You've said how you plan to spend money, but not how to plan to make money.
I'm pretty sure that back when I was choosing a university I'd have said that such a service would be good but wouldn't actually pay for it. Paying for information on the internet is a weird and alien thing, especially if I didn't know in advance how high-quality the information was (I'd just have to use heuristics like "most adverts on the internet offering information in exchange for payment are somewhere between not worth it and outright scam", or "websites with a z in the name are shady").
I agree about people's reluctance to pay for things on the internet. For that reason, I think I'd make money via advertisements. Judging by the size of my competitors (College Prowler, Unigo, Cappex, Princeton Review...), that seems like a sufficient way to make a lot of money.
Regarding the 'z', I don't like it either, but the guy who owns the 'collegeanswers.com' domain wanted $10k for it because it was "in development" (which is bs because since the summer when he told me, it hasn't become a site). I don't even have that much money. I've thought about a bunch of other names, but decided on 'collegeanswerz.com'.
My motivation behind this post stems from Aumann's agreement theorem. It seems that my opinions on startups differ from most of the rationality community, so I want to share my thoughts, and hear your thoughts, so we could reach a better conclusion.
I think that if you're smart and hard working, there's a pretty good chance that you achieve financial independence within a decade of the beginning of your journey to start a startup. And that's my conservative estimate.
"Achieve financial independence" only scratches the surface of the benefits of succeeding with a startup. If you're an altruist, you'll get to help a lot of other people too. And making millions of dollars will also allow you the leverage you need to make riskier investments with much higher expected values, allowing you to grow your money quickly so you could do more good.
A lot of this is predicated on my belief that you have a good chance at succeeding if you're smart and hardworking, so let me explain why I think this.
Along the lines of reductionism, "success with a startup" is an outcome (I guess we could define success as a $5-10M exit in under 10 years). And outcomes consist of their components. My argument consists of breaking the main outcome into it's components, and then arguing that the components are all likely enough for the main outcome to be likely.
I think that the 4 components are:
The Idea
Your idea has to be for a product or service (I'll just say product to keep things simple) that creates demand, and can be met profitably. In other words, make something people want (this article spells it out pretty well).
What could go wrong?