It's hard to cast a better clusterfuck—or a worse caricature of Silicon Valley hustle—than what happened to tech investor Jason Calacanis. "Someone hacked my voicemail and changed my outgoing message to get me to invest," he wrote on Instagram yesterday, along with a recording of the new message.

That someone was Avi Zolty, a graduate of Y Combinator, the prestigious Mountain View accelerator and the founder of Skurt, a startup that promises to "disrupt the $24bn a year US car rental market." (It's never a good sign when your pitch starts with hackneyed buzzword, followed by a meaningless number about the size of a market.)

Zolty also thought it would be a good idea to write about his brainless scheme on Medium, in a post that since been deleted:

I figured the kind of people calling Calacanis would be the ideal demographic to target for our seed round.

Jason, if you're reading this. I'll be happy to reset (You can reach me at avi@skurt.co). This wasn't meant to be a malicious hack, but rather a simple social experiment to see how much traction/investor interest I could get.

Zolty got the voicemail idea after noticing that Calacanis and Tim Ferriss, the one-man lifehacker bro brand, had the largest syndicates on AngelList, an investment platform. (Think of AngelList syndicates as sort of loosely-policed popularity contest to help regular people part with their money.) In his post, Zolty also accidentally revealed that there was precious little technical know-how involved in this "hack."

Besides the legal implications for people who break into personal accounts for sport, just look at all the brands names involved in this incident: Y Combinator, AngelList, Medium—even the victim, inveterate bombast Calacanis. On Hacker News, an industry message board run by Y Combinator, commenters laid the blame on the lawlessness currently in vogue among startups with multi-billion valuations, and encouraged by Y Combinator:

If only he'd found a way to systematically make money by breaking the law and "disrupting" things, he'd be getting a valuation in the billions.

People are told to "hustle", "be naughty", and "break things" - and are applauded for it in founder stories. Small wonder something like this happens.

A natural extension of "it's easier to apologize later than to ask for permission."

I'm curious to see how this plays out in terms of YC's response, because as a prominent player and popularly accepted thought leader in the start up "industry", their response will set the tone and draw the line in what is seen as acceptable for " getting things done ".

The EFI fine [1] demonstrated that it often pays to be illegal. The banks demonstrate this on a regular basis with their paltry funds and settlements. Will startups/small-tech follow suit? (Well, maybe only towards lay people rather than investors with power and money. Today's lesson: don't mess with people who actually have power!)

Those commenters were anonymous. Reddit alumni Mike Schiraldi also weighed in on Hacker News:

I know [Y Combinator cofounder Paul Graham] looks upon a certain amount of "naughtiness"[1] as a potentially positive indicator, but it should be clear to anyone with an inkling of common sense that this is way over the line.

[1] http://www.paulgraham.com/founders.html

YC couldn't have been that surprised by this tactic. On AngelList, Zolty includes turning phishing into a game as his first credential for entrepreneurship:

Created 170,000 + daily active gamified social phishing site in high school. Ran multiple record breaking successful event promotion companies. Ran marketing at top ten nightclub. Early Bitcoin pioneer. Y Combinator winter 2013.

Y Combinator president Sam Altman apologized for the incident on Twitter and on Hacker News:

We expect ethical behavior from our community, and this fell well short of that standard. Obviously we didn't suggest or approve it, but we are still sorry it happened.

"Ugh" indeed. When I asked Altman if YC had taken any further action against Skurt, he wrote by email: "yes, obviously. we take violations of our ethics policy really seriously," but declined to specify, adding, "pretty sure responding to a reporter with details about something like this is against every HR practice i've ever heard of."

Calacanis said he does not intend to press charges and—with the last of his phone battery—posted his email to Zolty on Twitter:

Just what we needed: another #gate.

To contact the author of this post, please email nitasha@gawker.com.

[Image via Instagram]