Bitcoin Treasuries: The Bubble That Will Redefine Wall St.
ZK's declassified survival guide for Bitcoin Treasury companies.
An old trading buddy hit me up, he was facing a the âtoughest decisionâ of his life⌠He has a shiny big-bank resume with 20+ years of experience trading structured products, we spent a lot of long days grinding on a sell-side convertibles desk focused on oil and bulk commodities. Heâs sharp but never was motivated to understand Bitcoin beyond what most old-school Wall St. traders skim, and now heâs been offered a CEO gig at one of these âBitcoin treasury companies.â He called me âcause Iâve been a student of BTC for over a decade now and would briefly talk about Bitcoin from time to time on the desk back then. He also knew I gave up everything I worked for on Wall St. a few years ago because I believed in Bitcoin more. He wanted the real deal: are these companies legit or a bubble about to pop? That call made me dig back into my Series 86/87 research analyst days to break down whatâs going on in this sector. Iâve worn many hats on Wall Str and seen the sausage factory up closeâ I started as a young stock broker making 500 calls a day off shit D&B leads and ended up many years late working buy-side at a large family office as a Portfolio Analyst. I left because Bitcoin is the incorruptible asset and exposed the cracks in the system, not because I hated Wall St.
Back in the early 2010s, Bitcoin was a dirty little secret if you were a finance bro. Iâd commit keyboard shortcuts to memory and practice - ready to flip tabs if compliance or a a co-worker stretching his neck to make sure no one saw my crypto charts and news tabs. Bitcoin wasnât just misunderstoodâit was taboo, mocked as a playground for drug dealers and criminals. If you didnât live through those days, you canât grasp how insane the shift has been. Fast forward to August 2025, and Bitcoinâs the sexiest asset on the Streetâpublic companies hold ~962,983 BTC, ~5% of supply, with institutions piling in and retail ready to FOMO. But cut the bullshit: is this what main stream adoption looks like? Wall Street missed the boat and now theyâre leeching onto Bitcoinâs gravity, scrambling to catch up / avoid under-perfomance. The real story? Bitcoinâs forcing finance to rewrite its rulesâcash ainât king; itâs a liability. Saylor saw it first and was thus rewarded, now the rest are figuring it outâŚAs Wall Street deregulates and Bitcoin gets more âregulatedâ, they wonât meet in the middle. Theyâll spawn a new way to size up companies that will evolve corporate balance sheets, metrics, and what âvalueâ even means.
For my buddy, I broke down the treasury meta: how we got here (Saylorâs as a prereq), where weâre at, where itâs going, and hard advice for any CEO stepping into the ring. Two mandates: maximize shareholder value (legally) and specalize to survive. No financial advice hereâmy FINRA licenses are long expiredâbut this is the unfiltered take from a unique perspective of someone who intimately knows both worlds (Crypto and Wall St) that are now joining as oneâŚ.
The MicroStrategy Playbook: Saylorâs 4D Chess
Bitcoin treasuries start with Michael Saylor and MicroStrategy (MSTR). Iâm sticking with âMicroStrategyâ as a silent protest on their pointless corpo rebrand. Saylorâs not just the face; heâs the mastermind, a public market cockroach (respectfully) who outlasted the dot-com crash as a tech CEO. That ainât a flexâitâs real signal. His peers from that era? All Wiped out except Bezos and the dozen or so others you knowâŚ. Saylorâs scars give him a systems-thinking edge no MBA or AI can match. Heâs seen markets implode, colleagues get rekt, and built MSTR with reserves and balance sheet to handle volatility and eventually consolidation. You canât fake that this dude has been reporting to his shareholders every quarter for over two decadesâŚ.
