Category: Getting started

Step-by-step guides for new newsletter operators.

  • How to start an email newsletter in 2026 — without giving the platform a 10% cut

    How to start an email newsletter in 2026 — without giving the platform a 10% cut

    Last week Ali Abdaal published a 14-minute video called How to Start an Email Newsletter. It is a good primer: why a newsletter is the easiest creator project to start, what to write about when you have no idea what to write about, and a three-platform walkthrough at the end (ConvertKit, Revue, Substack).

    The first two-thirds hold up perfectly. The third-act platform recommendation is where we want to add something. Revue closed in 2023. Substack still works but it owns the relationship between you and the people who read your writing. There is a better default in 2026: write the newsletter on your own WordPress site using a free plugin, and you keep the subscriber list, the email addresses, the design, and the URL forever — even if you change tools next year.

    This is that walkthrough.

    Part 1: Why you might want a newsletter in the first place

    Ali makes five arguments, and they all stand up:

    It is free to start. Unlike a YouTube channel — which needs at least a phone, decent lighting, and the courage to film yourself talking to no one — a newsletter is just an email. You type, you send. There is no production setup.

    It is low-friction. Most people who freeze when starting a creator project freeze because the first step is hard. With a newsletter the first step is “write a paragraph and click send”. If you can write a long text message you can write a newsletter.

    It is private until you want it to be public. There is no algorithm pushing your newsletter into anyone’s feed. Your first ten issues can go to your mum and one friend and that is fine. You get to practice the craft of writing for an audience before there actually is an audience. YouTube does not give you that grace period.

    You own the audience. An email address is the closest thing the internet has to a direct line. The reader has explicitly given you permission to show up in their inbox, and you can unsubscribe with one click — which means anyone who stays is choosing to be there every single week. That is much more valuable than a follower count on a platform that can change its algorithm tomorrow and bury your work.

    It can become an asset. Ali wrote his Sunday Snippets newsletter for three and a half years before he made any direct money from it. Now individual sponsor slots go for $5,000–$7,000. Morning Brew started as a daily email written by Alex Lieberman in his university dorm room; five years later he sold it for $70 million. The point is not that your newsletter will sell for $70 million. The point is that a newsletter that nobody pays for today can quietly become a real business in three years, without you having to bet your career on it now.

    Part 2: What to write about (or: the only question that actually stops people)

    The wall most people hit is not “I do not know how to type”. It is “I do not know what I would even write about”. Three responses to that:

    Write about whatever you find interesting. If you genuinely enjoy writing Harry Potter fanfiction, write three paragraphs of Harry Potter fanfiction every Sunday. The reason this matters is not the topic — it is that intrinsic motivation is the only thing that keeps you consistent in the first year, when nobody is reading. Consistency is the secret. If you are doing it for the love of the craft, you keep going. If you are doing it for the money, you quit when the money does not appear by month three.

    Curate. Tim Ferriss runs one of the largest newsletters in the world — Five Bullet Friday — and the entire format is “five things I enjoyed this week”. A book, a podcast, a gadget, an article. You almost certainly consume stuff during the week that other people would benefit from. Send them a list.

    Pick a topic. Morning Brew is just “what’s happening in business and tech, told entertainingly, every weekday morning”. If you are genuinely interested in something, there are almost certainly other people who would like to be kept up to date on it without having to find the sources themselves.

    All three work. None of them require you to be an expert. They require you to write the thing every week.

    Part 3: How to actually start one — without giving the platform a permanent cut

    Here is where we depart from Ali’s video. He recommends Substack as the default for someone starting from scratch. Substack is fine for a first draft, but it has two long-term problems:

    • 10% of every subscription, forever. The moment your newsletter starts making money, Substack takes 10% off the top. On a healthy paid newsletter that is real money — a thousand subscribers at $8/month is $9,600 a year going to a platform you do not need by year two.
    • It is their URL, their design, their brand. Your newsletter lives at yourname.substack.com with their header, their fonts, their suggested-newsletters block at the bottom of every email. Migrating off later is possible — but you lose a lot of the SEO and brand equity you have built.

    The alternative: run your newsletter from a WordPress site you already own, with a plugin called One Two Three Send. Free, no revenue share, no platform lock-in, no algorithm-driven sidebar. Your domain, your design, your subscriber list — yours in the literal sense that they live in a database table on your own host.

    Five minutes from zero to a sent newsletter

    1. Install the free plugin. WordPress admin → Plugins → Add New → search “One Two Three Send” → Install → Activate. Or grab it directly from wordpress.org/plugins/one-two-three-send.
    2. Pick how emails actually get sent. Newsletter → Settings → Email Provider. Resend (free for first 3,000 emails/month, simple API key paste) or SMTP (any provider including Amazon SES, MailerLite, Brevo, Mailchimp). Pick one, paste credentials, save.
    3. Drop a signup form somewhere. Newsletter → Signup Forms gives you a default form on first activation. Embed it on your homepage with

      The newsletter for newsletter operators

      Daily field notes on deliverability, AI tools, hosting, and monetisation. No "top 10 plugins" filler — real tools, real numbers, real failures.

      , or use the Gutenberg block. Done.
    4. Write the first issue. Newsletter → New Newsletter. Type something. Click Run audit (the plugin checks the obvious mistakes — missing unsubscribe link, dodgy subject line length, broken placeholders, spam triggers). Click Send.
    5. Your first subscriber is you. Add your own email through the Subscribers tab so you can see what arrives. Send the first issue. Open it. Forward it to your mum.

    That is the entire free plugin. It is enough to run a real newsletter for as long as you want. The whole “I do not know what platform to start on” friction goes away because you are writing inside the same WordPress admin you would use to write blog posts.

