Historical past, they say, doesn’t repeat, however it typically rhymes. Bitcoin-hodling MicroStrategy is a superb instance.
In early 2000, MicroStrategy embodied the excesses of the dotcom bubble: Tremendous Bowl advertisements, a sky-high inventory value of $333, a $25bn market cap, and boundless optimism. Then got here accounting restatements, fines, lawsuits, and a humbling order from the SEC to “cease and desist” from securities legislation breaches. By autumn 2001, with its inventory scraping $0.42, the corporate appeared destined to affix the prolonged roster of tech-bubble casualties.
However company obituaries, like Abe Vigoda’s, may be untimely. The enterprise intelligence software program firm clawed its means again within the ensuing decade-and-a-half, stabilising at round a $1-2bn market cap. Then, in 2020, co-founder Michael Saylor — the identical government who presided over the 2000 debacle — remodeled MicroStrategy into one thing new: a bitcoin-based funding automobile.
Undeterred by sceptics, Saylor has passionately touted bitcoin as “essentially the most precious asset on the planet.” And that’s one among his extra measured pronouncements.
#Bitcoin is a swarm of cyber hornets serving the goddess of knowledge, feeding on the hearth of fact, exponentially rising ever smarter, sooner, and stronger behind a wall of encrypted power.
— Michael Saylor⚡️ (@saylor) September 18, 2020
The critics had a field day when bitcoin crashed in 2022. However who’s laughing now?
Bitcoin’s resurgence has despatched MicroStrategy’s market cap hovering to almost $70bn, with the corporate’s share value up over sixfold previously 12 months and 20 instances (!) within the final 5 years. This 12 months alone it has rallied 438 per cent. Saylor — recent from settling a $40mn tax fraud lawsuit final June with Washington, DC — has emerged as company America’s final Comeback Child, the Joe Montana of the Nasdaq.
MicroStrategy has raised capital aggressively to finance its bitcoin purchases, promoting $4.6bn of equity in recent times and elevating $3.2bn from convertible bonds in 2024 alone. Now it’s doubling down with an audacious $42bn fundraising plan, evenly cut up between an at-the-market (ATM) fairness providing program and new debt securities. At present costs, which means shopping for almost 600,000 Bitcoin — shut to three per cent of the entire provide.
This raises the query: Is that this one other act of hubris, a callback to the Tremendous Bowl splurge of 2000, or one other step in MicroStrategy’s unstoppable rise? Relying in your standpoint, the corporate’s rationale for the $42bn goal is both mystical or meshuggeneh.
As per Bloomberg:
The explanation for that quantity is partly associated to the science fiction collection The Hitchhiker’s Information to the Galaxy the place a supercomputer calculates the reply to the query of life, the universe and every little thing because the quantity 42, in accordance with MicroStrategy Chief Government Officer Phong Le.
“We imagine it’s a singular quantity with some particular traits. It’s the sum of 21 plus 21,” Le stated on an earnings name Wednesday. “Everyone knows that 21 is a magic — a magical quantity on the planet of Bitcoin. There can solely ever be a most of 21 million Bitcoin in circulation.”
The mechanics of the equity-raise benefit a more in-depth look. ATM offerings permit corporations to dribble out new shares progressively into the market somewhat than by means of conventional placements. It’s a chic resolution for risky shares like MicroStrategy’s, enabling corporations to capitalise opportunistically on value spikes whereas avoiding the steep reductions usually required for giant placements.
It’s additionally an “everyone-welcome” mannequin — all traders have an equal likelihood to purchase shares, with no favouritism for establishments — and the minimal intermediation arguably aligns with the decentralisation ethos of crypto. Furthermore, administration doesn’t need to waste time on roadshow trips or rubber-chicken lunches with fund managers.
The ATM’s flexibility has made it widespread with capital-consumptive sectors — resembling real estate investment trusts, life sciences and energy — as a option to meet ongoing funding wants. MicroStrategy’s embrace of the ATM speaks to the device’s versatility.
The essential issue is for the shares to have sufficient on-exchange liquidity to permit an issuer to promote in dimension. Roughly talking, you don’t need your promoting program to account for greater than, say, 10-20 per cent of the quantity in any buying and selling session. MicroStrategy advantages from enormous buying and selling circulate, making it possible to dump loads of inventory by way of ATM with out placing undue stress on the inventory. Additionally, blocks of shares are generally bought when a fund supervisor makes a bid, however these are on the full discretion of administration.
ATMs are predominantly a US phenomenon; European and Asian markets are likely to favour conventional strategies of capital-raising — typically with pre-emptive rights — over opportunistic issuances.
At a sensible stage, few abroad small or mid-cap shares have something just like the liquidity of American ones to make an ATM possible. The Dutch and British governments have used on-market promoting packages to unload shares in banking giants like ABN Amro and NatWest, however solely with pre-existing holdings from monetary crisis-era rescues.
For Microstrategy, the ATM presents a juicy arbitrage play. The corporate’s inventory trades at a roughly 2.8 times premium to the worth of its bitcoin holdings, largely attributable to its leveraged steadiness sheet. So every share bought by means of the ATM primarily represents almost three bitcoins’ value of worth, whereas the proceeds purchase only one bitcoin. Because of this extra inventory will increase the bitcoin per share.

Or as Big Brother would possibly say, “dilution is accretion.”
Two eventualities might disrupt this fandango. First, if bitcoin trades down, the premium to internet asset worth (NAV) would possibly slim or flip to a reduction. Second, the continued issuance of inventory would possibly finally erode the premium, forcing shares right down to the underlying bitcoin worth. However for now, each dangers really feel like a good distance off.
The premium to NAV additionally means MicroStrategy can layer on extra leverage, which in a rising bitcoin market solely widens the premium. To date in 2024 MicroStrategy has issued 4 convertible bonds for a complete of $3.2bn, locking in low- or zero-cost financing, to purchase much more bitcoin. The excessive volatility and market liquidity of MicroStrategy shares imply that it may possibly obtain notably enticing phrases on a convertible.
This technique — borrowing in US {dollars} (which administration expects to be value much less) to purchase bitcoin (which it expects to understand) — is atypical for a carry trade, given bitcoin’s zero yield. However as MicroStrategy has been in a position to problem at zero or sub-1 per cent, its place doesn’t have a lot, if any, damaging working value.
The convertible bond additionally implies that if the inventory value rises, MicroStrategy can redeem the debt with shares buying and selling at a premium. If not, the corporate should both roll over the debt (possible, however provided that markets co-operate), use money circulate from its legacy software program enterprise (tough, given the enterprise lost $18.5mn final quarter), or promote a few of its bitcoin (blasphemously sacrilegious).
The serial issuance of convertible bonds in essence represents a same-way leveraged guess on forex debauchery.
In brief, MicroStrategy’s “21/21 plan” can pay enormous dividends (seriously, not literally, in fact) so long as bitcoin stays excessive and retains climbing. A pointy and extended downturn might upend these assumptions and switch a virtuous cycle right into a vicious spiral.
MicroStrategy’s announcement additionally spotlights a curious contradiction. SEC rules tightly limit administration from hyping their inventory and require danger components round disclosure.
Saylor doesn’t forecast MicroStrategy’s inventory value, however he typically makes daring predictions on bitcoin’s value which, given MicroStrategy’s holdings, immediately impacts the inventory value. Only recently he predicted that bitcoin would hit $13mn per coin by 2045, which might make the corporate’s current stash alone value over $3tn, excluding future purchases.
For the previous 4 years MicroStrategy has stated it’s going all-in on bitcoin. Now, with its 21/21 plan, it’s most likely time to take its statements critically — and actually.