Mythbusters: Email’s Dirty Little Secrets

Dennis Dayman, the Chief Privacy and Security Officer at Return Path – and Ryan Phelan, the Vice President of marketing and Insights at Adestra (and leaders in the Email Experience Council) – reveal email’s dirty little secrets – at &THEN in LA.


You should always design a new email every time you send a campaign.

Sure. We all know consumers don’t want to see the same thing every time. Right? And, what marketer doesn’t want to be innovative with every message? Yet, new creative – every time also means new risks.

Watch this short clip and find out why.


You don’t have to worry about GDPR, CASL and CAN-SPAM – if you are a US based marketer.

Given the current regulatory environment, in the US – and abroad, you can be in a lot of danger. Cross-border enforcement could lead to major fines for emailers who don’t have explicit permissions.

Learn more about explicit permission-in this short video clip.


You should make it really hard for people to unsubscribe from your email list.

Let’s face it – no marketer likes it when someone unsubscribes. But, when consumers do unsubscribe – it can be a “good thing”.

Find the hidden gem in an unsubscribe request, in this clip.

Looking for more facts about state of the art email marketing? Check out the Email Evolution Conference, in New Orleans from May 1 – 3, 2017.

Kathryn Minshew and the New Rules of Work

“What do I want to do with my life?” might be the quintessential question for the millennial generation. Whether this is a positive or negative position is a subject commentators having been spilling pixels about for years now and a semi-manufactured “controversy” that may never be resolved.

For those fighting for the future, though, the question is essential. It is a guiding principal for Kathryn Minshew, the founder and chief executive of The Muse. The Muse is a “career discovery platform” that has helped more than 15 million people answer that sticky question “What do I want to do with my life?”

By finding the ultimate disruption for the school guidance counselor industry, Minshew has developed quite a following. She has appeared on Fast Company, CNN and PBS and has been named to INC’s 15 Women to Watch in Tech and Forbes’ 30 under 30 in Media. As a speaker, she has given addresses at MIT and Harvard, the Y Combinator Female Founders Conference and the Lean Startup Conference.

Her latest book, “The New Rules of Work: The Modern Playbook for Navigating Your Career,” with The Muse co-founder Alexandra Cavoulacos, instructs readers on how to rule over the evolving workforce.

At DMA’s Email Evolution Conference this May in New Orleans, Minshew will reveal plenty of pearls of wisdom. Across the industry, people look to her for productivity and communication advice.

In an interview with LifeHacker, she listed a whole series of productivity hacks she uses to stay on top of everything. According to Minshew, the best advice she ever received was about persistence.

“Someone once told me, ‘No doesn’t mean no; it means wait and try again,’” she said. “I think a perspective like that is critical in entrepreneurship because you hear ‘no’ hundreds of times per day in the beginning. But ultimately, that can be your biggest opportunity: Many of our most passionate backers at The Muse are people who told us no, in various ways, in the early days, and then came around.”

Another fixation of 21st-century life is the idea of “having at all” – a concept that Minshew isn’t sold on, according to an interview last year in New York Magazine.

“I kind of hate the phrase ‘having it all,’ but I think you can have … You can have a lot,” she mused. “Not everything. But a lot. And so part of being able to do that is making the choices upfront about which of the pieces of the pie are the most important to you right now. There are other times in my life when it’ll be very important to me to work a lot less and to find a way to do that. But right now my husband is also an entrepreneur who is also scaling an early-stage business and so we are able to make it work.”

“A good friend of mine in the industry once said that if you aren’t a little bit nervous, then you aren’t pushing hard enough,” she continued on the subject of having it all. “I think that that may not actually be true for, say, the family side of the equation, but I think on the professional side, if you aren’t a little bit stressed or a little bit nervous, are you challenging yourself to the extent that you should be?”

Minshew is giving her keynote address at Email Evolution at 4 p.m. Tuesday, May 2.

