Laugh and Learn: 15 funny stories from the marketing, advertising and public relations industries with serious lessons

This article was originally published in the MarketingSherpa email newsletter.

“Tragedy plus time equals comedy,” Steve Allen said.

“Everything is funny, as long as it's happening to somebody else,” Will Rogers said.

Last year was a hard year. So let’s start 2021 on an up note.

In this article, your fellow marketers were gracious enough to share some of the tragedies from their careers. The stories are filled with lessons, and hopefully because they didn’t happen to you, a lot of laughs as well.

I couldn’t ask others to share their comedic marketing misadventures without sharing one of my own as well. So here goes…

Story #1: Who’s on first? What’s testing second?

OK, I’ll be the first one to step up to the mic and try my hand at a funny (but lesson-filled) story.

I was scheduled to host a panel about email marketing several years ago (you can see the replay here – In the Year 2013: Email marketing technologies and tactics of the near future). One of the panelists was Miriam Geller, Director of Product Management, Yahoo! Mail. While preparing for the panel, we decided to we run an A/B split test to the MarketingSherpa list to study the impact of one of Yahoo! Mail’s newest features at the time – videos embedded in email.

I assigned it out to my team, she assigned it out to her team, and the project was begun.

Then one day, the person I assigned it to comes to me complaining about the relationship with Yahoo! Mail. He said Yahoo! wanted to have control of the testing and didn’t trust us with it, but our team wanted to use the MECLABS Institute methodology to run a true marketing experiment (MECLABS is the parent organization of MarketingSherpa).

So I said I would hop on the next call they had with Yahoo! to help smooth out the differences.

After a few minutes on the call I could see what the problem was. Their team was using the word “testing,” and our team was using the word “testing,” but they were talking about different things.

The Yahoo! team was talking about quality assurance (QA) testing. They wanted to be in charge of the QA and rightly so. This embedded video feature was new, and they wanted to make sure it was working properly before we send it out to the MarketingSherpa audience. Our team was taking about A/B split testing to determine what impact the video had on our audience’s behavior. They rightly wanted to control this aspect because of MECLABS expertise in marketing experimentation.

Once this was sorted out, it was a good laugh and everything went smoothly.

There are two key lessons here. At a base level, marketing is full of industry-specific buzzwords and nomenclature (we explain some of them for you and your new employees in The Beginner's Guide to Digital Marketing: 53 articles (and 1 video) to help with onboarding). Some are commonly defined. For others, the definition varies based on how a technology platform or agency can make money from them.

But at a deeper level, there is this quote from The Talmud that I love – “We do not see things as they are. We see things as we are.” When our team mentioned testing, of course they knew they were talking about A/B testing, that is what they work on every day. And then the Yahoo! team mentioned tested, likewise, of course they meant QA testing, that is what they work on every day. But one of the most difficult things in the world is to see life, communication, and marketing messages through someone else’s eyes. Before we get to the funny, I just want to say – that is my wish for our society in 2021. May we all do a better job of seeing our marketing, our products, our politics, and our society through the eyes of other people.

Story #2: Well…I borrowed someone else’s computer and…

“During Covid, we ran a very successful ad campaign for a client. The client was thrilled with it and remains a client until this day. But there was an awkward, humorous bump along the way that drove home a couple of important lessons for us.

In the midst of the campaign, I received a scathing email from a contact associated with the client (who is no longer with them.) This contact spotted a racy ad alongside the YouTube video we had uploaded to their channel for them. He was furious and copied the entire team for amplification. He was appalled that the company's product was appearing on the same page as an ad for a sex toy.

I had to privately explain to him what most of the people he copied on the email already knew – that Google serves ads to you based on your personal search history.

Many lessons were awkwardly learned that day. The two my team will always remember:

1) Marketers, help your clients understand how their campaign will work so there will be no surprises for them – especially embarrassing ones.

2) All of us, never blast the entire team on an accusatory email. If you do, make sure you're clear on who triggered the concern, or it could be very embarrassing."

– David Azar, Founder and CEO, Outsmart Labs

Story #3: Paper click

“When I was starting up, I had to build a marketing strategy to help advertise a fitness company that was selling supplements. I spent weeks developing the visuals, ad copy, and everything in between. The ad sets were perfect in my eyes. I would be setting them up across different platforms including social media sites, email newsletters, and traditional newspapers. After everything was ready, I sent them out to be published for the next week.

