Were you unable to attend Transform 2022? Check out all of the summit sessions in our on-demand library now! Watch here.

Another week, another embarrassing tech CEO gaffe. This time, it was beloved sexting app Snapchat’s leader who found himself “mortified” when the immature and misogynistic emails his college-self sent were leaked to the press.

In case you need to catch up on those, they were pretty standard frat bro emails sent to the house email listserve — degrading sorority girls, talking up the house’s brothers, and graphically describing a lot of acts that were likely inspired by ego and porn. But you can take a look at the writing itself over at guilty-pleasure tech gossip blog Valleywag. (Bonus: Take a look at the Stanford administration’s reaction.)

Naturally, given Evan Spiegel’s age, personal background, and the fact that he more or less created an app for sexting (though it turned out it’s not as ephemeral as we thought), the Internet said a collective “duh” to the news, despite giving it ample news coverage, as well.

But one thing that is making this an interesting situation is its timing.

This is at least the third case of a male chief executive of a tech company in the past month or so to make headlines for blatantly misogynistic behavior — the others are RadiumOne’s Gurbaksh Chahal and Rap Genius’s Mahbod Moghadam. (GitHub’s Tom Preston-Werner comes in at a distant runner-up for aggressive, plausibly non-sexist behavior in the office.)

Furthermore, both execs were asked to resign or fired as a result of their actions, so the current question is how Spiegel’s case will play out.

A tale of three misogynistic cases

While these other cases don’t necessarily mean they will predict what happens with Spiegel, it’s important to take a quick look at their respective circumstances and outcomes.

In Chahal’s case, he was charged with beating his girlfriend last summer, and though security footage of him hitting her 117 times surfaced, the courts did not admit it as evidence (it was seized without warrant). Ultimately, Chahal accepted a plea bargain to misdemeanor charges and a $500 fine. However, RadiumOne’s board, which he claims urged him to take the deal, subsequently fired him.

Rap Genius cofounder and then-chief executive Mahbod Moghadam unfortunately decided to post online some incredibly controversial and insensitive comments about the disturbing manifesto written by Elliot Rodgers, the 23 year-old man who killed six and wounded 13 this past weekend. He was allegedly fired the next day by his cofounders, though the company claims he resigned.

And here, we have a 23 year-old who is haunted by emails he wrote in college, two years before Snapchat’s official founding date, and confirming his character as we already knew it. My guess is that nothing will happen to him.

“I mean, there is the investor hat and there is the ‘I was once a young dumb college student’ hat,” said one investor to us, who wishes to remain anonymous.

“The guy clearly had a complete misjudgment. But we’ve all done stupid shit. Maturity comes with age,” North Bridge Venture Partners partner Paul Santinelli said to VentureBeat.

That’s their point: These emails show Spiegel acting like a particularly horrible 19-year-old when he was 19 years old. Our male-dominated investor club here in tech may be all grown up now, but they quietly remember their own days of bro idiocy — or when their own friends, at the very least, behaved that way. It would really be hypocritical for them to burn him at the stake.

We spoke with Antone Johnson, former MySpace and eHarmony attorney who also works with many Bay Area and Los Angeles-based startups about whether Spiegel could get forced out. Johnson said it seems unlikely from a legal point of view.

“How much do people really care about that stuff when they enjoy the product?” said Johnson.

“VCs almost never, at least in my experience, invest in the adult entertainment industry. ‘We can’t be seen to be in this sleazy business, we need to have this defensible investment approach,’” is the general attitude of investors, Johnson said.

Johnson also said that in larger corporations and even larger startups, the boards will often sign contracts with the executive team with very carefully worded language about causes for firing such — we’re talking felony convictions or directly harming the business’s finances. See case of Chahal, most likely.

What now?

Some of the questions now are what will current and potential investors be concerned with –and what about Snapchat’s current and potential female employees?

“My number one question is what else is out there? When you know the extent of what’s embarrassing and damaging, the best idea is to get it out and take responsibility. … You don’t wanna get hit again and again,” said Johnson.

This is especially true if the company is looking to go public soon or another event that could be derailed by more dirt coming out.

“What would it take, potentially, if more came out … to have [Spiegel] step aside? Or is it even a possibility?” said Johnson.

Johnson added that if he were an investor considering an investment in Snapchat during its next round, he’d probably want some legal provisions to keep Spiegel from sinking the company with some new embarrassing behavior.

“This is a great opportunity where an investor would sit down with the guy and say, ‘You’ve got to think about this, and make sure this doesn’t happen again. You ate crow — and you move on.,'” said Santinelli.

We can all recall when Clinkle, also run by a young Stanford graduate, brought in some “grownups” to the executive team to help the young CEO stay away from embarrassing photos, among other things.

But can that really work? Is 23-year-old Spiegel that much different from 19-year-old Spiegel?

As a 23 year-old, myself, I’m skeptical. I know plenty of men my age who still make such comments, and I know 30 year-olds that still behave like this.

And in case you were wondering, Snapchat does have several female employees, and they’re likely feeling a combination of disgust and lack of surprise. We’ll have to see what sort of hiring magic the company will whip out when a female job candidate brings up her discomfort with a CEO who may potentially view her as an object.

VentureBeat's mission is to be a digital town square for technical decision-makers to gain knowledge about transformative enterprise technology and transact. Discover our Briefings.