The Tales We Tell Ourself About Failure

One thing we humans do really well is self doubt.

In the last week I have had two separate conversations with fellow founders about the grave situations their companies are in, how they are staring “defeat” right in the face and don’t really see any other option than to move on.

Both people are down and out right now.  And rightfully so… They have put years of blood, sweat, tears and money in pursuit of their dreams. They feel troubled with the fact that they didn’t succeed in the way they felt they could, didn’t build a meaningful and growing company. I know what they are going through, I have was there a few years ago and had a hard time knowing when it was time to pull the plug.

My advice to them is this:

It’s okay. You think the company (and you) are a failure because you have to move on and go do something else. You may have put your self worth into the company so much so that as the company faces a failure in operation you are feeling like a failure in life. You might be feeling a bit embarrassed because of all the things you said to your friends, family, coworkers, and industry partners now make you look at best untrustworthy, and at worst fraudulent.

These are all normal fears and feelings. They are all accurate and a normal part of the grieving process of a failed attempt at a startup company. But these are all fairy tales we repeat internally.


The reality is the very fact you set out and tried something unique and different is the success in this story. The very fact that you had the courage to attempt something most people would be afraid to do is the success. The fact that you were looking to be part of the solution rather than part of the problem is the success. Most likely your entrepreneurial decisions inspired at least one other person to jump up and start their own entrepreneurial journey. And further, maybe that person and their project turns out to be a massive success, impacting millions of people around the world, lots of that due to you. You may never know… but it’s a possibility isn’t it?

Many people lean on the stat that something like 75-90% of all startups fail, they don’t reach a point of self sustaining profits. I feel this stat is misleading since it only measures financial outcomes of each entity. Is the company alive, or dead? Red or black? Running or shuttered? Successful or not?

A better measure – albeit much more difficult – is to evaluate the impact each person and their endeavors have on the people around them. I guarantee if we were to measure the impact and success of each founder who ventures out on their own by looking at how they affected, influenced and inspired others we’d be talking about a whole different number. I bet it would possibly be the inverse, which would be quite inspirational. We’d be saying something like “Only 10-15% of startups really fail to impact the world so you must go and do it!”

To all those who are currently struggling with what to do and which decision to make for your company right now, heed this advice. The only failure in your situation would have been not choosing to attempt the impossible, since that is the only reason you are able to sit in the chair you are sitting in right now, reading this on your device you are holding in your hand, sipping the drink you are tasting right now, and driving in the car you just drove in.

Success is simply choosing to attempt the impossible and inspiring others to do the same.

How To Get Out Of A Rut

We all know the feeling of being in a rut: tired, frustrated, challenged, stressed, worried, uninspired, etc.. It’s okay to fall into a rut at times.  But what can you do to get out of it and return to your former self?

I found answer lies in doing that very thing you are not excited to do.  Whether it be a sales call, a coding project, tough conversation with an employee, yard work, workout, or whatever… embracing the pain, leaning in and executing on the one thing you seem to be shying away from is the best way to rid yourself of the rut. Overcoming the issue and achieving something again triggers a dopamine spurt and kickstarts your energy. In The Road to Success is Paved with Discomfort, Leo Polovets describes the same concept as one of his secrets to success. Do what feels uncomfortable:

If you want to be successful, you have to be willing to push through discomfort. If you’re a founder, you’re going to have to fire people, you’re going to have to talk to customers and sometimes hear negative feedback, and you’re going to have to make cold calls. If you’re not willing to do those things — or at least hire someone else to do them — then that’s okay, but your likelihood of succeeding will drop dramatically. At the end of the day, you have to ask yourself what’s more important: your comfort and your ego, or your success and your company’s success?

So true.  So true.plyazh-bereg-more-okean-volny

Recently I encountered this feeling with my day job, as well as with all my other projects. I wasn’t in a traditional rut, per se. But the great weather of the summer here in Seattle teased me so much I gave in and took it a bit more easy in the months of May through August.  Although I had a lot of fun, that a little voice inside my head was nagging, cursing at me to get with it and get back to work on all the various projects I have going.

