Discipline & Format

I love/hate writing. I know that writing is one of the best ways to clarify my thinking (another is going for a long run), although there is always *something more important* to be done. But I also know that if I write more I’ll be better at getting those important things done (and say ‘no’ to anything else). Writing well takes practice — I know I won’t suddenly wake up one day and be a great writer — and to get practice (especially on those ‘I hate writing’ days) takes a great deal of discipline.

Whilst on a run on Friday, however, I came up with the following format for my writing.

Here’s the format:

• Summary

  • Three bullet points about the company.

  • Only ever three.

  • No more, no less.

• What is [CompanyName]?

  • A brief description of what the company does and, most importantly, what it sells. Entrepreneurs can get caught out explaining a lot about what they’re doing without actually telling an investor what they sell that gets other people to give the company money.

• What is good about [CompanyName] right now?

  • Why do I like this company? There is no shortage of investment opportunities so why is this company more interesting than many of the others that I see?

  • In startup companies it’s all about the founding team, their character, discipline, insight and courage — what is this team doing that’s better than others? What do they think they know that others haven’t seen?

  • I like to meet founders doing something surprising — the most insightful thing to figure out is, “Why is this person doing this thing right now?”. If I can figure that out I’ll have an insight into if they’ll keep going when the going gets tough.

• What are the challenges [CompanyName] faces?

  • What is the main challenges that I see for the company?

  • Entrepreneurs are, of course, doing something new — new for them, new for their customers — and the guaranteed result of doing something new is that it will get difficult (it’s inevitable that, at some point, they’ll want to give up and will be under pressure to give up).

  • So what difficulties do I think are emerging in the near, mid or long term that they’ll have to face and overcome?

• What must [CompanyName] never stop doing?

  • What do I think is a core driver of the company?

  • The thing that the company mustn’t lost sight of or compromise on. This is often non-obvious and, if stopped, may not have an immediate impact.

  • Linked to the “why is this person doing this thing right now?” question. In the best companies there is a core, baked-in-DNA reason they are doing what they’re doing — over time it can be easy to lose sight of this. Nothing may change in the short-term but months or even years later the company will fail because they lost sight of their ‘why’.

Will this format help me get the discipline to become a better writer? I hope so. Over the last few years I’ve been inspired by Seth Godin, who writes every day, and Paul Graham, who writes once in a blue moon. There’s no one way to do this.

Beginning with my own companies, 9others and DMG, going on to describe my own portfolio and then writing a summary for some of the best companies I meet I hope to communicate the thinking behind my decision-making as an angel investor.