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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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.

The Value of Youth Sports In Startup Founder Success

A few recent conversations have turned towards youth sports participation and the valuable life lessons they provide.  One in particular stood out to me – youth sports participation is one of the best training grounds for a startup founder.

How would I know?  I was a competitive athlete pretty much since the time I could run, competed up until college and still remain athletic and competitive today.

soccer1Although I didn’t necessarily know it at the time, as I was playing youth soccer, basketball and baseball I was adequately preparing myself for a life long battle in the business world.  Learning to cope with immense challenge and competition is paramount to a person’s ability to achieve success.

I am so grateful for the experience and for my parents not forcing me into any specific activity, but rather allowing me to participate in a number of sports so that I could further develop my athletic ability, maximize my leadership skills and mature enough to determine which sport I more fully wanted to pursue.

It turned out it was Soccer, and it’s crazy to think back and imagine me as an 8 year old running around in a grassy field on an early Saturday morning thinking I’m just having fun when in actuality I was taking in and absorbing lessons which would help me in my life 20, 30 and 40 years down the line.

Below are just a few ways youth sports help develop a young energetic child into a strong willed startup founder.  I thank John Cook of GeekWire for the conversation that sparked these thoughts.

Teamwork

One of the first things you learn as a young athlete is how to play as a team and how to become the best teammate possible.  No soccer team can win with one person trying to play alone – teams must be able to depend on their offensive players, their defensive players and ultimately their goalie to perform to their best ability.  Players must be willing to step up and take the shot, yet at the same time be able to support and assist their other teammates if the organization is going to function properly.  This requires youth to understand which is which, and the appropriate timing of each decision.

Companies are the same way, they aren’t built by one person. Startup teams must be well rounded, supportive and willing to do whatever it takes to achieve success – for all members of the team.  That, or the team won’t exist.

Leadership

Even at the earliest of ages sports teams will vote on a player to become captain, basically naming the leader of the team.  I believe this is the single best thing we (should continue to) do for our youth.  Captains are usually the more talented of players, have wide ranging experience and are outgoing and not shy in their ways with others.  But most importantly they are willing to take on responsibility.  They must lead the team, delegate when appropriate and stand up for a teammate if something goes wrong.

I believe giving responsibility as early as possible is one of the best ways to develop great leaders.

Imagine the lessons a 10 year old is learning as they lead their team during youth competition.  He/she is learning the basic tenants of team leadership, things they can apply to almost any endeavor.  In short, they are the on-field CEO and the success or failure of the team will rest (at least somewhat) on their young shoulders.

I cover startup leadership quite a bit so if you are a regular reader you will know my basic thoughts on the subject.  Simply put, startup CEO’s need to take full responsibility for their organization from day one.  They must wear the captain’s band on their sleeve in plain view so everyone knows where the buck stops.  This is not for their ego; it’s for efficient and effective organizational structure.  Why should an employee ask 3 people a question when really they should go directly to the decision maker to get the best and quickest response?  If employees in a startup don’t know who the decision maker actually is, whatever startup they are a part of ain’t gonna be around very long.

Failing

I get it, losing is not why we play the game.   Go visit a sports park on a weekend and watch how kids react to losing nowadays.  Yet losing in sports – just as in life – happens.  It actually happens a lot.  Learning to fail gracefully is a huge lesson any person, especially for someone thinking about starting their own company.

Why am I telling you failing is good for children?  Failing, maybe even getting injured  in the process, and then getting back up and trying again shows young athletes that if you do not quit then each new day is a new opportunity to win.  Losing teaches children not everything in life is guaranteed.  In fact, it teaches us more often than not things will not go as originally planned.  Sometimes shit hits the fan and you need to retreat and regroup to determine your next move.  There’s your basic “strategic thinking” lesson in action, a skill founders must employ A LOT.  Losing teaches youth hard work is required to experience success against your competitors.

This is essentially the experience of any early stage founder.  Startups fail most of the time.  Using lessons from our youth we can realize we just need to get back up and try it again, and hopefully we learn something in the process.

