Starting The Web App Challenge: From Zero to $5,000/month In 6 Months

My suggestion for ideas - make simple tools for team/organizing for normal people. Not yet another collaboration/project management suite but apps to help teachers, baseball coaches, and scout leaders. My free tool http://chir.ag/projects/team-maker/ ↗ gets over 10k hits per month, mostly via Google search and a single MakeUseOf post. I did no advertising and yet I get emails every other day from someone trying to do more with the tool and offering me money to build a pro version.

Another free app of mine that does great is https://zetabee.com/icaljs/ ↗ - it's a simple calendar that takes an iCal feed and inserts it into your website via JS and lets you style it with CSS. People have written me many times to make that into a more feature-rich app and charge $x/mo for it. I'm still busy with my KType project (that we emailed each other about a while ago) so I'm not in a good place to build these apps but you might be in a much better position, especially with your awesome marketing skills. Patio11's found success with apps for normal users too. So definitely consider "simple tools to make someone's life super-easy" as a viable candidate.

I took on a very similar challenge in 2012 although I gave myself a year to do it mostly because I didn't have the benefit of market penetration to validate my idea before starting. Because I'm a developer I started with my idea, then went after the market which I think may have cost me a few months in the beginning. I also very much under estimated how slow the real estate market is to adapt to new technology so I didn't fully reach my goal but I'm 2/3 of the way there and think I'll get the rest of the way plus some in Q1. I really wish I had of documented the journey the way you are. It would be a super valuable retrospective. Maybe I'll do one of those fancy year in review blog posts that all the cool kids seem to be doing.

I think it'll be important for you to learn as much as you can about RoR so that you can accelerate to launch as quickly as possible and start getting those clients in the door. Anyway, good luck with reaching your goal!

Getting a successful web app is tough, why add unnecessary constraints to make it harder?

One example is "I can only spend $5,000 of my own money in this entire process". If you could get an awesome programmer for $6,000 to build the whole thing, would you really say no just to stick to the arbitrary rules?

I think you need to go into a startup with the idea that you need to overcome all the obstacles that get in your way, not start with some arbitrary obstacles to make a game of it.

Good luck, but I think you are making a tough task even tougher, and unnecessarily.

I started writing a RoR application at the beginning of December, my first application at that. I'm a PHP developer by trade however for the type of app I'm developing Ruby and the Rails framework is better for me.

I too am Bootstrapping my project but with only a little, not $5000 but it can be done. Costs are: domain, Heroku/AWS hosting and advertising.

SaaS seems to be the route everyone is taking with these kind of things. Bring in the UK makes this harder though, no decent payment providers such as Stripe, so I'm going with Paymill.

Best of luck Nathan!