The Complete Newsletter Guide: Positioning, Platforms, Growth, and Monetization, Lessons from 149 Issues

Oct 18, 2026 #電子報

A tree of readers growing beside a desk, its branches hung with envelopes and reader portraits

On September 14, 2022, I sent out issue No. 1 of the Vista newsletter. It was titled “Computers Can Sort Peanuts, and Now They Can Write, Too.” Yesterday, four years later, issue No. 149 went out, to 3.9 times as many subscribers as I started with.

Along the way I changed how I write, adjusted how often I send, built my own list system by hand, and made plenty of mistakes I’m still cleaning up. In this article I want to pull together what those four years taught me, along with success stories from newsletters in the West, Japan, and Korea, into a guide you can use even if you’re starting from zero. It follows the order in which a newsletter actually grows: first decide what to write, then pick a platform, then figure out how to get people to subscribe, and only then think about making money.

I’ll share real numbers wherever I can, including the unflattering ones.

Before getting into the how, I want to talk about the why.

I’ve been blogging for a long time. I’ve lived through all kinds of content platforms: Roodo, PIXNET, Wretch, Blogger, Facebook, Medium, Vocus, and more. Every time I moved platforms, I had to rebuild my readership from scratch. Every time an algorithm changed, my reach dropped again.

The moment it really hit home was on an international platform where I had built up a sizable following. One day I wanted to export my followers, and discovered the platform simply had no way to do it. Those people followed me, but I had no way to reach out to them myself.

AI search makes this even more urgent. A study Ahrefs published in February 2026 (opens in a new tab) found that when an AI Overview appears in search results, the click-through rate for the top-ranked page is 58% lower than it was at the end of 2023. More and more often, readers get their answer from the AI summary right on the results page and never click through to your site.

That’s why I think of my content assets in three layers. Social platforms are rented. My own website is semi-owned (the site is mine, but readers arrive through search engines, so part of that traffic is effectively rented). My email list is the only thing that is fully mine. My list system has a 98.2% delivery rate, and almost no social platform can promise to reach 98% of my followers.

That is the most fundamental reason to run a newsletter. Now let’s get practical.

Stage one: topic and positioning

Find a narrow enough audience first, then think about content

After studying dozens of successful newsletters, I noticed that nearly all of them share one trait: you can say in a single sentence who the newsletter is for.

Lenny’s Newsletter is written for product managers and covers the practice of product and growth. When Lenny Rachitsky first turned on paid subscriptions, he had roughly 15,000 free subscribers and 500 paying ones. Today, his site lists more than 1 million subscribers.
NEWNEEK (뉴닉) in Korea was founded in 2018 to explain current events to the MZ generation (a term coined in Korea that lumps Millennials, the “M generation,” together with Gen Z into one young demographic). It translates dense news into a voice young people actually want to read. By April 2024, it had passed 700,000 cumulative newsletter subscriptions.
UPPITY (어피티), also in Korea, targets young professionals in their twenties and early thirties and writes only about personal finance. According to its official partnership page, its 머니레터 (Money Letter) has 500,000 subscribers.
Ben Thompson started Stratechery in 2013, writing only about the business strategy of tech companies. In 2014 he launched a paid version and went full-time.

These four newsletters cover topics of very different breadth, but every one of them knows exactly who its readers are: product managers, the MZ generation, young professionals, people who care about tech strategy. When you know your readers, you know what to write about, and word of mouth knows where to travel.

Three positioning questions

I use three questions to check a newsletter’s positioning:

Who are your readers? You should be able to name a profession, an age range, or a life situation, not just “people interested in AI.”
What do they get from reading it? A time-saving roundup, a method they can actually use, or a perspective they can’t find anywhere else?
Why are you the one writing it? What experience, data, or vantage point do you have that others don’t?

The third question is the one people skip most often, and it matters most. Lenny was a product lead at Airbnb. Ben Thompson has hands-on experience at Apple and Microsoft. Readers trust that what they write comes from the front lines.

My data: the emails readers open most aren’t the ones they click most

After going through the performance of all 149 issues, I noticed an interesting split.

The issues with the highest open rates were almost all personal or newsy: No. 17, “Happy New Year, Happy Birthday,” and No. 26, the issue announcing my new book.

The issues with the most clicks were all hands-on topics: No. 109, “What Exactly Is Vibe Coding? Why Can Complete Beginners Build a Website?”; No. 117, which introduced an AI personality generator I built; and No. 98, about how AI is changing reading efficiency.

My takeaway: personal emails build relationships, practical emails drive action. A newsletter needs both. You just need to be clear about which job each issue is doing.

Frequency: send less rather than stop

I sent 35 issues in 2023, 25 in 2024, 27 in 2025, and 51 so far in 2026 through October. The pace has gone up and down, but in four years I’ve never stopped.

If you’re new, my advice is to commit to a frequency you’re confident you can keep, say, once every two weeks. Readers trust a biweekly newsletter that always shows up on time far more than a weekly one that comes and goes.

