Learning from Failure: Stories and Lessons from Members of Only Influencers


One of the foundations of marketing is to test, learn and improve. The learning that comes from constantly trying and testing new approaches and tactics is one of the aspects of marketing that makes it exciting and interesting, even for grizzled veterans like me.

“We learn wisdom from failure much more than from success. We often discover what will do, by finding out what will not do; and probably he who never made a mistake never made a discovery.”

Samuel Smiles, The Lives Of George And Robert Stephenson

Whether by design or mistake, I am a strong believer in the idea that we tend to learn more from our failures and mistakes than our successes. Research is split on whether this is actually true or not.

“Our research found evidence that mistakes that are a ‘near miss’ can help a person learn the information better than if no errors were made at all,” Dr. Nicole Anderson, the senior author on the study, said. “These types of errors can serve as stepping stones to remembering the right answer. But if the error made is a wild guess and out in left field, then a person does not learn the correct information as easily.” - The Ladders

One of the reasons I believe that learning from mistakes or failures can be so powerful is the clarity it provides and realization that you must change direction from what clearly didn’t work. If you test using a single welcome email versus a 3-part onboarding series and the latter drives more immediate revenue and results in more highly engaged subscribers, you have a strong sense of what worked. And so you might rinse and repeat or tweak the series. 

But you might also declare victory and move on without a lot of reflection on what drove the better results. Your success doesn’t necessarily force you to ask the tough questions and get at root causes.

But when you fail, human nature drives you to seek answers as to what caused things to not work, or go as you had hoped or planned. It may be your own pride or curiosity, or your wanting to keep your job, but it will also likely be your bosses and other interested parties in your company who want answers.

What Some Only Influencer Members Have Learned From Failure

I asked members of Only Influencers to share their failures and lessons and what I received in return initially surprised me. I had expected lots of email marketing mistakes - which I did in fact receive some - but the more passionate and detailed responses tended to be about people’s own career or business mistakes.

I think this is another important element of learning from mistakes and failures, and that is the level of impact on you personally. The lesson you learn from rushing to get an email out and not having co-workers proof and catch that placeholder subject line is a simple one of making sure you always follow a process. Those are basic, “duh” no brainer lessons.

But when you make a mistake in your career, it can affect your employment or the trajectory of your roles and salary for the following decades. These are lessons that can become tattooed in your psyche or ones that you think about often.

Following are the stories of both email marketing, business and career mistakes admirably shared by several members of Only Influencers, followed by my own comments:

Luke Glassner - Glassner Consulting

I would say that luckily the biggest mistakes I have made as an email marketer were selecting the wrong segment/audience. The times I have done this is usually during the first few campaigns on a new sending system. Both times I sent to the full database and not the segment requested by mistake. I apologized profusely, and the result was we got a lot of extra orders so I didn't get fired because we had a positive outcome on the bottom line. 

A few years ago, I accidentally sent a sale launch announcement the evening prior to the actual sale. We had to scramble to bring pricing online for the site early and run the sale longer than expected. No one was happy about the extra work and I got some ribbing from the team about it for a few weeks, but I made it up to them with coffee and chocolates.  

I got lucky as the odd send time deviated from the norm and as a result had better than average engagement. It also proved that we could send in the evenings and it was worth testing time of day since we didn't have send time optimization (STO). The extra time the sale ran resulted in higher than expected sales, which pushed the company to beat the goal for the month. While the VP wasn't thrilled at the mistake, I was able to apologize and save the relationship.

So my advice to email marketers is if you make a mistake, make sure it's a profitable one! The only reason I was able to keep my job/client was because the outcome was positive for the business, had it been reversed the outcome would have been different. I have been lucky with my mistakes in recent years and things could have easily gone the other way.

Lesson/Loren’s Comments: Similarly, years ago I worked with a retail client that had the wrong price on a product in an email. I worked with them on a follow-up email and it resulted in being one of the highest revenue per emails this company ever sent. So if you can’t be lucky like Luke, make sure you take corrective action that results in even better results than if there hadn’t been a mistake.

John Caldwell, Founder - Red Pill Email

In ~2002/2003 I sent an email to ~3.5 million subscribers with a link to nowhere. I say nowhere because it wasn’t the link that was bad, but the destination. There were 3 environments: Development, QA, and Production, and an on-net company failover where an on-net browser would cascade through environments looking for its target. If something wasn’t seen on Production internally the browser would look in QA, then in the Development environment. 

