rememberlenny

Tomorrow is my birthday, and I turn 31 years old. I didn’t think as much about what turning 30 meant last year, so taking a pause to write down some thoughts about the last 10 years, and the next 10. Taking time to think about my happiness, goals for future, current life circumstances, and future concerns. There is a global pandemic going on, but outside of this sentence, I won’t mention it again.

Ten years ago, in 2010, I lived in Aliso Viejo, had a blackberry, an HP laptop, and drove a stick shift Saturn. I had been back to college for one entire year, after dropping out and moving to Los Angeles, where I lived in a one bedroom apartment with ten other tenants, while figuring out what I was trying to do with my life. Prior, I worked a graveyard shift at CVS (10pm to 6am), and found time to paint graffiti on rooftops and empty streets. By the Fall semester of 2010, most of my classmates were on study abroad, and I was in the midst of a clinical trial to pay off some credit card debt I accumulated. My best friend was in rehab, and I began taking my Buddhist practice seriously to ground myself and master my own tendencies. I began painting canvases as a means of blowing off steam, and also began exploring how to program. I worked in a concert hall as a part-time gig, and pursued contract web development opportunities on craigslist.

Ten years ago, I wasn’t on Twitter, I didn’t know who Paul Graham or Peter Thiel was, I didn’t know anyone who worked at or ran a startup, and I wasn’t on a pursuit for wealth or riches. My parents were finally settling into a regular life, after our family went through a drawn out bankruptcy and legal dispute with a nation state. And a reasonable trajectory for me was either grad school or a well paying job. I recall seriously thinking I would attend law school, reading the One-L, and even starting a club at school to prepare for the LSAT.

By 2010, I had developed interest in the digital humanities and online culture, specifically from the lens of communication theory. I researched everything I could about Reddit, and believed that the intellectual and social capital found in subreddits was a completely untapped resource. The Arab spring was erupting and I recognized that the live updates found from direct experts in subreddits was far more valuable than anything the news was publishing. The on-the-ground photos and clear community run explainers felt like the future.

As a student, I was studying Chinese – poorly – and doubled down on an academic interest in propaganda, marketing, and what “dialogue” looked like online. I thought the Chinese influence in Africa was the most under appreciated power play for the century. I was also pursuing a personal interest in local politics, by attending city council meetings – and considering a possibly future in education, which I vetted through volunteering at a nearby alternative school. 

In a nutshell, 2010 was the decline in my academic focus, and my shift toward a pragmatic commercial future. I had peaked my interest in getting the best grades, and shifted to wanting to learn the most without wasting my time. I was considering moving to China after college, where I thought I could get experience in wholesale trading and factory production, but also considered the values of knowing Mandarin for what ever global political shifts were to come. 

Outside of the Arab Spring, I wasn’t mentally or emotionally invested in the US occupation of the Middle East, and had been largely apolitical outside of the excitement around Barak Obama’s presidency. 

In 2011, I was elected as the attorney general of the school student government, and did my best to contribute to the university’s mission. I can’t point to any long lasting change that was made, but that period gave me a close look into the operations of a Robert’s Rules oriented body. Looking back, I was hyper focused on the “creation of value” and maximizing my time spent.

Since I had dropped out of college for a semester in 2008, all of my entering classmates had graduated by the spring of 2011, and I was absorbed into the following 2012 classes’ student body. At this point, I also moved out of the college dorm, which 95% of student body lived in, and commuted by bike from my parents home to attend classes.

Over the next two years, the major events in my life were my older brother’s death, and moving to China. 

I arrived in China in the winter of 2012. I began my travels with a month long trip with a classmate in the Western Yunnan province. We spent a month going between tropical climates in the south to the coldest areas in the north bordering Tibet. The month of traveling was what I thought would be a good transition between my final semester of school.

From Yunnan, I took a two day overnight train to Shanghai, crossing from the Western most part to Eastern most part of China. I was ready to start school, and also kept my attention on the possibility of finding work. I also connected with local street artists, who had a graffiti studio. This group of friends ended up becoming major influence in my following decisions.

While I started language classes, I quickly realized I did not feel the effort needed to succeed would necessarily result in learning the language. Instead, I felt the classes would be a waste of time, and given the recent events in my life, there were more important things I could focus on. I ended up finding a part time job as a bartender, actively engaged myself in the startup tech community, and began actively soliciting work as a web developer.

