I've worked mainly at startup organizations since I got out of school. I turned 30 last week. None of the startups I worked at panned out, all but the last has folded (try getting references when every company you've worked at no longer exists), and all the equity I ever vested is worth less than the papers I had to sign to get it.

So, I'm 30, still job hopping, have no meaningful financial assets to speak of, and I sit around and listen to people say your 20s are for building up a massive hoard of cash and investments so you can live the rest of your life. Ouch. Failureland. Yes, it's my fault. I didn't recalibrate my salary when insanity struck and fresh bumbling BSCS graduates started making more than me with eight years of relevant experience. I could have gone to a Big Corp and had a Soul Crushing Job with Better Pay for the past eight years. I could be a millionaire by now with careful saving. But, no. Move fast and ruin your life. Let the 20-something founders "take money off the table" while watching the rest of the company honestly believe they are amazing, almost touched-by-god people. Work for sub-market wages with free lunches, work-on-whatever-you-want policies, and unlimited vacation days. Shoot for the stars. Enable the dreams of the founders and first five employees who were hired five years ago to cash out. Just keep moving diagonally. (pretend I made an elaborate chess joke at the end there)

Perhaps we just need better transportation so I can commute to jobs in SF and NYC while living in Iowa.

This is not really true all the time, you know. You should probably pick up and try it out for a while.

There are different levels of big corp, but there's a price on every side.

That was uncalled-for.

None of the startups I worked at panned out, all but the last has folded (try getting references when every company you've worked at no longer exists), and all the equity I ever vested is worth less than the papers I had to sign to get it.

I just turned 30 as well, so I'm the same age as you are.

This is fairly typical, and you shouldn't feel bad about it. Most of the information that you need to evaluate a startup job is not available to an engineer in his 20s.

I've concluded that you don't do startup jobs for employee equity. You do them for high positions (as the firm matures) and introductions. This means you have to ask yourself: will the CEO be making introductions on my behalf, so I could do my own startup if I wanted, in 24-36 months? If yes, continue on. If no, don't.

The worst thing that happens isn't joining a startup and getting low equity, because that's typical and not really insulting or a reflection on you-- it's just business. Market conditions are such that you don't really have position to ask for more equity. Much worse is joining a startup and having it grow above you. It's not only humiliating, but it means you've irreversibly fallen into the "not a real player" bucket and should leave because it's only going to get worse.

However, the job volatility of the startup market does make you a less attractive candidate in the future, and people don't talk about it much, but the "job hopper" stigma is still alive outside of VC-funded startups.

I sit around and listen to people say your 20s are for building up a massive hoard of cash and investments so you can live the rest of your life. Ouch. Failureland.

If it makes you feel better, I bet that less than 5% of people our age have more than $25,000 in net worth. Our generation has been screwed but, to our benefit, demography favors us being politically powerful in the 2020s to '40s. We'll be broke in the near future, but the political torch is passing to us.

Being a large/dominant generation (which we are, like the Boomers) is bad when you're young because of wage depression and competition-- this is part of why the Boomers rebelled in the 1960s; compared to what their parents faced, the workplace was getting much more competitive-- but it starts to favor a generation in middle age because they become the political core.

Move fast and ruin your life.

Well said. The real crime of this system isn't that startups don't pay well and that equity slices are small. The deep injustice is in the long-term career effects that no one talks about. If you have 5 no-name startups on your resume, that hedge fund job is a lot harder to get. Ten years ago, finance was pretty hot for technical talent of any kind; but, in 2013, the typical job-hopping of our world gets you creamed on "cultural fit". Hedge funds are a different world-- they pay better and I think their cultures are usually better than what most startups have-- but more conservative, more superficially conformist, and (because of the trade-secret risk) not likely to hire someone who seems to leave jobs quickly (even though, with most startups, you can tell if you're wasting your time at 6 months). Startups know that the degenerate job hoppers out there (which are a small fraction of all job hoppers; most of us leave quickly not because of character flaws, but just because most jobs aren't worth keeping) aren't an existential danger, because amassing the connections and managing investors and building a brand is very hard; but hedge funds have a justified fear of people stealing their trading strategies and don't want to hire people with quick feet.

If I wanted to go gray hat, my startup would be to generate a bunch of shell companies (staffed by people who offer references) with nice websites and offer career plastic surgery "as a service" for people with damaged resumes. One could even typo-squat established companies ("tell me about your time at Göldman"). The sad thing is, it's probably the best startup idea I've ever had. I know there's a market (startup peons with damaged careers) for it, making money would be ridiculously easy, and it would probably be good for society. Unfortunately, the reputation issues would be pretty severe; it'd be the last startup I ever did.

Work for sub-market wages with free lunches, work-on-whatever-you-want policies, and unlimited vacation days.

I'm a huge champion of open allocation (which is not as extreme as "work on whatever you want"; you're still responsible for working on something of value to the firm) but any startup that has a "work on whatever you want" policy is either lying or destined for failure. Startups need focus, and they need implicit focus (low management overhead) which means there isn't an open/closed allocation distinction yet because they work as one team. Open allocation starts to be the right way to go around 15-50 people.

Perhaps we just need better transportation so I can commute to jobs in SF and NYC while living in Iowa.

This is what I've learned. If you work in New York or the Valley in your 20s, that is your savings. You lose everything to rent, which means that the reputation premium you get from working high-status jobs better be strong.

I think that, as our generation gets increasingly jaded and as a larger number of smart people return from NYC and SF empty-handed, society will absorb the signal and the next decade of technical talent will want to avoid the high-rent cities (which will remain expensive for other reasons). I could see Austin or Seattle or even Chicago (which, by rights, should have a strong tech scene) taking the lion's share of the new action.

Um... what else are we talking about here.

Oh, right. Loserdom.

Well, I don't feel bad about anything. I enjoy having had a series of jobs where I could show up at 10am and leave at 3pm or take a week off to do a 600 mile bike ride or tell my boss "No, I won't do what you ask. It's unreasonable." knowing he has no real power in the organization.

With all the startups I worked at, I never exercised my options. It was clear they were loser startups with loser founders and loser execs. They were comfortable for a time though. HN money boasting brings out all the people who have been at google since they were 23 and have been making $250k/year for the past eight years though. That kinda hurts. But, the world is big—we can be better than The Safe Path.

I'm not sure how much damage the "job hopper" stigma imparts. People know shit happens. Some people.

Your "one new tech hub outside SF/NYC" is way too timid. Try twelve new ones. I've got a writeup about that in my head needing to make its way out through my fingers soon.

Your rent-is-overgrown-evil rants are top notch. We're one step away from landlords demanding to know how much you make so they can set the apartment price to exactly 1/3rd of your take home pay.

Honestly, the best thing we (as people who haven't achieved greatness in the face of media constantly focusing solely on 18 year olds becoming millionaires) can do is to stop reading the news. Get out of your head. Mindfulness. Talk enough to change the direction of opinion in the world. Let it sink in. Talk some more. Shut up for a while and create good things. At least try. There is no try.

We're only left with one practical path to greatness: Make good art.

Happy 4th.