Ask HN: FOMO by working in startups only vs. Big companies

My rule of thumb: if it's big enough to have a dedicated HR person, it's not "really" a startup. Or it's not going to feel like one.

The best size IMHO is ~100-1000 employees. Big enough that you have resources at your disposal, but small enough that you can just pick up a problem and start working it.

I've done much of both.

Working at a big company is much easier, but it's harder to get things done. You'll have at least 10 hours a week in meetings. The CEO or a guest speaker will deliver a Ted Talk speech once every 3 months.

Try getting a server deployed for an internal side project. Even if everyone wants it, your wading though miles of redtape.

Startups are more fun, but less stable. The stress is intense. I'm in my 30s and unless I personally know the founders, I'm never working in a startup again. The Company might just randomly shut down !

I can relate to a lot of what you've said here. I've built a similar super-generalist profile in software engineering and have spent the last decade in startups.

Compared to my peers/friends in larger companies, I've always had far less politics/BS to deal with at work. I would not say its non-existent; sometimes all it takes is one bad hire, and the smaller the startup the more outsized the impact of the bad apple. So in that sense, impact is a double-edged sword.

On the other hand, I've been able to build a super-generalist profile because of the startups I've worked at. Backend-engineering, frond-end stuff, DevOps, hands-on data-center experience, automated QA, SRE, growth hacking; you name it and I've probably checked that box off at some point in the last 10 years; mostly because I've been able to cultivate good relationships within the company to be able to move around different roles. This would be impossible in a large company, even with a lot of personal connections. A few jumps are possible, but not the kind I'm describing above.

The smaller size of startups also means that you have fewer people between yourself and key decision-makers. I've had the good fortune of being able to work directly with/report to CXOs for over half a decade, which IMO provides a lot more exposure to understanding how a business operates. I would not trade that for working with mid-tier management in most large companies.

With regards to not being appealing to large companies, I'd say that is not true. I've known folks who've moved from startups to FAANG companies in their mid-40s without any issues. The experience always counts. You may lack some of the specialization, but you can always compensate for that with breadth of experience.

Ultimately it boils down to what you want to accomplish. If your goal is to eventually start your own business, working at startups is a great way to get the requisite experience. It is definitely not a walk in the park though. Being able to work with little to no direction, constantly changing goal posts, and the lack of any structure does take its toll on you slowly, but surely. However, I can say from personal experience that I don't regret it one bit.

Just seconding stuff that's already been posted by multiple people:

1) You should absolutely try both. You've already done some startups, so now would be a good time to try a big corp. They each have upsides and downsides, and it really depends on you as an individual as to which one you'll be happier at, as well as more successful at.

2) It's all about the people you work with and report to. Really, you should choose based on the team rather than the size of the company. If they are all smart, cool people you get along with, then you'll be fine even if it's a fucking bank (source: I work at a bank presently and it's great). On the other hand if they're incompetent, egotistical assholes, it's going to suck big time regardless of how many foozball tables or beer fridges the company has.

editing to add, at a big corp, a good manager should understand that their job is to insulate their reports from as much of the bullshit as possible. That's critical. You should be able to get a sense of this during the interview, even. If they're up front about the bullshit from the get go, that's a good sign. If they're actively trying to make you drink Kool-Aid... run.

I've never worked at a larger company (>100) so I could be wrong but I don't think I'd enjoy it. Endless bureaucracy, office politics, and stifling policies. At a smaller company I can see my impact directly, I have the power to actually make decisions on how things are done, and I get to build cool new things. Don't assume that big companies know "the right way" to do things, they are just as fallible and sometimes even more so. They can fall into the "that's the way we've always done it" much easier than smaller companies. Also I can tell you from personal experience that more people/engineers does not mean a better product. A better funded one maybe but without naming any names let's just say that I've consumed APIs or similar from massive companies that I once looked up to or put on a pedestal and their API was trash and/or their software was a mess. It really helped break my long-held assumptions that they hire the best talent and produce the best code.

Don't feel like you are missing out, you are only missing out on a bunch of headaches IMHO. I've only worked for smaller companies and I have no doubt I could swing a job at a larger place if I wanted, I regularly ignore recruiters from AWS and the like because I don't want to work in that type of environment. Do what you like and make sure you get paid well for it, past that don't worry about company size.