Enduring Hard Work

Finally, part of learning from failing is gaining the endurance to last long enough so we can experience success.  I distinctly remember our training sessions during soccer season.  They sucked.  Even if we weren’t going to be the best in the state of Washington (which we were 3 out of 4 years) we were definitely going to be the most in shape.  Coach made it very clear we would be the team with the best endurance around.

So we ran.  A lot.  We ran until we dropped, and then we ran some more.  We learned to embrace hard work and earn our success.  We learned anything worth winning was worth enduring tough challenges and the hardest of practices.  It was our standard and we embraced it wholeheartedly.  We spoke it.  We lived it.  We practiced it and we played it.  No wonder we won the state championship 3 out of 4 years I was on the team.  It was in our our DNA and our blood.

Startup founders need to take ownership of their future.  They simply need to determine where they are going, commit to a standard and uphold it no matter the cost.  They need to bleed confidence to the point where their success is inevitable.  They need to work harder than their competition.  This doesn’t mean work the most hours as humanly possible, that would be as dumb as our soccer coach running us until we all pulled hamstrings, eliminating us from competition completely.  Startups must figure out how to work harder but also work smarter.   Determining and following quality performance standards will do wonders to founders and their startup teams.

Youth sports are fun but they are also incredibly valuable to our society.  If you are a parent I would encourage you to place your children in a positive environment where they can develop leadership and success skills as early as possible.

Just like you.

$99,970,000,000 is The Difference Between These 3 Decisions

If MySpace would have just copied Facebook, it would have been FacebookSean Parker

That was Sean Parker’s answer to the question “what happened to MySpace?”  in a recent interview with Jimmy Fallon.  This got me thinking and was the needle prick I needed to start on a topic I have wanted to write about for some time.

If you can remember at one time MySpace was the social networking behemoth, holding the crown as the largest site on the web.  “Do you have a MySpace?” was the proverbial question between twenty-somethings.   They had over a hundred  million users worldwide, were driving revenue in the hundreds of millions of dollars and it looked as though we had an MTV 2.0 on our hands.  They made headlines with the acceptance of a $580 million acquisition from News Corp, validating Social Networking as a ligament startup business venture.   Little did we know they would turn out to be a joke, an afterthought on the web and a huge lesson to any young founder looking to build the next big company.

At right is a snapshot of the MySpace.com monthly unique users from earlier this year (courtesy of Techcrunch). As you can see (and probably already knew) usage has continued to plummet.  MySpace is literally a ghost town at the same time Facebook has grown to the largest site in the world, officially eclipsing 700 million users on their way to an inevitable 1 billion users and will soon IPO with a valuation of more than $100 billion!  This begs the question: What happened?

My take from Parker’s statement is MySpace had such a massive lead in users, media coverage as well as total mindshare in the social networking space it was their race to loose.  Quickly incorporating the features they saw Facebook releasing could have helped them stay atop the game.  Imagine what MySpace would be worth now if all they did was manage to keep it all together and ride out this new wave of social/mobile web.  Definitely more than the rumored $30 million News Corp is looking for to get them off their books.  What a sad ending to once dominant company.  To take Parker’s statement a bit further, I argue the biggest mistake MySpace made was sell out to the suits for a mere $580 million.  Here are three key differences that add up to a $99,970,000,000 difference between Facebook and MySpace.

Lack of vision and Leadership

The biggest difference between Facebook and MySpace is an intangible I have written about it extensively before.  Just as the difference between Apple and Microsoft was found in Leadership, so too was the difference between the social networking companies Facebook and MySpace.   (Get used to me writing about vision and leadership because I believe it is the number one reason companies succeed or fail.)  MySpace was early out of the gate and sprinted the first mile but did not foresee what could possible be on the horizon.  All they knew was people wanted a page to customize as their own and maybe a place find and connect with others.  But who was leading MySpace?  To put it bluntly, MySpace had no clue what they were doing and no clue who to look towards for leadership.  MySpace was not created by a visionary such as Mark Zuckerberg, who saw something in the web most did not.  They were driving solely on dollars and revenue, and the lack of vision and focus devastated MySpace’s growth in the end.

