Microsoft vs. Apple: The Strategy Gap

By Ken Segall

Most people judge ads by what they see. Good ad, bad ad, end of story.

Of course, it’s a little deeper than that.

As is often pointed out around these parts, there’s a little thing called “strategy” — which is hashed out before creative teams start creating.

Historically, Apple has been very smart about strategy, while Microsoft has been very … shall we say … un-smart.

Now that Microsoft’s new CEO Satya Nadella has appointed Mark Penn to the position of Chief Strategy Officer, it’s a whole new ballgame, right?

Not so fast.

From what we know of Mark Penn, the gap between the quality of strategy at Apple and Microsoft isn’t about to shrink.

Microsoft’s newly minted Chief Strategy Officer, Mark Penn

For starters, Penn has actually been Microsoft’s Executive VP, Advertising and Strategy, since mid-2012. He’s the architect of the company’s tasteless, cutesy and much-maligned “Don’t Get Scroogled” campaign.

Penn has been quoted as saying that this campaign was a success. Not terribly surprising, given his background. To people like Penn, success is determined only by the numbers — with little appreciation for how great brands are built.

Penn was a major player in Hillary Clinton’s 2008 presidential campaign, ultimately “resigning” mid-primary season. A New York Times article in 2008 described him as “a sometimes brusque number cruncher with centrist corporate sensibilities [and] few friends inside the campaign.”

Penn was also CEO of ad agency Burson-Marsteller. According to a 2008 Time Magazine article, Penn’s former clients include “drug companies, a tuna industry group, a tobacco firm and the controversial military contractor Blackwater USA.”

I can assure you, those who work on strategy at Apple and its agency TBWA\Chiat\Day have strikingly different credentials.

To be fair, Penn offers one glimmer of hope for Microsoft fans. It is reported that Penn was behind the Microsoft ad that ran on the Super Bowl, which was actually one of my favorites during the game. (Though many felt it borrowed way too much from Apple’s latest ad style.)

What I’ve learned in my meager career is that strategic decisions have a scientific and emotional component. Apple’s wild success came largely from the fact that Steve Jobs used his head and his heart. He wasn’t oblivious to numbers, but he had a innate understanding of human behavior and made some of his best decisions by instinct.

The world of political strategy is different. It’s all about polls, research and numbers. It’s calculated. It’s about attacks and counter-attacks. It’s all head and precious little heart. This is the world that spawned Mark Penn. And it doesn’t offer a lot of hope to those who’d like to see the quality of Microsoft ads move in a positive direction.

My eyebrows went up when I read of Penn’s appointment, because in researching my book, Insanely Simple, Penn was a featured player in a story I’d heard from a former Microsoft marketer.

So I’ll just end this article by offering up an excerpt from the book. In this chapter, I was talking about branding in general — how Apple expressed its brand perfectly while Microsoft continued to flounder.

The Search for Microsoft’s Values

Just about every company has a mission statement of some sort—an official set of words that describes who it is, what it does, and its reason for existing. Most agencies would consider having this document to be an essential first step toward creating an effective brand campaign.

Yet no one ever bothered to ask Steve for a mission statement before we created the Think different campaign. That’s because he had already given us a briefing from the heart, and even though the company was in serious trouble, its brand essence was well known. If anyone had asked him to hand over such a document, Steve would probably have considered it big-company behavior anyway. We might even have been fortunate enough to see his “rotating turret” in action. [Explained earlier in book.]

Working with Dell was a different story. This was a company that wasn’t very good at describing itself. Had it been able to articulate its brand essence, we could have begun working on a brand campaign immediately. Instead, we had to spend the first few weeks of our brand project figuring out who Dell wanted to be—because who it was at the moment wasn’t working too well.

Microsoft is another company that’s done its share of floundering over the years. Like Dell, it started out setting the world on fire, then somehow lost its direction. It’s still huge and highly profitable, but many of its customers would probably find it difficult to define the Microsoft brand today. While it was once the innovator and setter of standards, Microsoft has lagged behind as revolutions have swept both the smartphone and tablet categories. This sad state is reflected in its stock price, which has been stagnant for over a decade.

