I know that seems like a "how do I cope with my spoil of riches?" type question and I apologize in advance for being the type of amateur class that for all I know has a popular tumblr blog dedicated to making fun of it. I feel like I have thoroughly read the ideas and technical cofounder tags; there are many great questions and answers on how to move an idea to the next level, but they mostly focus on how to evangelize people (developers, investors) to partner with you for later-realized gains. What do you do when you can self fund an idea but want to prepare yourself as best as possible to not flush cash down the toilet, when you have no specific expertise or experience managing a web development project?
About the idea: The idea is for a unique demographic social site innovating a large online community currently in a 1998 organizational model. The idea is framed around a feature set that I imagine would require custom and creative programming. I've sampled a healthy amount of friends and acquaintances in this demographic and have received overwhelmingly positive and encouraging feedback. I've poured through the community and concluded that there is little chance someone is substantively working on a similar product. I've pledged to myself to move this forward in some form every day, whether it's researching, working on narrative specifications, wireframes, or talking to people. I am comfortable spending between an initial $5k - $15k and further retainer for development, design, administrative training, and ongoing maintenance.
About me: I am a relatively young man with no debt, no children, no long term financial obligations, and a well paying job that I love and plan to keep. There are voices in the cornfields telling me to build this baseball field in my back yard (but not in the sense that Kevin Costner was harming his family with poorer crop yield). I see myself spending nights and weekends managing this operation. After purchasing the extremely clever and available domain name, my technical skills have been exhausted. I have a very pie-in-the-sky business model, and I would not be surprised or upset if this idea ultimately makes me no money. This article, one of the first that I found, brought great encouragement:
A couple sub-questions, if you permit:
Thank you all in advance for any responses and for your participation in this hugely helpful site and Q&A network. If this all is too much, please know that I've not intended this to be a subjective "what should I do?" sort of question that this Q&A frowns upon.
In my humble opinion (IMHO) you have most problems of the wannabe entrepreneurs solved. Creating, developing and running the business should be done by your task force.
An Lithuanian businessman gave me this advice. He had already a few successful businesses. One of his latest business was an online shop for prisoners ! His strategy is to find a tech guy to develop and run the business with significant equity of it (~20 to 30%).
He also explained me that founders who work like nuts to develop their business are in fact the work force of the investors ! So avoid to be the work force and focus on finding a viable and profitable business. This is how you'll convince and keep the best tech people to work for you.
The Lithuanian businessman explained me that it was hard to find the tech guy for his first project, but once it was sold for a respectable value (~30K€), it was much easier to convince a tech guy to start new projects with him or to find partners. It's a snow ball effect.
So my suggestion would be to make sure your business is viable and profitable, then look for a tech guy to develop and run the business with your funding for start. To identify a good tech guy, look at what the guy has already developed, created and so. Then test it by making him build a mockup to test the traction of your web service. Minimize investment, time and risk.
My honest feeling is that if you go through with this, and head this up yourself, you will fail. That is one of the best things that might happen. You will learn a lot and will develop a 6th sense which will help you navigate questions like you currently have.
In your case you need to have a balance of mentors and technical people to help you. Don't rush into working with either. They must be top-notch.
Since you are new with this, it will be hard to get top-notch people to work with you because they want to work with other experienced people.
If you want to be a real entrepreneur, you can do it the hard way and just start tackling and solving problems, whatever they may be. In your project they are finding the right team, getting rid of current team members who are useless, learning about high-level legal implications, figuring out how to build a minimum viable product, then how to market it, etc.
Just start doing and learning. Before you know it, you'll be a confident and great leader of increasingly successful projects.
I added a paragraph about co-founding a company with friends to Founding a Company