Venture capital and the great big Silicon Valley asshole game

By Sarah Lacy , written on October 6, 2014

From The News Desk

This piece originally appeared on PandoQuarterly, issue three.

Silicon Valley has an asshole problem, and it’s high time we owned up to it.

Let me be clear what I’m not talking about. I’m not talking about “brogrammers.” I’m not talking about Google buses, or the evils of libertarianism. I’m not even talking about greed, or at least not in that Gordon Gekko sense.

Nothing that follows is about the fringe behaviors that crop up whenever a hot ecosystem like Silicon Valley is observed from the safe and judgmental perch of East Coast media, and wildly extrapolated to apply to everyone who has ever run a startup.

Also, when I say “Silicon Valley” I really mean the tech startup ecosystem that’s centered here but stretches to New York, LA, and beyond. This article is a little about misogyny, but it’s principally about hypocrisy. That’s the real sin here.

That’s the problem.

I’ve covered the tech industry too close for too long to think of anyone as purely a hero or villain. I don’t expect that all great entrepreneurs are also people you’d want to set up on a blind date with your best friend, and I don’t expect that a VC’s job is to invest in the nice guy. The world just doesn’t work that way.

And thank God. If it did we wouldn’t have relational databases, iPhones, or any other manner of innovations that have improved our daily lives. And frankly, other industries like film, finance, or politics aren’t held to that sort of “good guy” standard. Why should high tech be? Just because we moralize about changing the world and doing no evil? (Yeah, we should probably stop that too, but that’s another article.)

Here’s the problem. Every venture capitalist, in every interview they’ve ever done will tell you the same casual lie: That they invest in people first and ideas second. They’ll tell you they invest only in people they’d want to work with. They’ll tell you that they have the luxury to say no to companies that don’t do things in line with the way they like to work, the way they like to treat people.

You don’t have to look too far into this year’s frenzied pace of dealmaking, and at the price tags of those deals to know that’s complete bullshit. In all too many cases, what venture capitalists are investing in is assholes.

It’s weighing on those who’ve been in the business for decades, and I've been having conversations about it all summer. A senior partner at a top firm recounted a partner meeting at breakfast recently.

“Why are we backing this guy?” he said to a younger rainmaker at the firm. “He’s an asshole.”

His partner replied: “Hey, you gotta get over it. It’s no longer about whether someone is an asshole it’s about can he make money.”

That conversation happened a year ago. Said this multi-decade veteran of the business: “It didn’t use to be that way.”

As an industry we need to think about what that means. Think about what the line is—either in terms of bad behavior or opportunity. Decide when an asshole is a functional asshole or just an asshole. Own it even. But most of all we need to stop lying to ourselves: This is an ecosystem with many successful nice guys, but they didn’t get funded by being nice.

Asshole rollcall

Let’s name some of the biggest perpetrators of what I’m talking about.

Snapchat. There’s been plenty of intrigue and rumors about the behavior and ethics of CEO founder Evan Spiegel around venture circles. He’s never been considered a warm and fuzzy guy, but the truly horrifying glimpse into his soul came from a batch of leaked college emails where he told his fraternity brothers to “have some girl put your large kappa sigma dick down her throat.” And that wasn’t even the worst. Spiegel has apologized, and the emails weren’t written while he was running Snapchat, but nor were they written that long before. More worryingly, unlike a lot of examples on this list, there appear to have been zero repercussions. Snapchat is rumored to be raising a round at a heady $10 billion valuation—including participation by the well-heeled Kleiner Perkins.

Uber. Where to begin with Uber? It’s a company that prides itself on playing rough and aiming to break laws. It has a self-described “war room” inside its new hard-edged headquarters. It’s played fast and loose with background checks on drivers and with the truth. A Pando investigation earlier this year showed that a driver accused of assault whom the company blindly defended had a criminal record that should have been caught in Uber’s background checks. More recently, it’s hired a campaign manager to shape the company’s narrative. This is an area CEO Travis Kalanick already knows plenty about, if we understand ‘shaping the company’s narrative’ to mean slinging mud and misleading the public in an image war between Uber and taxi companies.

