VCs often get a bad rap. The truth is that the startup ecosystem simply wouldn't exist without them, and the smart investment on the part of multiple different individuals and firms have led to some of the great technological advancements we enjoy in our day-to-day lives.

But sometimes the ridicule is deserved. There's no shortage of VC stereotypes and jokes online, where founders rip on VCs and VCs rip on founders in a never ending cycle of biting the hand that feeds the hand that feeds. But are all the criticisms warranted? What exactly have VCs done to deserve all the hate? In this article, we've listed 10 of the craziest VC tweets out there that encapsulate stereotypes, missteps, and cliches for which the profession is often ridiculed.

Joshua Baer has no hobbies

Starting off our list is Joshua Baer, an investor and co-founder of Austin-based startup incubator Capital Factory, who has some advice for the hungry masses who beg him day in and day out to tell them the secret to his productivity.

“Lots of people wonder how I get so much done and think that I must work all the time and not have any hobbies (not true),” Baer tweeted. “My answer — I don’t watch TV shows or follow sports.”

The secret to getting things done is apparently to not watch any TV shows or sports, which, according to Baer’s take, don’t seem to qualify as real hobbies. A titan of inspiration, Baer’s tweet almost immediately drew ridicule, going viral on VCBrags where it got put through the wood chipper:

“It’s simple, just don’t watch TV, and have your parents pay for you to attend a $60,000/year university,” wrote one user.

“What is wrong with VCs. There seem to be so many like this,” another mused.

Simultaneously dunking on completely normal behavior and puffing one’s own strange behavior, Baer’s tweet is a classic example of VC braggadocio. A perfect encapsulation of what makes laughing at VCs on Twitter so easy. This is truly the blueprint. A 10/10.

Sequoia Capital’s terrible minions tweet

There’s a lot to unpack here.

I’m not sure what’s more concerning: the author’s utter failure at writing a limerick, the decision to use a minion meme in 2020, or that it apparently took them an entire day to craft this specimen of a tweet. With a combination of limericks and minions so terrible it has Ogden Nash doing body rolls in his grave, Sequoia India has succeeded at crafting a tweet so bizarre that it would send any founder shirking away in embarrassment.

Sequoia Capital’s India branch, which has invested in giants like Gojek, Oyo and Truecaller to name a few, posted this tweet to celebrate the announcement of recent investment Airmeet’s $12 million Series A. Airmeet specializes in hosting virtual events — the investment is a reasonable strategy during a pandemic when offices globally are working remotely.

So really, the story behind this tweet is not that strange at all. But this tweet lands here because of the strange attempt at being relatable and failure to even stick to their own format. This feels like something your weird aunt would post on Facebook, not something that belongs on twitter. But to their credit, Sequoia’s audience seems to be lapping it up, and it’s good at the 1-2 punch of audience engagement.

“Let Me Know How I Can Be Helpful” just isn’t helpful

One of the least desirable VC stereotypes is the one that kicks back after tossing in cash, tosses an open ended offer to help, and pats themselves on the back for being innovative. These VCs often toss in a hated term during the process: “Let me know how I can be helpful.” The term is so hated that an entire Twitter account dedicated to ripping it apart has popped up.

Enter Leo Polovets, a co-founder and partner at early-stage VC firm Susa Ventures, which has put money into companies like Fast and Robinhood. Polovets quote tweeted a thread criticizing the infamous statement in defense of it. 

“‘Let me know how I can help?’ is overused, but it's often genuine and also literal,” Polovets wrote. “I say it frequently and mean it. But the number of people who reply with areas where they want help is maybe 3%. And then everyone complains that the offers to help are disingenuous :-).”

The response was less than great. Many were baffled by the decision to defend the use of the line. Blockparty founder Tracy Chou responded with a much more popular tweet reinstating ridicule which makes Polovets’ defense look silly in retrospect. If anything, testimonials from founders show they actually want active VCs who add value beyond the dollar amount.

In truth, Polovet’s statement isn’t that “crazy,” but it is a pretty needless self-own in defense of something that needs no defending, serving as a stand in for VCs who may be more concerned with talking away stereotypes than actually working to defy them. Sorry, Leo — you drew the short end of the stick on this one.

