I’m a software engineer from Cupertino, CA. I’ve been working in fintech for the last 8 years and most recently built and led the engineering team for Capital, a banking and fundraising app for founders.
I recently moved back to the Bay Area after 6 years in New York City and one year in San Diego, CA. I wanted to make this a bit more personal than previous versions of my website, so here goes...
I tend to get sucked into hobbies that are technically deep and require patience and risk management. My current obsession is tracking my 2022 Subaru BRZ and I’m competing in a local time attack series called 86 Drive Challenge.
Previous obsessions of mine have included: shipwreck diving in the Atlantic and trad rock climbing (frequenting the Gunks in upstate New York and Joshua Tree). Yes, I wasn’t kidding about risk management, physics, and a long attention span.
I was lucky to grow up in the technology center of the universe, in 1990s Silicon Valley. You couldn’t swing a cat without coming into contact with the tech industry.
My family drove past the HP campus (now Apple Park) to get to swim practice. I learned how to touch type on computers donated by Apple, in my elementary school computer lab. I went to the same high school as Steve Jobs and Woz, driving past 1 Infinite Loop on the way to school each day. I remember seeing the 6-story tall Think Different banner on the back of the Apple Headquarters from 280 and thinking—wow, this is where the most exciting things on the planet are happening.
I had an overwhelming sense of pride and excitement going to CompUSA with my dad to pick up a Bondi-Blue, first-gen iMac. (My family’s first computer was a rather unspectacular Macintosh Quadra, but I still loved playing The Busy World of Richard Scarry on it.) The other nice thing about living in the center of the universe was the default timezone on all Apple products was correct, right out of the box (IYKYK).
I always loved making things with my hands, starting with Lincoln Logs and Legos as a kid. I was fortunate to go to schools with funding for programs focused on developing tactile skills. I took 3 years of woodworking classes and 2 years of metals classes in junior high school. In high school, I took an electronics class and a film photography class, then started a photography club. The teacher who sponsored the photography club ended up recruiting me to join the yearbook team as the design editor in my senior year. I also taught myself how to edit video and how to build websites by reverse engineering other sites, including Apple.com. I remember figuring out how they made the glossy buttons on the Apple site by displaying regions from a single image (i.e. sprites) and it blew my mind.
After graduating from high school, I had a major spinal surgery, and decided to defer going to a 4-year school to give me more time to recover. I ended up going to community college at De Anza and Foothill College and it ended up being a great decision, which afforded me the luxury of more intimate relationships with professors and more flexibility to continue following interests unrelated to my major.
I took photography courses, some with an art history focus and others more practical, involving lots of time in darkrooms and photography studios. I learned about canonical art photographers that I love, like Hiroshi Sugimoto and William Eggleston.
In addition to some freelance photography work, I also worked a sales job at Wolf Camera in Mountain View, CA, where I quickly became one of the top salespeople in the region, largely by listening to what people wanted to achieve with their photography, rather than just trying to move one of the popular units.
After transferring to UCLA, I continued to explore photography, but also got increasingly interested in filmmaking. I ended up doing a minor in film and worked on a handful of graduate student film productions as a camera operator and as a grip.
Despite this interest in visual arts, my actual major was English literature, focusing on literary criticism. At the time, I believed I’d go on to graduate school to study something practical. But by the time I graduated, all the work I’d done outside of school (including many freelance web development gigs not previously mentioned) had prepared me to be able to get a job straight away.
My first full-time role was as a contract designer, working at Apple. I worked on a project called Textbooks for iPad. Specifically, I was on a team of production designers responsible for migrating paper textbooks to a brand new digital format. Partially from my experience building similar design systems for the high school yearbook, I quickly realized the templates we were using were not well-built. Every production designer working on the project would have slower velocity and less consistent results unless the templates were improved. So I pitched that project to the team and was given the go-ahead to rebuild the templates themselves, so the whole team could move faster with fewer errors.
