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How to Kickstart and Scale a Million Dollar Newsletter Business: Part 1

Finding an idea and getting your first 1,000 users

Hey everyone 👋! I’ve been spending a lot of time working on this new series where I deep-dive into some interesting business trends. I’d love to hear what you guys think at the end!

Newsletters are becoming one of the biggest trends for entrepreneurs.

Platforms such as Substack make it easier than ever to start, promote, and monetize a newsletter - paying over $300 million to writers cumulatively.

Some recent newsletter successes include:

  1. Morning Brew selling a majority stake to Business Insider valuing at $75 million.

  2. Daniella Pierson turned a dorm-room project, The Newsette, into a media company generating over $40M/year.

  3. The Hustle sold to Hubspot for tens of millions of dollars.

But how did these newsletters grow to a nearly 9-figure business? How did they get their initial users? Monetize? Or even come up with the idea?

I’ve spent the last few weeks studying some of the largest and most successful newsletters to provide a roadmap on how they went from 0 → 1. Hopefully, you’ll gain insights, stories, or frameworks that you can apply to yourself.

In this two-part series, we’ll focus on the following roadmap.

Part 1: ← This Part

  1. How to come up with a newsletter idea

  2. Building an MVP: Picking an email platform

  3. How to find your early users

Part 2:

  1. How the most successful newsletters scaled to 7-figures

  2. Pricing paid newsletters and monetization

  3. Consistent content distribution

  4. How to apply AI to your newsletter workflow

Let’s get started!

STEP 1. How to come up with a newsletter idea

After researching some of the most successful newsletters, I’ve noticed a few common strategies for developing a good newsletter idea.

  1. Follow your own curiosity

  2. Filling a gap in the market

  3. Share practical expertise

  4. Doubling down on what already works

  5. Pick an underrepresented niche

Follow Your Own Curiosity and Interests

One of the best ways to find an excellent newsletter idea is to follow your own curiosity and interests since it’s likely many others will too.

Packy McCormick of Not Boring

And what I really loved writing about recently is business strategy companies, companies big, small, and mixing that with finance.

So I’m just trying to you know, make it approachable, fun, and enjoyable while you’re learning something.

Packy McCormick on The Nathan Barry Show

Examples:

  • Not Boring: Packy McCormick began publicly sharing his research and deep dive into tech startups with a mix of business strategy and humor.

  • Stratechery: Ben Thompson used his love of tech, product, and historical media news to draw insights and similarities, such as Disney’s Taylor Swift Era.

  • Scott’s Cheap Flights (Going): Scott Keyes was obsessed with finding travel deals and began sending them out to a group of friends.

  • Starter Story: Pat Walls turned his interest in building online businesses into an “entrepreneurship interview site and newsletter”.

  • The Generalist: Mario Gabriele used his passion for writing and combined it with his interests in tech products, founders, and venture capital.

  • HNGRY: Matt Newberg’s infatuation with Ghost Kitchens eventually led to him creating a newsletter highlighting the global food tech revolution.

  • TrendsVC: Dru Riley found himself loving to research business trends while building out SaaS products

  • World Builders: Nathan Baugh combined his passion for writing fantasy novels and engineering to provide storytelling lessons from a unique lens.

  • The Bear Cave: Edwin Dorsey started his newsletter to help him get a job as a hedge fund analyst, focusing on areas of interest such as SEC enforcement actions, company misconduct, and information related to short sellers.

Some general advice and patterns these newsletters follow:

  1. Write what you’re passionate about. You’ll likely “differentiate” yourself from your writing tone or the unique perspective you can bring.

  2. Quality is key. Most of these newsletters are not daily. A lot of time, effort, and research goes into each piece.

Make information more easily accessible

Some of the largest and most profitable newsletters were started by fulfilling gaps in current media.

Morning Brew became the go-to news outlet for millennials and college students and recently sold for $75 million, while TheSkimm has an estimated revenue in the tens of millions.

The Gist co-founders Ellen Hyslop, Roslyn McLarty, and Jacie Dehoop via Forbes

Sports can really feel like a boys’ club.

We wanted to create a female voice in sport that was specifically for a female audience.

