Category Archives: Psychology

How would you survive on a deserted island?

This is a question every entrepreneur should ask him or her self.


Well, simply stated in the words of the co-founder of Twitter Ev Williams, Starting a company is like landing on the shore of a deserted island.

That answer is actually the title of a blog post Ev posted way back in October 2008.  I read it this morning and it instantly connected with how I’m feeling right now.

Please go read Ev’s thought process on this metaphor here and let me know if you agree.



You don’t ask, you don’t get

There is something to be said about the psychology around being afraid of getting an answer of NO.  As a bootstrapping entrepreneur you have to know that most doors won’t just open for you, you’ll have to kick them down.

However, kicking down doors doesn’t work if you are afraid to ask for uncommon things because you think the answer will be NO anyway.

This morning I came across an awesome blog post from Mark Suster titled The One Word That Shouldn’t Exist in an Entrepreneur’s Vocabulary.  Suster states that his mom taught him at an early age that if “You don’t ask, you don’t get.

Suster also says about his mom:

She was a hustler. And a ball buster. And a natural sales person. She was never afraid of the word “no” even to the point of embarrassing me.

The key takeaway here is that closed mouths don’t get fed.  You should definitely go read Suster’s full post over on his blog.

Fear must be your motivator

One of the things I was told by my father years ago was that if you are not afraid of success, then your goals aren’t big enough (click to tweet this).  I came across a blog post this morning from the wildly outspoken, bad-mouthed super angel investor Dave McClure that articulated perfectly what my dad was telling me .

McClure’s post is titled Fear of Flying, and the one thing he makes clear is that the fear of failure is not what scares most great entrepreneurs, but instead it’s the fear of flying and maintaining the altitude.  He writes:

Of course it’s easy to fly high for a few days or weeks. Everyone gets lucky, hits their stride with gusto now & then, sinks a sweet 3-pointer once every 20 shots, writes some challenging routine that compiles the 1st time and works flawlessly, or closes a big deal they didn’t think was gonna happen. Sure, you can do that every once in awhile – but can you do it for a month? for a quarter? every day for a year? can you beat last month’s number consistently, and can you say with a straight face you’ll be able to beat that high-water mark again next month too?

This is an awesome post by Dave and I suggest you go read it on his blog right now.

Happiness is relative, manage it or it will manage you

There are a lot of ups and downs when you’re an entrepreneur.  You can feel like you’re on the top of the world one day, then only a couple days later feel like the world is ending.  Over time as business improves, you experience bigger wins on the good days, and smaller losses on the bad days.  What’s interesting about this is that your happy and sad emotions will not get bigger and smaller, but will continue to oscillate as they did on day 1.

I’m no psychologist, but this assessment is based on anecdotal evidence that was put into words in a fantastic blog post written by Jess Lee.  Lee’s post is titled Why Startup Founders are Always Unhappy and she states:

Unfortunately, humans are terrible at understanding absolute values. We are best at understanding acceleration and deceleration, or rate of change. For example, when you are on a plane it is hard to tell if you are moving at 300 mph or 500 mph, but it’s easy to tell if you are accelerating from 300 mph to 500 mph.

My theory is that a founder’s happiness is tied to the rate of change of their startup’s success. In other words, your happiness graph is the first derivative of your success graph.

Lee uses some pretty cool graphs in her post to illustrate the point she is making.  She also provides some great ideas on how to manage the ebb and flow of happiness and sadness along your entrepreneurial journey.

I suggest you go read the full post here.