This article is brought to you by the DMA. Click here to register for Email Evolution Conference, May 1-3, 2017, in New Orleans.

Is Interactive Email Ready for Its Time in the Marketing Spotlight?

Is 2017 the Year of Interactive Email? Some observers think so.

Writing on, tech entrepreneur David Bailey says interactive email is a “technical breakthrough” that’s getting little attention. But he and other experts believe 2017 is the breakthrough year for interactive email.

“Having too much email isn’t a problem. The problem is that we get too much bad email,” Bailey writes. “And there are massive opportunities to create great email that can make life better.”

One of those opportunities, he says, is interactive email.

At DMA’s Email Evolution Conference 2017, experts from FreshInbox, Nest and Shutterstock will discuss the future of interactive email during a session titled “Interactive Email: Are the Rewards Worth the Investment?”

Boomtrain, which provides a machine-learning platform for marketers, says interactive email takes hold when marketers notice a drop in customer retention from apps, websites and e-commerce platforms. “They go to the one place the average customer has spent time almost everyday for the past decade and continues to do so: the email inbox,” Boomtrain says.

However, with interactive email, marketers are going beyond traditional email to create “engaging” and “innovative” messages, according to Boomtrain. Among the examples cited by Boomtrain are:

  • “Scratch and win” emails. Interactive email transfers the excitement of traditional scratch-and-win campaigns to interactive email via mouse rollovers and clicks.
  • “Build it yourself” emails. Through an interactive email, a customer can virtually put together a puzzle to assemble a piece of furniture or build a salad through an online ordering system, according to Boomtrain. “Customers will never want to navigate away from your email,” Boomtrain says.
  • Advanced GIF– and video-equipped emails. Boomtrain points out that while GIFs and video have been featured in email for some time, marketers will take them to the next level “by giving the customer more control over the content in the emails and how they want to view it.”
  • Microsite-embedded emails. Including microsites in emails amps up their effect, according to Boomtrain. “With the right segmentation, they can be increasingly focused and deliver all the information to a customer without requiring them to move out of the inbox,” Boomtrain says.

FreshInbox says one brand that has effectively used interactive email is high-end clothier Burberry. In 2015, Burberry rolled out an email introducing an interactive scarf personalizer. To that point, the Burberry scarf personalizer was one of the most sophisticated interactive emails out there, according to FreshInbox.

Jon Carey, head of development at British digital agency bigdog, says one of the keys to producing interactive emails (like the scarf email from Burberry) is dabbling in experimentation, supported by not being afraid of failure.

“Revisit all of your preconceptions, and try to do something that takes you out of your comfort zone. It’s that ethos that has been the driving force behind the emails we’ve developed,” Carey said in 2015.

At least from a technical perspective, interactive email is doable, as 70 percent of email clients support interactivity, according to Veda Kumarjiguda, client success director at Rebelmail, which specializes in interactive email marketing.

Kumarjiguda says interactivity is a great option for educating subscribers about a product or feature, collecting information from a subscriber, letting a subscriber make a choice within an email or reducing friction in the conversion funnel.

“As corny as it sounds, you just have to open your mind to the power of interactivity,” she says.

Kumarjiguda says email remains the most effective online marketing tool, yet it’s important to improve that experience for recipients through such innovations as interactivity.

“Traditionally, email has been about taking the subscriber from the email to the website,” she says. “Interactive email keeps the subscriber in the email, which may reduce [the] click-through rate – a scary thought to some marketers. However, forward-looking marketers will see interactivity as a way to enhance email and gather unique data.”

This article is brought to you by the DMA. Click here to register for Email Evolution Conference, May 1-3, 2017, in New Orleans.

Email Ninja Training at Email Evolution

Truly effective marketing – via email and other channels – requires a strong foundation. Unfortunately, knowing where to go to learn the next level of email marketing techniques is a difficult question.

Where do email ninjas train to become email ninjas?

