My best decision...
Some of the best decisions I have made have concerned relinquishing equity. For example, when I was running my first company, an internet design firm, I recognised there were certain skills I didn't have and in order to get the right person I had to give up 30%. It sounds a lot, but without that person the business would never have achieved the success it did.
It was also a good decision to base my second business, feelunique, in Jersey. At the time, there were tax advantages. That said, the warehousing and postal costs are higher, so any tax benefit we did once see is balanced by the additional costs. Living in Jersey does give me a great work/life balance. I live 30 feet from the beach.
It was a big decision to have children - but a good one. The business was three years in and my wife and I were both pushing 40. Our twin girls are now two. Having children really keeps you grounded. When you realise that their whole world is about you as parents, it makes everything you do during the day seem insignificant.
My worst decision...
It was a mistake not to go to college, though it has all worked out in the end. The path I followed and the choices I made got me to where I am now and I'm very happy. At the time, I couldn't see myself in education for another two or three years. I missed out through laziness.
When I got divorced from my first wife in 2004, it wasn't an acrimonious split and so in the interests of making life easy I let her have the lion's share of our assets. I don't regret it because it felt like the right thing to do. But my lawyer said it was a bad decision and, in hindsight, it probably was.
I also have a string of bad hires behind me. Most recently, we recruited a senior person in our financial team. We were really impressed by the CV and by the individual, but had to let the person go after we found out they were moonlighting, among other things. Sacking someone is a very painful process and it could have been avoided if we had done more background checks. No matter how impressed you are with someone, it is really worth doing your homework.