Bad Apple*

On the slings and arrows of cancellation

*Note: The title is a self-deprecating reference to a ‘bad apple’ that falls off the tree, not a reference to any company.

If you want to criticize a religion, write a book.

-Apple’s app store guidelines

It is admittedly somewhat ironic to be bemoaning the horrors of my cancellation via my relaunched Substack, whose generous advance grants me the enviable freedom to pontificate widely and wildly for an entire year.

But I assure you, I’m canceled. Or at least, I think I am. Like frontier forts in 19th-century Afghanistan where the limits of the British Empire were defined by the range of a .303 rifle, your scope of cancellation is defined by how far your antagonists can fire their Tweeted missiles that declare you no longer worthy of human attention.

It’s possible I’m still within range. 

For those who somehow missed the story, my Apple drama was well documented by Matt Taibbi, and you can listen to my take on it on the Sam Harris podcast.

The sin?1 

Having published, five years ago, a bestselling and critically-acclaimed memoir titled Chaos Monkeys about my time inside a young Facebook. While mostly focused on the business of startups and digital advertising, the book includes several racy and impolitic passages that might seem excessive and offensive to some readers, even within the “gonzo” tone that this jittery, first-time author tried so hard to emulate. 

Literary juvenilia is one thing. A person’s values in life as they are expressed in the workplace is another. What I wrote in 2016 in a certain literary style is very different from the actual non-literary me in a professional setting in 2021.

If writers and artists are to have real-world lives during or after their periods of creation, treating what’s obviously a piece of stylized non-fiction as reflecting their non-artistic life is a path to mediocrity—in both culture and in business. The most heinous political ideologies of the 20th-century felt that art should always and everywhere exist purely in support of the political, and the results were not very pretty, politically or artistically.  

My experience is only the latest in a series of dramas that have convulsed Silicon Valley. In the run-up to its IPO this April, the cryptocurrency exchange Coinbase disallowed political conversations at the workplace. Employees unwilling to work under these strictures were offered a generous severance package, and roughly 5% of employees took it. The company seems to have escaped further criticism.

Less successful was Basecamp, a collaboration-software company, whose two celebrity founders are very vocal about their progressive politics. The whole thing blew up in their faces, with a solid third of their employees opting to leave the company, including senior executives who Tweeted their dissatisfaction to a swirl of attention. 

Stuck somewhere in between was the company fittingly called ‘Snowflake’, whose brash, hard-charging (non-American) CEO uttered perhaps the supreme corporate heresy of our era: Diversity goals should not trump the demands of merit-based hiring in a company focused on results.


The most heinous political ideologies of the 20th-century felt that art should always and everywhere serve the political, and the results were not very pretty, politically or artistically.


In a statement that read like the script of a hostage video, Frank Slootman soon recanted his heresy and apologized for having questioned the corporate catechism. What’s particularly humiliating is that Slootman had made the (valid) point that many CEOs were privately in agreement with him, but didn’t dare speak out. Just imagine those private group-message threads and the awkwardness now.

In those confessionals of Silicon Valley life—private Signal groups where everyone is sworn to a secrecy enforced by the mutually-assured destruction of impolitic candor—venture capitalists and CEOs confide that every company is now agonizing over which way to break on the issue: Coinbase-style defiance and voluntary severance? Or Google-like caving to a small but burning-hot swarm of employees? 

They’re also debating strategies to avoid the woke trap altogether: How do we hire employees who won’t start internal woke crusades and waste everyone’s time? I just want to make this go away: what do I do? Can you just look at this shit? (Slack screenshot attached.)

(My suggestion: Hire mostly immigrants, who still entertain the quaint notion that getting a job means actually showing up and doing it, rather than mounting Slack crusades to fill the spiritual hole at the core of their lives.)


If people getting paid over six-figures at a two-trillion-dollar company refuse to come into work at their spectacular billion-dollar headquarters where every luxury is provided, then those employees have lost all grasp on reality and have no right to petition anyone about anything.