One dojo that is easily accessible to all is the DMA Email Evolution Conference happening this May in New Orleans. A wide range of learning opportunities exist, from the keynote speeches to discussions on the exhibitor floor, but one course for the experienced marketer that should not be missed actually happens before the main conference begins.

Email marketer expert Jeanne Jennings, vice president of client strategy and creative services at marketing firm Red Pill Email, will drill attendees in a pre-conference workshop aimed at developing a new portfolio of marketing techniques. The workshop, which takes place on the afternoon of Monday, May 1, is entitled “Developing Personas, Journeys, FBAs and Other Foundations for Your Marketing.”

“Red Pill Email principals’ leadership in the area of email metrics shows our deep understanding of how to accurately measure email,” Red Pill says of its leaders. “We can tell you how email interacts with other media, how to determine your best (and worst) subscribers and how to use data to drive decision-making – whether it be implementing an email testing program, creating customer personas to drive segmentation or understanding customer-offer matching through response modeling.”

The workshop will teach how to develop and leverage the building blocks of great marketing programs and campaigns. As an attendee, you will even have the chance to participate in interactive exercises that allow you to begin developing these foundations for your organization.

Some of the topics covered include developing customer personas, where you will take your target audiences to an extremely granular level and then flesh out what this audience thinks, feels, sees and does. You will be put in their shoes and understand their personal goals.

Then, attendees will study prospect journeys, which is thinking through the path that potential customers take to becoming actual customers. The more you understand touchpoints and influences along the way, the better you will be able to develop a marketing program to lead them through the trail, and perhaps even get them to the end goal sooner.

Feature Benefit Advantage (FBA) Analysis is, in Red Pill’s opinion, one of the most effective and underutilized tools for developing key talking points that will be used as the basis for all your marketing communications. FBA Analysis will be a focus of the workshop, as will be developing Message Maps for your campaign. Message Maps help you define and prioritize your key messages. These maps can then help you figure out how to spread these messages to your customers.

Finally, Jennings will speak about the Scientific Method, which, yes, is similar to the one you learned about in 5th grade, and Quantitative Analysis. The scientific method will help you test different hypotheses in order to develop the most effective campaign, while quantitative analysis is using spreadsheets and numbers to improve your marketing campaign. Effective marketing, by the way, is about more, much more, than pretty creative.

This article is brought to you by the DMA. Click here to register for Email Evolution Conference, May 1-3, 2017, in New Orleans.

3 Myths that Hold Email Marketing Back

With many of our email addresses approaching the legal voting age, email marketing has, understandably, a whirl of myth around it. Whether you’ve been in the industry for five minutes or five years, you’ve probably heard dozens of generalizations about email, generalizations that don’t bear fruit if you want to launch an effective campaign. Fears, myths and fallacies are holding back email marketers when the truth is that nothing has replaced, displaced or outpaced email as one of the most effective, and innovative, means to engage customers and build lifetime value for brands.

These myths will be busted at the DMA Email Evolution Conference happening this May in New Orleans. There is a wide range of learning opportunities, from the keynote speeches to discussions on the exhibitor floor, but the email track of panel discussions will be extremely illuminating.

At the “The Fears, Myths and Fallacies that Hold Email Marketing Back” session Tuesday, May 2, Justine Jordan, the vice president of marketing at the firm Litmus, will share her secrets. Based on a decade of observations, dozens of surveys and thousands of data points, this session will ease the fears, bust the myths and correct the fallacies which have deterred marketing pros from questioning the status quo and handicapped true in innovation in email.

Here are some myths that will be broken.

Code Like It’s 1999

Many people believe the coding that powers the best email campaigns is stuck in the Clinton era. However, with advances including HTML5, that is demonstrably untrue.

