Chapter & Lesson #14

“Better to remain silent and be thought a fool than to speak and to remove all doubt.” 


One of my favorite stories from this era is from a meeting I had with Steve Ballmer, the then CEO of Microsoft, while I was enrolled in Microsoft’s special Executive training program they called “The Bench”.  The Bench program was put together in 2000 shortly after Ballmer took the reigns of the CEO spot after Bill Gates decided to step away from the CEO job and become the Chairman.  Microsoft was becoming increasingly concerned that their young managers were not up to the task of leading the company to whenever it was they wanted to go, and decided some good schooling for young talent might be the right answer.  Most people did not take the training very seriously, but I found a lot of the content in the courses at least somewhat valuable, and the access to the other people in the company and the networking provided by the program was definitely worth the price of admission – which was free if you were nominated to it!

It was spring of 2001, via the program, I had received an invite to go and meet with Ballmer, the topic for the meeting was undisclosed, and the entire setup of the meeting was very odd as we were told that no preparation was necessary- this was highly unusual when meeting with the CEO at Microsoft, as it turned out that was all by design.  The meeting was setup in Steve’s personal conference room in Building 34.   Ballmer had a special wing in building 34 dedicated to him and his support staff.   To get in there you had to pass through a special security area where there was a guard at the door of the wing and you had better be coming with an invite or you would be swept out of there quickly.  Apparently, all the windows in the CEO wing are bulletproof as well (and no I am not making this up).  As you walk through the wing there are all kinds of handlers and special staff in there who are dedicated personally to seeing out every detail of Ballmer’s every move.   It is a bit intimating to even step foot into the place.    

After receiving the odd invitation to meet with Mr. Ballmer, I asked twice if there was any prep required for the meeting and was told it was not necessary.  This had me concerned as most meetings with Steve Ballmer or even any of his VP’s would require pre-meetings, and sometimes weeks of planning to get the exact powerpoint deck, messaging and every other detail ironed out before getting in the room with one of these guys.  So this was for sure going to be a somewhat different and odd meeting with the CEO.

When I arrived at the conference room there were about 6 other people who also were assembling at the same time, these were other Bench Program members, but none of them were in the same class group I was in, so I had no knowledge of these people and only slightly knew a couple of the people in the room.  We were told to go ahead and go into the room and wait for a while by one of Steve’s assistants.  At this point, it still was not clear why we were there.  Then a gentleman came in and introduced himself as the monitor for the meeting, he was not a Microsoft employee, but some consultant Microsoft had hired to run this little dog and pony show.

It soon became clear that this meeting was really going to be some weird young executive meat market or talent show for Steve Ballmer.  The moderator asked us to come up with key issues for Microsoft that we wanted to talk to Steve about when he got there.   As a group, we were to identify the topics and present to him why we thought they were important to discuss.   The moderator told us we would have 30 minutes to pick the topics and who will present them and that he would be back just before Steve arrives.

Moments like this is when shit got really weird at a place like Microsoft.   Figuring out who is going to talk and what about, agreeing on the topics, it was like an instant chess match unfolding before your eyes.   Game of Thrones style, everyone was working through the right way to look good, please the king, and not come off looking like a total jackass.  Most everyone was failing miserably at the task. 

Unfortunately for me, I was a young and overconfident fool, so I opened my fat mouth and said I thought we should talk about competing with Google.  My reasoning was that Google seemed to be enjoying a strong connection with technical Reviewers and Press analysts I had been visiting as of late, and many of them had told me that we should be looking more closely at them. Some were suggesting that Microsoft should start forming a partnership with them or be looking to buy them.

At that time Microsoft had a product called MSN Explorer which was essentially a customized version of Internet Explorer with a bunch of buttons and chrome on it that pointed users exclusively to MSN properties.  As part of my job leading MSN PR, I had recently been out pitching the product to the press.  Most of the press basically liked the product but they did not like how it handled the Internet search function.  The search functionality was locked to use only MSN Search at the time.   I had several reviewers tell me that they would never use or recommend a product where they could not use Google as their primary search engine.  The cognoscenti of the tech media had already made up their mind that Google was important, and it was the best Internet search engine available on the market.   It was concerning to me and I felt like Steve should know about it.   This was the VERY early in the days of search.  It is hard to believe that Google didn’t really get started in search in any serious way until about the year 2000.  Adwords had just been invented and were just starting to roll out on Google. 

So, like an idiot, I told Ballmer that I thought Google was beating us badly on Search, and that important folks in the industry were telling me Google was going to be a really important company.  Before I could get much else out, he stopped me dead in my tracks.   Ballmer said, I have looked extensively at the Search market and ran the numbers, I don’t ever see search being more than a $300 Million-dollar business.  (Yes he was very wrong, but that really doesn’t matter)

As a young guy trying to move up inside of Microsoft, I was not about to challenge the wisdom of our CEO in a training class where I was supposed to be learning how to be a leader inside of Microsoft.   Steve was a renowned numbers guy, he was the friggin CEO of the company,  and who was I to question whatever math he had done.  I slinked back into my chair, and just sheepishly said,” I don’t know about the revenue part, I only know what others are telling me who I have talked to across the industry”.   He gave me a look like, “who gives a shit what those people are saying, I am the CEO of Microsoft!”.   I failed that meeting.  Big time.

I found out that later that day that Ballmer had called the VP of my division, Yusuf Mehdi, and told him I was a whiner or had a bad attitude or some such thing.  Yusuf caught me later that day in the hallway and said to me, “what did you say to Steve? He thinks you’re a real pain in the ass now!”   I, of course, thought to myself, “oh shit, I must have really pissed this guy off if he took the time to call my boss and tell him he didn’t like me, that went way worse than I thought!!!  I was devastated.  I wondered if my career was over that day, and sort of wished that it was.

I spent the next few years trying to avoid any eye contact whatsoever with Steve Ballmer.  I was just hoping he would forget who I was at that point.   It was an awful experience really, not just the meeting with Ballmer, but the entire Microsoft bench program in retrospect.  By the time I finished the program, half the people in my study group had quit the company, and only a few remained in the program as most just didn’t see the point of going anymore.  It was yet another signal that I missed that I should probably be spending more time thinking what to do beyond Microsoft.    But the primary lesson was more obvious.   As the old saying goes, God gave us two ears and one mouth for a reason.  I wish God would have provided me a muzzle on that day!  

Learning Lesson #14 – When you are a lower level employee in a big, highly competitive company with a cutthroat culture, be very careful when speaking your mind about what is going wrong in front of senior management. 