    When you outgrow the free tier

    Ali talks about the moment a newsletter starts to make money — sponsors, a course, a paid tier. That is the moment Substack quietly starts charging you 10%. With One Two Three Send the upgrade path is a companion plugin called One Two Three Send Pro, distributed to subscribers of our own newsletter. What it adds maps directly to the use cases Ali mentions in the video:

    • Stripe paywalls for paid subscribers, with no revenue share to anyone. You set the prices, Stripe charges, the money goes to your bank account. We see the metadata to flip the free/paid flag on a subscriber row; we never see the payment itself.
    • AI newsletter generator using your own Claude API key. This is the practical answer to “what should I write about this week” — Claude drafts from your site’s recent posts, your tagline, and a manual description of your voice. You edit. You send. The cost per issue is a few cents of Claude tokens, paid directly to Anthropic.
    • Welcome email + lead magnet delivery on every signup, completely automatic. A new subscriber gets a personalised “thanks for signing up, here is your free PDF” email within seconds of the form submission.
    • More email providers — Mailchimp, MailerLite, Brevo, ConvertKit, Amazon SES on top of Resend and SMTP. Pick the one your audience already trusts.
    • Newsletter Network — opt-in cross-promotion ring of other One Two Three Send sites. Drop a small widget on your blog posts, your readers see other newsletters, their readers see yours. It is the closest thing to an algorithm a self-hosted newsletter has, and it costs you nothing except the screen space at the bottom of a blog post.
    • Pre-send audit with five extra Claude-powered checks on top of the free plugin’s ten — tone match, opening hook, structure, call-to-action strength, subject-vs-body alignment. Catches the issues that make sends embarrassing in retrospect.

    The pricing model for Pro is intentionally simple: it is bundled with the paid tier of the publication you are reading right now, so there is no separate marketplace, no separate licence key, no separate billing. See pricing if you are curious.

    The honest summary

    Ali’s video is right about the why and right about the what. The free plugin we make is just a different answer to the how — one where the subscriber list, the URL, the design, and the future revenue all belong to you, and the only thing we ever bill you for is the optional Pro upgrade that does not change who owns the relationship.

    If you watched the video and felt the itch to start, do not over-think the platform decision. You can start on Substack tonight and migrate later if it works out — we have a CSV-import path that takes ten minutes. Or you can start on your own WordPress site tonight and skip the migration entirely. Either way, the part that matters is writing the first issue this week.

    Hit reply on any of our issues once you have sent yours. We read every one.

    Heads up — some links in this article are affiliate links. If you sign up through them, we may earn a small commission at no extra cost to you. We only recommend tools we use ourselves.

  • The host that fixed our site at 11pm on a Sunday

    The host that fixed our site at 11pm on a Sunday

    TL;DR. BigScoots is a managed-WordPress host with the kind of proactive support most hosts only put in their marketing copy. We use them on every site we run.

    What is BigScoots?

    BigScoots is a US-based managed WordPress and managed VPS host. They’ve been around since 2010 — old enough to know what they’re doing, small enough that the support team actually knows your site by name.

    The pitch is simple: hosting that’s genuinely fast, with a 24/7 team that fixes problems you didn’t even know you had.

    What makes them different from every other “managed WordPress” host?

    Most managed hosts compete on a feature checklist — sites, storage, CDN, staging, backups. BigScoots checks those boxes too, but the real differentiator is proactive support. They watch your site, push performance fixes you didn’t ask for, and respond to problems before you notice them.

    Real things they’ve done for us without being asked:

    • Pushed a server-side caching tweak that took a slow page from 1.6 s to 280 ms.
    • Migrated a site from another host overnight, end-to-end on their side, zero downtime.
    • Fixed a broken plugin update at 11 pm on a Sunday — within 12 minutes of the alert firing.

    Why we recommend it for newsletter operators

    If you’re sending a newsletter from WordPress, every minute the site is down is a minute your subscribers see a broken signup form, a dead referral link, or an empty archive. The cost of bad hosting isn’t the $10 you save — it’s lost trust with the audience you spent years building.

    BigScoots is more expensive than budget hosts. It’s worth it.

    Bottom line

    If you’re new to WordPress and wondering where to host your first newsletter site, BigScoots is the easy answer. If you’re tired of fighting with cheap hosting that breaks every other week, it’s the upgrade. One of those decisions you make once and never have to revisit.

    Heads up — some links in this article are affiliate links. If you sign up through them, we may earn a small commission at no extra cost to you. We only recommend tools we use ourselves.

  • When to add Beehiiv on top of your WordPress newsletter (and when not to)

    When to add Beehiiv on top of your WordPress newsletter (and when not to)

    If you already run a newsletter on WordPress, the most common question you’ll see in the operator forums isn’t “should I switch to Beehiiv — it’s “should I also be on Beehiiv?”. The framing matters, because Beehiiv stops looking like a competitor to a WordPress setup the moment you treat it as an acquisition channel rather than a publishing platform.

    We’ve been running both for the last several months. Here’s the honest decision framework we wish someone had handed us before we set the second one up.

    What Beehiiv actually adds (that WordPress can’t replicate)

    If you’re on WordPress, you already have the things that matter most — ownership of your subscriber list, deliverability control, your own domain, SEO that compounds on your archive, and pluggable customisation. None of those reasons go away when you add Beehiiv. So what does Beehiiv bring?

    The recommendations network. This is the single thing worth crossing the bridge for. Beehiiv’s discovery engine — both the in-post widget that suggests other newsletters to your readers, and the dedicated discovery network that surfaces your newsletter to people reading something adjacent — is the cheapest first-1,000-subscribers channel that currently exists. No WordPress plugin replicates it, including the cross-promotion plugins (we know — we’ve built one). The reason it works is network density, and you only get into that network by being on Beehiiv.

    Boosts. A pay-per-acquired-subscriber marketplace where you pay another newsletter operator to recommend you. The economics are deterministic in a way Meta and Google ads aren’t — you set a price per qualified sub, you only pay when one signs up. Boosts often outperform paid social on a CPA basis for newsletter-adjacent audiences.

    The ad network (optional revenue line). Beehiiv inserts sponsored ads into your posts and pays you a share. It’s not life-changing money at small list sizes, but it’s a real recurring revenue line with zero ongoing work — useful if you want monetisation without selling sponsorships yourself.

    That’s the value of adding Beehiiv. Now the cost.

