Ask HN: Leaving cushy job for startup (hire #1). Feed me your wisdom elder ones!

We're in the same boat, I always got envious of the people doing the mad cool stuff and playing mad scientist -- that's what makes the tech blogs, but missed the fact that $MAD_COOL_THING was only a fraction of what they did and that all jobs come with a lot of cruft. Big corps come with more overhead and bureaucracy, and small corps/startups require you wear a lot of hats, some of which you will abhor but need to -- like setting up email marketing/configuring web servers / debugging that support app someone wrote as a one off a year ago that's feeding the CEOs spreadsheets mysteriously and no one knows how. etc. You will dislike some of what you do and it won't be playing mad scientist all the time.

That said, here's a couple things I've learned the hard way to pay attention to when joining a small corp / startup:

1) Ask bout funding. Seriously. How much do they have, what's the burn rate, when do they expect to be self-sustaining (running on sales/revenue rather than seed/VC $$), how profitable are they now, is their capital tied to any contingencies (i.e. they may have "access" to $X dollars to fund the startup but only if they achieve sales figures $Y-Z w/i a certain time frame, I got burned bad by not knowing this). Know the funding situation and be cognizant of what you're getting into.

2) Keep your work/life balance. It's very easy for small companies and startups to eat your life and you're spending all your good hours in the office putting out someone else's fire without any additional compensation / comp time / what have you. It's just expected of you and it's easy to slide into that role. Be vigilant about protecting your free time outside of work and setting boundaries to recharge and refresh yourself. Go to meet ups, go for a run, meet new people, whatever you do. Explicitly carve out time for that and defend it zealously against creep. There will always be more work, another fire, and another do or die moment, without fail. There won't be a redo on life. Live yours.

3) They (leadership) may not be loyal to you. Companies, especially startups, expect fanatical devotion to the product, company, and their vision but they won't be loyal or necessarily upfront with you about how the company is doing. You can get a sense of some of these things based on what crosses your desk, but don't expect die hard loyalty or a commitment to treat staff right. Understand petty politics / business concerns will impact you, especially if there are personality conflicts. Get a sense of who you'll be working with and your rapport and decide if you're comfortable with them. Yes, this is cynical to a certain degree, but I've seen it play out repeatedly to the point of carefully screening coworkers and direct managers to the best of my ability before deciding to join. Life is too short to work with/for people you can't stand (and vice versa).

Edited to fix wording.

Lots of other good info has already been posted so the one thing I'll mention is that eventually people get sick of the "mad scientist" (I know as it has happened to me).

It's great to try new things and live on the bleeding edge but at some point the people you work with are going to get tired of switching to the new hot thing. You can only re-do your architecture so many times before people start tuning you out or start to say "no", then what happens?

You'll go back to doing the same thing you were doing such as adding new features (using the already existing tech), fixing bugs, scaling out, etc. That or you'll find a new place to work which, depending on how long you lasted, means you might lose that equity you were given.

Honestly, if you want to play mad scientist and build cool shit you should be a contractor and build solutions for companies that come to you with problems. You get to build it, hand it over and then move on to the next new thing.