Kleiner Perkins sold their stake back to Sahil Lavingia for $1.
After raising a $7M Series A, Gumroad couldn’t close a Series B.
Despite growing steadily (~60–80% annually), VCs didn’t see hypergrowth. Sahil calls this the real VC trap: being “good but not great.”
Instead of selling or shutting down, he downsized, ran lean, and made Gumroad profitable. A few years later, Kleiner reached out:
“We’d be interested in selling our stake back to you for one dollar.”
That was the entire email.
Why would a top-tier VC do that?
Today, Gumroad runs like a mini public company: profitable, lean, distributing dividends, and running share buybacks via open auctions.
Early investors who got in at $0.60 have sold some of their shares back at $4+.
There’s real math behind this “third path” between unicorn success and total failure. It demands strong unit economics and ruthless operational discipline but it works. Most founders don’t even consider it.
We’re taught to think binary: unicorn or bust. But the middle path (profitable, sustainable, customer-first) can often win in the long run.