Of course, I did what was required and expected of me at work this summer but I knew I had more in the tank.  Yes, I started writing again this summer after taking a number of months off but I could have written much more than I did. Founders RAW was sitting on the back burner for many more months than I wanted it to, purely due to laziness and lack of attention.

I now realized I fell into a comfort zone, and once in that zone I started telling myself all sorts of things to defend my laziness.  I started to shy away from working harder, not driving the company I work for and my projects forward.  I shied away from the discomfort and paid the price for it – falling into a sort of weird rut.

The farther I go along on this journey the more I understand success is really just learning to leverage the ebb and flow of energy similar to the flow of the ocean tide.  Sometimes you are up, driving forward, leaning into discomfort and making things happen.  And sometimes you are leaning back, relaxing, enjoying your take and being lazy in the comfort zone.

The beauty is once you start to identify those ebbs and flows of your energy you can start to time it right, and use it to your advantage. The best way to break from ebb and back into flow is to do the very thing you are not wanting to do, to start the thing you seem to be putting off.  Do it, and you’ll see it wasn’t as hard, scary, difficult or challenging as your mind was telling you it would be.

Summer ebb-ing is fine and I have enjoyed it. Now it’s time to jump back into the flow.

Founders RAW Is Looking For A Seattle Based Videographer

We are gearing up for a new season of Founders RAW and I’m looking for a new videographer.

This individual needs to be local in the Seattle area and familiar with both recording, post production and slicing of longer videos into short clips.  You can get an idea of how we shoot Founder RAW by viewing of our previous videos here, as well as the video below.  If you are interested, or know of someone who might be interested in being a part of a fun team producing great entrepreneurial focused videos, please reach out to me asap.

  • Part time position, estimated 10-20 hours per week
  • Portfolio and previous video production experience strongly recommended
  • Compensation depends on experience as well as project sponsorship status
  • Establish yourself as an experienced video professional within the tech industry
  • Opportunity to meet well established CEO’s and founders of tech startups who possibly have other video needs

Is It Fair That Founders Get The Lions Share of Equity?

Something has bothered me for some time and its just now starting to get talked about.  Below is not a rant, but rather an exercise in thinking about fairness in compensation.

Founders receive huge amounts of equity in the companies they start, yet over time as more and more employees join on and work incredibly hard to help grow the business into a successful enterprise the percentage ownership (cap table) doesn’t reflect adequate compensation.  Why is it that an employee that joined just a few months or a year after the founder receive orders of magnitude less equity – and cash after a liquidity event – than the original founders?

Does it really matter if you were there first and if it was your idea to begin with?  If so, how important and impactful is it?  Millions of dollars?  Billions of dollars worth of difference?

Yes, founders do take inordinate amount of risk in starting a new venture and they should receive compensation to reflect that.  But when we are talking about $billion+ outcomes we then start to talk about income inequality on absurd levels.  The difference between a founder receiving $1 billion or $2 billion is not the same as taking that extra $1 billion and spreading it over 100 or 500 employees – that which makes quite a bit of difference in each of those people’s lives.

The fact is early and middle employees are hugely important to the success of a startup and should be compensated accordingly.  More so, they might even be vital to the company’s success, such as a Director of Sales or VP of Engineering may be in helping a gangly startup grow up into a mature and profitable company.

A recent podcast from Andreessen Horowitz covers this issue, and touches on how founders can think about structuring their equity grants a bit differently so that they can appropriately compensate early and later employees.

Anyway, listen to the podcast as it covers a lot of points in this touchy subject.

The Very First Thing To Do When Opening Your Eyes Each Morning

Close them for another 10 minutes.

The deeper I go in this industry the more I realize success is determined by the quality of my mental fitness.  It was with that realization I recently started the practice of mediation. This new direction might come to some as a surprise, as it does with me. I’m not a very “spiritual” person and have up until recently thought of mediation and other methods of silence with a “not my kind of tea” nonchalance.