First, it is important to understand that CEO’s and Senior Executives have probably already heard about the problems you are worried about before.  They are after all running the company and it is unlikely they are totally clueless where the problems lie. 

Secondly and more importantly, in my experience at Microsoft, senior executives honestly don’t really care what you think.  Mostly they want to know that you are loyal to them and that you are not going to rock the boat too much or make them look bad.  

I am sure this is not true in all companies, and Microsoft was for sure a unique culture in those days.   But generally, I think this is true at most big companies.   You are way better off keeping your mouth shut while early in career, continue to try and learn and grow your perspective while trying to move up the ladder. 

When you are early in your career, your job #1 is to make your boss look good.  Just repeat it to yourself, “nobody really cares what I think”.  It hurts, but it will help you move up the ladder and set you up for success later down the line.   

This is particularly true in an environment where the senior management is paranoid.  Which happens to be almost all big tech companies in this age.  Voicing problems and concerns are often seen as a sign of disloyalty or weakness to the leadership in a tech company.  Where the culture is based on fear, you have little to gain by expressing problems.  Even if you think you have a solution to the problem, it is likely not going to be welcomed advice.  Of course, HR departments, and senior managers will tell you they want to hear all your ideas and to bring them forward.  But be very wary of that message, HR will tell you a lot of things in the corporate world that are simply not true, and if you are looking out for your career, you will do better keeping your mouth shut and going along with your senior management.   The fact is the paranoid senior management at your company is likely already very well aware of the problems you see and they have probably already debated them endlessly in meetings you weren’t invited to!  So don’t try and be a hero – it will leave you looking like a zero. 

The ONLY exception to this rule is that if you have a problem that you think could be damaging to your manager, and you have real data, NOT JUST GOSSIP, that will back up your point, it is worth sharing that data with your manager in a private meeting with ONLY your manager.   The problem and the data should be presented in a non-impassioned and straightforward way, and you should not bring a strong opinion to the matter.  Rather, you should simply state that you thought it was important that your manager knows of the issue, and if they need any other assistance that you are there and ready to help!

As you build trust and loyalty with your direct manager, you will eventually be able to extend that trust to take on more responsibilities and your opinion on problems will matter more – not only to your manager – but eventually to others in leadership.  Take it slow, and don’t shoot your mouth off as a young gun, it is a really stupid way to shoot yourself in the foot! 

Chapter & Lesson #13

Chapter 13 


“It takes a leader to create the momentum, it takes a vision to direct the momentum, it takes a massive action to build on the momentum, and it takes self-discipline to sustain the momentum. Momentum is the bridge between a vision and its results. 

Farshad Asl 


After the big launch of MSN 8, and the total self-destruction at AOL Time Warner.  The damage was done,  AOL no longer looked like a threat to Microsoft.  The momentum had changed, for both companies.  New Internet darlings were being formed, and the fear of AOL stealing Microsoft’s relevance seemed almost silly in retrospect.   Many in the division said that we had followed AOL right over the cliff.  Now both seemed to be dead.   To me that description, while harsh, felt accurate.  MSN was still losing money and had no clear reason for existing now.   Sure, everyone at Microsoft understood that the Internet was important, but it was now less clear how important it was to Microsoft specifically.   Microsoft was still selling Windows and Office successfully and was becoming increasingly strong in the enterprise software space.   Leaders all across the company were growing tired of losing money on MSN, without the threat of irrelevance looming from AOL, the investment in MSN seemed more and more pointless.  

Without a raison d’être the MSN  Division was sent into a state of chaos.   The battle was over, Windows had no looming threat from AOL.  Yahoo! looked like an interesting business.  But never seemed to represent a big threat or big enough opportunity for Microsoft to take seriously.  Google was starting to look like a serious business to many of the people who worked in MSN, but CEO Steve Ballmer seemed to have absolutely no clue of how huge search would be.   Ballmer totally missed that Google was setting up to shake Microsoft to its core.   All the winds were out of the MSN sail.  It was a division with no momentum at all, it was losing gobs of money, and had no clear idea how it would ever make a profit.  MSN’s biggest problem was becoming its own existence. 

For the next couple of years, MSN and the Online Division at Microsoft was basically totally rudderless.  There would be multiple executive changes at the top, along with constant staffing reorganizations laced with new memos stating where the new focus would be.   As a middle manager, it got to the point that it was just embarrassing trying to explain the new goals and strategies the latest executive wanted to go after.   Almost every 6 months there would be a new division leader, new lieutenants would be named, and reorganizations would become a routine of life while working in that group.  It was painful to watch and be a part of it.  The silver lining is I was being paid well to put up with all of the nonsense.   Otherwise, it would have been totally intolerable. 

The oddest reorganization I remember was when Steve Ballmer named a guy who was a friend if his,  and one of his “mentees”, to head the Marketing and Business functions of MSN.  This guy (who I won’t name) had made his reputation at the company leading the battle against Linux.  Linux is an open source software program for operating systems, where people and organizations donate code that is then freely available to anybody who wants to us it.   Open source was considered to be a huge threat to Microsoft’s proprietary and closed Windows Operating System, where Microsoft made most ofit’s huge profits at the time.

This new guy’s claim to fame at Microsoft was that he had crafted a marketing campaign called “get the facts” which was a successful competitive smear campaign on Linux.  It used all the fear uncertainty and doubt you could muster up, to scare IT managers and developers away from using Linux.  Steve loved it, and apparently loved this guy.   Within a few weeks of him landing in our buildings across the freeway from Microsoft’s main campus, it was clear that this guy was a gun slinger.

One of the most outrageous things about the new guy was that he had 2 business managers, one of whom was an extremely attractive young female.  The other, who was not as attractive, seemed competent enough.    (It is not unusual for a senior executive to have a one business manager at Microsoft.  These roles basically do all the dirty work that executives don’t want to deal with.  They organize staff meetings, they take personnel meetings that the executive himself does not want to take or have time to deal with, they deal with administrative type stuff)   The consensus on the team was that 2 business managers for this relatively small group was far from necessary.   More concerning to the business, nothing was happening with this guy’s leadership, he seemed to be traveling all over the world, not leading the group in any direction at all, or making any decisions.  One odd side note, that everyone on the team noticed, was that his beautiful business manager was traveling with him on extended trips.  This was very unusual, in fact, it was much more common to see business managers stay back at HQ to handle any routine things that might come up while an executive was out traveling into the field.

On one of those trips, apparently, Steve apparently received a heads up that some hanky-panky was going on.  To Steve’s credit – he put an immediate end to whatever was going on, and this particular leader never returned to Microsoft.   The details were never revealed to the team on exactly what happened.  But it was clear, something had gone very wrong with this rising star’s career, and it was likely a result of personal misconduct.