Not only has Uber vilified riders accusing their drivers of rape, assault or general bad behavior, they’ve also betrayed all their drivers; Kalanick has said he can’t wait to replace them all with self-driving cars. Time and again, he’s shown he is loyal to little more than his growing bank account and to the all-mighty free market. The Verge recently exposed a campaign called SLOG, publishing internal documents that detail a plan for agents to pose as passengers to recruit drivers from competitor Lyft and vie to tie up their cars so they couldn’t pick up passengers.

Oh. And in a recent interview Kalanick bragged about how many ladies he could get with the success of the company referring to it as “boob-er.”

Uber has raised a jaw-dropping $1.5 billion, with its most recent $1.2 billion round coming at a rumored $17 billion valuation. No one doubts egomaniacal stories like the one where Kalanick publicly offered a job to a well-heeled investor at the elite Goldman Sachs conference who asked an astute question of the CEO. Still, he’s widely considered one of the best entrepreneurs of our age.

Secret. Most of the companies on this list and in this article do some good in the world, despite asshole-ish behavior on the part of the founders. You could even argue that the same qualities that make Kalanick and Spiegel such assholes are also what make them so incredibly effective as CEOs. Spiegel would need something a bit “wrong” with him to turn down $3.5 billion from Mark Zuckerberg, and Kalanick is just the kind of guy to think he can overturn the world’s most powerful transportation lobby city-by-city. Perhaps nice guys simply couldn’t do those things. But Secret is the lone exception to any of that, and hence, for my money, the worst one on this list.

The company exists for the sole purpose of writing things without accountability, and when Pando wrote about the concern for bullying and potential suicides, founder David Byttow replied on Twitter that we didn’t drive enough traffic to the site to address our concerns. This wasn’t really too much of a hypothetical. The app store ratings showed people actually boasting the service was a bully’s dream.

Astoundingly, his head of PR Tweeted that it was hard when people wrote things about her or her company without any accountability. Hey, at least we used our names. Only after a subsequent story was picked up widely, on the front page of the Huffington Post and in Fortune, did Byttow change his tune. Weeks later, the company grudgingly admitted there was no context in which you anonymously write nice things about someone. He did what we recommended and blocked any posts with specific names attached. Secret has raised $36 million—including a $6 million cash out for the founders.

Rap Genius. One of the most bizarre examples, in terms of a company engaging in bad behavior without suffering immediate repercussions, was Rap Genius, now called simply Genius. Co-founder Mahbod Moghadam was involved in a series of startling incidents before finally being forced out. These included shady practices that got the site penalized by Google and an annotation of the manifesto of Elliot Rodger, who stabbed three people and shot three others outside of UC-Santa Barbara. Moghadam noted it was “beautifully written” and speculated the killer’s sister might be “smokin’ hot.” The annotation was finally enough to have him pushed out of the company. However, a string of errors and abuses prior to this should have served as a warning of what was to come. And sadly, if Genius was doing as well as Snapchat or Uber, and he was the sole founder, he probably wouldn’t have been fired. The company has raised a whopping $56.8 million from some of the largest investors in the world.

Tinder. Tinder’s CMO Justin Mateen was accused by former VP of Marketing Whitney Wolfe of sexual harassment. She further accused the company, its CEO and its parent company IAC-owned of knowingly letting these abuses occur and wrongfully terminating Wolfe when she called the behavior into question. Mateen was suspended when the case came out. There are many unknown details of what actually occurred here and even more conflicting accounts in the press. But, as we wrote at the time, the news was unlikely to have any business repercussions for Tinder since it’s not an ad-based business model, and it’s already full owned by IAC and hence not open to the whims of venture investors. Further, it’s an app whose principle selling point is about making snap judgements based on someone’s appearance and keeping them or discarding them. Not exactly a “pearl clutching” crowd when it comes to this type of behavior.

Crunchfund. Many in the industry were agog when it was reported that Crunchfund had raised a second fund. Its controversial founder Michael Arrington (who is a Pando investor and was fired from our board two years ago) was accused by an ex-girlfriend of rape and abuse, a scandal that was widely reported and even written up in a large Vanity Fair profile back in December 2013. The claims were retracted after Arrington sued his accuser but following the claims, several other figures in the tech industry came forward to accuse Arrington of a pattern of abusive, bullying behavior to both men and women. But that didn’t matter. Even before the initial claims were retracted, investors had committed to a second fund.

