Great Entrepreneurs Make Tough Decisions

I read a quote recently that said “great investors write checks.”  As much as I agree with the statement, I would like to take a different angle on it.

Great entrepreneurs make tough decisions.

I firmly believe in this statement, have lived it myself, and currently observing it with the CEO of the startup I am working with now.

Although elementary, making and acting on tough decisions can be the difference of life or death for a young company.  Decisions like:

Whom should I hire?

How much monthly burn is appropriate at this stage?

Should we raise money?

If so, how much do we raise now?

Whom should we take investment from?

Should I let that mediocre developer go?

If so, what will we do afterwards and how will we replace them?

Should we stay where we are or move office space?

How much should I pay my employees?  

How do I keep them happy and not lose them to another company?

All these questions – and many more – can haunt leaders of young companies if not acted on in a timely manner.  What the leader ultimately decides – and when – will determine what happens and if it’s a positive or negative outcome.

Most just sit and wait.  Most founders try to not think about or address the tough issues at hand, hoping they will just go away or take care of themselves.  I find most people are risk averse, hate confrontation and don’t like delivering bad news.

Bad mistake.

And that is why most startups fail.  Typically the death of a startup is not lack of product-market fit, buggy app or failure of proper manufacturing.  It’s lack of leadership.  It’s the fault of the leader in not quickly addressing problems when they arise, and not giving the rising challenges mind space when demanded.

What would you rather do: let one troublesome employee go or ultimately lose the entire team?


Life (and business) is simply a set of decisions.  I view it as a decision tree, or a series of thousands – even millions – of forks in the road.  You approach one, observe and evaluate at the options in front of you, and quickly make a decision.  Upon which you are then presented with another fork in the road – another decision to make.  By doing the same thing over and over again, an entrepreneur evaluates any situation quickly, gets it out of the way and then is free to make another decision.

That’s progress.

What tends to happen is most decisions end up with a positive outcome.  Will some quick decisions lead to negative consequences? Of course.  But then again, now the entrepreneur is presented with another opportunity to choose a better outcome this time around.

Where I see entrepreneurs go wrong is when they freeze, taking too long to evaluate and act on the decision.  Sitting and thoroughly evaluating a specific scenario may make sense in certain circumstances and help entrepreneurs make the right decision but generally speaking, entrepreneurs who act quickly and make decisions are highly rewarded.  Interestingly, when asked what they regret about their startup experience, former founders most frequently say they took too long to make highly important decisions like hiring, firing and shutting down or exiting the company.

Why do I agree?

Well, by definition the more decisions (opportunities) one has the more chances (opportunities) they have of finding success.  It’s called increasing your luck surface area.  Making quicker decisions will lead you to making even more decisions, increasing your opportunity to get lucky and moving yourself and your company forward towards success.

Most of the time, sitting and waiting for something to happen – for the challenging issue to take care of itself – will only result in…. nothing!  

Image courtesy of Flckr user Eric Vondy

Should Founders Advise Other Founders?

I have recently found myself in the advisory role with a number of other early stage founders.  As I spend my time hearing about their story, their pitch, their business plan and their go to market strategy as well as their challenges, it usually occurs to me I am in a unique position and greatly appreciative of the opportunity to help another entrepreneur.

Mentoring and advising other founders gives me a chance to look at different markets and separate businesses – how they are modeled and structured.  It allows one to peel away the layers and look at what makes the market work, who’s involved and where the areas of innovation may lie.  It also gives me a lens into how another person approaches their entrepreneurial craft – which although I am the mentor and they are the mentee I still learn a lot!

No one is cut from the same cloth – especially entrepreneurs – so these experiences are vital to you (as a founder) as well as a person and friend.  I would encourage you to take the time to help others through mentoring and advising.  Like working out, it stretches you in ways you wouldn’t otherwise stretch, and strengthens “muscles” usually left dormant.

Advising allows you to jump into someone else’s business and wrestle with problems, only to be able to jump back out and not have to fully deal with them.  You then get to watch from the sidelines as the entrepreneur goes on and makes their own decisions.  You simply observe the outcomes.

In this way, you become a more well rounded entrepreneur and business person since there are constantly new things to learn about technology, innovation, markets, customers segments and the art of entrepreneurship in general.

I look forward to advising more founders and would encourage you to as well.

Jumping (Back) Into The Water Is Tough

After an extended break from writing this summer I now find myself having a hard time getting back in the groove.


Well, for one thing I rolled out a new company called Coinme, which is in the bitcoin industry.  It’s going well but it had most of my attention in the late spring and early summer.  I also jumped onboard this summer as Director of Business Development with a new startup called Knotis that is developing really cool tech for the local commerce space (steady paychecks are where it’s at!)  Things are going well and I intend to write about Knotis as well.

So I’m a busy guy helping to build a few different companies at the same time.

Also, not to be lost in it all this is the beating my MacBook took this spring.  After an event I organized I walked over to my laptop only to discover a beer had been spilled directly onto my machine.  When I found it, I picked it up and beer was dripping out of the bottom of it!

Needless to say I was very upset.