The Gist Cofounders Jacie, Ellen, and Roslyn

Examples:

  • Morning Brew: Alex Lieberman felt that traditional business news like the WSJ was too dense for the average college student and started Morning Brew as a witty alternative.

  • The Skimm: Carly Zakin and Danielle Weisberg felt that there were very few dedicated media outlets exclusively targeting young millennial women.

  • The Browser: Robert Cotrell was previously a journalist at The Economist and realized there was a lot of clutter around the internet. He started The Browser to highlight 5 pieces of good writing and why it’s worth the reader’s time and has value.

  • Bankless: Ryan Sean Adams started Bankless with the idea to help onboard billions of people into a new technology: crypto.

  • The Hustle: Sam Parr originally grew a large email list from a speaker conference catered towards non-tech founders, eventually, he ditched the conference and began to write content catered towards this same audience.

  • The Gist: Jacie deHoop, Ellen Hyslop, and Roslyn McLarty felt the Toronto sports scene lacked attention and celebration for women, so they started The Gist to provide a female voice in sports specifically for women.

  • Tangle: Isaac Saul was a political reporter who realized people trusted information based on the newsletter outlet, not the content itself. This led him to start Tangle, which focused on providing independent and non-partisan news.

  • Future Party: Boye Fajinmi was hosting events and house parties in LA when he felt there was a lack of information surrounding the millennial pop and entertainment culture in LA.

General questions and things to think about for these newsletters:

  1. Look for problems in the media around you. Most of these newsletters took an existing problem in media and “disrupted it”.

  2. Write consistently. If you want to make information accessible, people need to trust it. Most of these newsletters immediately started with a daily or thrice-a-week cadence.

Share Practical Expertise

A simple way to begin writing a newsletter is to share areas of information you have knowledge and expertise in.

This could range anywhere from getting promoted quickly in tech, a morning productivity hack, or even cooking recipes.

Lenny Rachitsky, creator of Lenny’s Newsletter

But what started happening is I first started collecting my thoughts of what I learned at AirBnB and things I’ve done in the past

…It is more of a playground of collecting things that I’ve learned that I wanted to crystalize.

Lenny Rachitsky on The Nathan Barry Show

Examples:

  • Lenny’s Newsletter: Lenny Rachitsky shares a weekly advice column with lessons from his past experiences starting a company and leading product at AirBnB.

  • The Pragmatic Engineer: Gergely Orosz failed to find a weekly publication to help him grow as an engineering manager at Uber. Now he “writes the publication he wishes he had”.

  • Saturday Solopreneur: Justin Welsh shares advice on monetizing a one-person business and building productive content systems.

  • Every (Superorganizers): Dan and Nathan started their bundle of newsletters with the idea of giving productivity advice and systems from experts.

  • ByteByte Go: Alex Xu and Sahn Lam wanted to help engineers improve their system design and interview skills

  • DTC Branding: Nik Sharma shares his vast experience and insights working with DTC brands such as Hint and Cuyana to help DTC marketers.

  • What to Cook When You Don’t Feel Like Cooking: Caroline Chambers turned her failed cookbook launch into a weekly Sunday recipe

  • ParentData: Emily Oster gives all the numbers and decision-making tools for anyone who wants to be a parent, plans to become one, or already is.

  • Technically: Justin started his newsletter to help non-technical people understand complex software engineering topics.

General thoughts surrounding practical newsletters:

  1. Interview Style Newsletters are becoming more popular. Utilize guest posts to bring more of a unique perspective.

  2. Try sharing your expertise even if it has failed in a different medium. Newsletters are a new way of digesting information. Several writers turned their failed podcasts, books, or YouTube channels into successful newsletters.

Doubling Down On What Already Works

Another popular way to begin a newsletter is to follow what already is working. This could be a few things:

  1. Following the playbook of an already successful newsletter

  2. Convert an existing product into a newsletter

  3. Capitalizing on popular trends such as crypto and AI that dominate social media channels

Shaan Puri from the Milk Road

Inspired by my buddy Sam Parr who I got to watch step-by-step build The Hustle from scratch over several years

I felt like I could copy+pasta his blueprint, but for crypto

Shaan Puri on LinkedIn

Examples:

  • Milk Road: Shaan Puri took an effective “blueprint” from his podcast host Sam Parr (who built and sold The Hustle) and applied it to crypto.

