Saylor’s 800K Bitcoin Problem
June 25, 2026
Onramp hosts make the case that the strain showing up in Michael Saylor's STRC preferred stock, now trading near $80 at roughly 20% below par, reflects leverage and structure rather than any weakness in bitcoin. With an estimated 80% of MSTR holders and around 99% of other treasury-company holders underwater, Onramp reads the sell-off as a counter-signal to accumulate, noting that a five-year dollar-cost average into bitcoin has roughly matched the S&P 500.
The Last Trade: a weekly, bitcoin-native podcast covering the intersection of bitcoin, tech, & finance on a macro scale. Hosted by Jackson Mikalic, Michael Tanguma, & Brian Cubellis. Join us as we dive into what bitcoin means for how individuals & institutions save, invest, & propagate their purchasing power through time. It's not just another asset… in the digital age, it's The Last Trade that investors will ever need to make.
🎙️ About This Episode
The guys open on Philippe Laffont of Coatue admitting he no longer knows what to think about Bitcoin, and use it to frame why so many TradFi allocators get shaken out: they treat Bitcoin as just another speculative bet rather than a better money whose debasement thesis is unchanged and strengthening. They lay out the deep value case with a five-year DCA into Bitcoin roughly matching the S&P 500 even with Bitcoin 50% below its highs, Frank A. Fetter's 200-week moving average signal, and Macroscope's gold analog (down about 50% from 1974 to 1976, then up 750% from 1976 to 1980). On macro, they read Kevin Warsh's first FOMC (no dot plot, walking back forward guidance) and the Bloomberg "debasement trade is unraveling" piece as posturing and a counter-signal to accumulate. The bulk of the signal-versus-noise segment is the Strategy / stretch confidence crisis, with STRC trading near $80 (down about 20% from par), Saylor raising cash over the weekend that failed to hold the peg, shifting MNAV and Sharpe ratio math, and an estimated 80% of MSTR holders and roughly 99% of other DAT holders underwater. They close on the hyperscaler free cash flow cliff across Amazon, Microsoft, Google, Meta, and Oracle, Trump's executive order targeting a 2028 quantum computer, and Meta building a points-based prediction market to rival Polymarket and Kalshi, and the data and financial nihilism that powers it.
🧠 Chapters
00:00 - Introduction and Technical Difficulties 02:24 - Current Sentiment on Bitcoin 13:28 - Understanding Market Dynamics and Investor Sentiment 21:30 - The Role of the Federal Reserve and Economic Policy 28:43 - Signal vs. Noise: Analyzing Current Market Events 42:52 - The Role of Microchips in AI and Economic Strategy 46:42 - Corporate Debt and Bitcoin: A Financial Conundrum 49:40 - Historical Analogies: Bitcoin and Gold's Volatility 52:43 - Hyperscalers and the Future of Free Cash Flow 58:50 - The Interplay of Government and Corporate Economies 1:01:21 - Quantum Computing and Its Implications for Bitcoin 1:04:52 - Prediction Markets: The Future of Speculation and Data
Frequently Asked Questions
Why is Michael Saylor facing an "800K bitcoin problem"?
Saylor's leveraged treasury structure is under pressure as STRC trades near $80, about 20% below par, and a weekend cash raise failed to hold the peg. With an estimated 80% of MSTR holders and roughly 99% of other treasury-company holders underwater, the strain sits in the financing structure rather than in bitcoin.
Has bitcoin actually been a good investment despite the drawdown?
A five-year dollar-cost average into bitcoin has roughly matched the S&P 500 even with bitcoin trading about 50% below its highs. The 200-week moving average continues to hold as a historical accumulation signal.
What is the gold analog the hosts use for bitcoin's volatility?
Macroscope's gold analog shows gold falling about 50% from 1974 to 1976 before rising roughly 750% from 1976 to 1980. The hosts use it to argue that deep drawdowns in a sound-money asset can precede the largest moves.
This episode is editorial and educational content. Onramp does not provide tax, legal, or investment advice. Bitcoin is volatile and may lose value. Past performance does not guarantee future results.