Don’t Emulate Steve Jobs, His Lesson Is All About ‘Finding’ Yourself

Michael Arrington interviewed Salesforce founder and CEO Marc Benioff recently at TechCrunch Disrupt.  It’s a great conversation, including a few touching stories about Marc’s relationship with Steve Jobs.  You should watch the entire conversation if you have a chance, there’s some truly wise observations from Benioff.

But what emerges is one of the best things I have ever heard regarding Steve Jobs.  Marc describes how we shouldn’t look at Jobs as an example of leading by being an asshole, visionary or anything like that, but in understanding Steve Jobs showed us the way through self actualization.

Actualize Yourself.  Look at the world from the inside out.”  Benioff says Jobs was successful because he was not afraid to take the journey towards self actualization.  “We all need to all be working on actualizing ourselves.”

This Keynote Will Go Down As The Turning Point In Mobile Communications History

I just (re)discovered this Steve Jobs keynote as I was doing some preparations for an upcoming Seconds demo.

It’s amazing.

Not only is it a perfect example of how to pull off a flawless demo, but it also occurred to me that this unveiling of the iPhone was a once in a generation event.   It’s hard to overstate the impact the iPhone has had on our world.  The introduction of the iPhone completely changed the mobile landscape, bringing smartphones into the mainstream at the same time setting the bar for Andriod devices and other smartphones.

It also pretty much paved the way for the iPad, which arguably is the fastest adopted new device/technology in history.

Sit back, take notes and enjoy history.

One Leader Steps Down, This Leader Steps Up

Today I learned the hard news Steve Jobs was stepping down as CEO of Apple, the worlds most valuable company and the envy of any honest person in the business of technology.  Like most people, I looked at Jobs as more a Saint, Monk, or Prophet; less of a businessperson.  Is this fair or even right?  Who knows… but he is truly one of a kind and I really don’t know what to say at this point.  What I do know is he set a damn high bar for me and all other leaders.  Thanks Steve.

So much is being written regarding the amazing performance of Steve Jobs I think I will leave it to them to tell you his story.

Instead, I will tell you mine.

You have no idea how many sleepless nights (in Seattle no less) have been spent tossing and turning, just wishing a great engineering team was standing behind my vision.  I have known for some time now a grand and transformational “something” is stuck deep down in my soul and needs others to help pull it out.  For so long I felt I just needed the right pieces to fall into the right place.  For so long it felt like a hope, a dream or a far off story only found true reading through Inc. magazine or TechCrunch or Silicon Alley Insider.

Well that dream has finally come true.

I have chosen to accept an offer to become CEO and co-founder of a promising startup here in Seattle, one just about to hit the public radar.  It really is like a dream come true and the vision we are setting forth is nothing short of transformational.  Keep an eye on this one.

A little Background – Loyaltize

Years ago something hit me like a ton of bricks and I had a vision:  The local economy was one of the one the last holy grail industries of the internet, not fully transformed by the consumer web as we know it today and ripe for change.  I also realized businesses function by and large through customer loyalty.  Most people intuitively understand 80% (or a majority) of a businesses revenue comes from 20% (or a minority) of their customer base.  This is natural and it will never change, you can ask Vilfredo Pareto on that one.

I also noticed local consumers have distinct relationships with specific businesses, and come-hell-or-high-water they will do business with them.  People have favorite restaurants, coffee shops, wine stores, clothing retailers, gyms, etc…  Why not reorganize the local economy around the consumer and their ability to dictate relationships and interactions with their favorite entities.  Allow them to choose who/what to follow and who/what to stay connected to and receive information from.  Ya know, around the loyal customers and their view of the local economy.   Why not Loyaltize?

Understanding that fact, it baffles me why the hell new “advertising” and “group coupons” and other crazy schemes keep popping up every day claiming to increase revenues, profits, customer bases and all other things push media in an effort to bring MORE customers in the door.  It ain’t about “offers” people.  To me, that is just ass backwards to how it actually works.

Businesses don’t want more flaky one-night stands, they want more long term relationships.

When I looked at the current technologies, business practices and the state of the local economy I saw inefficiency, ineffectiveness and little change from 20 or even 30 years ago.   I am sure I was not the only person who saw an opening, but I am positive no one has my exact vision.

Except This Guy

I was recently approached by a talented local engineer here in Seattle who wondered if I would be willing to talk about my ideas on Loyaltize.  He thought we had the same vision.  What he didn’t know was I had as so much given up on my dream of Loyaltize as the summer had progressed.  You see, I did have a startup at one time – a bootstrapped company we threw together called Loyaltize – but after failed attempt on version 1 we backed off and the team dispersed early this year.  Trying to build a startup while being employed full time is not the path for success (at least not for me).   Trust me, after almost 5 years of blood, sweat and tears, it’s a little tempting to throw in the towel and walk on home.

