work, visa, life

My legal immigration status, housing situation, and future life plans have been on my mind a bunch lately. I’ve been a bit surprised by how much I’ve enjoyed working for the latest company so far, and it was honestly so great to be able to “shop” around and try working at each of the companies for 1-2 months. Working for a company is kind of like dating - this is 40+ hours of your week you’re committing to, and tied significantly to your mental health and wellbeing. While you can make your best judgement during the interview process, people are obviously going to show their best side at first, and there’s nothing like actually working at the company for a bit to figure out well, what it’s actually like to work at that company.

This is the breakdown of what I’ve learned about company cultures (at least of extremely early-stage, 1-5 people companies) I do and don’t like.

• indexing on hours worked vs value provided (especially for part-time/contractors): I know all 3 companies I worked at cared about my output, but the first two companies paid me a low hourly wage, whereas the third company is paying me purely based on hitting target goals. Getting paid exclusively based on output has its flaws, but at least the incentives are aligned (working better and smarter > purely working more hours). For small companies with limited capital, I understand needing to be frugal and setting tight budgets. The first two companies both reported being very satisfied with my output:time ratio and the quality of my output in general. But when I asked them to raise my hourly salary, they said they didn’t have the budget for it. But…if I’m twice as productive as someone else getting paid the same salary, then it should be a no-brainer. They didn’t seem to be registering that I could just work half the hours and their planned budget and expected output would still be the same, and they’d be able to keep a high-performer on and be able to pay them a proper salary once they get the funding (which they can only do if they build a successful working product). So, I was incentivized to log more hours in order to get paid more, but that’s just devaluing my own productivity. Meanwhile, I see others in the office working from the break of dawn to midnight and getting recognized for their hard work and dedication, but are clearly not outputting the same quality of work (and I could tell leadership felt that way too from their visible frustration and feedback). Of course, companies should want hard workers, but when someone who is actually skilled is so undervalued and for not a great reason, it demonstrates to me a lack of understanding and proper prioritization from the company leadership. Are they trying to hire loyal employees or do they need a particular outcome, no matter what it takes? If I were running a company, it would certainly be the latter.
• market vs product focus: I like to think of working on something as a 2D plot, where point A (where you are today) is at the origin, and point B (your goal) is somewhere on the plot (if it’s a difficult goal, it may be very far from the origin). Your effort is a vector at the origin, and you can control both the magnitude and the direction. It’s pretty easy to measure magnitude - when you zoom-in at the day-to-day or weekly scale, it’s easy to assess whether the team has a lot of momentum or in the negative case, is stagnating. But if your goal isn’t crystal-clear, there is no way to point that vector in the precisely correct direction. Early-stage companies are known to pivot, which means setting point B in a different spot on the plot, and you may have to undo or scrap a lot of existing work. This is totally okay in my opinion, because there’s a bigger goal here which is to create a successful business, so avoiding pivoting when necessary would just be succumbing to sunk-cost fallacy. But, the first two companies clearly were more interested in creating a “great” product versus solving a specific problem with at least one specific customer in mind. There have been examples of successful companies that purely developed impressive technology, but in those cases, I believe the product vision was crystal clear. When there’s a general vibe of wanting to make progress or create something impressive but even the leadership team has difficulty describing what the MVP is supposed to look like and why, that “point B” becomes really nebulous, and even if the team works hard, the direction vector won’t be pointing in the right direction. When trying to draw the fastest path between A and B, making sure the effort is correct can sometimes make an even bigger difference than the amount of sheer effort put in. This has further implications in the day-to-day work - when the goal is completely unambiguous, the team doesn’t require as many alignment meetings (think: every individual draws their own vectors on the plot going in various directions, so the net team effect is much less efficient without alignment). Engineers can be way more autonomous when they know what they need to do, all they need to worry about is how to do it. So, I think founders looking to “build cool technology” without a clear vision is a big red flag - if there’s a clear what and why (usually market-motivated because, well, it’s a company that needs to make money), it makes for a significantly better working experience.
• CEO vs CTO dynamic: this is kind of related to the previous point. I noticed that for the first two companies, the CEOs were very interested in “building something cool” and were quite involved with the technological implementations. I used to think having a technical CEO was good, but I have since learned that it can negatively affect a company when people overstep their boundaries. It’s the CEO’s job to be focused on the business side, and while it’s important for them to understand the technology because they have to sell it, there can be conflict between business and technology. If someone is invested in the technological implementations and outcomes of their project, it will be much harder for them to identify what is strictly good for the business, ignoring the technology. Of course, there are a few exceptions to this: 1) if the business is the technology, 2) if the founder is really great at compartmentalizing. For the first two companies I worked at, the founders may have thought that their business was the technology, but I strongly disagree - I believe this only applies to cutting-edge research, and though there are PhDs on the team, all three companies are definitely doing engineering (i.e. implementation), not research. Another big lesson I learned via observation was the second company’s CEO was also the technical one (had a PhD), and he joined an accelerator program where he found his CTO. However, his CTO was very weak in my opinion, and it made the dynamic extremely uncomfortable when I worked with them. The CEO was micromanaging his CTO more than me. The first few hires are so critical to a company, but of course your co-founder is by far the most critical person - you need to be extremely, extremely picky.
• company business prospects vs team vibe: This isn’t a tradeoff, of course you can have company with both a great business model and a great team vibe. If you were a founder, there would be nothing more important than the company business prospects. With no successful business, there wouldn’t be a company left. However, as an employee, you mostly don’t have to worry about that. Yes, a successful business means job security, but successful businesses can also fire you (and truly successful businesses will fire/layoff people), so you don’t actually have job security anyways (and in the big picture, maybe you still do have job security because there are plenty of employment opportunities, but it’s hard to generalize). That means, what really matters is the day-to-day. When I used to assess startups, I’d ask questions like: do I think this business will be successful? is the work interesting and meaningful? But now, it looks more like: am I properly valued? do I like the people I work with? am I given sufficient autonomy? These are not all independent variables, e.g. a company will have a much easier time hiring great people if they already have great people, which they would only be able to hire and retain in the first place if they valued them enough, which is only possible if they create a sufficiently successful business. But I’m not a VC and while I will be compensated in equity, it’s important to remember that there is a 1% chance of realizing this equity no matter which company I join, so while a bunch of extra bonus money is nice, I’ve stopped trying to assess if a company will be successful on the business-side (the answer is: probably not). I only really need to think about if the salary I get paid is sufficient and satisfactory. Other than that, if I love my day-to-day, I will have no regrets if the company ends up folding (which it might for literally any reason), and I will have maintained my sanity and hopefully grown a lot as a person in the meantime. Of course, if your goal is to make the most money at any cost, either join a startup you have total financial conviction on (e.g. a fintech company), or stay in big tech. Not much point in working at startups for funsies.

