👋 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...
13 days ago • 3 min read
👋 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...
19 days ago • 3 min read
👋 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...
27 days ago • 3 min read
👋 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...
about 1 month ago • 2 min read
👋 Hi Reader, There is one question I keep hearing from new newsletter operators I talk to, across the globe. When do I start monetizing? And I never had a crisper answer, than what Tom Alder put in his post on LinkedIn recently. Tom's post on LinkedIn this week I admire Tom’s consistency in building Strategy Breakdowns and I follow his journey closely. I also devoured the entire onboarding breakdown about Strategy Breakdowns (I know, very meta) that Chenell Basilio from Growth In Reverse had...
about 1 month ago • 2 min read
👋 Hi Reader, In my two decades in tech, I have been called many things. Dramatic was not one of them. Until Feb 2026. I wrote about Gemini taking over your email in LetterStack's Feb issue. The overall response I got was: I was being way too dramatic about losing open rates wholesale. LetterStack's issue in Feb about Gemini in Gmail Fast-forward to May 2026. and Google IO’s announcements made me realize one thing: I wasn’t being dramatic enough. What Google IO’s announcement means for...
about 2 months ago • 3 min read
👋 Hi Reader, As you may be well aware with the movie references here, I am a movie nut first, and a newsletter person second. I just stumbled into the world of newsletters a few years ago. But as a marketer, I have always been amused when people get antsy when they see someone else's content copied. To me, the AI-generated content theft debate is a movie I have seen before. Several times. But before we get there, let me take you back to the quote you see in the subject line: Good artists...
about 2 months ago • 3 min read
👋 Hi Reader, This thought has been living in my mind rent-free for a while now. Every time I talk to a newsletter creator who is doing genuinely good work, I ask them the same question. How are people finding you? The answer, almost every single time, is: social content, and whenever the newsletter platform decides to show people organically. And that second part is the problem. These Walled Gardens If you have built your product for distribution before, chances are you have run into walled...
2 months ago • 3 min read
👋 Hi Reader, I am a big fan of builders, who can ship product fast. I have been working in product for 2 decades now, and I sincerely believe CEOs who can ship fast, do well and last longer in business. Period. So when I see Tyler Denk and his team of builders at beehiiv ship, my eyes water. I have not seen an org ship this fast and at scale, the sole exception being Anthropic with Claude. Take for instance, all the features beehiiv has shipped just in the past 8 weeks. I had covered their...
2 months ago • 3 min read