    What it actually costs

    The plan tier you’ll end up on is somewhere in the Launch / Scale range — call it $0–$50/month depending on list size. That’s the obvious cost. The less obvious ones:

    • Time to keep two systems in sync. The bridge isn’t free. Every published issue needs to be cross-posted to Beehiiv if you want the web archive there to stay alive, and every signup on Beehiiv needs to find its way into your WordPress subscriber list (which is doable via their webhook system, but is one more thing to monitor).
    • Cognitive overhead. You’re now reading two analytics dashboards, debugging two send pipelines, and answering subscriber emails about which platform their account is on. For an individual operator this is real friction.
    • Audience confusion. If you mention your newsletter on social, which subscribe link do you give? If a reader asks “where can I read your archive?”, do you say the WordPress URL or the Beehiiv one? You’ll need a clear answer.
    • A small ongoing distraction. Beehiiv’s product is genuinely good, and once you’re inside it the upsell to use it as your primary platform (with their ad network, their paid tier infrastructure, their automation tools) is constant. Resist this if your WordPress side is working.

    When the addition is worth it

    The simple test: are you under 5,000 subscribers and actively trying to grow? Then yes, the recommendations network is probably the single highest-leverage thing you can add to your stack right now. The platform fee is negligible at that size, and the acquisition channel pays for itself within the first month if you’re publishing regularly.

    Two more specific cases where adding Beehiiv is a clear win:

    You publish about a topic that has natural cross-recommendation density on Beehiiv. Newsletter-about-newsletters, finance, sports, tech, lifestyle — these have hundreds of active publications on Beehiiv, which means the recommendations engine has something to work with. Hyper-niche B2B topics with three peer newsletters in the world won’t see much benefit.

    You want a passive revenue line that doesn’t require selling sponsorships. The Beehiiv ad network won’t replace your day job, but it’s real monthly money. For an operator who’d rather write than sell, it’s worth turning on.

    When the addition is wrong

    If your audience is past about 25,000 free subscribers or 2,500 paid, the platform fee starts to bite and the recommendations engine’s marginal value drops (your growth is mostly word-of-mouth and SEO at that scale anyway). Stick to your WordPress + Resend stack and put the saved fee toward content.

    If your newsletter is part of a larger product business — a course, an agency, an ebook funnel, a community — you don’t want subscriber records living in two places. The reconciliation overhead is more painful than the recommendations are valuable. Stay single-stack on WordPress.

    If you’ve been burnt by platform suspensions before, you have a real reason to be cautious. Beehiiv’s account-suspension issues are uncommon but documented — the difference vs WordPress is that on WordPress your worst case is a hosting bill, on Beehiiv it can be losing access to your audience without warning. The mitigation is to keep WordPress as the source of truth (which is what we do) so a Beehiiv suspension would cost you the discovery channel, not the list.

    How to set up the bridge cleanly

    If you decide to add Beehiiv, the configuration that gives you the most value with the least operational pain:

    1. Make WordPress the source of truth for subscribers. Every signup, wherever it lands, should end up in your WordPress subscriber table. Beehiiv’s API + webhooks let you wire this up — when someone signs up on Beehiiv, the webhook fires and creates the row on your side.
    2. Send the email from WordPress. You control deliverability, sender authentication, and per-issue customisation. Beehiiv’s send infrastructure is fine but you give up the levers.
    3. Use Beehiiv only as the acquisition layer and web archive. Recommendations engine on, Boosts marketplace on, ad network on if you want the revenue. But sending — the actual mail going out — runs through your WordPress stack.
    4. Cross-post each issue to Beehiiv as content. So the Beehiiv-side archive stays alive, the discovery network keeps surfacing your posts, and readers who arrive via Beehiiv have something to read. The Create Post API is on Beehiiv’s Enterprise tier today, so practically this means a copy-paste step into their editor or a manual import of the HTML.

    If you’re running One Two Three Send Pro on the WordPress side, the Beehiiv integration is built in — paste an API key and publication ID into Settings → Beehiiv, and the subscriber webhook + push side is wired up. The cross-post side is technically wired too, but it’ll only fire if you upgrade to Beehiiv Enterprise (their API restriction, not ours).

    The honest summary

    Adding Beehiiv to a WordPress newsletter is the right call for most operators between 0 and 5,000 subscribers who are actively trying to grow. It’s the wrong call once your acquisition is already working, or once your subscriber count is large enough that platform fees become meaningful.

    The pattern that works long-term is to treat the two platforms as different jobs — WordPress as your owned publishing layer, Beehiiv as a discovery channel that feeds it. That positioning protects you from the worst case on Beehiiv (account suspension, pricing changes) while still letting you use what’s genuinely best about it.

    If you’re starting from “I’m on WordPress, should I add Beehiiv too?” — the answer is probably yes, for now. Just be clear-eyed about which job each platform is doing for you, and don’t let the addition turn into a migration without you noticing.

    Some links in this post are affiliate links — we earn a small commission if you sign up through them, at no cost to you. We only recommend tools we actually use.

  • How to set up WordPress on DigitalOcean and install One Two Three Send

    How to set up WordPress on DigitalOcean and install One Two Three Send

    Most “host your own WordPress” guides assume you want to learn Linux. This one doesn’t. The goal here is a working newsletter site running on DigitalOcean, with One Two Three Send installed and ready to send your first email, in roughly 90 minutes. Cost: about $10/month all in. If you’ve never touched a server before, you can still follow this. Wherever a step needs more explanation than a sentence, we’ve put it inline. Wherever you can safely skip a sub-task, we’ve said so.

    Why DigitalOcean

    For a single newsletter site, you have three real options:
    • Managed WordPress hosts (Kinsta, WP Engine, SiteGround). $25–35/month minimum. Someone else handles the server. Worth it if your time is genuinely worth more than the cost.
    • Shared hosts (Bluehost, Hostinger). $3–5/month. Cheaper, but resource-constrained, oversold, and slow once your list grows past a few thousand.
    • Cloud VPS (DigitalOcean, Linode, Vultr, Hetzner). $6–12/month. You get a real Linux server. Slightly more setup, dramatically more control.
    DigitalOcean wins on simplicity for the cloud-VPS category. Their dashboard is the cleanest in the industry, their one-click WordPress image is genuinely good, and their pricing is predictable. Hetzner is cheaper if you’re in Europe; AWS Lightsail is comparable if you’re already on AWS for other reasons. For everyone else, DO is the default.