“Email does present enormous earning potential, but that potential often remains untapped because so many marketers are stuck in 1999,” counsels Jordan in a blog post for Smart Insights. “They see email as merely a workhorse moneymaker instead of a source of inspiration and brand engagement. Email strategies can do more than serve marketers. When done well, they can also serve their recipients.”

Jordan points out that marketers can provide value for customers via email, like sending a device user an email when the device’s battery is low.

Email Marketing is Easy

Hopefully, as an email marketer you understand that email marketing is not something just anyone can do. Yes, almost everyone these days sends and receives emails, but that doesn’t mean anyone can turn around and pull in major revenue with a few clicks.

Effective campaigns require testing and analysis – a few words in the subject line can have a massive impact on whether an email is opened. Unlike many other forms of marketing, including social media ads, email performs very well when it comes to developing relationships with your customers.

“This type of marketing is efficient because it still allows businesses and organizations to establish and maintain a strong relationship with consumers,” writes marketing expert Anthony Sostre. “If emails are used in the right way, you can improve the quality of this relationship and increase the chances to collect useful information from your potential and existing clients. This is the first activity that you should opt for when building an email list.”

And, yes, it requires effort and skill to develop such a relationship.

Email is Dead!

This myth has been kicked around for decades, and it still isn’t true. Email is one of the most popular activities online, even in 2017, and email campaigns have proven themselves to be effective over and over again.

“A classic scene from the film ‘Monty Python and the Holy Grail’ evokes the state of email marketing: A ‘dead’ man being offered up to the ‘dead collector’ plaintively insists, ‘I’m not dead,’” claims analyst firm Gartner in a report from late last year. “The scene features Monty Python’s trademark deadpan humor, but email’s role as digital marketing’s connective tissue is no laughing matter. In fact, even if email lacks the shininess of mobile and social media marketing, it’s difficult to imagine any brand’s marketing efforts succeeding without this results-oriented mainstay.”

This article is brought to you by the DMA. Click here to register for Email Evolution Conference, May 1-3, 2017, in New Orleans.

The Future Is Now: Machine Learning in Email Marketing

Slowly but surely, machine learning – the science of enabling computers to absorb knowledge without explicit programming – is invading our inboxes.

More and more marketers are embracing machine learning to personalize emails for potential and existing customers. This includes customized subject lines, time-sensitive content and highly pertinent messaging.

Machine learning empowers a brand “to send relevant, timely and engaging content to every customer, every time, at any scale,” according to a report from Boomtrain, which offers a marketing platform backed by machine learning. “It gives you the equivalent of a million email marketers all crafting individual emails for every one of your customers or subscribers.”

At DMA’s Email Evolution Conference 2017, Derek Kazee, senior director of retention marketing at Ebates, and Kara Trivunovic, vice president of digital solutions at Epsilon, will explore the role of machine learning in email marketing at a session titled “The Art & Science of Mastering Machine Learning.”

Although the use of machine learning is not yet widespread in email marketing, it has been adopted by a number of brands, and at least some of those brands are enjoying success with it.

For instance, Boomtrain says, CBS-owned foodie website has capitalized on machine learning by delivering “highly relevant” content in marketing emails and incorporating that content into customized subject lines. In addition, has relied on “delivery time optimization,” driven by machine learning, to ensure that content emails reached inboxes at the right moment.

The result? saw a 250 percent lift in engagement, according to Boomtrain, and that lift triggered a bump in repeat visitors.

“Machine learning pairs the processing power of computers with powerful, unbiased algorithms,” Boomtrain says. “It finds patterns we cannot see ourselves and applies multiple insights simultaneously to solve problems at a scale and speed that we – humans – cannot physically match.”

Another brand that has benefited from marketing emails influenced by machine learning is deals and discounts website Boomtrain says the website was seeking a way to connect users to relevant deals before those deals expired. Thanks to emails powered by machine learning, the website “was able to cut through the noise by sending users a more limited amount of content that was more likely to engage them,” according to Boomtrain.

