Where I've Been or How Did I Get Here

Posted: 4/30/2020

I graduated from university in the summer of 2011. It was a strange time for me personally as well as for our society, having been worn thin by the housing crisis. I had majored in International Relations, essentially the study of global political history, and of sovereign nations and how they interact with one another. A truly fascinating field of study, but I was wholly unprepared for the reality of life as a graduate. I applied to over 100 jobs in the summer that followed graduation, in various fields, ranging from an Executive Assistant role at the San Diego Port Authority to a Broadcast Technician with a local network. I applied mostly through craigslist ads (sign of the times?). I received two job offers in 2011. The first, and I am not kidding, was with Abercrombie & Fitch. I was on campus having lunch and was approached by a recruiter. They proposed a management training program that would see me running a store in two years time. I seriously considered it for a day but then could not come to terms with the idea of working at a place whose brand was the antithesis of everything I believed in. The second, was going business to business selling printers. I shadowed a nice woman for a day and we drove all over East San Diego in her white RAV-4. It was a truly miserable experience and I declined the offer.

It was not until January of 2012 that I received another offer and I accepted a job with a startup called TakeLessons. Meaning I was searching for something for over 6 months. It was pretty rough. But that is what happens when you come out of an educational system that really isn’t structured to set everyone up for success. And certainly my naivety played a big part. I sort of always thought that, like the Ambercrombie offer, the world would simply come to me. I realize how awful this might sound to you. But I'm nothing if not self aware and honest and I am proud of what I’ve learned since then. My advice to college students today is to find focus early, create a vision of your future self, get internships every summer and if possible study Computer Science (CS). Engineering can be hugely rewarding and seems largely recession proof. Given that nearly every company is a “tech” company in some way today, Engineers will/do rule the world.

So my first job was heavy on the cold calling. They call it that because one literally shivers out of unexplainable fear that someone on the other end will actually pick up. New leads would come in and I would hit the dialpad, calling people and attempting to sell music lessons. During down time I would wander around our office. We had extraordinary views of downtown San Diego and the San Diego Bay. One day I wandered over to where the Engineers worked and saw nerf guns, nerdy swag, and all smiles and I thought that was where I belonged. Sales is an unrelenting grind, and in that particular iteration, one that I found was not suitable for me. To the credit of management at TakeLessons they noticed my strengths and moved me over to customer service. I enjoyed that role but fielding complaints all day leaves one quite weary. I decided after 8 months at the company to quit and focus on programming. I had a mentor in my future father in law, and my closest friend was making a great living writing software for a company in Manhattan Beach. I saw in him and in the TakeLessons engineers, a life that I wanted and so I went for it.

To pay the bills while I learned programming, I coached water polo at my old high school and worked for a catering service. I loved both experiences so much and to this day, I often think about working weekends in catering. Everyone of us should study politics and work in the service industry. That should be a college graduation requirement. One semester of International Relations courses and work at a restaurant or catering service to learn some damn empathy, but I digress. I coached, catered, and studied programming for nearly a year before moving to San Francisco in the Fall of 2013. My first ever technical interview was with Evernote which was an excellent experience. It was clear to my interviewer that I was in over my head. This was of course a CS heavy programming question and I obviously did not know CS fundamentals. The last year of study was basically all about building web applications. But my interviewer coached me through the problem with grace and patience. That experience was a catalyst for enrolling in a coding bootcamp which would set me on the path I’d been looking for all along. I am a vocal advocate of the bootcamp space and have deeper thoughts I will share another time. It was an incredible experience to be singularly focused on change with a group of likeminded people. We were a ragtag bunch. The first cohort of a budding coding bootcamp called RocketU. I chose RocketU because I was becoming really comfortable with python and python was part of their Fullstack curriculum. I still missed out on CS fundamentals but, I was able to land a job when the program finished. Primarily because I had an eye for decent design and my final project was nice to look at. It also actually worked! (I had it running until last year. Regrettably, I never really revisited it. You can check out the code here.) There were around 14 of us in that inaugural program and I believe that only 4 are still Engineers today.

Soon, I found myself on the second floor of a converted victorian home in the Marina, building the web application for HeyLets. I still remember when the ping pong table arrived and I’d felt like I too had arrived. Having realized a dream that struck me hard almost exactly 2 years prior when I walked over to Engineering at TakeLessons for the first time. In all likelihood you’ve never heard of HeyLets. It’s one of many startups to fail here in Silicon Valley. We raised a million dollars and had a decent product but never enough users. As our time and runway was disappearing in front of us I was scared. I was completely unsure of myself in CS heavy technical interviews and convinced myself that I could not deliver in that setting. I was however a pretty good coder at that point and could manage the development of web apps across the stack. I desperately wanted to work at either Coinbase or Robinhood. I applied to neither.

Instead I joined Hack Reactor, then, the premier coding bootcamp. But I joined in a non-technical role on the Career Services team. For over two years I worked long hours supporting people like myself who came seeking change and opportunity. It was some of the most rewarding work I’ve done in my life. Being partially responsible for changing someone's own life is highly motivating to me. I came to realize that my calling is working with people. Being in service to others brings me so much joy and pure intrinsic value. The difficulty at Hack Reactor was that the work was always the same. And the bootcamp space was evolving from a boutique offering to a mass produced product. Those are two distinct working environments. I needed a new challenge and I wanted the opportunity to have greater impact as well as learn more about operating a business.