Mr. Real Estate Man

Keith Rabois is one of the bigger names in VCs and tech. A prolific investor and board member at multiple tech companies, Rabois has either invested in or served on boards of companies like Square, Paypal and Yelp. He’s also a controversial figure, known for his outspoken support of president Donald Trump and his fiery Twitter posts, none more fiery than this one from September 10.

“I know more about residential real estate than probably any one person in the U.S.,” Rabois wrote.

The tweet was in reply to a post from another VC casting doubt over whether the mass exodus from the Bay Area was in fact happening, or just a Twitter fantasy. The prior post had said they owned a portfolio company with significant real estate investments that didn’t reflect the trend, and Rabois responded with the above tweet’s stunning empirical evidence.

The thing is, maybe Rabois does know more about real estate than most people. The man is a co-founder of a residential real estate startup seeking to disrupt the industry, which he had been tossing around ideas for with Peter Thiel since 2003. But what makes Rabois’ tweet worthy of ridicule is the utter lack of humility, sweeping dismissiveness and the fact that it was part of an epic series of angry tweets on the same day, all full of similar outlandish statements such as when Rabois called his great intellect on the subject “factually true and empirically verifiable.”

Naval Ravikant’s guide to getting rich

Many investors are “prolific,” but few have as tight a grip on the descriptor as Naval Ravikant. With investments in hundreds of companies and a podcast called “spearhead” from which he provides life and financial advice, Ravikant’s persona is more than that of an average VC; he paints himself as a thought leader and life coach.

His Twitter page is a perfect example of this. Ravikant has amassed over one million followers while following exactly none — either he’s made efficient use of Twitter lists or has a burner account where he follows people — and uses his following to disseminate inspiring messages and mantras like “if you want to make the wrong decision, ask everyone” and “the price of trying to make everyone happy is making yourself miserable.” 

But no post of Ravikant’s is as easy to pick on as his pinned thread, which is an epic-length guide on “how to get rich without getting lucky.” There’s plenty of decent advice to be found in there — he tells people that they need to work hard, build things others haven’t, and to partner with good people. 

But the issue is that Ravikant’s guide to getting rich is rather dependent on already being rich. The very first step in his guide is to “seek wealth, not money or assets,” though he leaves out the fact that it’s difficult to acquire wealth without first acquiring money or assets. He says the only way to get financial freedom is to own part of a business, without explaining that that, too, requires money in advance. He says that the best way to succeed is to pursue your specific passions and curiosity, but leaves out that most people literally can't afford to devote themselves to a passion. All this advice makes sense in a vacuum or a self-help book, but there’s no acknowledgement that the tools to do such things are cut off from most people.

With his faceless profile, lack of descriptors, and refusal to post anything but inspo lines, Ravikant’s thread and entire Twitter page really are not that different from Rabois’ angry rants. His online persona coldly implies that he’s reached a state of enlightenment that only vast wealth and equity can provide access to, making all of his worldly advice cynical.

Sahil Lavingia says stop Zooming

Sahil Lavingia, founder of Gumroad, has a Twitter page that’s not all that different from Ravikant’s. While his posts are not exactly "crazy," and actually have unique takes on tech and founding companies, Lavingia sometimes posts the sort of vaguely inspirational quotes that coyly walk around advice. It’s hard to find just one to nominate, but there are several that will make no sense on your first read and will require you to pick them apart first. 

Two examples are “Good hiring looks a lot like firing yourself,” (Translation: Hire people who are better at your job than you are) and “The more you Zoom, the less you zoom” (Translation: stop having needless meetings).

Lavingia seems to like to keep his numbers clean, as he also follows no other accounts despite his own large following. Lavingia may not be the biggest culprit, but his tweets are sometimes precisely the example of what non-VCs poke fun at: self-aggrandizing, guru-like posts that espout vaguely inspirational ideas. Lavingia does have interesting things to say, but sometimes it might be better to just say it outright.

“Twitter shines at times like this”

Our next crazy tweet is unfortunately lost to time, and only exists in screenshots such as this one in reply to Jason Calacanis, which itself gives away what our number one crazy VC tweet is (don’t scroll up!). That’s because the person who wrote it, investor and TV personality Chris Sacca, wisely deleted it.

