How I Turn Strangers Into Paying Customers (My Playbook)

How I turned DMs into $800 MRR (And growing)

Over the past few months, many people have asked me about the DMs (Direct Messages) I send.

→ How do you start a conversation?

→ How would I know what to say?

→ Why should I even send DMs?

→ This is awkward. I can’t do it.

→ What if I get no responses?

Read this and you’ll know exactly who to DM, what to say, and why it works so well.

Why Send DMs?

The best way to build an audience is via writing and engagement.

Writing weekly/bi-weekly articles, daily notes and commenting/liking others’ creations.

The best way to build a loyal, engaged audience? DMs.

I have a note I keep repeating in different forms:

→ Articles build trust

→ Notes build a community

→ DMs build loyalty in the community

This is where you get the chance to really know people and share your story with them. Personally.

I can’t stress enough the importance of it. People appreciate it.

Imagine that a creator that you like sends you a message, saying hi, asks about you and starts a conversation with you.

How would that feel? Awesome, right?

The Importance of DMs on Substack

If you only take one thing from this article, this is it.

Substack’s has a hard limit on DMs: You can start up to 10 DMs with non-connected users.

Non-connected = not following you or subscribed to your newsletter.

This is a very low limit. And the moment you start sending DMs to people, you’ll feel it.

Assuming you start hitting this cap today. In 3 months you will have sent:

\(10(DMs/day) * 3(months) * 30(days/month) = 900(Sent DMs)\)

Based on my statistics, 78% respond.

\(900 * 0.78 = 702 (connections)\)

702 potential connections.

702 potential subscribers.

702 potential customers.

And this is not an email with 30-40% open rate. It’s a personal, direct path to people with whom you have a connection.

And the sooner you start, the better.

But, Orel, I don’t need it yet. Maybe in the future

Russell Brunson, the author of the Secrets trilogy (Very popular marketing books), wrote in “Funnel Secrets”:

“Dig your well before you’re thirsty”

Start building the DMs today, so later down the line you’ll have it ready.

Who do I send DMs to?

There are two types of people you can send DMs to:

1. People who engaged with your content (Type I)

2. People who didn’t (Type II)

Type I People

The first type of people is easier, because they most likely follow and you can send them all a DM in one sitting, no limits.

Type II People

The other type is where things gets tricky.

You are looking for people who might be interested in what you have to say/sell.

Sending DMs to everybody else is wasting your time and their time.

You need to find relevant people that already read other articles in your niche, so you know there’s a good chance they’ll like your content as well.

Here are 5 ways to find them:

1. Use Substack’s topics section (Bad)

2. Track people who engage with articles you like (Good, but time consuming)

3. Ask other creators for referrals (Inefficient)

4. Find notes that interest you and DM engagers (Good, but time consuming)

5. Use WriteStack’s Radar feature (Best)

Now that we know how to find potential readers, it’s time to start sending DMs.

Types of DMs

In our case we have 2 types of DMs

1. Cold

2. Warm

3. Semi-warm

Cold

These are the people that have never engaged with your content and they don’t know about your existence.

This group has most of the people you are going to contact.

Warm

This is your audience or people you already sent a message to.

You have got to know them and they know you, you have built a connection and maybe even had a Zoom call.

We won’t talk about those in the playbook, because you already contacted these people.

Semi-warm

This is the group of people who liked/commented on one or more pieces of content.

They know you, they like your content. They’ll probably appreciate a DM.

Pro Tip to Keep Track of DMs

Before we jump into the actual DMs, I want to give you this tip to avoid wasting time opening a DM you already opened.

Whenever you send someone a DM, follow them!

That way, when you see them on your note’s like list, they’ll appear as following and you’ll know you can skip them.

Following allows you both to track and to see and engage with their content.

How To Send a Cold DM

This is the most time consuming DM.

In order for it to be effective and have a higher open rates, you’ll need to write a personalized message.

Either skim an article they wrote or a read few notes and send them a message about those.

Here a few scenarios and DMs you’d want to send:

1. Relevant Comment on Their Content

This is the most useful type of DM you can send.

It’s based on the person’s content, be it a note or an article, you send this to show them that you read their content.

There are 3 types of DMs I send. They all start the same:

Hey X!

I read your article / I read your note about consistency (Any topic it’s about).

It’s amazing to see how effective consistency is. What else do you write about? (Can be any question)

You can also be blunt and lazy (lower response rate) and send this instead

Hey X!

I read your article / I read your note about consistency (Any topic it’s about) and I love your writing, so I decided to say hi.

How are you doing?

2. Overlapping Interests

You’d want to use overlapping interests when you found someone through another creator’s article.

So if I, for example, found Bob through Alice’s Substack, which is about Encryption, I’d write to Bob something like this:

Hey Bob!

I see that you’re also a fan of Encryption and you read Alice’s Substack! Let’s connect.

How are you doing?

Nice and easy.

3. Random Creator

This type of DM will get you the least amount of responses, but requires the least amount of effort.

Honestly, I rarely send those, but just in case you need it, I’ll give an example using real messages I send about WriteStack

Hey X!

I created a tool to help Substack creators grow and I would love it if you could give it a go.

In return, if you love it, I’ll let you use it for free :)

What do you think?

It’s important to end with a question. It will increase the response rate dramatically.

How To Send a Semi-Warm DM

These are my favorite DMs to send.

They’re easy, the response rate is very high and the connections created have the highest quality of them all.

This is the message I send:

Hey X!

I saw that you engaged with my notes and I decided to connect :)

How are you doing?

That’s it! As simple as that.

Some people find it hard to follow up when the other party is not very talkative, didn’t reply with a question or the conversation feels like it’s hit a dead-end.

So here’s an easy follow-up:

What are you up to these days?

This is a strong line that will usually do the trick and get them talking.

And if they still refuse to engage in a meaningful conversation, that’s fine. You can move on :)

You have a new DM that you don’t need the approval of.

Final Thought

DMs are leverage.

Most people waste time writing (only) into the void and wondering why they don’t get any engagement.

The smart ones are building relationships through DMs.

You don’t need to go viral. It’s nice, but if you create 5–10 real connections a day, you’re golden.

That’s how you build an audience that supports, shares and buys your work.

So stop overthinking it and send a few DMs now.

Your future self will thank you.

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P.S.

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