When To Jump off a $500 Million Rocket Ship

Christopher Chen
8 min readMay 11, 2021

Most advice about early career growth tends to sound like: “Look for the rocket ship, get on board, and hang on tight!”

Two months shy of my 2-year mark (and a Patagonia jacket), I closed my laptop instead feeling like I had jumped right out of the emergency exit, just as we had reached the stratosphere. I had just closed my fingerprint-greased, sweat-stained, and overtly dust-sexual hunk of a laptop for the last time as an engineer at Vanta.

(Some of) Vanta at Spark Social… sometime around August 2019. I’m in the back w/ a white hat!

Excited. Sad. Crazy. Happy. Insane in the membrane? Some heavy feeling draped over me as my chin dipped down towards my pajamas — my WFH bottoms of choice. Some heavy feeling draped over me, that I didn’t quite have a word for. The emotions sat closer to saudade. Not that I had saudade, but more that I felt some emotion deep, confusing, conflicting, freeing, and still at the same time gut-clenching, an emotion that exists outside our collective English vocabulary.

At the same time, when I think about our past 2 years together, I’d say that Vanta brought out who I am, and where I need to go.

In December 2018, when I had just graduated from college, I had never thought in a million years that I’d be without a job. I had so much privilege: I came from a family that valued education intensely and gave me the resources to walk the yellow-brick road of career success. I was a mostly A’s student, I’d punched the instant resume green light at Facebook the summer before, and on top of it all, I wanted it.

I wanted to know that people could turn passions into careers, and daydreams into reality. I wanted to believe that, someday, I could be a part of helping others find the things they’d love and pursue for the rest of their lives.

So in that moment, I was ready to ride off into the post-grad sunset having my new life laid out at the end of the red carpet — a Boeing 767 away from joining the next startup set to change the world. I’d be proud to tell my family and friends. I’d put myself as close as possible to people who were dreaming big and succeeding, so I could learn how to do it myself.

Instead of practicing my glamorous model-walk to showcase my monotone hoodies, tees, Birks, and Timbs, I found myself spending more time watching anime and doom-scrolling Youtube than ever before. I had been excited to jumpstart my post-grad career working for a friend’s 3-person startup that I had been working with during my entire last semester in school. Instead, what I found was that I had turned down all my offers, stopped all my new grad recruiting, only to end up hearing that when it came down to joining full-time, there wasn’t a good fit.

I didn’t have the job. I didn’t have a job.

What I had instead was shards of animated characters, dissonant tunes with offbeat rhythms, and my daydreams of what could have been all mixed together, slipping away from my fingers.

The first thing Vanta gave me was hope. Vanta taught me that I was still worth the dreams that I had in mind.

I remember the first time I got in touch with Erik and Vanta. Past graduation, and past the new grad recruiting season, were there really still promising small startups looking to take a chance on me? I was skeptical. I didn’t want to settle for the Googles and Amazons — some place that would hire and forget about me.

Even their cold outreach — the best I’ve seen to this day! Thanks for asking me about my music :)

By the first phone screen, I could already tell that there was a different sort of energy and care there. Just to get to their office, Erik put up with hours of airline customer support to reschedule so many last minute airplane mishaps. By the time I had finished my onsite, I was glowing. They gave me so much energy and personal time to make me feel welcome, excited, intellectually curious, and ultimately that even if everything went to shit, I’d not regret spending my time there. Who knew that putting together a bookmarking service could be that fun? Christina had a China reading list — I’ve never met an uninteresting person with a China reading list. Above all of that, what I saw was a team of people with a method to create something out of nothing, and proof that on this path, androids would dream securely of electric sheep.

When I first started at Vanta, 2 years already seemed like forever. In Silicon Valley, 2 years really is eternity. As my first full-time job, I’d never really had a fixed, full-time role for longer than 3 months (unless you count my stint teaching at Kumon). I remember one of my coworkers early on asking if I’d ever imagine myself at Vanta in two years.

“Absolutely not!” I’d exclaimed as we hopped in the cranky elevator at the top of 57 Post St.

“If I were still at Vanta in 2 years, that would mean that I would have given up on growing. I’d have given up on my own dreams.”

And for most of the first year I was at Vanta — I felt like I was dreaming. I was interviewing people outside of engineering three months on the job. I was responsible for getting Vanta our own SOC 2 attestation (finally) another two months later. I was constantly reaching for a seat at the table, to make Vanta better than the Vanta before me could have ever imagined.

Saying something important about blockchain and AI and edge computing

How do we build, grow, and evolve a strong company culture? How do we set expectations for how we work together best, and teach that to others? I knew what I wanted to do, and I never knew how to do it. I was so deep in discomfort that I’d exclaim to all my friends and family where I worked, what I did, and that I loved my job.

And I got thrown in the Wall Street Journal along the way!

I couldn’t believe my eyes: I was helping change how the world thinks about security, I was learning by doing, and spent my time surrounded by the most formidable people.

But one day when I opened my eyes, I woke up realizing that I didn’t have it all.

There’s so much inherent good that society places on learning — as long as you’re learning, you’re golden. There are people, communities, and systems that make you believe that learning is even the end goal. For some people, that works great. I’ve internalized “learning is good” so much that as long as I had been learning something at least tangentially related to my general aspirations, I’d feel content day-to-day.

But what comes after learning?

When I take a step back and think about my privilege and luck, and mix that with a bit of ego, I think I have an incredible opportunity to do something that goes past just learning. I have an opportunity to do a lot of good for others in the world. I have an opportunity to do good in a way that’s unique to how I see the world, what I care about, and for the people I care about.

After I took a step back, I saw that instead of learning the best way for me to realize what I want to see in the world, I was learning the best way for Vanta to succeed in the world. These two paths — they felt so tightly knit in my newly graduated mind — were coming apart. I needed to reset my GPS navigation back to how I could best grow people and their passions. So what other choice did I have?

It didn’t matter that we had already left ground.

It didn’t matter that we had already crossed 30 miles above the 9th floor of 57 Post St.

It didn’t matter that Vanta had given me everything after I thought that I’d have to settle for nothing.

On March 26th, 2021 at 4:14 PM, I ran straight to the exit hatch, hollered my loudest exclamations of appreciation and goodbye, and hurled myself out the door.

So what are dreams made of, if not jet fuel melting steel beams?

If not SaaS companies, retention metrics, and customer acquisition costs?

If not Javascript bundle sizes, Typescript compile times, and Donut meetings over Zoom?

For me, it’s helping more people discover what they love, share what they love, and support themselves through their passions. I’m off to be uncomfortable, learn what I’m so incredibly wrong about, and readjust and get back to chasing my dreams.

I’m currently building Passionfruit to do that. It’s Pinterest for people who care about curating for others. Share music, books, and more in a place designed to highlight your taste, and find other curators you’ll love along the way.

I’ll be Building in Public to the extent in which it’s not distracting. Feel free to follow me here on Medium for longer narrative posts every 2 weeks, and Twitter for more regular updates.

And finally, how can you help?

Do you know any curators or aspiring curators — music, books, videos, movies, games, industry news, or otherwise? Message me on Twitter or shoot me an email.

The literal door!

Shoutouts to my whole Vanta team across all time — without them, I wouldn’t have seen and made the magic I did. Erik, Christina, all the Kevins, Neil, Ellen, Lukas, Tom, Matt, Robbie, Kelsey, Eli, Ansh… The list goes on forever! Always wishing you the best. Also they’re recruiting!



Christopher Chen

1. Tech. Maybe it's stockholm syndrome, but coding is fun. 2. People. What makes you tick? 3. China + East Asia. What freakin' cool place.