When they were published, I went back to check how they were doing. The social media campaigns and email newsletters did well, but then I got to the newspaper ad. Oh boy! I read through and realized at the bottom my call-to-action said, ‘Click Here!’ Yes, I had just asked people reading a physical newspaper to click.

What a fail!

The lesson I learned was it’s important to understand how an ad is going to be experienced along with making sure it reads well.” 

– Sara Bernier, Founder, Born for Pets

Story #4: The positives of negative keywords

“Several years ago, I had just started working on search campaigns for a wellness company. Their big offer was massage and I was excited to generate some search marketing magic for them. A few weeks into the campaign, I pulled the keyword and search term report to better understand the traffic and audience.

We were definitely getting our ads seen and discovered.

Since I had set the search campaign as a broad-type keyword with NO negative keywords, we saw that people found our ads by searching for ‘special massages,’ ‘mature women massage’ and other fun searches.

It was a lesson in intentionality and strategy in our search campaign and a huge lesson to me about different types of keywords and the importance of negative keywords, too.

But yeah, that was the time that I accidentally ranked a company’s ads for adult massage searches! No wonder the bounce rate was so high.”

– Becca Hawkins, CEO & Founder, brands by bex

Story #5: Davy Jones will take any gig you offer him

"When I was running InnaPhase we released a new software product on the market. We had been working on it for a year and when we released it, I was entranced by how attractive the UI (user interface) was.

So I created a little video of the product to the ‘I’m A Believer’ song from The Monkees.

A few months later we had a US customer meeting in San Diego. A friend contacted Davy Jones and they agreed to play at our meeting. They were fantastic.

Afterwards in the bar I asked Davy if he would come to Corsica and play at our European meeting in two weeks. He agreed. Everyone loved him in Europe, too.

So I asked Davy if he would come to Philadelphia and play in our offices for the holiday party. He agreed. He was fantastic. The staff was so excited to see him five feet away playing in the office. So basically, Davy Jones and The Monkees toured with a software company for a year!

Lesson learned: you don't know if you don't ask.”

– Dr. Jo Webber, CEO & Founder, Pod

Story #6: That weird keyboard guy

“As an attempt to increase engagement with our audience, we started a monthly challenge. The idea was our audience would participate in our challenge and possibly win a $50 gift card.

All they had to do was post a picture of themselves lubing their keyboards (yes, you read that right).

As we patiently waited for a storm of people to start lubing their keyboards in droves, the entire challenge fell flat on its face. Out of our audience of over 10,000 people, we had a grand total of two participants. Nobody was interested

So, what went wrong?

1) The challenge itself was niche specific, but a little too weird for people to show their friends and family on Instagram. They didn't want to be that weird keyboard guy.

2) We didn't promote it enough.

3) The prize wasn't exciting. A $50 gift card is not imaginative, next time we would do something more relevant and less boring.

While it was quite a failure, we look back at it now and laugh at how poorly we executed the idea.”

– Jake Harrington, Publisher, Switch & Click

Story #7: Ever notice how some PR reps don’t do their homework?

“In the first months of my public relations career at a high-tech PR firm in Portland, Oregon, I was assigned a software client in the telecommunications space. When doing research on possible editors to contact, one name stood out: Andy Rooney. I couldn’t believe the famous curmudgeon from ‘60 Minutes’ fame covered technology companies, according to the database I used.

I was excited at the opportunity of securing a high-profile client win and immediately reached out. I’ll never forget what he said when I got through to him and he picked up the phone. ‘What, What, WHAT?’ I stammered nervously as I asked him about his interest in covering my tech client and he sat quiet for a moment. He then replied ‘What in the world are you talking about? I don’t cover those types of companies. You must be an incompetent fool,’ and the line went dead.

My lessons: don’t let the stars in your eyes blind you from reality. Do your homework. Turns out there was a different tech editor at a different publication with the same name and I failed to double-check the data. Lastly, don’t rely too heavily on third-party data (our database was incomplete and frequently outdated) and do the legwork yourself.”

– Kent Lewis, President & Founder, Anvil

Story #8: The price is right

“A friend of mine was selling the first 5,000 batch of his high-tech device on Amazon, and sales were going unexpectedly well. Afraid to run out of stock he increased his price from $49 to $79 and then $99 trying to slow sales, but it didn't help: he still continued to sell well. He never looked back!

There were quite a few $40 products competing, but with great quality he had excellent ratings. There were enough people who did not want to go through the whole process of installing the device and then having to replace it. His higher price actually made people distrust the cheaper units.

Lesson 1: Never go for lowest cost, it's a race you don't want to win.