If Facebook was only a profile page where you can connect to your friends, MySpace would have won the race.  Facebook bet (and won) on a vision of the personalized web, integrating our friends in almost everything we do in the digital world.  Zuckerberg saw not only a web of information, but a web of people and set out to connect all those people into the web.  Execution on this vision required laser focus from a passionate founder.  MySpace ran the first mile faster but lost its way.  Facebook knew the course and won the marathon.

Message to entrepreneurs:  Have the intelligence to place a visionary leader at the heart of your company and let them guide the way.

Technically Inept

Myspace proved they were technically inept, lacking any engineering vision of how the web should work.  According to a recent Bloomberg Businessweek tell-all article, the company was constantly at odds with leadership on how/what/where to innovate.  “They were having to do all technical innovations to address the various panics that are happening. Basically their development cycle turned into one of crisis management, not one of innovation.”  Bottom line, MySpace lacked the vision as well as the technical edge necessary for a web company to maintain their dominant position.

More importantly, MySpace was not created as an innovative new platform built by forward thinking engineers. They were a company who decided to copy Friendster using sub-par technology but grew because they understood how to market their brand to the general public.  Choice quote from the article: “Using .NET is like Fred Flintstone building a database,” says David Siminoff, whose company owns the dating website JDate, which struggled with a similar platform issue. “The flexibility is minimal. It is hated by the developer community.”  Why did they choose to do this?  Driven by revenue pressures they chose to skimp on technical details and focus on more ads.

On the contrary, Facebook was intended from the beginning to be a socially transformational technology built by smart engineers.  Zuck made it a point that their engineers would determine the road ahead.  They aimed to redefine the web and understood this would require major investment.   As a non-technical executive, it was still obvious to me who was stronger in  engineering talent between the two companies.  Remember how refreshingly clean a Facebook profile felt vs the craziness that was a MySpace profile.  MySpace chose to skimp on the engine and polish the chrome.  Bad mistake.

In an interesting note, most close to Zuckerberg would admit the best decision he has ever made was to bring in a much senior and more businesslike Sheryl Sandberg as the Chief Operating Officer of Facebook.  It is said she is in more direct managerial oversight than Zuck, and who would want that?  Sandberg has been credited with building out Google’s ad business, helping create a multi-billion dollar search ad business.  I credit Mark for submitting his ego and filling holes with the right people, Facebook is better off for it.  Looking at MySpace and their recent history I cannot say the same.  Holes were not filled and egos were not subdued.

Message to entrepreneurs:  Know where you are good, understand where you need to be great, and find the right people to fill the gaps.

Poor Culture Fit with News Corp

“I think any time a startup is acquired, there’s always a certain amount of culture clash.” – Chris Dewolfe, MySpace Co-founder and one time CEO.

The worst decision for the future of MySpace was to sell the company to News Corp.  (Okay, the founders and initial investors made out fine, but the future of the company pretty much was set in stone.)  Time and time again I observe or read about another startup being acquired by a larger company and I think to myself  “well, there it goes…

The blazing, crazy, edgy, partying, sometimes innovative culture of MySpace was suffocated by the bureaucracy of corporate New Corp.  Do yourself a favor and think about your startup culture currently, and then think about the culture in a Microsoft, Google, Aol, or any other large corporation.  Ask Dennis Crowley.  Ask Evan Williams.  Ask Caterina Fake.   It usually doesn’t end well when you sell your booming startup to a large corporation.  Facebook fought off takeover bid after take over bid until everyone knew they just weren’t ever going to be for sale.  That’s ballsy, but its also what has to happen if you want to see your vision come together.

Message for entrepreneurs:  If you have a long term vision for your company, don’t sell – ever!  If you want to make some quick money, sell at the top of your hype – and walk away as early as you can.  The post-acquisition company will be nothing like the pre-acquisition company.

I am tired of seeing innovative startups being gobbled up by larger corporations only to disappear off the face of the earth – this is not how innovation changes the world.  It is actually how innovation is hindered.  I understand, as a founder you are double minded building your company.  You want to make a chunk of cheddar, and  there’s nothing wrong with that.  Isn’t that what going into business is all about?  I understand… and I would want to do the same thing in your position.

