How To Turn Free Subscribers Into Paying Customers

Little-known strategies that made me $5,000/month from 3,000 subscribers

95% of "newsletter" advice you see online is garbage.

They tell you to:

• provide value first

• nurture your list

• build trust

Sounds nice, right?

But here's what they don't tell you: Following that advice is exactly why your list isn't making money.

I've built 5+ different online businesses since 2011. Each one powered by email. And the most profitable lists I've ever built broke most "rules" the gurus preach.

Most stuff you've "learned" about converting subscribers is backwards. Here's what really works.

You're probably screwing this up

Most people will tell you that you need tens of thousands of subscribers to make $100,000 a year.

Bullcrap.

I made that income with less than 5,000 email subscribers.

But it wasn't always the case. A few years back, I had an email list with ~10,000 subscribers and I was barely making $50k.

The difference? I stopped treating my email list like a charity.

When I started 10 years ago, I made all the classic mistakes. I gave away everything for free, thinking I'd "earn the right" to sell something later. I was terrified of looking salesy. I'd wait weeks (sometimes months) between offers, afraid to annoy my subscribers.

The result? A list full of freebie seekers.

Here's what had to change…

The best timing to ask for the sale

Stop waiting too long to make an offer.

I thought I'd earn the right to sell something down the line. Wrong.

If you never ask people to buy something early on, they assume you'll never ask them to buy anything. It's a mental loop that's almost impossible to escape from.

Think about it like training a dog. You set expectations from the beginning, not after six months of letting them pee on your carpet.

Same with your email list.

I train my list to buy from the very first email. The price doesn't matter. What matters is training them that you're a business, not a charity.

If it pisses them off? Good. Let them unsubscribe. There's no point in building an email list full of tire kickers who expect everything for free.

I'd rather have 10 buyers than 10,000 freebie seekers.

Every email should have a call to action to something you're promoting. If you don't have enough products to sell, start by promoting something as an affiliate. The key is setting the right expectations from day one.

The relationship-building secret

You're dumb if you're only sending "free value emails."

The second dumbest thing you can do? Only email when you have something to sell.

"Hey, it's been 6 months… buy my thing!"

That's like the friend who only calls when they need to borrow money. Don't be that guy.

The secret to converting subscribers is consistency. I send daily emails to over 10,131 people. 35% open them. That's 3,545 people reading my stuff every single day.

Does it piss some people off? Absolutely.

But I don't write for everyone. I write for the 100 superfans who actually buy my stuff.

When you show up daily (and do things right) you become part of people's routine. You're that email they actually wait for. That voice in their head pushing them forward.

You can't build relationships with quarterly check-ins.

The math is simple: More touchpoints = more trust = more sales.

Most creators email once a week and wonder why nobody buys.

But you don't need to turn into an email extremist like I am. 2-3 times a week does the job, too.

Some people will unsubscribe. Those aren't your customers anyway. Get them off your list.

Stop sending just "newsletter" content

You folks on Substack & Medium will hate me for this.

But emails are NOT blog articles.

I get it. You want to "emulate" your guru. You want to repurpose your content everywhere. Maybe you're a bit lazy and think, "Hey, I'll just copy-paste my latest blog post into an email."

Blog articles don't build relationships. They simply get you discovered.

A better way? Make your emails read like emails.

Do you get blog posts from your friends or colleagues? I don't.

Share:

• Personal stories

• Embarrassing failures

• Controversial opinions

• Quick insights that tie back to a problem my audience has

I try to make my emails feel like they're written just for you. You can even read them on the toilet.

95% of my clients tell me my emails resonate with them. Because I'm not hard-teaching – I'm simply having a conversation.

Start writing like you're talking to a friend (who happens to have the exact problem you can solve.)

Create products your subs want to buy

I still don't understand people obsessed about selling $7 Gumroad ebooks or $20 Substack subscriptions.

Stop doing it. When you have a small audience, you're wasting your time.

And you know what's even crazier?

Simply because you're slamming down the price doesn't mean that the sale is going to be easier. It's sometimes easier to sell a $200 course than a $20 subscription.

People willing to invest in one of your products will pay whatever you ask for it. As long as you know how to package it.

When you have back pain and your mattress hurts you don't care if the orthopedic mattress costs $800 or $2,000. You just buy it.

Every night of good sleep is priceless compared to tossing and turning.

So instead of under-evaluating yourself, put an honest price tag on your digital product. A price that respects you, and gives your customer a good deal.

The amount of effort to sell a $7 ebook is the same as selling a $400 course.

Read this again.

The welcome sequence strategy

Getting people onto your email list is hard.

You need to churn out a lot of content. Now you also need to write a welcome sequence? Phew… That's another thing on your plate. So it's easy to get lazy and let them wait for your next broadcast.

But the reality is that your welcome sequence is one of the most important emails that you're ever going to send out.

When someone joins your list, they're hot. They just raised their hand and said, "I'm interested." That's when you strike.

Within the very first sentence:

• talk about who you are

• how you can help them

• where they can unsubscribe

• and that your emails will also promote your products and services.

That way you frame the conversation.

The long-term game of email marketing

Email marketing is 11 times more profitable than social media.

But it won't turn you into a millionaire by next Tuesday.

Each email you send:

• Builds more trust

• Creates more touchpoints

• Increases the chance of a sale

Some of my readers have been with me for 10 years. They've bought every product I've created.

Most creators quit after 3 months because they're not making money. They jump to the next shiny object.

The math is simple: If you can get just 100 true fans who spend $1,000 with you per year, that's a six-figure business.

The compound effect is real. But only if you stick around long enough to see it.

Time to stop leaving money on the table

Turning free subscribers into paying customers isn't rocket science.

It's about mindset first, tactics second.

Stop being afraid to sell. Stop sending boring newsletters.

Instead:

• Show up consistently

• Make offers from day one

• Write emails that build relationships

• Create products people actually want to buy

• Use welcome sequences to indoctrinate new subscribers

Selling isn't sleazy when you're solving real problems.