Ignoring the general question of "should more people start companies", some feedback from poking around at your site:
First impression: not a real site. I'm not sure what about it sets that off for me, unfortunately. Maybe the amount of white, the size of the main picture (too small), general non-glossyness, font of the title text, homemade appearance of the logo, and the broken aspect-ratio on the main picture? Hiring a designer can help here.
The focus isn't that clear. As a visitor I can't tell what I'm supposed to be doing. Am I supposed to search for a college? Click on "colleges"? I understand it's about picking a college, but I don't see what I'm supposed to do next.
The "get paid to answer questions" looks a bit scummy and isn't generally relevant. Can you limit it by IP so it only shows up to people browsing to you from those universities? And then simplify it to something like "Answer Questions, Get Paid"? It's also a weird width.
Most of the front page appears to be selling the site. Which you need to do if you're charging for a service, but you're not. Instead you want to get people into the flow of looking at colleges as soon as possible. Save the "what makes us better than everyone else" for an about page or a pitch deck.
Minor: having the questions in a monospace font is weird. As a programmer I love monospaced fonts, but most people don't.
You have an audience issue with questions. You're going for a site where people see answers to real questions, the kind the would ask someone in person if they were socially close and wanted the real deal on a college, but those questions aren't the same for everyone. In particular, there are some questions which probably do matter a lot to some people but are irrelevant or even offensive to others. "How hot are the girls?" was the main one that jumped out to me here.
The comments take too long to load. They're not way slow, but just clicking around some it was distracting having to wait for the spinning C each time. This limits the magic of clicking around and seeing people's responses to questions.
Thanks for the quality critiques!
Regarding the design things, I agree with you. I basically just started learning programming and design this summer and I'm definitely flawed in each of them. I would like one of my first hires to be a designer, but I do think that the current design satisfices (won't wow, but won't draw people away). Do you?
Also, there are some ways in which I think my design is much better than that of my competitors. For example, on http://www.unigo.com/, it takes 2 clicks to pull up a college page (College Guide => type in search) wh...
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?