An old trading buddy hit me up, he was facing a the “toughest decision” 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. He’s sharp but never was motivated to understand Bitcoin beyond what most old-school Wall St. traders skim, and now he’s been offered a CEO gig at one of these “Bitcoin treasury companies.” He called me ‘cause I’ve 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 what’s going on in this sector. I’ve worn many hats on Wall Str and seen the sausage factory up close— 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. I’d 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 wasn’t just misunderstood—it was taboo, mocked as a playground for drug dealers and criminals. If you didn’t live through those days, you can’t grasp how insane the shift has been. Fast forward to August 2025, and Bitcoin’s the sexiest asset on the Street—public 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 they’re leeching onto Bitcoin’s gravity, scrambling to catch up / avoid under-perfomance. The real story? Bitcoin’s forcing finance to rewrite its rules—cash ain’t king; it’s a liability. Saylor saw it first and was thus rewarded, now the rest are figuring it out…As Wall Street deregulates and Bitcoin gets more “regulated”, they won’t meet in the middle. They’ll spawn a new way to size up companies that will evolve corporate balance sheets, metrics, and what “value” even means.

For my buddy, I broke down the treasury meta: how we got here (Saylor’s as a prereq), where we’re at, where it’s going, and hard advice for any CEO stepping into the ring. Two mandates: maximize shareholder value (legally) and specalize to survive. No financial advice here—my FINRA licenses are long expired—but 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 one….

The MicroStrategy Playbook: Saylor’s 4D Chess

Bitcoin treasuries start with Michael Saylor and MicroStrategy (MSTR). I’m sticking with “MicroStrategy” as a silent protest on their pointless corpo rebrand. Saylor’s not just the face; he’s the mastermind, a public market cockroach (respectfully) who outlasted the dot-com crash as a tech CEO. That ain’t a flex—it’s real signal. His peers from that era? All Wiped out except Bezos and the dozen or so others you know…. Saylor’s scars give him a systems-thinking edge no MBA or AI can match. He’s seen markets implode, colleagues get rekt, and built MSTR with reserves and balance sheet to handle volatility and eventually consolidation. You can’t fake that this dude has been reporting to his shareholders every quarter for over two decades….

Contrarian Take #1: You Can’t Copy Saylor. MSTR wasn’t born a Bitcoin treasury—it was a washed-up software firm, bleeding relevance, hammered by shorts (check the pre-2020 chart). Saylor didn’t 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 $10k–$20k while dodging regulatory headaches before the SEC chilled out. That first-mover edge gave him a massive, cheap stack—628,791 BTC as of August 2025, ~65% of public holdings—and a cult-like following. He bought in quiet markets (buy quiet, sell noisy as Wall St says…), risks that paid off huge and that no one will be able to copy…

What was Saylor really selling though? As a former derivatives trader who’s 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 Bitcoin’s moves and the markets pyschee…

• Bitcoin Proxy Phase (2020–2021): Pre-ETFs, pre-crypto IPOs, Saylor sold MSTR as the clean way for mandate-constrained institutions to get Bitcoin exposure without touching it. He wasn’t pitching his outdated software—he was evangelizing BTC, carving out the first real way for wall st firms to get BTC exposure. Roadshows, podcasts, relentless PR—his bet on Bitcoin’s rise paid off as MSTR rocketed with BTC’s surge. The publicity helped ensure the raises were oversubscribed / always new buyers coming…
• Equity Flywheel Phase (2021–2022): 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 “Bitcoin per share” and “Bitcoin Yield”. MSTR outperformed, but was it genius or was it Bitcoin’s pump plus constrained capital? That edge isn’t forever—ETFs and blue-chips with BTC exposure will eat it.
• Treasury Gospel Phase (2022–2023): Saylor stops focusing on selling stock primarily—he’s selling the idea of Bitcoin treasuries. Decks flaunt MSTR’s gains against NVIDIA, offering blueprints for equity raises to buy BTC. Bankers salivate over fees, the SEC’s softening fuels reverse mergers, and crypto S-1s multiply. Every pitch deck’s got MSTR’s chart and a Saylor fan pic… good work summer banking interns…
• Prefs and Financialization Phase (2024–Present): Saylor’s boldest move—pivoting 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 might’ve jumped at prefs earlier, but Saylor’s 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 it’s progress towards a more sustainable finance world and getting a step closer to DeFi being in TradFi clothes, forcing Wall Street toward crypto logic— his prefs are like a DeFi protocol but instead of hard code its on a soft mutable prospectus.

Saylor’s timing—Bitcoin, equity, treasurie playbook, prefs—makes him the apex predator. He’s 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

We’re at the brink of the Bitcoin treasury explosion. As of August 2025, the top 100 public companies hold ~962,983 BTC—5% of supply—with 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 bloodbaths—look at the SPAC bubble, this will be bigger. Bankers chase fees, institutions snag discounts, retail gets red candles.

