Stop marketing to the wrong customers
Fix this before you spend another dollar + the most fascinating new tool I've come across this year
Team,
This week’s special edition newsletter comes to you from the little gelato shop at the Park Hyatt St. Kitts, which still feels mildly absurd to type out.
A few chairs from the water, Noah covered in something sticky, and me doing that thing where I tell myself I’m not working while absolutely working. 36k Chase/Bilt points per night transferred to Hyatt, plus a short United hop from EWR.
This is country number 38 for me. Noah’s ninth. I still have not paid cash for a hotel. 🙃
All you need are points and a passport.
I realized, sitting there with melting gelato, that there’s something I’ve strangely never tackled head-on in the 178 weeks I’ve been writing this newsletter:
How little most brands actually know about the people buying from them.
A few weeks ago, I bought vanilla matcha powder because it was November in New Jersey, everything was gray, and I was just trying to feel something.
A few days later, I began receiving emails about inner peace, chakras, and self-discovery, complete with photos of women meditating on cliffs in Bali.
Someone saw “bought matcha” and decided they understood me. They didn’t ask why or consider context. They just slapped a vibe on me and moved on.
Brands spend millions acquiring customers and then speak to them as if they were cardboard cutouts. The gap between who they think is buying and who actually is buying quietly bleeds revenue every single day.
This week, I want to talk about what changes when you finally close that gap, and a tool that can help you close it.
Welcome to a special edition of the newsie. Let’s jump in.
This week’s newsie is brought to you by one of the coolest new tools I’ve personally ever seen and one that explicitly solves the problem we’re talking about today. Meet OuterSignal.
OuterSignal helps brands transform basic order data into fully enriched, actionable customer profiles.
Right now, all you get is a name, email, and address. Imagine if every order also had age, gender, occupation, social following, property value, and 100+ other signals.
With OuterSignal, you can:
1. Identify VIP customers automatically (celebrities, athletes, investors, influencers, retail buyers).
2. Crate hyper-specific segments for unprecedented personalization.
3. Build customer persona-based workflows in your CRM, Meta, and direct mail tools.
Leading brands like Create, Jolie, Magic Mind, and Mizzen + Main trust OuterSignal to power their customer personalization and increase their ROAS by up to 160x.
OuterSignal is offering friends of Eli 1000 free VIP customer searches when they book a demo through me. Tell them Eli sent you!
With all that said, let’s explore what happens when you use a tool like OuterSignal to stop treating every customer the same.
1. STOP SENDING THE SAME MESSAGING TO COMPLETELY DIFFERENT PEOPLE
A fashion brand I was talking to noticed that a significant share of customers were consistently buying multiples of the same shirt in a single order.
Once they took the time to understand who those customers actually were, the pattern made a lot more sense. They found via OuterSignal that a big chunk of these people turned out to be executives with real schedules and very little interest in thinking about what they wear beyond knowing it won’t create friction in their day.
Up until now, they’d been running a generic ad to all their customers via direct mail. They pulled the list of CEOs from OuterSignal, and the company sent that list a custom piece of creative geared towards CEOs and boardrooms.
ROAS is currently at 160X, and it’s their highest-performing campaign ever.
2. SEND GIFTS THAT ACTUALLY MAKE SENSE
During my early days at OLIPOP, we felt festive and decided to surprise and delight our top customers with a special campaign.
We selected about 20 people, spent real money on these exceptionally nice plants, and sent them out feeling pretty good about ourselves, because in our minds, this was thoughtful, unexpected, and exactly the kind of thing customers would appreciate.
And then nothing happened.
No emails, no messages, no subtle signal that anything had even arrived, which at first felt confusing and then, if I’m being honest, mildly annoying, because this wasn’t a cheap experiment and it wasn’t random.
Out of curiosity more than frustration, I did some light internet sleuthing to understand who we had actually sent these to, and the picture clarified quickly. A meaningful chunk of them were extremely wealthy, the kind that does not need our damn plant.
One of them turned out to be a billionaire VC, which, in hindsight, made the whole thing almost amusing. There’s a solid chance that the plant was unpacked by someone else, briefly assessed, and removed because it didn’t match the vibe of the house.
I heard from OuterSignal that one of their customers just discovered Kim K had been buying for 2 years. They sent her a custom card and care package, and she posted about it to her 370M followers that same week. (!)
