Having worked in both startups funded by VC's (or wishing to be), and for businesses not part of that, the primary difference is in the attitude towards boring technology. Main Street is not really any better at seeing through hype cycles than anyone else, but they are less up-to-date on what is currently hyped, and they also are more likely to think that they hired the programmer to make technical decisions, rather than wanting to make those technical decisions themselves. They have other (often equally technical) decisions to concentrate on, in different areas, so they are wanting you to just Make It Work.

The downside is they are unimpressed with refactoring, updating to new versions, and the like. The upside is they are ok with you using boring technology that works, even at times when a VC-backed tech company would insist on something new and overcomplicated.

Also, the pay is ok, but honestly it's not going to be as high as in VC-backed employers.

> Also, the pay is ok, but honestly it's not going to be as high as in VC-backed employers.

This, for me, has always been the deal breaker in moving out of VC-funded tech. Leaving corporate tech jobs is already a big enough hit to TC. Getting out of VC-funded tech very often means a dramatic change in life style. The VC world might be insane, but so is the comp.

It's not just the money. The biggest thing I've notice in my career is that, as a general rule, employers value you (or any resource for that matter) in proportion to how much they pay for you. Often people have the illusion that getting paid $80k a year when you used to make $300k will mean that your employer will recognize that you are a tremendous value. They won't. they'll see you and treat you as a low tier worker that can easily be replaced, has timed breaks and 30 minutes for lunch.

Might be true most places, but I’m paid 80k and essentially report to no one and do next nothing 10 months of the year with no real supervision or expectation. My employer struggles to find people with my exact stack who doesn’t expect over 100k.

If you follow American football it’s often said the best job on the team is the back-up Quarterback. Because they sit on the bench all year and still get to get a sizable check considering. Pretty much the position I find myself in.

Most (not all) of these jobs don't last -- I have had two, and while they were fun we eventually got bought and everything changed.

Well I’m celebrating my 10th anniversary in April, but it it’s how you play your cards. I just go to meetings keep up with the stack and agree with everything. The developers love me because I will always endorse any decision they make. Product loves me because I’m bailing out projects the seniors won’t touch. If I succeed, Product hero, if i fail well we should have listened to the engineers in the first place.

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Congratulations, at 10 years you probably have beaten the odds and will continue making some money off of this for as long as you both shall live.

What exactly do you mean?

The only people who make “actual” money at the average startups that exit (acquired or scrapped to PE) are founders, maybe the first 5 hires.

I’ve worked at only one startup. We IPO’d. I did pretty good and I joined a unicorn at like series B. Enough to go a decade figuring out what I want to work on next.

Most of my other friends went to work at other startups. Most of them went bust and they made nothing but their base salary (and a couple of them got screwed on that too).

So unless someone’s working at an actual unicorn like I was it’s really no guarantee.

FWIW I made 8x on my latest shares, and multiples on that on earliest. Some people I know who had been there a few years more than me walked away with many more Ms which ain’t bad for 6-8 years of work.

But that is SUPER lucky. It has sort of ruined my outlook too because I have no interest making 250k base + 200k RSUs, and I have zero interest in most of these current startups that I have a good hunch will not work out. And 400k isn’t that meaningful anymore, I’d rather live off interest or work as a barista if my own startup doesn’t work out.

Most bay area startups pay between 250-350k (not including equity) for senior roles. I know because these were offers I was getting a few months ago. A liquidity event is not required to make substantially more than the average “main st.” dev.

The chance at making FU money is what would be worth it.

It doesn't sound too appealing if its 40-50% more total comp and 100% more work/stress and less time for myself plus random things like losing funding or startup goes bust and can't make payroll, etc.

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> Often people have the illusion that getting paid $80k a year when you used to make $300k will mean that your employer will recognize that you are a tremendous value. They won't.

Sounds like the folk wisdom that, by default, employers/clients tend to only value you how much they're paying you.

If they had to pay a lot extra for you, the wisdom goes, they will imagine that you must have been worth it, and will take you more seriously.

If they paid bargain basement price for you, well, I suppose the same psychology applies.

(I was reminded of this folk wisdom last week, by a couple hints in an interview. It's a bit tricky to filter out startup employers who only want midrange commodity skillsets, when you're willing to take a lower salary in exchange for meaningful equity. While many of them are thinking of workers as generic commodities (and necessary evils, to the real stars who are the founders), and valuing these hires based on salary they are willing to entertain.)

If you are solving their problems and they see you are solving their problems it's pretty easy to get a seat at the table IF you are also put together like you used to make $300k (dress upper level, don't be out of shape, be attractive/well groomed, have upper level hobbies, decent car, picture on your desk from vacation in an exotic place, have a tag or higher watch). You might also need to play a little business politics and build up whoever is your champion/boss.

If you are good at figuring out how to solve problems, your issue will be they will want to raise you up back to higher level stress positions, and it can be hard to resist being 'superman' and getting kudos again. Every $80k job I took after burning out I ended up leading a department or being a Director and pilling myself with stress again.

If you are just an $80k worker bee you will be treated like a worker bee. But you don't have to be that.

This was my experience, until a bunch of startups tried to come after the boring business I work for. They’ve since brought in a bunch of new people who brought hype cycles with them, and have pushed out the boring and stable solutions, in favor of more complicated trends that need to be migrated or re-written every couple years.

My job satisfaction has dropped dramatically. I found meaning in the boring stuff. The hyped solutions that will be thrown out in a year feel so meaningless.

This is all to say that not all Main Street businesses will appreciate the boring solutions. And if they do right now, things can and will likely shift at some point.

That's mostly what I've come to expect. One thing I think you added, though, is that there's a greater expectation to be the expert in the room.

Any advice on taking the best parts of working at VC-backed startups (outside of comp) and applying them to roles on Main Street?

Version control! Testing! Deployment with a user-acceptance stage! A commitment to tracking bugs and solving them prior to new features! Talking to end-users after the first roll-out!

Some or all of those will come as a surprise to the people you are working for.

This is all true. It is also my experience that Main Street is willing to let you institute a low-cost solution to any of these, as long as it doesn't require them to do much (which, often, it does not).

> the attitude towards boring technology

PTSD flashback of nobody having heard of Redis.