I've been doing the nights & weekends thing for exactly 3 years today (9/11). My project is http://www.obsidianportal.com
We're profitable but I still need a dayjob to pay the bills, so take my advice for what it's worth.
1. Shorter release schedule is always preferable. Like others have said 2 years to launch is a really bad idea. However, my question is: Where did you come up with these numbers? Do you have 2 different projects, or are you setting arbitrary timelines and want to fit a project to that timeline?
2. Going all-in is not a bad thing. I'm currently a "parallel entrepreneur" and it's very hard. It's much easier to focus on a single thing and hit it 100% rather than focus on a lot of things at 20%.
3. Sysadmin is easy: sign up for a service where someone else handles it. As a Ruby on Rails guy, I heavily recommend Blue Box hosting. It's like having a sysadmin on the team, and it's not much more expensive than Slicehost. It's a good skill to learn, but I'm with you: let someone else do that stuff.
4. It sounds like you need an idea. I know everyone says it's the execution, not the idea, but you need _some_ idea to execute on. I would suggest using your time now to try and find 2 things: an idea and a co-founder. Going to local meetups, talking to people, and such would be good things to do at this stage. Find something you can be passionate about, or else you'll never find the motivation to spend your nights & weekends on it.
My original thought process was that it'd be better to pick a long term ambitious project and launch a minimum viable product for it in two years (not a full project like I think I implied in the original post). As you and others pointed out though, I should shrink that even more until I have something that I can release in months, not years.
I have plenty of ideas, but they're mostly, in pg's words, science projects, not company ideas. See, for example, HNTrends.com. Neat idea, but not exactly something that's going to put food on the table.
There's pros and cons to looking for a big idea. If I identify something that I'm passionate about, execute it well, and lady luck is on my side, I'll be in good shape. But, the longer I drag my feet looking for a big idea, the more I increase the chances that I'll miss out by not simply executing a small idea and gradually growing it into something big. All that said, I think your initial direction matters a lot. I imagine many founders have had great ideas that they wish they could execute but they can't because they've committed to something else which is why I'm taking the time right now to figure things out.
I suppose what it all boils down to doing exactly what you said: find something you're passionate about. that'll take care of almost everything else.
I'm definitely not an advocate of "big ideas" but I do think people need to shoot higher than yet-another-twitter-app. There's a middle ground, where stuff like Basecamp sits. Not "enterprisey" but also not just a bullshit re-tweet bot.
And passion definitely won't take care of everything, but it will solve the motivation problem, which I think is the biggest problem that a nights & weekends company has. You still need to find customers and all that, and while passion helps, so too does having a useful, viable product.
I would suggest trying to get outside of the HN geek echo chamber. Ignore Twitter, the iPhone, and all the other hot stuff right now and try to find an area or group that's totally underserved on the web. Ask friends, girlfriends, family, etc. for ideas on things they hate about the Web. In my case, my wife found that small plant nurseries are stuck in like 1996 when it comes to the web, so we started http://doleaf.com Sure, it's not super-sexy, but it solves a real problem for these people, and they're willing to pay for it.
We're profitable but I still need a dayjob to pay the bills, so take my advice for what it's worth.
1. Shorter release schedule is always preferable. Like others have said 2 years to launch is a really bad idea. However, my question is: Where did you come up with these numbers? Do you have 2 different projects, or are you setting arbitrary timelines and want to fit a project to that timeline?
2. Going all-in is not a bad thing. I'm currently a "parallel entrepreneur" and it's very hard. It's much easier to focus on a single thing and hit it 100% rather than focus on a lot of things at 20%.
3. Sysadmin is easy: sign up for a service where someone else handles it. As a Ruby on Rails guy, I heavily recommend Blue Box hosting. It's like having a sysadmin on the team, and it's not much more expensive than Slicehost. It's a good skill to learn, but I'm with you: let someone else do that stuff.
4. It sounds like you need an idea. I know everyone says it's the execution, not the idea, but you need _some_ idea to execute on. I would suggest using your time now to try and find 2 things: an idea and a co-founder. Going to local meetups, talking to people, and such would be good things to do at this stage. Find something you can be passionate about, or else you'll never find the motivation to spend your nights & weekends on it.