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Saylor may sell Bitcoin to fund MicroStrategy's 11.5% yield product

Wednesday, May 13, 2026 · from 3 podcasts
TFTCPresidio Bitcoin JamBankless
  • MicroStrategy may sell Bitcoin to fund dividends for its new high-yield STRC security, a major strategic pivot.
  • Bitcoin's correlation with the Nasdaq hits record highs, eroding its digital gold appeal for a tech stock tailwind.
  • Block fuels adoption via 5% Bitcoin-back rewards, using incentives to bypass consumer education.

Michael Saylor’s 'never sell' Bitcoin doctrine is officially over. On recent earnings calls, the MicroStrategy chairman revealed the company may sell portions of its massive treasury to fund dividends for its new preferred shares, called the Stretch (STRC) security. It's a move to optimize the balance sheet and potentially satisfy ratings agencies for S&P 500 inclusion. The new product offers an 11.5% yield, secured by Bitcoin collateral.

"The mechanics of the Stretch product rely on massive over-collateralization. The product is roughly six times collateralized, meaning Bitcoin would need to collapse by 80% and stay there for years to break the model."

- Host DK, Presidio Bitcoin Jam

As Presidio Bitcoin Jam hosts note, the goal isn't retreat but optimization: selling Bitcoin bought at $10,000 to pay dividends while the price sits above $60,000 increases Bitcoin per share. This turns MicroStrategy into a quasi-decentralized bank using Bitcoin as collateral. On Bankless, David Hoffman warns this arbitrage model assumes Bitcoin's price rises forever; if market growth stalls, the main treasury could become a source of forced selling.

Bitcoin’s role as an independent asset is also fraying. On Bankless, Ryan Sean Adams noted the correlation between BTC and the NASDAQ hit 0.48 this week, a record high. Bitcoin is now acting as a high-beta tech play, trailing the AI boom's tailwinds instead of serving as a monetary shield.

"Crypto natives often have 90% of their net worth in the asset, making every price swing a survival event. In contrast, the 'Vanguard mentality' creates a marriage between the investor and the fund."

- Eric Balchunas, TFTC: A Bitcoin Podcast

Meanwhile, as Eric Balchunas argued on TFTC, a new, more resilient class of buyer is emerging: the boomer investor allocating 1-2% through ETFs like BlackRock’s IBIT. This institutional rotation is so pronounced that over the last 16 months, corporations and ETFs bought one million Bitcoin while individuals sold 750,000. The next phase, Balchunas says, is the 'Jepi-ization' of Bitcoin - Goldman Sachs and BlackRock have filed for Bitcoin equity premium income ETFs to generate yield, targeting income-hungry traditional finance.

While Wall Street engineers yield, Block is engineering adoption through frictionless incentives. As detailed on Presidio Bitcoin Jam, Block’s 5% Bitcoin-back reward for payments via Cash App at Square terminals bypasses education, turning merchants and users into stackers by default. The strategy makes Bitcoin a daily-use product, not an ideological project.

#BTC Markets#Adoption
Michael SaylorBlackRockMicroStrategySquareBitcoinCash AppWall Street

Source Intelligence

- Deep dive into what was said in the episodes

TFTC: A Bitcoin Podcast
TFTC: A Bitcoin Podcast

Marty Bent

#743: Why Boomers Will OutHODL You with Eric Balchunas • May 10

  • Eric Balchunas asked Michael Saylor how to keep the cypherpunk base engaged as Bitcoin rapidly integrates with banks and government entities. He compared losing the core audience to how the Star Wars sequels lost their fanbase.
  • Balchunas cited data that over 16 months, about 1 million Bitcoin were bought by corporations, governments, and ETFs, while 750,000 were sold by individuals.
  • Balchunas argues Bitcoin’s core appeal for new ETF investors is its scarcity and role as a debasement hedge, not its censorship-resistant properties. This fundamental value is what drives long-term allocation, not short-term headlines.
  • Despite a 50% price drawdown, Bitcoin ETFs have shown resilience, with cumulative net flows nearly recovering their pre-drawdown peak of $62 billion. Balchunas notes only Vanguard funds typically see inflows during negative performance.
  • BlackRock’s iShares Bitcoin Trust was the 11th highest ETF for inflows in April with $2.3 billion, a rare feat for an asset with negative year-to-date returns.
  • Balchunas argues much of the price appreciation for Bitcoin’s Wall Street and government adoption was front-run during a 450% rally from 2022-2023, making current headlines less impactful.
  • Marty Bent notes that per capita Bitcoin adoption is highest in mismanaged countries with decent tech literacy, citing Venezuela as a leading example from a 2019 study.
Also from this episode: (3)

