JPMorgan

Coin

MSTR

Wednesday

A video of a frustrated Strategy shareholder pressing co-founder Michael Saylor and CEO Phong Le over a collapsed investment spread across crypto circles again on Tuesday.
The exchange is not new. It happened during a livestreamed shareholder Q&amp;A <a href="https://www.strategy.com/press/strategy-to-host-live-q-a-with-investors-featuring-michael-saylor-and-phong-le_08-11-2026" rel="noopener noreferrer nofollow">on Aug. 17</a>, and it is recirculating now with MSTR still about 74% below its all-time high and Bitcoin more than a third below its own record.
Strategy, formerly known as MicroStrategy, is the largest corporate holder of Bitcoin. Its stock is built to amplify Bitcoin's moves in both directions, a design that sat at the center of the shareholder's question.
Michael Saylor has made his Bitcoin case in TheStreet Roundtable's own archive.&nbsp;Watch the conversation below.
<figure>
 <figcaption>
 24-09-23, Michael Saylor - PULLOUT 5 (6:48)
 </figcaption>
</figure>
<h2 id="the-question">The question</h2>
The session was Strategy's second live retail investor Q&amp;A, moderated by Coin Stories host Natalie Brunell, <a href="https://thenewsblock.substack.com/p/the-questions-everyone-was-asking" rel="noopener noreferrer nofollow">according to her account of the exchange</a>.
A shareholder identified only as Rob said he had invested $73,000 in MSTR for each of his three children. By the time of the session, he said, each position was worth about $20,000.
On the figures he gave, the three positions together had shrunk from $219,000 to about $60,000 by the day of the session, a paper loss of roughly $159,000.
The stock's long-term potential, he said, had become a function of getting back to breakeven, and common shareholders seemed to be the company's lowest priority. He asked whether Strategy would consider paying a dividend to common shareholders.
<figure><img src="https://www.thestreet.com/.image/c_fit%2Ch_675%2Cw_1200/MjI0NDk4NzY2ODA2MjYzNzcy/michael-saylor-chairman-and-chief-executive-officer-at-microstrategy-speaks-during-the-dc-blockchain-summit-in-washington-dc-us-on-tuesday-may-24-2022.jpg" height="675" width="1012">
 <figcaption>
 Michael Saylor, chairman and chief executive officer at MicroStrategy, speaks during the DC Blockchain Summit in Washington, D.C., US, on Tuesday, May 24, 2022. 
 Getty Images
 </figcaption>
</figure>
<h2 id="the-answer">The answer</h2>
Le told him common shareholders are the company's top priority.
That edge comes from what executives call amplified Bitcoin. Amplification cuts both ways. When Bitcoin falls 50%, MSTR tends to fall further.
Le did not offer a dividend. What fixes MSTR, he said, is fixing the credit side of the business, where the company's energy is focused. Saylor added that anyone who wants a dividend should look at the company's preferred stocks.
Saylor said the stock was never designed to behave like a typical equity, and he asked shareholders to expect a long wait. He said he felt Rob's pain, but that investors have to be prepared for difficult years and may need to ride through a year or two before things start working in the equity's favor.
He said anyone holding the equity with a time horizon under four years is probably in the wrong instrument, and put the ideal holding period at seven to 10 years.
<h2 id="where-things-stand-now">Where things stand now</h2>
MSTR closed Wednesday at $142.54, up 5% on the day, <a href="https://finance.yahoo.com/quote/MSTR/history/" rel="noopener noreferrer nofollow">according to Yahoo Finance d</a>&nbsp;The shares have lost more than 40% of their value over the past year and remain about 74% below the all-time high of $543 set on Nov. 21, 2024.
<figure>
 <figcaption>MSTR closed at $97.68 on Aug. 17 and $142.54 on Nov. 4, a 46% gain since the exchange. Source: Yahoo Finance historical prices.
 </figcaption>
</figure>
MSTR closed at $97.68 on Aug. 17, the day of the exchange. It has climbed 46% since then. Whether Rob still holds the shares is not&nbsp;known.&nbsp;
Bitcoin traded near $80,500 on Wednesday evening ET, <a href="https://coinmarketcap.com/currencies/bitcoin/" rel="noopener noreferrer">per CoinMarketCap</a>, about 36% below its October 2025 record above $126,000.
Strategy last week reported the largest quarterly operating income in its history, $20.9 billion for the third quarter, nearly all of it paper gains on its Bitcoin holdings, <a href="https://www.strategy.com/press/strategy-announces-third-quarter-2026-financial-results_10-29-2026" rel="noopener noreferrer nofollow">according to its earnings release</a>. The company held 848,517 BTC as of Oct. 25 at an average cost of $75,446 per coin.
Its favored "BTC Yield" metric, which tracks Bitcoin holdings per share, is down 3.7% this year.
On Monday, Strategy said it bought another 811 BTC for $65.5 million at an average price of $80,846, <a href="https://www.strategy.com/press/strategy-acquires-811-btc-and-repurchases-208-million-of-strc_11-02-2026" rel="noopener noreferrer nofollow">according to a regulatory filing</a>. It spent more than three times that amount, $208.2 million, buying back its STRC preferred shares, the same prioritization Rob pressed management on.
The company now holds 849,328 BTC, more than 4% of the 21 million Bitcoin that will ever exist, and keeps a $4.79 billion dollar reserve.
<h2 id="a-bigger-test-arrives-this-month">A bigger test arrives this month</h2>
The clip's second life comes days before a key date for the stock. Index provider MSCI decided on Oct. 15 to bar "non-operating companies" from its global equity indexes under new financial tests, <a href="https://app2.msci.com/webapp/index_ann/DocGet?lang=en&amp;pub_key=aq0wbkjxPgo%3D" rel="noopener noreferrer nofollow">according to its announcement</a>, a category Strategy could fall into. The question also came up at the August Q&amp;A.
The final list of affected companies is due Nov. 11, with changes taking effect at the close of Nov. 30. JPMorgan has estimated an MSCI exclusion could drive $2.8 billion in outflows, with another $8.8 billion at stake if other index providers follow, <a href="https://www.thestreet.com/crypto/markets/michael-saylor-drops-bold-bitcoin-call-ahead-of-major-index-review" rel="noopener noreferrer nofollow">TheStreet reported last month</a>.
The pressure is not new. Strategy's market premium over the value of its Bitcoin, known as mNAV, has compressed this year, and Saylor <a href="https://www.thestreet.com/crypto/trading/michael-saylor-finally-addresses-short-sellers-as-mnav-drops" rel="noopener noreferrer nofollow">took aim at short sellers</a> in June as the gap narrowed.
Disclaimer: The information provided here is for general informational purposes only and should not be considered financial advice. You should consult with a licensed financial advisor before making any investment or financial decisions.

MicroStrategy shareholder says his $219K investment for three children fell 73%, Saylor responds

Table of Contents

TheStreet Roundtable

Other articles published on Nov 5, 2026

Join our free newsletter for daily crypto updates!