    Sizing the droplet correctly

    This is where most guides waste your money. The right droplet for a newsletter site depends almost entirely on subscriber count, not on traffic.
    Subscribers Droplet Monthly
    0–2,000 Basic 1GB / 1 vCPU $6
    2,000–15,000 Basic 2GB / 1 vCPU $12
    15,000–50,000 Basic 4GB / 2 vCPU $24
    50,000+ CPU-Optimized 8GB $84
    Start small. DigitalOcean lets you resize a droplet vertically (more RAM/CPU) with a five-minute reboot. There is zero benefit to over-provisioning. The $6 plan handles a couple of thousand subscribers comfortably.

    Step 1 — Create the DigitalOcean account

    Go to digitalocean.com and sign up. They’ll ask for a payment method. They give new accounts $200 in credit valid for 60 days, which is plenty to test multiple configurations before committing. Add a payment method even if you have credit — without one, your droplet gets destroyed when the credit expires.

    Step 2 — Spin up the WordPress droplet

    From the control panel: Create → Droplet.
    1. Region: pick the one closest to your subscribers. For a US/global audience, NYC3 or SFO3. For Europe, FRA1 or AMS3. For Asia/Pacific, SGP1 or SYD1. The droplet’s region determines the latency for your admin use; subscribers don’t see your droplet, they see the email’s sending IP (which is your email provider, not DO).
    2. Image: click the Marketplace tab and search “WordPress”. Pick “WordPress on Ubuntu 22.04”. This is the official DigitalOcean one-click image — it ships with WordPress, MySQL, nginx, PHP, and Certbot pre-installed. Saves you about three hours of setup.
    3. Plan: Basic → Regular. Pick the size from the table above.
    4. Authentication: SSH key if you know what one is, password if you don’t. (You can switch to SSH later.) Set a strong password and store it in a password manager.
    5. Hostname: something memorable like love-france-newsletter. Doesn’t affect anything outside the dashboard.
    6. Backups: tick the box. It’s 20% of the droplet cost ($1.20 on a $6 droplet) and it’s the cheapest insurance you’ll ever buy. Weekly snapshots, four-week retention, fully automated.
    Click Create Droplet. Wait 60 seconds.

    Step 3 — Finish the WordPress install

    Once the droplet’s ready, copy its IP address from the dashboard. SSH in:
    ssh root@YOUR_DROPLET_IP
    The first login runs the WordPress finalisation script automatically. It asks for:
    • Your domain name (or use the IP for now if you haven’t bought a domain yet)
    • An email address for Let’s Encrypt SSL certificate notifications
    • Whether to enable HTTPS (yes — it’s free and automatic)
    The script provisions an SSL certificate via Let’s Encrypt and configures nginx for HTTPS. This is the single best part of the DO marketplace image — getting SSL right manually is an hour’s work that you skip entirely. If you don’t have a domain yet, point your browser at the droplet’s IP and you’ll see the WordPress install wizard. Pick a strong admin password (NOT “admin” as the username — pick something obscure), set the site title, and finish.

    Step 4 — Point your domain at the droplet

    If you bought a domain (Namecheap, Cloudflare, or any other registrar), add two DNS records:
    • A record: @ → your droplet IP
    • A record: www → your droplet IP
    DNS propagation takes 5 minutes to an hour depending on the registrar. While you wait, log into WordPress at https://YOUR_DOMAIN/wp-admin. If SSL didn’t get set up during step 3 (because you didn’t have a domain yet), SSH back in and run:
    certbot --nginx -d YOUR_DOMAIN -d www.YOUR_DOMAIN
    Certbot handles the cert, the nginx config, and the auto-renewal cron job in one command.

    Step 5 — Set up backups (the second kind)

    You enabled DigitalOcean’s droplet backups in step 2 — those snapshot the entire server weekly. That’s good for “the droplet died” recovery. You also need WordPress-level backups for “I broke a plugin” recovery. The free UpdraftPlus plugin is the operator standard. Install it from Plugins → Add New, configure it to back up to Google Drive or Dropbox daily, and forget about it. Your insurance is now layered: UpdraftPlus restores the WP install in minutes, DO snapshots restore the entire server in an hour. Most operators never need either, but the one time you do, you’ll be glad you set both up.

    Step 6 — Install One Two Three Send

    From the WordPress admin: Plugins → Add New, search for “One Two Three Send”, click Install, then Activate. The plugin walks you through initial configuration:
    1. Claude API key. Get one from console.anthropic.com. Pasted into Newsletter → Settings → AI. Required only if you want AI generation; you can run the plugin without it and write everything by hand.
    2. Email provider. Pick one in Newsletter → Settings → Provider. For under 50,000 emails a month, Resend or Postmark are the easiest. Above that, switch to Amazon SES — we wrote a separate post on that.
    3. Signup form. The plugin creates a default form at Newsletter → Signup Forms. Copy its shortcode and paste it into a WordPress page (e.g. /subscribe) or a widget area.
    4. Welcome email. Newsletter → Settings → Welcome. New subscribers see this immediately on signup. The default is fine; customize the body to match your brand voice.
    That’s the minimum to start sending. Generate your first newsletter at Newsletter → New Newsletter.

    Step 7 — Optional: install One Two Three Send Pro

    If you want Stripe paywalls, custom newsletter templates, the public archive, the Newsletter Network cross-promotion widget, or the AI Agents blog generator, install the Pro companion plugin. Pro is distributed by email to subscribers of the One Two Three Send newsletter — sign up at onetwothreesend.com and the install link arrives within minutes. Once installed, Pro auto-updates from the manifest server; no manual updates needed.

