I gross just under $10K per month from http://www.letscodejavascript.com , a subscription-based JavaScript screencast for professional developers [1]. It's a full-time job: I put out two new episodes every week, plus a "special" every month that takes quite a bit more effort. That leaves me with about half my time for developing the business. I'm bootstrapping this, so it's just me. I don't plan to hire any employees…
Which conversion step do you think it would be easiest to improve upon? I'm curious, because increasing the rate of free trial signups by 30%, from 2% to 2.6% (which seems like a modest increase), would result in the same number of subscribers as if you were to manage to increase trail-to-paid conversions by the same 30%, from 70% to 91% (which seems like a much more difficult feat). Anyway, I'm sure you know the var…
Here's how I decide what to do next: I have a big 6' folding table in my office that's covered in index cards. On the left-hand side are six columns: what I'm planning to work on this week (the current iteration), the next four weeks of commitments (mostly episode air dates), and any future commitments (such as my Christmas vacation with my family).
On the right hand side, I have five more columns: Attract, Convert, Hygiene, Delight, and Intelligence. Whenever I have an idea for something that I should do, it goes in one of those columns. If an idea column is full (some categories get two columns), then I have to throw out one of the existing cards before I can put a new one in.
All of the columns are full.
Every Monday, I calculate my velocity (Agile/XP-style) based on what I finished the week before. Then I look over my upcoming commitments and move everything that should be done this week into the current iteration. I try to stay about two weeks ahead of The Beast (that is, episode commitments), but I don't always succeed. Still, I have yet to miss an air date.
Then I look at the amount of points remaining and choose an idea from the right-hand half of the table to work on. Sometimes there's one I'm already working on--that goes into a special "On Deck" corner of the table--in which case I just generate story cards from that and slot them into the current iteration. If there's nothing on deck, though, I look over all my existing ideas and pick one.
I pick ideas primarily based on bang-for-buck. Is it relatively easy, do I think it will work, and will it give me useful information even if it doesn't work? But sometimes I pick small things that are bugging me or that I think would be satisfying to work on. Morale's important. And sometimes I choose things that are really big and risky but the time is right to do them.
tl;dr: dart board. ;-)
Here's a picture of the table: http://imgur.com/tmm9TvT