This is a story of imitation...

I pitched the Cambridge Angels in flip flops. They didn't like this very much. It was a hot day in June though, so I thought it was appropriate. Perhaps I was a little over-inspired by The Social Network, but at least I wasn't wearing my dressing gown.

I also structured my company, so that my shares would be less diluted when the company received investment.

I was even so paranoid about anybody wrestling control of my company away from me, that when I wrote and signed a vesting agreement for my co-founder in a pub, on a napkin, during the first weeks of the Springboard Accelerator Program, in Cambridge, I deliberately held the pen upside down for the photo. Plausible deniability.

Anyway, so Hubflow is winding down operations, and that means I failed as CEO, despite the fact I stepped down a few years ago. Of course I wanted to give all my investors a big payday, so put a black mark against my name.

People should remember that I always had one eye on the sales pipeline and another eye on the bills, taxes, and wages. I would never bankrupt a company. However, it's all credit to my co-founder for getting things in order when I became unwell.

It's tough at the top, and I have nothing but respect for anybody who is in a CxO position. I'm not after anybody's job... I know how much of a kicking the executives get from investors, customers, and the sleepless nights thinking about everybody who is depending on them.

I'm also not so naïve as to believe that I should be telling anybody how to build a successful startup yet. I learned loads on the Springboard program, but those lessons have yet to express themselves in a useful and productive way for everybody who invested time & energy in me.

I'm wrestling with an unquenchable desire to research and develop stuff, to innovate, to explore ideas. I know that I can deliver a project as a solo founder, or build something from day one with the right co-founder(s). Bringing people in later in the life of a startup, is very difficult.

I also know that I can be a developer, or I can be a startup founder...  not both. Sure, I can write code, I can fix bugs, but the demands on a founder are so great that it's impossible to do the development as well. I was writing and maintaining code for the iPhone, iPad, Android, BlackBerry, Windows Phone, web application, maintaining the database, doing sysadmin, operational support... it was too much, on top of raising money, meeting customers, pitching and meeting mentors.

On the Springboard Program, Jon and Jess did a great job of supporting the founders. I know that Jon also went by far the extra mile for the teams that were dealing with issues, and the safety net that was there for me could not be faulted. I had bitten off more than I could chew.

I was always torn between raising any kind of investment round (friends & family, seed) or bootstrapping. I also was conflicted about bringing anybody into my startup, except hired help. I didn't trust anybody. I also couldn't let go of control and empower anybody to help me.

When you are bootstrapping, you don't have any money. For anything. Making rent payments, wages, expenses... everything comes down to one thing and one thing only: how much runway have you got left for your burn rate? You run lean, but you also run stressed. That's not an excuse for me not being a team player though. Hubflow probably could have been a bigger success if I had learned the importance of Team, as well as Traction and Technology.

You live, you learn.

Photographic evidence that I did make people laugh as well as cry. I think we had great times in Cambridge. I know I did (May 2011)

Tags: #startup #entrepreneur #university #career #leadership #computing #apple