  • TLDR: Dan Ni was inspired by many newsletters back in 2018 to build out his collection of curated newsletters (tech, crypto, AI, sales, etc).

  • The Daily Upside: Patrick Trousdale used the success of both Morning Brew and The Hustle to create a newsletter catered towards investors instead of general business and finance.

  • The Neuron: Pete Huang was building out a large AI audience on LinkedIn when he learned about the Milk Road acquisition. Motivated by this, Pete launched an AI newsletter on the same platform.

  • The Peak: Brett Chang built “Morning Brew for Canada” and even used similar growth strategies such as referral programs and campus ambassadors.

  • The Morning Huddle: Jake Robinson combined his love of Morning Brew and Fantasy Football to create a daily newsletter of all things fantasy football

  • Indie Hackers: Courtland Allen took inspiration from success stories on Hacker News from online builders and built a community platform which he sold to Stripe.

  • TheDrop: Gannon Breslin was writing a finance newsletter when the NFT/Crypto wave came in early 2021. Realizing this was the new “hot thing” and no one was writing about it, Gannon quickly pivoted.

  • The Publish Press: Colin and Samir used their experience as popular YouTube creators to provide an inside look at the creator economy.

Thoughts and takeaways:

  1. Imitate the success of others. There’s room for a popular podcast, YouTube channel, or subreddit to also be a newsletter.

  2. Keep up with the latest trends and ride that success. Many of the popular AI newsletters and creators used to be in crypto too.

Niche Down

The last main strategy I’ve seen is focusing on a specific niche.

While the audience for this might not be as large as something like Morning Brew, there is far less saturation.

I landed on a simple golf newsletter. The newsletter would have the busy professional in mind

The overall goal, to make following golf easy and stress-free for fans.

Andy Johnson of The Fried Egg

Examples:

  • A Continuous Lean: Michael Williams published his newsletter to focus on all things menswear and luxury.

  • Payload: Mo Islam wanted to help readers better understand the public and private players in the space economy.

  • Soft Launch London: Jimmy Richardson wanted to find out the best restaurant deals around London, typically around “soft launches”.

  • Fried Egg Newsletter: Andy Johnson wanted to make following golf fun for the busy, everyday professional.

  • Extra Focus: Every week, Jesse Anderson shares thoughts and strategies for dealing with ADHD

  • The Alerts Daily: LeQwane Lynch started a newsletter for sneaker collectors and resellers.

  • Paris by Mouth: Meg Zimbeck had the goal of helping everyone find delicious local restaurants in Paris.

  • Flow State: Each day, discover two hours of music that is perfect for working.

  • Inverse Cramer: Tracking Jim Cramer’s stock picks and fund performance.

Takeaways from niche newsletters:

  1. Follow real-life experience. Look at the things you think about and participate in day-to-day. Some of the largest niche newsletters take a broad problem (finding good restaurants) and localize it (the city they live in).

  2. Find your ideal audience. Figure out what is the ideal audience for your niche. Where do they exist? How can you get your content to them?

  3. Don’t get “too niche”. You want some flexibility in the topics you’ll write about or else you’ll eventually get bored and burn out.

STEP 2: Picking a Newsletter Platform

For most people trying to start a newsletter, I think there are three viable platforms to use: Ghost, Substack, and Beehiiv. Here’s what I gathered regarding the pros and cons of each:

A fourth option that you could consider is a ConvertKit, but this is generally if you are an existing creator with a book, info product, or course you also want to sell.

Substack

Editing on Substack

Substack has been a recent industry favorite for independent writing and is something you can set up in a single afternoon.

Despite taking a 10% cut for paid subscribers, they host some of the largest paid newsletter publications in the world that easily make six figures a month.

Their strongest feature is their amazing growth and social levers. Top leaderboards, built-in newsletter search and recommendations, and mentions are all features that will automatically drive readers to your newsletter.

78% of new subscribers are now coming from other Substack newsletters recommending my newsletter. And 11% of paid.

Game changing feature.