As some of you may know, in May I said “F-it“, kicked my full time job to the curb and doubled down on myself as an entrepreneur.  I figured one thing out – if I don’t fully believe in myself and do whatever it takes to succeed – why would anyone else believe in me?  Why would they believe enough to join or invest?  I also figured I would rather die knowing I tried everything possible to make my vision come true rather than feel regret as the years went by.

Side note: I also started writing on here, Business Insider and other publications, proving to be the smartest decision of my life.  No joke.

Throughout this summer I entertained different business ideas, different roles, different industries and even different approaches to business.  Nothing felt right.

Well, as we spoke that day something woke up in me and it felt as if an old friend had just come back into my life.  I am sure it was obvious to him as well.   The blood started rushing to my head and the vision started to come back to life.  I said to myself “I am home and it is time“.

Since timing is everything I will refrain from naming the company or any others involved.  But keep your eyes open, you will soon start seeing and hearing about it.  Our vision is eerily similar to what you read above and mark my words: your local consumer experience will drastically change in the next five years. 

Today I enter the next phase of my life.  As CEO of a new company, with a new life and a world of potential in front of it. I am set to make the best of it, whatever that means… be it lessons learned, acquisition, IPO or lifelong employment/retirement.

As I step up to be the leader of this company – and a leader in the technology industry as a whole – I cannot let go of the irony this day holds with the greatest leader the business world has ever witnessed stepping down.  But I must since life always has it’s way of moving forward.

It seems fitting that Steve Jobs said it so eloquently: “We believe that people with passion can change the world… for the better.  And it’s those people who are crazy enough to believe they can change the world, actually do.”  

Will do, Steve.


Steve Ballmer’s Lack of Real Leadership

 This post was originally published on

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 and 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.

Graduates: Stay Hungry, Stay Foolish

Here’s to all the graduates out there who are now taking the leap into the real world.  I cannot say it better than Steve Jobs in his 2005 commencement speech to Standford University students.  This is one of the most incredible speeches I have ever heard and for you, a 15 minutes well spent.  Enjoy.

Be Iconclastic

Ever look at prominent figures in the world and wonder how they stand out from all the rest?  I believe it comes down to how they think.   I believe you can think like them too.  Or.  Not.  Like.  Them..?    At this point, you may not know what the word Iconclast means, but by the end of this post I hope you will be inclined to think a bit differently.

Gregory Burns talks about people who do things others say can’t be done in his book Iconclast – A Neuroscientist Reveals How to Think Differently .  He calls them Iconclasts.

He succinctly describes being an iconclast hinges on 3 things: perception, courage and social skills.

The successful iconclast learns to see things clearly for what they are and are not influenced by other peoples options.  He keeps his amydala in check and does not let fear rule his decisions.  And he expertly navigates the complicated waters of social networking so that other people eventually come to see things the way he does.

If you are like me you’ll want a shorter and easier way to remember the word:

Thinking different is so easy, yet it baffles me how many people do the exact opposite.  They think the same as everyone else.  For some reason they don’t want to be different.  They don’t want to separate themselves from the crowd for they just might have to form an opinion.   They think the same as their neighbor, their classmates, the same as their teammates and they even the same as their competitors.  To me this is just crazy and a recipe for averagism.

Seriously, when did it become generally accepted to think the same as your competitor?  I am pretty sure this type of thinking did not go on in the days of early civilization.  If someone did I guarantee they we’re quickly eliminated…  Thinking the same as the competition is what gets us all these copy-cat products that flood the market.  How many different Groupon competitors do we need?  How many different brands of ‘Bran Flakes’ Cereal is enough.  I could go on and on, but I won’t because I’m not here to inspire you to copy others.  My goal is to inspire you to think differently.  And since we all are capable of thinking… being an Iconclast is now up to you and your thoughts.


Berns describes in detail how our brains actually perceive thoughts.  Being too scientific for this post, I will only encourage you to buy and read the book for yourself.  But to paraphrase: because we learn from past experiences and past experiences shapes both our perception and our imagination, we tend to constrain our views on things as we grow older.  This is not good for much of anything, but most importantly you will begin lose your creativity.  As time goes on you start to see the same things as everyone else.  And if you see everything others are seeing, you are not to unique.  How are you supposed to be innovative when you see just the same as the others?  Berns suggests we continue to bombard to brain with new experiences.

