This is an actual conversation I had with an entrepreneur earlier this week:

Entrepreneur: "I think we are bit later stage than when you guys typically invest."

Me: "I'm not sure I would agree actually. You have an experienced team but you are a pre-revenue SaaS company."

Entrepreneur: "Well yeah but I'm really confident in our sales-pipeline."

Me:

Alright so I may be paraphrasing a little bit but that's basically how the relatively short conversation went. I went from being interested (despite the fact the company was pre-revenue) to completely uninterested no matter what their potential might be. Every entrepreneur needs to project confidence about their business. It really does take a little bit of crazy to see a company through to success. This entrepreneur however was not just confident but very much overestimating their ability to generate sales for a totally new product from a company that no one has ever heard of.

Let's contrast that to a different conversation I had with an even more experienced entrepreneur just a few weeks earlier.

Me: "Sounds like a very interesting concept. I suspect with your background you're starting to develop a good understanding of your growth path."

Entrepreneur: "Well actually I think we would be a good candidate for StartFast. Even us experienced guys need some additional guidance now and again."

I actually was not expecting this second entrepreneur to be interested in StartFast. Whether or not we ultimately decide that they're a good fit, what impressed me most was that he demonstrated a crucial skill every founder should possess: the ability to be humble when you should be and be confident when you need to be.

The ability to be humble when you should be (despite success and experience) is incredibly valuable. Being humble is about being objective about the present state of your business. It keeps you constantly on your toes to see how your instincts match-up against reality. It allows you to be open to new interpretations, new ideas, constructive feedback, and new opportunities for your business to take advantage of. Overconfidence about these aspects is treating your business like the bird box challenge. After all, why would you need to observe your surroundings if you know exactly where you're going?

At the same time however, it's also important to have confidence about your company's future. Confidence does not mean overestimating the likelihood for a positive outcome of certain events. Confidence means being resolute about your team's ability to make success inevitable regardless of how the things outside of your control turn out. In fact, one of the tips we use at StartFast to help founders create their pitch decks is to imagine the title of every slide starting with the phrase "Success is inevitable because ..."

There are so many misconceptions about what being an entrepreneur is really all about. At the end of the day it's mostly about how you work with other people. Projecting confidence in the right way will mean that other people will have confidence that your success is inevitable. Projecting confidence in the wrong way will mean that other people will have no interest in keeping up to date on your progress because they feel they already know how the story will end.

Striking this balance in leadership is important for entrepreneurs to learn and master. The ability to be humble when you should be and be confident when you need to be means you are objective enough about reality to make the right decision given the information at hand and yet persistent enough that no matter what's thrown at you, you will find a way to continue moving your team forward.