Contrarian Take #1: You Canât Copy Saylor. MSTR wasnât born a Bitcoin treasuryâit was a washed-up software firm, bleeding relevance, hammered by shorts (check the pre-2020 chart). Saylor didnât raise capital to chase Bitcoin; he pivoted to survive, hedging fiat risks and tech competition. In 2020, he was the true contrarian, stacking BTC at $10kâ$20k while dodging regulatory headaches before the SEC chilled out. That first-mover edge gave him a massive, cheap stackâ628,791 BTC as of August 2025, ~65% of public holdingsâand a cult-like following. He bought in quiet markets (buy quiet, sell noisy as Wall St saysâŚ), risks that paid off huge and that no one will be able to copyâŚ
What was Saylor really selling though? As a former derivatives trader whoâs spent a lot of time on a capital markets desk, I see his playbook like looking at a X-ray. He mastered Bitcoin before layering leverage, timing each phase and product with Bitcoinâs moves and the markets pyscheeâŚ
Bitcoin Proxy Phase (2020â2021): Pre-ETFs, pre-crypto IPOs, Saylor sold MSTR as the clean way for mandate-constrained institutions to get Bitcoin exposure without touching it. He wasnât pitching his outdated softwareâhe was evangelizing BTC, carving out the first real way for wall st firms to get BTC exposure. Roadshows, podcasts, relentless PRâhis bet on Bitcoinâs rise paid off as MSTR rocketed with BTCâs surge. The publicity helped ensure the raises were oversubscribed / always new buyers comingâŚ
Equity Flywheel Phase (2021â2022): Bitcoin explodes, Saylor pivots. He issues MSTR equity at premium valuations to buy more BTC, stacking sats in a loop. This gave birth to the treasury playbook idea and sketchy non-GAAP metrics like âBitcoin per shareâ and âBitcoin Yieldâ. MSTR outperformed, but was it genius or was it Bitcoinâs pump plus constrained capital? That edge isnât foreverâETFs and blue-chips with BTC exposure will eat it.
Treasury Gospel Phase (2022â2023): Saylor stops focusing on selling stock primarilyâheâs selling the idea of Bitcoin treasuries. Decks flaunt MSTRâs gains against NVIDIA, offering blueprints for equity raises to buy BTC. Bankers salivate over fees, the SECâs softening fuels reverse mergers, and crypto S-1s multiply. Every pitch deckâs got MSTRâs chart and a Saylor fan pic⌠good work summer banking internsâŚ
Prefs and Financialization Phase (2024âPresent): Saylorâs boldest moveâpivoting MSTR into a financial entity with preferred stock issuances, targeting fixed-income markets (high-yield, investment-grade, for institutions, not retail degens). His 2.5-4x NAV ceiling signals covered-call spots, capping relative common equity upside and introducing conflicts for shareholders. Convertible holders mightâve jumped at prefs earlier, but Saylorâs playing 4D chess, locking down BTC collateral while offering better credit/rates than copycats. Is Saylor being Hypocritical? Issuing fiat-yielding securities in a Bitcoin world? Sure, it kinda goes against what he was preaching for a while ? But itâs progress towards a more sustainable finance world and getting a step closer to DeFi being in TradFi clothes, forcing Wall Street toward crypto logicâ his prefs are like a DeFi protocol but instead of hard code its on a soft mutable prospectus.
Saylorâs timingâBitcoin, equity, treasurie playbook, prefsâmakes him the apex predator. Heâs paid billions in banker fees, and every bulge-bracket MD is shilling his playbook to the next wannabe treasury CEO. Learn from Saylor, but you will not be able to copy .
The Current Meta
Weâre at the brink of the Bitcoin treasury explosion. As of August 2025, the top 100 public companies hold ~962,983 BTCâ5% of supplyâwith MSTR dominating at 628,791. However, I think many are underestimating actual volatility and seasonality in capital markets. Deals oversubscribe in euphoria, dry up in bloodbathsâlook at the SPAC bubble, this will be bigger. Bankers chase fees, institutions snag discounts, retail gets red candles.
Contrarian Take #2: Easy Modeâs Over. The low-hanging fruitâissuing equity at premiums to buy Bitcoinâis vanishing. Bitcoinâs cyclical, driven by halvings (read the whitepaper if you think cycles are dead). Itâs seen 70% drawdowns, and theyâre coming again most likely. Issuing stock at discounts during a bear market? Death spiral. You buy less Bitcoin, dilute shareholders, tank your stock. Incentives skew hard: bankers get fees, whales get cheap shares, retail gets rekt. Shorts are circling, sniffing bloated management teams, excessive stock comp, and murky governance. Who will be the first public CEO to click a wallet drainer link? that would be a ugly open I bet. 80% of ETF Bitcoin sits on Coinbaseâcentralization risks are real. Bitcoin treasury risk are bringing a bit more systemic risk to crypto but Bitcoin will only get stronger in the end.
Competitionâs brutal. Bitcoin ETFs, soon to be in-kind redemption increasing, and blue-chips adding Bitcoin to balance sheets (imagine Pfizer with 50% cash in BTC) erode the treasury value prop. Why buy a treasury stock when you can get an ETF or a diversified giant with Bitcoin exposure? Miners? Theyâre the purest play for leverage exposure, generating Bitcoin via the network daily, but face energy costs (AIâs eating powerâZuckâs tent data centers arenât helping), location risks, and inventory headaches. I expect a wave of clean energy subsidization for Bitcoin miners coming soon, there is a Trump on a board of a US mining company already⌠Treasury companies that donât contribute to Bitcoinâs network are just middlemen in a system built to cut them out.
