Jun 2026
The Pioneer, Revisited
Strategy, the limits of never sell, and what disciplined automation would have changed.
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Slide 1
ARCH PUBLIC · CASE STUDY The Pioneer, Revisited Strategy, the limits of “never sell,” and what disciplined automation would have changed. June 2026 · For educational purposes only. Source: SaylorTracker.com, as of June 3, 2026.
Slide 2
Source: SaylorTracker.com, as of June 3, 2026. For educational purposes only. WHERE THINGS STAND The treasury, today In January we documented Strategy as the world’s largest and most aggressive corporate Bitcoin treasury. The thesis then was conviction at any price. Six months on, that thesis is being tested in public. HOLDINGS 843,706 BTC across 110 buys AVERAGE COST BASIS $75,701 BTC now $66,052 RESERVE VALUE $55.70B $63.87B deployed UNREALIZED P / L −12.79% −$8.17B underwater Q1 2026: a −$12.54B net loss as Bitcoin fell from ~$87,000 to ~$68,000. MSTR trades at $131.28, 0.84× below its 200-week line while Bitcoin holds 1.07× above its own.
Slide 3
A fiduciary lesson, not a verdict on any individual. For educational purposes only. THE TRIGGERING EVENT 32 coins, one broken promise On June 1, 2026, in an 8-K filing, Strategy disclosed it sold 32 BTC, about $2.5 million, between May 26 and 31. The stated purpose: to help fund distributions on its STRC preferred stock. It was the company’s first Bitcoin sale since a small tax-loss harvest in late 2022. For years, the defining message was simple and absolute: never sell. A 32-coin sale to cover a dividend is a different sentence than the one investors were told to expect. 32 BTC sold 0.0038% of the stack. In dollar terms, trivial. In narrative terms, it is not.
Slide 4
Mark-to-market pain, financing pressure, narrative fracture: each is a risk a disciplined, automated system is built to absorb. Deploying Arch Public’s algorithms is designed to mitigate all three. THE PREDICAMENT The predicament in plain terms Strategy is not collapsing. It still holds one of the largest corporate Bitcoin treasuries on Earth. The issue is structural, and it has three parts. 01 Mark-to-market pain With Bitcoin near $66,000 against a $76,000 basis, large portions of the treasury sit at unrealized losses. The direct consequence of buying heavily into strength. 02 Financing pressure Accumulation was powered by convertible debt and high-yield preferred equity at an 11.5% dividend. When Bitcoin will not cooperate, selling becomes the path of least resistance. 03 Narrative fracture Management now describes “actively managing the balance sheet to maximize Bitcoin per share.” Defensible finance. To many followers, it reads as a retreat.
Slide 5
ROOT CAUSE Why this was predictable This is not bad luck. It is the arithmetic of timingagnostic accumulation. Buying regardless of price means buying the most during euphoria, when positions are largest, and buying with the same indifference into all-time highs. That pulls average cost up toward the peaks and leaves the position exposed to the next drawdown with no buffer. Layer leverage on top, and a modest decline becomes severe equity destruction. Across 2025, Bitcoin finished roughly flat while Strategy shares fell over 50%. Conviction is not a risk management system. Arch Public’s algorithms supply the system conviction lacks: entries that buy weakness, profit-taking that builds cash, and tax efficiency on demand. Strategy’s actual purchases (orange) cluster at the highs. Source: StrategyTracker.com, Jun 3, 2026.
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All scenarios are backtested or illustrative. Past performance does not guarantee future results. THE COUNTERFACTUAL Same dollars, three disciplined paths Same conviction. Same belief in Bitcoin. The same $63.87 billion Saylor deployed. Different execution. SCENARIO 1 Layer 1 only High-conviction, long-only accumulation through the Intelligence Algorithm. Maximum Bitcoin, lowest cost basis. SCENARIO 2 Layer 1 + Layer 2 Pair accumulation with the Market Wave swing strategy. Take profits across cycles to build a usable cash position. SCENARIO 3 Layer 1 + tax harvesting Keep long-only accumulation, then add Arch Public’s Tax-Loss Harvesting algorithm, built to execute in turbulent markets while minimizing slippage.
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THE ENGINE Layer 1: The Intelligence Algorithm A long-dated accumulation engine: the Intelligence Algorithm, set to a 0.5 Intelligence Factor. It concentrates buying in dips and troughs and avoids chasing euphoric highs. Same longterm conviction, disciplined entries. The test: take Saylor’s exact cost basis, $63.87 billion, and deploy it evenly across 18 trades. The engine waited for its first entry in July 2021, sat out the 2023–2024 run to highs, and reengaged on the 2025–2026 pullbacks. 2.66× more BTC, same capital $28,417 avg cost vs $75,701 +134.6% return vs −12.79% Blue arrows: the algorithm’s DCA entries, concentrated in weakness. Source: TradingView backtest.