That VP’s firing was sort of a sign of the rudderless times in that division.  Another leader lasted only 6 months before he had a nervous breakdown.  Another was hired in from Kimberly-Clark who had worked on the Pampers brand, she was a disaster.  Diapers and software are not very deeply related, I remember a meeting where I had to explain to this person what Internet Explorer was, literally she did not know what an Internet Browser was, or how it was different from Yahoo (the web portal).   I knew she would not last past 6 months in that job, and she didn’t.    I could never quite figure out why she was hired in the first place.  

The place was a mess.  We had a running joke on the team that our job was to educate the newly named executives as they passed through the division.  We put a sign up on our doors that read “EEC” which nobody outside of our group knew what it meant, it stood for “Executive Education Center”.  It was one of the more idiotic corporate jobs I had ever been a part of.  I finally decided I had too much of the drama, the stupidity and the bridge to nowhere mentality that was taking over in the online group.  I started looking to get out and move to a division with more focus and better opportunity to keep my career moving forward.   It was a wise move.



Learning Lesson #13   Momentum is as important as any feature when working Technology.   I was lucky enough to get an up-close view of multiple big platform battles while working at Microsoft.  I learned that “capturing the narrative” of winning momentum is as important as any product feature you can deliver.

Momentum can come in many forms.  You can be far behind a competitor, but if you are stealing away market share from them, you can translate that into your own momentum.   Or you may be losing a lot of money in a business, but if you are reducing that loss significantly QTR over QTR that also counts as momentum.   You may launch an obviously technically superior offering, and if you can keep that superiority gap over the competition, even if you are not gaining share or profits yet, that can still be good for momentum.   

The ultimate in momentum is when you are taking share, increasing profits and or gross margins, and delivering a product that is perceived as better than the other guys.   If you have all of these things in your favor at any company or division, you will be riding high while it lasts.

Momentum convinces the press, customers, partners, and even your own employees that you are winning a battle.   The momentum is what creates the necessary resources to keep the battle well-funded, and the army well motivated.   If momentum dies you go to the grave with it, this is what happened to Nokia, Blackberry, Netscape, HP, Yahoo, MSN, AOL, Bing and a host of so many other great companies and products.  

You can be way behind a competitor, but if you have more momentum, if you are stealing away market share, mind share or both, you can be perceived as winning. 

This is a critical element to recognize in technology competition, primarily because things change so quickly in technology.  You can be the leader one day, and in the doghouse the next.  Technology companies run on fear, and if you are not beating the competition, you are losing.  In the winner takes all world of platforms battles, losing means long days trying to reinvent your product, your company, and your reason for being.  Thus momentum is everything.  

If you find yourself in a place where there is no momentum and little hope in finding it, consider making a move elsewhere. 


<<<On to Chapter 14>>>

Chapter and Lesson #11


Life is either a great adventure or nothing.”  

Helen Keller

Three of the more incredible and memorable experiences I had while at Microsoft happened in the midst of the hyped up battle between AOL and MSN.  The next few chapters cover a few of the more personal experiences and stories I experienced during my time at Microsoft.   I think they are worth sharing in this book because they are both fairly interesting and they highlight the importance of adventure in a long career.

When I look back over my time at Microsoft, there were many days that basically just fell into the trash bin of long & boring corporate work days.  Any career that spans more than 20 years is going to have ups and downs, and more than its fair share of days that are nothing more than the average day on the job.  The unique adventures and the stories and learning around them are what makes work and life interesting.

If I had it to do all over again, I would have jumped at taking on more adventures and pushing the boundaries much further.   The best and most interesting parts of any career are the times where you are taking risks and doing new things.   Those risks and adventures can come from lots of different paths you take when you work at a big company.  As discussed in the last chapter, joining a division or group of your company where there is a big strategic battle is one way to ensure that things stay interesting and exciting.   Another great way to keep things interesting is to go out into the field as often as you possibly can.  Getting away from the Company HQ when you are in a big company is a really important way to experience new learning, hear directly from customers, partners, investors, press and whoever else might be taking interest in your business.   I was lucky enough to have the opportunity to see a big part of the world while working at Microsoft.   I am super thankful for the experiences, the learning and the adventures I had along the way.  While some of these events were stressful and very difficult, they helped me become the person I am today and have helped me to appreciate all I have now. 

September 11th, 2001

One of my biggest adventures on the job happened during the 9/11 terrorist attacks.  I was scheduled to do press briefings and updates on MSN’s business and product offerings the same terrible week of the terrorist attacks on the East Coast.   As fate would have it, my original schedule had me set to be in one of the smaller neighboring World Trade Center buildings on the actual day of 9/11.  Luckily for me, my schedule had shifted around based on the availability of Walt Mossberg and a couple of other important technology reporters.

In fact, as I remember it, Mossberg was in NYC the day of 9//11 and he was scheduled to fly back to his home near DC that very morning.  So instead of being in NYC on the day of 9/11, I was in Washington DC.   I was staying at a fancy hotel just steps from the Capitol Building the night of September 10th. I had flown in the day prior as we normally did when doing press tours on the East Coast.   I got up early that morning of 9/11 and I turned on the TV in my hotel room.  I remember I was ironing a dress shirt for the day, and looking at the TV getting caught up on the latest business news.  I was watching CNBC, and the anchor was Mark Haines, who by the way,  was an awesome and entertaining anchor for CNBC for many years. He has now unfortanetly passed away. I was watching Haines do one of his classic interviews with Bill Nygren of the Oakmark Select Fund, the market was not yet open.  It was approximately 8:50 in the morning.   (You can see the coverage here.)  

I  can clearly remember how Haines calmly covered the first plane hitting the first Trade Center building.  He quickly cut over to the live pictures of the tower on fire.  He called it a significant problem and didn’t speculate very much further other than to say it was safe to assume there was probably some fire in the building.  His coverage was excellent all the way through, and if you have never watched it, I recommend it, as it was a defining moment for Haines and for CNBC in my opinion.   It was truly excellence in live journalism.

Because I was scheduled to be in NYC the next day, and I was previously scheduled to be at the WTC buildings that very day! I was now on full alert! watching the horror unfold.  It took only a few more minutes to confirm on live TV that it was a plane that had hit the first tower and that a large hole could be seen in the building.   At 9:03 EST, for just a brief second the CNBC feed actually went out, and then came back and I (with millions of others) watched in horror as a huge explosion erupted in the other tower.

