Should I work at a startup?
January 23, 2012 8:43 AM   Subscribe

Is it worth it for me, a software developer with over 15 years' experience to work at a startup in order to update my skill set?

Looking at the job market in Toronto, there seem to be two classes of jobs I qualify for: maintaining legacy code at large businesses or working at brand new startups where they're looking for someone who can learn whatever cool new technology they're working on. Everything in between lists some "must have" technology that I don't know anything about. This is worrying because it signals to me that I'm not keeping my skills up to date. My background is in development tools and low-level stuff with a smattering of Perl and Python. I'd like to get into mobile apps and/or cloud services.

Because of this, I'm considering looking for a job at a startup and have managed to get an offer. Assuming the worst case and I'm
underpaid, overworked and the whole thing tanks in a year and a half, I figure that having the new skills on my resume will be worth it in terms of job opportunities.

On the other hand, I'm in my early forties and plan on starting a family soon. I'm really too old for the over-caffeinated lifestyle.
The pay cut certainly wouldn't help me save for retirement either.

So my question comes down to, are the potential skill gains worth taking the loss of income?

posted by anonymous to Work & Money (6 answers total) 7 users marked this as a favorite
Almost every big company has an "innovation" or "skunk works" group that explores these new technologies while still offering decent benefits, at the expense of dealing with more big company stupidity than you'd face at a startup. Sounds like that might be the right opportunity for you -- it's probably worth getting out to industry events to network around these things, as many times these positions are hired more socially instead of being regular "send us your resume" gigs.

Also, as you'll undoubtedly hear everywhere, dive into some open source projects and submit code and answer questions; Regardless of which path your career takes, you'll want to prove your credibility in these new platforms with your Github and Stack Overflow profiles.

In short: You won't go to a startup to learn these new skills. You'll learn these new skills to go to a startup. If you don't have kids yet, then you have time to be hacking on weekends and evenings to get up to speed. Once you do so, the sky's the limit.
posted by anildash at 8:47 AM on January 23, 2012 [6 favorites]

I like anildash's advice.

Though I don't come from a programming background, I've been spending some time teaching myself Python. My intent is not to become an uber-programmer but rather to develop some sort of skillset with which to relate to programmers/developers and other key people in startups.

(My background is in finance and operations.)

This allows me to, for example, go to a networking event (I live in NYC), and talk to a guy who's building a web app, let's say, and actually ask him some coherent and concrete questions about what he's doing, what sorts of problems he's having, and relate to him on his terms.

So, you're already miles ahead of the game by having years of software development. Just because you have used whatever the language du jour is doesn't mean you can't have good conversations with others.

Does Toronto have co-working spaces? If you were in NYC, I'd tell you to go to General Assembly (not the Occupy Wall St. thing) and hang out there and meet people.

But, it's less about the skills you don't have and more about developing new skills and using the skills you do have to your benefit.
posted by dfriedman at 8:59 AM on January 23, 2012 [2 favorites]

I'm doing the same thing as dfriendman, although I do harbor fantasies of actually building something online someday. In the meantime, I'm the rare sales guy that is comfortable on the Linux command line.

I think taking the start up job to lean X is fraught with danger. Given the pace of life in all the start ups I've worked in, you really won't have time to learn on the job. You'll be learning at nights and on the weekends. And if you are going to do that, you might as well do that while staying in your stable, well paid job.
posted by COD at 9:18 AM on January 23, 2012 [1 favorite]

Agree with all of the above. Learn the new skills on your own. Also, if there are lots of startups around, some of them must turn into more established companies, right? Once you pick up the skills that companies you're interested in seem to need, maybe you could figure out what companies are around that are in between the giant corporation with piles of legacy code and the startup where you're working around the clock on cool new stuff.
posted by chickenmagazine at 9:26 AM on January 23, 2012

In my (20+ years) experience, startups are willing to pay more than I'd make in an established company.

Maybe I'm unusual, but I don't think so. Startups are desperate for good programmers, and will pay top dollar to get them. Less politics and less history make this easier than it would be to make top-flight money at a big company. To me, top-flight programmers should make between $100-$250K per year, depending on specific location and talents. Never less than 6 figures, though. I've literally laughed and walked out when offered significantly less than 6 figures.

My number one disqualifier when considering a gig for a startup would be for the company to try to lowball me. "You have these great options, which you might make a killing on." Thanks, but no. Pay me what I'm worth or I won't take the job. I'll still take the options, but I want the pay. Thats what I tell them, and I get paid what I want or I don't take the job. I usually get the job at or near the pay I want. Yes, that is quite arrogant. The fact is that my arrogance in this area pays me more money than I'd get by being humble, so I am situationally arrogant. (Hopefully, in other areas, less so.)

Desperate companies pay what it takes. Startups are almost always desperate. Treat them that way, it works wonders. You have to be hard-core about this, or you'll never get it.

Yes, develop your skills and resume to be able to pull off that attitude. No, don't take a pay cut for a company which will almost certainly tank, with its options worthless. Open source rep helps a ton. Rep is earned, it may take a while.
posted by Invoke at 2:43 PM on January 23, 2012 [1 favorite]

: "
So my question comes down to, are the potential skill gains worth taking the loss of income?

Perhaps the question you should be asking is "How much longer do I see myself in a programming role?" We both know the field is ageist and kind of incompatible with family life as practiced. If you figure in another decade you'll be climbing the managerial ladder, then it's time to start looking at how to get a leg up.

So how does working for a startup get you into say the management path? Well, there's a lot less specialization, so you'll have a broader experience. There's the potential to become a hiring manager as the startup grows, but if you're discounting the options as worthless then you're also writing this off, and I'm told many startups have to "promote their founding employees out of the way" as they become unable to manage the organization beneath them.

On the other hand, if you're dead set on coding to the grave, I figure you'll need some small business / independent contractor skills, and know where to look for clients. A startup might be a good place to acquire this, and learn what does / doesn't work on someone else's dime. Just make sure to vet the startup just as well as they vet you. A friend of mine took up an offer I passed on and three months later paychecks started bouncing.
posted by pwnguin at 5:39 PM on January 24, 2012

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