Lesson 2: Experiment. You never know what may happen!”

– Case Engelen, CEO, Titoma

Story #9: Does Lorelai run the paid search campaigns?

“Early in my career, I worked at an online education company who outsourced much of their marketing. They used a marketing agency in India. This team was responsible for many things including Google Ads, SEO, and graphic design. And, let me add, they were very expensive.

When I first began working at this company, I was a very oblivious marketer. My main job was to edit copy. I hardly ever spoke to the marketing agency in India so I really didn't understand what they did.

Fast forward a year or two. The company had restructured a bit. They hired an in-house marketing director and I was promoted to a marketing specialist. One of the first tasks I was asked to do was to evaluate the India team’s SEO strategy. After just a little digging, I discovered that the only SEO ‘activities’ this team was doing was posting our website address to about 10 forums a day. Were these online education forums, or forums that had anything to do with our service? No. They were fashion forums, second-hand selling forums, roommate search forums, etc.

To post on these forums, they needed to create accounts. Of course, they didn't use their real names. Instead, they often posted under an alias of ‘Amanda Max.’ Here's the best part: they used Alexis Bledel's picture as the profile picture.

I grew up watching ‘Gilmore Girls.’ I loved seeing Alexis portray Rory’s character. But to see her promote an online education company on a site that sold old tools and cars? Yeah, I wasn’t as impressed.

Moral of the story: be transparent in your marketing. Don’t use weak backlinking tactics for your SEO strategy. Only use Luke Danes’ picture if selling coffee.”

– Ashley Studer, Senior Marketing Specialist, Equity Commercial Real Estate Solutions

Story #10: Drunk on incentive

“This story if from my beginning days in ad sales at The Tropolitan, the student newspaper at Troy State University in Alabama. It speaks to the effectiveness of coupons in newspapers.

I had a chain convenience store as a customer at the paper. They ran quarter-page ads regularly. The regional manager called one day and asked about running a coupon for a free beer. Sure, no problem. The coupon ran, one beer per coupon.

Holy sheep dip! The Trop ran 4,000 copies each week. More than 3,500 coupons were redeemed. People were going in with 24 coupons at the time and coming out with a case of beer. The regional manager said it was the BEST promotion they'd ever done.

However, the Alabama Beverage Commission had some words for the company about giving away beer like that. The ABC wanted a limit on the number of coupons to be redeemed at one time.

Lesson learned – when you give away things, make sure you understand the market you are trying to reach. Free beer and college students? Oh yeah.”

– Ben Baker, Owner, Baker Brothers PR

Story #11: I sent out a coupon that didn’t exist...to five million people

“While managing the email channel, I once unknowingly sent out a non-existent phantom coupon in an email – to five million customers. Even worse, the email it was mistakenly included in was an apology from our CEO about a recent site-wide outage during a sale. Customers saw a message in their inboxes that said, ‘Thanks for all that you do, here's 10% off your next purchase!’ When they opened the email, there was no mention about the coupon, but rather details about how we had recently experienced technical issues during the biggest sale of the year.

One lesson from my experience is to understand what email preheaders are and their importance. The phantom coupon was not included in email content itself, but rather as copy in the email preheader – the line of text that appears next to the subject line in recipients’ inboxes. Inboxes typically use the first line of copy in the email as the preheader. You can use the copy of the actual email or add another line of text at the top of the email and hide it. When optimized, preheaders can have a decent impact on open rates.

The second lesson was how we managed customer support following the mistake. We immediately let our customer support team know about the incident and made a quick decision to award the coupon to any customers who requested it. While this didn't eliminate all damage from the mistake, it certainly mitigated it and prevented any major blow ups. Fortunately, there were no material consequences for our business!”

– Bruce Hogan, CEO, SoftwarePundit

Story #12: Mean and rude, or funny and lighthearted?

“I was a promotions director for a radio station. It’s embarrassing to admit, but my first BIG mistake taught me an even bigger lesson… always double check! I had drafted a letter on paper (actual paper—it was 2001) and gave it to an intern to type up and put together. The letter was to be sent to contestants that were finalists for a contest where they would attend the Final Four basketball tournament with an on-air personality. We mailed them—yes, snail mail—a simple personality test to try to weed out any major issues, but I didn’t check the letter before my intern mailed it out.

I was only 21 and still in college myself, so I assumed that my college intern would have the same level of detail that was required of me… but nope! She mailed the letters with about 22 typos on a single page.

But here’s the funny part: when I started receiving awful replies about how stupid I was, I used the responses as THE test! Mean and rude? Out. Funny and lighthearted? In.

