I've been running side businesses while having dayjobs most of my working life. One of those side projects, my xen vps hosting company, is now my dayjob. Of

I've been running side businesses while having dayjobs most of my working life. One of those side projects, my xen vps hosting company, is now my dayjob. Of course, you might not call it a startup; I'm not really looking to sell (I mean, I would if someone wanted to give me a 10x revenue valuation or something silly like that, but I doubt that will happen.) and it's north of six years old, but revenue is doubling every year or so, and it pays my rent and covers another full-time employee (plus contractors) Having a well-paying dayjob changes things. You will want to hire your first employee long before you would if you were working full-time at the startup. You will want to spend money rather than do work more often than you would otherwise. Assuming you have a high paying dayjob and you are willing to live cheap, your runway is now measured only in terms of your motivation. Note, you will not be performing 100% at the dayjob. I got asked to choose between the dayjob and my business only once, though, and that was near the beginning, before I really learned to compartmentalize, and when I was most focused on my business. My style of work is and always has been very burst-y, which works out well. When I wasn't that focused on the business, I'd get a regular dayjob and top off my COBRA and rent money. When I was focused on the business, I'd either focus on the business completely or work contract gigs for extra money. It's interesting; if you contract through a body shop for non-expert work? (e.g. if they rent you out as a normal programmer/sysadmin?) it pays only slightly better than doing the same job as a direct employee (sometimes a little worse if the benefits for the direct employee are good) but the expectations for your work are much lower. I mean, think about it; if they are paying about the same for a contract as for a full-time with benefits job, do you think they are going to get good people? The lowered expectations along with the ability to spend pre-tax dollars on company equipment made that a pretty good deal for me. Especially during the money-losing phase (and this /will/ be longer than it would have been if you were full time.) the taxes are complex and can make a huge difference. get a good accountant, and listen to him or her. Small bullshit changes can make the difference between spending pre tax money buying servers and spending post-tax money on those servers.