Half-Assed Startup: How do I start my company and keep my day job?

[Ed: I enjoyed Tony Wright’s contrarian article, Half-Assed Startup, when I first read it on his excellent blog. Tony, a founder of RescueTime (Y Combinator), argues that you can start a company while you’re otherwise employed. And he explains how to do it. Tony kindly agreed to re-publish his article on Venture Hacks. Take it away Tony.]

I’ve done two part-time-to-full-time startups. One was acquired by Jobster. The second startup is RescueTime—currently a Y Combinator funded company—cross your fingers.

At the end of the day, I think Paul Graham has it right in How Not to Die:

“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 when your idea is off-the-wall and easy to prototype, it’s smart to whip something out just to see if it’s as cool as you think it might be—before you take the full-time 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 two or three friends who are really excited to be beta testers for your product, ponder changing your direction. In a part-time effort, a co-founder is essential to keeping you on-track and working. At some point, you’ll hit a motivation wall… but if you have a partner who is depending on you, you will find a way past that. If you don’t have a partner, 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-founders. Always, no exceptions. We worked one weekday evening and one weekend day. That doesn’t mean we weren’t working other days, but keeping 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? The target should be a shared understanding. You don’t want one founder who is ready to go full-time while the other 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 startup is a hypothesis. If your hypothesis is, “we can build a better web-based chat client”, that’s something you could test quickly. If your hypothesis 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 minimum that is necessary to test the hypothesis. No extraneous features!


5. Understand that your first version is probably going to suck. Read David Rusenko’s article, The importance of launching early and staying alive. David is a founder of Weebly (Y Combinator). It’s a long road. My second startup was a ridiculous fluke—it was acquired after 2 months. 99% of overnight successes 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 first version, look for the tiny little flicker than you might be onto something. And use it 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 or 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. That said, be aware of the fuzzy line between using your cool-down time at work for your startup and stealing time or 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’ve had the fortune of working in 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 good will of your employer. Greed can do funny things to people, even if they were initially big supporters of your startup. (Thanks to Ivan from TipJoy for this final suggestion.)
   
   

In short, 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—you might be surprised with what you can pull off.