A Less Risky Path to Entrepreneurship in Software Development

I'm confused what the point of this is - is it that if your startup fails you have something to fall back on with a 'real' job? Makes it sound you can become a developer and magically your startup has much more of a chance to become spectacular - which is of course bunk.

What kind of "ruin your life" failure do you think people on HN are at risk of undertaking? It strikes me that such levels of failure are very rare, at least among the set who even knows about HN in the first place.

A lot of these startups are pretty ugly when they let people go. Banks and hedge funds and large companies lay people off, but they're honest about it. They say, "we had to cut jobs", and they usually pay a decent severance. Many of these startups make those look like performance-based firings in order to save face. Needless to say, that practice creates a lot of ugly behavior on all sides, and you don't want that stuff to follow you.

A "for cause" firing (which invariably comes with no severance, and can have reputation effects, because for those words to come up on a reference check is devastating) can really fuck up your career. Also, there are a lot of venture capitalists out there who have no problem breaking with common decency and doing a "back channel" reference check.

That's one risk. There's more variance in startups, so the good outcomes are a lot better, but the bad outcomes are really nasty. I know people who've had ex-employers throw frivolous lawsuits at them, just to be vindictive, years after the fact. That kind of nonsense doesn't happen nearly as much in big companies.

More relevantly, a lot of these startups don't do much for a person's career, as there's a lot of junk work to go around that you won't learn much from. If you get into your 30s and 40s and haven't worked on a couple of serious, meaty projects-- and a lot of people haven't-- then you start facing the age discrimination issues. I think those are probably mild for people with legitimate work experience, but the people who did lots of low-yield grunt work "because it was needed" and without appreciation are just screwed. You have to manage your career, and if the work available isn't benefitting your long-term employability, move after 12 months. But... that gets me to another risk: the job-hopper stigma. It's pretty typical in the VC-funded startup world to have more than one job per year, but it looks really bad if you want to go to back to traditional companies, and you might not slide back in on the best terms.

Unfortunately, the reality in careerist America is that age matters a lot, so you have a lot less time than you think you've got. It shouldn't matter, because what really matters is how much time one has left, and a lot of us will live into our 90s (or later, if the most optimistic people are correct) and be sharp until the end. However, the sad truth is that age does matter, and you have to manage your career pretty aggressively to avoid looking like an underachiever amid the harsh age-grading of hyper-optimistic tech companies.

US employer here (who all hires for some EU-based roles): I view failed entrepreneurs very positively, assuming the candidate can reflect reasonably on what went well and what went poorly.

PS: you probably mean stigma, not stigmata: http://en.wikipedia.org/wiki/Stigmata

I think it varies quite a lot across countries. I don't think it would be a problem being a failed entrepreneur in the Netherlands.

I had two belly flops, two marginal and one boring startup under my belt before I took on the latest one. I have never met any stigma in the Netherlands, UK or Sweden. The last two are of course not mainland Europe, but anyway.