Why Every Entrepreneur Should Listen to Jazz

Originally published at Unreasonable.is

This is a song of mine called Twos. I am playing saxophone with a vibraphonist named Mark Clifford and drummer named Colin Stranahan. Two of my best friends and favorite musicians on the planet.

This is jazz, but this also is also an audio-metaphor for entrepreneurship.

As an entrepreneur, you are an artist. Art is the willingness to go fearlessly into the unknown and create. A dedication to look past the fear, to take risks in search of something beautiful, and to find possibility even when there seems to be none. Where others see sticks, entrepreneurs see a fire. What distinguishes entrepreneurs from the rest of the business world is their drive to explore the environment around them with great intention.

As an entrepreneur, you are an improvisor. Improvisation at a high level is a sophisticated process. An improvisor takes in all available information, deals with that information from an educated perspective, makes a choice, and then acts.

Great jazz musicians improvise in the language of music. Great entrepreneurs improvise in the language of business.

We build things together. When Mark, Colin and I played “Twos”, we were simply three people, working together, supporting one another, in order to create something greater than we could build individually. As you’ll see in the outline below, there was a plan. That said, much of the performance was left undetermined. In order to be successful, we had to go together into the unknown, be open to whatever happened, and trust each other as equal partners in the creative process.

This is a single, continuous recorded performance. There are no edits. No auto-tune! We are playing this in real-time, together.

Take a look at the “plan” for Twos:

  1. 0:00 – Mark plays the 1st melody on the vibraphone.
    1:07 – I play the 2nd melody on the saxophone. Mark continues to play the 1st melody.
    2:37 – 4:02 – We’re improvising. In jazz there are often structures that are maintained during an improvisation. In this song, we are simply improvising. We don’t know what will happen here.
    4:02 – I continue to improvise while Mark plays the 1st melody again.
    4:53 – I play the 2nd melody again while Mark continues to play the 1st melody.
    5:16 – Mark and I play the 1st melody together.

Jazz musicians write compositions. Entrepreneurs write business plans. To an entrepreneur, a business plan is simply a place to start. Entrepreneurs look at the world from an artist’s perspective. They step into the unknown, discover new possibilities, and create change.

Entrepreneurship is tough, and some days are tougher than others. The next time you’re scratching your head, excited about a new idea or pulled in a thousand directions, listen to this and remember that jazz is proof that it’s possible to start from inspiration and make something beautiful. Proof that when people build together, it’s amazing. Proof that through integrity, transparency, and supportive collaboration you can do great things.

All of the arts are metaphors for one another. This kind of cross-pollination gives us perspective and enriches our lives in unexpected ways. In taking the time to develop relationships with art forms outside of your own, you will make discoveries that will support you on your journey to becoming a great entrepreneur.

You are an artist. Go into the world, into the unknown, look for possibilities, and create!


This is What I Learned Today

This is what I learned today. 

You figure out the "why" which is as easy as it is hard.

The you figure out the "how" - which leads you to a "what." 

Then you DO the "what." 

THEN...and this is the important part....

When you've finished doing a "what," you STOP doing that "what" and you start doing the "next what."

You can always go back. You have to go forward. 

Running really fast in circles is only a great way to get tired. 

That is what I learned today. 



I love learning, because it is something you never finish doing.

You learn what you learn, whether through sadness or fun or hardships or love, and then after you're done doing that, you just start learning whatever there is to learn next.

I always feel like the thing to do is to hurry up and learn your lessons. (To really learn them, of course, but not waste time not learning them). Not so much because those lessons will be learned, but because then you get to see what the next lesson will be.

I love learning. I'm hooked on seeing the next problem. 

For me, learning is like climbing mountains. The best part of climbing a mountain is not just arriving at the top, it's what you get to see when you get there. And if you love climbing mountains, then there's nothing better to find when you reach the top of one mountain than another mountain you haven't climbed yet.

I think that - like climbing mountains - the more the you learn, the better you get at learning. 

