Did Circle’s Biggest Investors Really Leave Money on the Table? The $430M Missed Profit Mystery

The Numbers Don’t Lie

When Circle priced its IPO at $29.30 per share, it wasn’t just a market launch—it was a verdict. A billion-dollar valuation for a stablecoin issuer that promised financial sovereignty. But behind the glossy charts, something quietly unsettling emerged: early investors who could’ve made billions chose to cash out early.

IDG Capital—China’s legendary tech backer—sold \(68 million worth of shares on day one. Their remaining stake? Still worth over \)447 million. That means they walked away with less than 15% of what their original bet could’ve been worth today.

I stared at the numbers until my eyes burned. It wasn’t greed. It wasn’t incompetence. It was… doubt.

Who Walked Away—and Why?

General Catalyst sold over 350k shares at \(29.30, raking in \)104 million—enough to fund ten startups. But now? That same stock is trading near \(214. They missed nearly **\)650 million** in paper gains.

And then there’s ARK Invest—the bold ones who bought big on Day One, then sold off aggressively as prices soared. Their total take: over $350 million in profits—not bad for a single asset class run by Cathie Wood’s team.

But here’s the irony: even after selling huge chunks, they still hold CRCL as a core ETF position.

It feels less like financial discipline and more like performance theater—showing you’re smart enough to exit just before the crash… if only you knew when it would come.

CEOs & Executives: Profiting While Building Power

Jeremy Allaire, Circle’s CEO and co-founder, didn’t just sell—he restructured his entire ownership model. He converted 18 million shares into B-class stock (same economic rights, stronger voting control), then sold part of that pile for $46 million.

Smart move? Absolutely. But also… telling? He kept control while taking liquidity—not exactly egalitarian leadership.

Laterally: CFO Jeremy Fox-Geen sold 200k shares for around \(585k—but he also bought back with options at just \)10 per share, still holding over 127k unexercised ones with 6 years to go.

Meanwhile CPO Nikhil Chandhok pocketed $22 million from sales—yet still owns over 60k shares worth more than $13M today.

The pattern is clear: those closest to the code get paid first—and keep influence long after profit-taking ends.