Like so many others on that terrible day, I just could not believe what I was seeing.  I was in shock.  I quickly called home to my wife back in the Seattle area and told her to wake up and turn on the TV.  She was back home with my young children and on West Coast time, so it was still really early and she, like most others on the West were still just starting to rise for the day.  I told her I would call her back and then quickly called my parents who were also on the West Coast and told them to turn on the TV, that something very major was happening.  I then called the PR Agency woman from Waggener Edstrom I was traveling with, Marla Polenz, and we discussed quickly if we should start to cancel our meetings for the day.  While it was obvious in retrospect, that all meetings would be canceled that day and for the entire trip, we had only had about 15 minutes to start to understand the magnitude of what was happening.

We both agreed to call back to our respective bosses and get a quick opinion on if we should continue on with meetings for the day.  I could not get a hold of my boss at the time.  Marla’s boss at Waggener Edstrom was Colleen Lacter, who is an awesome person and great PR leader, she suggested that we should plan to go on and do the meetings for now and see how things unfold for the rest of the morning.  It was a good thing she did as it kept us moving that hectic morning.  Marla and I agreed that we should meet in the downstairs lobby and see how things developed before we made a call on heading out to our first meeting.  As soon as we met in the lobby it was very quickly becoming obvious that there would be no meetings that day, and for the foreseeable future.

This was a good lesson in how fast things can change in life and in business.  I was up late the evening before, stressing out over every little detail of the meetings that were going to take place the next day.  Rehearsing our pitch, going over in great detail every point we wanted to get across, repeating the technical demonstration on my laptop over and over again making sure that everything was just right for the meetings.   In a flash, those meetings now seemed totally meaningless, there were much more important things happening in the world.  It was a good reminder to not take yourself too seriously.  Something always worth keeping in the back of your head.

The particular hotel we were staying in was very close to the Capitol Building, just a couple blocks away and you could see the Rotunda from the street in front of the hotel.  We had a driver who was to be waiting for us out front that morning.  So I went out to the front of the hotel to see if he was there yet, when I poked my head outside I saw that the entire street and sidewalks had been totally shut down.  There were black government SUVs everywhere, D.C. cops, secret service people and bomb dogs all over the place. With all the different black cars parked and mostly sitting empty in the street, I had no idea which car was intended for us, and all traffic was essentially shut off in the street.  I raced back inside the hotel, on the TV’s in the lobby at 9:30 AM President Bush made a statement that he was heading back to Washington from an elementary school visit he was doing that day in Florida. In his statement, he confirmed that this was a major terrorist attack on the country.

By 10:00 AM a full evacuation of the White House, the Pentagon, and the Capitol had been put into action.   The hotel was asking people to stay inside and in the lower lobby area on the first floor in the event that any more planes were still trying to hit the Capitol.  At this point it was more than clear, we were experiencing the worst thing that had happened to America in a very long time.   

Marla and I got very lucky that our driver for the day had come inside the hotel to wait for us.  His car was still there at the hotel and we found each other in the hotel lobby.  By the time we found the driver and realized the severity of all that was happening it was announced that all air travel was now grounded, it was clear to me that we were not going to easily get out of D.C.  At this point, we were rattled, I personally just wanted to get away from the city.  It was a combination of fear, emotions and my natural inclination of just not liking big cities very much in the first place.  I simply wanted to get away from the D.C. area ASAP, and more than anything wanted to be home with my family.

I asked the driver if he would wait for us to gather our luggage and take us out of town.   He said he would.   Marla and I grabbed our luggage from our rooms and raced down to meet the driver and get to the car.  By this time they were allowing people to now leave the hotel area and go into the streets, all flights had been grounded are diverted away from D.C.  The driver asked where we wanted to go, I asked him to just “Head West” and we will figure it out as fast as we could.   He took us out of town on the I 395 which travels right by the Pentagon.  We could see the flames coming from the Pentagon where the 4th reported plane had come down.  It was extremely scary, eerie and horribly sad to see.

We quickly came up with a plan to try and get a rental car, so that if nothing else, we could be far away from the D.C. area for the next few days until things calmed down a bit.    

We found that the closest place where we could get a car would be at the Budget Rent a Car at Arlington Virginia.  This particular Budget has both Trucks and cars.  By the time we got there, they were down to the very last couple of cars.  In fact, the agent there told me that the only car we could have was a local rental and had to be returned to the same office.  I told him that was fine, we would find a way to get it back to him.  As we were getting the car rented at the front desk, more and more desperate businessmen and women were streaming into the rental office to try and rent cars, all wanting to get out of town as fast as they could.  I vividly remember a group of three businessmen from Florida who wanted to head home, there were no more cars, so they rented a big box truck and had planned to take it all the way to Florida.

Marla and I felt very lucky to have secured a rental a car, it was a nearly new Jeep Cherokee, we started driving West without a clear plan to start.  As it turned out, Marla had a family wedding she was planning to go to in Nebraska after our meetings that week.   We talked about it, and I said, “well, we might as well head there, I will drop you off in Omaha and continue west until planes start flying again and will catch a ride home from there”.   It is around 1100 miles from Arlington to Omaha, it took us a couple days driving to get there.  I think Marla was ready to be done with me after that trip.  I was happy enough to continue the journey home alone.   We had some fun along the way chatting about things and getting to know each other, but that was a long and unplanned road trip for two people who didn’t know each other very well.   We ended up becoming pretty close colleagues after that trip.  We definitely had some laughs after it was all over. 

After dropping Marla off in Omaha, I ended up driving toward Wyoming.  I learned that Nebraska is a VERY long state.  The I80 portion of Nebraska is 455.27 Miles long.  It boasts 25 rest areas, 82 interchanges, and One scenic overlook.  Driving that distance alone through the hundreds of miles of farmlands with nothing more than a radio that was airing constant talk of the terrorist attacks was very depressing and isolating.  I started to regret my attempt to drive home and wished that I had just stayed in Washington until flights started going again.  But I was too far gone on the journey by that time.

It is hard to imagine now, but the 9/11 attacks actually happened before the advent of the iPod – which wasn’t launched until October of that same year in 2001.  So we didn’t have smartphones,  Facebook, Twitter or any other technology during that time to keep us both connected and distracted about the events of the day.   I think if we had all of those things back in 2001 it is probably more likely that 9/11 may have never even happened.   Or, quite possible that much more of it could have been thwarted.  The speed at which information now travels and the connectedness of people make it more likely that somebody may have found out about the attacks before they happened and authorities might have been able to stop it.   Certain it may have been possible for people flying on the planes to get messages about what was happening and more fully rebel against the terrorists.   We, of course, will never really know if it could have made a difference, but it certainly seems plausible.  It is hard to even conceive of major geopolitical events like this happening prior to social media and access to always-on broadband connections.  Thinking back to my trip across the United States starting the day of 9/11 is like going back to a time that I can barely explain to my children.   The changes in the way we react, communicate, exchange ideas are completely different now.

