Sorry for the delay, but here's my pitch: http://www.collegeanswerz.com/pitch . I think it'll enable a more productive discussion of the viability of my website.
Also, check out http://lesswrong.com/r/discussion/lw/jmn/salary_or_startup_how_dogooders_can_gain_more/ .
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Thanks for the response.
All "execution means", is 1) raising the money I need to pay for people to answer questions at all schools on the site, 2) market this to high school students, 3) get enough momentum to raise a series A, and 4) hire the right people to help me expand. At least that should get me to be a player in the market.
I agree that I'm no expert in design/marketing, but I think I could do a good enough job at them to get me to a point where I could hire experts.
Yes. And these are all challenges with significant risks. My claim is that is that it will be hard to build significant momentum prior to getting a level of design and marketing which is significantly beyond your current ability as someone with a programming background. Even if you pay people to provide your site with good content, your visitors will not appreciate that content if is housed in unattractive design, except perhaps for some viewers who find your content so compelling that they are willing to overlook the design.
I could be wrong about this, of course (and your analytics will tell you the answer), but if I am right, then you will need to get help with design and marketing prior to steps 2) and 3). Getting either training, or significant help, or contractors, or co-founders, would need to be incorporated into your plan sooner rather than later.
This seems like an empirical question... and leaving it up to chance sounds like a risky prospect when your money and time is on the line. Given that you admittedly lack experience in design and marketing, it seems like you would be uncalibrated to estimate how much experience in those areas you need to attract funding and co-founders.
To give you some more background about why I emphasize marketing and design so much: in some deals where I've seen companies get funded, a big part of the funding was showing design documents and marketing strategies to potential investors. Also, I often see experienced and serial entrepreneurs worrying about the marketing success of consumer products they are working on. Being scared is a rational attitude given the uncertainty of the mass market and what people will respond to, which is why I'm trying to scare you a little bit about the risks you are facing.
Becoming good at either design or marketing (let alone both) coming from a tech background is at least 6+ months of work to produce non-amateurish work. Perhaps there is some way that you can get help or guidance in those areas in the very near future.