The QA team tested the email checking that the links resolve to the correct landing pages. Check. But the landing pages never got pushed to production, so when QA tested they saw the landing page, just in the wrong environment. 

About 10 minutes after launch I get a call from my VP asking WTF? I was able to swap the link behind the scenes at the redirect/counter for the links to an active landing page almost right away and “saved” the campaign. The campaign’s results were comparable to others, so no real damage was done. 

Lesson/Loren’s Comments: In this case the obvious lesson was quite straightforward, make sure you are testing actual live production landing pages. But the larger lesson is one of process. The majority of mistakes in email marketing result from either a lack of a formal process that would eliminate virtually all mistakes, or an existing process was not followed. 

Jeanne Jennings, General Manager - Only Influencers | Founder - Email Optimization Shop (Story 1)

I think my biggest mistakes, as an email marketing consultant and in my life in general, happen when I make assumptions. They also tend to happen when I leave my ‘large company client’ wheelhouse and try to help smaller companies with their email marketing. That in and of itself isn’t too interesting, but here are some specific examples of when that really came back to bite me. All of these were years ago – I hope I’ve learned my lesson about assuming, but it may happen again…

I was doing an A/B split test with a client (I do a lot of them). I asked the email marketing manager I was working with to split the list randomly into two groups to provide control and test cells. 

I was thrilled when the test absolutely blew away the control! I was less happy when I found out that her random split was based on how long the subscribers’ were on the email list. The newest names went into the test cell, the oldest names went into the control cell. Obviously more recent subscribers on average will tend to perform much better than older names. I assumed she would understand both what a ‘random split’ meant and this basic tenant of subscriber engagement. 

We had to do the test again to get clean results. The test still beat the control group, but not by a landslide, as it had the first time.

Lesson/Loren’s Comments: For me one of the lessons here is simply the importance of having an agreed upon lexicon and definition of terms among your marketing team, agencies and vendors. 

Years ago one of the common misunderstandings was that some vendors reported open rates using “total” opens while others used “unique.” Clients were often confused when they switched vendors. And I still see people use CTR and CTOR interchangeably. 

If you are joining a new team, bringing on an agency or new vendor - one of your first priorities should be to develop standardized terms and agreed upon metrics definitions to ensure everyone is always on the same page and you keep misunderstandings to a minimum.

Jeanne Jennings, General Manager - Only Influencers | Founder - Email Optimization Shop (Story 2)

Many years ago I was doing a combination direct mail and email campaign with an 800-number CTA in both. This was a long time ago and our audience was older, so many were more comfortable calling and speaking with someone to place an order than using any type of online ordering format. 

It never occurred to me then that I needed to proof the 800 number. I was using an in-house design team and I assumed they would use the correct number. Yes, it turned out to be the wrong 800 number. 

I can’t remember how we figured this out, but it probably had to do with the company receiving zero calls two or three weeks after the direct mail was sent. We ended up calling the number, speaking to the actual owner of the 800 number and gave them a cut of the revenue to forward the calls to our call center. It still hurts to think about it.

Lesson/Loren’s Comments: I love this story. While at one level this is just another example of not having a proofing and approval process in place, but it also reinforces a trend of creative resolutions in most of the shared stories. The key when you make a mistake, is to find a creative solution that then turns it into a success.

Andrew Bonar, Founder - Emailexpert

Not so much a mistake but when I worked on the vendor side we included “a certain music streaming service” as a client. They had some AI magic working and would send out subject lines with new song titles to likely recipients who would be interested. 

A subject line went out complete with an expletive. The spam complaints rush in and I pause the campaign and get on the phone to the US. The directive is that yes, we should probably filter expletives from subject lines. But then you guessed it, after reviewing the open rates, engagement, and ROI of the campaign, we reversed course and it was unpaused.

The company decided they could live with the mistake as a result and did not make any changes to their program as a result. I was never sure if the subject line was a genuine oversight or not. 

Lesson/Loren’s Comments: Notice a trend yet? Mistakes in subject lines or body copy often can result in higher engagement and revenue. Several years ago a lot of email marketers discovered this and an ugly trend began of brands faking mistakes or putting “oops” in their subject lines to take advantage of the “rubber necker” fascination. 

