Cupertino, Then and Now

You may know it now as the default weather location on every iPhone shipped, but when I was growing up, Cupertino was a sleepy little town. These days it feels like every city in the bay has a similar growth story due to the tech boom.

As a millennial, I was the last generation to know life before the internet — and in the 1990s/2000s, my childhood in Cupertino was far different from my peers’ on the east coast or midwest. For one, it skewed decidedly Asian, and I grew up listening to shopkeepers talk to me in Mandarin. We also had the benefit of many parents working in tech. I grew up wanting an Apple clamshell laptop, then an iPod, then a black Macbook. My dad would travel to Taiwan/China often, and bring back the hottest Sony walkman or newest Japanese CD. It was pretty normal among my friend group, and it wasn’t until I went to college that I discovered most kids played outdoors and developed social skills while I was tinkering and reading books.

Now as I sit sipping my Philz (Jacobs, Phil’s way) at this new phenomenon called Cupertino Main Street, it’s jarring just how much Cupertino has grown up in the past 10 years. It’s jarring to think about how it may change even more in the next 10. So here’s a list I put together for fun.

10 years ago, Cupertino was pretty uncool (to my teenage self).

• Apple was a niche product beloved by designers (and computer nerds like me).
• The office buildings in the area were from an era of cubicles and corporate soulessness — work was work, not a lifestyle.
• Cupertino High School wasn’t considered a good school. We sent less than 5 kids to the Ivy Leagues, and ~15 kids my year were accepted to UC Berkeley.
• We all had our “Top 8” on Myspace and the smart kids had figured out how to embed their favorite song on their profile pages.
• There was one chat app, and it was called AOL Instant Messenger.
• After years of complaining, I had finally received my first cell phone — a Nokia that could play Snake.
• The original version of streaming music was awesome, and it was called Napster.
• There were 3 boba shops. The most popular one was Fantasia.
• Santana Row had just been built and people thought it was stuck up.
• The coolest coffeeshop around was Starbucks.

Today, Cupertino is one of the hottest cities in the Bay Area.

• Apple is building a spaceship headquarters down the street from my house, designed to house 1500 employees.
• The offices here have huge windows, free lunch and ping pong tables. Work is your life is your work is your life.
• Cupertino High School sends 20+ kids to Ivy League schools. 40 kids were accepted to UC Berkeley last year. Monta Vista and Lynbrook send even more.
• Myspace is dead.
• There are a million ways to reach someone — Facebook Messenger, Whatsapp, Snapchat, Wechat, and more. Pick your poison.
• I basically have a small computer that I carry around in my pocket. Not sure it can play Snake though.
• There are 10+ boba shops within a 10 mile radius, and the most popular one is called Monster Boba.
• Santana Row has a Warby Parker and a Tesla store. There were 3+ VR exhibits scattered throughout the local mall (compared to 0 in Denver). I walked through the Target parking lot and counted at least 4 Teslas. I drove around Cupertino and counted 4 more.
• And I’m currently sitting at the second (!!!) Philz location in Cupertino — a beautiful thing, with wall-to-wall glass windows and Apple laptops galore scattered around in front of various techies.

I know I’m waxing pretty nostalgic right now, but the change our generation has experienced has been incredible. These are just a few of the things off the top of my head — there are probably more that I’m missing.

PSA: In general, cities that experience this kind of economic growth have two choices: they can artificially limit housing/commercial development in an attempt to keep people out, or they can embrace it and grow their city. This was a hot topic in 2016, with a number of related initiatives proposed on city ballots (including Cupertino’s). For the most part Cupertino has leaned towards decisions of growth, but I think we have yet to really run into the infrastructure limits of this city.