5 Questions to Ask Yourself Before Starting a Paid Newsletter

Visual Freedom

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More than a decade ago, self-proclaimed marketing experts assumed that email marketing is dead. Yet, the reality in 2021 is that email marketing is not only alive, but it’s thriving.

Studies show that more than 4.03 billion people worldwide use email in 2021 and the number is expected to grow to 4.48 billion by 2024. Additionally, 99% of all people report checking their emails daily.

Social media is nice, but no other platform comes close to a similar reach.

But what’s even more impressive is the rise of paid newsletters. We’re currently in the middle of a little revolution that might forever change the nature of newsletters.

While most people describe typical newsletters as spammy or annoying, at the latest, the rise of Substack turned the game upside down.

Now, people are paying to receive emails from their favorite writers, creators, and thinkers. On Substack alone, more than half a million subscribers pay a monthly fee to receive those exclusive newsletters.

As a digital entrepreneur and online writer, I’ve been curiously observing this exciting transition for more than a year. Naturally, I said hell yeah when I had the opportunity to create a joint-paid-newsletter with three amazing fellow writers: Michael Thompson, Zulie Rane, Amardeep Parmar.

And soon, we launched Write Your Future, an exclusive newsletter dedicated to helping online writers increase their audience and income.

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Write Your Future — Photo Courtesy of Author

Our promise is simple:

We are a diverse team of writers, coaches, and freelancers. We reach millions of readers each month and have made over $500K writing through our writing and the doors it has opened. By joining our weekly newsletter, you’ll get full access to all the tips and lessons that helped us build our writing careers.

Less than a month after our launch, we had welcomed 100+ paying subscribers, generated a 5-figure annualized revenue, and got featured among the Top 15 newsletters in the Literature category on Substack.

Instead of overthinking our collaboration, we trusted each other, moved fast, created the first version of our letter in just a few weeks, and went live.

Yet even though we moved fast, we didn’t forget to answer some critical questions before deciding to dive into it.

If you’re thinking about starting your own paid newsletter, asking yourself the following questions might save you lots of time and effort:

Which problem am I solving?

If you’re writing online to make money, you’re not only a writer but also an entrepreneur. And even if you don’t like to admit it, you’ll need to think like an entrepreneur to build a profitable and bullet-proof writing business.

My favorite way to describe entrepreneurship is to see it as an analogy to solving problems.

As an entrepreneur, you make money by solving other people’s problems. Similarly, even if you're not aware of it, your writing might be solving problems for your readers.

And of course, your paid newsletter needs to solve a problem too.

When we first had the idea to launch Write Your Future, we knew that we could help thousands of online writers by delivering great content.

On Medium, less than 10% of all writers make more than $100 per month. Overall, the percentage of bloggers and freelance writers who generate a significant income through their efforts is even less.

As four writers with a significant base of readers and a substantial writing income, we knew there’s a lot we can share to help other writers create similar results.

If you’re thinking of launching a paid newsletter, ask yourself which problem you solve for your audience.

Maybe you’re sharing expert advice on a specific topic as we do?

Maybe you’re delivering entertaining or thoughtful content?

Maybe you’re sharing your unique journey and take your readers behind the scenes of your life or business?

Whatever it is that you’re planning to share in your paid letter — make sure you know what you want people to pay for.

If you don’t know it, it will be tough to convince people to pay for your product.

Do I have an existing loyal audience?

Now that paid newsletters are becoming more popular many people think it’s one more of these “get-rich-quick-schemes”. But here’s the reality: You can only build a profitable paid newsletter if you already have an existing audience.

Many people think they can sign up on Substack, write some lovely emails, and watch the subscribers and monthly earnings grow. Unfortunately, that’s not how it works.

To make a significant income through your paid newsletter, you’ll need to be great at marketing it. And this starts by being able to reach out to your ideal audience and to people who already know and trust you.

Combined, my co-founders and I have more than 100,000 followers on Medium. I’m running one of the largest and most active Facebook groups for our niche, and Zulie owns a highly targeted Youtube channel with 10,000 subscribers.

Long story in short: We knew that we would reach a considerable number of online writers through our marketing campaigns.

A paid newsletter is not a way to grow your audience; it’s a way to monetize your existing fans.