What we view as different we tend to be afraid of and to be very honest I was afraid of meditating. It was just foreign to me. Yet that might be why I found myself in a situation where I was desperately needing it!

I realized in my first month of meditation it’s not as weird, shamanic, spiritual, or cult-like as I thought.  In fact, I realize now that it quite possibly could be the secret to a happy and successful life no matter what country you live in or what religion you claim to believe.


With so much stimulation, media distraction and impulsive opportunities today, clarity of thought is our most scarce resource. By not taking the time to center oneself in their purpose before they start their day, one may find each day harder and harder to complete. I felt this overcoming me during the last year or two – the subtle feeling of losing my compass and lacking the fulfilling energy of pursuing a direction that aligns with a purposeful life.


So with a suggestion from my girlfriend – who has been meditating for more than 10 years and glows with its benefits – I jumped in.  Boy do I have a long way to go.  I haven’t established a strongly held habit yet but here’s what I learned in the first month.

1. Calmness.  I found I was becoming more tense as the years went on, and given my laid back nature this was starting to really bug me.  It probably has to do with the nature of our industry and the difficulties of being a founder or working for an early stage company.  As I started the practice of meditation I began to feel the tension ease off a bit.  It’s still there to some extent, but I am now learning how to deal with it and shift the excess energy to a more positive area of my life.

The main reason I feel better is with the consistent nature of meditation you are able to think, ponder, and review; this leading to an adequate evaluation of the difficult things happening over the course of your daily life.  Stress overcomes us not because of something that happens to us, but because we haven’t adequately perceived the reality of the situation and are uncertain of what we are going to do about it.  We lack clarity. My calmness has resulted from taking time each day to let my mind wrap itself around the challenging things developing in my life, and allowing my mind time to determine the next step.

2. Centeredness.  I never really knew what this term meant before starting to meditate, but now I understand the power of allowing your mind to focus on certain aspects of your life, steering away from harmful and negative things while steering towards ones more beneficial. It actually takes effort to think about what you are doing here on earth, what you want to accomplish, how you want to live each day, how you want to treat people each day and the trajectory you want your life to take.  All this becomes clearer when one consistently starts their day in deep thought.  Although just a month in, I am feeling more centered and aligned and I can’t wait to see where the next 6 months or year directs me.

3.  Slowness.  It seems like things are going faster and faster each day.  Computing power speeds up each year, and computers just keep getting smaller and more ingrained into our existence.  Emailing went to text messaging.  Taking pictures with a digital camera and uploading to a website went to snapping a pic and sending a quick Snapchat to a friend. We expect to grab our phone and instantly find a restaurant whenever we are hungry. We also expect a response from someone we communicated with – immediately.  Each day seems to be speeding up and taking our whole society with it. It’s no wonder people are so stressed out.

Meditation has shown me the power of slowness and what it can do in a world where people and ideas are flying by at the speed of light.  Slowness allows for thoughtful consideration of the world around you. It allows for deeper comprehension of all the things happening to you and around you.  There are many things in our world that are simply too complex to fully grasp only after a few seconds or immediately after a meeting.  Not taking the time to allow your mind and body to fully comprehend the world around you is a grave mistake.  Through slowing down and practicing mental clarity each morning I set the tone for a stronger, more agile, more flexible mind which now has a better understanding of when to make quick hasty decisions or to slow down and contemplate all angles of a situation.

Take it from someone who used to shrug off the concept of meditation, you are making a huge mistake by not starting your day with your eyes closed in deep thought about the day you are about to experience.

How To Approach A Startup When Looking For A Job

A friend recently asked me a good question:

What’s your feel on whether or not to contact a company without a clear position opening. There are a few startups I really dig, but they don’t currently have a job opening that fits my role. Is it worth it to shoot them an email to introduce myself and possibly talk about carving out a role if they like me enough? Or should I not waste my time?

