Startups and Simon Legree


What would the internet be without passionate arguments? The latest tempest in our corner of the online universe was kicked off by Jason Calcanis, who published a blog entry titled “How to save money running a startup (17 really good tips).” A bunch of these tips were the sort of things we’ve recommended ourselves: second monitors and good chairs for developers, use Google Docs and hosted email instead of Microsoft alternatives, allow flex time. But one of his points triggered howls of outrage in the blogosphere (original wording below):

Fire people who are not workaholics…come on folks, this is startup life, it’s not a game. don’t work at a startup if you’re not into it–go work at the post office or stabucks if you want balance in your life. For realz.

There was a bit of a pileup on Calcanis for that sentiment, with TechCrunch and other outlets portraying Calcanis as a modern-day Simon Legree. The folks over at 37signals even published their own list of reasons not to hire workaholics, based on the thought that focusing too much on your work is unhealthy. In response, Calcanis watered down the original controversial point a bit, and posted another blog entry justifying really hard work.

What we’re seeing here is largely a clash of two cultures, I believe. As someone who has been variously a workaholic and a slacker at various points in his life, I no longer find those labels very useful; they’re mostly just ways in which people stereotype and try to cut off debate. In some circumstances (such as being involved with a promising startup) it’s easy to make working long hours a priority because the work is exciting and the potential payoff is huge. At other times, non-work parts of life come to the fore, and work has to take somewhat of a back burner. There’s no magic formula that says “this is the perfect work-life balance for all people and all times.”

As web workers, we’re in a better position than most to resolve this dichotomy in our own lives. Many web workers have the flexibility to turn the computer off entirely, or to arrange work in a “bursty” fashion that combines high intensity with plenty of time for other things. Based on my own history, being passionately involved with your work need not be a negative experience. There’s a surface similarity between working long hours for a startup and being involved in a deathmarch development project that has you sleeping under your desk to meet some arbitrary deadline, but the team attitudes and potential rewards make it easy to tell the two apart.

Startups aren’t for everyone. But if you’re involved in one and finding it rewarding, even though you know you’re being encouraged to work long hours, then there’s no reason to feel guilty because someone on the outside labels you a workaholic. And for web workers, there’s no reason to feel guilty about taking advantage of the flexibility we have to work strange and (when we want) long hours. Figure out what works for you and go with it.



On the other hand, DHH (David) is an engineer, so he knows how an Engineer feels. Just like Joel Spolsky. That’s why you heard different opinions from DHH and Spolsky than from Arrington, Jason and Scoble.


See, the problem here is that all these Executives that do all the talking, not the Software Engineer that actually does the working.

Maybe someday you should ask the Software Engineer to express their feeling instead of these Executives who just want to know that “everything should be done by deadline X”

rick gregory


But there’s a difference between maximizing effective output (quick, measure that) and emphasizing hours worked. The latter is too often seen as a proxy for the former. Oh, you’re not here at 8am and leaving at 10pm? You’re deadweight.

Having people work long hours can also let management avoid asking hard questions about whether something should be done… everyone’s working 80 hours, so you have more hours to play with right? But are they working 80 hours because you’re just in that mode – to do everything you NEED to do it takes that much effort to succeed – or have you started out with the assumption that you have people for 80 hours and let tasks expand to fill that time?

It’s just as important to know what NOT to do as to get things done.

Tony Wright

I guess I’m ultimately “pro-Calacanis”, as much as it pains me to say it.

All of the “work/life balance” people are speaking from the comfortable perspective of being either profitable or heavily funded.

If you’re in a fresh startup with and bank balance moving rapidly in the wrong direction, you’ve effectively jumped off a cliff and are assembling an airplane on the way to the ground. Presumably, you want similarly motivated people with you… That means MAXIMIZING EFFECTIVE OUTPUT. Period.

And no, working 14 hours a day 7 days a week is NOT generally a smart way to maximize your aggregate output– you’ll burn out. Each person in a startup needs to understand their own style and brains enough to find the “sweet spot” of effective output and charge forward.

Mike Gunderloy

Well, that’s part of my point, Duncan: I don’t think *either* calling those who are deep into their work “workaholics” or those who spend some time outside of the workplace “slackers” is a really useful part of the discussion. Talking about actual behaviors rather than throwing around labels tends to raise blood pressure less and move us closer to common understanding.


It’s interesting that you dropped the work Slacker, as this is the label the pro-Calacanis people are using. Someone who wants balance can also be a hard worker, the opposite to workaholic is not slacker, there’s a variety of shades in between. I work long hours, probably not best for my health (others have called me a workaholic) and yet I endevour to have balance every day, from taking my son to school, a walk at lunch time, attending the odd school events, playing Wii with my son, going on the odd outing, none of that makes me a slacker and I’m furious that others would use that label.


David at 37Signals made some really good points. No matter what situation you are in – a startup or an established organization – balance is needed.

I agree here though. Long hours can be a good for a short period when trying to meet a specific goal (‘bursty’). But I think the best thing is to recognize when it’s time to cut back and make other things in life the priority.

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