Contrarian Take #2: Easy Mode’s Over. The low-hanging fruit—issuing equity at premiums to buy Bitcoin—is vanishing. Bitcoin’s cyclical, driven by halvings (read the whitepaper if you think cycles are dead). It’s seen 70% drawdowns, and they’re 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 Coinbase—centralization risks are real. Bitcoin treasury risk are bringing a bit more systemic risk to crypto but Bitcoin will only get stronger in the end.

Competition’s 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? They’re the purest play for leverage exposure, generating Bitcoin via the network daily, but face energy costs (AI’s eating power—Zuck’s tent data centers aren’t 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 don’t contribute to Bitcoin’s network are just middlemen in a system built to cut them out.

Why Treasuries Exist at All

No orange juice or coal treasury companies—why? Storage costs, decay, transport, and the SEC didn’t box the other commodity exposed companies out of capital markets. Bitcoin’s unique—born 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 through—after 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 Bitcoin—not auto-swapping like Steak’N’Shake—signal 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 move—no middlemen, no dilution, just pure exposure and owning Bitcoin the way Satoshi intended.

Where It’s Going: A Bubble on the Best Asset Ever

This is a bubble, but it’s built on Bitcoin—the 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 “raise equity, buy Bitcoin.”

Contrarian Take #3: Intrinsic Bitcoin Creation Is the Future. Holding Bitcoin isn’t enough—generate 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 businesses—think 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 Bitcoin’s 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 minefield—every non-Bitcoin expense (stock options, bloated teams, exec comp) is a short target. And don’t forget custody risks. The first public company to lose Bitcoin to a hack or scam will be a cautionary tale…

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 moves—sell 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; Bitcoin’s the king. Why hold a treasury betting on ETH or Solana when BTC’s 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 finance—cash 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 friend’s call wasn’t casual—it was about his life, his senior career pivot. I told him: if you take this CEO job, you’re stepping into the matrix where Wall Street’s revolving door meets Bitcoin’s cycles. It’s high-stakes, but here’s the unfiltered breakdown to shift your perspective from “easy money” to “build or bust.” I’ve structured convertibles during oil crashes, seen death spirals firsthand—same traps await mistimed raises. Every CEO reading this: rethink your playbook now, or get consolidated.

1. Ditch the “Treasury” Label—Rebrand as Bitcoin-Centric: Stop sounding like a one-dimensional bubble. Why? It’s short-term hype; investors want sustainability. Emphasize intrinsic Bitcoin creation—mining, on-chain infrastructure, renewable energy projects etc—to align with the network’s growth, not just BTC price pumps. This shifts you from middleman to network contributor, boosting long-term value and dodging the “glorified ETF” label.
2. Acquire Cash-Flowing Assets—Diversify 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 euphoria—gold 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. That’s the difference between leaderboard bragging and surviving the cycle…
3. Avoid the Pref Trap Unless You’re Saylor-Scale: Issuing preferred stock is suicide for most—worse yields, weaker credit profiles. Why? You won’t beat MSTR’s 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 road—any reverse merger BS with a CEO who’d click a wallet drainer link won’t get a better credit profile or sustain higher-yielding paper than whats on Saylor’s menu. Prefs are a consolidation trap—Saylor’s using them to dominate fixed income; you’ll just cannibalize yourself trying to compete.
4. Survive Volatility— Bitcoin’s 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. Loyalty’s fleeting; conviction comes from understanding edges the market doesn’t see yet, not historical performance.
5. Lock Down Governance—Be Lean or Get Eaten: Shorts feast on bloat—excessive 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 funds—prove you’re not a SPAC 2.0. You’re building for Bitcoin’s network, not Wall Street fees—governance is your moat in the coming bubble burst.

Conclusion: Bitcoin’s the King, Rewriting Finance Forever

Saylor’s shown what’s possible, but strategy is not a template. The Bitcoin treasury meta is Wall Street’s desperate grab at Bitcoin’s rise, fueled by Gensler’s crackdowns that deprived US investors of crypto exposure. But it’s a sideshow to the real revolution: Bitcoin’s forcing a total rewrite of the financial system. Forget EBITDA or free cash flow—companies won’t 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 2–100% of long-term cash reserves for every public company. Metrics like mNAV? Bitcoin per share ? Pure imagination—no 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 noise—for most, owning Bitcoin straight trumps treasuries stocks, especially if you’re not mandate-confined or chasing leverage/income.

This meta, born from Gensler’s chokeholds, is birthing a new order: decentralized scarcity over centralized fiat. Wall Street deregulates, Bitcoin gets “regulated”—they will not meet in the middle but spawn a new beast of how to value stocks. Treasuries bridge the gap, but Bitcoin’s the core—rewriting rules, busting models, forcing finance to bend the knee.

For my friend, I didn’t say take the job or not—I’m just going to send him this….Bitcoin CEO’s will be the major incremental demand driver the next few months, they will determine the cycle…

- Thanks for reading. I’ve been busy….
Parasite