October is loaded with milestones for me: Pumpkin Spice Season, Mean Girls Day, and my brother Daniel's birthday on October 5th. (Happy Birthday, Daniel). His birthday is also the day Steve Jobs passed away—12 years now. Three days later that year in 2011, Oakland Raiders owner Al Davis died at the age of 82. Mr. Davis isn’t viewed as an influential giant as the Apple co-founder, but he in his own right was an innovator—Commitment to Excellence.

Deadspin posted a satirical yet brilliant article about the deaths of these two giants. For Mr. Davis, they updated the announcement of Steve Jobs’ death, struckthrough text and replaced it with sentiments about Al Davis. It was intentionally lazy; showing people that the legacy of both men had similar arcs and innovators in their own right.

I'm a lifelong Raiders fan, and in my mind, they're still in California. Many people now think of Al Davis as the crazy owner who drafted JaMarcus Russell. However, Mr. Davis was a huge reason the NFL even existed today as a result of the merger of the AFL. He was an innovator in the vertical offense. Did you also know he was the first owner to hire a black head coach (Art Shell), Latino (Tom Flores), and woman exec (Amy Trask)? He had a commitment to diversity, but didn't talk a lot about it—just did it.

Here’s what John Madden said about Al Davis in Madden’s Hall of Fame speech induction:

“If somebody wants a chance, Al Davis is the greatest at giving them a chance. There are a lot of people that talk about things and never do anything. Al doesn’t talk at all … He just does it.”

Apple and the Raiders are two of the companies I admire the most. Losing both founders in the same week in 2011 was very tough for me in my 20s. This week, I’m reflecting on what makes The Bay Area special to me. I’m not convincing you need to move here, or that it’s the only place innovation occurs. Physical locations all have a unique presence and history which makes them unique. Let’s look at what makes the Bay Area unique and reflect on my time there in the past (and now present).

Innovation in the Bay Area

One of my favorite drives in the world is up and down the West Coast, especially the Pacific Coast Highway. Compared to other areas in the United States, there isn’t much when you drive through. It’s chill, slow, and a bit sleepy. Within that, hidden from the world, there are areas of innovation and new ideas happening—very stealthy from the rest of the world. Legendary 49ers Coach Bill Walsh describes this in his book, "The Score Takes Care of Itself.” He hated how the East Coast media called his offense, “The West Coast Offense.” The West of the United States is very young compared to the East Coast and our Eurocentric history. Being hidden became an advantage.

My first exposure to Silicon Valley was when I was still living in the Pacific Northwest. It was from the television film, "Pirates of the Silicon Valley"; a biographical drama about Steve Jobs and Bill Gates. I very much enjoy that show to this day and found it hilarious that Steve Jobs had Noah Wyle (who played Jobs) come on stage at Macworld in 1999. Even people outside of tech are familiar with the story of Apple starting in a garage in Los Altos. However, throughout the valley and bay, there were other innovations occuring.

When visiting the Presidio, the statue of Master Yoda from Star Wars may feel out of place at the corner near the Palace of Fine Arts. George Lucas, the creator of Star Wars, attended the renowned USC film school but is a Modesto native. Instead of staying in Los Angeles, Lucas set up shop in the Bay Area.

Across the East Bay is Pixar, a computer graphics division of Lucas Films purchased by Steve Jobs, who was fired from his job as CEO of Apple. As we know the story, Pixar went on to be a breakthrough film studio. Two of my favorite Pixar films of time are The Incredibles and Ratatouille, both directed by Brad Bird. Prior to the two successes, Bird directed The Iron Giant and a long-time creative consultant on The Simpsons. In Adam Grant’s WorkLife podcast, "The creative power of misfits," Bird talks a lot about how frustrated people can disrupt the status quo. He talks about how he wasn’t a good fit at Disney and Pixar was the right environment for him to have breakthroughs.

There is something about the Bay Area of Northern California that lets you work in the shroud of the fog. Steve Jobs famously said, “It's better to be a pirate than join the navy,” and the Bay Area is full of them—quite literally when the Raiders were in Oakland.

What makes the Bay Area unique

History

Every region and city has its own history that makes it unique. When I go to the Computer History Museum in Mountain View, I can't be in awe of what came before me. History is biased and contextual, but it's key to be a student of it; allowing you to not repeat the same mistakes and innovate.

Community

From a group of Dominican Friars in Rockridge to my brunch crew which makes up about 60% Apple employees, you find niche communities in the Bay Area. You do have to try hard to find it, but once you do, I assure you it's wonderful. The Bay Area has always been a place where new ideas are formed through communities.

Tech density

While other cities have tech-enabled industries, the Bay Area is tech-enabled tech—a huge volume of it. Honestly, it feels cringe a lot of the time, but there are nuggets of what makes it special. There are very few places where big bets are made that you can explore.

