How To Win-Back Disengaged Subscribers Before You Clean Your List

It's extremely important to keep an engaged list.

Not just for your sales, but also for your deliverability.

There are ways to optimize for an extremely engaged list, which also allow for us to not have to use double optin (and end up adding an extra 20-40% subscribers to our list)!

The two most important things are:

1. Our Welcome Flow
2. Cleaning Our List

In this deep dive we're going to be covering how you can use a Win-Back Series as part of your list cleaning.

(Some people also call this a "Re-Engagement Campaign")

And if you're interested in learning more about optimizing your Welcome Flow you can also read through these deep dives:

1. Welcome Flow
2. Welcome Sequence

We're going to start by discussing a few reasons why you definitely want to clean your list, and then we'll talk about what your Win-Back Series does for you, followed by a few examples from The Hustle and mine Superhero Jacked.

📬 Why Do You Need To Clean Your List?

Before we jump into Win-Back Emails, let’s talk about why list cleaning even matters.

There are 4 big reasons to regularly clean your list — and they all lead to better deliverability, higher sales, and a healthier email ecosystem.

1. You're paying for subscribers who aren't even reading

Most email platforms charge based on your total subscriber count.

So if you’ve got a bloated list full of people who haven’t opened an email in months... you're basically burning money.

Inactive subscribers cost you real dollars — and they’re not helping your business in any way.

If someone hasn’t engaged in a while and isn’t interested anymore, it’s better to let them go.

2. Inactive subscribers drag down your open rates

The more disengaged people on your list, the lower your average open rates.

This matters because low open rates are a red flag — both for you and for inbox providers.

Let’s say you’re hovering around a 15–18% open rate. That might not seem terrible, but it could be a lot higher if your list were full of people who actually want your emails.

Cleaning out the dead weight helps you get a clearer picture of how your content is performing — and how interested your list really is.

3. Poor engagement hurts your deliverability

Gmail, Outlook, Apple Mail — they’re all watching how your emails are received.

If most people on your list ignore you (or worse, mark you as spam), your sender reputation drops.

That means future emails might land in Promotions, Spam, or not show up at all.

But when your list is engaged — opening, clicking, replying — you build a strong sending reputation.

Which makes it more likely your emails actually reach the inbox. That’s the loop you want to be in.

4. They weren’t going to buy from you anyway

Let’s be real — if someone hasn’t opened your emails in 60, 90, or 180 days… they’re probably not pulling out their wallet anytime soon.

They might’ve grabbed a freebie or signed up out of curiosity, but if they’re not engaging, they’re not building trust with you. And without trust, there are no sales.

So instead of chasing ghosts, it’s smarter to focus on the people who are opening, clicking, and showing interest.

A Win-Back Email gives cold subscribers one last chance to raise their hand.

If they don’t? That’s your sign it’s time to let them go and make room for the people who are actually excited to hear from you — and more likely to buy.

📬 How To Clean Your List

You don’t need to overcomplicate this.

Cleaning your list every 30–90 days is one of the easiest ways to improve deliverability, boost your open rates, and stop paying for subscribers who never engage.

Here’s how to do it:

Create two segments inside your email platform: 

• Segment 1: No Opens in 90 Days

This is your coldest segment.

People who haven’t opened any of your emails in the last 60–90 days.

I typically send 1-2X emails a week, so I generally go with 90 days here.

If you send more frequently, you can go with 60 if you'd like.

This group is highly unlikely to re-engage unless you give them a reason.

• Segment 2: 100% Opens, 0 Clicks

These are subscribers who appear active because they open every email, but never click anything.

This is often due to Apple Mail Privacy Protection, which auto-loads every email and inflates open rates.

If someone hasn’t clicked in 90 days, they’re probably not really engaging, and definitely not buying.

Once you’ve got these segments, you don’t have to delete them immediately.

You can send them a Win-Back Email to give them one last shot at sticking around.

That’s what we’ll cover next.

Let’s look at a few examples of how to write one that actually works:

📬 Crafting Your Win-Back Email

Before we look at real examples, let’s talk about what a Win-Back Series actually does — and how you can implement one without overthinking it.

The goal of a Win-Back Email (or Series) is simple:

Re-engage inactive subscribers before you remove them from your list.

It’s your final checkpoint before someone gets cut — a low-pressure way to ask: "Hey, do you still want to hear from me?"

If they say yes (usually by clicking a link), great — you keep them.

If they don’t engage, you move on with a cleaner list (full of less freebie seekers).

This helps improve your deliverability, saves you money, and makes sure your emails are going to people who actually want them.

How to implement your own:

You don’t need to build a complicated automation for this.

Here’s a super simple version you can run every 30–90 days:

1. Choose your timeline: 60–90 days of inactivity is a great rule of thumb. Use the segments we created earlier.
2. Pick your format: You can send:
   • A single Win-Back Email (this is what I do)
   • Or a short 2–3 email series over a few days to try and re-engage them
3. Keep it simple and direct: Let them know why they’re getting the email and what to do next if they want to stay on your list.
4. Give them a reason to click: Link to a freebie, your most popular content, or even just a “Yes, keep me subscribed” button.
5. Clean your list: If they don’t click or reply, unsubscribe them or move them to a cold segment you exclude from future sends.

Done right, a Win-Back Email is a light lift with a big impact.

Now we'll break down two real-world examples: one from The Hustle, and one from my newsletter Superhero Jacked.

The Hustle is massive and Superhero Jacked stays around 100,000-150,000 subscribers.

These are both super simple ... but they work.

Let’s take a look:

📰 The Hustle's Win-Back Email:

• Acknowledgment upfront: They know you signed up but haven’t opened anything.
• No guilt, just clarity: “If you opted in and immediately went off the grid — you keep doin’ you.”
• Simple instructions: Clear bullet points on how to make sure emails land in the inbox.
• Technical support: Offers specific help for Gmail and work emails.
• Engagement CTA: They ask the reader to click any link if they’ve actually been reading (even if not opening), to help with future deliverability.
• Bonus: They add a P.S. with a single-click link to indicate engagement.

🦸‍♂️ Superhero Jacked Win-Back Email:

• Opens with action: Tells the reader they were almost removed due to inactivity—but offers a second chance.
• Clear options: Simple fork in the road — do nothing and keep receiving emails, or unsubscribe.
• Incentive included: I re-link the subscriber’s Starter Pack and Weekly Bonuses to re-engage them immediately.
• Urgency & clarity: I use bold formatting and red text to highlight value and next steps.

📬 Where To Start?

List cleaning isn’t just a “nice to have” ...

It’s one of the most effective things you can do to keep your email performance strong and your subscriber base healthy.

Here’s what we covered:

• Why inactive subscribers hurt your performance (and your wallet)
• How to segment your cold subscribers without overthinking it
• How a simple Win-Back Email can revive or remove them — and keep your list lean
• Real examples from The Hustle and Superhero Jacked you can model

You don’t need fancy automations.

You don’t need to second-guess every metric.

Just commit to doing this every 30–90 days and your list will stay clean, engaged, and profitable.

🛠 Your Action Step:

Set aside 15–20 minutes to:

1. Create your 60–90 day inactive segments
2. Write a simple Win-Back Email (or swipe one of the examples above)
3. Schedule it to send out this week

Once you do this once, it becomes a repeatable habit that pays off every time.