Since its listing, Circle's stock price has continued to soar, with CRCL rising from its IPO 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 have instead become the "disappointed ones" who missed the main wave of growth. Many of them chose to sell on the IPO day and missed out on potential gains of billions of dollars in just two weeks. This not only reveals a serious misjudgment of market expectations but also reflects the cognitive gap between the primary and secondary markets in the new era of crypto finance. When even the founders fail to anticipate the true value of their own stocks, we may need to rethink: in this era full of narrative-driven and emotionally leveraged investments, who is the real smart money?

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

As of June 6, 2025, the potential gains missed by these early sellers amounted to as high as $1.9 billion. It was less about selling and more about "losing out by not buying"—their choice was nothing short of painful.

These executives and VCs cashed out at $29.30 per share, collectively receiving approximately $270 million. But if they had held on for just a few more weeks, the value of their shares would have been worth billions of dollars.

CRCL Reaches New High: Founders Miss Out on $330 Million, Early Shareholders Miss Out on $1.9 Billion

Take Circle's Chief Product and Technology Officer as an example. He sold 300,000 Class A common shares in the IPO at $29.30 per share. If he had not sold these shares, by last Friday's close, their value would have reached $240.28 per share. In other words, he personally missed out on potential gains of about $63 million.

CRCL Reaches New High: Founders Miss Out on $330 Million, Early Shareholders Miss Out on $1.9 Billion

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

Even founder Jeremy Allaire was not spared. He sold 1.58 million shares in the IPO at $29.30 each. If he had held on, he would now have an additional $330 million in paper gains.

Circle VC Misses Out on Billion-Dollar Gains

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 shares brought them a substantial cash-out gain of $270 million, the "opportunity cost" of this transaction just two weeks later was staggering.

If they had chosen to hold on to these shares, they would have made an additional $1.9 billion.

Objectively speaking, some VCs only sold a portion of their holdings in the IPO. For example, the well-known venture capital firm General Catalyst sold only 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.

The situation for founder Jeremy Allaire is similar; he still holds over 17 million shares and has options and restricted stock. Many other venture capital firms and company executives have also retained a significant proportion of their initial investments.

But even so, the decision to sell at $29.30, with CRCL's stock price now soaring to $240.28, still seems quite awkward. While no one can predict the future, a prediction error as high as 88% is undoubtedly a "shocking misjudgment" and has already earned its place in financial history.