My best advice is not to drop your work for as long as you can
until you see traction. In our case, Joel only stopped working after
we hit ~$1k in monthly revenues.
(read: http://joel.is/post/6687368692/startup-bootstrapping) and I
only dropped out of College a lot later after Buffer actually had
already received funding and was supporting a team of 5.
I think the key might be to only drop your work once your
revenues are enough to support you. So I would try and make that
window almost 0, in our case working nights and weekends is a
great way to get there.
Thanks, that's very helpful! Much of my problem is that I'm coming into this as a full-fledged grownup - twenty years in the industry, two college-aged kids, mortgage, car payments, etc. What cushion I have is my retirement money, and my spouse will only let me burn just so much of that before she loses patience. I could maybe get a few months of pure bootstrapping in, but the drop from a six figure income to less than minimum wage is very steep indeed.
Right now, it's 20+ hours a week on the startup in my "copious spare time". What worries me is the pain waiting for me when the rubber meets the road... the support time and emergency fixes needed when I have real, paying customers. That's when the conflict between dayjob and startup will truly loom large.
But what the hell, I WILL make it work. I'm done with working for other people. I've already signed my Declaration of Independence, but if I want my freedom, I'm going to need to survive my Valley Forge as well.
I too was doing my startup part time for about 6 months before we were admitted into an accelerator. I am currently working FT on my startup. But my personal situation is completely different than yours (no kids, no debt, no house, low cost of living state, cars all paid, spouse working ..) . Take baby steps every day and you will be surprized how much you can accomplish in few months. Be consistent about it and you should be good.
On the plus side, my wife has a high-paying IT job as well, so we won't starve immediately. And I'm kind of boggled at how much I've managed to build, effectively solo (legal help only), in the past six months. But I have another six before it's really money-ready, I think.
