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MicroStrategy’s Big Buy Raises New Questions

10 min episode · 2 min read

Episode

10 min

Read time

2 min

Topics

Investing, Fundraising & VC, Sales & Revenue

AI-Generated Summary

Key Takeaways

  • MicroStrategy Valuation Risk: Company now buys Bitcoin at 1.1x net asset value despite Saylor's previous 2.5x minimum threshold, risking share dilution below 1.0x that could force Bitcoin sales and buybacks.
  • High-Cost Funding Structure: MicroStrategy sells Stride preferred stock with 10% perpetual dividends and no catch-up guarantees, creating ongoing payment obligations that increase pressure to eventually liquidate Bitcoin holdings.
  • Crypto Banking Charter Progress: OCC head confirms 14 new bank applications including crypto firms, stating digital asset custody deserves same treatment as traditional electronic safekeeping without special regulatory hurdles or discrimination.

What It Covers

MicroStrategy purchases $962 million in Bitcoin through stock sales while trading near book value, raising concerns about sustainability of their leveraged treasury strategy and perpetual dividend obligations.

Key Questions Answered

  • MicroStrategy Valuation Risk: Company now buys Bitcoin at 1.1x net asset value despite Saylor's previous 2.5x minimum threshold, risking share dilution below 1.0x that could force Bitcoin sales and buybacks.
  • High-Cost Funding Structure: MicroStrategy sells Stride preferred stock with 10% perpetual dividends and no catch-up guarantees, creating ongoing payment obligations that increase pressure to eventually liquidate Bitcoin holdings.
  • Crypto Banking Charter Progress: OCC head confirms 14 new bank applications including crypto firms, stating digital asset custody deserves same treatment as traditional electronic safekeeping without special regulatory hurdles or discrimination.

Notable Moment

Saylor proposes nation-states create Bitcoin reserves with 80% BTC, 20% fiat, issuing 10% yield credit instruments through regulated banks, essentially replicating MicroStrategy's capital structure at sovereign level.

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Episode Transcript

Welcome back to The Breakdown with me, NLW. It's a daily podcast on macro, Bitcoin, and the big picture power shifts remaking our world. What's going on, guys? It is Tuesday, December 9. And today, we are talking about a micro strategy buy, some banking controversy, all the normal things in crypto. Before we get into that, however, if you are enjoying the breakdown, please go subscribe to it, give it a rating, give it a review, or if you wanna dive deeper into the conversation, come join us on the Breakers Discord. You can find a link in the show notes or go to bit.ly/breakdownpod. Alright, friends. Well, let's follow-up today with some coverage on the lack of progress for the market structure bill from Monday's show. Senator Bernie Moreno has said that the negotiations have become, in his words, decently frustrating. Moreno appeared at the Blockchain Association event on Monday to give a status report on the bill. Democrats and Republicans are set to meet again today, but Moreno doesn't seem hopeful. He said, we'll see where their heads are at, but it's been decently frustrating in the last couple weeks. His comments align with views recently expressed in the industry stating, what I don't wanna do is promulgate a bad bill just to say that we passed something. No deal is better than a bad deal. From the Democrat side of the house, Eleanor Tarrant, the host of Crypto in America, spoke with senator Mark Warren on Monday. Warner told her it would be, quote, very hard to get market structure to a mark appearing by the end of the year. He blamed the White House, stating that Congress is waiting on acceptable language around ethics and quorum. He quipped, at some point, our Republican colleagues are going to have to decide if this is a White House bill or a congressional call. Still, Warner commented that staff and lawmakers are meeting every day for hours and that a bill will get done. They just need to, in his words, get it right. Pretty clear that this is not happening this year. Now they're officially saying it. Don't hold your breath is my take. Moving back to one of the most perpetual stories of Bitcoin in the last few years, after several months of undersized Bitcoin buying, MicroStrategy is returning to the market in size. MicroStrategy's Bitcoin buying slowed down in recent months as the stock price tanked and funding became scarce. Last week, MicroStrategy announced that they had instead raised money to fund a $1,400,000,000 cash reserve that would ensure they could meet their dividend and debt obligations for the next two years. At the same time, they reduced their targets for the end of this year, now aiming to produce between 2226% Bitcoin yield. The stock has recovered slightly, but more importantly, the market believed the cash reserve or guaranteed dividend payments were made on preferred stock. The stretch perpetual shares are now trading at …

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