Michael Saylor's Bitcoin empire just watched $8 billion in paper gains vanish overnight.

Strategy (the company formerly known as MicroStrategy) is sitting on a 499,226 BTC mountain that's suddenly looking more like a hill, 

The OG corporate Bitcoin whale is underwater on his recent purchases, with some buys made above $97K now worth only $83K.

The DCA Dilemma

Saylor's been buying Bitcoin like it's going out of style since 2020 – through bull markets, bear markets, and everything in between.

His dollar-cost averaging strategy worked beautifully on the way up, making him look like a time-traveling genius with a Bloomberg terminal.

But those most recent buys are getting absolutely rekt right now, raising questions about the long-term viability of the approach. 

To say that Strategy is invested in Bitcoin is the understatement of the century – it's essentially become a leveraged Bitcoin ETF with a CEO who makes Bitcoin maximalists look bearish.

Huge Is One Word For It

Saylor's company now holds $41.6 billion in Bitcoin at current prices, making them the biggest non-government holder by a wide margin. 

Some of their purchases were made at prices that make today's $83K look like the discount bin at a liquidation sale.

The question now is whether Saylor keeps buying the dip or finally pumps the brakes on his perpetual accumulation machine.

His Twitter feed remains unshaken – still posting the same bullish content like his portfolio isn't bleeding billions in unrealized gains.

More Is More

Strategy's stock price is basically Bitcoin on leverage – when BTC sneezes, MSTR catches pneumonia.

The company's valuation is getting hammered hard as the broader market sells off, and that could potentially spell trouble for Saylor’s accumulation strategy. 

Bitcoin's struggle to break resistance levels is weighing on Saylor's empire like an anchor tied to a swimming maximalist.

The market is essentially testing whether Saylor's diamond hands are actually made of diamond or just pressurized hopium.

Continuing To Fight The Good Fight

The entire crypto market is watching Saylor like a hawk – if he blinks, it could trigger a cascade of selling.

Nobody has more riding on Bitcoin's success than the man who transformed an entire software company into a BTC holding vehicle.

His conviction hasn't wavered through multiple 50%+ crashes before, but the stakes have never been this high.

At this point, Saylor has gone so far down the Bitcoin rabbit hole that there's practically no turning back.

The Bull Case Remains

Despite the recent downturn, Strategy's early buys are still massively in profit – some purchased as low as $11K.

Saylor's overall strategy remains in the green, even with Bitcoin's recent descent from its all-time highs.

The average purchase price across all of Strategy's holdings is still well below current market values.

The question isn't whether Saylor's in profit – it's whether that profit will continue to shrink if Bitcoin's downward momentum continues.

The Crystal Ball

Saylor has repeatedly said he's never selling – not at $100K, not at $1 million, not ever.

His time horizon makes HODLers look like day traders – he's planning in decades while the market panics about weekly candles.

Whether he's a madman or a visionary probably depends on what Bitcoin's price does over the next year – but out friend Peter Schiff is likely writing the most insufferable "I told you so" tweets of his entire career.