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The ongoing crypto winter has forced <a href="https://www.thestreet.com/crypto/markets/michael-saylor-predicts-bitcoins-next-decade" rel="noopener noreferrer nofollow">Michael Saylor</a>'s <a href="https://www.thestreet.com/crypto/markets/wall-street-predicts-170-upside-for-microstrategy" rel="noopener noreferrer nofollow">Strategy</a> (Nasdaq: MSTR), formerly MicroStrategy, to sell Bitcoin (BTC) twice this year.
<ul>
 <li>32 Bitcoin for around <a href="https://www.thestreet.com/crypto/markets/michael-saylor-breaks-his-most-famous-promise" rel="noopener noreferrer nofollow">$2.5 million </a>during May 26-31</li>
 <li>3,588 BTC for <a href="https://www.thestreet.com/crypto/markets/michael-saylors-strategy-sells-bitcoin-again" rel="noopener noreferrer nofollow">$216 million</a> during June 29-July 5</li>
</ul>
The company has sold Bitcoin for the first time after 2022. Now, another major digital asset treasury company has been forced to sell Bitcoin.
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</ul>
<h2 id="the-smarter-web-company-sells-a-portion-of-bitcoin-stack">The Smarter Web Company sells a portion of Bitcoin stack</h2>
The Smarter Web Company <a href="https://www.smarterwebcompany.co.uk/smarterweb-co-uk/_img/pdf/news/2026-07-23-smarter-convert.pdf" rel="noopener noreferrer nofollow">disclosed</a> on July 23 that it sold&nbsp;177.8909127 Bitcoin worth $11.68 million and used the proceeds from the sale to repay an $11.7 million convertible debt facility.
Though a company selling Bitcoin during a period of crisis can be interpreted as a sign of falling confidence in the cryptocurrency, the&nbsp;company said it made the sale decision in preference for balance-sheet flexibility over equity dilution.
Otherwise, it would have to&nbsp;issue 7.71 million common shares, which would have diluted existing shareholders had the convertible been converted into equity instead.
<blockquote>
 "When we entered into Smarter Convert in August 2025, it provided an innovative alternative to traditional leverage," The Smarter Web Company CEO Andrew Webley said.&nbsp;"The structure enabled us to strengthen our balance sheet whilst maintaining flexibility during an early stage of our Bitcoin treasury strategy. As the Company has evolved, so too has our approach to capital allocation.&nbsp;Looking ahead, whilst we continue to recognise the potential benefits of both fiat and Bitcoin-denominated convertible instruments, we do not currently believe they represent the right capital solution for The Smarter Web Company."
</blockquote>
It still holds&nbsp;2,700 Bitcoin on its balance sheet.
<figure>
 <figcaption>
 BTC/USD, Source: <a href="https://app.decibel.trade/trade/BTC-USD" rel="noopener noreferrer nofollow">Decibel</a>
 </figcaption>
</figure>
Bitcoin was exchanging hands at $63,886 at the time of writing,&nbsp;<a href="https://app.decibel.trade/trade/BTC-USD" rel="noopener noreferrer nofollow">as per Decibel</a>.
<a href="https://www.thestreet.com/crypto/markets/billionaire-doubles-down-on-orange-juice" rel="noopener noreferrer nofollow">Related: Billionaire doubles down on Orange Juice</a>

After MicroStrategy, another crypto company sells Bitcoin

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