As An Entrepreneur You Can Expect a Lot of Things



As an entrepreneur you can expect a lot of things that come with the journey – it is more than anything else a proverbial rollercoaster.

Excitement, uncertainty, a sense of accomplishment and the pure adrenaline of chasing your dream. In the beginning, most of your focus is on what can go right. In fact, it is a requirement to get started! The motivation to start comes from that big vision – building a company, disrupting an industry or solving a huge problem.

You dream of building a culture, creating jobs, doing the impossible and perhaps getting wealthy along the way.

As I type this I get goosebumps.

Every day at Next Coast Ventures I get the pleasure of meeting amazing entrepreneurs filled with energy and enthusiasm as they pursue their entrepreneurial dreams. I get to briefly and vicariously put on my past entrepreneur “hat” and dream big with them.

It is so inspirational.

But as an entrepreneur, unfortunately, something will happen along the way that can shake you to your core. You lose a key customer. A critical team member quits. You cannot raise the capital you need to run your business. Consumers don’t think your product is really as cool as your mom thought it was when you showed it to her just a few months ago. Or the real lottery winner – a global pandemic happens and your travel startup is hit with a huge punch in the face that no one could have ever predicted…

I call these “oh $hit” moments and every entrepreneur knows this experience. In fact, if you are going to be an entrepreneur you can expect so many of them you will lose count (and that is what wine and therapy are for as it turns out…)

These “oh $hit” moments are predictably followed by a mental avalanche of destructive thoughts and demeaning questions, the worst of which is:..

Why the hell am I doing this?

Why? Why? Why?

This one question has destroyed more entrepreneurial dreams than just about all other events combined.

It is the question that makes you question everything you are doing and changes your perspective from the positive dream to the consequences of failure. This alter-ego of negativity, despondency and weakness is what I refer to as your “Mr. Monkey.” voice. If you listen to this voice espousing fear, uncertainty, and doubt, your temptation to throw in the towel will be high. The key is to not let the voice win.

But how can you do this? How can you stay connected to your entrepreneurial vision when everything seems to be telling you to give up?

Here is a simple formula that I have found the most helpful when I struggle with this very issue. It is an exercise that helps me keep my focus and resist the rabbit hole of negativity that Mr. Monkey wants to take me down. And it is a pretty simple way to use the “why” question in your head and take your thoughts in a different direction. And it’s an effective and simple way to take Mr. Monkey’s “why” and turn it on its head.

In short, it is an exercise in mental judo.

Think back to the start of your entrepreneurial journey and ask not just one but three “whys” – but focus on your original vision. Think about the very reason you started on your journey in the first place.

Ask yourself “why did I start this in the first place?”

Whatever your response is – ask the same question again. Then do it one more time.

For me, it would go something like this as it relates to my decision to do a 180-degree professional pivot from an entrepreneur to a venture capitalist co-founding Next Coat Ventures a few years ago:

Me #1: Why at this point in my career did I want to change to being a venture capitalist? This seems a lot harder than I thought. Why?

Answer: I wanted a new challenge in my career and wanted to invest money to help fellow entrepreneurs bring their visions to reality.

Me #2: Why?

Answer #2: Entrepreneurs need help and I think I have something besides money to help them achieve their dreams.

Me #3: Why?

Answer #3: Entrepreneurs can change the world and we need their help now more than ever. I draw inspiration every day from my job and can’t think of doing anything else.


By the end of the exercise, I quickly remember why I changed my career, set out to learn a new set of skills and took on the risk of co-founding a venture capital firm. I love challenges. I love trying new things. The idea of building something from the ground up is invigorating, exhilarating and above all rewarding. Most importantly, I get to work with the best and brightest entrepreneurs in the world and watch (and help) them chase their dreams.

Wow…. now I remember what I am trying to do. Now I am reconnected to my entrepreneurial vision.

The beauty of the exercise is its simplicity. However, it is only as effective as you challenge yourself to go deep on the “why.”

Staying connected to your vision might be the hardest part of being an entrepreneur. Seriously. So many ups and downs will come your way that you might have trouble remembering your first name let alone recalling what your original vision was for the journey.

The next time you are feeling stressed, challenged or are thinking of giving up, find a quiet space, put your phone away and try the “three whys” exercise.

I bet you will feel a renewed energy, a sense of purpose and clarity of thought and purpose. Give a try and let me you if it worked.

And always remember – if it was easy, anyone could do it!

P.S. if you haven’t taken the entrepreneur survival test – you need to!


Monkey Masters: Jason Dorsey

Monkey Masters: Jason Dorsey

For my third interview of Monkey Masters, I am thrilled to interview Jason Dorsey.  Jason is one of the most interesting entrepreneurs I have ever met and his insights, experience and background are truly exceptional.  The list of Jason’s accomplishments is too long...

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