    What you should NOT do on the droplet

    Some categories of work that look reasonable but will cause problems: Do not run your own SMTP server. Outbound port 25 on cloud providers is heavily blocked by inbox providers because so much spam comes from cloud IPs. Even if you got mail to leave the droplet, it would land in spam folders. Always use a dedicated email service (Resend, Postmark, SES) for sending. The droplet’s job is to host the WordPress admin and the public site, nothing more. Do not skip the firewall. Run ufw enable on first login and only open ports 22 (SSH), 80 (HTTP), and 443 (HTTPS). DO has a network-level firewall in the dashboard that’s even better — set it up to lock everything else down. Do not run as root forever. The marketplace image lets you log in as root by default. Within the first day, create a non-root user with sudo, copy your SSH key over, and disable root SSH login. There are guides for this; fifteen minutes of work that pays off the first time someone scrapes your IP looking for SSH brute-force opportunities. Do not install random WordPress plugins. Each plugin is server code running with database access. The plugin ecosystem is broad and most plugins are fine, but the bad ones are spectacularly bad. Stick to plugins with 100,000+ active installs, recent updates, and active support. UpdraftPlus, Yoast SEO, Wordfence, and One Two Three Send all qualify.
    A toolkit on a workbench
    Photo: Wikimedia Commons (CC)

    Long-term maintenance

    If you do nothing else, do these. Weekly: log in to WordPress and click “Update” on anything with an update available. WordPress core, plugins, themes. WordPress’s auto-update for minor versions is on by default; you’re checking that nothing got missed. Monthly: SSH in and run apt update && apt upgrade. Reboot if a kernel update comes through. This applies Ubuntu security patches. Quarterly: review installed plugins. Anything not actively used should be deactivated and deleted. Inactive plugins still receive updates and can introduce security issues. The one-click image ships with about a dozen utility plugins; remove any you’re not using. Annually: re-evaluate your droplet size. If your subscriber count has 5x’d, your $6 droplet is now under-provisioned. If your subscriber count hasn’t grown, your $24 droplet is overspending. DigitalOcean’s resize takes five minutes and a reboot.

    When DigitalOcean is the wrong choice

    If you genuinely don’t want to ever SSH into a server, pick managed WordPress hosting. Kinsta is the gold standard ($35/mo for a starter site); WP Engine is the enterprise default; SiteGround is the budget option. You pay 3–5x more, but you never have to think about Linux. If you’re running 100+ sites, DigitalOcean stops being optimal. AWS Lightsail with a Multi-AZ database, or a Kubernetes cluster on DO/Linode, becomes worth the additional setup. The break-even point is around 10–20 sites. If your audience is mostly in one specific region (say, Australia), pick a host with a data center in that region. DO’s SYD1 region is fine; alternatives like Vultr Sydney or AWS ap-southeast-2 are also options. For everyone else: DigitalOcean is the most boring infrastructure decision you can make for a newsletter site, and that’s the highest compliment infrastructure can earn.

    Heads up — some links in this article are affiliate links. If you sign up through them, we may earn a small commission at no extra cost to you. We only recommend tools we use ourselves.

  • WordPress hosting for newsletter operators — a thorough comparison

    WordPress hosting for newsletter operators — a thorough comparison

    Most “best WordPress host” articles are SEO-driven affiliate roundups that recommend whichever provider pays the highest commission that quarter. This isn’t one of them. We have run our newsletter on three of these hosts personally, and migrated between them more than once. What follows is what actually matters when you’re running a newsletter on WordPress — and which hosts handle it well.

    The criteria that matter for a newsletter site (and what doesn’t)

    Standard hosting reviews talk about page-load speed, uptime, and CDN coverage. For a newsletter site those are baseline — every host on this list passes them. The criteria that actually decide your experience, in order:

    1. Plugin upload freedom — you need to upload custom plugin zips. Some “managed WordPress” tiers explicitly disable this. Check before you sign up, not after.
    2. Outbound HTTPS & DNS reliability — your plugin will call Anthropic’s API, your email provider’s API, and possibly external image services. Some restrictive hosts allowlist only a handful of outbound destinations. This is the single most overlooked criterion and the one most likely to bite you.
    3. Reliable WP-Cron — newsletter sending is cron-driven. Hosts that disable internal cron and replace it with an external trigger usually do it well, but it’s worth verifying.
    4. SMTP / port 465 outbound — if you use SMTP rather than an HTTP-based email API like Resend, port 465 needs to be open. A few hosts block it by default.
    5. PHP 8.1+ available — required by One Two Three Send. Every modern host has this, but ancient shared-hosting boxes don’t.
    6. Real human support — when something breaks at send time you want a chat window with a human, not a 48-hour ticket queue.

    Speed and uptime are the easy parts. The list above is what separates a host that “works for newsletters” from one that fights you every step.

    The six hosts we actually have an opinion on

    BigScoots — top pick for managed WordPress

    What you’re paying for: a small team that genuinely knows WordPress, support that responds in minutes via chat, custom plugin uploads allowed without restriction, and a stack tuned for performance.

    • Pricing: Plans start ~$35/month, scaling to $150+ for high-traffic sites
    • Plugin uploads: Yes, no restrictions
    • WP-Cron: Reliable, runs as expected
    • Worth checking before committing: outbound network policy. We have seen one BigScoots-hosted site where outbound DNS resolution from PHP was failing — likely a per-account firewall configuration, but worth raising with their support before signup if your plugin needs to make external API calls (which One Two Three Send does, to Anthropic and to your email provider). Their support resolved similar issues quickly when reported.
    • Worth knowing: the entry tier is more expensive than budget hosts, but the support response time alone justifies the difference once you’ve had your first 11pm “why isn’t my newsletter sending” panic

    Best for: newsletter operators who want minimal fuss and have the budget. Avoid if: you’re under $50/month total tooling budget and willing to manage more yourself.

    SiteGround — the reliable mid-tier choice

    The host most “best WordPress hosting” lists put first because their support is genuinely good and their entry pricing is approachable. Plugin uploads work without restriction, outbound network is generally permissive, PHP 8+ available everywhere.

    • Pricing: ~$2.99/month introductory rate, ~$20/month renewal. The renewal price is what matters.
    • Plugin uploads: Yes, no restrictions
    • WP-Cron: Reliable on shared plans, with their own cron scheduler tooling
    • Watch for: the introductory pricing is an aggressive teaser. Renewal at year two is roughly 5× the first-year rate. Budget for the renewal price, not the sticker.
    • Worth knowing: their dashboard is genuinely well-designed — staging sites, WP installs, SSL, backups all in one panel

    Best for: first-time WordPress users who want sensible defaults at a moderate price. Avoid if: you’ll panic at the year-two renewal — set a calendar reminder to evaluate then.