“By rapidly developing a deep semantic understanding of new content, they were even able to include deals that were expiring that same day and automatically customize the content to ensure that urgency was communicated to recipients,” Boomtrain says.

With machine learning, the deals website witnessed a 400 percent lift in click-to-open rates compared with emails sent previously, according to Boomtrain.

Growing adoption of machine learning by email marketers will pave the way for “true personalization” of emails in 2021, according to an article published by Martech Today. As it stands now, if marketers haven’t latched onto such personalization yet, “they’re very seriously preparing to do it,” the article says.

“The long goal is using this technology to create better content and tell better stories – human content still, but content that is more effective and more relative to the company’s cause,” says Skyword, a provider of content marketing services.

OK, so machine learning is cool, but is the investment worth it? Boomtrain says it definitely is.

Weaving machine learning “into your email marketing will deliver significant performance lifts across almost any campaign or metric you track,” Boomtrain says. “Once you start sending individually customized messages, the investment can be quickly recouped in performance gains and increased efficiency.”

This article is brought to you by the DMA. Click here to register for Email Evolution Conference, May 1-3, 2017, in New Orleans.

People-Based Marketing: A ‘Strategic Imperative’

If your job involves email marketing in any way, shape or form and you’re not intimately familiar with the concept of people-based marketing, you’ve got some catching up to do.

According to a study commissioned by DMA, people-based marketing “has become a strategic imperative for virtually every brand,” with 92 percent of marketers surveyed saying that the inclusion of people-based tactics in digital marketing is vitally important.

As consumers increasingly embrace mobile devices and mobile content, people-based marketing — defined in the DMA study as the ability to recognize a customer or prospect across all of their digital devices and on any marketing platform — is a fast-growing, but still relatively new, phenomenon.

At DMA’s Email Evolution Conference, Nicholas Einstein, vice president and principal analyst at The Relevancy Group, will dive into people-based marketing during a session titled “Innovations in Identity Management & People-Based Marketing.”

A recent Relevancy Group report co-authored by Einstein found that in people-based marketing, companies that added identity management capabilities, enabling them to track customer behavior, saw higher email click-through rates than companies that hadn’t instituted identity management.

Facebook rolled out the term “people-based marketing” at Advertising Week 2014. Since then, this aspect of marketing —both in email and vehicles — has gained traction. According to the DMA study, produced by LiveRamp, 79 percent of marketers indicated they’d taken advantage of people-based marketing functions on Facebook and Google, with 84 percent saying they wanted to unify those strategies across all digital channels.

How are brands using people-based marketing? A report by DigiDay and LiveRamp says Facebook and other platforms are touting people-based marketing as a “fantastic driver” of direct response for mailing-list sign-ups, app downloads and loyalty campaigns.

“Marketers will continue to move past the world of cookies and other third-party data sources as consumers come to expect a more targeted and personalized experience,” the DigiDay/LiveRamp report says. “The ongoing shift of consumers’ attention to mobile will fuel the need for cross-device and cross-screen campaigns, all of which can be supported through a people-based approach.”

Merkle, a performance marketing agency, says people-based marketing allows brands to blend the power of first-party customer and prospect data, third-party data, digital identities and publisher platforms.

“The ability to shift your focus from devices to the individuals using those devices offers a promise of highly targeted and relevant ad content that the marketing world has never experienced,” Merkle says. “By improving the overall customer experience, people-based marketing creates enormous potential to boost conversion, improve ROI, increase lifetime value and ultimately drive competitive advantage.”

A Huffington Post article notes that mobile is the driving force in people-based marketing, with the mobile category covering smartphones and tablets along with smart cars and smartwatches.
“With the rapid rise of digital and mobile media consumption, marketers and publishers alike are faced with the challenge of delivering addressable messages that hit the mark in terms of audience, timing and place, across all devices customers use today,” says Gerry Bavaro, senior vice president of enterprise solutions at Merkle.