Microsoft’s marketing has been spotty for at least as long. Once in a while it manages to strike a chord, then before you know it, it embarrasses itself with something like the “legendary” pairing of Bill Gates and Jerry Seinfeld in a series of TV commercials. Efforts like these fall flat and leave people scratching their heads.

Microsoft didn’t sprout these marketing problems overnight. It’s been battling them for years. A former marketing manager for Microsoft tells a story about a critical time in the company’s past, when new layers of complexity caused it to drift. For the sake of our tale, let’s call him Brian.

When he joined the company, Brian truly loved his job. What he liked most about Microsoft was that “they did things.” That is, the company understood that it was part of a fast-moving industry and didn’t waste valuable time getting hung up on debate. Like Apple, Microsoft understood the value of staying in motion. It was brash too. The executive team knew it could execute faster and smarter than its competitors and considered this one of their great strategic advantages.

Brian loved this aspect of life at Microsoft because it was in such direct contrast to his experience with HP when he worked with its ad agency. He had observed that at HP, process had become more important than progress. “It was all about when the next meeting was going to take place and what kind of muffins might be served with the coffee. There seemed to be more concern about HP than what was going on in its customers’ world,” he said.

It was the Department of Justice investigation of Microsoft that sucked the life out of the company over a two-year period starting in 1999. Fearful that it might run afoul of government investigators, the company became listless in its marketing efforts, with no clear direction forward.

After Attorney General Janet Reno took Microsoft to court, Bob Herbold, then Microsoft’s COO, called a meeting of the minds to calm people down and get everybody on the same page.

The attendee list was a who’s who of Microsoft communications, including the company’s chief counsel and its head of PR. At one point, an executive with responsibilities in community affairs stood up to speak her mind. She painted a picture of a great company unfairly tarnished by the press. Microsoft was doing many good things in this world, she said, and the government simply didn’t appreciate this. The situation was frustrating to all of those who believed in the goodness of Microsoft and the value this company brought to the world.

Her speech built to a crescendo. “They think we’re up to no good,” she said. “They don’t realize that Microsoft is about positive things. We need to help them understand what our values are.”

She paused briefly, allowing that thought to resonate in the room. Then she looked straight at the communications team and said: “What are our values? Are they written somewhere? Does anyone have them?”

In other words, the way forward was for Microsoft to express its values to the world—but even as a Microsoft executive, she wasn’t aware of what those values might be. There was no magic document hidden on anyone’s computer either. The company’s values had never been codified.

From that point, it took Microsoft eighteen months to study itself, crystallize its values and decide what it stood for.

It might have been because of the DOJ legal action, or it might have been because of Microsoft’s inability to maintain its focus—whatever the cause, Microsoft had devolved. It had changed from a company that moved at light speed to a corporate behemoth that had somehow lost the ability to turn words into action.

It was a frustrating time for Brian and his team. But things were looking up for complexity, which saw its opening and went for it.

Suddenly lacking confidence in Microsoft’s internal marketing team, Steve Ballmer looked outside the company to meet this marketing challenge. He turned to polling expert Mark Penn in Washington DC to develop a positioning that would counter the growing public image of Microsoft as a dangerous monopoly. Penn was given the authority to develop a softer image for Microsoft and directed the marketing team to move in a whole new direction: The Microsoft brand would be about “kids, puppies and small businesses.”

Inaccurate as the image was, it did follow a certain logic. If Microsoft wished to be seen as a softer, friendlier company, Penn knew that kids and puppies were slam dunks. A new emphasis on small business would logically counter Microsoft’s image as a dark, dominating force.

Brian’s marketing team was stunned. As far as they could tell, they didn’t have the stories to support the new positioning. Small business, yes. But kids and puppies, no. The closest thing they had to a youth story was Microsoft’s K–12 education software marketing program, which represented only a tiny fraction of Microsoft’s market. Brian was responsible for the messaging to all of Microsoft’s customers, and the warm/fuzzy approach seemed terribly out of place. However, the marketing group had now been expanded by one—an outsider whose expertise was not in marketing—and things would never be simple again.