    Cloudways — managed-cloud middle ground

    Cloudways isn’t a host in the traditional sense — it’s a management layer that runs your WordPress install on top of cloud providers (DigitalOcean, Vultr, Linode, AWS). You pay them for the management; the underlying server is whichever cloud you pick. This sounds complicated but the result is excellent: real cloud-grade performance with a familiar managed-WordPress dashboard.

    • Pricing: ~$11/month for a basic DigitalOcean droplet via Cloudways, scaling smoothly
    • Plugin uploads: Yes, no restrictions
    • WP-Cron: Disabled by default, replaced with their server-side cron — works reliably once configured
    • Watch for: the dashboard is power-user-friendly but has a bigger learning curve than SiteGround. You’ll see terms like “vertical scaling” and “Varnish” that wouldn’t appear on a typical managed-WP host’s UI.
    • Worth knowing: the same money buys you noticeably more raw server power than at SiteGround. Better fit for sites that grow and don’t want to migrate

    Best for: operators comfortable with a slightly more technical dashboard who want serious performance per dollar. Avoid if: you want a one-click setup and never to think about server config again.

    DreamHost — the genuine budget option

    DreamHost is the budget host that doesn’t feel cheap. Pricing is honest (the renewal rate is the same as the intro rate), plugin uploads work, support is responsive enough.

    • Pricing: ~$3–5/month for the basic shared plan, with no aggressive renewal markup
    • Plugin uploads: Yes
    • WP-Cron: Reliable
    • Watch for: shared hosting performance ceiling. Once you cross ~10,000 newsletter subscribers, send batches start to feel slow. You’ll outgrow this tier and want to upgrade.
    • Worth knowing: they’re employee-owned and have been around since 1996 — the unfashionable kind of stability

    Best for: launching on a tight budget when you’re not yet sure the newsletter will stick. Avoid if: you already have audience momentum and need performance headroom from day one.

    Kinsta — premium alternative to BigScoots

    Kinsta runs on Google Cloud Platform’s premium tier. Performance is excellent, the dashboard is the best in this category, support is good. The catch: pricing.

    • Pricing: Plans start ~$35/month for one site, scaling steeply for traffic
    • Plugin uploads: Yes, no restrictions
    • WP-Cron: Reliable, with their own scheduler
    • Watch for: visit-based pricing. Hit the visit cap of your plan and you’re forced to upgrade. For a newsletter site (low traffic, mostly subscribers reading email) this is rarely a problem, but for a content-heavy site it can be.
    • Worth knowing: their dashboard has APM (application performance monitoring) included — useful for diagnosing slow sites without third-party tools

    Best for: sites that prioritise dashboard polish and Google Cloud infrastructure. Avoid if: you don’t see specific value over BigScoots at the same price point.

    WP Engine — popular but ask the question

    WP Engine is one of the largest managed-WordPress hosts. The product is solid, the dashboard is good, the performance is competitive. But there’s a specific catch that matters for our use case: their lower-tier plans have historically restricted custom plugin uploads.

    • Pricing: Plans start ~$20–30/month
    • Plugin uploads: Verify per plan — entry tiers have restricted custom plugin uploads in the past. Their list of “disallowed plugins” has also been long enough to break some legitimate setups.
    • WP-Cron: Replaced with their own scheduler, generally reliable
    • Watch for: the disallowed-plugins list. Before signing up, send their pre-sales chat the question: “Can I upload a custom plugin zip on plan X?” Get the answer in writing.
    • Worth knowing: if you need a host purely for one of WP Engine’s specialty integrations (e.g. their Genesis themes), this might still be the right choice

    Best for: sites already in WP Engine’s ecosystem. Avoid if: you haven’t yet verified your plan tier permits custom plugin uploads — newsletter sending depends on it.

    Quick comparison

    HostEntry priceCustom plugin zipsBest fit
    BigScoots~$35/moYesPremium managed, top support
    SiteGround~$20/mo (renewal)YesFirst-time WP users, solid all-rounder
    Cloudways~$11/moYesPerformance per dollar, slightly technical
    DreamHost~$3–5/moYesGenuine budget, no renewal markup
    Kinsta~$35/moYesPremium, GCP-based, polished UI
    WP Engine~$20–30/moVerify per planExisting ecosystem users, after verifying plugin policy
    A road sign with multiple direction arrows
    Photo: Wikimedia Commons (CC)

    Honest recommendation by situation

    • Just launching, want zero fuss, $35+/month is fine: BigScoots
    • Just launching, $20/month budget, want a familiar managed dashboard: SiteGround
    • Slightly technical, want best performance per dollar: Cloudways
    • Tight budget, prepared to migrate later: DreamHost
    • Already inside the Google Cloud ecosystem or want premium dashboard polish: Kinsta
    • Already on WP Engine and happy: stay (after verifying plugin policy)

    Three things to ask any host’s pre-sales chat before paying for a year:

    1. “Can I upload custom plugin zip files on plan X?” — verify in writing
    2. “Are there any outbound network restrictions from PHP?” — specifically ask about API calls to api.anthropic.com and api.resend.com
    3. “Is internal WP-Cron enabled, or replaced with an external scheduler?” — either is fine; you just need to know which

    If their pre-sales team can’t or won’t answer those three questions clearly, that’s information too.

    What about WordPress.com Business and Hostinger?

    Two we deliberately excluded:

    • WordPress.com Business (Automattic-hosted) is technically WordPress but practically a different product. Plugin freedom is heavily restricted, the editor is overlaid with their own UX, and the pricing tier needed to upload custom plugins is steep. Skip unless you have a specific reason.
    • Hostinger at the entry tier is genuinely cheap (~$2/month) and the performance is acceptable, but support is automated-first and the renewal markup is steeper than DreamHost’s. If you need budget hosting and don’t mind chasing answers via tickets, it’s an option — but DreamHost gives you better support for similar money.

    Subscribe to the daily newsletter for more honest takes on the tools in your stack — and the pro plugin in your welcome email so you can ship your first issue this week.

    The newsletter for newsletter operators

    Daily field notes on deliverability, AI tools, hosting, and monetisation. No "top 10 plugins" filler — real tools, real numbers, real failures.

    Some links in this post are affiliate links — we earn a small commission if you sign up through them, at no cost to you. We only recommend tools we actually use.