But before you sign those papers I would step back and determine what you really want and if it’s the best option.  If you really need to sell, truth is you did not build the company correctly.  If you want to cash in, great.  But understand, odds are the world will no longer be changed by your innovation.  If you really feel selling is the best option, think deep and hard about the culture inside your company as well as inside the potential acquirer because the marriage is going to be tough.  And if you feel deep down in your heart your company has a great future, don’t sell out.  Just think about how News Corp and the original MySpace founders feel about this outcome right now.

Image courtesy of Flickr user UltraRob.

This post was originally published on BusinessInsider.com.

Steve Ballmer’s Lack of Real Leadership

 This post was originally published on BusinessInsider.com.

Around 1975, Microsoft Corporation and Apple Inc. were created, kicking off what would become one of the most fascinating times in modern history.   During this period both have been significant players in the PC revolution, although recently as businesses they appear heading in opposite directions.

One is accelerating to new heights and one is stalling out like it forgot to refuel at the last gas station.  I think something abnormal is going on here and believe it’s more than the general “great products” vs “not so great products” argument.   Below is a view of the stock price of each company dating back to 1986.  Here is Microsoft:

(images courtesy of Yahoo Finance).

And below is a view of Apple, again viewed with a long lens dating back to 1986.  On thing to note is the scale on the right.

The last decade has seen Apple explode in value, culminating in them becoming the largest technology company in the world.  During the same time frame, Microsoft was dethroned by Apple and has pretty much remained stagnant.  Indeed, there is something peculiar going on here and anyone looking to build a consumer brand should listen closely.  The difference between Apple’s success and Microsoft’s lackluster performance can be summed up in one word – Leadership.  It takes more than smart employees, good technology and market dominance to deliver great financial results.   It also takes a Great Leader.

JobsSteve Jobs understands Leadership, Vision, Inspiration and Branding are vital to business success.  He gets it.  He understands how to position his Brand in the soul of a human being, amazingly interweaving his devices into peoples identity.  This is accomplished by casting a vision and allowing a tribe of followers to form around it.  He also understands: it is first about the vision and only then the resulting products can come in to reinforce the vision with the consumer.  Users of Apple products gladly follow when they realize the vision and resulting products make them feel better.

Jobs’ vision is one where the terms “Think Different”, “Beautiful Creation” and “It just Works” are used in description.  And although difficult to put into words as a consumer, you just feel it – viscerally.  It’s almost magical.   Jobs inspires with every word – not in a flakey, shallow and inauthentic manner – but a genuine manner.  I understand no one is perfect, but he definitely gets how to move people.

Steve Ballmer is flat out not an inspirational leader nor a visionary.

BallmerWith more than ten years at the helm of one of the largest companies in the world, Steve Ballmer has obviously done many things right.  One thing he cannot do is accurately describe the deeper purpose of Microsoft or any of their products.  When he tries, it doesn’t get anywhere close to touching the human soul.  He lacks the innate leadership quality of Inspiration.  He can run and jump, scream and yell, and do Monkey dances on stage all day long but this is not leadership.  Nor is it inspiration.  (Can you even imagine Steve Jobs doing this?)

Unfortunately for Ballmer, Microsoft is stuck between so many business markets it’s almost impossible to tie them together coherently to form a strong brand identity.  Without a unique purpose and vision, there is no brand identity.  The latest Microsoft slogan urges me to “Be What’s Next.”  I am not sure what that means… consumers need to be able to viscerally understand the brand and why they should be using it.  Like it or not, this responsibility rests on the leaders shoulders.  Ballmer has failed to communicate these fundamental aspects of Microsoft on a level that connects with everyday consumers.  He just doesn’t get it.

Is it any coincidence the maxim of Microsoft’s value as a company (January 2000) is pretty much the exact date Ballmer stepped into the CEO role?  And incidentally enough, the first real growth in Apple’s market cap appears not long after Steve Jobs arrives for his second coming as CEO in 1996.  The Leadership difference between these two men has made all the difference in respect to their company’s results.

