A Father Told Michael Saylor His $219,000 MicroStrategy Investment For His Three Kids Had Fallen To $60,000. Saylor Said Shareholders Should Be Ready To “Ride Through” A Year Or Two Of Pain. MSTR Is Up 35.67% In The Past Month.
A father told Michael Saylor that money he invested for his three children had collapsed, and Saylor's answer asked shareholders for a kind of patience that college savings simply cannot afford.
This post may contain links from our sponsors and affiliates, and Flywheel Publishing may receive compensation for actions taken through them.
Michael Saylor, co-founder and executive chairman of Strategy Inc. (NASDAQ:MSTR | MSTR Price Prediction), spoke to shareholders on a livestreamed Q&A on August 17, 2026, and asked them to expect a long wait. “I feel your pain, but I think we have to be prepared to have difficult years… We might have to actually ride through some number of months or a year or 2 in order to get to the point where things start to work to the benefit of the equity,” Saylor said.
Michael Saylor also said the stock “was never designed to behave like a typical equity” and recommended a four-year holding horizon, ideally seven to ten years.
A Father’s Position for Three Children
One of the questions that drew the most attention came from a shareholder. Reports identify him only by his first name, Rob. He said he had invested $73,000 for each of his three children, or $219,000 in total. As of the August 17, 2026 Q&A, he said that combined position had fallen to $60,000. A widely shared post on X summing up the exchange described the decline as over 70%.
Rob said “The term potential is now a function of getting back to breakeven.” Rob added: “MSTR common shareholders seem to be your lowest priority.”
Chief Executive Officer Phong Le answered him directly: “Strategy’s common shareholders remain the company’s top priority.” Saylor’s ride-through comments were aimed at all shareholders during the session. He was addressing the full audience.
Where the Stock Trades Now
As of 9:40 AM ET on October 2, 2026, Strategy Inc. traded at $169.42, up 5.56% in the current session. The stock is up 4.83% over the past week, up 35.67% over the past month, and up 11.50% year to date. Over the past year it is down 49.94%.
Bitcoin (CRYPTO:BTC) is the asset behind those moves. It is up 9.6% over the past month, down 3.16% year to date, and down 29.75% over one year.
Saylor told holders to prepare for a year or two of pain. In the weeks since, the stock posted a large gain over a one-month window and still sits far below where it was a year ago. One month is a short stretch next to the horizon he described, so the rally tells us little about whether his advice was right or wrong.
What Sits Behind the Swings
Strategy Inc.’s second-quarter 2026 filing showed a loss of $24.45 per diluted share. The main driver was an $8.32 billion unrealized loss on digital assets. At quarter end the company held 846,000 bitcoin, carried at $49.7B against a $63.9B cost basis. It cut convertible debt by 18% to $6.7 billion. Its USD Reserve has since grown to $3.75B, which the company says covers 2.1+ years of obligations. Preferred dividends came to $400.7M in the second quarter alone, and the STRC preferred rate went up to 12.00%. The board has approved a $1.0B common stock buyback program, but the company has not bought back any shares under it yet. Updates are posted on Strategy’s investor relations page.
Can College Money Wait Seven to Ten Years?
Saylor’s advice fits the thesis he has pushed for years, and it makes sense for money with no deadline. It is much harder to follow for money set aside for children, because that money will be needed by a certain date. Telling holders after a sharp drop that they should plan on seven to ten years asks them for more patience than most people expect from a listed stock. Many retail buyers likely never planned for that when they first bought.
If that gap between a stock’s time horizon and a child’s tuition date sounds familiar, it is the same mismatch we unpack in a free guide on speculating with no more than a small piece of a portfolio: here.
Anyone considering a similar position should first match the money’s purpose to that horizon. After that, keep an eye on:
- the price of bitcoin
- how long the USD Reserve can cover obligations
- the cost of preferred dividends
- whether the company actually uses the common buyback authorization
Contact [email protected] for any questions or corrections.
AJ spent 10 years writing about financial markets at The Motley Fool. His coverage centers on technology stocks and the broader macroeconomic trends, from interest rates to geopolitics, that shape where markets are headed next. AJ is drawn to the stories where big-picture economics and individual companies collide.
