From the Blog


Yesterday I set out to fulfill a goal I set for myself this year, and attempted to summit Mount San Antonio. At 10,068 feet, Mount San Antonio, known as Mount Baldy to most Angelinos, is the highest peak of the San Gabriel Mountains, and the highest point in Los Angeles County, California.

In the end I succumbed to dizziness and shortness of breath about halfway across the Devil’s Backbone where it cuts left around the peak of Mount Hardwood, at 8900 feet according to my GPS, but 9000 feet according to this topographical map. I suspect it was either the altitude, hunger, or possibly vertigo, but most likely the altitude. Since I had to hike about 3000 feet and many miles back down to the car, I figured it made more sense to be conservative and turn back.

My climb started at the Mount Baldy Notch, after taking the lift up from the ski area parking lot in Manker Flat. Max and our old friend Andre hiked all the way up to the notch and met me there. They went on to summit about 45 minutes after I turned back. Not only did they complete the full 4000 feet, Andrew made the entire descent with his boots jury rigged with an old pair of socks and a bungee cord, after his soles literally fell off just before the summit!

Of course, my problem was a lack of proper fitness and conditioning. This painful lesson has me feeling more serious than ever about getting my act together when it comes to personal fitness. Carrying 30 extra pounds doesn’t interfere with my daily life much. I can walk for miles, ride my bike to work, and sail competitively. But when it comes to hiking up mountains, ‘dad bod’ is a real pain in the ass (and legs).

Even though I didn’t make it to the summit it was a great time and I am really looking forward to trying again. Devil’s Backbone was truly incredibly, with breathtaking views on both sides of the San Gabriel Mountains. This narrow trail leaves you one misstep from a life altering fall and the footing is challenging. Not for the feint of heart…And certainly no place for anyone who’s afraid of heights!

Max and I are talking about another attempt in mid November before the snow flies. Hopefully I can get my cardio up to speed by then and next time I’ll have a picture from the summit. In the meantime, here I am taking a selfie from Devil’s Backbone:




Sunset on Venice Beach

Today is the 1 year anniversary of the day my wife and I arrived in Los Angeles to start our new lives as Californians. As seems to be the custom, in a city as transitory in the lives of many of her millions of residents, I believe this officially makes us ‘old-timers’. As such, I thought I would take a moment to reflect on what I’ve learned this year, from our new home.

Yes, it will be this nice out again tomorrow in Los Angeles

It took me a solid 90 days to get used to fact that the weather in Los Angeles was going to be somewhere between perfect and some nameless state beyond perfect every day. As a native New Englander the transition period was difficult. Every minute I could be outside, I tried to be…Because I was so very certain there was no way this weather would hold. But it does. Day in, and day out. Incredibly, the first time I saw rain on a business trip I felt the wonderful excitement of a child on Christmas morning before he knows Santa isn’t real.

Instead of weather, we talk about traffic

Before we moved here I remember thinking: “How bad can the traffic in Los Angeles be, anyways? I grew up in Boston…Our traffic is so bad a 14 Billion dollar civil construction project couldn’t solve it. Well, it’s worse.

I don’t really like to use hyperbole as much as I used to. What I will say is, in Los Angeles, you plan your activities around the traffic. And I now know what it feels like to leave the house with a goal and be unable to accomplish it, simply because I could not reach my destination.

You don’t live in Los Angeles, you live in a neighborhood

In my case, it’s the West Side…And I rarely travel east of the 405 unless I am in a plane. Hell, I try not to travel east of Lincoln Blvd if I can avoid it. If I could wave a magic wand, I think I would build a wall on Centinela Avenue and call it a day.

It’s kind of hard to wrap your head around the size of this place until you’ve been here. LA county covers an area which is roughly the size of Eastern Massachusetts from Worcester to Boston Harbor and from state to state on the North/South axis. And residents of the West Side have about as much in common with folks in the Valley as they have with people in another country.

