{"id":42760,"date":"2026-05-19T15:06:18","date_gmt":"2026-05-19T13:06:18","guid":{"rendered":"https:\/\/www.coinpro.ch\/uncategorized\/michael-saylor-under-pressure-is-strategy-getting-more-cautious-with-bitcoin\/"},"modified":"2026-05-19T15:07:21","modified_gmt":"2026-05-19T13:07:21","slug":"michael-saylor-under-pressure-is-strategy-getting-more-cautious-with-bitcoin","status":"publish","type":"post","link":"https:\/\/www.coinpro.ch\/en\/news-en\/michael-saylor-under-pressure-is-strategy-getting-more-cautious-with-bitcoin\/","title":{"rendered":"Michael Saylor under pressure: Is Strategy getting more cautious with Bitcoin?"},"content":{"rendered":"<p data-start=\"392\" data-end=\"697\">For years, Michael Saylor has been seen as one of the loudest Bitcoin bulls in the corporate world. His company Strategy, formerly MicroStrategy, has evolved from a software company into one of the best-known <a href=\"https:\/\/www.coinpro.ch\/en\/knowledge\/the-bitcoin-treasury-101-why-cash-is-no-longer-king-everything-you-need-to-know\/\">Bitcoin treasury companies<\/a>. But right now, the tone around the aggressive BTC strategy is changing.<\/p>\n<p data-start=\"699\" data-end=\"1268\">After a buying spree of around $2 billion, Strategy has reportedly paused its Bitcoin purchases for the time being, according to Investor\u2019s Business Daily. The reason apparently isn\u2019t that Saylor suddenly no longer believes in Bitcoin. Rather, the financing model behind the purchases is becoming increasingly complex. In particular, the role of STRC preferred shares, high ongoing financing costs, and potential dividend obligations are coming into focus.<\/p>\n<p data-start=\"1270\" data-end=\"1543\">For investors, this matters because Strategy is now far more than just a single company with Bitcoin on its balance sheet. The company has become a symbol of institutional Bitcoin optimism. If something changes there, the entire crypto market pays close attention.<\/p>\n<h2 data-section-id=\"b9cp1s\" data-start=\"1545\" data-end=\"1589\">Strategy isn\u2019t just buying blindly<\/h2>\n<p data-start=\"1591\" data-end=\"2135\">The key message isn\u2019t that Strategy has given up on Bitcoin. That would be wrong. The company still holds massive BTC reserves and remains clearly focused on Bitcoin. According to Investopedia, after the latest buying program Strategy held a total of 843,738 Bitcoin. That holding is worth almost $65 billion, depending on the current Bitcoin price.<\/p>\n<p data-start=\"2137\" data-end=\"2400\">Still, the current pause is notable. Because in recent years, Strategy was known for continuing to buy Bitcoin even in difficult market phases. That exact behavior made the company the ultimate Bitcoin bet for many investors.<\/p>\n<p data-start=\"2402\" data-end=\"2618\">Now, however, it\u2019s becoming clear: even Saylor\u2019s model has limits. Strategy isn\u2019t just buying at any price\u2014it has to factor in capital markets, its own share programs, and the cost of financing.<\/p>\n<script type=\"text\/plain\" data-tcf=\"waiting-for-consent\" data-id=\"20572\" data-bid=\"1\" data-placement=\"33872\">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<\/script><h2 data-section-id=\"149sffp\" data-start=\"2620\" data-end=\"2667\">Why the STRC preferred shares are so important<\/h2>\n<p data-start=\"2669\" data-end=\"2988\">A key part of the current debate revolves around the STRC preferred shares. Strategy uses such financial instruments to raise new capital and finance further Bitcoin purchases. The model works particularly well as long as investors are willing to buy these securities on attractive terms.<\/p>\n<p data-start=\"2990\" data-end=\"3555\">According to Investor\u2019s Business Daily, the buying pause became relevant after #STRC fell below par value. That makes it harder for Strategy to issue new preferred shares on favorable terms and raise fresh capital for Bitcoin purchases. At the same time, Strategy\u2019s annual financing costs were put at around $1.7 billion. These costs are mainly driven by the outstanding preferred shares.<\/p>\n<p data-start=\"3557\" data-end=\"3817\">That changes the story around Strategy. In the past, the narrative sounded simple: Saylor buys Bitcoin because he believes in Bitcoin long term. Today, the more precise question is: on what terms can Strategy continue raising capital to buy Bitcoin?<\/p>\n<h2 data-section-id=\"15m7qna\" data-start=\"3819\" data-end=\"3869\">The potential Bitcoin selling question becomes explosive<\/h2>\n<p data-start=\"3871\" data-end=\"4115\">Another point is particularly sensitive: under certain circumstances, Strategy could sell Bitcoin. That\u2019s so explosive because for years Saylor was seen as representing a very clear stance. Buy Bitcoin, hold it, and don\u2019t sell.