3. BUILD SEGMENTS THAT AREN’T JUST ABOUT RECENCY AND SPEND
Most segmentation still stops at when someone made a purchase and how much they spent, which is useful context but a poor substitute for understanding motivation.
Those buckets tell you what happened, not why it happened, and they rarely reveal what would prompt someone to care again, which is how brands end up recycling the same messages and wondering why their performance plateaus.
When segmentation starts reflecting how people actually buy and live, the messaging gets quieter, clearer, and far more effective.
If you are running a pre- or post-purchase quiz and not leveraging it for segmentation, you will make me mad.
FYI: OuterSignal builds key brand personas based on the bios of every single customer. The segments are dynamic and can stream directly to Klaviyo. Brands use this to market to the person, not the purchase.
4. STOP RUNNING ADS TO PEOPLE WHO LOOK RIGHT BUT ARE WRONG
Lookalike audiences are built on shallow signals that appear scientific enough to trust and vague enough to conceal mistakes, grouping people together based on clicks, locations, and behaviors that don’t always accurately reflect their intent.
If your understanding of who buys from you is off, all you’re doing is scaling the wrong assumptions faster, and convincing yourself that performance issues are creative problems rather than input problems.
Better inputs make everything downstream work better. Everything else just gets more expensive.
I loved hearing that OS is helping brands return to the glory days of meta targeting when you could run an ad against “lawyers” with an ad for lawyers.
With OS, you CAN build a custom audience on essentially any attribute (gender, occupation, age, etc) and turn it into a hyper-specific lookalike audience in Meta so the right creative lands for the right customer.
5. FIX YOUR POSITIONING BEFORE YOU WASTE MORE MONEY ON IT
It’s easy to believe your core customer is whoever shows up the loudest in comments and DMs, especially when that feedback feels immediate and flattering.
The data often tells a quieter, more useful story about who’s actually converting and spending money, and when those two pictures don’t match, every optimization just reinforces the wrong narrative.
OuterSignal shared that they’ve had several brands tell them that the brand persona’s feature in OS saved them years of incorrect planning and totally changed their understanding of their customer base.
For example, a brand onboarded recently, thinking that the majority of their customers were young professionals in NYC, only to find out that Midwest moms were the most valuable (and prominent) cohort. That’s an entirely different avatar and persona.
6. CREATE RETENTION OFFERS THAT LAND INSTEAD OF ANNOY
Sending the same win-back offer to everyone who hasn’t purchased in 90 days is efficient in the sense that you technically reached everyone, even if you didn’t meaningfully connect with most of them.
Some customers need a discount because price is the real blocker. Others don’t care about saving a small amount because money was never the issue, they just forgot about you or need a reason that actually feels relevant to their life.
Treating those people the same way is why retention feels harder than it needs to be.
7. IDENTIFY THE PEOPLE WHO COULD ACTUALLY TALK ABOUT YOU BEFORE THEY MOVE ON
Some of the most valuable customers you’ll ever have place orders that look completely ordinary, using personal emails and different names, leaving no obvious signal that anything about the transaction is unusual.
When you can’t see beyond the order, those moments pass quietly, and the customer moves on without friction or complaint, often ending up talking about a competitor simply because someone there noticed the moment and treated it like the beginning of a relationship rather than the end of a transaction.
This is less about influencer marketing and more about recognizing when a purchase is also an intro to someone that can change your business.
8. CATCH THE RETAIL BUYER BEFORE THEY WRITE YOU OFF
Retail buyers rarely announce themselves, and the first interaction is often a small test order meant to answer basic questions about packaging, product quality, and fulfillment before any real conversation begins.
When that order is treated like every other one, the product might pass inspection, while the relationship never even begins, and by the time the brand realizes what the order represented, the buyer has already moved on.
You’d be shocked as to how many brands miss their time to get into Sprouts because they delivered a haphazard leaking can with a mediocre unboxing to the Sprouts buyer.
OuterSignal fixes this :)
That’s it for this week! Thanks again to my friends at OuterSignal for sponsoring this week’s newsie. I’m a big fan of their product and their team. If you’re not already using it, highly recommend giving it a try!
Any topics you’d like to see me cover in the future?
Just shoot me a DM or an email!
P.S. If you want to figure out how to get your brand to rank high in LLMs and show up in ChatGPT, Gemini, and more… check this out.
