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May 30, 2026

Show me the money

👋 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...

May 23, 2026

Permission to speak freely to your email, sir?

👋 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...

May 16, 2026

Great artists steal...but how?

👋 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...

May 9, 2026

You're gonna need a bigger...discovery engine

👋 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...

May 2, 2026

Does your newsletter even MCP bro?

👋 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...

Apr 25, 2026

This revolution is <checks notes> being televised

👋 Hi Reader, I will be candid: I don’t watch a lot of TV. I haven’t watched much in the last 5 years if I remember correctly. So forgive me, if I am a bit late to the TV game. What I realized is Substack had already launched a TV app in Jan 2026 and it had extended a TikTok-like “For You” feed on their TV apps. SubStack's announcement in Jan 2026 The dissolution of intent As someone who consumes a lot of the written word, this strangely confuses me. If I subscribe to a newsletter creator, I...

Apr 18, 2026

’Tis the season to shop for owned audiences

👋 Hi Reader, ICYMI, OpenAI acquired TBPN earlier this month. If you haven’t heard about TBPN before, I feel sad for you. Jordi Hays and John Coogan run a show every weekday chronicling what’s happening in tech and business. What’s remarkable is they are getting acquired within 18 months of their existence. Is this the first instance of a tech company buying out a media brand? Hardly. HubSpot might be the one to get credit for starting the movement, buying out the Hustle, My First Million, and...

Apr 11, 2026

The obsession over lower CPAs

👋 Hi Reader, Manny Reyes spelled out what I was unable to articulate for the last month. I was at the New Media Summit at Austin in Feb, where Robin Re, VP of Marketing at Industry Dive, dropped a truth bomb. She mentioned that Industry Dive does not mind paying as much as $50 to acquire their subscribers. I was attending the same talk as Manny did, and I still remember gasping on hearing that number. When writing my NMS takeaway newsletter issue, I also made a note of following up to check,...

Apr 4, 2026

Starting and staying in the game long enough

👋 Hi Reader, This week, I have been spending quite a bit of time going through Dorie Clark’s work. I believe that the only skill that I arguably have is the will to be misunderstood in the short-term, as I try to build a long-lasting career in the long term. So when I heard that Dorie had actually written a book on this topic called ‘The Long Game’, I was intrigued. I am yet to read the book, but the fact someone as prolific as Dorie documenting their thesis on playing long-term games was...