Diary of a software start-up. Day 1.

A new beginning

Today was a big day. Exactly two years ago today the company I co-founded (Clicktools) was sold to to Callidus Inc (CALD). As part of the deal, the co-founders had a minimum contracted 12 months tie-in. The opportunity of working in a larger, successful software company was pretty exciting. to see what, if any, difference I could make and the opportunities looked positive. However, after 6 months, it just wasn’t for me. Leaving meant losing a fair amount of stock options and also meant I couldn’t do much because of a 12 month non-compete clause that covered a LOT of what I would probably do if I did leave.

But, in July 2015, I left. I looked after the renovation of the house we had moved into and this summer, I spent more time with my children and I thought, woohoo… golf, tennis, coffee, box sets here I come! And it was, until my brain started to turn to mush and the guilt increased as my wife was out working all day. I spent way too much time thinking about whether Britain should leave/remain in the EU and reading Twitter and Medium. The Daily Politics show became a ‘must watch’. I could not - no, I would not do this for the next n years. The question was, what should I do?

I’d had some outline ideas about new products for a while but, initially, the thought of starting something from scratch again didn’t appeal too much. I liked the ‘idea’ of a 9–5 job and started to look around. Boy; the recruitment process had changed A LOT since I last had a job interview (~20 years ago). I looked at jobs I thought I could do (and wanted to do) and heard: Too old (I am 49). Too experienced. Not enough experience. Too entrepreneurial. Not entrepreneurial enough. Would you consider a sales job to earn your stripes? etc. ad nauseum. I eventually had a few interviews; couple of offers which were local, good money and were ok…

But that’s the thing isn’t it? The jobs were just ‘OK’ and ‘OK’ is just not enough. I decided that, if I was going to work again, I wanted to enjoy it, love it, live it. There was no way I could be as committed as much as I wanted to be or they deserved. I pulled out of a couple of other interviews for the same reason.

At the same time, I had a conversation with someone who was a little further down the road in their start-up journey. I hope I gave him at least one piece of worthwhile advice but something in the conversation lit a fire in me. Memories of experiences, good and bad came flooding back and I was talking passionately about a subject I actually knew something about. I thought this is what I should do. This is what I wanted to do. This is what I could do.

So, this morning, two years to the day we sold Clicktools, I dusted off the incomplete business plan, re-read it and thought yes; this is it.

I decided I would document the journey so whether it’s good or bad, happy or sad, my thoughts and feelings would be captured. And, who knows, 1 or 2 people may find it useful.

Day 1. A new dawn, a new day, a new life; and I’m feeling good…