And more to the point: Crunchfund wasn’t exactly killing it. The biggest hits had been investments in companies like Yammer and Tumblr which just got over the $1 billion Mendoza line. Even in those “hits” Crunchfund’s partners invested too little, too late for it to return the fund. Other early bets like Mailbox generated excitement but were acquired very early on.

A lot of this has to do with the bizarre co-dependent relationship between Arrington and AOL. AOL— which bought TechCrunch—took the majority of the fund both times, never mind this was a company that publicly and unceremoniously fired Arrington before sheepishly hiring him back because it needed someone to interview big name founders at its conferences.

These may be some of the more public examples, but they aren’t the only ones. And behind each of these are more reports of fucked over partners, promises made and then broken, and a general attitude that there are no repercussions for bad behavior. In fact, if you look at the valuations of Snapchat and Uber, it appears to be rewarded these days at higher and higher prices.

Sure, there are always assholes in entrepreneurship, partnerships, and life. But let’s compare today’s crop of mega-startups to the three biggest social hits of the early Web 2.0 wave: Facebook, Twitter, and LinkedIn.

People have debated the character of Mark Zuckerberg, but the people who know him best rarely call him an “asshole.” Driven, intense, arrogant? Sure. But he’s also assiduously calculating and controlled about the impact of his actions.

Every venture capitalist will tell you the same casual lie: That they invest in people first and ideas second.

Meanwhile neither of Twitter’s founders Jack Dorsey or Evan Williams are known as assholes—even though they effectively ousted each other and aren’t particularly close to one another today. Williams even personally bought investors out of Odeo—his previous company— because it didn’t turn out the way he’d hoped. He’s a rare example of a nice guy who finished first. His biggest flaw is his avoidance of confrontation.

And LinkedIn? Well founder Reid Hoffman could make Mother Theresa look like a jerk. The biggest investors in the early wave are much the same story. Peter Thiel is considered cold and even eccentric, but is known to be intensely loyal and principled. (Whether you agree with his libertarian principles or not.) Ditto Marc Andreessen. And Greylock’s David Sze is considered about as mean as Reid Hoffman.

There’s no denying that in less than ten years the caricature of consumer Web startup success has noticeably shifted.

"The truth is a lot of really successful entrepreneurs aren't [humble, high integrity] people." 

For months, I’ve talked to more than a dozen top venture capitalists in Silicon Valley about this wild hypocrisy in continually saying they only back good guys in the face of the obvious and mounting evidence to the contrary. None has argued with the premise—even when they are guilty of it. But none wanted to go on the record. The stakes are just too great. Well, almost none. There was one guy who’d just joined the VC ranks and couldn’t help but be honest: Eric Vishria.

When top Silicon Valley venture firm, Benchmark, named Vishria as its latest general partner, I was shocked. Not because he wasn’t deserving but because at a point in the cycle when everyone is obsessed with big names, big logos, big mouths, and big brands, Vishria is none of those.

With Vishria, they went for substance not flash. He’d cut his teeth at the least sexy of Marc Andreessen’s companies, Opsware, and his previous company, Rockmelt, ultimately failed, selling to Yahoo in a face-saving, comfortable landing for the team. Vishria isn’t a guy who drives headlines, but one whose level-headed judgment would matter tremendously in the board rooms of actual companies. I wrote as much at the time.

Here’s what I didn’t write then: Vishria's answer to my question of what baggage he’ll need to get over to become a successful VC at the legendary firm that’s backed eBay, OpenTable, Twitter, Yelp and, in more recent years, Uber and Snapchat. When I’d last seen Vishria, it was just after he sold Rockmelt. He looked exhausted and beaten. Around the same time, Andreessen told him he was “Valley depressed” and he’d know he was over it when he couldn’t have a single conversation without mentioning what could have been, but ultimately wasn’t.