This article is brought to you by the DMA. Click here to register for Email Evolution Conference, May 1-3, 2017, in New Orleans.

How You Can Improve Email Campaign ROI

Marketing strategies are ideally built from the ground up by creative and analytic specialists who clearly know the campaign’s goal, the product’s target audience and the platforms that are available to drive the message home. We live in an imperfect world, so of course the reality is often far from that ideal, but that doesn’t mean marketers shouldn’t try to develop tactics that make marketing programs as successful as possible.

What tactics can marketers employ? The answer is extremely complicated, but it basically boils down to knowledge. Marketers who have experience in the industry will instinctively know what works and what doesn’t, and they can use that experience to drive campaigns further. But there’s more to marketing in the modern era than just experience. A/B split testing, regressive analytics and spot testing new strategies are all crucial ways marketers can improve their campaign performance.

So why isn’t everyone doing it?

The usual problems show up. Lack of budget, lack of time and lack of managerial direction are common complaints. But again, marketers can go beyond these typical roadblocks if they constantly look for a better and more powerful toolbox to allow them to achieve more with less.

This theme is on of the keys of this year’s DMA Email Evolution conference in New Orleans. Email marketers know more than anyone else what it means to be unloved by the executives despite just how important your channel is for corporate success. Email remains one of the best performing bottom-of-the-funnel marketing tools, especially when it comes to remarketing and upselling, yet it rarely gets the attention and budget that it deserves.

No matter – email marketers can develop their own strategies to improve customer response. That is the topic of the conference workshop entitled “Advanced Strategies and Test Plans to Grow, Engage and Convert your Customers.” Led by Holistic Email Marketing Founder Kath Pay, DEG Digital Senior Email Marketing Strategist Laura Madden and Epsilon VP of Digital Solutions Kara Trivunovic, the workshop will focus on what optimization strategies and actionable insights you can take back to your business to get your campaigns yielding even more conversions and higher revenues.

In addition to an in-depth discussion about A/B split testing, Kath Pay will look at how to drive actions for customers, using push channels to improve pull channel performance and how to analyze email campaign performance to improve future campaigns’ ROI. Laura Madden picks up to talk about strategies to analyze existing subscriber bases and how to improve acquisition efforts, with a focus on understanding the value of data to drive campaigns higher. Kara Trivunovic will then take a bigger-picture view of how to make long-term initiatives to boost customer engagement and get more executive support to improve email performance.

Join us at this year’s Email Evolution to learn how to make your email campaigns more powerful and more effective.

This article is brought to you by the DMA. Click here to register for Email Evolution Conference, May 1-3, 2017, in New Orleans.

Finding the Ideal Marketing Strategy in the Age of Choice

Choice is a powerful tool. The foundation of our democracy is based on choice.

Similarly, markets operate only when there is a choice. Being able to choose between options makes us feel good. We feel empowered, in control and free. Choice is such a powerful and useful tool that despots and dictators create the illusion of choice to make people feel better about being imprisoned and enslaved. Monopolies do the same thing, trying to encourage consumers to think they really have a choice when they don’t.

At the same time, too much choice can be a bad thing. One of the groundbreaking revelations of behavioral psychology in the last 20 years is that when people are faced with too many options, they become paralyzed and uncertain. Suddenly they begin to doubt themselves and don’t know what to do. They begin to fear making the wrong choice. In many cases, people give up and want someone else to make a choice for them, or they make a choice based upon poorer criteria than what they’d use if they had fewer choices.

The worst part: When there’s too much choice, people tend to regret the choice they made and are more unhappy with what they have than if they had fewer options when they began.

There is clearly a balance to strike between too many and too few options. This sweet spot is one of the key secrets of product development that marketers have known for decades, and now we have the science to back it up. At the same time, we want to make options for people that appeal to them on a deep, intrinsic level because they are always facing too many choices, and we want to cut through the confusion and doubt of a complex, fractured world by creating and showcasing a product that screams “I am the best!” to anyone who sees it.

