I'm saying that those 3 things are the most likely bad things to happen. Other than that...
A competitor comes a long and outdoes me. Maybe by getting more reliable information by doing research instead of just asking students.
The government passes laws that sway you to just go to your state university, which would decrease the demand for a service that provides information about schools all over the country.
One of the big names sees what I'm doing and copies me.
Something happens that hurts internet advertising (that's how I plan to make money).
I can't raise my seed round because I can't get over the chicken-egg hump of finding an investor.
Students don't do a good job answering questions (they've done a good job for my 3 pilot schools, but maybe those were outliers, and the 297 other schools will have worse quality).
I violate some law unknowingly, get sued, and have to declare bankruptcy.
My site gets hacked because I'm a newb at web development, and I have some security flaw and this leads to my database of answers getting deleted (doubtful because I'm using Disqus to have people answer questions, and Rails to build the site).
Those are obviously only a fraction of the things that could possibly go wrong. However, I've disregarded most of them as so unlikely that they aren't worth thinking about. Are there any in particular that you think I should be paying more attention to (other than the 3 I listed in my first comment)?
I'd want to add at least:
You have to spend more on avertising to get a student to visit your website than that student makes for you in on-site adverts.
It turns out that the existing competition is better because having a large number of reviews in a dozen or so categories turns out to be better than having a small number of answers for a larger number of questions.
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?