One topic that always seems to crop up at different startup related meetups and events is ”When do you know when the right time to get your startup going?” I hate that question. Usually it’s asked by someone looking for validation that they aren’t about to make the biggest mistake of their life by leaving their old life behind and creating a brand new one — Their Startup.

Indiana Jones and the Leap of Faith
It is a scary time — wondering how you’ll pay your bills, how you’re going to accomplish all the tasks on your insane ToDo list, how to explain it to your significant other… The problem is that there’s no way to know what’s going to happen. We can plan, but things change. So the truth is that there is no Magic 8-Ball in business, and we can fail at any time. But when to make that leap? That’s actually easy to answer:
When you have to.
When all you can think about is your business. When you don’t care if you are going to fail or succeed and just have to do it because it’s all you want to do. That’s when.
I was working at Dyn Inc. for 9 years, at a great job, when I left to start my company. I had 6 months savings (ended up being 3, thanks to storm damage) put away to help me get by until my company could take off (with some luck) but that was it. No more health insurance, no more quarterly bonuses, no more actual paycheck. I was terrified but excited; I was the founder of my own company! Hear me roar!
The very next day a bug appeared that affected all 65,000 of my users, not caused by me but a bug in Adobe AIR that invalidated stored settings, including if they were using a non-default location for their database. So if someone had changed the file location, the program wouldn’t see it as it’d use the default location instead and therefore it appeared they lost all their data.
Yes, the day after leaving my job to run my business full-time, I had the second worst possibility happen where users thought they lost all data in their database.
I was able to get a fix out that weekend, but if I hadn’t, or if users actually did lose their data, that would have been the end of my company over night. Kaput.
Two days after that, I proposed to my girlfriend (she said yes
). Two days after being hit by a problem that could have left me jobless. And then two days after that, I had to explain to her family how I thought leaving my job before proposing was a good idea. Talk about a difficult conversation . And she has a big, big, big family.
So was it the right time to make the leap? Yes. Why? Because I had no choice. I was working a full-time job during the day, going home and working until 2-3am, then getting up 4 hours later to do it all again. I was sitting on the couch with a laptop instead of spending time with my fiance and dogs. It couldn’t continue, so I had to pick between my ‘regular’ job, or take a 2/3 pay cut and do what I was passionate about. I don’t even recall thinking about it; I just knew I had to run with my company.
My own father still shakes his head in disbelief, muttering “I still can’t believe you left your job like that” every time it comes up. And I always tell him I can’t believe I waited as long as I did to do it.
So when is it the right time? When it is.
A bit of advice: don’t do it alone. There’s great resources out there to help startups of all kinds. If you’re in the Manchester, NH answer, check out the abi Innovation Hub, which I’m a member of. Otherwise, search around online for business incubators in your area. And hell, if you’re a Startup and I can help with anything, let me know! It takes a village to raise a kid or a startup.