By the end of the term of the contract, I was offered a full-time role directly working on the Apple team. While that was interesting, I had received another opportunity, which was more aligned with the ways I wanted to grow. So, I joined Google to work on a team as a hybrid designer/developer, building marketing and other static sites. There I was able to take more formal classes on CS concepts I’d missed out on in my non-traditional education.
Next, I transferred to the Android Design Team as an Interaction Designer and then finally assumed a new role as a UX Prototyper, again combining my experience in design as well as building software. In this role, I developed high fidelity interactive prototypes that ran on Android devices and which were used to validate designs for Android, Material Design, and Google Play.
Working on this 100-person design team was an amazing experience. One thing I learned in particular is that having an opinion is easy, but being able to articulate and defend that opinion in a dispassionate way is what allows you to change minds and get things done. One of the extracurricular achievements I made was getting a device orientation lock on Android. Simple though it sounds, there were reasons why it was believed this was not a good idea and I had to convince the Head of Design to reverse his previous decision.
I also enjoyed letting Regina Dugan (former head of DARPA) borrow my Noogler hat on our first day when Sergey insisted she wear one, being called Googley, playing roller hockey with employee #6, and being able to ride around inside the Android office in roller blades.
I left Google in somewhat unusual fashion, since I was really enjoying my time there. I decided to leave with my unofficial mentor, who was ready to do something different after working for years on Android and before that on WebOS at Palm. I realized I was learning so much from him that, no matter what we did, if I was working with him, it would be worth it.
We started a company called Canopy, which is a social layer built on top of Amazon—allowing people to discover products with great design. Building a company and a product from scratch was a new challenge and an exciting jump into the unknown. Technically, it gave me an opportunity to own the whole stack and be involved in making decisions from nothing. While we didn’t achieve all we wanted to with Canopy, it was a great segue into the next startups I joined.
In between Canopy and joining a new company, I had an opportunity to explore again and worked on a short-term contract with Uber, in person at Uber in San Francisco. I developed a prototype of their next generation Rider Experience app, which was designed by a former coworker of mine from the Android Design Team. The prototype was demo’d directly to the executive team including Travis and would go on to be released publicly once I’d left. I was also able to race Uber employees around the Uber office on ripsticks, in a scene which could have been straight out of Silicon Valley.
I joined Cadre as the first IC software engineer. It was a relief to go from CEO, engineer, and designer to just be able to focus on my craft. Like at Google, I had the benefit of great mentorship at Cadre as well. What I’m most proud of from my time at Cadre is the team I was able to work with, which was one of the most talented teams I’ve worked with. And, because I was there from the early days, most of that team I interviewed directly and many I managed.
While I had management experience from Canopy, I got more formal management experience at Cadre. I also got to observe a handful of different engineering leaders and see what they did well and what their gaps were.
Also carrying on the theme of wheeled transport inside an office, while we were expanding our NYC office space in the Puck Building, a handful of engineers conducted a time trial on an electric scooter in the gutted office.
At Party Round, which was later renamed Capital, I had an opportunity to compound a lot of the knowledge I’d gained at Cadre, while building the kind of products I wish I’d had at Canopy. We started with a fundraising tool with integrated funds flow built on a corporate bank account. Then, we took that foundation and started offering corporate bank accounts as the primary product.
For me, it was also an opportunity to build another startup from ground-up, but this time do it on top of even more experience. I chose a tech stack that would allow us to be productive in the beginning, but also avoid a lot of the pitfalls I’d seen as we scaled Cadre. For example, at one point at Cadre, build times were becoming a barrier to productivity and our infra team estimated that it would take 9 months of effort to move us to a better build tool. By building on top of tools like Bazel from day 1, we could get the benefit of incremental builds and separation of concerns from day 1.
Like Cadre, the team we’ve been able to build at Capital has also been a highlight. I’m lucky to work with insanely bright and motivated people.
Thanks for reading. New chapters coming soon,
Brian Armstrong