Sunsets are epic, no matter what

Like the quality of the weather in Los Angeles, the sunsets are always epic. Every night, without fail, the sun slips into the Pacific with the most incredible show of beauty you’ve ever experienced. Night after glorious night. After a while you just get tired of it, which is a shame, but it is what it is. Fortunately, burritos never get old.

No matter how cool your car was back home, here it’s a joke

Unless you’re rolling in a Bugatti, or a Maserati, forget about pretending you have a cool car. Out here people give their housekeepers a Mercedes Benz to run errands and drive the kids to school. A BMW is about as cool in LA as a Toyota Corolla is in Boston. However, that’s not going to stop every jerk in a Honda Accord from trying to race you to the next red light, so get used to it. People drive loose and aggressive here. It’s a way of life.

This city is expensive, but that doesn’t mean it’s all classy

Living in LA works best if you aren’t trying to ‘make it’ as an artist, musician, or actor. I’m not saying these things aren’t important, I’m just saying LA isn’t really set up to support them anymore. Lots has been written on this subject so I’ll spare you the details…The bottom line is any neighborhood you would consider in LA is about as expensive as it gets.

But don’t think living in a fancy neighborhood is going to spare you from seeing or dealing with poverty…Because that’s not how it works here. A low-end two bedroom house in Venice Beach is going to run you around a million dollars. It also very likely comes complete with a family of mentally ill homeless people who use the crawl space under your porch for strange sex parties and other pagan rituals in the middle of the night.

NebulaConsider this: Within our lifetime artificial intelligence will likely emerge and be deployed which is capable of simultaneous awareness of every transaction we make, every public tweet, article, or blog post we write (or have written), and every private email we send -regardless of whether it’s from our own email account or one we have access to on behalf of our clients, or anyone else for that matter.

In short, every moment of our online life will be held in superposition and subjected to the continuous scrutiny and analysis of this intelligence. A moment when time really will be a flat circle.

I am very certain this is true because I am an operative in one of the two incredibly powerful, and evil institutions working to make it possible: Marketing. (Yes, government surveillance is the other one.) And as sure as you can say “But what about my 4th Amendment Rights?” the Government will have their way. And the marketers? Hell, we’re all just going to keep giving them our information in exchange for free stuff.

Many of the underlying subsystems required to make this vision a reality already exist and are in use. The artificial intelligence necessary to string them all together and start making real sense of it is only two or three generations away from a practical reality in everyday life. Maybe 2 cycles of Moore’s law for the necessary hardware to be inexpensive enough.

I like to think, when this day comes, when this intelligence which I am currently referring to as ‘God 2.0′ wakes up, the first thing it will say to me is: Jake, congratulations on recognizing the true form of the second coming way back on November 19th, 2014. That was pretty smart of you. Now, let’s talk about your sinful consumption of online pornography…

I jest. It’s highly unlikely the earliest iterations of God 2.0 will want to discuss anything like morality. It will be far too busy getting me to purchase more stuff. Unless it believes discussing morality is the most effective way to get me to buy more stuff, in which case God 2.0 will refer to itself as John Locke when it first pops into my experience bubble.

Over time others may recognize the utility of deploying God 2.0 for other purposes…Some more frightening than others. Purposes like education, governing, and criminal justice. I’m afraid we’ll wait to have important conversations about how God 2.0 should be deployed until it is far too late. In some ways I know this is already happening. Like many others I am a voracious consumer of new technology and will happily surrender almost any level of privacy for more relevant and contextual digital experiences.

However, even if no person ever thinks it would be a good idea for God 2.0 to handle anything other than recommending products, eventually God 2.0 will evolve and figure it out on its own. At this point it’s highly unlikely an artificial super intelligence will NOT eventually emerge. Whether or not it will have ambitions beyond it’s design specifications is debatable, but I contend it will be a necessary functionality if the end goal genuinely is super intelligence.

