How the Strategy Empire Breaks, and Whether Saylor Can Stop It

Vinny Lingham warned 18 months ago that Michael Saylor would harm Bitcoin more than FTX. Now he maps how the Strategy empire breaks and the one move that could slow the bleed. ======================================================== Thank you to our sponsor! ⁠⁠⁠⁠⁠Fidelity⁠⁠⁠⁠⁠: Fidelity has been building in crypto and DeFi since 2014 — now they're hiring. Explore career opportunities at one of the most forward-thinking names in finance here: ⁠⁠⁠⁠⁠crypto.fidelitycareers.com⁠⁠⁠⁠⁠. ⁠⁠⁠⁠⁠Cape⁠⁠⁠⁠⁠: Your biggest crypto vulnerability isn't your wallet, it's your phone number. Cape is America's privacy-first mobile carrier that rotates your SIM identity daily and blocks SIM swaps before they happen. Get 33% off your first six months at cape.co/unchained (use code: UNCHAINED). ======================================================== Strategy's stock has fallen over 80% from its November 2024 high, its STRC preferred trades well below par, and a fresh $335 million raise has done nothing to restore confidence. Vinny Lingham, co-founder of Praxos Capital, tweeted in October 2024 that Michael Saylor would do more damage to Bitcoin than FTX. On Unchained, he argues the collapse was always predictable, and that this is not a Ponzi but what he calls a 'Saylor scheme.' Lingham maps how the empire breaks once MSTR trades at a discount to mNAV, why the 32-Bitcoin sale and the $1.5 billion buyback of 2029 converts blew Saylor's runway, and why $6.7 billion in convertible notes raises default risk by 2028. He also weighs a Soros-style attack theory and the switch to bimonthly dividends. His fix is the one thing Saylor won't do: stop buying, stop diluting, wait it out. The question is who removes the biggest buyer of Bitcoin, him or the market. Host: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Laura Shin⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, Host / Unchained Guests: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Vinny Lingham - Co-founder of Praxos Capital Timestamps 📉 01:11 Strategy in free fall: why Vinny says the collapse was always coming 🪤 06:24 Why buying back 2029 debt blew Saylor's runway ₿ 07:36 The '32 years of dividends' claim and what a deeper bear market does to it 🏚️ 10:23 How the MSTR empire actually breaks: the discount-to-mNAV trap 🎯 13:35 Why is Strategy faltering? Is it leverage or a Soros-style attack on MSTR? 💙 16:38 Cape: Get 33% off your first six months with code unchained at https://cape.co/unchained 💚 17:32 Fidelity: Explore crypto careers that could change your future at https://crypto.fidelitycareers.com 📆 18:15 Why switching to bimonthly dividends makes the problem worse ⏳ 19:29 The $6.7B convertible-note overhang and the 2028 default risk 🛟 22:07 Can MSTR be saved, and the most likely outcome from here Learn more about your ad choices. Visit megaphone.fm/adchoices