The Millennial SaaS-era Retrospective: Part 2
soundtrack: Ke$ha, "TiK ToK"
Every generation has its coming of age moments. For Millennials, it was a tale of three cities. New York, DC, and San Francisco all played a role more than any others - even if you didn't live in a single one, the events that happened in each were burned into the generational culture.
City I: New York
There was no better place to watch the crash of 2008 than an investment bank trading floor. That's where I was. Front row seat. Watching my future change as my prospective banking employer rescinded my offer amidst doubts that the company would even be around.
New York goes in cycles. You can watch The Wolf of Wall Street, The Bonfire of the Vanities, Seinfeld, and The Big Short in a cycle as if it's some circular morality play about money and ridiculous people that has gone on for time immemorial. 2008 was just another part of the cycle. People got greedy and that greed crashed the economy.
The effect of the crash would be profound on Millennials, a generation encouraged to take on massive amounts of student debt with the promise that it would be paid off in short order. Many with liberal arts degrees from top-notch schools hit unexpected stress when their consulting jobs were cancelled in the wake of the housing crash. They would see fifty- and sixty-year-old financial and government leaders trying to explain things on the television, and they would quickly begin to conclude that those old institutions just weren't working as promised. That institutional failure would shape the Millennial psyche for the rest of their lives.
New York still pulled people in. Always has, always will. But for a few critical years in the Millennial psyche, it lost its luster. Too much institutional cruft. Too many doors closed. If you wanted to make it - if your student loans said you needed to make it - then you were drawn to look elsewhere.
City II: Washington, DC
"Above all, I will never forget who this victory truly belongs to – it belongs to you. I was never the likeliest candidate for this office." - Barack Obama, after a surprise victory in the Iowa caucus in 2008
Heading into 2008, Hillary Clinton was the presumed Democratic nominee in a continuation of a dynastic cycle of Bushes and Clintons since 1980. Hillary was the safe choice. Barack Obama was perceived to be a "rising star" with his speech at the 2004 Democratic convention, though it was generally expected that he would wait his turn until Hillary had gone through the cycle. Voters had other ideas.
Barack Obama campaigned on a need for the country and the government to change, and that resonated with Millennial voters in their first big election cycle. And perhaps even more so - the campaign operated in a way that encouraged Millennials. The campaign didn't just run ads on television and radio, they promoted themselves on social media platforms that Millennials had invented. The voter files were updated with any information that could be gleaned about a voter before someone went knocking on doors.
When Obama went to Washington, he brought the strength of that campaign into the White House to change the way the government worked. Open APIs and open data became the norm. Digital government professionals jumped in to bring stodgy government websites into the 21st century. Legacy contracting processes were put under the microscope. Obama's primary health care initiative failed out of the gate due to legacy technology, and it was these digital government employees who brought it back to life. Things were going to be different, and they were going to be different with software.
What started as a technology initiative now roped in young people of all stripes. Political science and liberal arts majors suddenly saw an opportunity to get their ideas into the world, using the Internet in ways that they never had before. Young journalists now had megaphones that had previously been reserved for old-school writers. Software allowed collaboration, coordination, and broadcast at speeds never before seen. The humanities found their way into the Github repo. They wouldn't stay in DC for long.
City III: San Francisco
By the time the financial crisis started ramping up in 2007, the software industry had shaken off the malaise of the dotcom crisis and was hiring again. Google's IPO and Facebook's massive funding opened the door for consumer-focused software, Salesforce's IPO did the same for enterprise tech, and Apple was hitting home runs with every new product announcement. Traditional industries all faltered with the financial crisis. The Bay Area acted as if it never even happened.
It was easy to miss the early signs of the cultural transformation of San Francisco. The peninsula had always attracted large office parks, while the city had maintained the hippie-cool atmosphere of its 1960s heyday. Then Salesforce launched on Telegraph Hill, and Twitter followed in the Mid-Market neighborhood. The old tradeoff - sleepy suburban campus perks versus big-city culture and atmosphere - was gone. The job and the scene were the same place.
Ambitious college grads couldn't find work at the traditional consulting firms or banks, so why not head out west for the energy? Obama campaign alums found themselves in early-stage startups. Wall Street refugees took coding bootcamps. If you didn't know anyone at all, that was just fine - just get out there.
Just show up. Launch something. Sleep on a couch. Apply to YC. Try whatever works and fail fast - at worst, you'll head home with a ton of LinkedIn connections and a stack of VC phone numbers.
As the Federal Reserve pushed interest rates down to zero to stimulate the financial system, tech began making its own gambles. Funding became increasingly easier, especially with an established network or sound pedigree. People tried new things. User growth was all that mattered - you could figure out the business later. Tech hadn't moved this fast or been this fun since the 1990s, and Millennials were getting their first taste as actors after watching as kids from the sidelines.
New York was a center of collapse. DC inspired those who still believed in institutions and wanted to make them better.
But San Francisco was where the culture was going. DC would ultimately stall, victim of the politics that had allowed the crash to happen in the first place. New York would go through another cycle. San Francisco was going to define the decade.
The nerds were charismatic, they were driven - and they were about to start winning.
The journey continues in Part 3.