I left Hack Reactor and joined CodeFights (later rebranded to CodeSignal) in May of 2017 as their 9th hire. At the time CodeSignal had raised 10 million dollars and I thought I was on a rocket ship. The product resonated deeply with me. A technical assessment and talent marketplace product that gave engineers the opportunity to prove skill set based simply on solving problems. I could prove that I was good at general programming and weaker on algorithms. Theoretically this still made me a good candidate. I thought we would change the way companies evaluate and recruit technical talent. We had leaders that I still admire and a pretty good product. After a little over a year we hit a rough patch and myself and most of the team I had worked hard to grow were let go. This was purely a business decision and it made sense, but it still hurt to see people I had recruited fired less than a year into their job. The company is still around today and they are thriving. They refocused on coding tests and assessments and dropped the talent marketplace product. Our CEO made a difficult decision and it’s proving to pay off. A solid business operations lesson for me.

So for the first time since looking for a job after the bootcamp three years prior, I found myself in another true job search. I wrote the following advice to myself as a guideline in my search:

Work on having a diverse pool of opportunities. I want to end up at a company working on tackling interesting problems and I want to be surrounded by good people. I want to be director/vp level in two years.

  1. 1 - Solve an interesting/meaningful problem
  2. 2 - Growth opportunities at the company
  3. 3 - Work with people smarter than me
  4. 4 - High growth company on a breakout trajectory

I actually did pretty well this time. I applied to 21 companies, had 4 onsites and received 2 offers. I had the chance to join Affirm but they wanted me to join as a Sourcer and I thought at the time, that was not aligned with the guidance I had written. I joined Oasis Labs because it aligned with everything I wrote to myself.

The draw for me was clear. The first recruiting hire (and employee #12) at a company that just raised 40 million dollars! I absolutely loved my time at Oasis Labs. We had our fair share of issues (founder infighting was new for me) and I learned that indeed, the grass is not always greener. Every single company has its share of issues. But the people at Oasis Labs are truly special. All 30 I’d count myself lucky to work with again. I hit a point where it was clear that my own personal development had hit its peak. Points 2 and 4 felt in jeopardy and I’m not sure how I thought I’d hit Director/VP level in two years! But I can’t hate on my own youthful ambition, however misguided.

That coincided with a referral from someone close to me for a Recruiting role at blockchain.com - I jumped at the opportunity. A London based company, they wanted to build a team in San Francisco, and I wanted to take on that challenge. Looking back I should have remembered the advice I'd written from the last search! Once the curtains were pulled back I came to find myself at a company I didn’t like very much. There existed an inferiority complex permeating from the top down and manifesting in snide put downs and silly finger pointing. Weren’t we a team on the same mission? There were certainly some great people, but not enough in leadership positions. Three months into my tenure, I was asked to leave. We were just getting the ball rolling here in San Francisco. I was tasked with building a pipeline of talent from the ground up something I understood would take at least 3 months. It seems they felt things were moving too slow or else did not enjoy my feedback and desire to make sweeping process changes. Looking back I suppose this was a blessing in disguise despite finding myself in the midst of another job search, this time during the immense challenges associated with COVID19.

I know that there is so much that lies ahead for me, and at a time like this where I am sitting idly it drives me crazy to try and remain patient. In moments of quiet, I find myself reflecting on my path. I wonder what could have been different had I made different decisions. Would I / should I still be programming? I have to remind myself that though it’s been a wild and winding road, I am indeed on the right path. I love working with people and I love the impact that building a team has. The team is the critical component and secret sauce of a company, and it seems like loads of companies take it for granted (I have more thoughts on this that I will write later). I simply want to be in an environment where I can make an impact and where I can see my work serving as a catalyst for success. Where I can build community, do great work with other people, and expand my expertise. I don’t do well sitting idle. My mind wanders, my focus can slip, and doubt can creep in uninvited. Perhaps that’s normal but I try and remain vigilant. I’ve added structure to my days, which is about all I can do to maintain my sanity. Some reading in the morning, job search stuff late morning early afternoon, exercise (crucial), writing / hacking (that’s right I’ve picked up a few hobby projects) in the later afternoon / evening. Cooking!

I’ve had 3 real job searches in my career and am deep into my fourth. Out of college I looked for anything I could find. After I completed the coding bootcamp, I had more clear purpose, looking for any engineering job I could find. After CodeSignal, I had clear marketable skills as a recruiter and my search had clearer focus and was a bit easier than the first two. Currently, after blockchain.com I have clear focus and a lot more to offer, including deeper recruiting expertise but the search has been a challenge. I’ve had nearly a dozen rejections and with each one, I wish I was told why I am not a fit. It’s hard not knowing what people find lacking. All I can do is continue to believe in the value of the path I’ve outlined herein and know that my story will resonate with someone at one of the companies I am fortunate enough to interview at. Building a career is hard work. It’s a series of decisions and lessons. Don’t shy away from asking for help. For me, it requires facing challenges head on, accepting my shortcomings, and continuing to get up every morning with energy, passion, and gratitude.

I share this as both a reminder to myself of what I’ve done and for anyone else interested in a story like mine. It’s nice to find common ground with others. My ambition extends beyond simply being a small fish swimming in an extraordinary pool like that of the Bay Area. I love it here, the energy, the excitement of what people are working on, the passion and ambition. I want to make a difference and leave a legacy. Legacy means something different for all of us. For me it’s about my relationships, the communities I am part of, and helping others. I’ve only just begun.