Give Yourself Permission To Fail

Giving myself permission to fail has been a reoccurring thought as of late, and reading a recent post from Keen.io CEO Michelle Wetzler really solidified it for me.

After a few years in the back seat helping others in the building process I am back in the founding position. As I get back into the drivers seat I am reminded that my mental approach to this next journey determines so much of my trajectory and overall success.

If I am scared to fail, I most likely will fail. If I am worried we’ll go broke, we most likely will go broke. If I think I am not good enough to be CEO and not fit to lead a successful company, I most definitely will be those things.

BUT if I reverse that thinking I can reverse the psychology as well.  If I believe I’ll be successful, I most likely will. If I am confident in our finances, we most likely will stay afloat. If I think I am good enough to be CEO and fit to lead a successful company, I most definitely will be those things. And if I open myself up to possibility of failure I see that it is not that bad.

Michelle sums it up perfectly.

Giving myself permission to fail has been one of the most liberating, stress-relieving, and rewarding things I’ve done in last year.

The only way we can become a truly great company is if we open ourselves to the possibility that we might not be.

And you know what? It’s okay if we’re not. If Keen busts, we’ll all find new grand adventures. Some us could start a new company together, or get boring jobs at big co’s, or sail around the world, who knows, the world is full of lots of amazing opportunities.

…To give yourself permission to fail, you have to untangle your ego from your work. Having your ego tied up in your work is a handicap. You can’t think strategically or take risks when you and your personal well-being are on the line.

Basically, embracing reality frees you up to be everything you were meant to be. By not being paralyzed by what could happen, you are free to create what should happen.

This is an important lesson for founders, especially first timers who fall victim to impostor syndrome. Wikipedia defines it as “a term coined in the 1970s by psychologists and researchers to informally describe people who are unable to internalize their accomplishments. Despite external evidence of their competence, those exhibiting the syndrome remain convinced that they are frauds and do not deserve the success they have achieved.”

Another way to think of impostor syndrome is to be so frightened by your future (be it positive or negative) that you simply don’t believe you are doing the right things or are the right person for the job. You question every little decision you should make, you aren’t sure if you should go left or right. You think your peers see a different version of you, a lesser qualified person sitting in the front seat pretending they know what they are doing.  You start believing you are an impostor and thus end up failing in the end.

This is all wrong and can be mitigated by giving yourself permission to fail before you even start. That way you are free to make the correct decisions, knowing failure is just part of the process. It sounds crazy but a simple change in perspective makes all the difference. I have found the best perspective is that the world is full of lots of amazing opportunities, and if you fail at this one there’s always the next one.

That, my friends, is why I am back in the drivers seat.

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Coasting To Perfection

Am I doing all I can each day to reach my own pinnacle in life? Have I done everything possible to become the person I was created to be or am I just coasting along the highway…?

A post today piqued my interest and spurred this intense inner monologue. MG Siegler writes about a recent SI article on Michael Phelps which details his comeback and rehabilitation from alcohol related incidents.  The article touches on a variety of events in his career but what jumped out to me was a very interesting and possibly troubling assessment by Phelps himself, where he simply admits he has never given it his all. Ever. Even after numerous Olympics and all the medal records he feels he under-performed and still has his best inside him. Siegler ties that thought back to all of us:

“we don’t often hear about someone at the pinnacle of what they’re doing also failing to give their all — and yet, that’s clearly the case with Phelps….. And so in a way, I think that’s a more interesting point from which to look inward. If you’re really fucking up and squandering your talents, it’s pretty obvious for everyone to see. But what if you’re only not “giving it your all” and coasting on doing the minimum to still be successful — even very successful? Or maybe not even the minimum, but something less than all you’ve got. I think a lot of people are guilty of this. Maybe even most people. Certainly I am, in some regard.”

So I ask you, are you just coasting through your life?

It’s a troubling thought if you really consider the question when its asked another way: will you ever reach your full potential with your current output of energy, focus and determination?