I grew so tired of listening to the radio coverage of the 9/11 story for hours on end, I decided to buy a couple of music CD’s from a truck stop, I played them over and over and quickly grew tired of them as well.  For many hours I just drove silently, thinking how strange it was to be out there in the middle of the country driving alone, with no planes in the air and very few people out on the highways.  My work had stopped completely, nobody cared about the battle between MSN and AOL, it was completely insignificant in the world.  Silently driving across the vast plains of the country gave me time to think about how ridiculous it was for me to be so caught up and stressed out about my work.  It was a good time to do some reflecting on what was really important to me.  I think others had similar reflections on their own lives.  There were a lot of important cultural changes after 9/11.   Many families decided to spend more time together.  The display of patriotism was strong, church attendance went up, and people spent more time at home than going out.   Some of these changes were more long-lasting than others.   But no doubt, 9/11 was a major watershed moment for the USA.

The rest stops along the highway were full of other stranded business travelers and made for some entertaining encounters.  Everyone was trying to find their way back home to their loved ones in rented cars that had been flung all around the nation.  Everyone had their own story of where they were and what they were doing when that horrible tragedy took place.  Sharing that story was not something you put into social media in those days.  Sharing the story meant you were talking to strangers at a rest stop, or at a gas station or restaurant along the highway.  Looking back now, I see those times, as horrible as they were, as a moment that truly brought the country together in a meaningful way.   The spirit and love for America were strong at that time, people looked into each other’s eyes and shared their story.  And in that way, compared to how we communicate today, it was beautiful.   I spent one night in an old motel in Casper Wyoming, it was a fine place and it gave me some time to rest and relax, that night I decided to go up to Yellowstone National Park as part of my journey home.  My boss at the time was Christophe Daligault, a great guy, who was a Frenchman, he had an incredible marketing mind and a great spirit about him.  He encouraged me to take my time, relax and try and enjoy the journey home.  I figured driving through one of the nation’s most beautiful and iconic national parks might be good for me.  And it was.   

Yellowstone was almost completely empty the week after 9/11.    I will never forget the startling contrast of escaping one of the biggest catastrophes ever on US soil, leaving a city under siege and chaos and then ending up wandering around amongst wild buffalo in Yellowstone National Park in utter silence and serenity.  Yellowstone is possibly the most beautiful place in the world, the contrast was such a mind bending experience.  For me, it cemented my fondness of country life over city life.  The experience was one of transformation for me.  I viewed work and life and that balance very different after that trip.   I knew at that point that I did not want to spend the rest of my life fretting over small details, I made a bargain with myself to find a way to retire early from Microsoft, but also to enjoy the time I spent there as much as possible.      

Learning Lesson #11-  Take risks and let adventure guide you in your life and in your career.   The journey truly IS the reward.  It has taken me a lot of time, contemplation and perspective to really appreciate that fact.  So much has been written about how to achieve great success in life, how to find your passion and how to find a truly satisfying and successful life that you love.  One of my favorite books I have read on this topic is Ray Dalio’s -“Principles” In it, Dalio talks about the importance and the balance of taking on risks and challenges and truly embracing and learning to love the pain involved in learning new things and new lessons.  He advises that if one learns to love the process of making mistakes, love the learning from them, and advancing from each lesson, it becomes a formula, or a “machine” for achieving whatever goals you want in life.  In the book he walks through his method for how to think about loving that pain, and how our brains work for and against us when trying to embrace that type of learning.  His methods have certainly worked well for him, he runs the biggest hedge fund in the world, and by all accounts has had an incredibly good life.   

One other book I highly recommend on this topic is “The Element” by Ken Robbins.  This book covers some similar ground in Dalio’s “Principles” but focuses more on how to find your passion through a process of discovery.    If you are just starting out in your career, or still in school, this I think is a MUST READ book.  Every single very successful person I have ever known or studied has one big thing in common.   They LOVE what they do.  Finding that passion for some people comes early and very naturally.  For others, it takes more time, and sometimes it means you need to toss out some of the programming you have received from your education, or perhaps your parents so that you can find what you truly love to do.  Read Ken Robbins book to help you find your passion, he has some really useful ways to think about this.    

In my experience, taking on risks, and taking on as much adventure as you possibly can with your career is the best way to keep things interesting. New adventures will lead you to new areas you likely never knew would excite you and bring you new success.   When things go wrong, learning to feel the pain and embrace that pain as good thing will also teach you what you don’t like, and as you embrace that pain, and use that as a force for good, you will grow and find new heights of success. 


Chapter and Lesson #10

Chapter 10 


“The four most dangerous words in investing are: ‘this time it’s different.’” 

 Sir John Templeton 


I landed a role in Microsoft’s buildup of a team that was going to go after the dial-up and internet king of the day – AOL or America Online , it was a new war for Microsoft, with many veterans of the browser wars taking on new leadership positions in the fight against the newly merged AOL Time Warner.

My first role was in PR, but this PR job would be very different than the role I had in Windows Marketing, and this would be where I received my first promotion to being a Group Product Manager, my first time managing other fulltime employees at Microsoft.   I honestly can’t remember if I was ready to manage people, and thankfully I only had a handful of employees at the time, with well-defined roles.

I am almost certain I was a terrible manager.  First-time managers usually are, and I see no reason why I would have been any better than average.  Most of the skills developed as an individual contributor don’t translate to being a good manager.   I had previously done most of the tasks that each of the people on the team had assigned to them, so I was comfortable enough taking on the role of managing these things.  The problem with first-time managers who previously did many of the jobs he or she is now managing is that they think they know how to do the job better than anyone else.   It takes time and a lot of experience to appreciate how to get things done through and with others.  That is a different book altogether, but a topic that tech companies need to figure out better and fully embrace.

My job was to orchestrate a narrative that Microsoft was serious about competing with AOL.  And, In fact, we were serious.   The company was spending literally BILLIONS of dollars, and taking huge losses that impacted Microsoft’s bottom line to try and slow down the AOL juggernaut. When the effort first began, nobody was really taking Microsoft’s competitive threat serious, so we set out to prove to the press and to Wall Street that we were indeed very serious, and we were going to spend like crazy to compete and catch up to AOL.   They had a big lead, and all the momentum in the marketplace, so proving our ambition was not going to be easy.

