SJSU from the top floor of the library

Ten years ago I woke up to the sound of birds chirping.

Joe West Hall, the monolith that I lived in my freshman year at SJSU, glaringly lacked air conditioning. To avoid the South Bay’s typical (and infamous) late summer dry heat, I would leave my windows open at night and hope the wind would circulate the air in the room.

Turning over in my bed and wiping the sleep out of my eyes, I saw a grey and black finch hopping on the murder hole-esque cement overhang outside my window. After a few seconds staring at me with its beady black eyes, it flew off into an impossibly blue sky.

A quick shower and change and I found myself walking out of Joe West into the heart of SJSU’s campus. It was still a few days before school was going to start, but crowds of students and their families were starting to show up. As I tried to fish my headphones and my zune out of my pocket, I took it all in: the vibrant colors, the excitement of thousands of new college students embarking on their new lives, and me — in there in the middle of it with them underneath a deep, electric blue sky.

The final scene of Garden State (2004) with Frou Frou’s Let Go

The song that played once my Zune spun up came from last night. I had gone out the night before with the school’s curiously fratty CS Club.

Without a fake or enough money / game to talk my way into a much seedier version of San Jose’s bar scene, I was forced to spend most of the evening back at our friend Josh’s dorm. Those of us that couldn’t make it to the bars ended up watching Garden State, trying to find meaning in the movie through the haze that came with the gauntlet of our friend’s pregame.

Right before Josh, Butler, and Ramos crashed through his front door to force a few more shots down our throats, the room was abnormally silent. Those of us left watched the end of the movie as Zach Braff and Natalie Portman admitted to each other that they had no idea what they were doing, and that while they were scared about the future they were also excited about what possibilities may lay in it.

Then came the music. The soaring, impressionist-esque violin. The steady accelerating drum and bass beat. Frou Frou’s Let Go was a song that expertly matched the terrified-excitement of the twenty somethings on screen who decided to throw themselves headlong into a future they never expected or even wanted. In the silence of Josh’s living room it hit hard, and later that night I downloaded the song and loaded it on my little blue Zune.

Listening to Let Go in the center of the color and chaos of students moving in, I felt a profound sense of empathy with the movie’s message. Here I was at a school I never thought I’d go to, with new friends I never thought I’d meet, about to go on and adventure whose end I couldn’t see.

The only thing I really knew was that it was right. That even though it was scary, that everything was going to be okay.

I was exactly where I was meant to be, underneath an electric blue sky that stretched deep into the horizon.

I came to San Jose State sort of on a whim. Right after high school, I found myself lost without the seemingly crusade-like purpose that most of my high achieving friends who ended up at Berkeley or on the East Coast. I was lost.

I went to CSUMB instead to study Applied Computing and Mathematics. And while the school was great and my roommate was one of my best friends from high school, the material wasn’t challenging. I didn’t feel like I was getting the seismic life change that my other friends back raved about on Facebook.

So I decided to switch schools. Transferring from a CSU to a UC was an extremely difficult proposition (California has two separate state school systems), but transferring within the CSUs was easy enough. Sitting on the beach in Monterey watching the sun dip into the ocean, I tried to figure out how I could measure where I wanted to go and could reasonably get into.

That night I found the SJSU Computer Science Club’s website. The page was a nightmare Drupal forum that had been apparently hacked recently. But it was also filled with excited chatter from the school’s students.

OGCS circa 2006

I had never met Josh, or Ramos, or Butler. But I could read their stories and started to get an idea of just how ridiculous they were. Butler had an operation to remove a tumor, and once he got out of the hospital they decided to throw a celebratory party.

Apparently it was a rager and everyone was wasted. Butler’s mom was confused about what turned out to be a messy college party.

This didn’t sound like a computer science club. This sounded like a super dirty frat.

And then came the math. Johan talking about how his TopCoder solution made Andy[1]s (we all had nicknames — some of us who shared the same first names were simply given indices in the array of our first name) look “like it was autogenerated in Eclipse.” They openly talked about advanced math and algorithms with incredible fluency, mixing in jokes about the Wu-Tang Clan lyrics into discussions on how to implement things Min-Cost Max Flow.