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I was expecting him to answer my question about what baggage he had to get over with something about this heartbreak. Instead, what he said caught me off guard:

“I like working with a certain kind of person. I like working with people who are very smart, who have a little introspection, who have some humility, and high integrity. People that have some kind of honorableness about them. That’s how I attempt to carry myself. The truth is a lot of really successful entrepreneurs aren’t those kind of people. I think that’s something I have to watch out for. The models that work are not always created by those kind of people, and I want to be able to invest in them. That’s the biggest thing.”
Wow. Essentially, Vishria is admitting that investing with high integrity founders is no longer a luxury the venture world can afford. Particularly telling as two of his firm’s biggest hits are Uber and Snapchat. In fifteen years of covering this industry, I’ve never heard anyone be quite so honest on the record about this topic.

You can only lose your money once

For many I’ve spoken to, it’s hard to pinpoint when this new wave of assholes and our acceptance of them began. Part of it may be the changing face of what the “tech industry” is and hence what a “product guy” is. Kevin Rose of Digg—not known as an asshole—was one of the first high-profile examples of a “product founder” who advised on look and feel and design and usability and experience but couldn’t actually write a line of usable code. He hired an outsourced freelancer to do so in the early days of Digg.

Since then, with the advent of mobile apps designing something and shoving it out the door has gotten only more turn-key. Whether it’s the open source stack all this stuff runs on, platforms like Facebook or the app store for distributing it, the rise of services like oDesk and eLance, or hosting it all on Amazon Web Services, the “tech” part of a tech company has become commoditized—at least compared to the days when Silicon Valley actually made Silicon.

And because these founders need less money, they have fewer reasons to answer to anyone. Said differently: The assholes of the past may have lacked the freedom to let their asshole flags fly.

Not only has Uber vilified riders accusing their drivers of rape, assault or general bad behavior, they’ve also betrayed all their drivers

At a recent PandoMonthly LinkedIn CEO Jeff Weiner noted that being an asshole was way easier than putting in the work and showing the compassion required to be a good leader. If no one is challenging them, many will simply take the easier road. It may also be the sheer scale of the Valley startup machine these days. We should remember that plenty of “nice guys” are also getting handsomely rewarded. Drew Houston of Dropbox is hardly known for his bad behavior, nor is Brian Chesky of Airbnb, and yet they are the two most highly valued companies to ever come out of Y-Combinator.

The venture game itself has also had to change, along with these changes in scale and scope of the type of companies and founders funded. If you look at it across decades, the venture world moves more in fashions more than it does absolutes. When I moved here, in the dot-com era, it was the norm to replace a founder with a “grown up” more sales-oriented CEO. The pendulum has swung aggressively in the other direction: Founders are gods within the four walls of their companies.

“They have no respect for the fact that they are taking other people’s money—and it’s not my money, it’s pension and endowment money,” said one prominent VC who has struggled with the shift, but didn’t want to be identified for fear of getting a bad name with the new entrepreneur establishment. “The attitude is ‘You gave me the money now go away.’ Sorry, but that’s not my job. My job isn’t to run the company, but it’s also not to just go away.”

At some point this business became about funding a founder, not a company. This has coincided with three other theories of venture capital portfolio management that have become prevalent of late. The first is an obsession with a VC’s “social game”—to steal the parlance of reality TV. Since 75% of venturebacked startups are destined to fail, VCs today assume they’ll do less damage overall by writing off a bad performer than doing the hard work to fix it. Even if they oust an ineffective founder, a company may be too damaged to salvage, meantime, the VC has ruined his rep of being “entrepreneur friendly” for nothing.

The second theory is the new valuation math: Given basic liquidation preferences and soft landings at bigger Valley companies, the risk to losing all your money is somewhat protected. Likewise, companies like Facebook and Google have thrown traditional valuation math out the window too, caring only if someone might disrupt them in another ten years.

So the only thing anyone cares about is the upside. VCs—in this point in the cycle—are smart to worry less about erring on the side of paying up too much for a deal than erring on balking at a seemingly high valuation. Especially when the next day Mark Zuckerberg could rewrite every rule by paying $2 billion for a hardware company that doesn’t even have a product on the market. As Bill Gurley of Benchmark says, “You can only lose your money once” if you invest. If you don’t, you can effectively lose that would-be appreciation many times over.