Brian’s experience continued to spiral. He found himself having to represent ideas he didn’t believe in, which, as we know, is a gross violation of the principles of simplicity. Brian found himself presenting Microsoft’s new kids-and-puppies brand to a meeting of DC lobbyists summoned to Microsoft’s headquarters. It was an all-star cast of extremists on both sides of the political spectrum, including Ralph Reed from the Christian Coalition and Victor Fazio from the left. Under pressure, Microsoft was forced to become an “equal opportunity” kind of company, offending no one. Brian was dispatched to stand up and say, “Here are our new technologies, here’s why they’re good for America, here’s how we’re communicating our ideas to everyone.”

When he left that meeting, Brian felt lost. He actually called his dad to say, “I feel like I’m working for a tobacco company.” He didn’t feel good about himself or his situation.

It’s always shocking to learn that a company as successful or influential as Microsoft or Dell can run into trouble trying to define itself. But that’s the kind of confusion that results when big organizations get bigger—and people lose sight of what makes things simple.

[Reprinted from Insanely Simple: The Obsession That Drives Apple's Success by Ken Segall.]

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Justin Bieber: When Is Enough Enough?

By Sa'iyda Shabazz


Since he burst onto the scene in 2010, Justin Bieber has been everywhere. With millions and millions of Twitter followers to match his millions and millions of dollars, it is no wonder why he has become a mega star all before his 18th birthday. Now, having just turned twenty, at the beginning of this month, it seems that his star may be slipping…just a little.

From the start of 2014, it seems that every time Bieber is in the news it’s not because he’s promoting his latest single; it’s because he’s getting in trouble with the law. Several times have been because of drugs (mostly marijuana) but also vandalism, assault and resisting arrest without violence. All of this has led to a major backlash, even calling to deport him. Granted, Bieber has always been a polarizing figure in pop music, but it seems that now it is only getting worse. This newfound bad boy image begs the question, how long will it be tolerated? And if he was another artist, would he be treated differently?

Because he is marketed to a teen market (his fans call themselves ‘Beliebers’), would taking a stronger stance against his behavior be a detriment to the music industry? Even though he hasn’t released an album since 2012, he’s still a multi-million album seller. It would seem that even with his spurt of bad behavior he’s still doing the entertainment industry a favor. Tabloids know that even featuring a one page write up on him will cause his fans to buy a copy, but putting his face on the cover? That’s almost priceless. The more he keeps his name in the news, the better it is for everyone’s pockets.

One could also argue that this is all due to growing pains. When he first came to the US, Bieber was a 15 year old kid with a goofy haircut. Now, he’s on the verge of adulthood. Could all of this bad behavior just be him stretching his wings and testing his limits? Things like egging your neighbor’s house and drag racing your car are not unique to him but the consequences could be worse because people know that they can make an example of him. Like most boys his age, as he becomes a man he will be tested.

But what he seems to fail to understand is that because he is in the public eye, his actions are made into case study. Can he really afford to be reckless? Most people would say no. Because he is a teen idol, he has a responsibility to his younger fans to behave like a mature adult. But most of the girls to whom he is considered a God don’t care about his actions. In fact they are defiant and more than willing to defend him to the death. Their loyalty is unyielding. If you post a tweet saying anything negative about him, beware, there’s a good chance that there are young Beliebers trolling and they will have something to say. It is unknown how he has brainwashed these girls into wanting to be a part of his breaking the rules but it is a true testament to his popularity.

To me, it is interesting though that the only fans of his who can see that maybe he isn’t the best role model seem to be under the age of 13! There are a few little girls in my life who realize that maybe Justin Bieber isn’t exactly the best person to look up to. Just the other day while showing me her oft-played with Bieber doll, my friend’s 8 year old daughter told me that now she “just likes his music,” citing him as not so much a good guy anymore.

Another friend’s young daughter made her mom buy her a new backpack for school because she felt that she was perpetuating the wrong message with Bieber on her back. It is hard to say why these little girls seem so much smarter than girls who are probably 10 years older than them but at least someone is using their brains! It is hard to say how much longer this behavior will continue, especially since he still has another year before he is 21, but maybe he should take some time off and reflect on his actions. Not just how they’re affecting those who look up to him but how they are affecting him. Is this something that he’s going to be proud of when his kids Google him in 20 years? Probably not. Of course you can chock it up to childhood foolishness but it’s time to stop.

