Polkadot
Polkadot is the blockspace ecosystem for boundless innovation. To discover more head to polkadot.network
The Block Community
The Block is launching a new community experience for fans of The Scoop! Follow us on Lens to stay in the loop: hey.xyz/u/theblockcommunity
The Block Newsletters
The Block's newsletters bring you the latest news and analysis of the fast-moving crypto and DeFi markets. To subscribe, visit theblock.co/newsletters
Crypto’s Next Chapter | Jeff Dorman
On today's episode of Empire, Jason and Santiago are joined by Jeff Dorman, CIO of Arca. Jeff is a prominent crypto investor known for his fundamental analysis, contrarian bets and ability to simplify crypto's arcane topics.
In this episode, Jeff explains crypto's response to macro, why fundamentals matter, equity tokenization, crypto's most exciting developments and more. Don't miss Jeff's insights on where crypto is headed next!
Resources:
BTC/NASDAQ correlation: https://www.bloomberg.com/news/articles/2022-04-11/bitcoin-s-correlation-with-big-tech-increases-to-record-chart
Follow Jeff on Twitter: https://twitter.com/jdorman81
Follow Empire on Twitter: https://twitter.com/theempirepod
--
ParaSwap:
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Timestamps
(00:00) Introduction
(01:27) The Real Reason Crypto Is Correlated To The NASDAQ
(04:27) Is The Fed In Control of Inflation?
(09:02) Crypto's Strength During Macro Turbulence
(13:04) The Ownership Narrative
(15:25) Everything Is Based On Trust
(18:12) Ownership and Aligned Incentives
(25:27) Liquidity Incentives
(30:28) Governance
(33:57) Paraswap Ad
(35:06) CeFi Merging With DeFi
(39:32) What Is Jeff Excited About?
(44:09) DeFi Is Boring But Works
(47:42) Tokens That Accrue Value
(49:50) Business Development in Crypto
(54:38) How To Value Layer One Blockchains
--
Disclaimer: Nothing said on Empire is a recommendation to buy or sell securities or tokens. This podcast is for informational purposes only, and any views expressed by anyone on the show are solely our opinions, not financial advice. Santiago, Jason, and our guests may hold positions in the companies, funds, or projects discussed.
Unconfirmed: 3 Things SushiSwap Needs to Get in Order, According to Arca - Ep.297
Jeff Dorman, the chief investment officer at Arca, discusses the recent events surrounding SushiSwap, including CTO Joseph Delong’s departure this week, Arca’s proposal to create a hierarchical management structure for SushiSwap, and why Jeff is still excited about Arca’s investment in SushiSwap. Show topics:
what SushiSwap is and how it has performed since its inception
how Jeff views SushiSwap’s performance from an investor’s perspective
how the departure of 0xMaki affected SushiSwap
what Jeff thinks about the decentralization versus centralization
why Jeff thinks SushiSwap is in a fantastic position in which to receive investment
what happened with the controversy around Joseph Delong leading to his resignation this week
what Jeff thinks about how Joseph handled his departure
what three factors SushiSwap needs to figure out in order to function
why SushiSwap could benefit from creating a legal entity
why Jeff is in favor of hierarchical governance structures versus flat governance structures
how SushiSwap could become a trendsetter for DAOs in general
Thank you to our sponsors!
Avado: ava.do
Crypto.com: https://crypto.onelink.me/J9Lg/unconfirmedcardearnfeb2021
Nodle: https://bit.ly/3AXGydJ
Episode Links:
Jeff Dorman
Twitter
https://twitter.com/jdorman81
Arca
https://www.ar.ca/
Joseph Delong’s Departure
The Block’s coverage:
https://www.theblockcrypto.com/post/126411/sushiswap-cto-threatens-to-quit-as-infighting-escalates
https://www.theblockcrypto.com/linked/126879/sushiswaps-cto-resigns-amid-infighting
The Defiant:
https://thedefiant.io/sushiswap-leadership-crisis/
Sushi Bickering on Twitter
Screenshot of 0xMaki being ousted:
https://twitter.com/makibacknow/status/1463078678724632576/photo/1
Joseph Delong on SushiSwap drama:
https://twitter.com/josephdelong/status/1467498481573052427
Joseph Delong’s resignation:
https://twitter.com/josephdelong/status/1468689021530427395
Boring Crypto on SushiSwap drama:
https://twitter.com/Boring_Crypto/status/1467162233905893379
SushiSwap Proposals
Arca
https://forum.sushi.com/t/sushi-dao-restructure-proposal/6282
Bridge compensation
https://forum.sushi.com/t/bridge-compensation-for-sushi-core/6217/3
Miscellaneous
0xMaki transitioning to an advisory role
https://forum.sushi.com/t/transition-into-advisor/5533
SushiSwap on leadership tumult
https://hackmd.io/ipJtfxhuQmqW9B8igew_AA?view
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"The Bull Market is Intact for the Next 10 to 20 Years; We are in a Secular Shift:" Arca's Jeff Dorman
In this week’s episode, I interview Jeff Dorman, chief investment officer at Arca, an investment management firm focusing on digital assets. Jeff has been valuing assets for the past 20 years, from investment-grade bonds, to high-yield debt and equities, and now he’s doing the same for crypto. We talk about the recent selloff and he thinks the big crash is over but that doesn’t mean we’ve seen the market bottom. Still, Jeff says this is a buying opportunity and he gives insights into which sectors will outperform and underperform. He believes we’re heading to a 10 to 20-year secular bull market in crypto, where there will be a decoupling of sectors and where DeFi continues to grow.
Big thanks to our sponsors:
Kyber, whose Dynamic Market Maker, or DMM, is designed to react to market conditions to optimize fees, maximize returns
Balancer, one of the leading DeFi automated market makers (AMM) for multiple tokens. Dive into their pools at https://balancer.finance/!
