MicroStrategy underperforms its dot-com bubble peak

At the peak of the Dot Com bubble in the year 2000, Michael Saylor’s MicroStrategy (now just called ‘Strategy’) looked unstoppable. The stock had gone from a small software IPO to one of the wildest names in tech.

Strategy went public on June 11, 1998, and the IPO price was about $6 per share after later splits. During the late 1990s tech frenzy, money poured into internet and software stocks, so the MSTR stock went on a monster rally akin to the one we’ve seen in 2024-2025.

By early March 2000, Saylor’s stock had reached around $3,130. How crazy is that? For context, Strategy is worth $134 as of press time.

MSTR’s Dot Com crash began on March 20th, 2000.

You see, Saylor and his team had just announced that they would restate financial results due to accounting problems. That day, the MSTR stock fell about 62% in a single day. Prices dropped from the thousands into the $120 to $140 range during that panic selloff.

The crash did not stop there. As the wider tech crash spread through 2000 and into the early 2000s, the stock kept falling. By 2002, shares traded near $0.40 to $0.50. A former high flying tech stock had become a penny level name. The Dot Com era ended with massive losses locked in for long term holders. And Saylor gained a terrible reputation on Wall Street and Silicon Valley alike.

Bitcoin bet deepens Strategy’s modern crash

As you likely know, in August 2020, MicroStrategy changed direction. The company invested $250 million in bitcoin as a treasury reserve asset, with management pointing to weak cash returns, a softer dollar, and global macro pressure.

Of course more bitcoin purchases followed. In a short period of time, the company became the largest corporate holder of bitcoin. And Saylor gained the nickname ‘Bitcoin King,’ dressing up as Bitcoin for 2 Halloweens in a row, and even hosting extravagant Bitcoin-themed parties. He is obsessed in ways that are probably unhealthy.

Anyway, as bitcoin pulled back, the stock sank with it. Over the past 52 weeks, MicroStrategy shares dropped 67.03%, and it is down exactly 26.94% year to date. In July 2025, shares hit a 52 week high of $457.22. Since then, they have fallen 71.8%.

The company added more risk in 2025. It launched four credit instruments during the second and third quarters. The total value reached $4 billion. Saylor told Bloomberg in a live interview that the securities were high yield perpetual instruments designed to lower bitcoin risk for investors. The market response stayed negative.

By late November 2025, Forbes reported the shares were down 60% from the prior year. Market value fell to $49 billion. That was below the $56 billion worth of bitcoin on the balance sheet. Around the same time, CEO Phong Le said the company might sell bitcoin. Soon after, bitcoin fell below $86,000 in early December.

Analysts meanwhile have adjusted expectations. Canaccord Genuity analyst Joseph Vafi (MSTR’s biggest bull by the way) cut his price target from $474 to $185 but kept a Buy rating. He said bitcoin no longer behaves like digital gold and is facing an identity crisis.

Mizuho analysts also reduced their target from $484 to $403 while keeping an Outperform rating. They pointed to fintech pressure and a growing divide between bitcoin and dollar backed stablecoins.

Even now, MicroStrategy remains heavily watched. Sixteen analysts cover the stock. Thirteen rate it Strong Buy. One rates it Moderate Buy. Two rate it Hold. The consensus target is $464.36, implying 324% upside. The highest target sits at $705, suggesting 544% upside.