Protocol (3)

  • Balchunas predicts a brokerage fee war for Bitcoin trading, similar to when Schwab and Fidelity drove stock commissions to zero. He gives this a 95% chance of happening by year-end.
  • The key new ETF products to watch are Bitcoin premium income funds from Goldman Sachs and BlackRock. These 'boomer candy' products trade upside for downside protection and income.
  • Balchunas sees Bitcoin and gold eventually coexisting like 'step-brothers,' as they share a fundamental sound money thesis and compete for the same portfolio allocation.
#ETFs#BTC Markets#Adoption#Macro#Banking
Presidio Bitcoin Jam
Presidio Bitcoin Jam

Saylor to sell bitcoin, Block earnings beat, Anthropic partners with xAI • May 8

  • Cash App now offers 5% Bitcoin rewards on payments made through Square terminals.
  • A restaurant owner's transition from reluctance to enthusiasm for Bitcoin payments demonstrates how default adoption and regular usage drive acceptance.
  • Steve proposed MoTips, a Bitcoin-based tipping system for service workers, to solve the friction of digital tipping and convert workers into Bitcoin advocates.
  • MicroStrategy's strategic pivot includes retaining the ability to sell Bitcoin, a move described as rational to strengthen their financial toolkit and reduce arbitrage risks.
  • Saylor claims 80% of demand for MicroStrategy's stretch notes is retail, indicating the product is viral but not yet widely adopted by institutional funds.
  • Steve argues the fundamental risk for MicroStrategy's model is long-term Bitcoin price stagnation; the structure is safe if Bitcoin appreciates more than the dividend yield over time.
  • DK distinguishes MicroStrategy from Terra Luna by its high over-collateralization, corporate governance, and the fact that shareholders cannot directly redeem the underlying Bitcoin.
  • DK's names protocol uses Bitcoin bonds and auctions to create a credibly neutral, issuer-free naming system, solving the problems of central control, name squatting, and annual fees.
Also from this episode: (6)

Protocol (2)

  • DK's friend, an e-commerce founder, was unaware of MicroStrategy's stretch product and immediately wanted to incorporate its 11.5% yield into his treasury operations.
  • Block's Cash App gross profit grew year-over-year, with the company highlighting gross profit as a key metric because revenue is distorted by Bitcoin trading volume.

Nostr (1)

  • Wave Lake and Fountain are hosting music on Nostr, and DK found a track he rated 10/10, signaling a shift from novelty content to quality music on the platform.

AI & Tech (1)

  • DK built the naming system prototype using Codex AI as a technical partner, allowing him to implement a complex economic system without deep prior Bitcoin programming expertise.

Enterprise (1)

  • Jack Dorsey indicated Block is evolving into an intelligence company during the earnings call, signaling a strategic shift beyond its current financial products.

Science (1)

  • Steve takes magnesium supplements nightly, citing a recommendation from Lynn Holden and noting its life-changing effects due to depleted soils in modern agriculture.
#Macro#BTC Markets#Payments#Banking
Bankless
Bankless

ROLLUP: Crypto’s Nasdaq Problem | The CLARITY Act | Saylor Selling? | ETH L1 Scaling • May 8

  • Bitcoin's correlation with the NASDAQ hit 0.48 in 2026, the highest ever, making it a lagging proxy for stock market moves.
Also from this episode: (8)

Protocol (4)

  • Michael Saylor publicly stated he may sell Bitcoin to pay dividends for MicroStrategy's capital structure, contradicting his 'never sell Bitcoin' stance.
  • Arbitrum DAO faces a U.S. court restraining order over 31,000 ETH recovered from North Korean hackers, due to unrelated terrorism judgment claims.
  • The Ethereum Glamsterdam upgrade will increase max block space from 60 million to 200 million gas, projecting a 7x L1 throughput increase in 12 months.
  • The strategic Bitcoin Reserve may be formally implemented via centralized storage and an audit framework, not new purchases.

Big Tech (1)

  • Coinbase laid off 14% of its staff, marking a typical cycle bottom signal, while crypto VC funds raised $6.2 billion for infrastructure and tokenization.

Stablecoins (1)

  • The Clarity Act compromise restricts stablecoin yield if it resembles bank deposits, but allows rewards for activity like staking or market making.

Macro (1)

  • U.S. federal debt held by the public reached 100% of GDP, matching 1946 wartime levels, while the S&P 500 reported a sixth quarter of double-digit earnings growth.

Markets (1)

  • Berkshire Hathaway holds $400 billion cash after 14 consecutive quarterly sales, reflecting Warren Buffett's view that stocks are expensive.
#BTC Markets#Macro#Regulation#Stablecoins