If you climb enough mountains, you get good at climbing mountains. How different can mountains be, really? At some level, every mountain is probably just another mountain. Sure, they're all unique and challenging in unique ways, but they are only ever challenging in the ways that mountains can be challenging.

I think learning is the probably the same. That learning is challenging. Of course each lesson is unique and challenging in unique ways, but only in the ways that learning can be challenging. 

I love learning, but sometimes, I think it makes me a glutton for punishment. 

I stay with learning even when it gets hard. Especially when it gets hard. 

I can't get myself to tap out. I take whatever beating I have to take in round 4 so I can come back with the knockout on round 9 and learn the damn lesson. 

I'm hoping that one day I'll get better at finding the knockout in round 2 or 3. That I'll learn to see situations more clearly and understand the lessons I'm learning more quickly. 

I love the idea of the one punch knockout. That - if only once - I might see my life with clarity enough that I get to learn a lesson without having to take the beating. In and out in round 1. The crowd goes wild. 

I love learning because it's something you never finish doing. 

I figure, we all have to do something while we're here. If that's the case, it seems nicest to pick something you won't have to stop doing when you get old or busy or tired or any of those things that people "get."

So, I'm all the things I am. A musician, a teacher, a friend, a son, and a bunch of things more.

I feel lucky that I'm a lot of things. 

I have a lot of opportunities to learn and I love learning.

Four Short Thoughts

I like laughing about new things and looking at things of depth. My favorite moments, though, are when those two things happen together - to see a old truth in a new light or a new truth in an old light. Those are the best laughs and the deepest insights.

It's hard to find solutions through 1 or through infinity, because, then, all you are left with is luck.

First comes the inspiration which is inspiring. Then comes the work, which is work.

Find something you believe and then do work. Then you find someone else who believes in it, too. Then you work together. Then you find more like-minded people. Then the work goes more quickly. Soon, there is change.

Laughter and Acceptance

I've been writing about my thinking lately and I've found that the writing feels much stronger when I ask questions rather than make statements. For example:

I think there is a difference between: 

Stating: "People are inherently good." 

And asking it as a question: "Perhaps, people are inherently good." 

That there is a positionality in the statement - a point of contention. It feels dogmatic. Absolute. How could I possibly know what is true? For generations, people have "known" the "truth" and this "knowing" has led to things like sexism, racism, war, and a million other sources of pain in the world. 

So, why, then, does it feel better to write about my thinking by asking questions than by making statements?

 I wonder if by asking a question, I am essentially removing myself from the equation. I'm giving the reader the opportunity to ask the question for themselves and by asking the question come to their own answer. 

"Yes," "No," "I don't know," "The Bush Administration," "Russia, 1942," "What is Homer Simpson?" Whatever their answer, it's alright. I've taking myself out of the running to be "Mr./Mrs. Super Nerd of Knowing-dom." 

I've been thinking that maybe we're are all responsible to discover the "truth" on our own. That we can have help, - and there is definitely seems to be help available - but that ultimately, we are responsible for our own positionality in the world. That we have to discover our path in life through realizing our respective truths through our own experiences in our own lives. 

I think there are two ways to accept a new truth: To laugh at it or to state it. Sometimes it's scary to accept something as true, but if you can laugh your way there, you get to trick the ego into not noticing its death.

Why does everyone like the fat, happy buddha?

Because its way more fun to laugh yourself to enlightenment than it is to starve yourself there. 

I wonder if that's also why people love comedians like Louis C.K. They help people find their truth, but the easy way.


The sweetest (if not maybe the most powerful) way in which we can support each other is by helping to preserve in one an other that child-like sense of wonder.

Life lived from that space of wonder is miraculous and beautiful. It inspires us to learn to think differently and to seek out new possibilities.

Life lived without that sense of wonder and amazement becomes predictable, painful, and essentially uninspiring.

Action without inspiration is empty.

So, help the dreamer to dream. Those dreams are the seeds of inspiration. 

Those dreams are the seeds of their joy. =)