Apple is great at this. The elegant, minimalist Apple Stores rewrote the rules of retail sales and encouraged dozens of copycats. The sleek lines and highly designed contours of Apple products have also focused on people’s instinctual preference for beautiful objects. That’s why Apple is one of the biggest companies in the world with one of the most recognizable brands in the world.

But their success is not impossible to replicate. It’s just a matter of understanding the psychology of choice.

That’s the key theme of one of the sessions at this year’s DMA Email Evolution conference, where e4Marketing CMO Jeanette McMurtry will discuss “The Psychology of Choice: Understanding the Science of Why We Do What We Do and Buy What We Buy.”

McMurtry will focus on how you can create a psychologically relevant message and customer experience that will drive long-term marketing ROI and revenues while also building brand recognition and loyalty among your existing and potential customer bases. The session will focus on the psychology of consumer behavior to help you understand what your customers really think when they make their choices and how you can drill into their unconscious mind to get them to pick you and your product.

Join us at this year’s Email Evolution Conference as we unpack the psychology of marketing and help you choose a winning strategy for your company.

This article is brought to you by the DMA. Click here to register for Email Evolution Conference, May 1-3, 2017, in New Orleans.

Matt Taibbi and the New Age of American Communication

Veteran Rolling Stone journalist and best-selling author Matt Taibbi is giving one of two keynote addresses at the 2017 DMA Email Evolution Conference this May in New Orleans. The provocative choice might have some prospective attendees wondering: What is one of the leading political and cultural commentators of our age doing at a conference about email?

At a time when politics seem to invade all corners of life and polarization is at unprecedented levels, communication is more important than ever. And email remains one of the most dominant forms of personal communication in 2017.

In this light, the choice of Taibbi makes a lot of sense.

He is the author of The New York Times best-seller The Divide: American Injustice in the Age of the Wealth Gap, a book published in 2014 that feverishly explores income inequality in America, especially in how the justice system treats white-collar criminals and blue-collar criminals differently.

“What I ended up finding is that it’s incredibly easy for people who don’t have money to go to jail for just about anything,” Taibbi said in an interview with NPR. “There’s almost an inverse relationship between the ease with which you can put a poor person in jail for, say, welfare fraud, and the difficulty that prosecutors face when they try to put someone from a too-big-to-fail bank in jail for a more serious kind of fraud.”

He is also the author of Griftopia, about the 2008 financial crisis, and The Great Derangement, loosely covering the Iraq War and the homefront’s reactions to it. He skewered the Democratic Party in his 2004 campaign diary Spanking the Donkey.

His latest release, Insane Clown President, collects his reporting from the past two years about the political rise of Donald Trump, the 45th President of the United States.

“This is the most extraordinary political story, I think, in our history,” he said in an interview with Democracy Now about the book. “I don’t think anything has ever—on this scale, has ever happened before. Trump—what people need to remember about Trump is—they’re overwhelmed by the horror of it right now, but they have to remember also that this was an extraordinary story about how democracy, in a weird way, does work.”

Much like his writing, Taibbi’s talks are both extremely funny and often profound. He frequently leaves listeners contemplating the fundamental American institutions we don’t often question in our everyday lives.

“[Trump] penetrated all of these different layers, these barriers to power that had been thrown up to ordinary people,” he continues. “And he was a true outsider, who somehow made it past all those barriers, through all these loopholes that we had left open. And I think that’s an amazing story that we need to focus on. How did that happen?”

Part of the goal of organizers of the Email Evolution conferences is to ask big questions about not just email, but the society it connects every minute. Taibbi promises to challenge and enlighten attendees by highlighting the varied and rich tapestry of human experiences beyond the realm of digital marketing.

This article is brought to you by the DMA. Click here to register for Email Evolution Conference, May 1-3, 2017, in New Orleans.