What I learned in my year after our IPO
It was raining in Seattle. There was almost a warm familiarity to the cold, night haze that scythed through the buildings in South Lake Union — a reminder of growing up in Seattle and embracing it like an uncomfortable but reliable roommate throughout my childhood.
But this wasn’t my childhood. The rain wasn’t pouring through thick fir or alderwood trees in Wedgewood; it was whipping through skyscrapers in an area of Seattle that didn’t exist when I was growing up there. Rather than watching the twinkling spires of downtown through rainy haze from North Seattle, I was here in its center — warmed by a cup of coffee that cost almost two months worth of allowance when I last lived here.
This city was familiar. But it’s not the same city I grew up in. And I’m not that person anymore.
It’s been over a year since HashiCorp went public. As the first product manager recruited into the company, I was blessed to have the experience of a lifetime in joining and early stage startup and being a strategic part of its story through to becoming a “big” company.
Following our IPO, my life changed. So did the world. Due to war and inflation, the macroeconomic landscape has changed. So too has tech, as the seemingly endless fountain of money from venture capital has started to ebb and started to change the culture from quixotic evergreen to something darker and more reminiscent of the dour environment I graduated into just over a decade ago.
Life seems synecdoche with rain and the world. So much has felt familiar, and in the last year I’ve been blessed to return to hobbies and pursuits I gave up earlier in life to pursue education and work. But this is not the same world. This isn’t the same tech industry. And I’m not the same person.
One principal difference between this last chapter of my life and this new one is writing. I spent a good chunk of my twenties and early thirties here, writing about my experiences and reflections in tech. When I joined HashiCorp my pace of writing slowed down significantly — largely because until early 2019 I spent most of my effort on writing most of the documentation on Vault and regular blogs and PR for the company.
While I briefly played with opening a substack to talk just about technology, investing time in myself this last year has made realize that isn’t really me. I don’t write to be some thought leader or influencer; I write because it’s therapeutic and it’s a medium to tell stories I think should be told.
This isn’t to throw shade on people trying to be tech influencers by the way. Far from it; I think it’s cool that we live in a time where you can focus on being a storyteller for our industry and sustain yourself off of it. But while I like telling stories, I’m in tech to build technology. For me to try to be some kind of thought leader isn’t authentic to why I’m here.
And honestly, I think thought leadership is a kind of dangerous path to walk if you’re dealing with some of the deeper questions on purpose and insecurity that I’m trying to figure out right now through more healthy means.
So as much as I’m annoyed that Medium decided to focus their editor only on the web presence, I want to continue this story here. It’s really captures what I want to do: tell stories I think should be told in a more authentic-to-me kind of way.
To that end, I want to talk about two major challenges I’ve been navigating since we went public: re-discovering my purpose and fighting imposter syndrome and insecurity.
One of the biggest challenges I’ve faced when HashiCorp went public was around identity.
My role in the company is nowhere near as significant as our co-founders’ or senior leadership team. But it’s not insignificant nor is it invisible. Being the first PM recruited in the company means a lot of my perspective and work on establishing how products like Vault approach strategy and product development are now codified in our cultural DNA and processes/procedures.
And throughout our company’s growth I was a visible representative of both Vault and product management at HashiCorp. There’s still a few years of our blogs and YouTube channel where I was the one evangelizing our work during releases — and years longer after that from conferences both at our company and within the industry where I acted as our primary representative for how we look(ed) at security.
Candidly, I never thought much about this. For the better portion of the last decade I’ve been just focused on execution and strategy: how do we get Vault bigger? Who do we hire? Are the assumptions we had to get to this level of scale still valid, and where do we go next?
The IPO forced me to step back and realize that with the success of our product that I had a public role in that success. With that public role came visibility and a kind of pseudo-augustness that was similar to how I saw other investors treat successful founders when I was still on the investment side in venture capital.
I’m not sure how I feel about all of that. I grew up in an environment where I wasn’t necessarily encouraged to “sell” my achievements, and overall I’m far more comfortable letting my work speak for itself rather than me sell my role in it.
I also think tech radically undersells the reality of how technology is made — in teams. In tech we have a habit of equating the success of a major product with a single person or small set of personae. I think we do this because from a narrative/storytelling point of view it’s more attractive: it’s easier to understand the human dimensions and drama of building a company or successful product when we focus on a set of “characters” rather than the truth that such development was the work of a larger, complex team.
