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How many times have you heard the words “simplicity and efficiency”? Now, how many times when it relates to marketing automation? For me, more times than I can count or remember. We have tried many things to help streamline our organization and our automated programs. Like always, some things we learned the hard way, and others naturally fell into place. Below are 6 items which we experienced over the years. I share these with you so you don’t have to go through the same learning curve that we did. Use one, or use them all as you, your teams, and your customers grow and change.


TIP: Be aware of low connection speeds in emerging areas and how it could affect your content. In order to benefit from this tip, you will need an open mind about industry best practices. As email professionals, we strive to keep emails short and lead the contact to our website for in-depth information. However, internet speeds can vary greatly throughout the world. In some high-growth emerging regions such as Eastern Europe, IndRA, or Africa, our team preferred to send lengthier content and include more information instead of losing their contacts to slow load times during the click-through. We also received customer feedback supporting this need. We are ‘meeting in the middle’ on this one and respecting the local expert knowledge if they need to add information to the approved content. As internet connections improve, and mobile becomes even more prevalent, we will need to revisit this conversation.


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Nothing happens unless you make it happen.

I know you’ve heard that a thousand times before. But it bears repeating: NOTHING HAPPENS unless YOU MAKE IT HAPPEN!

Here is a case in point:

One day, back in the mid 90’s,  I went to the mailbox and there was a notice asking if I'd like to subscribe to a new magazine that was starting up. A Miller Freeman publication called 3D Design Magazine. Miller Freeman was and is a huge publisher who specialized in niche technical  journals. Their big seller was “Pulp and Paper”. And they were getting into 3D Animation.


I had been working as a demo jock for a high end French 3D animation software company called TDI (I’ll save my “Never Work for a French Company when your big trade show is in August” rant for another day).  One day I noticed that one of the TDI sales guys had an article published in the big trade magazine in our industry,  Computer Graphics World.

“Hey, how did you do that?”  I asked.

“I just submitted something, “ was his answer.

What? Could it really be that simple?

I called up Computer Graphics World and gave them my background. Sure, they would love for me to write something for them on spec.

So I punched out a perennial favorite in any industry: “How to get your best deal, “ in this case your best deal in buying high end 3D animation software and hardware. (The secret ?  Buy at the end of the quarter). 

They liked it, and said it was evergreen. Meaning they would run it when they had space to fill. Nothing urgent about it. People are still writing the same article 20 years later. (In fact, our own Jason Simon wrote a similar article right here on the OI blog: See "Buying on the Quarter: How to get your Best Deal From Any Vendor.)

So now I had this subscription notice for this new and unknown competitor to Computer Graphics World in my hand. Their office was in San Francisco, so I called them up.

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Epsilon released its Q4 2013 Email Trends and Benchmarks Report earlier this month and there’s some exciting new data here on triggered messages that will help marketers evaluate their email programs.

Last week I spoke about the value of triggered email messages at the Monetate Agility Summit. Here Epsilon is breaking out performance on triggered messages not just compared to non-triggered or business-as-usual messages, but also by industry segment.

It confirms what those of us who love triggered messages already knew:

  • Triggered messages generate open rates an average of nearly 60% higher than business-as-usual messages
  • When it comes to clicks, messages triggered in response to a recipient’s actions garner more than double the clicks of non-triggered missives
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Everywhere you turn in the digital space, the word “relevant” seems to appear. Relevant ads. Relevant communications. Relevant this and relevant that. God forbid that you’re irrelevant – a ticket that some people (mostly vendors who sell “relevance solutions”) will lead you directly to Dante’s 6th circle. In email, dogma has formed that makes you try to believe that you must – at all times – only deliver product content to your consumers that is totally and absolutely relevant to them at that particular moment.

I call bullshit. Because - in email- relevance is irrelevant, once the consumer chooses you. (Cue the wailing and gnashing of teeth music.)

Why do I know this? Statistics.

In any statistical model I’ve been around, the most relevant piece of information you can have to predict future purchase behavior is past purchase of either the same product or that category of product. It’s such a powerful variable that statisticians usually eliminate it because (a) it skews the model and (b) if you actually had the category purchase data at scale, you really would not need a model. That single data element is so “relevant” that if you had enough of it, you could stop there and live off of that variable to build your business.