  • How to write your first newsletter with One Two Three Send Pro

    How to write your first newsletter with One Two Three Send Pro

    You have a Claude API key, a Resend (or SMTP) provider, and the One Two Three Send plugin installed. From a fresh admin to a sent first issue takes about ten minutes. Here is the actual click-by-click flow.

    This guide assumes you have already done the platform setup — register a domain, install WordPress, install both the free and pro plugins. If not, start with our launch guide first.

    Step 1 — Configure the basics

    Newsletter → Settings. Three tabs need attention before you write anything:

    1. General — From name, From email (must be on a domain you have verified with your provider), Reply-to. Two minutes.
    2. AI — Paste your Claude API key. Get one free at console.anthropic.com. Pay-per-token, ~$0.05–$0.30 per generated newsletter.
    3. Email Provider — Pick Resend (recommended — generous free tier) or SMTP. Click Test connection. You should get a green tick.

    Optional but recommended: Subscriber tab. Paste the email you used to sign up for our daily newsletter and click Verify subscription. This unlocks auto-updates so future pro releases land via the standard WordPress yellow update banner instead of manual zip uploads.

    A hand drafting a letter on paper
    Photo: Wikimedia Commons (CC)

    Step 2 — Pick a template (optional)

    Newsletter → Templates. The pro plugin ships with the Newsroom template — dated masthead, italic sensory opener, a feature article, three to four eyebrow-and-CTA sub-sections, footer. It is the format big editorial newsletters use because it works.

    If you want something simpler — body text and one CTA — skip this step and the plugin will use your raw post content.

    Step 3 — Draft the newsletter

    Newsletter → All Newsletters → Add New. The standard WordPress block editor opens — write in Gutenberg the same way you would a blog post. Headings, paragraphs, lists, images, columns, embeds. Everything you can do in a normal post works in a newsletter.

    On the right sidebar you will see three pro meta boxes:

    • Newsletter — Subject line (this is what lands in the inbox), Tone (friendly / authoritative / casual / witty / formal / inspirational), Access (Free or Paid — Paid requires Stripe configured)
    • Pre-send audit — runs ten checks: subject length, link validity, spam triggers, placeholder leaks, readability, read time, more
    • Send — Send Now button

    Two ways to write the body:

    1. Write it yourself — type into the Gutenberg editor as normal. Use blocks for structure. Save draft.
    2. Let Claude draft it — Newsletter → New Newsletter (the legacy editor route). Pick tone and length, leave Topic blank to auto-pick from your most recent posts. Click Generate. The draft opens for editing.

    Whichever path you pick, the result is a normal WordPress post you can keep editing in Gutenberg.

    Step 4 — Run the audit

    In the right sidebar, click Run audit in the Pre-send audit box. The panel below the button fills with green PASS, yellow WARN, red FAIL rows. Each row tells you what to fix.

    Common warnings:

    • Subject length over 78 characters — Gmail truncates anything longer in the inbox preview
    • Spam-trigger words detected — “free”, “guarantee”, “act now”, “limited time” all hurt deliverability
    • Unsubscribe placeholder missing — pro auto-adds it at send time, but the audit confirms it is not literally typed in your body
    • Read time over 8 minutes — newsletters under that get higher click-through

    Fix anything red. Yellows are advisory — fix them if you can, ignore them if the warning does not apply to your specific issue.

    Step 5 — Send

    In the Send box, click Send Now. A confirmation dialog asks if you really want to send to all active subscribers. Click OK.

    Two seconds later the page refreshes with a green notice: “Sent to N subscribers.” Done.

    If your provider rejects any specific email (typo’d address, full inbox, etc.), the failure shows in your provider dashboard — Resend, MailerLite, Brevo all log per-recipient delivery. The plugin counts what was successfully accepted.

    Schedule instead of sending now

    If you want to write today and send tomorrow morning at 7:00, use Newsletter → Settings → Schedule. Pick a frequency (daily, weekly, monthly), day of the week, time, and check Auto-send. The pro scheduler then runs your draft through the editor pass + audit at send time, and only delivers if every check passes. Failures email you instead.

    After your first send

    Two things you only see post-send:

    • Open-rate reporting — Newsletter → Dashboard shows the percentage of subscribers who opened, with a 24-hour rolling chart. The pro plugin adds a 1×1 tracking pixel per recipient (de-duplicated, salted-hash storage, no per-subscriber data retained beyond the hash).
    • Public archive — if you turned on the archive in Settings, the issue is now live at /newsletters/[slug]/ for new visitors to read and discover.

    That is the full loop: configure once, draft, audit, send. By your fourth or fifth issue you will stop reaching for the AI tools and the audit will pass on the first run. The friction goes away fast.

    The newsletter for newsletter operators

    Daily field notes on deliverability, AI tools, hosting, and monetisation. No "top 10 plugins" filler — real tools, real numbers, real failures.

    Some links in this post are affiliate links — we earn a small commission if you sign up through them, at no cost to you. We only recommend tools we actually use.

  • How to launch a newsletter on your own domain — in three steps

    How to launch a newsletter on your own domain — in three steps

    Most newsletter advice starts with “sign up for one of the hosted platforms”. They work. They also take a percentage of your revenue, control your subscriber list, and lock your archive behind a domain you don’t own.

    If you would rather own the domain, the list, the archive, and the brand — and have the tooling be good enough that you stop noticing the platform underneath is yours — One Two Three Send is the alternative. Three steps from a blank browser tab to a sent first issue.

    Why a self-hosted newsletter

    Hosted newsletter platforms typically take a percentage of every paid subscription, charge per subscriber as your list grows, or curve their pricing up sharply once you cross five-figure contact lists. None of this is unfair — they are real businesses doing real work — but the maths only stays comfortable while your list is small.

    WordPress plus One Two Three Send pushes the cost structure the other way. You pay roughly $20 a month for the foundations regardless of list size, and your variable costs are the email provider you bring (Resend’s free tier covers the first 3,000 emails a month) and the Claude API by token (~$0.05–$0.30 per newsletter). The platform never takes a cut of paid subscriptions because there is no platform — there is just your site.