Why Treasuries Exist at All
No orange juice or coal treasury companiesâwhy? Storage costs, decay, transport, and the SEC didnât box the other commodity exposed companies out of capital markets. Bitcoinâs uniqueâborn in our lifetime, with demand exploding via regulatory arbitrage and constrained capital pools looking for more return. US investors lack exposure to small-cap crypto firms compared to offshore markets, a product of Gary Gensler depriving folks of any crypto-related assets. I spent something like 10+ months in 2019 trying to get an S-1 throughâafter 6 rounds of lengthy comments, we gave up and listed on an offshore exchange. Treasuries fill that gap, a reaction to years of SEC crackdowns. But as regulation softens, their edge dulls. Merchants holding Bitcoinânot auto-swapping like SteakâNâShakeâsignal true adoption. Until then, treasuries are a bridge, but a shaky one. These products shine for capital-constrained pools, mandate-confined institutions, or for retail chasing income/leverage on Bitcoin. For most reading this? Straight self-custody Bitcoin is the moveâno middlemen, no dilution, just pure exposure and owning Bitcoin the way Satoshi intended.
Where Itâs Going: A Bubble on the Best Asset Ever
This is a bubble, but itâs built on Bitcoinâthe strongest underlying known asset to man, not tulips or Beanie Babies. Volatility drives adoption; Bitcoin emerges stronger from every crash. But consolidations inevitable, and Saylor set the trap with prefs. The weak players will fold or get acquired at discounts (stock-for-Bitcoin deals, premium to daily share price but below NAV). Survivors must innovate beyond âraise equity, buy Bitcoin.â
Contrarian Take #3: Intrinsic Bitcoin Creation Is the Future. Holding Bitcoin isnât enoughâgenerate it operationally. This is the golden metric: how much Bitcoin a company generates organically without burning cash or issuing stock. Miners nail it by securing the network and earning Bitcoin daily, treasuries should pivot here too. Why? It boosts network value (harder to attack), hedges energy risks (AI's power demand will keep ramping), and creates sustainable bitcoin exposure that market can predict/model out long term. Without it, you're just a glorified ETF with corporate overhead. Another path: acquisitions. Use stock in euphoric markets to buy cash-flowing businessesâthink commodity extractors with stable long term off-take agreements with big counterparties (gold, oil, iron ore etc). These deals, done with stock during market euphoria, can diversify revenue streams and hedge against Bitcoinâs volatility, creating a more desirable position for your equity holders (multiple shots on goal, optionalty with cash flow).
Preferred stock? A trap for most. Only MSTR or giants like Tether can pull off high-yield, investment-grade products with competitive yields and credit profiles. Smaller players issuing prefs will face short attacks, worse yields, and prospectus changes under pressure. Governance is a minefieldâevery non-Bitcoin expense (stock options, bloated teams, exec comp) is a short target. And donât forget custody risks. The first public company to lose Bitcoin to a hack or scam will be a cautionary taleâŚ
Altcoin Treasuries? Doomed to Flip. The game theory here is simple: as altcoin treasuries chase staking yields, the BTC/alt ratio will keep climbing, forcing them to add Bitcoin or flip entirely to stay competitive. Public markets reward rational movesâsell POS (proof-of-stake or piece of shit, depending on your sats stack) for POW. One shitcoin treasury company with a 8-K announcing a flip to BTC, the stock rerates overnight, then all will follow. Altcoin holders also face pressure from the Eth foundation selling and weaker fundamentals; Bitcoinâs the king. Why hold a treasury betting on ETH or Solana when BTCâs the proven store of value? Altcoin treasuries will ultimately help Bitcoin by drawing more capital into Bitcoin after they flee for safety from their proof of stake networks.
What is the bigger picture? This treasury meta is hinting at Bitcoin's rewrite of financeâcash as liability, Bitcoin accrual as the new north star. But I save the full punch for the end.
Advice for the CEO Chair: Survive, Specialize, or Sink
My friendâs call wasnât casualâit was about his life, his senior career pivot. I told him: if you take this CEO job, youâre stepping into the matrix where Wall Streetâs revolving door meets Bitcoinâs cycles. Itâs high-stakes, but hereâs the unfiltered breakdown to shift your perspective from âeasy moneyâ to âbuild or bust.â Iâve structured convertibles during oil crashes, seen death spirals firsthandâsame traps await mistimed raises. Every CEO reading this: rethink your playbook now, or get consolidated.