The spending to fight AOL was ferocious and the tactics involved in doing so were at times absurd.   I remember at one desperate point in the battle, we hatched a plan to give customers at “Radio Shack” $400.00 to spend immediately in store if a user would sign up for 2 years of MSN Internet access on the spot.   Just as soon as we implemented the plan there were reports of people coming into the retail stores multiple times under fake names, bogus credit cards who were walking out with brand new TV’s and DVD players from their 400 free dollars, courtesy of Microsoft’.  Radio Shack, of course, loved the deal as it drove a ton of traffic and purchases at the store, in hindsight, it was an idiotic and desperate move.   Making things even worse for Microsoft’s financials, we agreed to pay a bounty to RadioShack for every customer who signed up!  There were similar deals offered at Best Buy, Office Depot and other retailers.    It was was a crazy tactic with insane spending to try and steal share away from AOL.   

At the height of it all CNet had reported on a story that covering Microsoft’s earnings “Retailers relied heavily on $400 MSN rebates to sell PCs during the holidays. Customers agreeing to make a three-year MSN commitment with their PC purchase received an instant $400 rebate subsidized by Microsoft. 

But Microsoft also extended the rebate to other non-PC products. Retailing giant Best Buy, for example, sold 200,000 MSN subscriptions worth about $80 million in instant rebates on anything in the store. 

“Obviously stores used the rebates to drive sales across other categories,” said PC Data analyst Stephen Baker. “It means maybe people aren’t as tied to the Internet as a PC thing, so people used that $400 to get a big-screen TV.” 

It was crazy and some would say it was totally out of control spending, all to try and eliminate the fear, and kill off the AOL Time Warner monster.  

To give you an idea of how crazy and frankly unethical things had got inside of Microsoft at that time, they set up a top-secret competitive intelligence group to try and track every move of AOL.  Microsoft even hired private investigators who dug through AOL’s garbage.  At one point there was even an employee who started dating a girl from AOL just so he could collect intelligence.   The Microsoft employee had convinced her somehow give him access to a private internal phone conference call bridge number where the team would sit and listen to many of AOL’s internal conversations.    Later these employees would receive a slap on the wrist for going too far on gathering intelligence.  But it was widely known that this group was pushing the boundaries of corporate “intel” gathering, though most were rewarded and or later promoted for their efforts.   In a very strange twist of faith, one of the employees involved was later arrested for embezzling millions of dollars from Microsoft.     I guess you reap what you sow.

The name of the game was to take away the momentum from AOL, make them look vulnerable, show the marketplace that MSN had a serious competitive offering, and start to erode the finances of AOL to take the wind out of their sails – and their sales I guess too…    Indeed the narrative started to work.   Each Quarter both AOL and MSN would announce how many net new subscribers they had gained.   It had become a brutal game of churning and battling for customers.  The customer acquisition costs for both companies were going through the roof.  It was an arms race.  And MSN with a smaller base of customers, and ridiculous offers in the marketplace was able to show accelerating growth that was outpacing AOL’s customer numbers.   The market started to take the threat from Microsoft very seriously.    Momentum had shifted.    Microsoft had a competitive offering.  And at the same time, AOL was hitting the wall with 3 other nasty problems.    

1) The .com bubble was bursting – revenues from companies who were paying huge sums to advertise on AOL’s network were evaporating as fast as companies like were going bankrupt.  The outlandish advertising revenue projections AOL had made to justify their merger with Time Warner were looking obviously inflated.    

2) The merger of AOL and Time Warner was breaking down into a mess of two cultures who hated each other – it was a disaster.  Wall Street coined it the worst merger ever in history.  

3) Broadband was starting to take off and customers were ditching the slow dial-up access provided by AOL to move to the new fast and always on connections provided by their phone or cable companies.   AOL never “owned the pipe” or really any of the actual infrastructures that was carrying the bits and bytes through to the telephone modems to a consumers PC.   They were an easy way to get onto Narrow Band access, and the original “training wheels” for the Internet for the first time, but as people switched to faster DSL and Cable Internet access, they had little use for AOL’s proprietary network.

AOL had missed the strategic inflection point of Broadband mass adoption.  Broadband was always connected, versus AOL’s Narrow Band which used special software which connected the PC to a modem on an old fashioned phone land line.  This software called a “dial-up stack” was one of the differentiated things that AOL had made easy for customers, and it was their bread and butter product that was now no longer relevant.   AOL had thought that their content and services would be the differentiator, and they made a bet that combined with Time Warner they would be able to hold their lock on the consumer market by packaging all the content and services together, even if users did not need AOL as their everyday onramp to get online.    

Over time this proved to be a foolish bet, the World Wide Web, and democratization of inexpensive publishing onto the Internet was a much more powerful force than almost anybody had anticipated.    AOL Time Warner fell into a total meltdown.   It missed the next big thing that was coming, the idea that any individual could publish content for negligible cost.  Content was exploding all over the Internet in the form of blogs and new digital-only publications were more popular than the old analog content that Time Warner was slowly moving toward the digital age.  The great hope of combining Time Warner’s content with AOL’s technical know-how was now looking like a dubious value proposition.  Stockholders in this deal were about to lose their shirts. 

The value of the combined AOL Time Warner sank from $260 Billion to just $20 Billion in a few short years.  The company was forced to write down $99 Billion of “goodwill” assets less than 2 years after the acquisition was complete.

This story is really not all that unusual in the tech sector, but it does illustrate on grand terms why tech leaders are so paranoid, and how fast fortunes can change as technology platforms shift and consumer behavior changes.  The tech sector is littered with these irrational buildups, buyouts and mergers, there are many of them out there today that will end up the next great business flop.  Be careful not to indulge in the irrational valuation of these seemingly “brilliant” next big things.   It is a good way to lose a lot of money.