Go make a music record, not a prison record.

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Countdown to Oscars
The Shorts

By Nathan Edmondson

For the week leading up to the 86th Academy Awards, the Academy of Motion Picture Arts and Sciences is hosting Oscar Week, a series of public events honoring this year’s nominees.  On Tuesday night, I had the privilege of attending the sold-out Animated and Live Action Short Film Program at the Samuel Goldwyn Theater in Beverly Hills. The ten films screened over the nearly four hour event are each a testament to the artistic excellence possible with the short film format.


Wait. It took four hours to watch the short film nominees? Yes.  Andyes, that’s a long time to be sitting in a theater seat. Required to be no more than 40 minutes in length to qualify for the short film categories, most of the nominees fell into the 10 to 20 minute range. Thankfully, host and stand-up comic Kevin Pollack kept the night and the Director Q&A’s rolling, and a ten minute intermission to stretch and run to the corner store for ice cream helped as well.  And did I mention all the films were excellent?

The night consisted of five animated and five live action films from around the world. In fact, only one of the films was produced in the US, the Disney animation short ‘Get a Horse!’ (Many foreign films benefit from direct government funding and support.) Of the animated films, ‘Get a Horse’ set a high technical bar interweaving the animation style of the earliest Mickey Mouse cartoons with modern 3D animation. Yet, I see ‘Mr. Hublot,’ about an OCD mechanical man and his mechanical dog, or ‘Room on the Broom,’ based on a popular children’s story about a good witch and a whole mess of animals, as the front runners in the animation category for mere emotional engagement and elicitation of joy.

All of the live action short films were powerful. From the violent and war-torn ‘Aquel No Era Yo’ (That Wasn’t Me) about child soldiers in Africa to the playful and fun ‘The Voorman Problem’ about a man who believes he’s God, the stories told were equally varied and engaging.  ‘Avant Que De Tout Perdre’ (Just before losing Everything) is a masterful story of suspense; yet, the sweet and tender ‘Helium’ remains my favorite for the live action short film winner.

Kim Magnusson, ‘Helium’ producer, three time Oscar nominee and one time Oscar winner, pointed out that his company uses the short format to groom up-and- coming talent. He went on to articulate that, in fact, the short form is most effective because it doesn’t have the industry pressures that accompany producing a feature film. As a result, all of the attention can be put on being true to the story and to the short format. Based on the quality of the nominees’ work, I’m sure we’ll be seeing many of these directors in the future.

To find out more information about this year’s short film nominees, please visit  I hope you are able to catch some of these wonderful films, before or after Sunday’s big event.  Having suffered from limited distribution in the past, short films are gaining in popularity thanks in large part to the internet and VOD.

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The Ultimate Screenwriting Tips
From InkTip Founder Jerrol LeBaron

By Eric Weintraub

JerrolHOI600x800-2Jerrol LeBaron is the founder of InkTip, an online service that helps screenwriters connect with producers with the intent of making a film together. Since the company began in 2000, filmmakers have produced over two hundred feature length films, (last year alone thirty-eight films were shot), and dozens of screenwriters have gained representation. Jerrol has also produced a number of his own films. I was interested in the man behind the company, how Jerrol came to form InkTip and how he pursues his own independent projects. We sat down to discuss his life’s work and his passions.


InkTip started as a company called Writer’s Script Network. Jerrol conceived the company as a way for screenwriters to post their screenplays online so prospective producers would have an easy way to access content. He had written his own screenplay and had a difficult time getting it read. He felt more screenwriters would have a chance at success if they had an easier way connecting with the producers. He discovered another company working under a similar name, so he switched the name to InkTip and hasn't looked back.



For Jerrol what makes a good script is simply that it reads well. You sit down, you get in, you get out. There’s no fat. Bad scripts, for him, plod along. However he did recognize this as a matter of taste. He knew there were many people out there who might find the beauty in a slower paced story. Jerrol references westerns and sci-fi films as his favorite films, citing Tombstone and Blade Runner from each respective genre.