Without assholeswe wouldn’t have relational databases, iPhones, or any other manner of innovations that have improved our daily lives.

Is it the mantra of a bubble? Maybe. But it’s the mantra you need to adhere to if you wanna get in any deals right now.

The third change that rules venture decision making is an acceptance that no one has any clue of what works.

Is Snapchat all sexting? Apparently not.

Is Yo even a thing? Maybe?

Is Secret morally bankrupt? Who the hell knows! Just write the damn check and let’s figure it out later!

The determiners of success in the Valley are no longer CIOs deciding on huge iron boxes that cost millions a pop. It’s not even whether geeky early adopters will like Twitter or FriendFeed more. It’s what teens around the world want to do on their phones. A hot mobile app has more in common with a movie premiere than a classic Silicon Valley tech company. And increasingly, VCs know they have no clue what’s a good idea and what’s a bad idea. Better to back all the apps showing “hockey stick growth” on college campuses. Any VC would be happy to write off a dozen LikeALittle’s for one Snapchat.

Why do you think Mark Zuckerberg has Instagram, Whatsapp and Facebook Messenger all operating as independent apps slugging it out with one another for supremacy on the same campus? He knows to some degree this is all a crap shoot. And an insanely binary one that can end with pennies on the dollar or a $19 billion exit in a few years.

Funding an asshole? Sure, OK. It may also break the stated venture capital playbook of investing in good people, but what is even left of that playbook these days?

The Sean Parker effect

Others pinpoint the trend to the release of “The Social Network” as a turning point in what was considered acceptable startup behavior. One of the reasons that the outrageously fictional film was concerning to Valley insiders is that it glorified a story that wasn’t true—and one dotted with crazy misogyny, backstabbing, and bad behavior. While Facebook’s founders and early team are hardly saints, the portrayal was wildly off and celebrated the “brogrammer” culture that has become so reviled.

At the time, VC Shervin Pishevar expressed concern that he heard young founders worshipping this kind of behavior. Ironically, he’s most known for his investment and close involvement with Uber, a company that would come to define the trend for many in the Valley.

For me, it all started with the resurgence of Sean Parker. I first met Parker when he was doing his press tour for the launch of Plaxo. A very early pre-Friendster prototype of the social network, Plaxo was seen as a ballsy bet by Sequoia’s Mike Moritz, because the mood had shifted heavily away from consumer Internet companies in the wake of the bust and Parker’s previous company, Napster, had no shortage of scandal.

The bullishness faded quickly. The next time I heard about Plaxo, Moritz (not exactly known as a nice guy himself) was running Parker out of the company and there was a full-court press to sully his reputation by characterizing him as a drug-addled, unreliable womanizer. When he resurfaced as Facebook’s president, the Valley still wasn’t paying much attention to consumers, and the move didn’t get a lot of press, nor did his departure at the time. But when he joined Peter Thiel’s venture firm Founders Fund, the Valley establishment went wild.

I was writing a profile on Parker for Fortune at the time, and it was one of the worst professional experiences of my career. Part of that was the frustration of spending that much time with Parker. While a genius and charismatic, he’s also known to be unreliable and manipulative. But far worse was the full-court press Fortune and I got from the Valley establishment to outright kill the story. I was told by some of the Valley’s biggest names that no good would come of it: That Parker was so toxic and so damaging that elevating him as a respectable VC would hurt the industry. Around the same time Sequoia actually pressured its LPs at an annual meeting not to invest in Founder’s Fund, because of Parker’s involvement.

Thiel—ever the contrarian—saw things more simply: Parker brought him Facebook, and when he got in personal trouble, he stepped down without a fight. Thiel hired him for two reasons: loyalty and the off chance that Parker may bring him another Facebook. Shit, even a half-Facebook would make the gamble worthwhile. I’ve always admired Thiel for such personal loyalty in the face of what was an ugly smear campaign—albeit one that wasn’t altogether false.