The pandemic-era Zoom-ified workplace is now simply an extension of the online mud-wrestling rings of Twitter and Facebook. The same polarized politics, interminable wrangling, performative moralizing, and gleeful dog-piling are all there: it’s called Slack and masquerades as work. Just as social-media titans Mark Zuckerberg and Jack Dorsey have been press-ganged by public opinion into becoming editors-in-chief of the public sphere, every boss in corporate America will be forced to concoct a content-moderation policy for their internal communications.

Matters have reached such an absurd point that the nerdy, bespectacled chief executive of Shopify, an ecommerce site that is Canada’s largest company by market capitalization, had to issue a sternly-worded memo to his employees who seemed to think for-profit corporations are something between a family and an activist group. “Shopify, like any other for-profit company, is not a family. The very idea is preposterous,” explained Tobias Lütke. “Shopify is a team, not a family... Shopify is also not the government. We cannot solve every societal problem here,” he said. “We also can't take care of all your needs.”

Trendy management philosophy's love for “bringing your whole self to work,” and somehow conjoining the multitude of an individual's identities—cultural, artistic, religious, political, sexual—with one’s professional persona is a deranged recipe for endless mayhem. Nobody actually brings their “whole self” to work; if you spoke to your colleagues as you do your partner after sex or your friends after the fifth pint, you’d be sacked from any job even faster than I was.

What’s perhaps most preposterous is that these reality checks need to be forcibly repeated to working adults in some of the cushiest and most prestigious companies in the world. In an absurd follow-on to my situation, not only did Apple employees petition their company to issue a statement about the Israel/Palestine situation—as if having a foreign policy position were germane to a public tech company—but they also petitioned to not have to go back to work inside an office.

If people getting paid over six-figures at a two-trillion-dollar company refuse to come into work at the spectacular billion-dollar headquarters where every luxury is provided, then those employees have lost all grasp on reality and have no right to petition anyone about anything.

This unholy trinity—the quasi-religion of wokeness, corporate ingestion of the corrosive social-media machinery and a deluded view of working life—is what bedevils the newest generation of American companies. Once you let the mob accrue influence internally, short of taking a hard stand managerially as Coinbase did, you have no option but concede to their demands and offer the mob the object of their desire (or rage) on a plate. Every company who goes down this path will be limping from crisis to crisis forever (as Google is).


Silicon Valley once served as the last refuge of renegades and dropouts, wild-eyed prophets and daring pioneers, the sort of place that would take someone like Steve Jobs in. Nowadays, he and people like him wouldn’t last a day inside the companies they created.


Silicon Valley once served as the last refuge of renegades and dropouts, wild-eyed prophets and daring pioneers, the sort of place that would take someone like Steve Jobs in. Nowadays, he and people like him wouldn’t last a day inside the companies they created. On the flip side, if the hard-charging figures that created these companies were still around—people like Andy Grove, who titled his memoir “Only The Paranoid Survive”—one imagines they’d have very little patience for the petitioners. As with so many things in American life, senior management is shambling feebly around the frayed institutions that greater and past generations built. If there’s any subversion (or principles) left in Silicon Valley, it’s thanks to startups whose founders possess both the nerve and social capital to take a stand about why their companies exist.

When Apple launched the Macintosh computer in 1984, they famously ran a Super Bowl ad that featured a solitary figure flinging a sledgehammer into a Big-Brother-like face spewing propaganda at the huddled ranks of some drab dystopia. The tech titans nowadays resemble more and more the haranguing figure on the screen than the colorful rebel going against the established order. Whether it be hiring policy or free speech, Silicon Valley has to decide whether it becomes what it once vowed to destroy.

1

It might amuse Chaos Monkeys readers to know that I always thought I’d get canceled for the book. The first chapters were written in Berlin in early 2015, where I’d moved assuming my life would be utterly over in the US tech scene. But I thought my cancellation (before that was even a term) would be over my flagrant violation of Silicon Valley’s code of silence, plus my withering mockery of Silicon Valley’s elephantine greed and self-regard, not some offhand joke about the SF dating scene.