I wanted to answer that "things have gotten better" since back in 2000 when I started as an academic who does computation. Unfortunately, I think they have gotten worse. I do not understand why. In fact, this evening I just received the most recent in a long string of rejections by the NSF.
Regarding a company versus taking a job in industry, for me personally there is no point in starting a company unless you have a goal that can only be accomplished via a company, since building a business from scratch is extremely hard and has little to do with math or research. I do have such a goal: "create a viable open source alternative to Mathematica, etc...". I was very clearly told by Michael Monagan (co-founder of Maplesoft) in 2006 that this goal could not be accomplished in academia, and I spent the last 10 years trying to prove him wrong.
On the other hand, leaving for a job in industry means that your focus will switch from "pure" research to solving concrete problems that make products better for customers. That said, many of the mathematicians who work on open source math software do so because they care so much about making the experience of using math software much better for the math community. What often drives Sage developers is exactly the sort of passionate care for "consumer focus" and products that also makes one successful in industry. I'm sure you know exactly what I mean, since it probably partly motivates your work. It is sad that the math community turns its back on such people. If the community were to systematically embrace them, instead of losing all these $300K+/year engineers to mathematics entirely -- which is exactly what we do constantly -- the experience of doing mathematics could be massively improved into the future. But that is not what the community has chosen to do. We are shooting ourselves in the foot.
Now that I have seen how academia works from the inside over 15 years I'm starting to understand a little why these things change very slowly, if ever. In the mathematics department I'm at, there are a small handful of research areas in pure math, and due to how hiring works (voting system, culture, etc.) we have spent the last 10 years hiring in those areas little by little (to replace people who die/retire/leave). I imagine most mathematics departments are very similar. "Open source software" is not one of those traditional areas. Nobody will win a Fields Medal in it.
Overall, the mathematical community does not value open source mathematical software in proportion to its value, and doesn't understand its importance to mathematical research and education. I would like to say that things have got a lot better over the last decade, but I don't think they have. My personal experience is that much of the "next generation" of mathematicians who would have changed how the math community approaches open source software are now in industry, or soon will be, and hence they have no impact on academic mathematical culture. Every one of my Ph.D. students are now at Google/Facebook/etc.
We as a community overall would be better off if, when considering how we build departments, we put "mathematical software writers" on an equal footing with "algebraic geometers". We should systematically consider quality open source software contributions on a potentially equal footing with publications in journals.
To answer the original question, YES, knowing what I know now, I really wish I had started something like SageMathCloud sooner. In fact, here's the previously private discussion from eight years ago when I almost did.
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- Relevant blog post: About Software Development in Companies, Communities and the Academia