Neither Jerrol nor his employees ever read an InkTip script. They've helped get so many movies produced because they don't bring a bias to the material. They allow the producers to judge the scripts based on their own needs and tastes. InkTip requires writers to fill out a questionnaire and a short synopsis when they post their script, which helps producers discover their dream project.

Jerrol cited an example that underscored why he felt his method worked. A few years ago, a producer friend urged him to take a script off his site, feeling it wasn’t up to the site’s standard and “was ruining the credibility of his company.” Jerrol did not take the script down and a few days later, an agent read the same script and offered the writer representation. It goes to show that one man’s Razzie is another man’s Oscar.


Jerrol says that having a good screenplay is important, but it isn’t enough. You must be able to work with people. He explained that even if a screenplay might be perfect, the writer must still understand that changes may be made down the road. For example, if a screenwriter gets his $300 million space opera produced, and the studio needs him to write in a scene that appeals to foreign markets, he must collaborate with them to make the scene work in the film.


Jerrol’s move into producing his own projects did not stem from the success of his clients, but from his own passion to communicate as a social activist. As an activist, he realized a lot of people weren’t pleased with their politicians and he wanted to make a movie about it. He made the documentary Fools on the Hill to discuss this problem. The film follows one man’s attempt to require politicians to read the bills they passed, a law not currently required in the U.S. He hired Jed Rigney, one of his star writers at InkTip to come on as the film’s writer/director. He knew Jed would be the right person to film the material.



Next, Jerrol got involved with a comedic film called Nowhere Girl. This film was a passion project of Jed Rigney’s. After the completion of Fools on the Hill, Jed told Jerrol about the script: the story of a broken hearted boy who meets a girl that turns his life around. Jerrol knew people who would invest money in the film. He pulled the funds together and helped Jed realize his vision.



Jerrol wants to further innovate InkTip. Up till now, writers have sent off their screenplays to producers and not heard word for weeks or months. To make the screenwriter not feel like they’re throwing their labor of love into a black hole, he now wants to install a tracking system for InkTip writers. The tracking system would let writers know how far into their script a particular producer got. If they log on and see a producer read 15 pages six weeks ago and never picked it up again, they can assume the rejection and not waste time. However, if they realize their script has sat by the wayside, it would give them the proper excuse to contact the producer and give them a friendly reminder.

Jerrol LeBaron is an entrepreneurial man with an innovative vision. He is not only a champion for film, but for finding new ways to help aspiring screenwriters, and for using his own talent to make powerful documentaries that ask for social reform.

For more information about InkTip or how to submit your script, visit their website here.

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From SNL To The Brothers Of Late Night:
Jimmy Fallon & Seth Meyers - First Impressions

By Andy Greene

Jimmy Fallon  Seth Meyers

After a long and turbulent process that we all grew tired of, it appears that NBC has finally found its heirs for the Tonight Show and Late Night for the foreseeable future. Thankfully, we can wipe our hands of Conan O’Brien, Jay Leno and the various feuds, and focus on the late night shows themselves, their content, and cheer for two of the nicest guys in entertainment.

The process was ugly, but moving on never is, and I think NBC has found two keepers of their respective desk and couches, until the next Saturday Night Live alums come to take their jobs in 2023. When Jimmy Fallon was chosen to take over for Conan on Late Night, it was met with much skepticism. He hadn’t succeeded at anything since leaving SNL, and didn’t seem as funny as some of the other alums. But his amiable, honest, goofball nature proved a perfect fit, and his immense talents had been severely underrated. Guests wanted to have fun with Jimmy Fallon, and so did his audience.

It appears like viewers are in for more of the same with his stunningly smooth transition into the Tonight Show. It’s essentially Late Night an hour earlier, as Fallon (of course) brought the best band of late night, Questlove and the Roots, along for the ride, and even counted on his most reliable and popular skits to buoy his promotion. Nabbing Will Smith, Bradley Cooper, Will Ferrell, Kristen Wiig and musical guests like U2 and Lady Gaga on your show is one thing, but making them more than just a promotional tool is entirely different.

He didn’t waste their time. Will Smith gamely and ably joined in on the Evolution of Hip-Hop Dancing (succeeding Mom, Dad and End Zone Dancing), killing it in the process.

