3 email mistakes that may have cost Trump millions

Trump sends first fundraising email

Donald Trump's first fundraising email has set new records. Never before has a US presidential candidate's email campaign had such high spam complaints.

According to numerous sources, including Ad Age and data from Return Path, more than 50% of emails sent on June 21st from Trump's first fundraising email went to spam, while many others made email complaints.

To put this in context, a 1% spam complaint is already considered unacceptable. The same rookie email marketing mistakes that caused Trump's emails to go to spam also kept his email open rates low.

Trump's fundraising spam email even reached British MPs and the singer Cher, who publicly called out the tweet to her 3 million followers that, "Obviously they aren't checking their lists."

So what did the Trump campaign do wrong with their first fundraising email?

Let's take a look at these mistakes and how they could have been avoided:

Mistake #1: Not Understanding Basic Email Deliverability

Since founding the cold email consultancy, Salesfolk, I've seen dozens of Silicon Valley startups make rookie mistakes that have ruined their email marketing campaigns, but never before from a presidential candidate.

You can't just start sending millions of emails to people from a new domain or IP. Trump's first fundraising email was sent from donaldjtrump.com, a brand new domain that didn't have any trust or prior reputation with mail servers.

Why would they do this?

While many software companies' sales organizations build or purchase their own lists of contacts, political camps don't usually buy their email lists--they just rent them from a third party.

My guess is that because no one had ever gotten emails from this domain before, mail servers did not trust it, and many Trump supporters even thought that this email was a scam or possible phishing attempt.

Combine that with other amateur mistakes--like incorrectly configuring their email records, and not taking the time to build up their new domain's credibility--and emails will certainly go to spam.

Whenever you start sending emails from a new domain, you need to first "warm it up" by sending out a much smaller volume of emails over time to establish trust and credibility. You should also first try to build rapport with your audience before directly asking them for money. Usually, this would be done by first sending a sequence of emails that both add value and establish credibility with the target audience.

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Mistake #2: Having A Poorly Targeted Email List

Whether you're a software company sending sales emails to potential customers or a political candidate trying to fundraise from your supporters, you need to have a good email list.

The angry comments about Trump's emails from Cher, British MP's, and hundreds of others make it pretty clear that his campaign purchased a low quality and poorly targeted email list of contacts that had never opted-in to his emails.

It's no surprise that Trump's fundraising email had spam problems. Trump's emails already had little trust since it used a new domain to send from. Not to mention, they were sending spammy unsolicited emails to a large group of people, many of which probably did not want to receive his emails to begin with.

Trump would probably have gotten much better results if his campaign had made an effort to build an organic list from his supporters. Although, when Trump's campaign chose to rent an email list, they should have vetted its quality more and gone for an option that would allow them to do better targeting and segmentation. This would have allowed them to reach people who were more likely to be his supporters, rather than carpet-bombing his opponents with spammy emails.

Also, they should have done a lot more testing by sending emails to a smaller number of contacts. This would have allowed them to see which segments of their audience responded to specific messages, so they could optimize their email campaigns for better results like the Obama camp previously achieved through A/B testing.

Likewise, if they had initially sent fewer emails earlier on they would have probably been able to build better reputation and trust with mail servers. This would have helped them avoid having so many of their emails getting stuck in spam.

Mistake #3: Strange Formatting And Mediocre Copywriting

In the last 5 years, I've written thousands of emails and managed the email campaigns for at least 300 companies. I've run A/B tests with hundreds of thousands of people and gotten open rates well above 60%, with nearly all of my click-through rates in the double digits.

The first moment I looked at the emails the Trump campaign sent out, my knee-jerk reaction was, "These look really spammy, and this email copy sucks."

Trump's fundraising email was full of bold and highlighting with ugly HTML buttons. It almost reminded me of one of those scam emails from a "Nigerian Prince." They had too many images, which also might have been one of the things that tripped up spam filters.

The subject line, "The First One," wasn't very appealing or interesting, especially if it came from a domain people were not already familiar with.

The email copy itself seemed super spammy and obnoxious too.

This was the Trump campaign's first fundraising email, and while people most likely already know who Trump is, it usually doesn't work well to write an email that talks all about yourself and then asks strangers for money right off the bat.

I'm pretty neutral politically, but from a purely copywriting perspective, I think Bernie Sanders and Hillary Clinton have done a lot better with their fundraising texts and emails. Friends of mine showed me texts and emails they got from Bernie advocates on their phones months ago, and they were much more personalized and thoughtful.

The tone from Bernie's messages felt much more human and less aggressive, with pleas to "get the word out," whereas this email from Trump quickly jumps to directly asking strangers for money.

Whether you're a salesperson or marketer trying to get new customers for your company, or a political candidate fundraising, you probably shouldn't be so pushy and self-focused with your emails if you want to actually make money.

Correction: An earlier version of this column mischaracterized Adestra's role in the Trump domain creation and email, as well as the company's development stage and industry standing. Adestra is a software-as-a-service email-marketing company in business for more than 10 years and recognized by email networks. While the service was used in the email campaign, Adestra did not have a role in managing it.

RELATED: Donald Trump's best books

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Donald Trump books

Trump: The Art of the Deal (1987)


The America We Deserve (2000)

"The America We Deserve is Donald Trump's position paper on the major political issues facing our country."

Trump: How to Get Rich (2004)


Trump: Think Like a Billionaire: Everything You Need to Know About Success, Real Estate, and Life (2004)


Trump: The Best Golf Advice I Ever Received (2005)

"The host and coproducer of the megahit reality show The Apprentice presents a unique collection of golf advice."

Why We Want You to be Rich: Two Men – One Message (2006)

"Donald Trump and Robert Kiyosaki wrote Why We Want You To Be Rich because they saw how the turbulent economic climate would impact the middle class."

Think Big and Kick Ass in Business and Life (2007)

"Donald J. Trump is an icon: the very definition of the American success story. Republican Presidential candidate, reality-television star, and developer of some of the planet's most prestigious real estate, he's also become one of the world's wealthiest men."

Trump: The Best Real Estate Advice I Ever Received: 100 Top Experts Share Their Strategies (2007)

"Donald Trump has gathered in one book the best advice on real estate from the brightest and most experienced people…"

Trump 101: The Way to Success (2007)

"In Trump 101, Trump himself becomes your personal mentor and coach as he shares tips, tactics, and strategies, all designed to help you make the most of yourself, your career, and your life."

Trump Never Give Up: How I Turned My Biggest Challenges into Success (2008)

In Never Give Up, Donald Trump tells the dramatic stories of his biggest challenges, lowest moments, and worst mistakes—and how he uses tenacity and creativity to turn defeat into victory.

Think Like a Champion: An Informal Education in Business and Life (2009)

"Over the years, Donald Trump has written many bestselling books, and he has also written short pieces that summarize his singularly successful tenets on how to live the good life, both personally and professionally."

Midas Touch: Why Some Entrepreneurs Get Rich—and Why Most Don't (2011)

"In Midas Touch, Donald Trump and Robert Kiyosaki ask the question: What’s an entrepreneur’s most important job? The answer: creating high-quality, stable jobs.
And in today’s marketplace, “jobs” are in high demand — and so are the skills and the innovation and vision of entrepreneurs."

Time to Get Tough: Making America No. 1 Again (2011)

"2016 Republican presidential candidate Donald J. Trump has a plan to make America great again."

Crippled America: How to Make America Great Again (2015)



For more tips on writing better emails that people actually enjoy getting, check out these 7 tips for email campaigns.

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