Why Silicon Valley CEOs always think they're the good guy | Ladders

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This is why Silicon Valley CEOs always think they’re the good guy

A charismatic tech startup founder selling his product as a “unicorn,” or potential billion-dollar company. Male bosses crossing the lines with their female subordinates. Venture capitalists about to give millions in funding to a company on incomplete information. An intrepid journalist receiving a salacious tip about a founder’s misconduct.

We could be discussing any number of Silicon Valley scandals in recent history, but in fact, this is the fictional world of “Startup,” a newly released book written by BuzzFeed News journalist Doree Shafrir. The book is a so-real-it-hurts examination of the new Gilded Age of technology that we live in.

If the book reads like a behind-the-scenes documentary of the tech startup industry — and it does — it’s because Shafrir interviewed around a dozen founders and VCs off the record to get the hubris and charm in these founders just right.

In “Startup,” this worldview manifests in regular-guy-turned-millionaire Mack McAllister, the CEO of a mindfulness app who needs to close his next round of funding before his company runs out of money. Despite these high business stakes, he cannot stop himself from contacting his former flame and current employee Isabel. When you believe you’re making the world a better place, like McAllister does, anyone you want and anything in your way can be justified.

“I think that there are very few people who see themselves as bad actors, and that was something that I thought was important especially with Mack. He seems himself as a force for good. Genuinely,” Shafrir said.

On why startups keep getting themselves into trouble

Although her book was written before Uber CEO’s Travis Kalanick’s ousting, the book is prescient about the career-ending, self-defeating impulses built into the DNA of both fictional and real tech CEOs.

Shafrir wrote the book as sexual harassment allegations were coming to light in the startup industry. While Shafrir was writing her novel, Ellen Pao was taking her former employer to court on gender discrimination and retaliation claims and Whitney Wolfe’s screenshotted texts were being used in her sexual harassment lawsuit against Tinder.

These lawsuits show a toxic pattern of workplace behavior that has kept repeating itself into the present day. “I think that you have this potent and sometimes-toxic combination of people with not a lot of experience and a lot of money and this idea that they’re kind of invincible combining. When people’s power goes unchecked, it can have disastrous consequences,” Shafrir said. “As we saw at Uber, Susan Fowler brought her allegations to HR and they didn’t do anything about them. I think all of those things are potent at startups because startups are new, they’re growing so fast and these things are kind of afterthoughts.”

On how technology is changing the way we communicate at work

The biggest scandal in the novel happens over an intimate Snapchat message made public through a screenshot.

It’s a cautionary tale into how our modern workplace communications—those one-on-one messages and private group chats—can lull us into a false sense of security. As Shafrir noted, “everything is on the record, everything is permanent, I think people forget that. Chat can feel informal, but it’s there, it’s saved, people can also screenshot it. It’s not private.”

For better or worse, social media encourages professional and personal lines to blur so you can see your co-workers’ Twitter feeds and comment on their Instagram pages at work and at home.

“Most people I know do not have private Twitter accounts, they combine personal and professional on social media in the same way that they do in real life. We know our co-workers much more intimately than we did in the past,” Shafrir said. “Can you imagine Don Draper on Twitter? That was just not the way people engaged with their co-workers in the past. You left them at five o’ clock. Maybe once in a while you went to dinner with your partner and their partner, but it wasn’t the same as it is now.”

On being the lone older employee in a sea of millennials

The perks of startup culture are satirized by the employees who feel like outsiders in it. One of the book’s older protagonists, 36-year-old Sabrina Blum, feels alienated by younger co-workers at her startup asking her to go to pole dancing classes together.

In a startup that demands more of her personal time and enforces her happiness, Blum makes biting critiques about the startup world’s work-play balance, comparing her workplace to a Henry Ford company: “You were now supposed to feel like your work was your everything: where you got your paycheck, yes, but also where you got fed and where you found your social circle. Everything had started bleeding into everything else.”

For some of the older characters in the book, this generational difference causes them to act snobby towards their younger peers.

Shafrir’s advice for real-life older employees at startups is to choose open-mindedness over judgment: “I work in an office where I’m probably ten years older than a lot of my co-workers. I feel like I learn from them and I try not to place a value judgment on their experiences or their world views, and I think it’s important to keep that in mind, and to be open-minded. But it’s hard. I think those of us who came of age in an era where people in their twenties were assistants or where there’s a very specific path—especially in media—it can be confusing.”

On the future of startups

“Startup” documents the pressure points in an industry that has yet to wake up to the lived realities of the most vulnerable people in it. It’s a time capsule of a world where executive power goes unchecked, too often at the expense of women. Will the book still feel relevant ten years down the line?

When asked, Shafrir said, “I obviously think a lot of the technology will change and evolve. My utopian vision is that people will pick this up and be like, ‘oh yeah, remember when sexual harassment was such a big deal in tech?’ because we’ve moved past it and we’ve figured it out. That would be my dream. If not, I hope that people pick it up and are like, this is a good representation of what it was like in 2016-2017 in New York City tech.”