I had a commitment of 3 years after the initial exit (in 2015); since last year (2018), I no longer have any operational function at the company (I still have some shares).
I often hear the claim that “you aren’t committed enough” if you don’t quit your job to work fulltime on your own business. In my opinion, that’s not a general truth.
Sometimes I agree with the claim. You need a sense of urgency to succeed. On a psychological level, the safety net of a certain job might prevail over the uncertainty of your own startup business, resulting in you making the wrong decisions.
However, keeping your day job isn’t always bad. When you quit your job to build a new product, you might end up “working in a void” (especially if you don’t have any customers yet). You might be building something that looks like a good idea in theory, but that you won’t be able to sell to anyone in practice.
Thanks to your real job working with real colleagues on real projects, you will gain real experience you would otherwise never acquire working with your friends on an experimental project. That experience might be exactly what you need to make a great product instead of merely a good product. (Also don’t underestimate the social skills you might lack if you’ve never had to work with people you didn’t choose as co-workers.)
So how do you balance between “you should quit your day job” and “you need a day job”?
Combining a day job with your own business requires that you have a clear understanding of what it is you want on the long term, and the discipline to stick to your long-term plans.
That’s easier said than done, but I solved this by putting deadlines/milestones in my agenda three months ahead, half a year ahead, one year ahead, even as far as three years ahead. When such a deadline is reached, Google Calendar sends me an email, and at first it’s confronting when you get a mail showing you a milestone you imposed on yourself and didn’t meet, but once you get the hang of it, you learn how to meet your own deadlines.
At some point, you’ll start learning more from your customers than at your day job; that’s when it’s time to quit that job. In hindsight, I might have waited too long: my milestone was $500K revenue. That number triggered my decision to quit my “certain job”, but knowing what I know today, I could have quit that job at least a year earlier.
But the bottom line is that I defined a strategy with targets and deadlines at every stage in the life cycle of my company. This was a repetitive process because every stage in that life cycle requires a different strategy.
I made a fun slidedeck about those strategies: https://www.slideshare.net/secret/jidUnZJ1jBaaLr
I presented this deck as a keynote at the film festival in Ghent last year. It’s also important to note that four of my projects failed before I had any success.