Circle execs and VCs misread the market — it cost them $2B

Executives and venture capitalists (VCs) who sold shares into the initial public offering (IPO) of Circle (CRCL) missed out on a rocketship rally.

With at least $1.9 billion in opportunity costs through June 6, 2025, calculating the missed profits of selling instead of buying Circle’s IPO is painful.

As proceeds for their sales at $29.30 per share, these VCs and executives received about $270 million. Had they simply held those shares for a couple of extra weeks, those same shares could have been worth billions.

Circle’s chief product and technology officer, for example, sold 300,000 shares of class A common stock at $29.30. Had he not sold those into the IPO, he would still have shares worth $240.28 apiece as of Friday’s close.

In other words, selling at the IPO cost this executive $63 million personally in opportunity cost.

Similarly, Circle’s chief financial officer sold 200,000 shares of class A common stock at the same $29.30 price. His sale cost him $42 million in forsaken profit.

Even founder Jeremy Allaire sold 1.58 million shares at $29.30 during the IPO. Had he not sold, he would have had an extra $333 million today.

Circle VCs missed out on 10-figure gains

Overall, VCs, executives, and other insiders sold at least 9,226,727 shares of common stock at $29.30 per share during the IPO.

Their proceeds of $270 million were an impressive payday, yet just two weeks later, the opportunity cost of those sales has become breathtaking.

Had they not sold, they could have made an extra $1.9 billion.

Read more: ANALYSIS: Does the Circle IPO value Tether at $316B?

To be fair, some VCs only sold a portion of their CRCL position. General Catalyst, for example, only sold about 10% of its equity in the IPO. The giant VC still owns over 20 million shares as of its latest Securities and Exchange Commission Form 4 disclosure.

Allaire, similarly, still owns over 17 million shares plus options and restricted stock. Many other VCs and executives still retain a good portion of their initial investment.

Nonetheless, their sales at $29.30 certainly look like a faceplant in comparison to today’s $240.28. Although no one can predict the future, misforecasting it by 88% will be an embarrassing whiff that has already earned its place in financial history.