Lenny Rachitsky when hitting 250,000 subscribers

On the downside, they have the least amount of customization available and a fairly limited editor compared to Ghost and Beehiiv.

The biggest potential platform risk is that they host many free newsletters while only generating revenue for paid newsletters, a pricing model that may be forced to change in the future.

Beehiiv

A markup of Beehiivs’s editor

Beehiiv’s the new kid on the block. It was started by early Morning Brew employees and they’ve shipped an incredible amount of features in just a few years.

Similar to Substack, this newsletter can be set up in a single afternoon.

They take no fees for paid newsletters, and customizable landing pages, and give a variety of monetization and growth tools for you (finding ad sponsors, paying for recommending other newsletters, etc).

The biggest pain point is that they don’t have the discovery, brand reputation, and diverse user base of Substack or ConvertKit yet.

Fun fact: This newsletter is powered by Beehiiv.

Ghost

Ghost’s powerful editor

Ghost is a special platform compared to Beehiiv and Substack. They started as a WordPress alternative, so many of their core features are optimized for the web.

With a standard theme much similar to Medium, Ghost has without a doubt the best design out of the three. You can choose custom themes or even build a custom newsletter because it’s all open-sourced.

For people who are trying to optimize both web and email or want to build a membership site, this is the premier option.

Ghost is just implausibly good. It takes care of everything you need out of the box - email sending, payments, website. Everything

Uri Bram, The Browser

On the downside, they lack a lot of newsletter-specific and growth tools that Substack and Beehiiv use. You also have to pay quite a bit more unless you host your website on your own server, but this is quite troublesome.

STEP 3. How to get your first 1,000 users

How did the largest newsletters go from initial idea → MVP → to content that is read by 10, 100, or even 1000 people?

While there is no direct answer that can work for you, I’ve gathered the most common (and often unscalable) ways the largest newsletters got their first 1,000 readers:

  1. Utilize your personal network

  2. Leverage the audience of influencers and guests

  3. Share with social forums and networks

  4. Find your users directly

Utilize your personal network

The first way to get your first 1,000 subscribers is to use your personal network of friends, families, and other people you engage with frequently.

It sounds simple, but it’s a great way to validate your idea, gather feedback, and obtain high-quality subscribers. The most engaged subscribers will also often share your newsletter with their network as well.

Some stories you can draw inspiration from:

Tangle

Every newsletter that went out, I asked readers to share Tangle on social media or forward the email to five friends.

I used my personal Twitter and my communities (I played ultimate Frisbee so I sent the newsletter to many players in that community) to leverage new sign-ups.

Isaac Saul on reaching 1,000 subscribers via Indie Hackers

Building A Second Brain

If I had coffee with someone, the last thing I asked, can I add you to my email list? If I met them on the subway, it was like one name and email address at a time.

Because I knew there wasn’t much traffic to my website. People weren’t going to sign up just because.

I was really religious about getting people on there

Tiago Forte on The Nathan Barry Show

The Profile

Source: The Profile

In the very early days, you can increase your luck just by telling people what you’re working on.

Tell people about what you’re writing. And ask your early readers for help. In the early days, I would tell my readers, ‘Hey everyone, here’s what I’m working on, I’m trying to grow this to 1,000 readers. I would really appreciate it if you would tweet The Profile.’

You’d be surprised by how many people are actually willing to help.

Polina Pompliano on The Newsletter Crew

The Bear Cave

I spent three days. My eyes started to hurt. Just DMing every Twitter follower being like sign up for this newsletter, please!

That’s what built early momentum. I clawed my way to 3,000 free subscribers.

Edwin Dorsey via GrowthInReverse

The Fried Egg

I sent that newsletter to 10 people — 10 friends and families that really liked golf. Everybody liked it.

For my next newsletter, I scoured my inbox, and I found 200 people that I’d played golf with. And I sent them a note telling them what I was doing.

And it was really positive. Every time I sent a new newsletter, more people were on the list than the last time.

Friday Forward

A few years back, I decided to e-mail my Acceleration Partners team each Friday morning with a leadership theme, quote, and related tip/artcile around personal growth.

The response was overwhelming positive and employees told me they looked forward to it each Friday and “forwarded” it regularly to family and friends.