My answer:

Best to naturally network and get to know people in real life like you have done with me, rather than reach out cold knowing they aren’t hiring for your skill set and hoping for the best. They’ll probably just think it’s spam and not respond – that’s what I do.  Most companies/startups hire for personality + skillset, and the only way to find that match is to meet them first and get to know them over time, illustrating your value.  So.. find a way to get to know the founders and employees of the startups you like first, then work the angle of getting a job at their company.

Reaching out to startups in an effort to connect and get to know the company is definitely a great idea.  But cold emailing thinking you will be able to land a job is a longshot at best, and shows you have no savvy way to integrate yourself within their operations.  Especially if they display on their website they are only hiring for certain positions- and you don’t see a good role that fits your skill set. (If they DO show they are hiring exactly for what you are great at, by all means reach out to them!)

The secret to getting hired at a startup is to get to know the people within the company by any means necessary. This effort will provide an opportunity to determine if you are a good culture fit – and you might find out there isn’t a good fit after all.  And just like a lot of things, that happens over time. It’s all about learning as much as you can about the founders, the employees, their product and what type of office environment they have. No startup I know of will keep the best engineer in the world on staff if they are also the biggest asshole in the world.  And vis versa, no person will want to work with a company/founders who have no idea how to treat employees with respect.

Seek First to Understand, Then to be Understood.

And that is the root of networking – connecting with people in your industry.  “Networking” has gotten a bad rap and has been misconstrued in today’s fast paced transactional world. It’s not about the one night stand and getting hired as soon as possible.  It doesn’t happen overnight.  It happens over time and over repeated positive interactions with various people within the startup, to the point where numerous people are asking “what does that person do and why don’t they work for us?”

So if you want to get hired by great founders in the industry, get out there and make sure they know who you are and why they should want you to join their team.

Dealing With Startup Uncertainty

I was asked a great question yesterday from someone who is just beginning their startup journey:

“How do you handle the uncertainty of being a founder?  I mean, there are so many unknowns how does one even start?”

long-pathThere are a few ways to take this question but the one I see and hear the most from people is from the angle of how different a startup is from a typical job.

Most of the time a job has a description, some requirements, parameters, metrics to be measured upon, and a boss to report to. In and of itself, a job is limited and defined.  And most people are comfortable with being limited, since the limitations that are placed upon them at least provide an outline of the playing field where they will have to perform.  Do what’s expected of you and stay.  Don’t do what’s expected and you’re let go.

Requirements + measurement = outcome.

This is not so in a startup, or is not as apparent I should say.  The unknowns are vast and immense – such as what market are we focused on, what’s the product going to look like and how is it function, whom should be my cofounder(s), what ownership levels does everyone receive, what happens when people aren’t using our product, or when a larger competitor copies what we are doing, when do we know when to pivot or quit, when should we sell, etc…

In my opinion, the best approach to dealing with such uncertainty is to understand what a startup is and what the journey is all about.

According to Steve Blank, a startup is  “an organization formed to search for a repeatable and scalable business model.”  Clearly he’s stating that during the early years of a startup everything is uncertain.  The whole purpose of a startup is to go from uncertainty to certainty – or from nothing but an idea to a repeatable and scalable business model, to use his words.

The secret to being an entrepreneur is becoming comfortable with being uncomfortable.  Just as Lewis and Clark set out from St. Louis towards the west, they had no clue where they would end up.  They just went west!  They were comfortable with not knowing what they would encounter during the journey or where they would end.  Lewis and Clark were explorers, but they were also the epitome of an entrepreneur.

Coming to terms with the fact that thousands of decisions lie ahead in the future and are totally unknown today is the #1 thing founders need to do on the outset of starting a company.  And simply focusing on the two most important decisions sitting in front of their face is the 2nd most important thing a founder must do. Tomorrow, two more things will present themselves and will need to be addressed, and you will focus your attention on those.  Outside of establishing a vision and plotting the direction of how to get there, most other aspects of building and growing a company will fall into place.

How do you climb a hill?  One step at a time.