“I saw the angel in the marble and carved until I set him free” – Michelangelo

Last month I made my first angel investment. I know many of my blog readers are entrepreneurs and startups and some of you are or will be seeking angel investment, so I thought it might be useful/interesting for me to jot down (from a poacher turned gamekeeper type of perspective) for you a few of the choices I’ve made along my own personal investment journey and why – in case it helps you.

To set the scene I’ll start with why I’m doing a small number of early stage angel investments in the first place and what my criteria have been. My main objective was to eventually select a handful (my final number is three) of early stage startups where I liked the idea but more importantly liked the founder or startup team. My motivation is to use some of what I’ve learned starting and scaling my own businesses in the past to help a small number of other people get through their early growth stages less painfully than it was for me. If I make any money along the way, I’ll celebrate that as a bonus. Making money is not my primary objective – which is lucky because many of the wise heads I know have gleefully warned me (a few of them several times over) that it’s impossible to make money by investing in early stage startups.

A couple of other bits of info make up the full picture. Although I’m a member of a couple of formal angel networks, I haven’t invested through them or as a part of any of their syndicates. So far anyway.

Finally, the startups had to be somewhere on the spectrum of my own areas of interest so that I can add value. This inevitably means software, X as a service or platform, community, scaleable, public sector, always something to do with people and how they can save time or money by collaborating, learning from each other or working together.

I’ve been talking to startups for years. It’s a natural part of what all entrepreneurs do. For me the night out that will always trump all others is one where I can watch other startup entrepreneurs pitching. I just love that initial rush of thoughts about another person’s ideas – working out the angles on the business models and the commercials…seeing if I can spot some opportunities that they’ve overlooked. As an aside, I love it even more if it’s something I’ve considered doing myself in the past but haven’t been able to work out the commercials or the logistics and then someone else manages to do that (for example, Northern Irish startup Send My Bag).

As a seasoned and successfully exited entrepreneur, people seek me out anyway for all sorts of reasons. Because of this it was fairly easy for me to start about a year or so ago to assemble a long list of 20 or so potential investee companies and kick off an initial conversation with the founders as a way to start my selection process.

This is what I was considering:

• Do I like the product or product idea and am I convinced it can scale?
• Would I buy it myself for my own (theoretical) organisation to use?
• Is the founder credible, articulate, stable and sensible but with a dollop of sparkle?
• Do I like them enough?
• Can I see myself working with them over the next 3-5 years?
• Are they resilient enough to keep things moving forward when times get tough and do they have the grit to sack bad hires quickly and stand up and fight for themselves and their company when they need to?
• Are they well-informed about their competitors and the way the market is moving?
• Can the founder front the business; are they likeable and convincing without being arrogant and smartass?
• Is their company valuation reasonable and realistic?
• Do they have a good overall grasp of what their next 2 years looks like in terms of back of the envelope targets, resource requirements, funding, effort needed, team, etc?
• Is the founder generally on top of their workload and easily able to articulate key messages and information?
• Are their targets and forecasts reasonable or complete pie in the sky?
• Can I clearly see how I can add value to both the founder and the company?

It took me a while to put the above list together as I’ve never written it down before. In case you’re wondering – yes – it is more or less in order of importance to me. I did say this blog was going to be about my own personal investment journey…

Only companies that passed the first 2 questions made it onto my long list of 20 companies in the first place and then between June and December last year I whittled those original 20 down to 3. I guess where it gets interesting is how I did that. I’m afraid it isn’t scientific for anyone who’s expecting a checklist and a spreadsheet.

A few fell at the valuation hurdle. If all you have is an idea and you don’t have any product built or any customers, your company in my eyes is not worth £1m. Simple as.

A few others fell by the wayside because of the founder. The trick here is to keep meeting with them until you’re either convinced that they’re the real deal or until they let their guard down and expose themselves to be anxious, needy, deluded, arrogant, ego-driven, greedy, selfish, brattish, indecisive or any of the many qualities you as an investor don’t want to see in a startup CEO or leader.

Some over time I just had a bad feeling about, or something told me that the founder wasn’t 100% honest – I could just feel it wasn’t good when I scratched the surface.

Others I lost because a few months in the product was no longer holding up or it became apparent that the founder wasn’t able to move at the pace required to get to market within their window of opportunity.

A couple went because the founder had more than one focus and it became apparent that they were spread too thin and weren’t giving any of their projects the attention they deserved.  A couple more because the founder knew it all and wouldn’t listen to any advice from me or from anyone else.

And so I was left with three – which was the number I was hoping for in the first place. Two of “my” founders are female and one is male. They all share a number of important qualities and despite their differences they’re remarkably similar.

This blog is part of a short series and I’ll write about the companies themselves next time around.

If you have any questions please ask them in the comments section below and I’ll do my best to answer.