Next up, visa update. I talked to my company’s immigration lawyer and he was very nice and chill and said I could stay in Japan legally until my visa expires in March 2026, even if I’m not currently enrolled in school. This was great news, because I’ve been thinking about quitting school even before the semester ends. He warned me that my school will be unhappy about it, which they were when I told them. It’s so annoying because I need to talk to them in Japanese, and I don’t really have the negotiate-your-visa-status vocabulary yet. Maybe it’s good motivation to learn. I’m still not sure how long my work visa application will take because my company just incorporated, so it will take some time to get their financial situation straightened out and establish trust with the Japanese government.

My latest plan is to go back to the US for a month over Christmas/January, say hi to my friends and family because I honestly do miss people (the lack of consistent and familiar friends in Tokyo is wearing down on me a lot), and then figure out what to do about my living situation. I’ve been thinking about moving out of Tokyo (like, right outside the border potentially) because I heard it’s much faster to get your Permanent Residency application processed outside of Tokyo, and it’s cheaper. However, I’ve since learned that once you get PR, your global income may be subject to Japanese tax once you live in Japan long enough, so I don’t even know if I want PR anymore. But, the area south of Tokyo (i.e. Kanagawa) is also closer to the triathlon club OWS practice, which also means more club members live there, so that is a plus honestly. I also don’t know if I should cancel my apartment lease by the end of Dec right before I leave, or keep my apartment and sublet it out while I’m gone, and have a less stressful time moving into a new apartment once I’m back. The answer is probably to just keep my apartment around now that I’m thinking out loud…if you’re reading this and you’re interested in staying in my apartment in Tokyo from the end of December to late January, you know who to hit up.