Do you love your customers?

Or are you just pretending? 

Whenever I ask founders this deceptively simple question, they usually deliver one of two answers:

a) A cold hearted, emotionally-bankrupt: “NO”.

b) A delusional TED Talk about dreams, soul alignment, and cosmic vibrations. 

If you’re in the 1st tier. Do something else. Banking maybe. Heard about Private Equity?

Aldo, what does this have to do with retention? 

Everything. 

90% of startups fail because they're building products nobody wants. Ironically, 80% of companies claim they're crushing customer experience, but only 8% of customers agree. That’s a 72-point reality gap bigger than the Grand Canyon. Imagine swiping right 10 times on Tinder, convinced you’re Ryan Gosling, and getting matched with... absolutely no one. Brutal.

You say you understand customers? Harvard Business Review disagrees:

• 71.6% of companies swear, hand-on-heart, they deeply empathize.
• 35% of customers whisper sadly, "Nah, bro, not really."

That’s a 36-point empathy deficit, a.k.a. the Emotional Grand Canyon Part II.

Retention is not about vibe coding your a solution for what you think is a problem. Retention is all about putting yourself in the shoes of your customer and live the problem in your skin. 

Ask yourself this: Can a male gynecologist truly empathize with menopause? Sure, he can read a book and prescribe hormones, but empathetically? Data says nope. Female doctors consistently have lower mortality and readmission rates. Why? Because empathy isn’t learned; it’s lived.

Retention is not an abstract metric. Retention is an initiation journey that starts with empathy and ends with loyalty. (Is retention Shrek (?) Maybe).

Empathy → Setup → Aha Moment → Habit → Engagement → Retention → Loyalty.

If any link brakes, users leak, and retention dies. 

This week was my 3rd year anniversary with my wife. I’ll give you a life lesson from marriage and retention. Yes this is an attempt to become viral. What 3 years of marriage taught me about retention and b2b saas.

Setup moment. The first date. 

First impressions matter. How many users clicked signup? How many bounced halfway through the onboarding? Why? 

Mixpanel says 40-60% of users leave before completing the first walkthrough. 

Retention tactic 101: obsess over setup_completed as a metric. >50% bounce? Maybe it’s too long or unclear. Pls fix. 

Aha moment. Did your date have a WOW experience?

There's this niche Chinese app—you might've heard of it—called TikTok. Two billion users spend hours watching people dancing. Why? TikTok nailed its "aha moment" faster than you swipe away from your coworker’s cringy TikTok dances.

Products with strong aha metric— like tik tok first 5 consecutive videos watched— retain 25% more users week 1. 

The aha moment is your users’ first realization of value from your product. The sooner it comes, the more chance you get to retain them overtime. 

If your product's "obvious value" isn’t obvious immediately, users ghost you (just like your last week Tinder date). 

Retention tactic 101: Identify your users’ aha moment. Run a correlation cohort analysis. Segment users by time-to-Aha. Compare cohorts across these segments. Shorten the time-to-aha.

Habit formation. Are you the one?

If users aren't returning after 7 days, they're not busy—they’re just not that into you. Forget that outdated "21-day habit" myth from 1960; real science says habits take 18-254 days, averaging 66 days. But SaaS doesn't have that luxury. You’ve got a week tops to hook them, or you're already dead.

There’s a whole book called “atomic habit” that everyone seems to have already read, so I won’t go in depth on that. 

Retention tactic 101:

Understand the frequency of the problem you’re tryin to solve. 

Define habit triggering events. 

Track day-7 adherence 

Implement habit reinforcing triggers. 

If users don't return, it’s not because they're busy, it's because you're irrelevant. 

If you want me to tap into habit. Shoot me up a dm [email protected]

Engagement. What happens after the Honeymoon phase.

Engagement is a function of habit. It’s not a moment it’s repeated commitment. I dont understand why startups get this part wrong and confuse it with occasional excitement. Engagement means consistency in value delivery overtime, use case evolution and building trust. 

Tactical retention 101: 

Define what active user mean and track it. If the frequency of the habit is daily, then measure DAUs. 

Are they adhering to the solution overtime? Yay or nay. 

Are your triggers working out, do they lift user engagement with your product? 

Retention. Growing old together. 

Retention is pure arithmetic. Retention is all about amplification of empathy. Remember the Red Wedding from Game of Thrones? HBO got us emotionally invested, then dragged Arya’s revenge arc over three agonizing years. That’s retention at legendary levels.

Retention 101 tactic: Measure net dollar retention. Aim >=100% anything lower might be dissatisfaction signaling. 

Segment retentions cohorts, look for one with very high signal of satisfaction, go deep in to it. 

Empathy loop= consistent feedback -> adjustment -> communicate adjustment -> measure. Show users you are co-creating the product with them. 

This is not romance. This is ROI (No, not Radio on Internet). Return on investment. 

My writing advisor — Sam Altman (ChatGPT) — told me I should always include a personal story so this post can be more empathic. So here’s a bonus war story. 

>60% of our users dropped from a new feature after launch. I was shitting my pants. My lead engineer:

 “It’s obvious; I don’t get why users are confused.”

Ah the good ol' ego play.

“If it’s so obvious why are people not using it, Sherlock? Are you saying our users are dumb?”

Obvious to you is irrelevant to everyone else. 

Empathy scales with discipline. Do monthly or quarterly “customer clinics”, deep dive into real user session replays. 

Ask your team for empathy first insights. So everyone can be aligned on what is important. 

If you don't love your users, you:

-Fail during onboarding (setup).

-Miss the emotional spark (aha moment).

-Never build repeat behavior (habit).

-Lose long-term interest (engagement).

-Destroy lasting loyalty (retention).

-Building without love is ego. 

Love builds, ego destroys. 

Did we just productize empathy? Such wow. Much cool. Very amaze

If you read this far, we're dating now.

If you made it all the way to here. Thank you. Do you think this is for free? Of course not, you’ve read my mind (literally). We are in a relationship now. We need commitment. 

I have 2 asks. 

Ask 1: I want to keep helping startups solve retention. So I’ll launch a weekly challenge. I’m looking for volunteers to make public their info about retention and give live examples to our 30,000 newsletter subscribers. 

Ask 2: If you liked this post, share and subscribe :). 

Retention isn’t magic; it’s math. And empathy is its most important variable.

Let’s fix retention together. Or at least laugh trying.

Need help? DMs are open [email protected]

On June 26, 2025, I’ll run a live office hour with four startups to help them improve retention. You can apply to be one of those startups, or join as an observer, right here.