This tendency to not focus on the role of a team is one of the reasons why I tried to explicitly call out the achievements and work of the early Vault team during our IPO. As we grew and narratives were written about the company’s evolution, I didn’t want us to lose the authenticity of how we actually got here.
But teams change. People grow, evolve in their careers, and move on. While we’ve been blessed at HashiCorp that most of our early team members on Vault are still here (and mostly still within HashiCorp’s Secure Organization), that “magical” time of us being a small handful of people fighting the market incumbents in a narrative fitting some kind of guerilla war doesn’t exist anymore.
The magic still exists. But it’s different now.
The dark path of thought leadership
Regardless of how I feel about that, there are lots of opportunities to stoke your own ego and drown yourself in allure with that narrative of success. Just as SV tech culture is fascinated with “Hollywoodizing” successful tech startup stories, so too is it filled with opportunities to capitalize off one’s role in a successful story for personal gain.
As HashiCorp’s role in infrastructure technology’s role became apparent, so too did the opportunity for a lot of us in visible roles to represent ourselves as everything that tech culture loves to venerate: thought leaders and visionaries. I’m genuinely glad that almost nobody I’ve worked with has gone down the path of getting hooked into doing that.
But I’d be lying if I said there also isn’t an allure. If you ever go to a tech mixer where people know what you did, it’s something else to feel that sense of glory of “I was the person who did X.” I’d be lying if I said the dopamine hit from that wasn’t intoxicating.
In fact it’s intoxicating enough that I’ve seen people do pretty shitty things to keep the high up. I’ve seen founders completely misrepresent either their stories or the stories of their company’s success to ride that high. I’ve seen former operator VCs retcon their role in a notable exit to be more strategic than it was, and non-operator VCs embelish/lie about how impactful they were in a company’ success in order to “extend their roll” as long as humanly possible.
I chose a different path: therapy. It’s not because I’m smarter or stronger than any of these people. It’s because I knew I would probably do the exact same thing if I didn’t square away myself and make sure I didn’t try to self-medicate my own insecurities and imposter syndrome with the dopamine of pretending I was the Tony Stark-esque image that tech culture likes to pretend exists.
It’s important for me to be authentic. It’s important for me to know that while I played a strategic role in a successful tech company that I’m proud of, that I did so because I was blessed to be on an amazing team of people. It’s okay that I have a lot of conflicting feelings about being simultaneously proud and humbled by my role in that team’s success, and that it’s going to take me time to figure out how to feel about my role in that story and where I go next.
Too often the dopamine rush of false glory is used in our industry to pretend these issues- namely insecurity, imposter syndrome, and other forms of unhappiness or ennui — don’t exist. It’s surprisingly easy to go on Twitter, LinkedIn, or even in person and get hits of dopamine from people praising you wax poetic about your perceptions on business and life if you’re blessed to have been part of a successful exit.
I don’t want to do that. I want to deal with my problems. I’d rather be honest about my journey to figure out how I feel about all of this. And I’d rather earnestly and honestly figure out one of the biggest ones: what do I do next?
So, what now?
My friend Adam Altman is a fountain of profound quotes. Ten years ago he said something at his birthday when someone asked him about his future plans: time doesn’t move in five year increments.
There’s strong urge in the narrative of high tech success to “jump” from project to project. Effectively chasing that success becomes more important than building tech. The narrative seems to dictate that just like we should arbitrarily chunk time, we should similar arbitrarily chunk our careers to fit the mold.
That…isn’t me. And the reality is that I still love working on our security products here at HashiCorp. Even as Vault has become the largest (and arguably first) secrets management product in history, it still has major dragons to slay on its horizon. Boundary is just entering the market, and with it comes a similar opportunity to change how enterprise computing thinks about a fundamental part of security. There’s still so much fun work to do.
I do know that whenever my time comes to an end at HashiCorp, I’ll be taking a break. I’ve been incredibly blessed with my experiences at the company — even beyond being in a great position at a great time, Vault was essentially what I dreamed about building as a teenage script kiddy wanting to hack the planet for a living. Whether my time comes in two years or ten, it’ll be the end of more than just a chapter of my life.
I don’t know exactly what I’d do in my break. But I know I’d use that time to center myself and figure out what other dreams I’d like to go chase. There’s more dreams out there: more things to figure out, more adventures to go on, more worlds to explore.
Turing said it best: we can only see a short distance ahead, but we can see plenty there that needs to be done.
Here, there, and thereafter, I’m excited to continue exploring what else needs to be done and how I can help.