One of the things that has always annoyed me about most investors’ blogs is they seem to be completely void of what frankly can often be the most difficult part of launching a company: dealing with the emotional side of the equation. A prime example is when you reach an existential crisis with a co-founder or early employee. These people are like family. You’re joining a fraternity together trying to launch a company and the personal bond is typically much stronger than in larger organizations.

What makes these situations even more difficult to deal with is that as an entrepreneur you’re thrust into this strange emotional paradox. On the one hand you need to be highly skilled at establishing empathy with people, and on the other you need to be very level headed when making difficult high pressure decisions that effect someone else’s life. Essentially what that means is you need to be very good at feeling other people’s pain and yet when you’re in a position to let someone go you need to be able to absorb and push past that anxiety to make a rational decision. …

It’s never a good sign when after a call with an entrepreneur one investor says to the other “I promise you he wasn’t that crazy on my first call with him.” That’s actually a direct quote from me earlier this week. Now I don’t bring this story up just to poke fun at an entrepreneur, far be it from me to ever do that. There would be no StartFast without the incredibly talented, driven, and passionate founders we work with.

I wanted to highlight this story because it epitomizes a very common trap entrepreneurs fall into when pitching their business to the outside world (not just investors). Founders are always straddling this difficult line between being imbedded in the weeds of day to day operations while at the same time carrying with them a large and often abstract vision for the company. That means when they’re describing what they’re doing to people on the outside one of two things usually happens: 1) they dive too deep into the details in which case everyone gets lost without context, or 2) they jump to their higher level vision in which case no one can wrap their head around what your company looks like in the real world. …

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.”


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