The co-founder and chief executive of self-destructing messaging app Snapchat might wish his own app existed when he studied at university after old emails and instant messages emerged.
In the emails, Evan Spiegel describes urinating on a woman, helping his friends get sex from intoxicated "sororisluts" and getting high.
Drinking underage (by far the most moderate of the revelations), stripper poles and pointing lasers at "fat chicks" are also mentioned.
"F--k, I hope we finish this keg before the PhiPhis get here," reads one of the more tame messages. Most of the other messages are too lewd to be republished by Fairfax Media.
The leaked messages mostly originate from 2010, when Mr Spiegel, then aged between 18 and 19, was a prominent member of the Kappa Sigma fraternity at Stanford University in California.
Published on Thursday on Silicon Valley gossip website ValleyWag, the leaks prompted Mr Spiegel, now 23, to issue a statement saying that he is "mortified and embarrassed" by the "idiotic" messages from his frat boy days.
"I have no excuse," he told TechCrunch. "I'm sorry I wrote them at the time and I was [a] jerk to have written them. They in no way reflect who I am today or my views towards women."
The messages are reminiscent of leaked instant messages from Facebook founder Mark Zuckerberg in 2003, published by Business Insider in 2010.
"Yeah so if you ever need info about anyone at Harvard. Just ask," the instant message conversation read. "They 'trust me' . . . Dumb f---s."
TechCrunch journalist Jordan Crook said Mr Spiegel's messages displayed "the worst of the 'bro' mentality that continues to contribute to the marginalisation of women in Silicon Valley".
"As Snapchat moves towards monetisation, which could very likely include partnerships with big brands, the collegiate douchebaggery of the CEO may make that process much more difficult," she said.
No stranger to controversy, Snapchat earlier this year filed for a temporary restraining order against Frank Reginald Brown, who claims he came up with the idea for the app that sends photos and messages that self-destruct once viewed.
Earlier this month, Snapchat settled claims by the US Federal Trade Commission that it deceived users by falsely promising its photo messages disappeared.
The company has raised tens of millions of dollars in funding over the past year, despite a high-profile hacking attack. It remains to be seen if Thursday's revelations will have an impact on investors or users.
In November, Snapchat shocked the tech community when it rejected a $3.2 billion acquisition offer from Facebook.
"There are very few people in the world who get to build a business like this," Spiegel later told Forbes magazine. "I think trading that for some short-term gain isn't very interesting."
Forbes calculated that Mr Spiegel and Snapchat co-founder Bobby Murphy – who Mr Spiegel labelled in one of Thursday's leaked messages as once being "really high" – would each have received $US750 million from the Facebook offer.