The next day all I got was a black screen when I tried to turn it on.  Turns out, after letting it dry everything was alright, except the esc, tab and shift keys don’t work.   Try typing and capitalizing words (shift key) with your right hand when you have done it with your left your entire life… not fun.  And so I stayed away from long form writing because it felt weird and I needed to learn how to do it the other way.

Well, I’m back.


I want to get back into the habit of writing a few times each week.  It’s like exercise, we all need it and it does wonders for our health.

So look for new posts as I plan on picking back up on my writing about entrepreneurship, tech, life as a founder, and other things that catch my eye.

Kyle Kesterson Answers The Question: What Is Creativity?

This short piece comes from one of my founder friends here in Seattle, Kyle Kersterson of Freak’n Genius.  Kyle – one of the most creative and nicest people I know  – has been growing his startup for a few years now and from what he has told me of late they are destined for great things.

In this video he talks about Creativity and how anyone can be creative with anything in the world they find around them, all it takes is a little imagination.

“We should be MAKING FUN of everything in the world.”  

Take a look….

This Is One Of The Best Commencement Speeches EVER

Well, this is an insta-classic.

U.S. Navy admiral and University of Texas, Austin, alumnus William H. McRaven returned to his alma mater last week to give seniors 10 lessons from basic SEAL training when he spoke at the school’s commencement.

McRaven, the commander of the U.S. Special Operations Command who organized the raid that killed Osama bin Laden, stressed the importance of making your bed every morning, taking on obstacles headfirst, and realizing that it’s OK to be a “sugar cookie.”

All of his lessons were supported by personal stories from McRaven’s many years as a Navy SEAL.  You need to watch the 20 minute video to grasp the magnitude of his words, but here’s the list of his 10 lessons.

If you want to change the world, start off by making your bed.

If you want to change the world, find someone to help you paddle.

If you want to change the world, measure a person by the size of their heart, not the size of their flippers.

If you want to change the world get over being a sugar cookie and keep moving forward.

If you want to change the world, don’t be afraid of the circuses.

If you want to change the world sometimes you have to slide down the obstacle head first.

If you want to change the world, don’t back down from the sharks.

If you want to change the world, you must be your very best in the darkest moment.

If you want to change the world, start singing when you’re up to your neck in mud.

If you want to change the world don’t ever, ever ring the bell.


The Old Wise Man And The Eager Young Chap

“….But I thought it would be easier than this. It’s really hard.  It’s tough and I don’t know what I am doing.  What am I supposed to do?”

A long time ago in a far away land an old wise man and an eager young chap were taking a walk and talking about life.  The young chap was eager to do great things in the world but seemed to stumble each time he pushed forward.  Desperate and in despair, he sought out the wisdom of the old village elder in hopes to find his answer.

SadhuThe elder – being the oldest and wisest man in the village – had heard such worries before and was no stranger to these youthful cries.

“Young chap, I sense you need to understand something very important about this life.”

“Huh, what’s that?” The eager boy snuffed and wiped his head to push his hair out of his face.

“What you don’t realize is your most pressing and worrisome issues are everyone else’s least pressing and worrisome issues.  They are yours and yours alone to figure out.  No one can tell you what to do, you need to discover the answers yourself.”

“Wait, what do you mean?  You don’t care about me and my problems?”

“I didn’t say that, young man, but I do think you need to look deeper.”

Confused, the young boy lowered his head and looked down towards the ground.

“Do you know what I am struggling with right now, just as you have come to me with your hardships?”

“No I don’t, what?” the young chap whispered.

“I have lived a long time, many years more than you have.  I fear my time on this earth is coming to an end very quickly, and although I have lived a blessed life I am having a hard time letting go of life.  I love my family, my community and all the great experiences I have encountered.  Even as you notice me struggling to walk up this path, my heart is as young as yours and desires exactly what your young heart does.  I cannot let go of life but will be forced to very soon and this troubles me.  And because of that I live each minute as if it is my last – just as this moment is the most important thing to me right now – and I choose to not have a care in the world.  I put my entire heart and youthful energy into experiencing everything about this moment so as to take in as much as I can before I go.  I turn my biggest fear into my greatest strength.  And in that way, I fully live and discover things I would normally have not.”

“I sense you aren’t doing that, are you my young chap?”

A long silence fell over the old wise man and the young chap.

After a while, the young chap responded.  “No… ummm, I’m not.  I think I’m scared.  I think I’m scared of what others would think about me if I lived without any limits or cares as to what they thought.  What if I fail?  What will they think then?”

The old wise man stopped, turned and looked the young chap in the face with his piercing blue eyes and said “Son, never forget this lesson, it is you who cares the most about if you succeed or not.  It is you who is holding yourself back.  And if this is true for you it is true for the rest of the world.   No one cares but only about themselves.  You must go forth and do everything you dare dream of with little worry about what the rest of the world thinks.  They are too busy searching for their own village elder to help them figure out why they are struggling…  just like you.”

And with that, the wise old man vanished through a small path between two trees and was gone.

Smiling and a bit fazed the young chap scratched his chin, thought about the wise words for a moment and with a renewed look of determination walked the other way.