Ditch the âTreasuryâ LabelâRebrand as Bitcoin-Centric: Stop sounding like a one-dimensional bubble. Why? Itâs short-term hype; investors want sustainability. Emphasize intrinsic Bitcoin creationâmining, on-chain infrastructure, renewable energy projects etcâto align with the networkâs growth, not just BTC price pumps. This shifts you from middleman to network contributor, boosting long-term value and dodging the âglorified ETFâ label.
Acquire Cash-Flowing AssetsâDiversify or Die: Use stock to buy stable, inflation-hedging businesses like traditional metals and mining companies with off-take agreements. Why? One-off Bitcoin purchases dilute in drawdowns; cash flows hedge cycles and scale like institutional DCA. How? Target unloved commodities for all-stock deals during market euphoriaâgold miners dipping into BTC make for great irony (Peter Schiff advising?). This reduces reliance on equity raises, builds a war chest, and positions you as the acquirer in consolidation, not the prey. Stop chasing Bitcoin per share; chase Bitcoin flow. Thatâs the difference between leaderboard bragging and surviving the cycleâŚ
Avoid the Pref Trap Unless Youâre Saylor-Scale: Issuing preferred stock is suicide for mostâworse yields, weaker credit profiles. Why? You wonât beat MSTRâs terms; it invites short attacks and dilutes common shareholders. How? Focus on transparent equity timed carefully or skip complex instruments altogether, ensuring any layering supports intrinsic creation, not fiat yields. This will likely only work for MSTR and big financial/insurance players down the roadâany reverse merger BS with a CEO whoâd click a wallet drainer link wonât get a better credit profile or sustain higher-yielding paper than whats on Saylorâs menu. Prefs are a consolidation trapâSaylorâs using them to dominate fixed income; youâll just cannibalize yourself trying to compete.
Survive Volatilityâ Bitcoinâs 70% drawdowns are real and not over. Mistimed capital raises become death spirals if done at discounts, with performance chasers rotating out at the first red candle. How? Build a war chest for opportunistic buys, time issuances around halving ramps, and minimize time before you actually own the Bitcoin. Loyaltyâs fleeting; conviction comes from understanding edges the market doesnât see yet, not historical performance.
Lock Down GovernanceâBe Lean or Get Eaten: Shorts feast on bloatâexcessive comp, murky custody, correlated ownership. Why? Every expense not tied to buying or generating Bitcoin is a target for shorts, and this will force strict transparency and accountability around typical corporate BS. How? Transparent Bitcoin holdings, ironclad custody, no options slush fundsâprove youâre not a SPAC 2.0. Youâre building for Bitcoinâs network, not Wall Street feesâgovernance is your moat in the coming bubble burst.
Conclusion: Bitcoinâs the King, Rewriting Finance Forever
Saylorâs shown whatâs possible, but strategy is not a template. The Bitcoin treasury meta is Wall Streetâs desperate grab at Bitcoinâs rise, fueled by Genslerâs crackdowns that deprived US investors of crypto exposure. But itâs a sideshow to the real revolution: Bitcoinâs forcing a total rewrite of the financial system. Forget EBITDA or free cash flowâcompanies wonât be valued on fiat metrics anymore once the dust settles, but on intrinsic Bitcoin generation: how much Bitcoin you mine, acquire, or flow without dilution. Balance sheets become liabilities; game theory will force Bitcoin into 2â100% of long-term cash reserves for every public company. Metrics like mNAV? Bitcoin per share ? Pure imaginationâno hard rules between NAV and equity value, unlike closed-end funds where it actually matters. Exotic derivatives ( ratchets, resets, unit deal, warrants, rights issues, convertible lines of credit etc) will ramp as the market extends, discounts will deepen in winters, and short attacks will get violent. Self-custody Bitcoin cuts through the noiseâfor most, owning Bitcoin straight trumps treasuries stocks, especially if youâre not mandate-confined or chasing leverage/income.
This meta, born from Genslerâs chokeholds, is birthing a new order: decentralized scarcity over centralized fiat. Wall Street deregulates, Bitcoin gets âregulatedââthey will not meet in the middle but spawn a new beast of how to value stocks. Treasuries bridge the gap, but Bitcoinâs the coreârewriting rules, busting models, forcing finance to bend the knee.
For my friend, I didnât say take the job or notâIâm just going to send him thisâŚ.Bitcoin CEOâs will be the major incremental demand driver the next few months, they will determine the cycleâŚ
- Thanks for reading. Iâve been busyâŚ.
Parasite