But something strange happened between Justin Timberlake playing Parker in a movie and the launch of Airtime: Almost all those investors who’d tried to convince me there was nothing redeeming about Parker started salivating to invest in Airtime. The narrative suddenly became that Parker had a “Midas Touch”—never mind his own companies had never had huge success, nor that he’d been ushered out of Facebook before it hit the big time. Literally nothing about his track record changed between the exact same people telling me I’d be blackballed in the Valley if I wrote a story giving Parker any credit for anything good and them writing him a huge check. The only thing that had changed was the Valley’s way of doing business.

When I asked people privately about this change of heart, they shrugged. He had, after all, discovered Facebook. He was a savant about the way the consumer Web works and what users want. It was worth the gamble that he could be right.

We all know what happened: Airtime flopped hard. Amid early struggles, there were conversations about whether or not Sand Hill Road should demand the money back. Many of the investment firms would have no part of such a plot. Their reluctance was due less to any great confidence that Airtime would find its footing and more to wariness and the memory of how Sequoia had previously been punished for pulling its support of Parker. It simply wasn’t worth getting a few million bucks back to risk the reputation as being “non-founder friendly” in today’s Silicon Valley.

It’s a sunk cost—move on and bet again.

In defense of the assholes…

The story of Sean Parker’s bizarre transformation in the eyes of VCs demonstrates how the venture game has changed. And frankly, those investors weren’t necessarily wrong to bet on him. This is a complex topic with no real “right” or “wrong.”

You have to consider what the job of a VC is. It’s not to give inner city kids a helping hand; it’s not to make mom-and-pop dreams a reality; it’s not to help nice guys. It’s to maximize returns and fund companies that have an outsized chance of creating billion-dollar plus outcomes in a decade or less.

There is a certain personality type that frequently builds these companies—a mix of outsized arrogance, steel-eyed determination, and even some element of delusion. Rational thinkers don’t usually think they can upend whole industries. People who get impacted by social pressure will be talked out of an idea long before it comes to fruition. And overly empathetic founders will struggle to make hard decisions and fire the people closest to them when they need to. If you don’t come into founding a startup as an asshole, frequently the journey can make you one.

Further, even assholes can have an outsized positive impact on the world. It’s hard to argue there’s anything positive in the case of Secret, but Uber certainly has done good. Thousands of drivers are making better incomes and are in control of their own businesses in ways they haven’t been before, and I believe Uber will reduce drunk driving as it grows and ripples through high schools and colleges. I’d happily prefund an Uber account for my kids in their teenage years instead of buying them a car.

These companies also create thousands of jobs, make thousands of people into millionaires, and provide high growth stocks that help increase pension and mutual fund wealth around the globe. Horrible people can actually do great things. At some point, doesn’t the good of an entire new market outweigh the bad of one person who got rich off of it?

This isn’t entirely new. Read any biography of Steve Jobs, Jim Clark, or Larry Ellison. They weren’t exactly the two-dimensional villains they are sometimes depicted as, but they weren’t what you’d describe as nice guys either. Clark—one of only two entrepreneurs in the history of the Valley to co-found three $1 billion plus exits—was said to make underlings shake nervously in his presence. Ellison’s mantra was reportedly, “It’s not enough that I win, everyone else must lose.”

There’s also the inherent subjectivity what makes someone an asshole. In working on this story, several people named people like Mark Zuckerberg or Mark Pincus or even Nextdoor’s Nirav Tolia as “assholes.” I know all three decently well, and while hardcharging, competitive entrepreneurs who’ve made mistakes or run roughshod over others at times, I wouldn’t necessarily put them in quite the same camp as a David Byttow or a Travis Kalanick.

But I say that as an industry insider who knows most of these people, their friends, investors and in some cases their families. And I surely have my own personal biases. Whether we boycott an organization or not as consumers shouldn’t hinge on everyone getting to know them. On the other hand, it’s all too easy to get into witchhunt territory, particularly when it comes to something like parsing college emails.

Let’s face it: The press (or, occasionally, filmmakers like Aaron Sorkin) frequently shapes and distorts these public figures into heroes or villains that will drive page views (or box office sales). One of the great things about Silicon Valley, to me, is that your track record speaks louder than Gawker or whatever Internet mob-du-jour is after you this week. These things, if inaccurate, typically don’t stick, and don’t have a huge impact beyond emotional distress.