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Every marketer has been there. You’ve just gotten back from the conference or read an inspiring ebook on A/B testing, and you’re pumped to start your own testing strategy. And then three people need all of their emails to go out immediately, and testing goes out the door with your sanity. We all know that tweaks in our email marketing campaigns can pay off with big returns, but it’s hard to find the time to actually do it well. However, it won’t take as much time as you think if you utilize existing tools and put a bit of thought into your testing strategy.

Conversion rate optimization (CRO) is the technical term for strategically planning your tests. It’s the active process of defining the metric you’re trying to optimize, creating several hypotheses about what tweaks in your campaigns may increase your conversion rate, and measuring the effect of each hypothesis. It applies equally to email and landing pages, but I’ll limit the discussion here to email as much as possible.

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I enjoyed watching the first episode of HBO's new show Silicon Valley. The first episode revolved around whether the young entrepreneur should sell his company outright or take funds to grow it.

One of the biggest concerns of the would-be entrepreneur is exactly that: how to fund their business. And one of the biggest misconceptions around funding is  the whole notion of VC's. Entrepreneurs are often under the delusion that all they need to do is find the right investor to write them a big check and all their worries will be over. What they don't realize is: it ain't like it seems on TV. 

First of all, a reality check: VC funding is the most expensive funding you will ever take. If you self fund, or fund through friends and family, all you risk is interest charges or a piece of the profits. But when you take VC funds, you are basically putting your business and your livelihood into the hands of strangers.

Almost all VC deals are boilerplate. That is a good thing. Future investors want to see as plain vanilla a deal as possible. They don't want to see surprises. Which also means, it is pretty easy to find out exactly what you can expect in a typical VC deal.

After the VC calls and says they are ready to invest, thats when the headaches can begin and  it starts with the term sheet: the thing you need to sign in order to get the money. And when it comes to term sheets, time is on the side of the VC and time is the enemy of the entrepreneur. The VC knows this and uses it to their advantage. For instance: did you know that when you are negotiating the term sheet you are not only paying for your lawyer, you are paying for the VC's lawyer as well? It is not uncommon to be in the hole $150k in lawyers fees just to negotiate the term sheet. And the process can stretch on for months, taking up the time, attention, and resources of the founders.  By the end of the process, taking the money is no longer a nice to have, it is a need to have. And the VC's know this.

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This week, Bill continues the story of his biggest failure. Be sure to read Part 1 here first.


“In Dreamland we trace the life of our protagonist, Chad Holloway, from birth to his apparent suicide at the wheel of a high performance sports car. Like a jigsaw puzzle, the player constructs the arc of Chad’s life: the mystery surrounding his birth, his rise to political power and his eventual tragic fall, and the source of the terrible guilt that has driven him to despair. These events unfold against the backdrop of an abandoned amusement park which is governed by a strange and enigmatic caretaker named Virgil. “

dreamland1“ The events of Chad’s life, outlined below are revealed to us as fragmented memories. These memories appear in the form of video sequences, photo albums, disembodied conversations, recordings, newspaper clippings, letters, and other mnemonic devices that are discovered, via the game-play, scattered throughout the amusement park of Dreamland.”

So began the 100 page package we created for Microsoft, including a 50 page script, dozens of detailed drawings, and all the game play outlined.

The four members of Quartet rented some offices above a real estate office where we would meet each day to develop the game. Tim Gavin set up a drafting table and began producing these large, intricate drawings. Each day we could see the script we were creating take life on Tim’s table. Paul had set up a studio nearby and was creating an entire score for the game. He’d drop by with the latest musical theme for us to listen to while we played the current crop of computer games to check on the competition.

And watching Kristi was like attending a graduate course in filmmaking. When we weren’t working on the script, she would be on the phone chatting with famous producers and directors like they were her best friends, which they often were.

We flew out to Los Angeles to meet with the Microsoft team at the Digital Domain offices.  The meetings went great, Microsoft is excited, Digital Domain is excited. The lead developers at Digital Domain are telling me it is the best game script they’d ever seen. Soon, we are having lunch in Santa Monica and in restaurants with giant Jonathan Borofsky clown heads over their front door.

dreamland3Somewhere we run into Scott Ross, who along with James Cameron had founded Digital Domain, and he was sporting a huge cigar. “Everyone loves Dreamland,” he tells me. We leave LA thrilled.