Surprising to myself, I was able to find quite a bit of work very quickly, and realized that school was not necessary for me to take the next steps in my life. Not completing the one semester I had left for a college diploma was not the greatest of choices, but at the time, I considered it would be possible to finish later.

At my peak in China, I had grown quite comfortable with working multiple jobs, and furthering my programming ability. I had a very fortunate series of events, during which the one weekend I took off for a school trip, my bartending workplace was raided by the police for employing international workers. This reinforced my doubling down on programming related income streams, which by that time I had plenty. I grew comfortable with finding new web development clients by going to foreign businesses that I thought might need programming help, or by talking to foreigners at coffee shops and introducing myself. This was surprisingly effective.

In 2013, approximately at the one year mark in China, I decided it would be valuable to finish my college diploma. I wanted to personalize that I could move on to the next phase of life, confident that I finished the things I started. This was quite a shift, going from working every day to being a student.

Through a series of factors, I decided New York was likely the most similar place to Shanghai, given my attention on wanting to find a job and avoid moving back home with my parents in California. At the time, a girl I liked from college lived in New York, and I thought if we were in the same city, it was possible for us to get together. While initially that wasn’t the case, we are now married.

In New York, I enrolled in weekend Chinese language classes and a full-time contractor web development job. I hustled for the next few months and finished my college diploma, which was a major accomplishment given the series of options I had available. Soon from there, I began my first full-time salary based employment in the media industry as a senior level software engineer. Up until then, although I had never actually worked at a company, my contractor jobs had resulted in advancing my knowledge in areas that companies happened to need. I was always under the impression that I didn’t know enough, but given the constantly changing nature of software, what I had learned was the most important at the time. 

From 2014 and on, the following years were largely based around my work and side projects. Most of my time outside of work was heavily engaged in my Buddhist community, where I would attend meetings, visit with friends, and help organize numerous weekly activities. Also being relatively new to New York, I attended meetups in the tech industry, so that I could learn what I didn’t know. I volunteered at conferences, co-organized hackathons, and made a weekly routine of reaching out to people online to meet in person.

At one point, the team I was on at work had been awarded recognition for performance, which made a major impact on my sense of accomplishment. At one level, I was very aware that we just did our job, but instead happened to be working on the right thing at that time. Our team had launched the New Yorker paywall, and in the process, made off without a hitch. A precious memory was the official launch, upon which some of us slept over in the office to see the job through. 

Throughout this time, I was more and more aware of the potential of starting a company. I still hadn’t taken any concrete steps, but absorbed the startup narrative around the difficulty of hiring. I took that and decided to maximize the number of people I could meet in case of some future event that would allow me to hire my friends. I got involved in many incredible communities of designers, programmers and entrepreneurs.

Notable in 2014, I started a routine of traveling to a new country every few months. I went to Ecuador and Peru for two weeks to go on a road trip with friends. I also went to Berlin fo a tech conference, of which I made some great friends. In the following years, I also made a short trip to India, where I was able to get away and focus on a personal project.

By 2015, my effort to “network” was in full swing. I wasn’t intentionally going to networking events, but for the meetups I did attend, I always tried to make one friend who I would then plan to get breakfast with at a later time. I had hit my stride at work, and while contributing to the advancement of my team, I didn’t want to limit myself to a job, and saw my engagement in side projects as a crucial factor in my learning. I was highly aware that the work I was doing at that point was only possible from the many side projects and contract gigs that I had done before, so my pace of out-of-work work was critical.

Around this time, I attended various classes and enrolled in extracurricular learning opportunities to propel my technical knowledge. I was aware that while I could be employed as a senior level software engineer, my colleagues had spent years studying computer science and had a technical foundation that I was unfamiliar with. In the big picture, this was not as important as long as I was proving my execution ability, but the awareness of this lacking knowledge had continued to motivate me.

Although I didn’t need to at the time, I found opportunities to contract with major companies I never imagined working with, and also continued my in-person public soliciting of web development.

In the midst of working, a major shift happened in which I started a serious relationship with my now wife. Prior to this point, much of my personal activities were barely keeping my head above water. Planning, communicating, and coordinating with others was not my forte. Acting on impulse and corralling others was my strength. Through a series of major mess ups as a boyfriend, such as double booking a celebratory birthday trip, and bailing on major holiday celebrations, I started maturing as a person who could truly consider and plan around the needs of others. This is something that until being in a relationship, I was able to get by without.