The things that make you cringe also is a signal of uniqueness. The moment I sat down at the coffee shop I was introduced to the sounds of conversation of two people talking about Personal CRM (an idea I love by the way). If you work in tech, there is no place that goes as deep as here.

Reflecting on my San Francisco eras

As my friend Jem said, "I've lived three San Francisco’s," which is a brilliant way to track the number of times people have proclaimed the city dead. In the 2000s, I reconnected with my aunt, a software engineer who lived in the Bay Area. These visits sparked a motivation for me to move here. However, I moved to Brooklyn, NY, first.

San Francisco 1: iOS and startups (Early 2010s)

The first era was as a frequent visitor from New York. I was living in Brooklyn at the time running a product studio with my friend. At the time, we were building all sorts of web apps during the Ruby on Rails/Heroku golden age. When Steve Jobs passed away, we saw it as a rallying cry to make something great. We decided to focus the majority of our attention on building iOS apps. It turned out the timing of the iPhone was a big hit and companies were thinking about their mobile strategy. I found myself coming to San Francisco multiple times a month including the annual pilgrimage to Apple's World Wide Developer Conference (WWDC). One of the highlights was designing a product that was accepted to the Jason Calacanis’ LAUNCH Festival in 2013.

This era unlocked my network in Silicon Valley. Many of these people I met became future clients, friends, and contemporaries in my career.

San Francisco 2: One Medical (Late 2010s)

This era meant finally moving to San Francisco. I moved back to Seattle after nearly five incredible years in New York. I wrapped up at Black Pixel and was working as a contractor, with one of my clients being One Medical. Kimber Lockhart, One Medical’s CTO at the time, convinced me to join full-time. My first apartment was a rent-controlled unit in Lower Pacific Heights (I should have kept it). Prior to One Medical, the longest place I’ve worked at a company was two years. During this San Francisco era, I stayed at One Medical for four years.

I learned in this area the value of playing the long game at a company. I saw One Medical change each year as we experienced hyper-growth. I found multiple mentors during my time here.

San Francisco 3: Replit and the AI boom (Early 2020s)

I moved to Santa Monica in March of 2020, a week right before the pandemic. The beginning of the 2020s was remote and in Southern California, eventually moving to Palm Springs (where we still reside part-time). After nearly four years at Webflow, my plan was to take a sabbatical, which lasted three weeks. After advising with Replit for a bit, I loved the people, product, and purpose so much that I joined full-time. I came up to San Francisco frequently and was reminded of the energy it had in my first era during the mobile paradigm shift—now with AI. We decided to get a place in San Francisco and be residents again.

I’m in the midst of this era and can’t tell you what the unlock is yet. Ask me in a few years.

Come through

I’ve struggled with the transactional nature of the Bay Area in the last hundred years, but it’s part of the history. I’m reminded of this while watching Season 3 of Warrior. It can feel like someone always has an agenda with you or hanging out with friends means booking time on calend.ly. I assure you, that once you can parse through the noise, you can find authentic communities and connections. The City is not perfect; far from it. There is a discrepancy of wealth with various levels of safety. There is a lot that needs to be fixed. It can feel transactional living in this city.

There is the saying, "Sort-Term Skeptic, Long-Term Optimist" and that's how I feel about the San Francisco Bay Area. However, if you get out of the bubble, you'll find a lot of great reasons to love it. Many people don't stay in the San Francisco Bay Area forever. Even the people who moved to Miami often come back and have fond memories of the San Francisco Bay Area. It can be transactional but a transformative experience. A new generation will come through, and The City will rise once again.

Think Different. Just Win Baby.

Week 40 recap

• Congrats to Webflow on an incredible Webflow Conf and rebrand people actually love

• Thank you so much Michael Riddering (Ridd) for inviting me to the Deep Dives podcast! I had such a wonderful conversation and you can get notified here: https://www.dive.club/deep-dives

• Congrats to Joey Banks on an incredible run at Webflow. Excited to see what you do next

• New role at Replit

Hype links

Collection of what I read and related to this week's post

• Showboat: The Life of Kobe Bryant → Started reading this

• Former Raiders CEO Amy Trask shares life-defining memory of the late Al Davis

• AI Engineer Summit → If you’re attending, let me know as I’ll be there!

Job opportunities

We're hiring at Replit

• Software Engineer, Platform - OS

• AI Engineer

• Software Engineer, Front End AI Infrastructure

• Software Engineer, Frontend Infrastructure (Workspace/IDE)

• Product Engineer

• Product Engineer (Web Infrastructure)

• Product Manager, AI

Startup opportunities

• Ditto—a single source of truth for your product copy, is hiring a Product Designer, Product Marketer, and Product Engineer

• Designer Fund’s job board

• Design Leadership job board by Design Dept