Every issue of my newsletter is a complete long-form piece of 2,500 to 5,000 words. I don’t write a teaser and ask readers to click through for the rest. To me, the email itself is the work. That’s my choice, and it won’t suit everyone. But whatever the length, make sure readers get the full value inside the email.

Stage two: choosing a platform

Check three things first: can you take your list with you, what’s the cut, and can you get paid

There are plenty of newsletter platforms out there, and comparison tables are everywhere. If you ask me, start with three questions:

Can you export your full list? This is the bare minimum. If you can export the email addresses, the list is yours.
How much does the platform take when you monetize? Once paid subscriptions grow, a difference of a few percentage points adds up to real money.
Can your readers actually pay you? Check whether the platform’s payment options can receive money in your region and whether your readers are used to them. Run a real test transaction before you launch.

Major platforms: who they suit and what they charge

Platform	Best for	Cut of paid subscriptions (per official public info)
Substack	People who want to focus on writing and grow through the platform’s recommendation network	10%, plus card processing fees
beehiiv	Operators who care about growth tools and ad revenue	0% platform fee (on paid plans), plus Stripe fees
Kit (formerly ConvertKit)	Creators with products to sell who need automated sequences	3.5% plus US$0.30
note (Japan)	Reaching Japanese readers with paid posts and memberships	10% for memberships and single posts, 20% for subscription magazines
theLetter (Japan)	Paid newsletters by professionals	17%, payment processing included
Self-built system	People who need segmentation and automation and have the technical skills	Only email delivery and payment processing costs

The fees in this table come from each platform’s official site. Please double-check before you launch, since rates can change at any time.

Two platform-scale numbers worth noting: in March 2025, Substack announced it had reached 5 million paid subscriptions (that’s subscriptions, not paying individuals). Japan’s note had 11.14 million members in fiscal 2025 and 2.02 million creators in total, and its top 1,000 creators averaged 15.15 million yen in annual sales.

My approach: two tracks in parallel

I run two systems side by side.

My main newsletter lives on Substack because it lets me focus on writing. I don’t have to worry about layout, unsubscribes, or archives, and nearly 20,000 readers are there.

The other is a list system I built myself on vista.tw. Emails go out through Resend, and the list sits in my own database. This system handles delivering free resources and segmenting readers. It currently holds nearly 5,000 unique readers.

The advantages of building your own are obvious. I can see which resource each reader signed up for, which page they came from, and whether they used a phone or a computer. When I was opening enrollment for my AI Academic Writing Workshop (opens in a new tab), I emailed only the people who had requested academic resources and left everyone else alone.

The cost is that you maintain it yourself. Over six months, this system took far more of my time than writing social posts did, and I hit plenty of technical potholes.

If you’re just starting out, I’d suggest using an off-the-shelf platform first. Once your list passes a thousand and you’re sure you want to segment readers and sell to them, then consider building your own or moving to a more full-featured platform.

Stage three: marketing and growth

Any discussion of newsletter growth eventually gets to Morning Brew. This daily business newsletter for young professionals is best known for its referral program: the more friends a reader gets to subscribe, the bigger the rewards. Its founders have told the press that the referral program significantly lowered their customer acquisition cost.

In October 2020, Insider acquired a majority stake in Morning Brew at a reported valuation of about US$75 million. At the time, the flagship newsletter had 2.5 million subscribers. By October 2024, it had passed 4 million subscribers, with an open rate above 50%.

Another example is Milk Road, a daily crypto newsletter. According to a case study published by beehiiv (beehiiv is the platform Milk Road uses, so it’s an interested party; take the numbers with a grain of salt), Milk Road launched in early 2022 and reached 250,000 subscribers in under 10 months. Its tactics included giving away PDFs for referrals, cross-promotions with other newsletters, and paid social ads.

A referral program only works if the content is worth sharing. If your readers don’t even open your emails, no amount of rewards will get them to spread the word.

Lead magnets: trade a free resource for an email address

My list system offers nineteen free resources on different topics. The sign-ups they brought in are wildly uneven: 2,688 came in during March alone, because that month I happened to get a burst of heavy exposure.

That taught me two things. First, a lead magnet doesn’t generate traffic on its own. Its only job is to turn traffic into subscribers. Second, growth tends to come in spikes. Instead of fretting over the numbers every day, put your energy into a few key bursts of exposure.

A few lessons from designing free resources:

Make sure people can actually reach the page. Some of my resources collected only a handful of sign-ups for a simple reason: nobody ever landed on that page. Right now I have only four entry points that work: the end of my articles, social posts, the newsletter itself, and the resource index page on my site.
Design for phones. 64.3% of my sign-ups were made on a phone. The form should be visible on the first screen, with as few fields as possible, and the resource you deliver should be readable on a phone too.
Make the button say what they’ll get. Write “Download this guide for free,” not “Submit.”
Add tracking parameters from day one. Some of my early sign-ups have no source tags, so I can’t accurately compare which channel worked best. It takes less than half an hour to set up, and if you skip it, that data is gone for good. This is the mistake I most want to warn you about.

