The 5 Curses for an Entrepreneur

Image by    Stephen VanHorn

Entrepreneurs often suffer sleepless nights. So, what leads them here?

In a report by Startup Genome, ‘Within 3 years, 92% of startups failed. Of those who failed 74%, failed due to premature scaling.’ It’s a little easier to understand those sleepless nights when you read stats like that.

I have observed five curses at work that when alone or combined, make life very difficult. The last is more specific to the software world but the rest are widely applicable.

1. Stress
2. Overconfidence
3. Poorly understood needs
4. Hidden assumptions
5. Failure to communicate


Being an entrepreneur means being in the business of searching for a viable business model, while your cash pile dwindles day-by-day. After death, and giving presentations, this is one of the most stressful things you attempt. And something we know about stressed people is that their judgement suffers. You may be too stressed and not even realise it.


If you are the kind of person who, when you share your great idea and get shot down think, “Oh, yeah, right - maybe this won’t work”, then you don’t get in the room. By definition, entrepreneurs are the people who don’t listen when other people tell them their idea is stupid. Confidence is built in to an entrepreneur but you have to be careful not to take it too far. The challenge is that, no matter how smart you are, at some point you actually ARE going to be wrong. Confidence - good, overconfidence - bad.

Poorly Understood Needs

You think you understand your customer very well. But what you may not realise is that people are good at lying. Spectacularly good, actually. You proceed on your understanding of your users needs, only to discover (and usually after spending a shit-ton of money building a product), how wide of the mark you are. The result? You are left in a muddle, scrambling to adapt, losing time you really cannot afford to lose. 

Hidden Assumptions

We all make assumptions, sure - and there’s nothing inherently bad about this. But in my experience, the danger is that assumptions can harden into ‘facts’ really quickly if you don’t manage them aggressively. We should always be asking, “What evidence do we have for this assumption?” And, “If we’re wrong about it, how screwed are we?” David Bland’s Assumption Mapping tool is excellent for handling this.

Failure To Communicate

This is a problem particularly when building software. Typically, it’s very hard for non-technical entrepreneurs to communicate with the people building their product. They get too involved in the, ‘How and what’, when they should be focused on the, ‘Why and when’. Conversely, developers have no idea ‘Why’, so they cannot help with better ways of doing things and the product then suffers.

It may be that one of these is curses is affecting you. It may be a combination of a few. Do you know? And more pressingly, do you know what are you doing about it? 

Tell me… 

Find me on LinkedIn Follow me on Twitter Join my mailing list

Matt MowerComment