When I left the military I had substantial savings to get a startup off the ground and finish a graduate degree.

I decided to write software to help people write better. I always had issues with my own writing as was excited about an extended GNU Style / Diction that could curb my own bad habits.

I created http://www.polishmywriting.com/ as a technical demonstration for my rule engine. I spent the month of June working very long days to write the engine, build the site, and research/import nearly 8,000 rules into the database.

Once I had completed this, I decided to reach out to my friends and old coworkers to get feedback. To my surprise there wasn't much interest. I took this as a red flag about the technology. Without any local validation/support I felt down.

Then I met with some management consultants. Wonderful people! They were willing to work with me through the process of turning the technology into a product. We discussed CMS/blog software integration, a facebook application, and even a tool to aid the workflow for technical writing departments in corporations. With this I felt up.

I took my list of ideas and their tips on how to develop a market study home with me. I looked at the site and how much effort I put into the development up to that point. I then looked at how much effort it would take to go from there to one of the product ideas (plus handling the business side) and nearly collapsed from the anticipated exhaustion. At this point I felt down.

Someone once said that an early startup is full of self-doubt and loneliness. Truer words were never spoken. About 6 weeks in I succumbed to this and it took probably another ~8 weeks before I admitted to myself I wasn't making progress and decided to interview for a position. Thankfully my last semester of school started back up which helped force my hand and restore a sense of purpose.

Anyways, here are some things I could have done to combat the self-doubt and loneliness of my venture:

1) before developing the product, a rudimentary marketing plan would have helped. Even something as simple as visit websites of corporate blogs, analyze their copy, and send them a report of their most common mistakes. I could have then used this as an excuse to get them to signup for a mailing list, take a survey, or even converse with them to gauge interest.

Earlier feedback would have helped me make an informed choice about whether to continue or to dump the path.

2) Make sure you either have a partner or you're well networked with like-minded technical entrepreneurs in real life. I moved to Syracuse, NY and in the summer time it isn't exactly a tech hotspot. We do have a good business incubator here. SCORE and the local business community are good about being their to provide business-sense. I think being around other people doing the same type of thing would have helped provide an example to emulate. This is probably why location is so important. Going through the roller coaster of pursuing an idea is just that, a roller coaster, and having people around who understand it will help.

3) I like to travel and buy nice clothes. My life style while in the military consisted of nearly one trip a month. Traveling was a big part of who I was. When I left I decided to cut out traveling and the occasional fun outfit as unnecessary luxuries. I should have found a way to include these things somehow (even to a reduced extent) so that I didn't feel like I was giving up a large part of myself. Rewards throughout the process may have helped to ease the process. My dad keeps warning me "make sure on your next venture that you're able to support your life style, you learned the hard way that you're not happy just hiding in your apartment playing on a computer all the time"

4) If you're on your own, don't be afraid to hire out certain aspects of the project. When I'm ready to try again, I kid you not, I'm going to outsource everything I can get away with. Doing it all on my own became too daunting. Once I figured out that I could alleviate the workload with outsourcing, I had become risk averse and didn't want to lose any more money. Once I build up my next cushion I plan to accelerate my next startup effort through outsourcing.

Overall, I'm happy I did what I did. I'm sure I had to learn these lessons one way or the other. When I pursue my next venture I'll make sure that:

* I am in the right location,
* I have a network of tech entrepreneurs to reach out to
* I'll market and get potential customer feedback ASAP!
* I'll use outsourcing to my advantage

Good luck!