Learning Lesson #10- The Tech Industry is full of incredible hype and has a massive herd mentality, picking the Winners and Losers is EXTREMELY difficult and can be dangerous for investors.  If you are an investor or somebody who works in the Tech industry.  It is useful to look at the history of the wild swings and the herd mentality thinking that repeats itself again and again in the industry.  Tech is really a series of micro booms and busts of different micro cycles.   It is very difficult to predict both the timing and who will be the winners and losers of the next big wave in tech.   There have been lots of booms and busts in tech.  The .com boom and bust is probably most widely known and understood because of its incredible meltdown of the NASDAQ in 2000.  But there have been many other tech sector buildups and meltdowns.  3D Printing, PC OEMs, Console Gaming, Instant Messaging, Search, Mobile Phones, Social, and many other sub sectors of tech have seen huge crazy run-ups of investment followed by harsh periods of consolidation and price correction.   The same types of buildups will repeat with Wearables, Internet of Things, Electric and Self Driving Cars, Virtual Reality and more.   Globalization, Cloud Computing, and super-fast transcontinental fiber optic communications are hastening the pace of these buildups and meltdowns.  Wall Street is always trying to predict who and when the next big winner will be in one of these hyped-up areas.  Unfortunately, they are almost always wrong, and when they are right, they almost always way overvalue the opportunity to the point where when the damage comes, it cripples the company involved and the reckoning day is very painful for those who have to do deal with it.  If you are an investor, an employee or a partner company of a newly unloved sector or company it can be extremely painful.  But this is what tech is all about, and like it or not, much of the economy is now becoming part of this rapid boom-bust cycle of innovation. 

Chapter and Lesson #9


“The Chinese use two brush strokes to write the word ‘crisis.’ One brush stroke stands for danger; the other for opportunity. In a crisis, be aware of the danger–but recognize the opportunity.” 

John F. Kennedy 


The Internet browser wars were now officially over.  Some at the company felt that the hard fight had done more harm than good.  Many believed that the flamboyant victory over Netscape inflamed Microsoft’s already arrogant reputation.  The Internet Explorer Marketing team I worked on was merged back into the Windows team.  Which made sense, given the argument to the DOJ from Microsoft was that Internet Explorer was really just a feature of Windows and Microsoft had every right to add new features into its operating system.  So it did not look very good to have an entire Marketing or Development team dedicated to a single feature called Internet Explorer.

Having a separate operating unit didn’t really look all that great, and made even less sense when it was clear the war was over.   So the IE team was fully integrated back into the Windows Marketing team.  This turned out to be sort of an odd event for me personally because the Windows Marketing team was the group I had left from to go to the Internet Explorer team.  We were not given any choice as to if we wanted to go back to the old Windows team.  If you wanted to keep your job, you were told that you would be going back to the Windows Marketing team, like it or not.    I did not like it – and didn’t want to go back to marketing operating systems again, but I figured a good job at Microsoft was better than a bad job and some other lesser company. 

For me personally, Microsoft was becoming a less satisfying place to work.  However my life was moving on, I now had a wife and a family to worry about.  Even if things were not as fun and lucrative as they once were, Microsoft was still a very generous company to work for and there were still solid jobs available.  It was different now, it was more like a regular job at any big fortune 500 company.  Probably better than most companies, even with all the new red tape, and problems.  Microsoft was still clearly better than most companies to work for.  

In the transition back to the Windows Marketing team I was fortunate to have landed into a decent job for me.   Prior to the announcement of the IE team being reorganized back into the Windows team, I had already been moved to a new role working in Public Relations for Internet Explorer.  I was able to move into the PR team for Windows as those two teams were being merged together.

My specific job was to work with Technical Reviewers who would be writing product reviews for the upcoming release of Windows 2000.  This was a stretch for me technically.  I was pretty deep on the various browser technologies after spending years working in the browser wars.  But I was far less deep on Windows.   Particularly the enterprise features of Windows, which I had really never paid a lot of attention to.    I jumped in and learned all I could as fast as I could.  I took all kinds of training classes to become a certified Windows Administrator, I went and interviewed all the Windows engineers I could to get every last detail of every feature of the product.  It was my job to write the Windows  2000 “reviewers guide” which outlined every feature and why it would benefit customers.

This job opened an entirely new world to me on how technology companies position and promote their products to the technical press.   Microsoft and its PR agency Waggener Edstrom spent countless hours planning and debating every single detail on how a new release would be messaged to the press.  I could write an entire book on all the behind the scenes plans, strategies, antics and drama that played out leading up to a big product launch for Microsoft.  Microsoft was really good at doing big promotional launches of their important releases.  The pinnacle and blueprint for big launches was the Windows 95 launch, where somehow Microsoft created enough excitement for a new Operating System that people literally camped out overnight at retail stores to get their personal copies!      I can’t imagine that kind of excitement for an Operating System today, but those were very different times.   I think people mostly loath operating system updates these days, they always seem to drizzle down to your computer overnight and want to be installed right when you are doing something important in the morning.   

The core objective of my job was to make sure that every single technical review of Windows 2000 was positive, or what we called a “WIN” review.   I probably should have been more intimidated with such a stretch assignment.  But I was still young and dumb, and also very lucky to be assigned to one of Microsoft’s best OS releases ever.  Windows 2000 was a rock solid OS for that day and age, built on the Windows NT architecture that was designed to be much more reliable and stable than the old DOS-based operating systems, it was designed with Enterprise customers in mind.   The product received fantastic reviews; this was a win for Microsoft and a win for continuing my career progression.  Winning reviews with a great OS was actually pretty easy, but I ended up getting a lot of credit for being part of the effort, and that was great for my personal fortune.  Microsoft has had its share of total flop OS releases.  I always felt sorry for whoever had the job of winning reviews for Windows Me, or Windows 8.  Those were dogshit OS releases, which no PR person could truly overcome, no matter how good they were at spinning.    

Windows 2000 and Windows 2000 Server launched together at the same time.  So this was a really important release for Microsoft because it was really the first time they simultaneously released both a new desktop and server release.  There was a LOT riding on this for the company, so we worked very hard on a massive PR blitz to win reviews.  We held a huge reviewers workshop conference where we brought in the press from all around the world for three days of intensive education sessions on the product.   The PR team I was on traveled all over the country visiting technical reviewers wherever they lived or worked to sit down and walk them through updates of the product and discuss any concerns they might have.   The idea was to get reviewers so bought into the product prior to it launching that they would actually feel bad about saying anything negative in their reviews.   We made them part of the process and fully and deliberately brought them into the tent.   It was not unusual for the product team to change a feature, or remove something that was highly disliked by a technical reviewer.   If a reviewer experienced a certain problem they could not work through when testing the product we would fly a swat team out to help them through it, and if necessary we would again change the product to satisfy them.   It was an intense job, and I was always on the go for many months on end.

After Windows 2000 shipped, I was able to take a bit of a break from the hectic pace of working on PR campaign for a big OS release.  Back in those times, it was common for employees to run as hard and fast as they could up until a product launch.   It was a huge part of the culture of the company.  After a big launch, employees would be exhausted and want to take time off to recover.  It was not unusual that people would quit the company altogether after a launch, or want to move onto a new job within the company.    

