Rocky Agrawal says hi

I woke up Sunday morning to an unexpected e-mail from my Bay Area pal Rakesh Agrawal: Friday afternoon, he’d quit the high-ranking job at PayPal he’d started only weeks earlier and was starting a new company.

A quick check of Google showed that Friday night, he’d gone on some sort of Twitter rampage – a stream of tweets, many incoherent and some talking trash about his now-former colleagues, and of course somebody screen-capped them all before he’d deleted what he said were supposed to be direct messages. Saturday afternoon, PayPal’s Twitter account suggested he’d been canned, reporting that he was “no longer with the company.”

Monday morning, he got on a plane from New Orleans to Newark, after which the Twitter strangeness continued: a string of reports about a phone’s declining battery, veiled insults about former co-workers, requests for a new iPhone, some outright gibberish. After a few lucid tweets following a nap that acknowledged people’s concerns, the tweetstorm got hard to follow all over again. Mutual acquaintances, one of who’s known him much longer than me, started asking about his well-being. I had the same question in mind.

So I met him for dinner with no idea what to expect. I can report that contrary to the Hunter S. Thompson-esque persona he’d been creating, he seemed in command of his wits and confident in the ultimate success of his social-media strategy. In my experience, he has not been a dummy or a newbie on that subject, which has made all of this so confounding to watch. It’s… well, not how I went about publicizing my departure from my old employer.

We talked for a little while about people he’s liked at AOL, Twitter and PayPal and hiring and retention practices he didn’t like at those places–the kind of banter I’ve had more than once with other tech-industry types–and he invited me to record and post that conversation. Have a listen if you want, and please forgive the crummy audio quality caused by recording at a crowded bar:

Note that as he was saying a few nice things about PayPal president David Marcus (whom I met last year at Mobile World Congress and thought a pretty sharp guy), Marcus was posting a note on PayPal’s blog denouncing Rocky’s “mad rants.” My friend no longer seems so fond of his old boss, going by this a.m.’s tweets.

We also discussed the company he’s planning to start up–I can’t report much about that, owing to Rocky revealing so little–and for which he says he has ample funding. There was a vague job offer too. He does not have my answer yet.

10:27 a.m. Revising and extending my remarks to answer one question: So how do I know this guy? Rocky worked at the Post during some of its earliest and more awkward ventures into online publishing, although I didn’t get to know him all that well until years later. If management had listened to people like him who grok user experience and customer behavior (see also: being right about Groupon’s business-model weaknesses way before a lot of other people), my old industry might be in better shape. Don’t count the guy out, in other words.