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I ponder this question quite a bit and maybe it’s the reason I have a number of current projects/companies ongoing in my life. It’s almost as if I can’t not do them. I don’t want to ever look back and realize I could have done more, that I should have applied myself more fully to the things and people in my life, and that I coasted lazily while others looked upon me with slight disappointment knowing I was fully talented and capable of greatness but in the end never doing anything worthwhile.

Wasted talent they’d say.

This is why I push myself to write even on days when I don’t want to or don’t feel like it. I want to follow my writing talent as far as it will possibly take me.

This is why I get in front of the camera and shoot more Founders RAW conversations.  Setting aside the enjoyment I get from doing them it’s not easy being comfortable in front of a camera and I believe people need to hear the messages we are putting out. I also want to follow my talent in media creation as far as it will possibly take me.

This is why I get on stage in front of hundreds of people each month and host Feature Friday events in Seattle – a monthly event which highlights 5 new up-and-coming area startups. This pushes me to become very comfortable on stage in front of crowds and calms the public speaking nerves, a wise move given public speaking is the #1 fear in the world.

This is why I push myself to build new apps and create whole new companies. I don’t ever want to find myself out of the loop on the latest trends, as well as sometimes it just takes a few cycles before the big idea takes hold.

This is not rocket science but I do these things so that I get better at them until a time comes where they are second nature to me. This is the 10,000 hours stuff Malcolm Gladwell talks about. It is said by the time the Beattles led the “British Invasion” with Beattlemania and brought their music into America they had already played together as a band live so many times they had eclipsed their 10,000 hours threshold and were very very tight as a band. That’s why they were so damn good so early on.

But it didn’t come overnight.

The Beattles believed – as I am starting to now – you are only as good as you choose to be. And “to choose” means you determine to do whatever it takes, however long it takes, with whatever means you have at your disposal to achieve you potential. Anything less is just cheating yourself and the greater world in the process.

Some have it easy you might say. They are naturally talented and without doing EVERYTHING THEY CAN they turn out to be Olympic champions and record setters. LeBron James, Michael Phelps, ect.. Simply more talented than anyone else. I say good for them.

But I am more impressed with the one who wasn’t God gifted with the most talent in the world yet works so diligently at their craft they become one with it, they become the legends we read about. The Wright Brothers. Steve Jobs, etc. The ones who came from nowhere, with no money and no connections, no Ivy League schooling, no Silver Spoon or lucky sperm club card to show off.

These people will it into existence. They are the ones we love to read about and crave to hear speak in public.

My guess is you fit that bill just as I do. So do yourself a favor each day and ask yourself if you are giving it your all – and be honest with your answer. My guess is you’ll be surprised at how much farther within yourself you can dig.

Founders RAW is BACK!

After a year long break, I am excited to announce we are back to filming more Founders RAW conversations.  We filled our need for a new film crew with the addition of Shinebox Films and quickly got to work to complete two new conversations.

For the uninitiated, here’s why I started Founders RAW:

“Founders RAW is actually an experiment.  As founders of an early stage startup we quickly realized how difficult starting a company can be.  And being part of the larger startup community in Seattle we discovered we weren’t alone in our crazy, mind-blowing experiences – apparently others have them too.  The idea started to form once we noticed the frequency of finding ourselves 30 minutes deep in truth sharing and wisdom dropping conversations with founder friends.  We wondered if others would be interested in what we have learned, so we figured why not to bring a camera.  I guess we’ll see what happens.

Founders RAW is a video blog with conversation style interviews focused on bringing out raw stories early stage founders experience in their challenging entrepreneurial journeys.  We invite founders to talk openly over a beer or a coffee about the “truth” of how they survive and grow their companies.  We post the full conversations on the blog but really, who has time to watch 45 minutes of video?  So we slice up the conversations and post nuggets each day as well as send out daily videos no more than 3 or 4 minutes long to blog subscribers.    Now we all can receive daily nuggets of the entrepreneurial truth.”

