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Startup Execution Note: How to run a newsletter business

After 3 months of running a newsletter, I made my first $1000 in one day yesterday. These are my most valuable lessons learnt.

I turned on the "paid subscriber" option.

I recently moved over to Substack. I found my audience by Twitter and SEO. Mainly SEO through my own website and reposting that content on Medium.


The post

A Short Intro

I started the Signal with one goal in mind: To help entrepreneurs and young people start their own business. Am I the most qualified to do so? Hell no. But I have been down a path that a lot of people haven't, I thought sharing my learnings from that would be helpful. And it has.

The Signal gives you one business idea every week, with a game plan for how *I* would execute it.

Other features include:

  • 🚀 Startup Labs: A business idea explored

  • 🧨 Build-A-Business: The paid segment where we actually build a business. Launching 1st Tuesday of August.

  • 🎤 From the Founder's Mouth: Useful advice from people who have done it before.

  • 🛠️ Skill Builder: Every week I teach you one skill that every founder should have. (Landing Pages, Email Marketing etc.)

  • 📣 What's a Twitter: The most valuable Tweet (thread, normally) I came across that week.

  • 🖱️ Clickworthy: Useful resources, tools and info from around the web.

Start before you think you're ready

The format above is very different from what the first edition of the Signal looked like.

That's because I started way before I knew what I was doing. The first editions of the signal were quite bad.

But by starting early, I was able to solicit feedback early, and build something that resonated with my audience. I didn't spend a bunch of time building a product that no one wanted. I started with something small, and then built up the bits that people liked.

Set yourself a schedule

The first landing page for the Signal mentioned something about "Editions go out every so often".

Mistake. And I realized it quickly.

You have to be regular. Arrive in your readers' inboxes at the same time, on the same day every week (if weekly). It's also part of the dopamine loop. They get to know when your email is coming.

Collect feedback religiously

This helped me build a product people want.

Every single edition has three voting options at the end which looks like this:

👍 YES - I liked it〰️ MEH - Average👎 NO - Almost no value

They're links which I track in Google Analytics.

I also explicitly asked, begged and pleaded and sometimes manually emailed my early subscribers individually to ask them how I could improve and make the email the most valuable newsletter possible for them.

Don't get stuck on one idea

Founders often make the mistake of forming their product in their heads and then doing everything they can to build that.

That's not how great products are built.

Have the problem constantly in mind - not *your* solution to it.

Subject lines count

Every single one of my emails start with "⚡ Signal - ....".

That forms an important part of the dopamine cycle. When they get value from one email with a constant subject, the next time it pops up in their email feed, it becomes a priority. As that loop goes further, the bonds are made stronger and your open rates will continue to climb.

When I haven't spent enough time choosing the right subject line my open rates are definitely affected. Do it!

Write once, sell three times

Writing on the internet is extremely powerful. You're pulling a lever that let's you write for one hour, and have your writing be seen for thousands of hours (if you're good).

To make that happen, you have to sell yourself.

This is something I am bad at. I love product and I love writing and I HATE self promotion (Even writing this thread was a stretch for me). So selling is not my strong point.

But if you want your work to matter, you have to get it in front of eyeballs. Luckily, the internet enables that easily.

When growing/selling, remember: Give value first before expecting it in return.

When to monetize?

This was my strategy:

  1. Grow the newsletter ->

  2. Collect feedback to get to a product my readers loved ->

  3. Reinforce the value by delivering an excellent final product 8 weeks in a row ->

  4. Starting hinting at the idea of something beyond just content ->

  5. Started a community around my audience, limited applications ->

  6. Once I had a proven model and content, with a big enough audience ->

  7. Monetize through a paid extension.

Some comments on this:

  • I would never recommend asking users to pay from the beginning, unless you have an already established audience and message which simply needs to get converted over to the newsletter format.

  • When you go paid, don't reduce the content that you were originally providing, just add more for paid subscribers. That'll come across as a serious betrayal with your long-standing audience.

  • When people pay for something, they value it more. That's just the way it works. When you have something great, don't be scared to charge for it. If you've defined and tested your audience, and your content is *that* good, people will pay.

How to monetize?

There are a stack of ways to monetize a newsletter. Here are some off the top of my head:

  • Paid subscribers

  • Ads

  • Products

  • Affiliate Marketing

I don't like ads or affiliate marketing. Too much effort, too little return.

My philosophy is outlined in the last point of "When to monetize". I also like products, but those will come later.

Above all: Quality content

The one thing that is going to get people coming back time after time, is quality content. Put time and effort into making your newsletter great. Better than anything out there.

I spend roughly 5 to 6 hours a week (I work full time) on each newsletter. That's not counting promotion time and other admin-related stuff. That's all content time. Looking for ideas, organizing thoughts, collating links, writing drafts and then editing. All in all, its probably close to 10 hours a week.

That's about to double as I launch the paid Build-a-Business segment coming in August.

I see so many people putting a half-arsed effort into their newsletters only to wonder why their open rates are low, and subscriber numbers don't grow,

Bottom line: Give real value to capture and hold attention!


Growth Plan for the next $1000, $10 000 and beyond?

  • Focus on community. There will be a large focus on quality engagement in the Startup Labs community. Keeping it small will be essential. It will only ever be by invite and the maximum number of people will be 400. I've seen what too big of a group does to the dynamic.

  • Sustainable growth. I will continue to put content quality first, and growth second. Sure, I want to make money, but I also want to produce the best work I can for the people who have followed me. I'll do some promotion, but mainly rely on word of mouth. Essentially my marketing strategy is this:- Be the best- Rely on word of mouth

  • Key metrics: Open rate should stay above 50% (Currently 64% avg. across last four editions). Click rates above 30% (Currently 32.1% avg. across last four editions).

  • Quality content: I want to get to the stage where I can afford to pay someone (profitably) to build a list of content I can draw from.


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