    You also get the things you cannot get on a hosted platform:

    • An archive on your own domain, indexed by Google, contributing to your SEO rather than someone else’s
    • A subscriber list inside your own database — exportable, transferable, never held hostage by a vendor
    • A site you can build any landing page you want on, with whatever theme you want, without fighting a platform’s rendering rules
    • Direct access to the underlying email logs when something gets stuck in spam

    What the plugin actually does

    The free plugin handles the awkward parts of running a newsletter inside WordPress: AI-assisted drafting through the Claude API, an editor sidebar with rewrite, shorten, expand, grammar, and subject-line tools, a 10-check pre-send audit (subject length, link validity, spam triggers, placeholder leaks, readability, more), scheduling, a subscriber database with token-based one-click unsubscribe, signup forms, welcome emails, and lead-magnet delivery.

    The pro plugin layers on Stripe paywalls for paid editions, Mailchimp / MailerLite / Brevo / Kit providers, popup and slide-in signup forms, a Claude-backed full audit, a public newsletter archive, open-rate reporting, the Newsroom template (the dated-masthead, sensory-opener, eyebrow-section format you may have seen in this newsletter), and a directive-driven Auto Content generator that writes blog posts on a schedule.

    Step 1 — Register a domain

    Pick a domain that is short, memorable, and ideally matches the noun your newsletter is about. Avoid hyphens. Avoid novelty TLDs (.tech, .news, .blog) unless your audience is specifically technical. A clean .com is still the cheapest signal of legitimacy you can buy.

    If you want a single provider for both domain and hosting, BigScoots also offers domain registration as part of their setup — convenient for keeping DNS, hosting, and renewals under one login. Otherwise, Cloudflare Registrar is what we use day-to-day: at-cost pricing (no markup over wholesale), no upsells, transparent renewal. Namecheap and Porkbun are both fine alternatives.

    Cost: roughly $10–15 per year for a .com.

    Step 2 — Get hosting for your WordPress site

    You want hosting that is:

    • Fast (at least 1 GB of RAM, preferably more)
    • Compatible with PHP 8.1 or higher and WordPress 6.0 or higher — both are now standard
    • Includes free SSL via Let’s Encrypt
    • Lets you upload custom plugins. Some “managed WordPress” hosts (WP Engine’s lower tiers, for example) restrict third-party plugin uploads — check before signing up

    Our top pick is BigScoots — they specialize in managed WordPress hosting, support is the kind that actually answers within minutes rather than days, and they let you upload custom plugins without restriction (which matters: you need to upload our pro plugin zip). Plans start around $35 per month.

    Solid budget alternatives: SiteGround (genuinely good support, easy install, ~$10–15 per month), DreamHost (cheap and reliable, ~$5 per month for the basic plan), Cloudways (more configurable but you manage some server bits, ~$11 per month for a basic DigitalOcean droplet).

    Once your hosting is provisioned, install WordPress through the hosting panel. Almost every modern host has a one-click WordPress installer that takes about three minutes.

    Cost: $5–35 per month depending on tier.

    Step 3 — Install One Two Three Send

    The plugin has two halves: a free version on wordpress.org, and a pro version delivered free by email when you subscribe to our daily newsletter.

    Install the free plugin

    1. WordPress admin → Plugins → Add New → search One Two Three Send
    2. Install → Activate. A new Newsletter menu appears in the admin sidebar.
    3. Newsletter → Settings → AI → paste a Claude API key. (Get one at console.anthropic.com — free to register, pay-per-token. A typical newsletter costs $0.05–$0.30 to generate.)
    4. Newsletter → Settings → Email Provider → connect Resend (recommended, generous free tier) or SMTP. Send a test email to confirm.
    5. Newsletter → Settings → General → set From name, From email (must be a verified domain in your provider), Reply-to.

    That alone gets you everything in the free feature set: AI-assisted drafting, the editor sidebar, the audit, scheduled sending, signup forms, welcome emails, and lead-magnet delivery. You can write and send your first newsletter from this state.

    Get the pro plugin

    Subscribe to the One Two Three Send daily newsletter — there is a signup form on our homepage. Your welcome email arrives within a minute carrying a download link to the pro zip. From there:

    1. Click the download link in the welcome email — saves the pro zip to your computer.
    2. WordPress admin → Plugins → Add New → Upload Plugin → pick the zip → Install Now → Activate.
    3. The Newsletter admin menu now has new entries: Templates, Auto Content. New tabs appear under Settings: Payments (for Stripe), Archive.

    Future updates land automatically — every new pro release shows up in your standard WordPress “Update available” notice within hours. One click, you are on the latest version. No emails, no manual zips after the first one.

    Cost summary

    • Domain: ~$12 per year
    • WordPress hosting: $5–35 per month (BigScoots managed at the top end, budget hosts at the bottom)
    • Claude API: ~$0.05–$0.30 per generated newsletter, no minimum
    • Resend: 3,000 emails per month free, then $20/month for 50,000
    • One Two Three Send (free + pro): $0

    Under $20 a month to launch on a budget host, under $50 a month on managed WordPress. Costs scale with usage rather than with subscriber count, which is the inverse of how every hosted platform prices itself.

    Send your first issue

    After step 3, you are ready to send.

    1. Newsletter → New Newsletter. Pick tone and length. Leave Topic blank to auto-pick from your most recent posts.
    2. Click Generate. The draft opens in the editor.
    3. Read it. Use Rewrite, Shorten, or Fix grammar in the AI sidebar to tighten anything that reads off.
    4. Click Run full audit. Fix any FAILs.
    5. Click Send Now. (Or schedule it.)

    The whole flow takes about ten minutes the first time. Most of that is reading what Claude wrote for you and deciding which sentences want a slight rewrite. By the third or fourth issue you stop reaching for the editor sidebar at all.

    If you have ever wondered whether the platform you write on actually deserves your subscribers, this is the alternative. Own the stack. Own the list. Write what you want.

    The newsletter for newsletter operators

    Daily field notes on deliverability, AI tools, hosting, and monetisation. No "top 10 plugins" filler — real tools, real numbers, real failures.

    Heads up — some links in this article are affiliate links. If you sign up through them, we may earn a small commission at no extra cost to you. We only recommend tools we use ourselves.

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