It was typical that divisional or full company reorganizations would be planned soon after a big product launch.  In some ways this was becoming problematic for Microsoft, the Internet was staring to take over and other companies were moving faster using agile development where features were released daily onto the Internet.   The old model of doing big monolithic releases of Windows and Office every couple of years with a huge marketing launch event was becoming more and more outdated.   An internal debate on the topic had started to take hold.

Recognizing these changes, and missing the fast moving days of working on the Browser Wars, I was eager to move to a new role.   Many of my best colleagues and friends from the Windows group had already moved on to Microsoft’s online division – MSN.   Brad Chase, a great marketer who had led the Windows 95 launch, along with Yusuf Mehdi, Lora Shiner, Christophe Daligault, and many others were now preparing to fight a new battle for the company.    

In January of 2000, AOL stunned the business world and announced plans to acquire Time Warner for $184 Billion in stock and debt.   It was an announcement that sent shockwaves through Microsoft.   At the executive ranks in Microsoft, AOL was already considered a credible threat to Microsoft’s dominance of the PC Desktop.  AOL was the undisputed leader in connecting consumers to the Internet and they were building out a broad set of Internet services and media properties.  With more than 23 million paying subscribers and growing quickly, the service was generating billions in revenue.  The success at AOL had poked the Microsoft bear.

A fear gripped Microsoft that AOL combined with the resources of Time Warner could eventually make Microsoft and their Operating System irrelevant.  AOL was the dominant entry point for mainstream consumers to go online, do email, instant message, chat boards and browse and consume content.  Fear Uncertainty and Doubt (known as FUD in the business) was palpable inside Microsoft at the time.  Steve Ballmer had taken a strong personal interest in the problem,  he even setup camp with an office in the RedWest campus (which was fully off the main campus at the time on the other side of the 520 Freeway)  where the online services division was located.    It was feared that if AOL could convince consumers to consistently pay them $23.99 a month in subscriptions fees, and be the gatekeeper to the Internet, Microsoft might lose relevance and the control of the Personal Computer experience.   

Microsoft was getting ready for another war, and it had a huge cash war chest to play with.  I knew from my Internet Explorer and the browser war experience, if you want to advance your career, it is better to go where the action is.  So I started making haste to find a role in the new battle.   That ended up being a wise move.   The next few years got very interesting.

Learning Lesson #9 – Corporate Fear Can Deliver Big Opportunities.  This lesson takes a little bit of explaining, but if you start to understand it you can likely play this to your own benefit. 

If you are a Senior Executive at a huge company, like Microsoft, your biggest fear is being made irrelevant.   In the technology sector, this fear is massive.  You need to only read one of many business books like  “Only the Paranoid Survive” by Andy Grove of Intel fame to understand this phenomena.   Grove describes “strategic inflection points” that can either be an executives worst nightmare, or an opportunity to win a major new marketplace. 

The stress of being made irrelevant very quickly in tech is profound because in the business of tech, pretty much all the spoils (money, power, future…) go to the 1st place player.  There is almost no profit in being a 2nd place player, and 3rd place is worse than not playing at all.   As an example, Facebook will make almost all the money in Social Media, Google in Search, Microsoft in desktop OS & Office Productivity Suites, Intel in x86 processing chips, Apple in phones, Uber in rides etc.   It is for the most part a winner takes all type of game in big tech. I can’t even think of a significant third place player who has made any money in a big tech market. 

Owning the platform for the hottest tech spaces is where all the riches are harvested. This is the way the economics work in technology.  If you win the platform, you will have all the best developers, if you have all the best developers they will increase the value of your platform with new applications and hardware to support your platform.  The ecosystem reinforces itself, and it quickly locks out other players.  

Executives at all big tech companies know this, and they always fear that something will somehow disrupt their dominant share position, and will bring on competition, or even worse, relegate their position to being irrelevant in the latest most important trend.   You want to be at the center of where these battles take place.  You want to make money from this fear.  So for example, if you work at Microsoft today, you absolutely want to be working on a cloud, but more specifically, you want to be working in highly competitive areas where Amazon’s AWS battle directly against Microsoft’s Azure.  Both companies will be fighting like mad for talent in these areas, and both companies will pay top dollar to talented engineers and marketers for their efforts.   This book is about learning how to thrive in these environments.   But it is also how to be in the right environment in the first place.   You want to be right where these companies are spending their war chests to compete.    Just being at Microsoft or Amazon in a random role is NOT GOOD ENOUGH!   To make the big money, you need to be in the exact right area where the battle is taking place.   As recently as April of this year Microsoft gave special bonuses to employees working in the most coveted areas of cloud development.  Up to $100,000 dollars in stock, just to make sure employees would not walk away.   I have seen this time and time again throughout my career at Microsoft, and I know other companies play the exact same game when competing for talent.

Even if your company does not stand a chance in hell of winning the battle, it is better to be working wherever the hot battle is happening.  Executives will spend crazy amounts of money to fend off potential threats, they will build big teams, create huge marketing budgets, and they will spend like drunken sailors to fight off the fear of falling behind.   This is where careers get a real boost!   When teams are building fast, and money is being spent like wildfire, that rising tide is good for all the boats (people) who are lucky enough to be in that division.   You don’t have to necessarily be the best, (but it helps) you just have to be there. 

I saw plenty of overpaid middle managers get pushed upward with money and responsibility as these manic buildups took place.   These things are easy to spot.  Look for the new strategic imperative spelled out by management.  The press will be squawking about the companies coming doom or possible glory because of some new company or trend wiping them out or being harvested.   Sometimes it is real, sometimes it is hype.  It is hard to know, but it really doesn’t matter all that much for your own personal growth.  You just want to be in the center of it, and rise with the tide. 

From a career perspective, if you are a lower to middle level executive at a huge company, it actually doesn’t matter that much if your company wins or loses in these battles.  It feels a lot better if you win, and it is more fun for sure.  But from the perspective of moving your career forward, it is better to be in the battle, even if you lose.    I saw a lot of great people sit on the sidelines at Microsoft in boring jobs, making OK money in a “OK” division while the people in the big battle divisions where raking in the new responsibilities and the money to go with it.   Those people in the OK divisions did fine, but they got nowhere near the career acceleration vs. people who moved to the strategic hot spots.   And my bet is that they probably didn’t have as much fun either.   There is money where there is fear.  Don’t be afraid.  The company will reward you, win or lose. 

That said, if you are at the top of the leadership team and you lose, watch out, you will probably get canned, and it is much harder for senior and midlevel executives to regain their footing from.  If you are early in your career, take the risk and seize the opportunity!