Does Nick Denton wish he were Peter Thiel?

"Thiel makes me sick!" read the note from Gawker Media publisher Nick Denton. His oddly personal declaration was prompted by a brief in the New York Post about former PayPal CEO Peter Thiel's success as a hedge-fund manager. Thiel will make an estimated $500 million this year running Clarium Capital, a hedge fund. (We reported this a few weeks ago, boss.) It hit me hard: Could Denton actually be jealous of Thiel?

In a word, yes. I instant-messaged Denton — that's the only way he communicates, really — asking him to elaborate, and he replied: "Oh, just because he's got such a nauseatingly successful track record."

A British-born Financial Times beat reporter sent to cover Silicon Valley during the dotcom boom, Denton reinvented himself as a technology entrepreneur. He sold a dotcom events business, First Tuesday, in a luckily timed deal as the bubble was bursting. He briefly entangled himself in an online newsfeeds venture called iSyndicate before starting a direct competitor, Moreover (that's "more OH ver," you Yanks.) But he quit as CEO years before VeriSign bought the company. He's the first to admit that his success is more from good timing than hard work.

Denton's clearly wealthy. He owns a fancy loft in New York's SoHo neighborhood. He funded Gawker Media, as best I can tell, out of his own pocket. At the same time, he invested in other blog ventures like Treehugger and Curbed. But he's far, far short of Thiel's $500 million a year. In 2004, when he first courted me as a blogger, I asked him where he made his fortune. He gave me a vague answer about currency trading and investing in London real estate. Denton is familiar with the business of manipulating markets. He cowrote All That Glitters, a book on on the 1995 collapse of Barings Bank caused by one young trader.

Having observed Denton for years, I have to say this: He's never seemed happer than when working as an editor. I was almost sorry to replace him as Valleywag's editor a year ago, because he so clearly enjoyed the role. When he appointed himself editor of Gawker in January, it seemed more a homecoming than a temp gig.

That's why I found Denton's note so mysterious. Could he be unhappy as the blogosphere's success story? Does he wish he'd instead joined the lucrative hedge-fund world?

I'll admit I barely know the man. In an age of oversharing, Denton makes an art of revealing no personal details. That's what makes those four words stand out: "Thiel makes me sick!" I almost wish I hadn't asked him to explain himself.

(Photo of Thiel by David Orban; Denton by Matt Haughey)