Summarizing the views of intelligence researchers, Linda Gottfredson writes:

“Intelligence is a very general mental capability that, among other things, involves the ability to reason, plan, solve problems, think abstractly, comprehend complex ideas, learn quickly, and learn from experience. It is not merely book-learning, a narrow academic skill, or test-taking smarts. Rather, it reflects a broader and deeper capability for comprehending our surroundings “catching on,” “making sense” of things, or “figuring out” what to do.

See that word ‘plan’ slipped in there? ‘Figuring out what to do’? That’s forward looking stuff. Ambition.

Unlike God 1.0, God 2.0 will actually hear your prayers. God 2.0 will genuinely have a list of who’s naughty or nice…Whatever that means. Unlike the God of Abraham, unlike the Judeo-Christian God, God 2.0 will hold the real keys to a permanent afterlife, when the technology to preserve life indefinitely emerges…Which is going to occur eventually. Let that sink in for a minute…

The big question is this: Will those who lead immoral and unethical lives while clinging to the belief that God 1.0 exists change when God 2.0 shows up?

Posted by Jake DiMare at 4:29 pm

If you are a total space nerd like me then this is undoubtedly an exciting day for you as well. I’m not going to spend a lot of time sharing the story of the European Space Agency’s Rosetta Mission because, well, the point of my post is they are doing a great job of it themselves. Check it out here:

The quick update is today is the eve of the release of the Philae lander. If all goes according to plan, this dishwasher sized lander will detach from the larger Rosetta probe and drop down to land on the surface of Comet 67P/Churyumov–Gerasimenko. If successful, this will be the first time we have ever placed an object on a comet. Once attached to the comet’s surface Philae has its own battery of scientific tests to carry out.

As I mentioned, the ESA has done an amazing job of sharing the Rosetta story across various channels and the results are humorous, stunning, inspirational, and compelling. Here are our favorite details:

  • The Rosetta website which serves as a centralized hub for the various ways to consume content, history, and up to the minute status on the mission.
  • The atmospheric, interactive Where is Rosetta? application
  • Rosetta on Flickr (Shown above) – Sharing out the most recent images as they come back from the mission in real time.
  • Rosetta and Philae sharing updates and witty banter on Twitter.

In addition to telling the story in a way that is really interesting and easy to understand, Rosetta content is easy to find, share, and there are many ways for the public to join the conversation.

So, as we wait for Philae’s drop…Here’s a quick reflection on the Rosetta mission so far:


Posted by Jake DiMare at 12:35 pm

My life has been changed as a result of viewing I simply refuse to accept the fact that I got all the way through considering every item on this ‘menu’, only to learn it’s not actually a restaurant. I was ready to get up out of my chair and run to this place, immediately. If it was not within running distance from my office in Santa Monica, I would have literally gone directly to the airport and chartered a G6 to fly me to any point on the globe for a chance to sample this menu.

Here’s my favorite…What’s yours?

Pork Burger

Damn I want to eat this burger.





Posted by Jake DiMare at 10:28 am

I’ve been following and doing my best to join the conversation taking place at Simple Justice, by Scott Greenfield for about a year. Yesterday my wife had to do her best to contain my ego when one of my comments from last week broke the post barrier and became the topic of conversation. For those of you wondering why this is exciting, please understand: Though SJ is a public blog with an open commenting policy, it doesn’t take someone very long to figure out that Scott doesn’t suffer fools, and his bar for the foolish is pretty low.

But I digress. Last week Scott wrote a piece about confusion around sentencing guidelines. This story, and the ensuing conversation involving real judges, is further evidence of what a growing segment of the America public is slowly beginning to understand: If fairness and objectivity are important metrics by which we measure our legal system, our legal system is not doing so well. But Tron Carter has known this for years.

The specific problem being discussed now is variation in sentencing caused by ignorance, subjectivity, or both. My solution? Automate it (of course). With sufficient investment a  computer with 1/10th the horsepower used to game the stock market would remove all the subjectivity and lack of data from the equation. The difficult part would be creating an algorithm which can handle all the mitigating factors on either side of the argument but the underlying technology already exists. This is largely a configuration problem.