This whole “Straight out of Compton” take on computer science thing was a running joke in the club. SJSU at the time was a haven for incredibly sharp competitive programmers. They loved CS for CS’ sake, but matched against schools like Stanford and Cal head-on in TopCoder and the ACM they always felt a little outgunned and outspent in resources. So the club embraced the suck, and thrived by cultivating an image of being (as they called it) “Original Gangsta Computer Science” majors — or “OGCS” for short.

I was infatuated with their stories. I wanted to be a part of this. I applied for transfer, was accepted, and later moved schools before the fall semester in 2006.

Over the course of my four years at SJSU, I went on adventures with these OGCS. I was the youngest in their group, nicknamed Andy[2] because I was the third Andrew to join the CS Club (this is a CS joke).

The lessons I learned, the adventures I went on, and most of all the people I went on those adventure with shaped me. They pushed me to go from someone who struggled with math to exhaust SJSU’s undergrad stats and probability curricula. They turned me from a burn out hacker wannabe to someone who could balance 3 jobs, take 7 classes (typically students would take half that), and force his first job out of college to let him into actual infosec.

Most importantly, they taught me to enjoy challenges. SJSU was never going to be a school whose prestige was going to take us anywhere. We had to learn how to enjoy the challenge of facing down innumerable things in our path and rise to the top. I learned to face my fears and personal iniquities in the company of people who never let me give up on myself.

SJSU was a risky, crazy adventure that seemed like an insane bet as it was predicated solely on my brief experience with a handful of people online. And I learned that sometimes that’s exactly what you need.

And it turned out to be just what I needed.

Ten years later, and I found myself similarly lost.

2016 has been a year of incredible personal change. After a seismic shift in my life and my plans for my future, I found myself lost in wondering where I was going and who I wanted to become.

My career became the bedrock of what I had left that seemed stable, but I struggled to find the passion and fire that drove me to succeed early on as a young associate in VC. Much of it had assuredly been spent righting the ship personally so to speak, but it was clear that something had also changed in me. My experiences left me someone else — someone I didn’t recognize from the Brooks Brothers-wearing, finance-fascinated twenty something from the year before.

I was different now. I needed to recognize that, and in doing so find something that made whoever I had started to become happy and deeply fulfilled.

Sunset at the secret beach near CSUMB

So I did what I did the last time I felt lost: I jumped in my car and drove down the coast. Parking at CSUMB, I hiked over an abandoned bridge and jumped a fence to get to the familiar beach I sat on as a freshman in college. I watched the sun dip into the ocean, blasted Above and Beyond’s On A Good Day from my iPhone, and watched day turn into night as the music mixed with the sounds of the waves crashing on the shore.

In that cacophony, I asked myself a serious question: when was I last really happy? When was I last in a period of my life where I felt personally fulfilled and excited about the future?

And I realized, much as I did ten years prior, that the happiest time in my life was at SJSU. As a poor college student who didn’t know where he was going but was surrounded by people who inspired him, I found my path in being infatuated with the amazing things you could do with technology and math.

But perhaps even more than the technology itself, it was really the environment of people like the OGCS who similarly were focused only on the substance of computer science and figuring out fun things to do with it. SJSU was great because the OGCS were great.

And I wanted that back in my life.

Unfortunately, that’s not really how venture capital works. As one transits from associate to partner, VC becomes more of a solo game than anything else. Sure, you work on a team with other people in your firm (and I had an amazing firm who I loved working with every day). But to get the most out of your LP’s money, VCs have to specialize and do lots of individual work on their own.

I wanted to build. I wanted to focus on technology first. Most of all, I wanted to do all of this with a tight knit group of people who loved doing these things and put the substance of this before all else.

I decided I wanted to go back into product. I just needed to figure out where.

