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Follow the money

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Aug 1, 2026

Follow the money

👋 Hi Reader, The irony is not lost on me. I am covering a newsletter platform exodus today, as I am deliberating switching to a different newsletter platform. But more on that in next week’s issue. I spent time this week going into all the angles on the Emma Roth Substack story from The Verge. In her words, writers are fleeing Substack, because of a pricing model that puts a choke hold on their subscriber business. I think she's right on the money. Emma Roth's Substack story on The Verge We...

You can't handle the truth (about your other reader)

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Jul 25, 2026

You can't handle the truth (about your other reader)

👋 Hi Reader, When I started writing for LetterStack, I always used to think about what my subscriber of one looks like. I used to worry about what would make them hit reply, instead of unsubscribe. But I never once thought about the other reader, the one that gets to my content, before my subscriber does. Let me explain. Jonathan Coleman, who's a content design leader at HubSpot and a friend, posted about a Netflix job listing this week. The job listing has been burning up LinkedIn, with...

You are gonna need a bigger...level of content strategy

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Jul 18, 2026

You are gonna need a bigger...level of content strategy

👋 Hi Reader, Each week, my guilty pleasure is spending a lot of time just taking notes from top-tier creators. Do these notes translate well to applying it on my own content? I will let you speak for that. But I digress. Back to taking notes. This week I have been spending a lot of time bingeing on Kane Kallaway’s Youtube channel. I believe few people articulate how to break down great content strategy, like Kallaway does. Here’s his channel, if you are so inclined. Why am I bingeing on this...

Is there more to life than being really, really, ridiculously good looking?

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Jul 11, 2026

Is there more to life than being really, really, ridiculously good looking?

👋 Hi Reader, You may not know this, but my wife and I ran a fashion startup (virtual try-ons) for a year. In 2020. In the heat of COVID. Naturally that did not work out: people were happy to continue in their pajamas. But the tenacity with which we kept tabs on the fashion niche like a hawk never let go. The Business of Fashion subscription might have helped too :) So when Plum Sykes published 'The Fashion-Trust Metric' Substack issue from the Cannes Lions Festival of Creativity, naturally I...

You can't touch this (your audience)

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Jul 4, 2026

You can't touch this (your audience)

👋 Hi Reader, History may or may not repeat itself, but it most definitely rhymes. This time, the rhyme is on crypto creators on Instagram. On Friday, I woke up (don't judge me by my morning routine, I am not a biohacker bro) to multiple Instagram crypto community creators losing their audience overnight: Sujal Jethwani @SujalJethwani I just lost 234K people Instagram SUSPENDED my account today And this isn't new. Our previous account, Viral Theories (1M+ followers), was suspended too. - 5...

You had the baby, you raise the baby

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Jun 27, 2026

You had the baby, you raise the baby

👋 Hi Reader, An incredible number of new newsletter operators that I speak to follow this pattern: They launch their newsletter with gusto and enthusiasm. They write it for a few weeks without dropping a beat. And then, in a few months, they see other newsletters copy their ideas, format, even the color palette. They find that copycat versions make more noise, especially online, racking up subscribers. And their confidence deflates quickly. My response to them: If you are getting good at what...

You can’t sit with us

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Jun 20, 2026

You can’t sit with us

👋 Hi Reader, I have had the opportunity to see Erik Torenberg up close, albeit virtually. I was one of the instructors at OnDeck's product fellowship (or ODF as its called), which is the accelerator Erik and Julian Weisser ran in 2023. I have since followed his work closely at Turpentine and a16z (I also applied for the New Media fellowship and got rejected - boohoo). So when Erik wrote an essay about the first year at New Media at a16z, I naturally spent an inordinate amount of time reading...

Substack going the LinkedIn route?

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Jun 13, 2026

Substack going the LinkedIn route?

👋 Hi Reader, You know me. I keep my eyes peeled on anything happening on Substack. Be it the recent revelation for Substack sponsored ads (h/t to Tyler Morin and Louis Nichols from the LetterLand Live Show) or the recent ModernRetail article about brands taking Substack seriously below. ModernRetail's article on Brand Substacks And I have a nagging feeling about this phenomenon. As if I have seen this playbook before. A deja vu which kept gnawing on my brain since the time I read this...

What's in the box?

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Jun 6, 2026

What's in the box?

👋 Hi Reader, Choosing an ESP platform for the first time is so unnerving. Most ESPs offer similar features like building newsletter with drag-and-drop features, email capture UI options, the works. I hear this question across newsletter operators who are starting out on this journey. LetterStack doesn’t have a huge audience (yet), so I might be the right conduit to their concerns on ESP selection too. One factor I wish more people paid attention to is: how responsive is the ESP team? To the...

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