If he is an amazing engineer, he's not "excluded" from the culture. You need a command line and an internet connection to start your own thing.

"Start" vs. "join". I wouldn't want to be a 45-year-old at a typical VC-istan startup where the founders are in their 30s, so "join" isn't much of an option, and I think it's hard to start your own startup if you're older (or more than 10 years younger, except in bubble times when youth becomes hot) than the average VC.

Few people do startups for the "promise of striking it rich". They do it to "make it big", which is not the same thing. They are more fame- and impact- motivated than dollar motivated. So this right there bespeaks the wrong motivation.

Unless we're talking about a breakout success like Google or Facebook, the CEO and the founders get almost all the fame and glory. A few VPs get decent exit options, and retention packages to balance those. Below the VP level, with a 0.02% slice and with your prospective bosses not liking questions about what preference structure exists against that equity, the startup glory isn't real. Sure, there's open bar at the IPO party, but it's not the same thing. It won't set you up for life.

Also, "making it big" in a startup and not getting a payoff is a bad outcome. I would be fucking pissed if I worked so hard as to bring a startup from scratch to a major exit, only to get robbed by participating preferred and onerous "earnout" shenanigans. Working hard and getting nothing in return isn't virtue; it's waste. The objective function is different in public service or the non-profit sector (where people can work hard without personal enrichment, because they are legitimately serving the world) but startups are just that-- businesses. They exist to make money, and if you don't benefit from one that you started, you've wasted time.

This doesn't mean that startups can't improve the state of the world, but that's not their primary goal or purpose. If you want to improve the world, work for a non-profit or in research. If you work tirelessly to vanquish malaria but never get beyond a middle-class material existence, you've still lived well and done good-- you weren't trying to get rich. If you throw your all into the toughest, most painful, and riskiest private-sector efforts and "make an impact" but never get rich, then you're a chump who got played.

Do you want a guy like this at your company? This is absolutely poisonous from a culture perspective.

Older employees tend to be canaries in the coal mine. They have enough connections and experience that they don't worry about getting fired, and far more importantly, they've been through bullshit before and have seen the worst patterns. The reason older workers don't like to work 18-hour days is that they've done it before (when they were our age) and they've seen that it almost never works. They're more willing to say that the emperor has no clothes.

The problem is that many human organizations (and the majority of dysfunctional ones) bond and judge according to shared suffering, not actual productivity. This creates the culture of working inefficient 18-hour days instead of focusing intensely for half that time and then going home.

After all, you've got your wife and kids, and startups are all stupid scams meant to bilk the coders, so why feel excluded from anything?

That's not what he's actually saying. I am not two-thirds his age, however, and will say that this accurately describes the majority of the current crop of VC darlings and bubble startups (but probably not the majority of all startups). Now is not a good time to join a "hot" startup, unless at a VP level or higher. Real Technology is different (you'll learn a lot) but I'd advise everyone to stay away from "social media" at non-executive levels until the bubble clears.

The reality is that startups are businesses. As with large companies, some are good, some are bad, and most are in-between. Here's the rub: When people join others' businesses, they expect that the people directing their work will take an active interest in their career growth (and, if they're savvy, move on when this doesn't happen). In a startup, this would mean letting the new hire have investor contact and architectural influence, and also (and this one's rarely done) providing some kind of insurance against having people hired above him. Large companies have a lot of problems, and it can be hard to "move up" position-wise, but they actually do better (on average) than bubble startups at investing in peoples' careers, because they're more likely to be around in 10 years.

The problem is that a lot of startups are creating "reality distortion fields" that lead a lot of people to think the rules of "the real world" don't apply. So they take offers at 50% of market salary in companies that don't invest in their career growth in exchange for equity whose median-outcome value is zero.

What's actually overvalued in 2012 isn't startup stock (most of which isn't publicly traded). I think that's fairly valued (meaning that these "obscene" valuations actually reflected the EV of the company's performance, although the implicit promises of growth are bunk). What's overvalued are subordinate positions in startups. A lot of young people are taking them thinking that they're going to get the "startup experience" when, for most of them, they'd do better to join more established companies with better laid-out career paths and, on the whole, more competent management.