The Three Retention Commandments

Hi Squad, 

The summer came and went, and September is hitting us squarely in the face, so let’s get right into it.

I'm leaving my house a few times this month, probably more than I have in the last six months combined. 😂 

I’m excited to host the second-ever Empath Club dinner next week at Mesiba, one of my favorite restaurants in New York, and a dinner with the TryNow team at Port Said (Soho) later this month.

At the end of the month, Yotpo is hosting Retention Uncensored, the first half-day event specifically geared towards Retention folks in NYC, with some of the greatest marketers in attendance. (!!)

In the last few weeks, I have chatted with Retention folks from legendary brands and have learned that, as Taylor Holiday shared on X recently, it really is a tale of two cities. 

But even amongst the brands crushing it, there are so many “best practices” that are working for some brands and doing quite the opposite for others.

I’ve long believed that “best practices” are often just another way for gurus to shill courses, promising a one-size-fits-all solution that simply doesn’t exist. Because the truth is, when it comes to retention, there are very few rules that apply to everyone. 

Today, I want to share some real-world examples that show why there’s no universal playbook for retention—and why, sometimes, breaking the so-called rules might just be the smartest move you can make (if you can strategically test into it.)

Let’s dive in.

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The Danger of One-Size-Fits-All in Retention

I’ve seen firsthand that the tactics often hailed as "best practices" can sometimes lead to unexpected outcomes—both good and bad.

Example 1: The Coffee Company’s Post-Purchase “Nourishment” Misfire

Let’s talk about a coffee company that’s been doing really well lately. They decided to step it up even more by implementing a post-purchase “nourishment” flow for their subscribers, who are a formidable part of their customer base. 

This was meant to be a series of educational emails—things like the story behind their beans, tips for the perfect brew, and even some behind-the-scenes content about their sourcing practices. Sounds like a surefire way to build loyalty and engagement vs having no communication at all post-purchase, doesn’t it?

But here’s where it gets interesting: they A/B tested this approach against doing absolutely nothing post-purchase. 

The result? The “nourishment” flow actually led to a higher churn rate among subscribers. Yep, more people unsubscribed after receiving those educational emails than when they got no follow-up at all.

It turns out that, for their audience, the added communication felt more like noise than value, and it pushed them away rather than pulling them closer.

Example 2: The Fitness Tool Company That Woke the Sleeping Bear

A well-known fitness tool company found themselves in a situation that most experts would call a goldmine—customers who were paying month after month but weren’t actively using their product. 

The traditional wisdom here is pretty clear: if someone’s paying and not complaining, leave them alone.

Why remind them they’re not using something they’re paying for and risk losing them altogether?

But they did the opposite. They decided to engage these inactive customers, reaching out to reintroduce them to the features they hadn’t been using and encouraging them to get back into their fitness routine. 

The result? Their Lifetime Value (LTV) actually went up. By reactivating these users, they not only retained them but also saw increased engagement, which translated into higher overall value.

What Can We Learn from These Contradictions?

There’s no universal playbook for retention. The coffee company assumed that more engagement post-purchase would lead to higher loyalty, but their audience didn’t see it that way.

Meanwhile, the fitness tool company took a risk by re-engaging customers who could easily have canceled their subscriptions, but it paid off in a big way.

The lesson here is simple but powerful: know your audience and test everything. 

Don’t blindly follow the so-called “best practices” just because they’ve worked for others. Your brand, your products, and, most importantly, your customers are unique. The strategies that work for you may be completely different from those that work for others.

Bonus: if you layer some technology on top of the qualitative convos and basic customer data to actually learn more about your customers, so you can retarget and ultimately retain better.

I was actually pretty blown away by this beta feature from Revenue Roll that will supercharge customer data. 

The Three Commandments of Retention

If I learned anything from these few convos I had, it’s this.

Go back to the fundamentals of retention and stop looking for a silver bullet from a LinkedIn post.

Alright, time to get off my soapbox and get practical. Here are three commandments of retention. 

1. Know Thy Customer: One Size Definitely Does Not Fit All

First things first: you really need to know your customer. Not in a vague, “we have a CRM with data” kind of way, but in a deep, “we know what makes them tick” way.

Why did those post-purchase educational emails backfire for the coffee brand? It’s quite possible that the coffee brand nailed it so well pre-purchase that their customers already knew exactly what they were getting and had a daily coffee ritual that’s more addictive than a workout.

“Just leave us alone, and we’ll consume your coffee,” they metaphorically said.

On the flip side, the fitness brand’s customers might have needed a little more hand-holding. These were folks who wanted motivation, engagement, and a bit of a nudge to stay active. 

Reaching out to those inactive users gave them that extra push they needed to re-engage. Different customers, different needs.

Some want to be left alone, while others need a bit more encouragement to keep going.

Moral of the story? 

What works for one might turn another off completely. You’ve got to understand your audience’s needs, their mindset, and what actually adds value to their experience. Know who you’re talking to and why they’re sticking around—or why they’re not.

2. Test Everything: Assumptions Make You Broke

In retention, assumptions are dangerous. Just because a tactic worked for someone else doesn’t mean it’s going to work for you. Hell, just because it worked for you last month doesn’t mean it’s going to work this month. The only way to know is to test—everything.

Look at our coffee brand example again. They could have just kept sending those “nourishment” emails, assuming it was a smart move. But by running a simple A/B test, they figured out that less was actually more. And they learned fairly quickly. 

So, what should you test? Everything. Email frequency, messaging, timing, the whole shebang. Small changes can lead to big results, so don’t just sit on your hands and hope for the best. Be proactive. Test, learn, adjust, repeat. And don’t get too attached to any one tactic—stay agile.

3. Think Holistically: A Band-Aid Won’t Fix a Broken Product

Let’s talk about the big picture. You can have all the flashy tools and sharpest strategies in the world, but if your product sucks, none of it matters. 

Retention isn’t about tricking customers into staying; it’s about making them want to stay.

Take the fitness tool company again. They didn’t just email dormant users and call it a day. They made sure that once those users came back, the product was actually worth their time. No amount of retention magic can save you if your product is a dud.

On top of that, the wrong customers will never stay. If you sold your product on an overblown premise to the wrong customer, all the tactics in the world won’t help you.

I’ll end with a hot take hoping most of you didn’t make it until here: 60% of retention is decided during customer acquisition. Sorry.

That’s it for this week!

Any topics you'd like to see me cover in the future?

Just shoot me a DM or an email!

Cheers, 

Eli 💛

P.S. Looking for inspo on your next email/sms campaign? 

I know you will love this.