Slide 8
*Strategy’s IRR cannot be computed without its lot-level purchase history. Value comparisons use the same capital and valuation date. Backtested; past performance does not guarantee future results. SCENARIO 1 Layer 1 only: high-conviction long The purest expression of Saylor’s own thesis, executed with discipline. All $63.87 billion runs through the Intelligence Algorithm, long-only, never sold. Strategy (actual) Scenario 1 (Layer 1) Capital deployed $63.87B $63.87B BTC held 843,706 2,247,581 Average cost $75,701 $28,417 Position value $55.70B $149.8B Total return −12.79% +134.6% Money-weighted IRR n / a* +30.6% Useable cash None (had to sell) None (fully invested) THE STRENGTH The most Bitcoin and the highest end value of any scenario. THE TRADE-OFF Like Saylor, it is fully invested. It builds wealth but generates no cash, so funding an obligation still means selling.
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Gives up ~8 points of return and ~188,000 coins versus all-in long, in exchange for $7.56B cash, a higher IRR, and never selling the core. Past performance does not guarantee future results. SCENARIO 2 Layer 1 + Layer 2: the 80 / 20 split Deploy 80% ($51.10B) to Layer 1 accumulation and 20% ($12.77B) to the Market Wave algorithm, run as a swing strategy that buys troughs and sells peaks across cycles. Market Wave takes profits along the way. Those realized gains become a usable cash position, the exact thing Saylor did not have on June 1 when he sold Bitcoin to fund a dividend. USABLE CASH GENERATED $7.56B BLENDED IRR ~32.2% BTC HELD 2,060,095 TOTAL VALUE $144.7B Market Wave buys troughs (blue) and sells peaks (magenta). The 20% slice returned +94.2%. Source: TradingView backtest.
Slide 10
Illustrative only and not tax advice. Crypto wash-sale treatment reflects current law, which could change. Consult a qualified tax professional. SCENARIO 3 Arch Public’s Tax-Loss Harvesting Algorithm Keep Scenario 1’s long-only accumulation, then add Arch Public’s Tax-Loss Harvesting algorithm, built to execute cleanly in turbulent markets while minimizing slippage and prioritizing liquidity. Because Bitcoin is treated as property, losses can be harvested and the position promptly re-established. The worked example harvests at $65,000 per coin during January and February 2026. Lot purchased Cost basis BTC washed Realized loss Feb 23, 2025 $96,266 36,859 −$1.15B Apr 27, 2025 $93,781 37,836 −$1.09B Jan 4, 2026 $91,494 38,782 −$1.03B Total — 113,477 −$3.27B $686M tax shield at the 21% corporate rate Position unchanged: all 113,477 coins are immediately repurchased at $65,000, banking the loss while keeping every coin. This is the lever Strategy lacked on June 1: tax efficiency instead of a forced sale. Applied to Saylor’s larger, higher-basis stack the shield would be greater still, and the same algorithm serves high-net-worth investors carrying sizable Bitcoin positions.
Slide 11
Same belief in Bitcoin, same capital. Every disciplined path keeps the promise. *IRR for Strategy is not computable from public data; value comparisons use the same capital and valuation date. SIDE BY SIDE The actual path vs three disciplined alternatives Dimension Strategy (actual) S1: Layer 1 S2: 80 / 20 S3: + Tax harvest Capital $63.87B $63.87B $63.87B $63.87B BTC held 843,706 2,247,581 2,060,095 2,247,581 Position value $55.70B $149.8B $144.7B $149.8B Total return −12.79% +134.6% +126.5% +134.6% IRR n / a* +30.6% +32.2% +30.6% Cash / tax benefit None None $7.56B cash $686M shield Dividend funding Sold BTC (Jun 1) Requires a sale Profit-taking cash Harvested benefit “Never sell” promise Broken for STRC Intact Intact Intact
Slide 12
Educational purposes only. Cryptocurrency trading involves significant risk. Past performance does not guarantee future results. Not tax, legal, or investment advice. A PATH FORWARD “Never sell” is a promise, not a plan. What Strategy built is undeniable: it proved Bitcoin can sit on a corporate balance sheet at scale, and inspired a global movement. When the only tools are conviction and leverage, a down cycle eventually forces a choice between obligations and identity. A disciplined, automated system removes that choice. Lower average costs. Actively managed drawdowns. Cash generated from volatility instead of from the stack. Tax efficiency that frees capital exactly when it is needed most.
Backtested results, for educational purposes only. Not a recommendation to buy or sell any security or digital asset.