📧 Paying for it to exist

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👋 Hey!

Kyle Lewis hadn't promised anyone anything when the first payments came in.

He was building OtterList, an ethical alternative to Amazon, and posting the whole process to TikTok and a free newsletter. Some readers started paying anyway. So Lewis gave them something to aim at: 500 Founding Supporter spots at $5 a month. The spots were gone within a few months, and he went full-time.

The newsletter is still free. The 600-plus paid supporters are just paying for OtterList to exist.

This week: Stratechery takes a sponsor after 12 years on subscriptions alone, beehiiv's editor finally fits on your phone, and Safari starts blocking the trackers hiding inside signup forms. Plus a Survivor podcast whose paid chat hit roughly 3,200 comments in an hour, and a test where cutting one click lifted signups 15.7%.

Let's dive in! 👇

Stratechery is now presented by Stripe, after 12 years on subscriptions alone. Founder Ben Thompson says paid subscribers see the ads too, he won't raise prices during the deal, and the money funds new products, starting with Sharp Tech on video.

beehiiv's editor finally works on your phone. The same release gives each newsletter its own sender name and reply-to, warns you about DMARC problems before you hit send, and saves poll answers to subscriber profiles.

Safari now blocks trackers that turn signup emails into tracking IDs. WebKit says identity resolution services quietly grab emails typed into newsletter signups and tie them to a permanent ID. If your signup page runs one, it goes quiet in Safari 27.

Podcast subscription platform Supercast now has a built-in newsletter. The newsletter tool comes with the base price of $0.59 per subscriber a month, and the dashboard shows which emails turn free readers into paid subscribers.

Buttondown makes the case for a National Newsletter Writing Month. Keep NaNoWriMo's 50,000 words in 30 days, but count an email course, a drip sequence or a bank of future issues. Sunday is November 1, if you need a start date.

Email Detective: Ever wondered how that newsletter was made?

Why You'll Love It: You know those emails that land in your inbox and make you think, “Okay… how did they do that?” With Email Detective, you can sneak a peek. The free Chrome extension shows you which email marketing platform sent an email, along with technical details like the HTML builder they used, as well as authentication details, right from Gmail or Outlook.

Best For: Anyone who's ever opened an email and wondered how it was made. So next time you come across an email you love, investigate it. You might pick up a few ideas of your own.

Turn your paid chat into a weekly watch party

How: Pick a moment your readers already show up for every week, like an episode airing, a match or an earnings call, and open a live chat thread for it. Drop Your Buffs, a podcast that watches Survivor alongside its listeners, does this every Wednesday night: one thread for the East Coast airing, one for the West Coast, both inside a Substack chat that only paid subscribers can enter. Co-host Sean Ross first left the chat open to everyone, found it a little Wild West, and moved it behind the paywall.

Why: Ross argues that social feeds stopped delivering real-time reactions once algorithms took over, so the live-tweet crowd lost its room. The chat gives that room back. The inside jokes, nicknames and memes are born there, which means anyone outside is, as he puts it, getting half the story. That's what the $5 a month buys: a seat where the show's lore gets made.

Expected Result: Their biggest watch party drew roughly 3,200 comments in an hour, by a listener's count. When the long-promised live show in New York finally happened, it sold out quickly and fans who'd bought single tickets used the chat to find each other and meet up before the show. There are no conversion numbers here, so treat this as a retention play. Start with one recurring thread, then split topics into Substack's new Chat Channels (up to 16 subscriber chats) once it gets crowded. Any platform with a members-only chat or community can run the same play.

Read the full interview.

Spotlight: OtterList Insider by Kyle Lewis

What works:

Creator quote: "You don't necessarily need a huge audience to build meaningful recurring revenue." Kyle Lewis, founder, OtterList

Your takeaway: If readers keep asking how they can help, give them a number to chase. Cap a founding tier, report progress toward it in your issues, and close it with a real deadline. Keeping the newsletter free keeps new readers coming in while supporters pay for the build. It works best when readers can watch the thing they're funding take shape, so if there's nothing to show yet, show the work.

Read the full interview.

Test: Franciscan University runs Faith and Reason, a content site where visitors can sign up for free courses. To subscribe, visitors had to click a button, which then opened the signup form. From May 9 to 20, 2025, in a test documented by fundraising research firm NextAfter, the homepage either kept that button or showed the signup form embedded right on the page.

Result: The embedded form had a 22.8% sign-up rate, against 19.7% for the button. That's a 15.7% relative lift at 95.5% confidence. The test needed 1,341 visitors to be valid and got 2,811.

Takeaway: Every extra click between a reader and the email field is a chance to wander off. If your homepage or post footer says "Subscribe" and then opens a pop-up or a separate page, test putting the field itself in plain sight. Keep the caveats in mind: one site, a short window, and free courses as the offer, which is a stronger hook than most newsletters have. NextAfter itself suggests repeating the test before treating the lift as settled.

See the full experiment.

Thanks for reading,

Eren & Cagri