This year’s guest’s will include founders from Ghostruck, Unikrn as well as a prominent Seattle Angel Investor along with others to follow. You will see more on those when we complete the editorial process, but I wanted to highlight a handful of conversations we had over the last few years to get you back in the mood.

Brewster Stanislaw, cofounder of Inside Social

Marc Weiser, Founder of RPM Ventures

Simon Crosby, Founder of Bromium

Adam Lieb, Founder of Duxter

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.

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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.

Some Awesome New Resources For An Entrepreneur’s Daily Learning

No one knows it all.  When it comes to startups and entrepreneurship things seem to change so quickly generally accepted conventional wisdom is actually becoming obsolete before our very eyes.

For that reason I strive to stay up to date with the industry, what’s taught at the major universities like Stanford, and what young founders are learning in accelerators like YCombinator.

Here are some resources I have been using recently to gain more insight as a founder and entrepreneur in the tech industry.

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The Stanford ecorner is something I have been listening to for almost 6 years now.  They record one speaker each week addressing the class and then post it to the site the next week. Topics range from Creativity & Innovation, Opportunity Recognition, Product Development, Marketing & Sales, Finance & Venture Capital, Leadership & Adversity, Team & Culture, Globalization, Social Entrepreneurship and Career & Life Balance.  Stanford University’s Entrepreneurship Corner offers 3000 free videos and podcasts, featuring entrepreneurship and innovation thought leaders. I highly recommend it!

downloadStartup Class – Stanford CS183B, taught by Sam Altman of YCombinator.  CS183B is another class taught at Stanford. It’s designed to be a sort of one-class business course for people who want to start startups.

Videos of the lectures, associated reading materials, and assignments will all be available here. There will be 20 videos, some with a speaker or two and some with a small panel. It’ll be 1,000 minutes of content if you watch it all.

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Reboot.io (podcasts) is a new resource put together by Jerry Colonna and his business partners.  Jerry Colonna is an executive coach who uses the skills he learned as a venture capitalist to help entrepreneurs. He draws on his wide variety of experiences to help clients design a more conscious life and make needed changes to their career to improve their performance and satisfaction.   The Reboot podcast will showcase the heart and soul, the wins and losses, the ups and downs of startup leadership. On the show, Entrepreneurs, CEO’s, and Startup Leaders will discuss with Jerry Colonna the emotional and psychological challenges they face daily as leaders.

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The A16Z blog and podcasts are one of the best new daily resources an entrepreneur can read.  As previous entrepreneurs and now some of the most popular venture capitalists, they provide their unique views of the technology market that will help any founder gain valuable insights on trends, investment thesis’ and the newest startups that are raising money and making a dent in the world.

ENJOY.

The Secret To Launching A Successful Startup

What’s your secret?

In his book Zero To One, Peter Thiel asks the question “What one thing do you know that no one else in the world knows?  What’s your secret?”

The answer to that question is the secret to starting a successful company.

downloadWhat Thiel is suggesting is there are things in this world you observe, intuitively know and understand more than anyone else.  By peeling apart those layers and understanding where there could be value creation you will find the golden nugget.  Then it’s as simple as creating a new company, building the product and releasing it to the world.

What he is also illustrating here is that success comes from ingenuity and uniqueness, not copying others.  The world doesn’t need another anonymous messaging app or social network.

It needs your secret.

Do you realize there are things only you know about the world?  Most likely there things you continually notice about your everyday life, the city you live in or the technology you use that keep bugging you.  There are problems you continually encounter where you might be wishing someone fixes them.  Do you maybe see a better way to do them?  Do you keep getting frustrated at the same places and times each day?  There might be something you can do about it…

Once we come to grips with the magnitude of this reality starting a company becomes a lot different.  You now realize each and every one of us have the ability to create successful companies.  All it takes is a little focus and observation of the world around you, and then having the fortitude to create a scalable solution.