In 2010 I wrote a Media Post Email Insider column, Fake 'Oops' Emails: Stop It Already, and chastised brands for using this and similar trickery. Don’t do it. But again, when there is a mistake, do take advantage of the increased engagement and opportunity to maximize ROI.

Randy Levy, VP of Sales - Zembula

If not for having DoubleClick on my resume I would have never been hired by Irene, the CEO of CheetahMail.

My career began over at DoubleClick where I went on a series of interviews and a dozen phone screens. DoubleClick was the Google of the time and their interviewing process was much like Google interviews today. Their team shared with me the start date, the fact that they were hiring four account managers and that I was not to be one of them. 

Terrible news or was it? Instead of accepting this, I suited up on that day and went on over to the West side of Manhattan and sat in their lobby for several hours to earn myself a few minutes to enroll them to take a chance on me. The VP sat with me and was perplexed about why I was there. 

I stated to her that I thought I would give her another chance and to not make the mistake of not hiring me! There was mad empathy in my statement and confidence too but in the end, I did not listen to my inner dialog and retreat nor did I listen to anyone else for that matter. She hired me on the spot and lucky for me my tech career began from there.

If I accepted their decision not to hire me I would never have broken into CheetahMail, EmailLabs and more. I feel now more than ever we must be resourceful and never accept no for an answer if we are passionate about whatever it is you are destined or wish to be doing.  

Lesson/Loren’s Comments: Great story from Randy, who I worked with at EmaiLabs back in the 2004-2005 timeframe. I’ve probably never met a more resourceful, “never take no for an answer” person than Randy. 

Not all of us have Randy’s DNA or personality, but I’ll share a similar approach from my wife. Whatever the situation, she lives by the view to ask for the moon, because usually the worst thing that can happen is the other party simply says “no.” If you don’t ask, you’ll never know.

Massimo Arrigoni, CEO - BEE

When I ran my ecommerce company in the early 2000s (ProductCart), we created a fantastic shopping cart application, way before Shopify. It supported dozens of payment gateways and integrated with FedEx, UPS, USPS and Canada Post. It offered new online merchants an incredible amount of choice and flexibility in building their online store. When Shopify came about, it supported only one payment system, its own. 

We offered incredible choices, but some significant onboarding friction. Shopify offered virtually no choices, but also minimal friction to get started selling online. 

Tobi Lutke, co-founder and still CEO of the fabulously successful Canadian company often speaks about the power of removing friction, and still applies that philosophy everywhere at Shopify. 

Although it still powers many, successful online stores, ProductCart lost the battle with Shopify: it wasn't even close :-).

The lesson I learned - the power of removing friction - is very much at the foundation of product-led growth strategies, at the very core of BEE's story, and still the number one reason for its success.

Lesson/Loren’s Comments: While Massimo’s lesson about friction was related to launching a product and company, it is fundamentally an important reminder about the importance of making it easy for customers to do business with you. As customers now interact with your brand often in new ways and channels, tracking and fixing customer struggles - removing the friction - needs to be a significant focus for digital marketers.

Craig Swerdloff, Co-Founder and CEO - Traverse Data

Early in my career I lacked any patience at all. I was insecure, and driven to prove to myself and to others that I had what it takes to be "successful". I believed that everything had to happen at a frantic pace in order for success to be realized. 

When I started a company in 2009, I nearly suffocated my team with constant sales pressure. We just weren't ready for prime time, and my lack of patience was damaging the process.

Luckily I became distracted by consulting projects, a second child, and another business opportunity. A year went by without me hovering, and sure enough the team built what I believe was the best product available in the market. Success followed. 

I now know that frantic attempts at anything are bound for failure. I have learned the importance of patience when looking to build something unique and special.  

Lesson/Loren’s Comments: Thanks to Craig for sharing this highly personal story. We all have made various mistakes in our careers, whether from personality traits, inexperience, or other factors. The key is to look internally and recognize these flaws or mistakes and correct them early. For most of us, however, we don’t come face to face with these career missteps until it is much later in our careers.

Thanks to everyone who contributed their email, business and career failures and mistakes. I hope readers are able to take away at least one lesson they can put to work in their careers and marketing efforts.

Do you have your own failures/mistakes and lessons learned? Feel free to share in the comments below.