This is a decision with consequences. Managerialization is kinda like going from amateur to pro in sports. On the other hand, keeping amateur status, doing it all yourself, or with a coop of others who primarily write, with some automation has non-obvious advantages.
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The biggest problem with outsourcing "uncreative" tasks to non-robots (or people who you don't have to deal with personally, behind a SaaS service) is that you are in relationship with people with different incentives. Two examples.
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First, some guy emailed me excitedly a while back offering to rep me to look for and win good advertising deals for "quality content sites like yours." Unlike generic overtures like for low-end ads (which run $50-$100/mo on high traffic pages) he seemed like a sports-agent type.
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I said sure, I'll take a call. He seemed like a nice guy, with a decent track record doing this for other sites. But when I shared my traffic stats with him (just shy of 0.5 mil visitors/year at that point, same as now) he sounded deflated and I never heard from him again.
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A bit of research revealed that the represented ad sales for blogging by anybody who actually knows how to do the job, requires an incentive structure (commission based) that only works north of about 2 million visitors/year. To get there, I'd have to prioritize viral clickbait.
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Second example. Early on (like 2008) I briefly hired a guy off odesk (now upwork) to do promotion for me -- post comments on other blogs, do some tweeting etc. Nice kid, who tried sincerely, but in 2 weeks it was crystal clear it was the dumbest idea in the world.
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Incidents like these, together with some thinking led me to a conclusion. If you want to hire people to do the boring parts, you need a proper magazine-style business model that can support people with different risk appetites and compensation expectations.
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now that I think of it, magazine style business model and magazine style CMS go hand in hand at some level (perhaps not at .5m/year?)
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which is where “some guy” would have wanted you to be when he contacted you.
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Exactly. Otherwise he can't get the return he needs at a commission level that I would accept.
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Which points to another interesting facet - WordPress is so encompassing that someone looking at a professional enough site doesn’t know if there’s a human infrastructure behind the operation at the scale they need to get their ROI. Alexa website stats only go so far.