The first email shapes everything after it

The first email after someone subscribes is the moment their attention is at its peak.

In its 2025 report (opens in a new tab), the Korean newsletter platform stibee analyzed 636,000 emails and found that automated emails (such as post-signup welcome emails and sequence emails) had 1.6 times the open rate of regular emails and 3.8 times the click-through rate.

This is an area where I haven’t done well enough. My list system’s delivery emails reach inboxes 98.2% of the time, but their open and click-through rates have fallen short of what I expected. That tells me the technical side is fine and the content side has a lot of room to improve. I’m rewriting my welcome sequence so the first email does more than drop a download link: it tells readers what’s coming next and why it’s worth opening.

Check your list’s health regularly

Beyond open rates, I look at three numbers every month:

Delivery rate: if it falls below 95%, find out why.
Bounce rate: a bounce rate above 3% means your list quality is deteriorating, and email providers will start downgrading your domain’s reputation.
Complaint rate: out of 7,927 emails, 1 was marked as spam. The lower this number, the better.

Stage four: monetization

Newsletter monetization falls roughly into four models.

1. Advertising and sponsorships

This is the route Morning Brew, The Hustle, and UPPITY have taken. With enough readers and a clear enough audience profile, brands will pay to reach them. The Hustle was acquired by HubSpot in February 2021, when it had more than 1.5 million subscribers; Axios, citing people familiar with the deal, put the price at about US$27 million. UPPITY’s partners include Samsung, Toss, and Korean government ministries.

The barrier for the ad model is scale. With only a few thousand readers, it’s hard to sustain a newsletter on advertising.

2. Paid subscriptions

Stratechery pioneered the paid newsletter: free weekly long-form articles bring readers in, and the paid Daily Update brings in revenue. By April 2015, Ben Thompson had more than 2,000 paying subscribers. Lenny’s Newsletter costs US$150 a year and includes annual subscriptions to a number of SaaS tools, so the value of paying is obvious at a glance.

Japan’s paid newsletter culture took shape even earlier. Takafumi Horie launched a paid メルマガ (email magazine) in 2010 for 840 yen a month. In its May 2025 earnings materials, the newsletter platform Mag2 (まぐまぐ) disclosed roughly 100,000 paying members, with paid membership in the finance category continuing to grow.

The key to paid subscriptions is making it crystal clear what readers get once they pay.

3. Selling your own products and services

This is my main model right now. My newsletter is completely free. I’ve turned on Substack’s paid features, but I haven’t officially launched a paid plan yet.

The real monetization happens downstream of the newsletter: workshops, courses, and books. Put simply, the newsletter’s job is to build trust, and the products’ job is to bring in revenue.

This is where segmentation really matters. Without segments, if I only looked at the average conversion rate across my whole list, I’d never discover which group of readers needs what I offer most.

4. Getting acquired

Morning Brew and The Hustle both got here. It’s more an outcome of success than a sensible goal to start with, so I’ll just mention it in passing.

A monetization sequence for beginners

If you’re just getting started, here’s the order I’d suggest:

Your first 1,000 readers: focus on writing and on reading your readers’ replies. Don’t rush to charge money.
Once you know what your readers care about most: launch a small product, such as an online talk, a template, or an ebook, to test whether they’re willing to pay.
Once readers have shown they’ll pay you: then decide whether to go with paid subscriptions, courses, or advertising.

An action checklist you can follow

Week one

Write one sentence each on who your readers are, what they get, and why you’re the one writing.
Pick a platform, and confirm you can export your list and actually receive payments.
Settle on a frequency you can sustain.

First month

Write a welcome email that tells new readers what they’ll be getting.
Add a subscribe prompt at the end of every article.
Add tracking parameters to every subscribe link.
Go through the whole sign-up flow yourself on your own phone.

First three months

Create a free resource closely tied to your topic.
Check your delivery rate, bounce rate, and complaint rate every month.
Find one or two newsletters with a similar audience and talk about cross-promotion.

After six months

Segment readers by interest.
Launch your first small product and see which group of readers is most willing to pay.

If you’re planning to start a newsletter, or you’ve been writing for a while and are stuck on growth and monetization, you’re welcome to book a one-on-one 60-minute AI consultation (opens in a new tab). We can look at your positioning, platform choice, and list design together, and talk about how to use AI to make writing a newsletter less of a grind.

Final thoughts

After four years and 149 issues, my biggest realization is this: a newsletter isn’t a traffic tool, it’s a relationship.

Social platforms will change their algorithms, and search engines will be intercepted by AI summaries, but as long as you hit send, your email lands in your readers’ inboxes. That’s one of the few places that still belongs to creators themselves.

If you’re thinking about starting a newsletter too, feel free to subscribe to the Vista Newsletter (opens in a new tab) and see how the practices in this guide work in real life.

References

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Vista Cheng speaks and runs workshops on AI workflows, writing and content systems for companies, schools and public agencies.

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The Complete Newsletter Guide: Positioning, Platforms, Growth, and Monetization, Lessons from 149 Issues

Stage one: topic and positioning