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Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.
Andy Edstrom returns to dissect the spectacular collapse of Bitcoin treasury companies and explore why these supposedly "Bitcoin-backed" investments have become what he calls an "unmitigated disaster." (01:43) The conversation spans from MicroStrategy's unique position to failed DATs (Digital Asset Treasury companies), valuation frameworks like MNAV, and broader market dynamics. Edstrom and host Preston Pysh examine the risks of securitizing Bitcoin, compare these companies to stablecoin issuers like Tether, and debate whether Bitcoin's four-year cycles are evolving or breaking down. They also explore investment opportunities beyond Bitcoin, from AI and energy plays to commodities, while wrestling with the reality that we may be entering a "get rich slower" era for Bitcoin rather than the explosive growth of previous cycles.
Host of The Investor's Podcast Network's Bitcoin Fundamentals podcast, celebrating ten years of financial education content. Preston has been covering Bitcoin and macro investing for years, bringing sophisticated financial analysis to retail investors seeking mastery in alternative investments and emerging technologies.
Author of "Why Buy Bitcoin: Investing Today in the Money of Tomorrow" published in 2019. Edstrom is a former wealth manager with an economics degree and extensive experience in traditional finance, who has become a thoughtful Bitcoin analyst known for his contrarian takes and risk-adjusted investment frameworks.
Most Bitcoin treasury companies outside of MicroStrategy have become "dumpster fires," with many down 80-95% from their peaks. (01:43) These companies often lack cash flow from underlying businesses, have inexperienced leadership running public companies, and fail basic operational requirements like timely SEC filings. The core issue is execution risk combined with leverage - when Bitcoin volatility meets operational incompetence, shareholders get decimated. Unlike MicroStrategy's disciplined approach with actual business cash flows, most treasury companies are essentially gambling with debt financing on volatile assets.
MicroStrategy can be understood as creating dollar-denominated stablecoins backed by Bitcoin rather than US Treasuries like Tether. (07:07) This requires 5:1 over-collateralization due to Bitcoin's volatility - if Bitcoin can drop 70-80%, you need five times backing to maintain the peg. The preferred stock acts like dividend-paying stablecoins at roughly 10% yield. This framework helps explain why the strategy works when executed properly with adequate collateralization ratios, unlike competitors using more volatile assets or insufficient backing.
Net Asset Value multiples (MNAV) for Bitcoin treasury companies should typically trade between 0.8x to 2.5x, not the 15x+ ratios some promoted during peak euphoria. (15:15) Historical analysis of closed-end funds shows 20% discounts (0.8x MNAV) often signal attractive buying opportunities, while premiums above 2.5x are rare and unsustainable. Well-managed holding companies like Berkshire trade around 2x book value even with significant operational advantages, providing a reasonable benchmark for exceptional Bitcoin treasury operators.
Education burden remains massive - understanding Bitcoin requires knowledge spanning game theory, network topology, monetary history, and geopolitics. (29:40) Most people lack time or motivation for this learning curve. Additionally, half the population lives paycheck to paycheck and cannot invest in volatile savings technologies, while affluent investors are distracted by seemingly "sexier" opportunities like AI that provide immediate, tangible demonstrations of value through simple interactions.
Despite diminishing halvings impact, Bitcoin's four-year cycles likely continue because large early holders (OGs) can single-handedly create market tops through coordinated selling. (54:06) One individual selling 80,000 coins marked the exact market peak this cycle. Until coin distribution broadens significantly and these massive holders reduce their positions over time, individual whales retain the power to create self-fulfilling cyclical patterns regardless of fundamental halving mechanics.