Back in New York, we hear through our agent that Microsoft wants to move to the next stage. They want to sign a development deal and hand us a six figure check. We are to fly out to Redmond, WA the next weekend and sign the papers.

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Nearly every Entrepreneur lives with failure. Not in some abstract notion of failure, but real, house on the line, in your face, everything-everyone-told-you-would-go-wrong-does kind of failure. As an entrepreneur, you have the same chances of being a Zuckerberg right out of the gate as you do being born the Prince of Wales. Chances are you are going to rack up some mighty big failures. Cataclysmic failures. 

Here is one of mine: 

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In the last few years we've seen lots of innovation in the email world. We now have transactional email APIsdynamic ads within email, and completely customized experiences at email open time. And more. But what's next? Where are the big opportunities for email innovation over the next several years? My bet is on the Inbox. After all, the Inbox is the source of truth for our online life. What we buy, who we really know, who we communicate most often with - it's all there. It's no surprise then that when the Inbox is opened up for access via APIs and applications, you can make a whole range of new use cases come alive for your customers. However, given limited space (and attention spans), I'll be covering just three today.

1. Smarter Shares

'Click to Tweet' isn't cutting it

In a recent study on social sharing within marketing emails, Silverpop saw that 35% of the emails studied generated zero sharing clicks and 49% had social CTR less than 0.1%. Instead of sharing that great eCommerce offer with 1000 of your closest friends on Twitter, why not click a 'Share with my close friends' link that would grab 5 or 10 relevant contacts from your Inbox based on relevant keywords in the offer? Here's a sample app we wrote (tagline for the app: 'pass the word to your friends who might actually care') to show you how smarter sharing via email could work in practice.

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Email Marketing in South Africa is truly in it's infancy. There are few true ESP's in South Africa, and very few companies truly using Email Marketing to it's full potential.

With mobile access so high here, ESP's needs an innovative approach to capturing the leads and integrating that into a total email marketing solution. With a population of around 50+ Million, even though high levels are on cell phones, the market is growing rapidly, so its more about getting the education out to the marketplace to build a business. In the mean time, many local ESP's find that it's just easier to target international as well because of all the people in that market that just use it "as is".

There is thus huge potential for any ESP/Marketing Agency who can properly educate the market as to the benefits of email marketing, as well as getting past the ingrained objections against spending money monthly for "electronic marketing".

Anti Spam Legislation

Up until November 2013, there wasn't any anti spam legislation. This meant that end users were "legally" inundated with spam. Unfortunately this has jaded many South Africans, who look at email marketing messages with very high levels of distrust. Much more so than in other areas of the world.

In November of 2013, POPI (The Protection of Personal Information Act), was passed and signed into law. All companies have roughly a year to fully implement the regulations laid out in the act. Only time will tell if the act will be fully enforced.

The act was not specifically written for email marketing like in some other countries. It deals in all matters where personal information is collected, and has specific sections covering email marketing, SMS, direct mail, faxes and even robocall services.

Thankfully the act has pretty strict penalties of up to about US$ 1 Million per incident, and/or, up to 10 years in jail. Again, only time will tell how thoroughly these penalties will be applied.

Other Obstacles

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If you’re a marketer, you’ve no doubt heard about the 80/20 rule. For those of you who haven’t, it’s simple: 80 percent of your revenue comes from 20 percent of your customer base.

If that is indeed the rule, it means the vast majority of your business is coming from repeat customers. The question becomes: How do you create repeat customers?

The email marketing answer is a Next Logical Product program. And it down to this: When someone buys a product from you, what do they buy next? And it’s not necessarily what you might think.

Using laptop computers as an example, here’s how it works:

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With only a few weeks remaining in the quarter, this may be a great time to assess where you are in the buyers cycle with your potential new vendors. Why? Because if your potential vendor has you on the sales pipeline as a likely client, making a deal is in your favor.

Sales teams use all types of scoring methods to predict the likelihood of winning a client. This is done by assessing the stage of the sales engagement by defining finite activities and associating them with a score and a close date.

As a buyer, understanding where you are in the sales cycle can be of great benefit when it comes to negotiating a deal: most sales folks are under some degree of revenue pressure on a quarterly basis.