Enzyme provides an easy way to build, scale and monetize DeFi investment strategies
Kraken, consistently rated the best and most secure cryptocurrency exchange, which can get you from fiat to DeFi
Aave, an open source and non-custodial liquidity protocol where users can earn interest on deposits and borrow assets
Unconfirmed: How Elon Musk Pushed DOGE Up and BTC Down, With Arca's Jeff Dorman - Ep.237
Jeff Dorman, the chief investment officer at Arca, comes on the show to give a macro perspective on the crypto environment. In this episode, he discusses:
how economic data and real-world events have affected digital assets
how Jeff classifies the different types of assets within crypto
what market forces have pushed ETH to new all-time highs above $4k
whether EIP 1559 will have the same effect on ether price as the Bitcoin halving has on BTC price
what is happening with Dogecoin and other meme-coins
why the market’s reaction to Tesla’s halt of BTC vehicle purchases was healthy
whether environmental concerns surrounding Bitcoin will have long-term consequences on crypto as an asset class
Thank you to our sponsors!
Crypto.com: https://crypto.onelink.me/J9Lg/unchainedcardearnfeb2021
Tezos: https://tezos.com/discover?utm_source=laura-shin&utm_medium=podcast-sponsorship-unconfirmed&utm_campaign=tezos-campaign&utm_content=hero
NEAR: https://near.org
Episode Links
Jeff Dorman
Twitter
https://twitter.com/jdorman81
Arca
https://www.ar.ca/
Blog post titled “How Economic Data Affects Digital Assets”
https://www.ar.ca/blog/crypto-market-recap-05-10-21
Blog post titled “The Four Types of Digital Assets”
https://www.ar.ca/blog/crypto-market-recap-06-29-20
Miscellaneous Links
Dogecoin SNL clip
https://www.youtube.com/watch?v=x5RCfQyTDFI
SHIB token + dog meme-coins
https://decrypt.co/70587/shiba-inu-shib-what-why-price-dogecoin
https://www.theblockcrypto.com/post/104676/vitalik-buterin-donates-more-than-60m-to-charity-after-selling-meme-tokens-including-shiba-inu
https://twitter.com/lawmaster/status/1392533724814876680/photo/1
Nic Carter on Bitcoin mining
https://www.coindesk.com/the-last-word-on-bitcoins-energy-consumption
Tesla’s announcement on halting BTC vehicle purchases
https://twitter.com/elonmusk/status/1392602041025843203
Link to the Crypto News Recap:
https://unchainedpodcast.com/why-an-elon-tweet-sent-bitcoin-below-50k/
Learn more about your ad choices. Visit megaphone.fm/adchoices
SotN #43 Coinbase Goes Direct | CIO of Arca Jeff Dorman
In this week's State of the Nation, we bring on Jeff Dorman, Chief Investment Officer and Arca, to measure the magnitude of $COIN on the public markets.
State of the Nation is live-streamed on Tuesdays at 11am PST.
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State of the Nation #43: Coinbase Goes Direct Guest: Jeff Dorman
Jeff Dorman is Chief Investment Officer at Arca, the digital asset management firm. Jeff leads the investment committee, focusing on risk management for cryptoassets. His work history in both legacy and crypto finance puts him in a unique position to work as a bridge between the two worlds.
The Coinbase Direct Listing also acts as a bridge between the two worlds, and it's undoubtedly a landmark event for the legitimization of the crypto industry. What does this mean for the Banks, Fintech, and Wall Street? What does it mean for Gemini, Uniswap, and Binance?
The first item to discuss to answer these questions is how the media and crypto twitter alike were off in their interpretation of this event. The volatile price action in the first moments of the listing were surprising to many, but Jeff explains that this shouldn't be surprising at all, given that there are no underwriters or built-in stability in a direct listing like $COIN's. He expects that there will be volatility and price discovery over a longer stretch of time before the stock moves to a more stable valuation.
------
Resources:
Jeff's Article on Coinbase: https://www.ar.ca/blog/crypto-market-recap-02-28-21
Arca: https://www.ar.ca/
Jeff on Twitter: https://twitter.com/jdorman81?s=20
$COIN Price https://www.tradingview.com/chart/?symbol=NASDAQ%3ACOIN
Coinbase S1 Filings: https://www.sec.gov/Archives/edgar/data/1679788/000162828021003168/coinbaseglobalincs-1.htm
Coinbase Analytics: https://www.theblockcrypto.com/data/crypto-markets/public-companies
------ This Week on Bankless:
📛 Bankless Badge Week (4/20): https://newsletter.banklesshq.com/p/how-to-win-free-stuff-with-your-bankless 📈 Market Monday (4/19): https://newsletter.banklesshq.com/p/6-tips-to-succeed-in-this-bull-market 📖 Before Bitcoin (4/19): https://shows.banklesshq.com/p/-before-bitcoin-pet3rpan 🧢 Weekly Action Recap (4/17): https://newsletter.banklesshq.com/p/price-discovery-mode-weekly-recap 🗞️ Weekly Rollup (4/16): https://shows.banklesshq.com/p/-rollup-btc-and-eth-ath-coin-berlin
----- Not financial or tax advice. This channel is strictly educational and is not investment advice or a solicitation to buy or sell any assets or to make any financial decisions. This video is not tax advice. Talk to your accountant. Do your own research.
Disclosure. From time-to-time I may add links in this newsletter to products I use. I may receive commission if you make a purchase through one of these links. Additionally, the Bankless writers hold crypto assets. See our investment disclosures here: https://newsletter.banklesshq.com/p/bankless-disclosures