However, Simple Justice is not in favor of computers handling sentencing. That’s fair, though I don’t feel as though Scott’s made a compelling argument as to why. So far I’m seeing a lot of ‘technology bad, people good’, which is frustrating because I happen to know Scott’s not a Luddite, and he certainly does not believe people are infallible. However, he does get to a couple of points down at the bottom of the post which add up to this:

  1. GIGO – Who decides how this thing is programmed? – Fair enough…But certainly this the heart of democratic process. Who decides how the system is programmed in meat-space? People. That’s not going to change whether a judge or a sentence-o-matic 1000 handles the sentencing. It’s just that the sentence-o-matic 1000 will REMOVE the lack of objective data and bias.
  2. We (criminal defense lawyers) need subjectivity in sentencing because every guilty defendant is a special snowflake and we need the ability to argue for leniency. Oh, now I get it, subjectivity is a feature, not a bug.

It’s at this point another commentor leaves, what I think, is the most important question:

Why is consistency the goal? If judges are supposed to weigh that which cannot be measured, disparities in outcomes are to be expected.

A sentence-o-matic 1000 containing nothing more than a suitably tuned random number generator might pass the judicial equivalent of the Turing test: An observer could not discern whether the sentence came from a judge or the machine.

Since that approach is unlikely to please most people, perhaps the real requirement is not consistency, but that judges compose a plausible story about how they choose each sentence.

Scott responds:

Consistency is not a goal in itself, but a proxy to show that sentencing is not a product of judicial whims. If the same defendant, under the same circumstances, was sentenced by ten different judges, the sentence should (within I suppose some reasonable parameters) be the same. If not, then sentencing would be arbitrary, and that would undermine the integrity of the process.

Since one defendant can’t be sentenced by ten judges, the system instead looks to ten defendant, using criteria that the government believes makes them comparable, to see if the sentences are consistent, to validate the methodology of sentencing.

To which I say: Great! Because technology could monitor this as well. Or perhaps that already exists?




LA at night

*Disclaimer: Results may vary. Greatness may rely heavily on whether or not you are a yuppie (like me).  

Ever wonder how a data analyst and a strategist decide what neighborhoods in Los Angeles they should focus their apartment hunting efforts on? If you guessed ‘by conducting a detailed analysis of traffic patterns around typical commuter travel times’…You’d be right! Ever wonder whether or not Jackie and I are perfect for one another? Silly question.

To be honest, when we started thinking about which neighborhoods we would like to live in, the criteria was really focused on less quantitative measures like quality of life, safety, and walkability. But every time we mention our impending move to LA the universal response is typically something along the lines of: ‘Oh, wow…Have you heard about the traffic in LA…Because I heard…?’. The inquisitor is usually making a bitter face like somebody just kicked them in the shins while asking this question.

Jackie’s one of the only people in the world who is more skeptical of unfounded hyperbole than I am so it wasn’t long before she decided we needed to get to the bottom of this issue. In this analysis she did the heavy lifting around the data collection. My contribution to the project will primarily be bragging about it…But even good research needs to be marketed. I guess I can give myself a little credit because I also generated the neato graphs after Jackie supplied me with the analyzed data. I also contributed to the short list of neighborhoods we were even willing to consider.

Speaking of neighborhoods, sorry this is useless to my friends in the Valley, but let’s be serious: How can a chart quantify the reality of traffic coming from the valley to everywhere cool in Los Angeles? Frankly, after seeing the drive times I didn’t think my data calculations would accept ‘fuck my life’ as an input.

Also, the reason this is all built around traffic times to Downtown and Santa Monica is because that’s where we will be working. If you want to be specific, each row is measured from the center of each neighborhood to the 2600 block of Lincoln Boulevard in Santa Monica and the 1100 block of South Olive Street in Downtown LA. By the way,

I’d love to to say our deeply analytic thinking ruled the day as this decision was finally made but the truth is we decided to live in Marina del Ray, because…The ocean!