Looking back at Microsoft’s stock price you can notice a time of incredible growth, back in the 90’s.  Who was the leader at this time in their history?  Iconic founder Bill Gates, an inspiring visionary in his own right was in charge at that time.  He inspired the world with the vision of “a computer on every desktop” during the emergence of the PC and Enterprise Revolutions (and thus the software running on them became a hot market).  Indeed Gates vision expanded the perspectives of all employees and rallied them to become the largest technology company in the world for many years.  But things have changed and today consumer devices are the rage.  What’s the overarching, game changing, ever growing Microsoft vision now?  I don’t see this type of world changing leadership and inspiration radiating out of Redmond any more (and I live 15 miles away).  Suffice it to say Apple saw this New World Order coming and Microsoft didn’t.

People follow leaders who embody a sense of purpose that inspires those around them.  Notice how consumers wait in lines for hours just to have a chance to own an “i-whatever”, the newest product that will touch their soul.  People give standing ovations and watch streaming online video during Steve Jobs inspiring  keynotes speeches.  All these happen for Apple because of Steve Jobs and his Leadership.  They create a mystic aurora which parlays towards the next round of  product announcements.

All this became very apparent to me recently as I observed the response to both companies announcements – Apple’s at their WWDC conference and Microsoft’s at the E3 conference.  The world huddled around their screens in anticipation of an announcement regarding Apple’s next mobile operating system, the iOS5.  In fact, there were no less than 37 individual posts covering Apple on SAI alone, Monday June 6th, the day of the announcement and.  Also 17 posts covering anything that is Apple appeared on Techcrunch.  Alternately, Microsoft’s announcements were an afterthought, an oh-by-the-way-this-happened byline with 3 posts that same day.  Succinctly put, no one really cared.

This unfortunate reality for Microsoft is directly tied back to Ballmer’s lack of Leadership, Vision and Inspiration.  People would have cared about Microsoft’s announcements had the products touched their souls with a deeper purpose.  Right now, go to Apple.com and Microsoft.com and see what I am talking about.  I am like most, finding it impossible to put a finger on exactly what it is that makes Apple… Apple.  All I can say is Steve Jobs knows something Steve Ballmer doesn’t.

Don’t get me wrong, we are talking about a great company in Microsoft, one that still does more than $60 billion in yearly revenue and employs some of the smartest and most talented people in the world.  They hold dominant positions in numerous markets.  But it pains me to write these words and acknowledge the reality of Microsoft’s future.  I am a Seattle resident and appreciate the value Microsoft has added not only to the world but specifically to Seattle.  We owe much of our regional economy to Microsoft.  They have done great things and the enterprise software ecosystem they created is quite amazing.

Yet, I see a company waning at a time when they really need to figure out their guiding purpose.  When I look at Apple, I feel secure they know where they are going.  When I glance across Lake Washington to figure out what Microsoft is doing, I am at a loss for words.  And this is scary for me.  I can only imagine what it’s like for the employees and the executives.

Lessons for us younger founders and entrepreneurs:

  • Find a deeper purpose to associate with your products and business
  • Cast your vision with simple, strong and relatable words
  • Become (or find) a leader who can connect with people and continually inspire them toward action

I don’t know who it will be but Microsoft is in desperate need of a Leader, an inspirational visionary who can turn this boat around – NOW.

Disclaimer: I have no personal connection with either Steve Jobs or Steve Ballmer and this is in no way personal towards either one of them.   My opinions are purely anecdotal and from observations as both an entrepreneur and consumer.

On Failure

“On the road to invention, failures are just problems that have yet to be solved.”

My reading this morning brought me to this little gem:

Fearing failure stifles creativity and progress. If you’re not failing, you’re not going to innovate. Do your product or service a favor: embrace failure and blueprint a plan that affords you the opportunity to do it early and often. 

I can’t tell you how strongly I agree with this statement.  Whether it is product design and prototyping or more generally concerning your entrepreneurship path, the worlds biggest failures end up becoming the worlds most successful people and products.  I will write a more in-depth post on this soon.