Michael and Dave, thanks for the thoughts. It matches some ideas I've got in my head.
Grant, it helps to look at the data problem in more than one part. The first part is historical data. There are a limited number of people who were recording stock data in, say, 2005 - you'd be amazed at how many companies just threw it away because they thought it had no value. There are relatively few players out there who have all the data. They have no interest in giving it away when they can charge for it instead.
The next part is live data. That's controlled by the exchanges, and you can only get access to it if you pay for it. (I know there are a few ways to scrape that data, but they're not reliable enough to trade on - at least not that I've seen).
Another part is data granularity. There are lots of uses for data with daily granularity: understanding the value of portfolios and uses like that. But there aren't a lot of uses for minute-level or tick-level data (at least, not until Quantopian came along!). There's not a lot of incentive for people to invest in creating that kind of data source because there isn't a lot of use in knowing what your IRA was worth at 2:52PM on March 22 - who cares?
Maybe in the future we'll come up with some hybrid model of 1) old data we paid for 2) medium-term data collected and distributed in an open source and 3) live data that we pay for. For the moment, the amount of data in (2) isn't big enough to be useful for us, especially when you can't do live trading without (3).
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