I had the day off today, which gave me with some much needed time to think about what project to work on next. I finished Simply Rails 2, which has given me a foundation for starting a Rails application. There’s a lot I don’t know, but I feel like I’ve got a good enough foundation now that I should just go for it and learn along the way. It’s time to just do it.

There are four projects I’m considering and I haven’t been able to decide which one to pursue. So I headed to Barns & Noble and spent a few hours there this afternoon writing about the pros and cons of each project. There’s something about the atmosphere in book stores that I find very conducive to thinking, writing, and of course, reading.

Making the decision is tough and I don’t want to make it hastily. I didn’t put enough time into thinking about my last project, ALL IN Expert, and realized after I launched that there wasn’t a market for the product I had just spent three months developing (more on that in another post). For this one, I want to spend my time working on something that has potential to be big.

Armed with an asiago pretzel, some tea, and a notebook, I set to work detailing the pros and cons of each endeavour. I spent several hours there, doing this, perusing their selection of Rails books, and talking a 75 year old small business owner named Dave about politics and business. At the end, I still had no idea which project to go after, but was a little bit closer ;)

Dave was an interesting guy. A little overweight with thick white hair, I saw him reading Michael Moore’s guide to the 2008 elections and started a conversation with him. He told me that McCain had just picked a VP and we discussed the merits of his choice for a while. I don’t know much about politics, but I find other people’s opinions fascinating, especially when they are passionate. When that conversation died down I asked him what he did, and he said he was a business owner.

He was a minister till 40, then got into the wholesaling crafts and eventually jewelery. He traveled to Mexico a lot for the crafts, but eventually determined the margins were too small and the inventory too large, so he transitioned into jewelery. He’s been to Tailand, which apparently is a big jewellery hub, many times, but he said in recent years because of all the travel regulations he had to stop. I guess its harder to just carry $15K worth of jewellery into the United States these days. Anyway, I asked him if he had any advice for an entrepreneur and he said above all else, “Be dogged“.  He said you’ll run into a lot of problems along the way and you just have to take the hits and keep going. He said once a guy wouldn’t pay him $5K that he owed him from some jewellery sales. So, Dave went to the guy’s house and sat in the guy’s driveway till he came home. The guy, who had been at a casino, was furious when he got home. He got out of his car, cursing and threating Dave. Dave explained politely to the guy that he wanted his money and wasn’t going to leave until he got some. He said he got some of it that night and eventually got all of it. (This is Jersey – was Dave a mobster?) When he left he wished me luck. Nice guy that Dave.

Anyway… moving on…

Later on while browsing HN, I came across angelsoft.net, a site that helps link entrepreneurs with angel investors. One of the sites led me to an Executive Summary template for companies seeking an angel investment. Here’s my summary of each section on the template:

1. Business Description – quick summary of business including product, vision, and business model

2. Management – why our people are going to kick ass

3. Company Background – what problem are we trying to solve and why

4. Technology/Proprietary Rights – what hurdles do we have to overcome to get our product out

5. Marketing, Sales and Customers – who is our audience and what are the current trends in your market

6. Competition – where do you stand and what will set you apart

Then it asks about some of the more technical aspects of the company including:

* Type of financing sought

* Pre-money valuation

* Professionals (account firm, corporate legal, IP, bank)

* How you will use your funds

* What type of entity (S Corp, C Corp, LLC…)

Part of me says not to start working on something that wouldn’t make a legitimate business with a clear source of revenue. The other more persuasive part of me says don’t worry about that, just get traffic and worry about the money later. I think whatever I wind up doing will probably have a freemium business model, which is a great compromise which has worked well for a lot of web 2.0 companies.

I’m going to relax a bit this weekend, which’ll hopefully provide the clarity I need to make a good decision.