You Don't Have to Ditch the Day Job
Editor's note: This column is adapted from Wright's recent post on his blog on running a sustainable Web business.
In the beginning, it's not always practical to dive into a Web startup full time, though eventually you will have to if you want it to succeed. Still, if you're too poor or too unsure to do the right thing for your business and dive in full time, here are a few things that seemed to work for my partners and me when we did it part time. Some of the tips will work in almost any industry. A few will really only work in a Web business.
1. You need a co-founder and some cheerleaders. If you can't find two or three friends who are really excited to be beta testers for what you're building, consider changing direction. The arguments for a co-founder are many and varied. For a part-time effort, they are essential to keep you on track and working. At some point, you'll hit a motivation wall. If you have a partner who is depending on you, you will find a way past that. If you don't, you'll often lose interest and let the project fizzle.
2. Pick a day or two per week when you always work, ideally in the same room as your co-founder(s). I repeat, always, no exceptions. We did one weekday evening and one weekend day. That doesn't mean we weren't working other days, but having a fixed schedule helps you through the phases of the project that might not be so fun.
3. Have a boat-burning target. What will it take for everyone to dive in full time? Five thousand active users? 10,000 uniques a week? Funding? That should be a shared understanding. You don't want to have one founder ready to go full time when another has reservations. This is easy to gloss over, but you should really nail it down. I've lost two co-founders who weren't ready to dive in full time when I was. It wasn't fair to them and it wasn't fair to me.
4. Pick an idea that is tractable. Every business is a theory. If your theory is "We can build a better Web-based chat client," that's something you could test quickly. If you're theory is "We can build a car that runs on lemonade," that's just not going to work as a part-time effort. The scarcity of available time should force you to distill the idea to the absolute essence that is necessary to test the theory. No extraneous features!
5. Understand that your first version is probably going to suck. Read Weebly founder David Rusenko's post on persistence. It's a long road. My first startup was a ridiculous fluke. I ran it for two months, then sold it. But almost all of the overnight successes you read about were slogging in the muck for five years before the night in question. Be prepared for a long journey and be surprised if your startup is an immediate hit. So with your first version, look for the tiny little flicker than you might be on to something to motivate you to make it better. Every week, make it better than last week and see if that flicker of light can be fanned into a tiny flame.
6. If you're going to screw off at work (everyone does), spend it getting smarter about the stuff you don't know. If you're a coder, read a few design/usability blogs. Read up on what motivates angel investors. Research competitors and write down what they do well. Get brilliant at SEO, search engine optimization (it's not hard). Write a lot more (blogging helps). Think about virality and research the heck out of it. This is all more valuable (and hopefully just as fun) as looking at LOLcats on Reddit. Having said all that, do be aware of the fuzzy line between using your cooldown time at work for your startup and stealing time/resources from your employer. If you're paid to do a job, you need to do it.
7. Be sure you own your startup. (I added this tip thanks to Ivan's comment on my blog.) I've had the fortune to work in places and companies where there was very clear ownership of "after hours" work. If ownership of your personal intellectual property is not clear, do not rely on the goodwill of your employer. Greed can do funny things to people, even if they were initially big supporters of your startup.
At the end of the day, you want to prove whatever you need to prove as quickly as possible, so you can dive in full time. Near as I can tell, there are plenty of startups that have started as hobbies, but you need to move past that phase as soon as you can. There is nothing that drives a team forward like the fear of public failure, debt, and starvation. Leap off the cliff and start building the airplane on the way down, and you might be surprised what you can pull off.