* First off, doing a startup is not just about sitting in a dark room and writing code without a boss. It isn't even mostly about that. Your average engineer has no idea how much non-technical crap there is to do, and consequently has no idea that the things they like to do don't strongly overlap with the set of things they think they'll be doing as a startup founder. It isn't just pizza and coding sprints -- it's about talking to customers and coordinating with other people and marketing and finding photos and making spreadsheets and raising money and bookkeeping and filing idiotic paperwork with bureaucracies and diffusing personality conflicts and a million other things that good developers never think about and don't ever want to do. And if you succeed, your reward is more of that stuff and less coding.
* Second is that you'll work like crazy and have to bear a lot of stress. That's the way it goes. Most people aren't cut out for that lifestyle. Doe-eyed college graduates, especially, haven't ever done a project that lasts more than a semester or two. They have no idea what they're getting into.
* Third, if you don't have a co-founder, and you don't have any experience, you're doomed. Go work for someone else for a while. I know, I know...$FAMOUS_PERSON did it. They're the exception, not the rule. If you're in that situation, there's a litmus test: is your product currently built and exploding in popularity? Then you may be the next Zuckerberg. Otherwise, go work for someone else for a while.
* Fourth, these days, most people confuse "doing a startup" with "making a cool feature". They're not even close to the same thing. I can't tell you the number of resumes I've seen from developers who made a half-baked marketplace website that they called a "startup", then gave up when the users didn't come and they realized that 99.999% of the work was ahead of them. Building the product is the first step, not the last one.
* Fifth, just because it's cheap to rent server space and open-source means that you don't have to write CGI by hand doesn't mean the competitive landscape is easier. In fact, it's harder. For any idea you come up with, there are either 50 sophisticated, me-too competitors, or there will be within 10 minutes of you getting any publicity. The flip side of everything being cheap is that any bozo with a credit card can do it.
...I could go on and on with this. Point is, most developers have this hazy, romantic, idyllic notion of "doing a startup" that bears no resemblance to the actual thing. Communicate this honestly and clearly to someone when they're waffling between taking a job and going off on their own, and you've got chances. After all, anyone who's really ready to do a startup isn't going to be talking to you about a job. They're going to be doing a startup.
And it is not that difficult for decent developers to create such a life-style business. Certainly, no where near as hard as you suggest creating a start-up is.
Such lifestyle businesses might include a SaaS, a few iOS Apps or a consulting business. I have such as business myself. And I know personally other developers who have done the same.
Lifestyle businesses don't have to be hard. They don't even necessarily require you to speak much to customers (if your products are games in the app store, for example). And you really don't have to work that hard, if you don't want to.
You only have to work hard if you create a business that makes you work hard (ie bet on winning big with dollops of VC cash). Try creating a business that doesn't require you to work hard, and you may - surpise, surprise - find you don't actually have to work that hard.
Actually, that's probably the most naive of the romantic notions of doing a startup. First of all, the things I described apply to businesses, not only VC-backed startups. Just because your company is small doesn't mean you're suddenly immune from talking to customers and dealing with bureaucracy. If anything, you spend more time talking to your customers when the base is small, because everything is so much more precarious.
Second, the number of "lifestyle businesses" that exist as single-founder-tech-guy-and-a-computer are so vanishingly small as to be unicorns. The people who claim to do that are either secretly making most of their money doing consultancy (which is fine, but it ain't a 4-hour work week), or they're in such a bizarre niche that they've built a knowledge and/or distribution moat around their business that is virtually impenetrable, through years of backbreaking work. Your example of "app store" developers is particularly on-point: it's notoriously rare and difficult to find a product that has a sustainable business model in that marketplace.
Law of the universe: if you want something, there are millions of other people out there who want it just as much as you do. Any business opportunity that is simple enough to be achievable by a relatively unskilled single-founder-with-a-computer, yet lucrative enough to support that founder indefinitely with a four-hour work-week, will invariably attract competition from the undifferentiated masses who don't want to work, either. So you're either competing with those people (hard) for a small pie, or you're trying to build a growth business in a large market (hard), or you're failing (hard), or you're getting a good job (hard). There's no free lunch.
There is the problem of telling whether there's a market for a given thing before you invest six months or a year building it, so I'm not advocating sinking a whole year without shipping, but there's definitely merit to starting with something that can't be built as a rails app.
Small businesses, at least in the UK, do not involve that much bureaucracy. You hire an accountant to deal with that.
And, seriously, you don't need to put back-breaking effort in for years to create a (non-consulting) lifestyle business. I used to work with a developer who coded a niche social network on the train to work each morning. The site now makes him far more than he ever did working as an employee.
There are plenty of other niches where developers can make good money. Competition does not work like you think - it is nowhere near as intense as you seem to think and, regardless, there is room for more than one player even in a niche market, if all you are aiming for is a lifestyle business.
Sure, there is no free lunch, but it ain't anywhere near as hard as you are trying to make out. Other readers, don't let this guy put you off setting up on your own.
The "person" described here in the parent to your first reply:
"Or startups in general. You're competing against the awesome developer doing their own thing."
With regards to that even "awesome" people make foolish choices all the time. It's up to the person trying to recruit the described person to give them, in plain terms, what's involved in doing it all yourself. My guess is that they don't do a particularly good job at this. Nor does the entire startup community either other than to make generalizations about difficulty and how most ideas don't work. But we're talking about the same community that thinks it actually makes sense to pass on Harvard acceptance and do YC.
Most lifestyle business are full time jobs, just not ones where you have a chance exiting with 20 mil in the bank.
There's nothing stopping people bootstrapping their freelance business into small digital agency if they want to expand.
I think that notion is actually, more often than not, "doing a lifestyle business." People tend to get confused--I think because they're both talked about so often on HN--and connect the excitement of the startup scene, with the four-hour work-weeks of "hands-off" B2SMB businesses like Patrick McKenzie espouses.
I think, if people took a hard, rational look at their own desires, they might realize they are okay with less excitement and more four-hour work-weeks. You can do hackathons and contribute to OSS in your spare time if you still feel an urge to be speep-deprived ;)
I remember reading a case study about two different brands of water filters. One was, on paper, clearly superior (removed things that demonstrably cause illness) but removed a mineral that made water "taste good". The other, inferior filter brand, left that mineral in the water and thus beat taste-tests hands-down.
The study was about the immense marketing challenges that the superior brand had in turning around the perception (as I recall, they had to tweak the filter to enable pass-thru of that mineral, then run taste-test switch ads).
Anyway, the point is the same - yes, it's really really hard to actually get a company off of the ground. But none of that matters if your candidate hasn't tried it once or twice: you've gotta find ways to neutralize that argument.
I like the one where "If you want to leave here after a few years we'll give you xx-thousands of dollars" - because the great work environment, combined with now an inside view of just how hard a startup is - they probably don't get very many folks taking them up on that offer.