“Celebrity Charades!” needs to happen every night, if only to revel in how bad celebrities are at that game. While Emma Thompson was a champion, Tim McGraw couldn’t even count the number of words in The Wolf of Wall Street and Bradley Cooper couldn’t do much of anything, bliss for this viewer. Will Ferrell bizarrely dressed up as a butler from Downton Abbey and “skated” for a few minutes. Kristen Wiig arrived as Harry Styles of One Direction for no apparent reason, but it hardly mattered. They turned Brian Williams into a YouTube sensation. It was weird, interesting, and Fallon carried us through it all. Except when Justin Timberlake arrived to share the load, ready to embark on “The History of Rap 5,” and as always, KILLING it. Fallon produced a stunning number of viral videos in just his first week. While it’s an unsustainable pace, it’s clear his producers know what’s working, and will stick with it. Aside from a more posh time slot, the differences between Late Night and Tonight Show practically begin and end with the first word in their titles, and thankfully, Fallon and his team get that.

Jimmy Fallon and Seth Meyers have enough parallels (nice, honest, white, SNL background, known quantity), where it’s obvious that NBC simply chose Seth Meyers because he reminded them of Jimmy, an (at the time) ho-hum hire that became a phenomenal success. It’s no wonder Seth Meyers spent his cold open thanking Jimmy Fallon personally, because it was Fallon who got him this gig.

But it certainly appears Seth Meyers is up for the task, following his first night. There are certainly wrinkles to iron out, but Meyers was able to weather the storm of poor jokes (aren’t we all tired of Sochi jokes by this point?), or ones that didn’t sell as much as he had anticipated. I could’ve done without him spelling out jokes that didn’t land or get a big enough laugh, but Meyers also never bothered me. He’ll improve at the monologues, but after a decade on SNL co-hosting Weekend Update, he was at home in the chair, chatting it up with his guests.

It certainly helped that his first guest was Weekend Update running mate and bestie Amy Poehler (Parks and Recreation, The Golden Globes), providing a nice soft landing for Meyers. She even practiced at being a bad or boring guest for practice (“I just wanna say something racist”), and somehow managed to be funny and supportive at the same time, while also creating imaginary tiffs with the band.

That band would be Fred Armisen and the 8G Band, who are the perfect musical accompaniment. Of course, the band itself hardly ever matters; anyone can do drumrolls and dorky sound effects. It’s their personality and chemistry with the host that people latch onto, and Fred Armisen, another SNL veteran and friend of Seth Meyers, clearly has overflowing amounts of just that with the host.

NBC didn’t mess around in their first week, as the guest list implied. They snared Michelle Obama for Jimmy Fallon, and secured Vice President Joe Biden in Seth Meyers’ FIRST SHOW ever. If Meyers was nervous, he didn’t show it, though Poehler’s presence and chemistry with the Parks & Recreation guest star certainly made it easy. Nothing stood out and made me take notice in Meyers’ debut, but there were enough promising signs to be optimistic going forward, and that is also found in the ratings.

At least thus far, both moves seem like a win for NBC, which has been quite the rarity over the years. The Late Night show’s premiere debuted to 3.4 million viewers and a 1.4 rating in the ever-important 18-49 year old demographic, the best Monday Late Night since January 2005. Seth Meyers’ debut even outdid Jimmy Fallon’s Late Night debut, by 500,000 people. At this rate next year, Seth Meyers will be gunning for his job on the Tonight Show. Jimmy Fallon rode a wave of Sochi Olympics coverage into 8.5 million average viewers over his first week replacing Jay Leno, and kept the good thing going in his second week, retaining 6.26 million viewers, and achieving a 2.1 rating in the 18-49 range for a Monday show. This kind of success is nice to see, as NBC’s loyalty and shepherding of its own talent is paid off, by rewarding and adopting valuable players of Saturday Night Live and grooming them into being America’s companions before going to bed.

Like Fallon, Seth Meyers isn’t the most dynamic funnyman there is, but they are two of the most genuine, nice, likable people in a world that needs that comforting presence. I think, with time, Seth Meyers and his team of writers will push the envelope a bit more (it was a very safe first show in terms of bits and sketches; I mean, Venn Diagrams?), and feel their own way into making Late Night Seth Meyer’s own.



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