Case in point: Bustle. Bryan Goldberg wrote a somewhat hamfisted story about the launch of the women’s site that got wildly twisted and distorted by an Internet mob. It even caused Google Ventures to agree to let Goldberg buy out their share rather than keep supporting him—a bit rich given the investment in Secret.

But most of Bustle’s readers weren’t in that microcosm, and didn’t read the subsequent New Yorker profile on Goldberg which referenced it. They just love the site. Fast-forward to August when Salon was asking how a “bro” managed to build a women’s site. Well, for one thing, because he was never the person the media depicted. He wasn’t trying to “mansplain” anything to anyone. He saw a hole in the market and hired incredibly smart female editors to build a great product while he does what he does best: build a media business around it. The outrage over Bustle has turned from “mansplaining” to “how dare he not be the stereotype we tried to make him into?”

Ultimately—my disgust at some of the behavior in the Valley aside—I don’t want to live in a world where some preachy Internet mob is the arbiter of whether someone is an asshole or not, taking people’s jobs and the potential for a great company. That said, there have to be times where it crosses a line.

The disturbing thing about many of the recent cases of bad behavior is how much misogyny keeps popping up, just as women are starting to make significant inroads into the startup world. When it comes to race, for instance, some behavior simply isn’t acceptable no matter when you wrote it, whether you were running a company at the time, or what the context was.

Donald Sterling was forced to sell an NBA team based on remarks. Paula Deen lost a TV show. Their context didn’t matter. So how is it cool that people so blithely chalk up the misogynist emails of Spiegel or the allegations against Arrington as simply boys-being-boys?

“No Longer a Gentleman’s Game”

It’s a cliché in business to talk about the twin forces of greed and fear driving everything but when it comes to venture capital, it’s slightly different. It’s less greed and fear than greed and regret. And mostly, regret.

It’s a subtle difference. This was another thing Vishria shared with me as talked about beginning his career as a VC. When I asked if he went into venture capital because he wanted something “easier” than starting another company he said—like many VCs— that venture is a harder job than it gets credit for. But he added that it was a “different kind of stress.”

“It’s not as acute, but it’s longlived,” he said. “The best VCs, when you talk to them, they feel regret. I notice this time and time again, and it’s only the best ones. They all are thinking about the ones they missed. ‘We passed on that’ or ‘We didn’t hustle hard enough.’ Every one of them has a story. It’s really eye-opening when you are thinking about going into this field.”

He’s right. It’s a standard question we ask VCs on stage: What is the big company you passed on? What was the one that got away? And the problem is the truly big regrets can’t be forgotten because they seem to get bigger and bigger. Passing on Google seemed embarrassing in 2000. It made you want to punch yourself in 2005. And today as Google’s market cap hovers at $392.5 billion it’s horrifying. Ditto Facebook. David Sze of Greylock was mocked for investing at a “crazy” $500 million valuation. Today it’s valued at $201.45 billion. The regrets of the Valley continually mock you and laugh in your face. And even one homerun can make a fund. Some 95% of the returns in venture capital come from 5% of the deals. Few people’s jobs are that binary.

Venture capital simply moves too fast, has too much competition with too little inefficiency and friction, and the stakes are too binary for this to remain the gentleman’s game it once was. But sacrificed in that very real reality of what is necessary to keep the lifeblood of this industry pumping are two sad realities. One is that founders sometimes need to be kicked out of their companies—even Steve Jobs did for himself and Apple and Pixar to ultimately reach their full potential. When companies get big enough, it shouldn’t just be about the founders. It should be about the teams, the users, the customers, and even some service paid to the product and idea itself. Should all of those forces be sacrificed to one person’s ego and the fear that they could damage an investor’s street cred?

The other sad reality is the continual erosion of what Silicon Valley—as a place—stands for, if anything. This used to be a place of misfits and changing the world. Even the legendary assholes had a cause beyond themselves and checks and balances on their board. It just may take another economic collapse to get back to that.

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Art by Brad Jonas for Pando