Today, think about what might not ever be created if you don’t build it?

Finally Emerging From A Founder Depression

At times we can be our own worst enemy.  The challenge is to minimize those times.

We often hear choosing to become an entrepreneur – and the life that accompanies it – is not for the faint of heart.  This is absolutely true.  But for the longest time I didn’t really understand what it meant.  Or moreover, I didn’t fully respect the ramifications of the simple choice of taking my entrepreneurial leap.

Yet now being on the other side of this experience, I understand on a deeper level what entrepreneurship all about, and how to best navigate through it the rest of my life.  As I describe some of my thoughts and observations, I hope they might resonate with you as well and help you through whatever your situation you might be in currently.

Entrepreneurs, by default, are high performers.  And high performers, by default, are hard on themselves when times get tough.  Combine those two and you could get a deadly combination.

Entrepreneurs hold themselves to higher standards than others and often are disappointed when things don’t necessarily end up as great as they had thought when they initially set out.  But you know what?   Entrepreneurship never ends up like you initially thought.  It’s messier than anyone ever imagines and more extreme than anyone ever describes.

After I experienced a failed startup I dropped into what I now can identify as a depression.  I was not – and am not – depressed as in the clinical sense, but it was more like what you would think when people refer to the last economic depression we recently survived.  It was temporary and externally triggered.  Things weren’t right and I was responding to them certainly in a negative and self deprecating way.

It was painful.  It felt troubling.  It sucked because I wasn’t supposed to be there.  Or so I thought.

What I discovered was I denied myself some truths I should have admitted at the time.  I wasn’t admitting things like: 1) I really didn’t know what I was doing, and neither does anyone else.  2) The business was not working the way we had positioned it.  2) Startups actually do fail!  3) It’s okay to walk away rather than being so committed to a project you drive yourself into the ground.  4) Your personal value is more than just your company’s success.

I did not admit those things and the result was just that – nose dive right into the ground.  Being a friend or family member you probably wouldn’t have known it by being around me.  I am a damn good actor.  I do a great job of burying the issue and grabbing another beer to selflessly talk about your challenges and issues.

Yet deep down inside was some of the worst self talk anyone could imagine.  I was not my biggest cheerleader, supporter, believer and best friend.  If you are wondering, negative self talk is not the path to success.

It took a few years to pull myself out of it.  It took me accepting the fact that although I knew I could be a great founder at some point in my life, now was not the time.  It took me putting my ego aside and accepting positions with other startups and companies where I could add value and learn more about building companies.

It seems elementary now, but letting go of the founder dream and using my skills in an another company was the farthest thing from my mind at the time.  It took me admitting I did not know it all and I need to place myself somewhere to both earn a living and learn more about the world of technology and growing a business around it.

This type of wisdom and perspective is almost impossible when you think you are worthless.  And that is exactly what people think when their startup fails.  They think since they could not make their own company work – one where they pretty much put every ounce of effort they possibly could into making it work – what’s their value anywhere else?  This and other similar thinking is obviously incorrect and ill applied.  Yet, I am telling you this is exactly what I and other founders find themselves thinking.

I have since pulled myself back together, landed a great position with another company here in Seattle and on the path to learning and earning!

The resulting mental and emotional clarity is refreshing. It has allowed me to stabilize my life and opened up space for other projects like Founders RAW, Coinme, and getting back to writing.  It has allowed me to establish myself as a mentor and advisor to other entrepreneurs, here and elsewhere in the world. It has allowed me to embrace and fully enjoy a meaningful relationship for the first time in a long time.

The lesson here is not that you can do things to avoid the founder depression.  More than likely it’s inevitable for you, me and every other entrepreneur.  The lesson is in identifying the oncoming founder depression, quickly observing its symptoms, and then finding mitigation strategies you can deploy to keep you afloat – and happy.

Entrepreneurship is not for the faint of heart.  But it is for the wise and honest.