Every passion project comes to a point. A point of no return. The point when it becomes not just a side project, but your main source of income.
You leave the nest of your 401k from your employer and fly toward the sun of stock options growing in value. Its a beautiful idea, but if you’re not careful, while you’re out there flying, you may get hit by a drone and fall down to the earth.
Another analogy I like to think of are boats. Companies are different ships out in the sea of business fighting and jostling with each other in the vast expanse. Big companies, like Apple and Google, are giant, sleek, new aircraft carriers. They are huge self-sustaining floating cities. While others, like Ford or Macy’s are venerable cruisers, also large, carrying the weight of the past with them. And then there are the startups. Row boats, jet skis, private yachts, little cruisers, kayaks and everything else of varying sizes all getting tossed about by the bigger ships around them.
I was on a boat. A big boat. A cruise ship if you will. And it was great. But after being on there for a while I realized it was not taking me the direction I wanted to go. I wasn’t growing in my career exactly how I planned. So I wanted to get off. I asked some of the other large passing boats who seemed to be going my way, but they said no. So what was I to do? I took an escape vessel, a row boat, grabbed two buddies and we jumped!
It was exhilarating at first, the 3 of us rowing away from the big bloated company before and heading where we truly wanted to go: toward our passions. Except, out in the middle of the sea, a row boat isn’t the best. You usually need help. But still we continued to row, until we realized we were rowing in circles a bit. We didn’t even know where we were going, our compass wasn’t working. And so we sank, the other 2 jumped off and joined other passing boats, and I was left with a sinking row boat. There’s not much value in a sinking row boat. Not much you can do with it. So I let it sink, and just floated on with its remnants, but I was sunk. I was no closer to getting to where I wanted to go than if I had stayed on the big cruise ship.
So what should I have done? Well its simple, I should have stayed on the big ship a bit longer. Wait for it to get to port, see where its next destinations were, and from there I could talk with other captains to find a more desirable ship to join or a master ship builder to build a bigger boat than just a row boat. Then I could get to where I wanted, with other experienced navigators on fast ships, not just myself, or even a few partners, in a slow row boat.
What am I trying to say here? I guess, in simple terms, don’t leave a well paying job for a boot-strapped startup. It’s just not worth it, no matter how much it seems like it is. It’s probably best to get VC funding; if you secure the seed round, you can quit, but not before the check is in the bank.
If you are determined to bootstrap your company, you will need to find time to do it in your nights and weekends in addition to your day job. If that’s too hard, you aren’t ready to start a company anyway. In hindsight, I certainly wasn’t. As it grows, only when its annual revenue, divided by owners, is at least similar to your current annual salary should you leave. Just because you’re making similar money in the startup today doesn’t mean that will sustain itself throughout the year.