Leverage the audience of others

The second strategy you can use to grow your newsletter is to actually leverage the audience of other people.

This usually happens in a few main ways:

  • Interview-style newsletters or deep dives on individuals have an inherent growth engine, as they will likely share your piece with their audience.

  • Quality writing will catch the eyes of prominent “influencers” in your niche, which will boost your reach

  • Guest post, collab, or perform an interview with other blogs, podcasts, and social channels with similar audiences

Lenny’s Newsletter

Phase one was just writing a few things that people seem to like, but really maybe my first thousand subscribers, they came from two guest posts.

I wrote a guest post on the First Round Review, which happened to be a similar audience to my newsletter. And I wrote a guest post on Andrew Chen's blog who's now a partner at Andreessen Horowitz.

He's a longtime kind of growth mind and so I was working on some, I showed it to him and he's like, "Hey, I want to write... I want to have this in my newsletter."

Lenny Rachitsky in Entrepreneur

Stratechery

Source: Vox Media

There's a John Gruber connection here as well; I emailed him to thank him for the inspirational email, and naturally included a link to Stratechery.

Sure enough, he not only linked to Stratechery but spent an entire paragraph in a full-length post praising Stratechery and calling it the best new blog of the year.

That’s when things really took off.

The Skimm

We also emailed every news anchor Most of them didn’t respond.

Hoda Kotb responded and said, “I’ll check it out, sounds great”. We followed up two more times no response. day 4 of us in business, she said we were one of her favorite things on air and it totally changed our life.

It crashed our site and we got a couple thousand subscribers.

She put us on the map and we suddenly had geographic diversity.

Scotts Cheap Flights (Going)

I had a friend of mine who worked at Business Insider, saw this and was, like, “Oh that looks like an interesting story. Hey Scott, can I pass this along to my friend here who writes about travel for Business Insider”

The day we left for this big trip, the Business Insider article went up.

It ended up going super viral, 250, 300, or 400,000 clicks on it.

So literally overnight it went from this just sleepy little hobby for 300, 400 people, 80% of whom I knew personally, to 5,000 subscribers. Like overnight.

Scott Keyes on IndieHackers

Superorganizers (Every)

For example, the interview model works really well. And I would extend that to involving other people in your newsletter.

So for me, I interviewed someone every week. Often that person has an audience, and in the interview, they get to share all this stuff that they’ve never gotten to share before.

So I have this built-in growth engine where every single week someone is tweeting it out. So you just stack that growth week after week after week and you can climb the ladder of influence.

Rad Reads

I think, so there were a few key moments and they were all driven by press and partnerships. None of it was targeted.

The biggest two were CNN wrote an article about me called calling me Oprah for millennials on New Year’s Eve of 2016. And they kept it on the front page of CNN Money for three days.

So that took me probably from like, Four to 2000 to 10,000.

those all came from the reporters being subscribed to the newsletter

Technically

IBM’s new sales director recommended Technically at a conference for IBM’s entire sales team, and that added something like 4,000 free subscribers in a week.

Earlier on, friends of mine (shoutout to Shomik Ghosh) shared on their accounts, and that led to big bumps. So there have been big moments where someone of consequence shared the newsletter and it led to a huge jump in subscribers

Share with social forums and networks

The third strategy is to share with social forums and networks. Specifically, most creators use this strategy to:

  • Create viral pieces of content (social sharing is very strong)

  • Bring you a targeted audience from FB Groups, Reddit, etc

Starter Story

I realized I needed a distribution channel. I tried a lot of things and finally found something that worked.

Posting the case studies on Reddit,

My first success hit the top of r/Entrepreneur and it validated that our case studies with founders were actually interesting and valuable to Redditors.

Besides its huge reach, these Reddit posts also helped us find our first “sponsors” and more businesses to interview on the site.

What to Cook When You Don’t Feel Like Cooking

Source: Edible Monterey Bay

I began cranking out free content via my Instagram and my newsletter. I was able to grow my following on Instagram pretty quickly.

Before I hit 10k Instagram followers and got the “swipe up” option, I would leave a “question box” on my Instagram stories and let people write their email, which I would manually add to my newsletter list.

