Ask HN: How do I choose? Amazon vs. Late Stage Startup

I’ve worked at big companies and small. I much prefer small (though 300 isn’t all that small). I would love the opportunity to spin up a green-field project inside an existing company. That being said, if the project doesn’t work what happens then?

How’s the smaller company’s culture and their funding? Can you find any ex-employees to talk to? They know where all the bodies are buried and have nothing to lose telling you.

Every startup has a runway. Funding is very challenging right now. Make sure they are straightforward with you about the funding future. How well will the product weather the coming recession?

You will probably have stock options at smaller company. What’s your honest assessment of the likelihood of those options being worth anything? To be perfectly frank, most startup stock options are worthless. But when they’re not they can bring your total comp up a lot.

You know how the culture is at Amazon. Picture yourself in each place, imagine how the work will make you feel. I suspect this last question will answer the question for you.

I worry that even Small Co is too big for you to really play a large part in a new feature, especially depending when you are joining this project and team structure. You easily risk all of the overhead and politics of an Amazon, but for less pay.

The question you need to ask yourself, do you want to be a big fish in a small pond or a small fish in the ocean? Next, see where you want to go 3 years from now, do you want to move from Individual Contributor to Leadership? Small Co will be better as you are more likely to stand out, can have direct communication about your goals, and work with your boss to align your goals to your work. If you want to get more technical, you could drive an architecture path in Small Co.

If I was in my early 20s I would certainly go for more money, but after making a couple hundred thousand dollars at 25 I was purely gunning for projects I was interested in.

The money became really unfulfilling to my mental health, and after 150k it really doesn't matter until you make the jump to 250k+.

I'd optimize for whatever will make you not dread going into work every Monday.

I've tried to optimize for money at various points in my career (admittedly not FAANG money which may be enough to make a difference, though I'm skeptical of that), but inevitably I'm starting to look for an exit after 6 months.

A high level of autonomy and ownership is what I've discovered I need in my work (something I've so far only really been able to find at small 5-15 person start ups), which is easily worth $20-30k for me.

Agree with the other comments that 300 employees is more "Mid-sized" with potentially a lot of process and overhead though, so may not be as free as they are making it sound (though still maybe be a better environment to work at than being squeezed at Amazon).

Take the easy gig that pays better. Work on something in your spare time that scratches your itch.

Also, don't neglect your personal life. Mid 20s turns into mid 30s faster than you think. If you want a family there's a clock ticking. Either way, you ought to find something outside of work that will provide you long term fulfillment.

That small co is not small enough for you to learn as much as you think you will. Take amazon.

Small to me means 4-5 people where you are forced to do a lot more than your job calls you to. In this case, a 300 size company will have annoying growing pains at that size (organizationally), whereas amazon will be more stable, be a better launchpad for your career, and if you find a small team in there, probably has startup vibes anyway.

Start at Amazon.. Do 2-3 years. Take that experience and skillset you pickup to a Start-Up or start your own company using what you've learned. The Amazon job may also give you the startup capital you need to start a company of your own.

Some people say to have a boring day job but do side projects outside of work.

Personally after working 8 hours the last thing I want to do is more programming/staring at a screen. I much prefer to do other totally unrelated hobbies.

Been in similar situation as OP, chose the more interesting job for similar pay difference and didn't regret it but YMMV

Don’t work at Amazon. It remains true the you only live the once.