I suggest running the exact opposite direction as everyone else.  I have always been attracted to uniqueness.  It doesn’t have to be anything eccentric, just being different.   Everyone staying in their safe job because of the recession…  quit yours and pursue your dream of building a company.  You will have a leg up since most others are going in the opposite direction.  Seeing a lot of other companies are offering “daily deals for X” and “social networking for Y”?  Why not have an original vision and do something different?   Most importantly, get out of the daily routine you have slipped into over the last 8 years.  Take Berns advice and change your life.  Create new experiences.  Iconclasts do this and succeed.


Plain and simple, humans hate fear and live everyday to avoid the feeling.  Fear prevents people from taking action, and even worse it changes the way they see the world.  The ultimate underpinnings of fear is failure, which is the strongest force inconclasts overcome.  Berns notes fear permeates any business and should only be taken as a warning sign.  Once the fear is recognized, it can be deconstructed and reappraised.  So there you go – everyone experiences fear.  Inconclasts dissect it and figure out what it is actually pointing to.  Then they act accordingly.

Here’s my take:  Most people in the world are scared, weak overgrown children.  Sorry to be so blunt, but this is what I have picked up over the years.  Just as we tried to fit in with the “cool” kids on the playground during recess, we go about our lives in constant fear of what people think.  Most people never live as an independent thinker because they are so worried of what other people will think about them.

I say “who gives a @#$% “and “Screw what they think“.  Why do you care what some random guy thinks about you or your idea?  Here’s the truth: One minute after you leave the conversation he will forget what his opinion of your idea was.  He has enough to care about in his life, why would he waste time thinking about you?

Here is Amazon’s Jeff Bezos, an Iconclast I have always looked up to referring to his willingness to be misunderstood.  He has no fear of failure:

If you invent frequently and are willing to fail, then you never get to that point where you really need to bet the whole company. AWS also started about six or seven years ago. We are planting more seeds right now, and it is too early to talk about them, but we are going to continue to plant seeds. And I can guarantee you that everything we do will not work. And, I am never concerned about that…. We are stubbon on vision. We are flexible on details…. We don’t give up on things easily. Our third party seller business is an example of that. It took us three tries to get the third party seller business to work. We didn’t give up.

My mind never lets me get in a place where I think we can’t afford to take these bets, because the bad case never seems that bad to me. And, I think to have that point of view, requires a corporate culture that does a few things. I don’t think every company can do that, can take that point of view. A big piece of the story we tell ourselves about who we are, is that we are willing to invent. We are willing to think long-term. We start with the customer and work backwards. And, very importantly, we are willing to be misunderstood for long periods of time.

I believe if you don’t have that set of things in your corporate culture, then you can’t do large-scale invention. You can do incremental invention, which is critically important for any company. But it is very difficult — if you are not willing to be misunderstood. People will misunderstand you.

Any time you do something big, that’s disruptive — Kindle, AWS — there will be critics. And there will be at least two kinds of critics. There will be well-meaning critics who genuinely misunderstand what you are doing or genuinely have a different opinion. And there will be the self-interested critics that have a vested interest in not liking what you are doing and they will have reason to misunderstand. And you have to be willing to ignore both types of critics. You listen to them, because you want to see, always testing, is it possible they are right?

But if you hold back and you say, ‘No, we believe in this vision,’ then you just stay heads down, stay focused and you build out your vision.

Social Networking

To be successful, it comes down to one’s ability to connect with other people.  Two aspects of social intelligence figure prominently in success or failure: familiarity and reputation.  Incidentally the two are interconnected, since in order to sell your ideas you must create a positive reputation that will draw people toward what is initially unfamiliar and potentially scary.  Familiarity helps build your reputation.  Simply put: to get their ideas into the mass market iconclasts must be able to connect with people.

Think about someone right now who you admire and feel they are a “success” in your eyes.  And now ask yourself this: “Are they good with people?  Do they know how to navigate the social waters?”  I guarantee they (or someone they are close to) understands this principal.  Being an iconclast, thinking different, changing your perception, and dealing with your fear will only get you so far.  I would argue being great in the people department completes the package and helps you rise to prominence.

If you have been reading the words Think Different and imagining a certain company, I am sure you are not alone.  It’s not a coincidence the largest Technology company and one of the most recognizable brands in the world adopted that phrase in most of their marketing.  Apple thinks differently.  I believe the Different Thinking of their founder Steve Jobs is the sole reason they are where they are today. I will leave you with a video that sends chills down my spine.  It is one of the early Apple commercials and the first one in which they used the term Think Different.  Enjoy.