Executives regret cashing out: CRCL hits new high, Circle's early investors sell $2 billion

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Original Author: Protos

Original Translation: Ismay, BlockBeats

Original Title: CRCL New High, Circle Executives and VCs Collectively Sell Off $2 Billion


Editor's Note: Since its listing, Circle's stock price has continued to soar, with CRCL rising from an initial price of $29.30 to $300, becoming one of the biggest winners at the intersection of Wall Street and the crypto world. However, in this equity feast of the stablecoin leader, the earliest executives and venture capitalists became the "disappointed" ones who missed the main wave of growth. Many of them chose to sell on the day of the IPO, missing out on potential billions in earnings within just two weeks. This not only reveals a severe misjudgment of market expectations but also reflects the cognitive disconnect between primary and secondary markets in the new era of crypto finance. When even the founders couldn't predict the true value of their own stock, perhaps we should rethink: In this era driven by narrative and emotional leverage, who are the truly smart money?

Following is the original content:

Executives and venture capitalists who chose to sell stocks in Circle's (ticker: CRCL) IPO missed a stock price surge comparable to a rocket launch.

As of June 6, 2025, the potential earnings missed by these early sellers amount to $1.9 billion. It would be more accurate to say they "lost by not buying" - their choice can be described as painful.

These executives and VCs cashed out at $29.30 per share, totaling approximately $270 million. However, if they had been willing to hold for a few more weeks, the value of their stocks would have reached billions of dollars.

Take Circle's Chief Product and Technology Officer as an example, who sold 300,000 Class A common shares in the IPO at $29.30 per share. If he had not sold these shares, they would have been worth $240.28 per share by last Friday's close. This means he personally missed out on potential earnings of about $63 million.

Circle's Chief Financial Officer also sold 200,000 shares at the same price during the IPO, missing out on earnings of about $42 million.

Even the founder Jeremy Allaire was not exempt. He sold 1.58 million shares in the IPO at $29.30 per share. Had he chosen to hold, he would now have an additional $333 million in book earnings.

Circle VCs Miss Billions in Potential Earnings

In Circle's Initial Public Offering (IPO), venture capital firms, executives, and other insiders collectively sold at least 9,226,727 common shares at $29.30 per share.

While these stocks brought them a substantial cash-out of $270 million, the "opportunity cost" of this transaction became apparent just two weeks later.

Had they chosen to continue holding these stocks, they could have earned an additional $1.9 billion.

Objectively, some VCs only partially reduced their holdings in the IPO. For example, the well-known venture capital firm General Catalyst only sold about 10% of its CRCL shares. According to its latest Form 4 filing with the U.S. Securities and Exchange Commission (SEC), the firm still holds over 20 million shares.

Founder Jeremy Allaire's situation is similar, as he currently holds over 17 million shares and has options and restricted stocks. Many other venture capital firms and company executives have also retained a significant portion of their initial investment.

However, the decision to sell at $29.30, against the backdrop of CRCL's current stock price of $240.28, still appears awkward. While no one can predict the future, a prediction deviation of 88% is undoubtedly a "shocking misjudgment" that has already secured its place in financial history.

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Disclaimer: The content above is only the author's opinion which does not represent any position of Followin, and is not intended as, and shall not be understood or construed as, investment advice from Followin.
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