Someone posted an interesting “Ask YC”, asking:

“How to start becoming an entrepreneur while still being an employee?”

Having done this twice (started a company that eventually turned into a full-time startup), I settled in to reply. Before long, it was clear that my response was long enough to justify a blog post.

I’ve done two part-time-to-full-time startups (one resulted in a startup the sold, the second is RescueTime– currently a YC-funded company– cross your fingers).

At the end of the day, I think Paul Graham is right when he says:

“The number one thing not to do is other things. If you find yourself saying a sentence that ends with “but we’re going to keep working on the startup,” you are in big trouble. Bob’s going to grad school, but we’re going to keep working on the startup. We’re moving back to Minnesota, but we’re going to keep working on the startup. We’re taking on some consulting projects, but we’re going to keep working on the startup. You may as well just translate these to “we’re giving up on the startup, but we’re not willing to admit that to ourselves,” because that’s what it means most of the time. A startup is so hard that working on it can’t be preceded by “but.””

In the beginning, however, it’s not always practical to dive in full-time. And sometimes when your idea is off-the-wall and also easy to build a prototype for, it’s smart to whip something out just to see if what you’re building is as cool as you think it might be before you take the plunge.

So 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 us when we did it part-time:

1. You need a co-founder and some cheerleaders… If you can’t find 2-3 friends who are really excited to be beta testers for what you’re building, ponder changing your 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 find a way past that. If you don’t, you’ll often lose interest and find something else to entertain you.
2. Pick a day or two per week where you ALWAYS work, ideally in the same room as your co-founder(s). ALWAYS, no exceptions. We did 1 weekday evening and 1 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? 5,000 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 2 co-founders to this issue (they weren’t ready to dive in full time and 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 v1 ia probably going to suck. Read David of Weebly’s post on persistence. It’s a long road. My first startup was a ridiculous fluke (2 months and then sold). 99% of the overnight successes you read about were slogging in the muck for 5 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 v1, 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 (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. All that being said, be aware of the fuzzy line between using your cool-down 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. [edit: Thanks to Ivan in the comments] Be sure you own your startup. 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 IP is not clear, do NOT rely on the good will 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 take it out of 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 with what you can pull off.