The Millennial SaaS-era Retrospective: Part 4
Technology has always had two edges. A tool for farming or fishing becomes a weapon of war. And institutions, even in their best forms, always have to reckon with individual human fallibility.
Twitter had never been particularly concerned with acting as an arbiter of truth. They saw themselves primarily as an engagement and commentary platform, never a news one. Yet as journalists and media personalities swarmed onto Twitter to promote their ideas, the line between truth, opinion, and outright lies became blurry. A tweet that activated excitement and imagination could spread virally, worming its way into the public consciousness far faster than it could be debunked.
Donald Trump had used Twitter to spread conspiracy theories about Barack Obama from the 2012 presidential cycle onward. Despite repeated debunking by professional news outlets, he charged forward, increasingly setting his own narrative independent from the establishment voices. In 2015, he announced his candidacy for president on Twitter. He was never taken seriously... until he started winning state primary elections. He would win the Republican primary with minimal backing from the party in DC.
At the same time, Democratic party outsider Bernie Sanders was launching his own rogue candidacy for the Democratic nomination, rivaling yet another Hillary Clinton bid. Party elites did not see the same opportunity in Sanders that they saw in Obama. They mobilized "superdelegates" in individual states to override the popular vote in key primaries, pushing a showdown between Clinton and Trump that was assumed to result in a resounding Democratic victory. They miscalculated.
The Obama campaign had run a tightly organized campaign using homegrown digital infrastructure to win the election. The Trump campaign just used what was already there. They blasted tweets and Facebook posts and let advocates self-organize on Reddit. They stoked institutional mistrust left over from the 2008 financial crisis (and the Obama administration's failure to punish it) to drive a shock victory for the unexpected campaign. Hope and change turned into a bad joke.
Millennials, perhaps more than any other generation, were left aghast. After years of pouring technological know-how and donations into the Democratic party, they watched institutional elites fail to read the room. Millennials saw in Trump the spirit of everything that they stood against. His gaudy rich man persona reminded him of the banking culture that had cost them career opportunities eight years prior. His misogynistic comments toward women and cruel comments toward individuals with disabilities offended years of effort toward social equality. If someone could be an "anti-Obama," he was it. And he was proud of it.
Less than 30 days after Donald Trump's inauguration, the tech world was rocked by a blog post by Uber engineer Susan Fowler, documenting multiple instances of sexual harassment at the company and the tactics used to silence her after she raised her issues through company channels. The fallout from Fowler's blog post would take down multiple Uber executives, including company founder Travis Kalanick.
Not long after, Millennial-founded Theranos would file for bankruptcy protection after a multi-billion dollar valuation. The company, a mainstay on the cover of Forbes, had been committing outright fraud for nearly its entire existence. The self-imagined heir to Steve Jobs turned out to be nothing more than a con artist.
And despite all the warning signs against rampant mania, investors couldn't stop themselves from chasing returns with Adam Neumann's WeWork. Neumann himself walked away with hundreds of millions of dollars. Investors got nothing.
Hell, even AirBNBs were losing their quirky cool. What had started as a novel way to travel was now turning into a corporately operated cartel of private equity-backed houseowners. No one was having fun any more. But the party had to keep going on.
We moved fast and we broke things. Lots of things. We didn't just tear down Chesterton's Fence - we lit a bonfire with it. We ignored the lessons of Sarbanes-Oxley by just staying private for ages and avoiding corporate governance. Homeless encampments that would have been immediately apparent as Hoovervilles started popping up in cities across the country, and our Doordash orders just drove right past them.
Uber shrugged off the Kalanick debacle and IPO'd in 2019, making a whole lot of people rich. So did Slack, Pinterest, Lyft, Fiverr, and a stack of other platforms founded in the boom cycle after 2004. Most Millennials could point to at least one friend, or a friend of a friend, who'd become a small millionaire after joining the right tech company in 2011. We were happy for them, and we were a little jealous. We'd been operating at a manic tear for a decade now, and we too wanted a break.
The trend was pointing toward a repeat of the dotcom cycle. Investors were taking their payoffs from IPOs and turning them into strange crypto plays, extolling how web3 would change the future. An entire cottage industry sprung up around crypto assets, moving past the payment novelty that had been a small undercurrent of finance toward a weird "metaverse" that would encompass our digital lives. Perhaps, in another timeline, everyone just got caught up in a wave of irrational exuberance and eventually paid the piper.
But no one ever expects a global pandemic.