<\/p>\n<p data-start=\"4117\" data-end=\"4908\">CoinDesk reported back in early May that Strategy had signaled it could sell Bitcoin under certain conditions to meet dividend obligations. Other outlets also frame the latest statements as a possible shift: instead of an absolute \u201cnever sell,\u201d a model is now emerging in which Strategy wants to keep accumulating Bitcoin net over the long term, but no longer fully rules out occasional sales.<\/p>\n<p data-start=\"4910\" data-end=\"5195\">That doesn\u2019t mean Strategy is about to sell large amounts of Bitcoin immediately. But the mere possibility matters for market psychology. Because if the best-known corporate Bitcoin buyer no longer categorically rules out sales, that lands differently than earlier messaging.<\/p>\n<h2 data-section-id=\"z1di6x\" data-start=\"5197\" data-end=\"5246\">Small buys already show a slowdown<\/h2>\n<p data-start=\"5248\" data-end=\"5752\">The current buying pause doesn\u2019t come as a complete surprise. Even earlier, there were signs that Strategy was accumulating more slowly at times. Reports from last week show that Strategy bought only 535 Bitcoin for around $43 million. According to the report, that was the company\u2019s smallest weekly Bitcoin purchase in 2026. After that, the holding stood at 818,869 BTC.<\/p>\n<p data-start=\"5754\" data-end=\"5986\">This point matters because it shows the current development isn\u2019t just a snapshot. For some time now, there have been indications that Strategy is aligning its purchases more closely with conditions in the capital markets.<\/p>\n<p data-start=\"5988\" data-end=\"6177\">Strategy remains bullish on Bitcoin, but the approach looks less mechanical than before. The market needs to look more closely at when and how new purchases are financed.<\/p>\n<h2 data-section-id=\"1uhc3ta\" data-start=\"6179\" data-end=\"6216\">Why this matters for Bitcoin<\/h2>\n<p data-start=\"6218\" data-end=\"6407\">Strategy isn\u2019t just any market participant. The company is one of the largest known Bitcoin holders worldwide. That means any change in its buying strategy sends a signal.<\/p>\n<p data-start=\"6409\" data-end=\"6667\">When Strategy buys, many investors interpret it as a vote of confidence. When Strategy pauses, investors wonder whether a key buyer is temporarily stepping away from the market. And when potential sales are discussed, it creates additional uncertainty.<\/p>\n<p data-start=\"6669\" data-end=\"6921\">At the same time, this development shouldn\u2019t be overstated. Bitcoin today doesn\u2019t depend on Strategy alone. The market is now also heavily influenced by spot Bitcoin ETFs, macro data, institutional capital flows, and global risk sentiment.<\/p>\n<p data-start=\"6923\" data-end=\"7148\">Still, Strategy remains an important psychological factor. Especially for retail investors, Saylor is a symbolic figure. For years, his strategy has shaped the narrative that companies can hold Bitcoin as a reserve asset.<\/p>\n<h2 data-section-id=\"1cmptpk\" data-start=\"7150\" data-end=\"7179\">Is the Saylor narrative shifting?<\/h2>\n<p data-start=\"7181\" data-end=\"7376\">The Saylor narrative isn\u2019t collapsing completely. Strategy still holds massive Bitcoin reserves and recently invested billions more in BTC. There\u2019s no talk of a retreat from Bitcoin.<\/p>\n<p data-start=\"7378\" data-end=\"7415\">But the narrative is getting more complicated. The simple story of \u201cStrategy keeps buying Bitcoin\u201d is turning into a more complex capital-markets story. It\u2019s now about preferred shares, dividends, capital raising, share dilution, financing costs, and potential tactical sales.<\/p>\n<p data-start=\"7659\" data-end=\"7926\">That\u2019s a big difference. Because the more complex the model becomes, the more investors need to understand the risks. Strategy isn\u2019t just a Bitcoin buyer. The company has effectively become a highly specialized capital-markets mechanism built around Bitcoin.<\/p>\n<p data-start=\"7659\" data-end=\"7926\">More <a href=\"https:\/\/www.coinpro.ch\/en\/news-en\/\">news about Bitcoin<\/a><\/p>\n","protected":false},"excerpt":{"rendered":"<p>For years, Michael Saylor has been seen as one of the loudest Bitcoin bulls in the corporate world. His company Strategy, formerly MicroStrategy, has evolved from a software company into one of the best-known Bitcoin treasury companies. But right now, the tone around the aggressive BTC strategy is changing. After a buying spree of around&#8230;<\/p>\n","protected":false},"author":6,"featured_media":42761,"comment_status":"closed","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"_lmt_disableupdate":"","_lmt_disable":"","footnotes":""},"categories":[17325],"tags":[],"class_list":["post-42760","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-news-en"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO Premium plugin v27.6 (Yoast SEO v27.6) - https:\/\/yoast.com\/product\/yoast-seo-premium-wordpress\/ -->\n<title>Michael Saylor under pressure: Is Strategy getting more cautious with Bitcoin? - CoinPro.ch<\/title>\n<meta name=\"description\" content=\"Strategy pauses after billion-dollar Bitcoin buys. 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