You are a start-up founder and you're wearing a bunch of hats. But are they a good fit? Are you wearing them well?

Our previous start-up, BookIt, was a pretty typical boot-strap tech startup. Andrew and I learnt to wear a lot of different hats. We worked out (sometimes the hard way) which ones fitted us well and when it was time to hang a hat up.

We are both tech founders, more specifically we are devs. But we make a point to learn the other parts of the business intimately. There are practical limits to the number of hats you can wear and over time we built up a great network of experts in the various fields. But before we got there, we made a point to wear their hats and hold onto wearing them for as long as practical.


It’s your business and your dreams. It is your future on the line. Having any part of your business that is a “black box” is not cool. Sure, you will be out of your comfort zone at times, but it is worth it.

So wear other people’s hats and wear them well. Know your legal agreements and your financial statements. Understand your marketing plan, product road-map and system architecture. Read & understand all of it. If anything doesn’t make sense, question it, shape it, make it fit you and your business. Stay open to being convinced of things, but don’t shy away from demanding that you should be convinced.

In the longer term, when you hand the “other hats” back to their rightful owners – you do so with an understanding of what wearing that hat involves for you and for your business. That is invaluable.