It was laborious, but totally worth it.

The Hustle

My first email drip, I actually show all the stats to the websites.

Right away we were getting thousands of people to come to the website because I got really good at posting it on Reddit and HackerNews.

Marketing Examples

I found all the places where marketers hang out and thought how could I add value directly to these platforms.

I would write these articles on my website, on Twitter threads, on Reddit, different subreddits like r/Entrepreneur, then on Indie Hackers, on Facebook Groups, literally everywhere I would just put the article.

First 1000

What worked for me to go from 100 → 1000. The first thing was a second HackerNews feature.

The second thing that worked really well for me was Twitter. Primarily three tweets.

TLDR

This one is a bit different. Dan Ni ran paid social media ads instead of strictly posting on Reddit and Quora, but I think his strategy and reasoning are extremely helpful.

Starting out, I spent about $50 a day running ads to get the ball rolling with some subscribers.

I found that it’s really important to keep the growth momentum up in order to stay motivated with any project.

I started running ads in places like Reddit (10 cents per click for any geo and topic) and Quora (you can pick individual questions you want to run ads on).

World Builders

Twitter threads are my number one driver for growth. I do one per week.

I just crossed 11,000 subscribers and I’d say that Twitter threads are probably responsible for 9,000.

Find your users directly

The last strategy is to find your users directly. This often means:

  1. Hosting events or parties with your target audience

  2. Find large clubs or communities where they congregate

  3. Reach out to strangers directly

Morning Brew

We were students at the University of Michigan at the time, and knew many business lectures had 400+ students. We spent weeks asking professors if we could speak in their econ/accounting/finance 101 classes.

We decided that if people weren't going to go and sign up themselves, we had to do it for them.

After we pitched a lecture, we'd pass around pieces of paper for everyone to write down their email. We then asked ourselves: "What if we can did this on every campus across the country?"

The Newsette

Source: Career Contessa

So, I would go into Facebook and I would find all of the people that I went to high school with who I hadn’t talked to in years

I would then click on their profile and see all of their new friends from their new colleges and I would message all of the girls being like, ‘Hey, I work for this really cool newsletter company. If you become an ambassador, you can put it on your resume.

So that’s really how I started getting my first, you know, couple of hundred and then a thousand subscribers

And then really from there, I just used word of mouth from the people that were subscribing

The Gist

So we initially started off again centered around Toronto, so a Canadian newsletter, but then Toronto newsletter, all of us at that time, I think were 25. And we thought what better way to get subscribers that have a party.

And so we partnered up with Shopify. Actually, they have a beautiful office in Toronto. We knew some folks there. They allowed us to rent out their space for free.

We had partners like Lululemon and TFC come on board to do, swag bags for everyone

Ellen Hyslop

The Generalist

Early on I reached out to several collegiate VC Clubs since I thought MBA students would enjoy it.

One time I messaged the Head of the VC Club at Wharton and said, “Hey, some of your members have signed up for The Generalist, just wanting to share it with you and see if it might be something you'd be down to share with your cohort.”

Mario Gabriele on IndieHackers

The Future Party

We just saw an opportunity to create a community for like-minded folks who had come to LA to live that Hollywood dream.

So we started throwing parties to celebrate that ambition.

I’m super happy that at one point we were like “let’s collect emails”. I don’t think we knew the value at the time, but we would have a relationship with our community between events.

So we started with the newsletter with a few thousand subscribers.

Payload

Ari Lewis, the co-founder of PayLoad said he would use LinkedIn's advanced search and find individuals on LinkedIn who worked in the space industry.

He would then DM them personally and tell them about PayLoad and shoot them over the link to subscribe if they were interested.

He used this exact tactic to get hundreds of new, and interested subscribers for PayLoad.

Alex Garcia on Marketing Examined

We formulated our idea, shipped out our MVP, and even got our first 1,000 users.

But how do we take this side project and turn it into a full-fledged business?

We’ll focus on this very exact thing NEXT week in the final part of this two-part series.

Subscribe to make sure you don’t miss it!

On another note, I’ve been thinking about being purely reader-supported for quite some time now. If you’ve got this far, please reply to this email or post if this type of content is something you’d pay for.

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