If you’re at the beginning of your journey as an online writer, a paid newsletter is not what you should create. Instead, you need to create free content to first attract and build an audience.

Once you’ve gained their trust, you can think of monetizing your content through an exclusive newsletter.

Is your existing audience willing to pay?

Even though having an audience might sound like the most crucial part of the decision, there’s a question that’s even more relevant: Is your existing audience willing to swipe their credit cards?

Here’s the harsh reality: If your audience is used to getting content for free and you never tried to sell anything to your email list or followers, you might have a hard time convincing them to pay for your newsletter.

Many creators make the mistake of giving away so much content for free that they educate their audience not to pay for their ideas.

I even know creators who faced a little shitstorm when they pitched a product for the first time after serving their email list for free for years.

Realistically, only a small portion of your existing fans and subscribers will join your paid newsletter anyway. Yet, if you’ve always been afraid of selling to your audience in the past, you might also fail to sell your newsletter.

So don’t only ask yourself if you have an existing readership but also determine whether these readers would be willing to open their wallets to receive your newsletter.

And while you do that, also keep in mind that demographics might play a role too: Who’s your ideal reader? Where do they live? How much money do they make? Can they even afford to pay $5, $10, or more for your exclusive letter? Do they need to sacrifice anything else to receive your emails? Would they do that?

At Write Your Future, we’re serving online writers who are interested in growing their income.

We’re convinced that helpful advice is worth its price, so we’re confident about charging more than most similar newsletters. Additionally, three of us are already monetizing our expertise through other ways, such as coaching or editing services, so we knew that our existing fans would be willing to pay for our letter.

Can I offer something different instead of just “more”?

Most paid newsletters of writers aren’t profitable because of a simple mistake: They deliver more of what’s already existing.

And the reality is that most readers aren’t willing to pay for more, but they’re happy to pay for something different.

If you’re publishing free content on your blog or any accessible platform, it’s going to be hard to convince people to pay for more of the same content.

Some readers might subscribe because you are their favorite writer or because they want to support you financially, but most of them won’t care. The harsh reality is that most of your readers probably don’t read all your articles and books anyway.

And let’s be honest: Paying to receive more of something that’s already available for free doesn’t sound particularly interesting.

Instead of doing more of the same thing, ask yourself if you can offer something entirely different.

Maybe you can share exclusive insights?

Maybe it’s in-depth guides?

Maybe it’s vulnerable stories you don’t share elsewhere?

One of the main reasons Write Your Future made it to the trending lists so quickly is because we created something brand new.

You can find free articles with writing tips from all four of us, but there’s no other place with advice from four different writers.

We believe that each writing journey is unique and all four of us built profitable writing businesses through different approaches, so we can share the whole spectrum of what it takes to build your audience and income as an online writer.

Last but not least: Is it worth it?

Launching a paid newsletter is a commitment to producing high-quality content for your paying audience. This might mean that you’re not able to create the same amount of free content to attract new fans anymore.

If you’re at an early stage of your career as a writer, you need to validate whether a paid newsletter is really worth the time and effort.

The only way to find a meaningful answer to that question is by analyzing some of the hard facts:

How often will you serve your paying audience?

At Write Your Future, we send a weekly written newsletter. Once per month, we record a roundtable session.

Even though most paid newsletters are delivered weekly, some creators serve their audience daily or monthly.

How much time do you need to create each letter?

As I’m collaborating with three other creators, I spend less than 30 minutes on each newsletter. Our goal is to deliver a 250-word answer per person to send a letter with a minimum of 1,000 words each week.

Depending on the type of content you want to share in your paid letter, the time you need for creation might be way more than 30 minutes.

At Write Your Future, most of our content is based on our experience and existing ideas, so none of us needs to research or spend time crafting ideas. All we do is share the valuable knowledge that’s already in our minds.

And last but not least: Explore the possibility of starting a joint-paid-newsletter just like we did with Write Your Future.

With tools like Substack, everyone can start a paid newsletter within just a few hours. But that doesn’t mean it’s going to be profitable and worth your time.

So make sure you take your time to answer the questions above and avoid starting an exclusive letter nobody is willing to pay for.

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