In 2012, when I was just starting out as an associate at GGV Capital, I met a young UW CS grad named Mitchell. Mitchell had just shipped a software suite called Vagrant that dramatically improved the workflow around building up a technology infrastructure to run applications.

The value of Vagrant was hard to explain to other VCs and non-tech types who had never written code. But for those of us who had it was absolutely amazing. Being able to script up the description of an infrastructure — and then to have that infrastructure appear almost out of thin air — was absolutely fucking amazing.

I met Mitchell first with the idea of sourcing his new company, Hashicorp. But what was supposed to be a thirty minute meeting where my well-rehearsed lines about VC would be customized to the setting, I found myself completely throwing everything away and just nerding out. Mitchell’s insights on infrastructure blew me away, and we spent a full hour beyond our time at Sightglass Coffee talking about where he saw the world going.

Mitchell wasn’t the only one. I similarly had another experience a few days later with Armon, Mitchell’s co-founder and friend from school. Like Mitchell I met Armon in the context of being a VC. And like Mitchell, that all went out the window as we began nerding out and I learned more about how he saw the world.

Hashicorp over the last four years has become something of a juggernaught in infrastructure. Their perception of the world, as written in projects like Vagrant, Vault, and Terraform, has wonderfully predicted the world of code-driven infrastructure that has surged forth in other places like AWS Lambda. The Hashicorp team was almost oracular in their work, and even from afar you could tell how well things were going just watching the outstanding adoption that flocked onto their open source products.

When I got back from Monterey, Armon and Mitchell were two people on the top of my list that I wanted to see. I told Armon a little bit about my story and how I wanted to go back and build things, and to my surprise he smiled and mentioned that he needed someone to work on a cryptography product at the company.

Over coffee I once again found myself floored with what Hashicorp was doing. The project Armon was talking about, Vault, had basically made the hardest and most arcane parts of cryptography simple and easy to deploy for developers. As someone who worked in cryptography in school and in my first job at NetApp, it was astounding to see what he and their team had built.

“Think about it. But if you’re interested, I’d love to plug you into our guys here. We need a product manager who’s excited about this and the varying challenges we’re going to face as the enterprise starts using this. This seems like something that’s your jam.”

I went home after that experience and did just that. Sitting under a warm, late summer night’s sky watching planes fly over Foster City, I thought about Vault and Hashicorp as a whole.

I was excited by them. But in deep thought, I realized that what made me so excited about them wasn’t just the technology. It was the people. Armon, Mitchell, and the whole Hashicorp team that I had crossed paths with in the past were amazing. They reminded me a lot like the people I worked with in college — passionate technophiles who liked substance and technology first and honestly didn’t put much time into glitzier aspects of Silicon Valley.

So I did what I had done ten years ago: I went home, jumped on my computer, and applied to join them.

Last week I woke up to the sound of a bird chirping.

I don’t leave my window open here in Chinatown, as there’s a landing just outside and it’s cold enough here in San Francisco as is. But I could still hear the bird, a small finch who flitted around the area outside my window momentarily before taking off.

A quick shower and change and I found myself walking out of our street into the heart of San Francisco. Chinatown during the morning is a cacophony of sound and color — a din so loud that both bled through my music no matter how high the volume.

Nevertheless, I pulled my iPhone out of my pocket and slipped in my earbuds. As I wondered what song to play, I saw the Bay Bridge sparkle in front of my under a crystalline, impossibly blue sky.

I smiled, astonished at the sense of deja vu. Here I was in a life I never thought I’d live, with a team I never knew I’d work with, about to go on and adventure whose end I couldn’t see.

The only thing I really knew was that it was right. I was exactly where I was meant to be, underneath an electric blue sky that stretched deep into the horizon.

I played Let Go.

And I walked to work.

Principal PM for Cryptography and Security Products @HashiCorp. Formerly Defense/NatSec & Crypto @NetApp, VC @GGVCapital + @AmplifyPartners

Principal PM for Cryptography and Security Products @HashiCorp. Formerly Defense/NatSec & Crypto @NetApp, VC @GGVCapital + @AmplifyPartners