In 2015, a series of coordinated terror attacks took place in Paris. They involved the bombing of a restaurant, the Stade de France, and a mass shooting at a concert venue. The entire city and internet were thrown into disarray as these multiple terrible events coincided with one another and the world grasped at straws for information.

Around this time, Twitter had recently introduced its “moments” feature, which compiled tweets on an ongoing event like a news article. Twitter made a “moment” about the Paris attacks as they were unfolding, and Sacca, an investor in Twitter, took it upon himself to promote the new feature.

“Twitter shines at times like this,” he wrote. “Follow this moment for continual updates.”

Aside from it obviously being a terrible moment to promote your product’s new feature, Sacca’s tweet is infamous because Twitter precisely doesn’t shine at moments like this. Twitter is a prime platform for the spread of misinformation during live events, from elections to mass shootings to the night of the Paris attacks themselves. Sacca quickly deleted the tweet and apolgized for it, but the lesson clearly wasn’t learned — he’d repeat the mistake less than a year later during the Brussels bombings in March 2016. 

Away Luggage’s work culture is good, actually

On December 5, 2019, The Verge published an expose on luggage startup Away’s work environment, levying a number of accusations against then-CEO Steph Korey, who many workers described as cruel and building a bad work environment. The story caused so much drama at Away that Korey ultimately stepped down from her position as CEO.

But while everyone was criticizing Korey’s management style, Founders Fund principal Delian Asparouhov came to her defense.

“Is this Away article supposed to be a hit piece? I read it as a compliment lol,” he tweeted. “Reminds me of @micsolana's tweet; if company culture involves shots of whiskey, why not? You can opt into that. These millenial twats should try working for Elon sometime, he does all this...Idiots”

Asparouhob included screenshots from the article in question. Let’s zoom in on those and see what he read into as a compliment.

“Korey had referred to the team as ‘millennial twats.’”

Employees were asked to work exceedingly long hours and limit their paid time off… They were reprimanded for not answering messages immediately — even late at night and on weekends,” reads another.

These are far from the worst accusations in the article, which include calling employees “brain dead” in public Slack channels, refusing to pay overtime, and a 3am Slack tirade so bad that the company put an intermediary between herself and the team — whom Korey quickly fired.

While Korey’s behavior may drive rapid growth — which looks awfully pretty on a VCs portfolio page — it doesn’t drive longevity, the ability to hire competitive workers, or a brand that customers want to engage with. Asparouhov might only be seeing the former.

Kanye is the dream investor


We couldn’t make a list of crazy VC tweets without putting Ye on the list. Kanye has sadly become known for his unhinged Twitter rants, one of which from 2018 gave us this gem:

“We’d be a strategic investor. Not just a VC”

What’s so good about Kanye’s tweet is that it was detached from any other tweet in his rampage. That, and if it were posted by VCbrags or VCstarterkit, it would read like a parody of the exact type of statement VCs make: that they’re different from the rest of the pack, even if all they do is cut you a cheque and sit back on Twitter.

I can't believe this is real

It’s hard to come up with a snarky introduction to this one. This is a bad tweet of epic proportions. Imagine the worst VC tweet possible. Are you thinking of it? Good, because whatever you’re thinking of isn’t nearly as bad as this monstrosity I’m about to share with you.

Earlier this month, Twitter user Lawrence Hamtil tweeted the following:

“I know everyone is obsessing over politics, but I received a text from my brother that his wife’s father was killed in a head-on collision. Just another reminder that tomorrow is promised to no one and to make the best of each day.”

There’s nothing wrong with this, a sincere, mournful post from someone who just lost someone they know. What happened next is a different story.

“I’m so sorry for your loss,” replied Sarah Cone, founder at Social Impact Capital. “And know that my VC fund has invested in technology that can stop 86% of the deaths and serious injuries from car accidents. We don’t need to have this happen in the future.”

Like Sacca’s tweet but one hundred times worse, Cone gives new life to the term “ambulance chaser.” Even worse, she doubled down on the initial post in a reply about the company’s Series A that comes off with a shocking lack of self awareness.

Cone’s tweet represents the absolute worst of the worst of what a VC could possibly tweet — something offensive and removed from reality that attempts to promote their own investment at a wildly inappropriate time, and would likely send the founder comatose were they to see it.

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