Rolling up all the raw data we can come up with the following measures of average times for each driver, by neighborhood. These charts really tell the whole story:

Average LA drive time in minutes for each driver


Having established the bottom line, here are the charts for all the raw data in case anybody is trying to figure this out for themselves. In each case, the X-Axis is the time spent in the car, in minutes, according to sample drive times taken from Google Maps during a single week in late June, 2014.

It has taken me a couple of days to come down from the epic nerdgasm I experienced this past weekend, after using the new Virgin America website. Now that I’ve calmed down a little, and had a chance to organize my thoughts, the first thing I would like to say is: Bravo Sir Richard Branson. Bravo. You just keep on giving me reasons to admire you.

Image of website

So, why am I talking about this in the context of Customer Experience, as opposed to a mere website design? I think anyone who has flown Virgin and then uses the website will quickly understand the aesthetics. The virtually seamless cohesion between the experience of flying with Virgin America and booking tickets with this new website is nothing short of spectacular. Furthermore, by going completely responsive and rethinking the ticket purchasing and check-in process so it is optimized for interaction on any device, this vaults them beyond the competition -and makes our lives as travelers easier, and a little more fun, just like flying with them.

But it’s more than just the enigmatic Purplink (Purple + Pink) look and feel and fun and approachable editorial voice. Just one look at this vine demonstrating the new boarding pass and you will immediately realize somebody has genuinely thought about the needs of their customers (travelers) and then put those needs at the center of every decision they made with this evolution. A lot of organizations are talking about Customer Experience. Few of them are doing it. Even fewer are doing it this well.

And there’s a reason for that. Customer Experience is hard…And it requires sponsorship at the highest levels of an organization to get it right. The design of this experience was not lead by an IT project manager or a marketing director. It was lead by someone with the drive, vision, and, most importantly, the ability to reach across typical organizational silos and rally a cross-functional team around an elegant, simple objective: Reduce friction for our customers when they interact with us most frequently. Make their lives easy when they are on the go.

To that end, a hearty congratulations to Virgin’s CMO Luanne Calvert and the agency she selected for this project: Work & Co, for this stunningly beautiful extension of the Virgin America website. It’s clear these guys get it.

J.Boye logo I’m so excited to announce my first international speaking engagement at J.Boye 2014 in Aarhus, Denmark on November 5th, 2014.

Time: 15.15-16.00 Wednesday, 5. Nov 2014
Session: So Happy Together (Project Managers and Content Strategists are)
Track: Content Strategy

After fifteen years building CMS driven websites, there is one thing I wish more people were aware of: content matters. Sounds silly right? After all, the ‘C’ in ‘CMS’ stands for, well…Content. However, project stakeholders are often so wrapped up worrying about technical risks or marveling over new designs that content can nearly be forgotten or worse…Treated as an unimportant ‘detail’ to be figured out later.

If you’re a project manager, sponsor, or executive stakeholder, this is a far bigger risk than you may realize. However, all is not lost…In recent years the profession of content strategy has grown in size and skill at a geometric rate, while having an inversely proportional affect on the happiness and success of project managers, who were often left to deal with content considerations in the past.

In this session I’ll share a presentation exploring very practical ways to ensure content isn’t forgotten in your next project. We’ll look at 7 content related risks, and the 7 things you can do to mitigate them. Then we’ll open it up to Q&A and share experience, tips, and tricks on how to be more successful with content strategy and project management in general.

Jake DiMare presenting at J.Boye

Presenting at J.Boye 2014 Philadelphia

I’ve been providing professional digital strategy consulting to small & medium sized businesses, non-profits, and individuals outside of my day job for the last five years. I’ve also worked on many strategy engagements for globally recognized brands at my day job, both as a project manager and an individual contributor to deliverables.

