The Angel Investor: Inflexibility is a Sure Way to Fail

My team of angel investors just made our latest series of investments. We read over 200 submitted applications, witnessed over 20 pitches in person, and made three investments in web and mobile startups which we announced this week.

Every investor will tell you ‘the entrepreneur’ is a key component of any investment decision they make. That they invest in the individual as much as in the idea. Our board thinks similarly, and I am often asked ‘what do you look for in an entrepreneur?’.

Along with the regular responses – passion, skill, experience, leadership qualities, etc – I always include ‘flexibility’. We will never invest in an inflexible entrepreneur, as that is a sure quality which will lead them, and us, to failure.

Startup journeys should always be planned. But they never go according to plan. Many factors will lead to pivoting. The more flexible a founder is, the more skillful they will be in the art of the pivot.

The first three investments made by our team, the KAYWEB Angels –, and – are all very different products now than what was pitched to us many months ago:

  • has changed its entire product after closer analysis of their marketplace;
  • has changed its monetization strategy and added a new service stream to their business after market consultations and advice; and
  • has added a monstrous amount to their scope due to realization of new opportunities not yet explored by competitors.

The founders of these startups are flexible. They dream. They listen. They speak. They learn. They teach. They pivot!

The qualities that classified them as ‘investable’ by the KAYWEB Angels board are now shining through as their products move closer towards launch.

Our most recent series of investments – Cafrino, Minute Lister and You Need My Guy – all had their flexibility tested during their pitches in person. Whether we suggested a change in name for their startup, a change in their monetization strategies or their planned efforts in marketing, they showed an openness that not all others showed.

We are very excited to welcome them as the latest additions to our portfolio companies.

Inflexibility is an ‘uninvestable’ quality, while the opposite is one of the main things I, and many others, look for in an entrepreneur.