Qualifying a prospect and moving them through the pipeline is part science and part art. Not all opportunities are equal. For example; in the ESP space every deal includes a product demo. Up until the actual demo most prospects are not qualified well enough to achieve serious buyer status. Many sales folks will use the demo as a point of review to understand the viability of the deal.

In other words; if you do a demo with a sales team and continue to discuss options with them across a variety of topics your qualification as a viable prospect would increase significantly. Conversely, you may have completed a product demo and then been sporadic and or non responsive or not directed in your questions. The sales team will spend a lot of time reviewing the seriousness of your buying process to help decide whether or not the deal will actually happen.

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One of the things I love about email marketing is the control you can have over the process. From content and images to timing and segmentation, email allows you to dive deeply into the cause and effect of a marketing relationship.

What's ironic is that – while the channel allows for incredible control – the people who run the channel are so easily controlled and manipulated. It never ceases to amaze me how easy it is to fundamentally limit the power of the channel because the people who run the channel are afraid. The fact that it's so astoundingly simple is a testament to the power of emotion being more important than logic.

And what's the process for controlling email marketers and taking away the power of the channel?

It's easy.

Call them a spammer.

Email marketers fear that word like Superman fears kryptonite. The sad part is, everyone knows it – from CMO's to deliverability consultants. They use the spammer slur to try and get what they want...not necessarily what is best of either the consumer or the business.

So let me help you. There are three levels of email programs. One is fine. One is OK. The last means you're a spammer. I'll make it like a street light – so the brand people can understand.

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This week I received an intro/pitch email from a "sales expert" representing an ESP I had never heard of. The email,  and my follow up conversations with the sales rep, provide the fodder for this week's "Teachable Moment in Email Marketing : How Not To Write a Prospecting Email."

The names of the sales person and his company will remain hidden to protect the guilty, but here is the email I received:

"Good Afternoon,
     We are currently connected on Linked In! I am really fond of Linked In and I appreciate what it has done for me! I just wanted to send you a quick message Introducing Myself!
     My name is (removed) and I am Located In (removed), If you have never been to this Amazing City I highly recommend you to pay it a visit!
Now I do not want to waste your time with an intro email that you do not want to read! I am an Expert in the Email Marketing Field and have been now for the last 5 years! If you are looking to do some email marketing or you just need some tips or pointers DO Not be afraid to email me or give me a call!

I appreciate the time you have taken out of your day to read this email and I look forward to your response!

Thank you for your business,"


When introducing your company to someone you have no previous relationship with, it is vital to make your email seem professional. Before we delve into the content, let's start with the basics: formatting.

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Can starting a company really be as easy as raising your hand?

It can. In fact that is exactly how I started The Rich Media Sig in 1999.

Anytime there is a sea change, there are tremendous opportunities for the entrepreneur to capitalize on that change, especially in the area of technology evangelism. And creating "community" around new ideas and technologies provides low cost opportunities for developing new businesses.

1n 1999 I had established myself as one of the evangelists in the "rich media" market that was just opening up. I had served as the VRML evangelist for SGI, a computer company that specialist is high end 3D computers and was looking to establish itself as the leader for 3D on the Web. How I got the SGI job is the subject for another article but it gave me the opportunity to participate first hand in the development of new internet advertising technologies and I was part of a group of companies including Intel, Macromedia, Unicast, and InterVu that actually coined the term "Rich Media" and evangelized these technologies to the advertising marketplace.

During my time at SGI, I had produced some of the earliest rich media "banners", including a 3D animated banner for Pepsi (created by Out of the Blue Design Ltd), commemorating the landing of the Mars Sojouner space craft. I wrote about these new rich media technologies in publications like Clickz and Mediapost and so my name was well known in this newly emerging industry. I was an "influencer". And I was able to use my position as an "influencer" to launch a successful business: The Rich Media SIG.

It started with a simple post to an online forum.

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Many companies use cause-related marketing to boost their brand image, build goodwill and create positive PR. This is widely apparent at holiday time and during October, for example, as businesses jump on the breast cancer awareness bandwagon.

Following are several examples of how companies employ cause-related marketing in their email campaigns.


