Digital Design

First in, last out

Employee #1

Lessons learnt as Employee #1 at a failed startup

After two and half years, the software startup that I helped build since its inception went bust *. Like roughly 45% of businesses in the UK, we died within our first 3 years. This is the introduction to a series of posts unpacking some of the lessons I learnt in that time. Hardly a unique concept for a blog, but perhaps my particular perspective as the first employee in a tiny business will provide a small point of difference.

* We got an 11th hour acquisition! But this did not include taking the team and it was not for the sum of money that might have been hoped for. So I think my perspective on the experience remains the same.

My goals for this series

  • To learn from my mistakes. I want to take time to reflect upon a unique chapter of my career and find lessons for the future.
  • To write! I enjoy writing and would like to get better at it. Having a defined ‘project’ I hope will give me the motivation I need to put digits to keys.


I’m Rory, a sort-of-designer-ish from the UK. I started working on ‘digital’ design back in 2009. Things were very different back then. It was a time when digital designers had to understand a bit of everything — marketing, content, code — by necessity. There wasn’t demand for more specialised roles at that time. And I’ve sort of continued that approach throughout my career. 

I tend to be interested in the machine as a whole; how all the component parts come together to form a viable product and a business. I don’t really understand how to be a good ‘designer’ without having a broad understanding of the many variables that go into building something. With that mindset, I’ve emerged as somewhat of a ‘jack-of-all-trades’. I can do a bit of lots of things, which as it turns out is very useful for early-stage start-ups.

Employee #1

I joined Connect4, a tiny software start-up in the summer of 2020, first on a freelance basis and then later as an employee. My official title was Head of Design but I prefer the term ‘Employee #1’. I did plenty of design work; product design, branding, pitch decks and website design. But I did a whole lot of other stuff too, from sales calls and demos, to marketing and front-end coding.

I stole the title ‘Employee #1’ from Shoe Dog; Phil Knight’s book about founding Nike. I was drawn to the story of Jeff Johnson, who was the first employee at the sportswear giant. Knight casts Johnson as somewhat of a misfit who is unemployable beyond his ambiguous and multifarious role at Blue Ribbon Sports (later Nike). I don’t exactly relate to the ‘misfit’ or ‘unemployable’ bit (hopefully) but I rather admire the description of a hands-on problem-solver who’ll give anything a go. That’s the type of person start-ups need and I think is perhaps becoming rarer as tech roles become ever more specialist. Anyway, I digress. On with some content.