I have often wondered what defines me as an entrepreneur: Is it the fact that I've managed to co-found a genuinely successful and profitable company (WooThemes)? Or the fact that I've tried my hand at quite a few other projects and ideas along the way?

Can I be considered successful if my failures outrank my successes? At least in terms of the amount of failures I've had, versus my own - albeit very significant - success?

I've always been very critical of myself and in that vein I'm constantly tempted (yes, in that very emo way) to feel like I'm more of a one hit wonder, than a serial entrepreneur (something which I aspire to be... I think...). See, I'd love to believe that WooThemes was no fluke and that I could use the skills, knowledge, experience I've acquired via WooThemes and apply this to a new business venture in future.**

Until now that hasn't really been the case, with most of the side projects I've been involved with either stagnating or not really growing in the desired direction.

I've been toying with the idea of becoming an angel investor and at least repurposing parts of the wealth (experience, knowledge, connections, as well as financial capital) I've accumulated to diversify my business interests. I'm keen on this only partly for financial returns, with the determining consideration being that I love being involved with awesome projects. This however doesn't solve my feeling that I might be a one hit wonder... But then again, how many entrepreneurs have really gone on to found multiple companies? (I'm not talking about those that have simply become financial backers of a great idea; I'm talking about getting involved in the trenches of a startup all over again.)

Heck, shouldn't I even be concerning myself with these questions and self-doubt?

** I don't intend on leaving WooThemes for the foreseeable future.