Bon-Ton wisely incorporates social media into this anti-bullying campaign, using both Facebook and Twitter (even asking for a retweet). The subject line, although a bit long, is designed to attract anyone who wants to join in the (virtual) fight against bullying or who simply can't resist a contest: Support STOMP Out Bullying + enter for your chance to WIN!

While the email audience is likely parents, not kids, Bon-Ton also encourages subscribers to send a text for discounts. Bullying has become a hot topic lately, and the moms who receive this email probably will give Bon-Ton a few brownie points.

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Tomorrow I turn 60.

What a marvelous age to be!
When I was 14 I watched the moon landing with my Grandfather. I always marveled at the changes he had seen in his lifetime: from the birth of plane flight to watching a man walk on the moon. I didn't realize then that I would be witness to transformations every bit as monumental.

I feel blessed to have been born in 1954: 50 years ago, when I was nearly 10, I watched the Beatles first appearance on Ed Sullivan. I know were I was when John Kennedy was shot, when Martin Luther King was shot, when Bobby Kennedy was shot, and when John Lennon was shot. In fact I even met John Lennon once, outside an Orange Julius in Boulder, Colorado.

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I have been in the direct marketing business a very long time. This means we have purchased a great deal of media to sell products as well as build various businesses owned over the past 30 years. I have also been on the media selling side of the business as well, meaning we sold advertising to both direct marketers and brand marketers.

It did not take me long to understand the difference in mindset between the two opposite sides of the table. As a media seller, I wanted to make sure that marketers were attributing as many sales to the advertising I sold them as possible.

Why would I care as a seller of advertising?

There is one major reason; so I could get a larger share of their ad spend. Of course that is why. If more sales were generated and attributed to our media, I wanted to make sure the marketer knew it came from our media. Attributing as many of those sales seemed important for me. It was in MY INTEREST to get "credit" for the sales instead of Google, or some other media source.

Now flip to the other side of the table. If you are a marketer, everyone is trying to get you to attribute online sales to media beyond the last click. Agencies do owners want the attribution (as discussed above), service providers tout their latest algorithm to attribute beyond the last click (of course so they can charge you for that service), and consultants promote this folly as well. Add the industry trades touting it and attribution models become the most important thing on the planet. It has now become standard, conventional wisdom that only an idiot would dispute.

Queue me rising to place the dunce cap firmly atop my head and proudly wear the idiot badge. In today's media environment, I am not looking for a complex, predictive algorithm attributing sales beyond the last click. And that suits me fine because the last click remains and will remain the best metric for allocating one's media spend.

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I always feel a little helpless when someone asks me, in broad terms, about best practices in email creative. The answer to that question isn't a 60-second verbal response: It's an encyclopedia of knowledge which includes the contexts, the hypotheses, the details of the tests, the results and the perceived reasons why whatever performed better beat the other options.

When you're forced to boil it down to a quick list of what's 'best practice' you have to oversimplify what you do say and there's a lot of valuable information you end up omitting.

The body of knowledge on best practices for email creative has grown exponentially in the time since I started working in online in the late 1980's at Compuserve. Today there are dozens of resources for traditional and cutting edge best practices in email creative. Here are some of my favorites:

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Starting a business is like setting out on a long journey, destination unknown and no itinerary to guide the way. Entrepreneurs don’t take the tourist package. I have both literally and figuratively put my thumb out on the road throughout my life, hitching to the next destination, unsure of when the next car would come, but always sure that one eventually would.

In 1980, I was working for a small pre-amplifier company in Boston called APT Corporation, founded by Tom Holman. Holman was a quiet genius who went on later to work for George Lucas where he invented the THX movie audio standard as well as 5.1 surround sound. The TH, in THX, stands for Tom Holman.

My job was packing and shipping out the Holman Apt Pre-amplifier, a piece of audio equipment that was light years beyond what anyone else was doing, or has done since. It had a neat feature where you could “dial out” the lead singer and just hear the backup band playing. Every day I would listen to them test each new unit by playing bits and pieces of Fleetwood Mac’s Rumors. To this day, I can’t listen to that album.

At the time, I saw myself as the future Henry Miller. I was obsessed with everything about the great writer. If I could just get to France, I thought,  I could reinvent myself just like Henry did at age 40, when he landed in France with little money, unable to speak a word of French. A few years later, he published Tropic of Cancer, the book that changed history.

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