By 2016 and on, I was in a new job, working for the federal government of all places. I didn’t foresee that given my juvenile trouble making. The ability to work for a cause oriented organization was a big shift I was yearning for. Also given my workload, I was making a mental shift away from continuing so much contract work and wanted to double down on projects that aligned with some meaningful future state. I was tired of the transactional one-off clients, and wanted to see the work I did outlast me.

A number of my side projects from 2014 were still active, and I considered occasionally trying to translate the ideas into businesses. Two in particular were a street art tracking project and a service for publishers to engage readers who didn’t finish reading long content. In the midst, I also seriously pursued a project to help people working on side projects to gather an audience before they are ready to launch. Interestingly, now in 2020, this is a surprisingly common company theme at the cross section of a Twitter meets OnlyFans. Another major project was an attempt to codify my practice of meeting strangers for breakfast, but as a service to meet other professionals. Based on my exposure to the professional world, I only saw the value to expand around side projects, but now realize the larger potential of the idea.

My shift aware from short term pay and longer term self sustaining projects eventually resulted in my exploration into harder technical fields. This aligned with the popularization of machine learning. Specifically the advancements around image recognition, which made computer vision applications approachable. Given my prior interest in tracking street art, this drove me to look at working in a company in this space. With two years at the federal government, a startup seemed appealing.

Worth noting, while in China, I worked at a startup that was somewhat in a unique situation. As a company that had raised venture capital, they spent too much money, too early, without product market fit. When they finally got to a point where growth would be important for capturing market share, they couldn’t raise another round of funding. One cherished memory at this Chinese startup was our pure scrappiness as a company. The office we worked out of was in such state that although we had desks, the rest of the floor plan was under construction. This resulted in exposed live wires and the need to wear particle filtration masks while working, due to the construction materials in the air. Good times.

Coming back to now – the major events in my life recently were around getting married and the shifts leading up to it. As I saw gettin married as a major life event, I reconsidered my role at the startup I was at, based on my financial optionality. I gauged how much the stocks I owned could be worth, and realized that my time working at a larger tech company would likely be more valuable and less risky. While not initially having anything lined up, I contracted as a UX engineer at Google, which topped any other workplace I was at before. My specific responsibilities were on a team of contractors, but gave me insight into the big tech company ecosystem.

Outside of work, a major part of 2016 to 2018 was a youth festival organized by my Buddhist organization. We gathered 50,000 people at 9 different venues around the country. The largest which was in New York, the organization that I was most invested in. The entire festival and preparation required incredible effort in my life, which I felt deeply appreciative to have been able to make.

While the preparation for the festival put traveling and side projects on hold, I had been able to make steady progress on scraping street art off the internet. This fortunately got some attention, which eventually allowed me to participate in some events which were hugely formative in my interest around building a company. For one, I was able to meet face to face with many established founders of multi-billion dollar enterprises, and put a secular quantifiable form to my own interests in positive societal change.

I was also able to go to Japan, and Korea for work and a friends wedding. I feel there is much of the world which I am still yearning to see. Unmentioned earlier, I was able to take a very refreshing trip with my wife to Europe, upon which I visited Paris, Budapest, and briefly Lisbon.

By now, I am capturing a very wide period of my life, and largely focusing on elements surrounding work, career, and personal relationships. There is much more to unpack, and countless meaningful experiences and personal relationships I never touched on, but at a high level, this provides some perspective on how I think about the last ten years.

In most recent notable change, I ended my contract with google, started a full time job, and two months later left that job. I finally realized that I want to commit seriously to building a company, and believe there is never a right time, so I will do it now. In these last 10 years, I haven’t exclusively worked on one thing in isolation, and feel this is a major personal shift which was a long time coming. As I determine to grow my current project into something that I can both be proud of, I expect a lot more personal development to take place.

I started out writing thinking that I am considering what my next 10 years will look like, in addition to the 10 years of reflection. At this point, I know for certain that my next ten years will involve starting a family, and being more invested in the outcomes of my extended family, on both my wife and my side.

I do want to formulate some clear themes around how I imagine my next ten years to resonate, but for now this is what I have.