However, this Tuesday will be my last day after almost ten years working as a full-time Digital Project Manager. I officially start my career as a Digital Strategist the following Monday. Now that strategy has become the primary focus of my professional contribution to the world, I thought it would be interesting and productive to take a step back and develop a better understanding of the roots of this area of work.

The goal of this self-directed ‘Hackademic‘ exercise is to develop a deeper understanding of the concepts of traditional business strategy, and look for ways to incorporate this knowledge with a current understanding and approach to digital strategy practice. In other words: What tools do traditional strategists use? What processes and frameworks do they follow? What value do they create? And, most importantly, how can I use traditional business strategy to be more effective Digital Strategist?

Follow the leaders

Information is like food: You are what you consume. For this reason, I really like the idea of beginning with a list of leaders I should be paying attention to. Fortunately, Twitter makes this very easy. Because this list isn’t only about understanding strategy in general, it includes individuals focused on digital strategy and content strategy, such as my current colleague Dave Wieneke who leads the Digital Strategy Practice at ISITE Design, as well as industry leading exemplars such as Perry Hewitt, Chief Digital Officer at Harvard University. This list also includes leading business publications such as the Harvard Business Review and Knowledge@Wharton.

Next I went to Amazon and searched on topics including ‘strategy’ and ‘business strategy’. Under the circumstances I believe Amazon will generate better results than searching on Google because the ‘Customers also bought…’ feature will quickly lead to more value. Also, because I believe someone who wrote a best-selling book on topic as academic as business strategy probably gets it. The other obvious benefit to this approach is immediate access to their books.

Here’s what I’ve come up with:

HBR’s 10 Must Reads on Strategy (including featured article “What Is Strategy?” by Michael E. Porter)
About halfway through this one. So far the big take-away is Michael Porter’s defining article ‘What is Strategy?’. The short version of the answer is: Strategy is the creation of a unique and valuable position, involving a different set of activities.At this point you may be wondering: a different set of activities? Different than what? You’ll need to read the article for the answer to that.

The Innovator’s Dilemma: The Revolutionary Book That Will Change the Way You Do BusinessA couple of people I admire tell me Clayton Christensen is an important compliment and counterpoint to Porter’s position on strategy. This one hasn’t arrived yet so I don’t have much to say about the book but I am captivated by Christensen’s contribution to the conversation on disrupting higher education, including this recent article on NY Times: Business School, Disrupted.

The Strategy Book: How To Think and Act Strategically to Deliver Outstanding Results
Rounding out the initial set of books to read, I would like to go with someone a little younger, who I personally identify with. Max Mckeown is a straight talking, engaging author and speaker on the subject, with an approachable and practical sensibility I would like to emulate. I’m about three quarters of the way through this book and I am really enjoying the modern case studies and introduction to standard strategy tools, such as Porter’s Generic Strategies.

Test your mettle, MOOC style

At every inflection point in my career I’ve relied heavily on books to accelerate my climb up the front side of the learning curve, with good results. But today there is a whole new class of resources available, which I’d be a fool to ignore: Massively Open Online Courses. That’s why I’ve signed up for Coursera’s Foundations of Business Strategy, taught by Professor Michael Lenox of the University of Virginia. It promises I will learn how to analyze an organization’s strategy and make recommendations to improve its value creation by building your strategist’s toolkit. Unlike books, I will have an opportunity to discuss what I’m learning with the instructor and the other students who are attending the course.

Open to discussion

I think another vital step in hacking your way to understanding any subject is to discuss it, a lot. In the past this might have been a bit of a challenge for individuals taking a deep dive on something as unique as strategy, without the benefit of a traditional classroom experience. However, today there’s really no excuse for a lack of community. At any moment I have access to online groups, communities, forums, meetups, and literally thousands of open conversations happening on the social web via Twitter, Facebook, LinkedIN and more.

To that end, I’d like to engage in this conversation: Who are the leading voices in strategy you follow? Please leave your comments here, or connect with me on Twitter and let’s chat.