It was a huge embarrassment that resulted in a great way to see how people truly act, and I learned something very valuable—never trust an intern. Kidding! But I have since learned great editing skills that I use every day.”

– Lisha Dunlap, Sr. PR Assoc., Media Influencer & Relations, University of Advancing Technology

Story #13: Perhaps this is why Elon Musk is scared of AI

“This was this week actually!! So at my other company (I lead two right now) we have three CRM /marketing automation tools we use; Intercom, HubSpot, and Mailchimp. This is an issue because the three systems don’t always talk to each other in terms of sharing data. So, I used Zapier (a tool to connect data between apps) to set up an elaborate system of automations between them. For example, whenever someone uses our app, they’re created as a ‘User’ in Intercom, and then updated in HubSpot with ‘date signed up,’ and then updated in Mailchimp to be in the segment we have for ‘Users.’ Unfortunately, Intercom bills you by total contacts, so, periodically, we delete them.

Well, a few days ago my sales team came to me and said ‘we want to see lead source attribution for contacts in HubSpot’ because that data is lost when it’s sent from Intercom to HubSpot. I’m like ‘Okay, sure.’ So, I find this new tool, Piesync, that does a two-way sync between HubSpot and Intercom (unlike Zapier, which is one-way), and set it up. Well, I forgot that we periodically delete contacts in Intercom, so when I turned on the integration I accidentally created 30,000 new contacts (the ones we deleted in Intercom but that still exist in HubSpot) in Intercom.

Thankfully, none of them triggered our marketing email automation in Intercom, but unfortunately the trouble didn’t stop there. Because these contacts were created as USERS in Intercom (even if they were just leads who’ve never used our product), the Zapier integration I’d made then resent that data into HubSpot and updated all these leads to have ‘date signed up’ as a value, which then updated them in Mailchimp as well.

Not only that, but the state change triggered my automation task creations for our sales team, who got some 10,000 new call tasks assigned to them in the span of about 20 minutes. Long story short, I had to go and delete thousands of contacts from three systems simultaneously, all of which were trying to sync with one another, all while my sales team kept getting new tasks created. I did finally fix the issue, and no harm was done, but I almost had a heart attack because I almost sent 30,000 emails and almost destroyed our entire lead scoring and lead classification system and email marketing segments in one fell swoop. Luckily, it was fixable.

Lesson learned? Avoid connecting apps to one another if you can, and instead, hook them up to a single source of truth, a customer data platform like Segment to control the sources and destinations of customer data to keep everything up to date without needing super janky dependences and automations that slowly become a black box over time! Lesson learned!!”

– Connor Wilson, Founder & CEO, Pilot

Story #14: Shop talk

“When I started out in advertising, I recall being thrown off by all of the short-hand terminology. I studied advertising in college, so I knew the basics, but I had not anticipated the volume of industry, vertical, and client-specific acronyms. Now having worked in digital media for almost 10 years, I speak the lingo like a native — but when new people join the team, I am often reminded that shop talk is a language of its own. In fact, I’ve had many arguments as to whether GTM stands for Google Tag Manager or go-to-market. Lesson: context is key.”

– Allyssa Kaiser, Director of Performance Marketing, Aerosoles

Story #15: For context…there was a time before Covid-19 when marketers actually worked in offices together

“While once working as a magazine copywriter and editor in Florida, a content marketer at one of our partners in Seattle (who I worked with regularly over the course of a year) sent me an email to say that it was her last week at the company.

I told her how surprised I was she was leaving, because her job sounded like so much fun, and she said, ‘Would you want it? I bet my boss would be thrilled if I told him I already had a replacement lined up.’

I told her that unfortunately, there was no way I could move all the way to Seattle after having just moved to Florida.

It turns out she’d been working remotely from her home in Minnesota the entire year that we’d worked together on an almost weekly basis. I never knew she wasn’t in the office alongside the other people on her marketing team I’d also been working with.

I ended up being offered and taking the job, and four months down the road, I was on a call with one of the company’s developers, who I was helping write an article for our blog, and he said, ‘Let me just run up to the Marketing floor and we can go over this in-person. Where do you sit?’ Here was another person who did not know that this content marketing role was being performed by a remote worker.

The lesson learned? Perform your job to a degree of professionalism, responsiveness, and visibility that people—perhaps even your own colleagues—are stunned to find out you’re accomplishing it all from a remote standpoint.”

– Noel Wurst, Sr. Manager, Communications, SmartBear

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