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| Date | Title | Standfirst | Author | Words | Opening line | Link |
|---|---|---|---|---|---|---|
| Nov 3 | Lenny’s Newsletter holiday gift guide 2026 | 100+ gift ideas—all things I actually use, love, and recommend | Lenny Rachitsky and Michelle Rial | 2158 | The holidays are fast approaching, so I’m back with my sixth (!!) annual gift guide. | https://www.lennysnewsletter.com/p/lennys-newsletter-holiday-gift-guide-057 |
| Oct 13 | How to tell if a startup has a moat | A framework for assessing whether the company you’re considering joining is built to last | Dan Hockenmaier | 2191 | Moats! | https://www.lennysnewsletter.com/p/how-to-tell-if-a-startup-has-a-moat |
| Sep 29 | All of the Lenny & Friends Summit talks are now online! | Plus, some reflections and takeaways from the day | Lenny Rachitsky | 1226 | I’m excited to share that every main-stage talk from the recent Lenny & Friends Summit is now online. | https://www.lennysnewsletter.com/p/all-of-the-lenny-and-friends-summit |
| Sep 22 | Advanced evals: How to find (and fix) hidden AI failures in your product | Why you should never skip error discovery | Hamel Husain and Shreya Shankar | 3088 | Evals have been coming up more and more in my conversations with podcast guests and PMs. | https://www.lennysnewsletter.com/p/advanced-evals-how-to-find-and-fix |
| Sep 15 | 60+ new creative growth ideas | How to stand out when everyone is running the same playbook | Tom Orbach | 3933 | Tom Orbach writes the most delightful and actionable newsletter for anyone looking to grow their product. | https://www.lennysnewsletter.com/p/60-creative-growth-ideas |
| Sep 1 | How to turn your AI into a world-class designer | An end-to-end process for tapping into AI’s hidden creativity | Anshu Chimala | 3853 | I’d always thought AI was bad at design. | https://www.lennysnewsletter.com/p/how-to-turn-your-ai-into-a-world |
| Aug 25 | How to figure out your next career move | Six essential questions to help you navigate change | Cliff Maxwell | 2862 | Building on last week’s very exciting launch of Lenny’s Jobs (that’s a lot of likes!), I’m thrilled to bring you a companion post that will help you clarify what job to look for in the first place. | https://www.lennysnewsletter.com/p/how-to-figure-out-your-next-career |
| Aug 18 | Announcing Lenny’s Jobs: The best place in the world to find, vet, and land your dream job | Where product managers, engineers, designers, and growth/marketing professionals discover high-quality open roles at tech companies | Lenny Rachitsky | 886 | My goal is to help you succeed in your career. | https://www.lennysnewsletter.com/p/announcing-lennys-jobs-the-best-place |
| Aug 11 | How to make people care about your startup | Three founder archetypes—and how to turn your origin story into a communications strategy | Kristen Lowe | 4196 | Kristen does such an incredible job of introducing this piece that I’ll just skip my regular intro and jump right into it. | https://www.lennysnewsletter.com/p/how-to-make-people-care-about-your |
| Aug 4 | What if you’re not supposed to have a long-term plan? | The case for career emergence | Molly Graham | 3126 | Molly Graham’s first guest post, The Waterline Model, quickly rose to be my 7th most popular post of all time—extra impressive for not being about AI. | https://www.lennysnewsletter.com/p/what-if-youre-not-supposed-to-have |
| Jul 28 | 11 products I love, free for a year—the biggest Product Pass expansion in 2 years | Runway, Higgsfield, Waking Up, Brain.fm, Customer.io, Resend, Pangram, Mercury Personal, Supercut, Readwise, and Jam are joining Product Pass today, all… | Lenny Rachitsky | 2024 | If you thought this subscription couldn’t possibly get any better, you ain’t seen nothing yet. | https://www.lennysnewsletter.com/p/productpass-summer2026launch |
| Jul 21 | Why a sabbatical can change everything | How to take Big Time Off | Lenny Rachitsky | 3678 | This newsletter wouldn’t exist if I hadn’t taken a sabbatical. | https://www.lennysnewsletter.com/p/how-to-take-a-sabbatical |
| Jul 7 | How tech workers are feeling in 2026: a workforce splitting in two | Results from our second annual tech worker sentiment survey | Noam Segal and Lenny Rachitsky | 4408 | A year ago, we ran our first large-scale survey of how tech workers feel about their jobs and careers. | https://www.lennysnewsletter.com/p/how-tech-workers-are-feeling-in-2026 |
| Jun 30 | How top PMs increase their leverage with AI | A framework for getting the most out of AI in your day-to-day-work | Colin Matthews | 2382 | For years, the PM job drifted toward coordinating and aligning people. | https://www.lennysnewsletter.com/p/how-top-pms-increase-their-leverage |
| Jun 23 | The new inner game: Your unfair advantage in the age of AI | A playbook for the biggest upheaval of work we’ll see in our lifetime | Joe Hudson | 3363 | Joe Hudson is one of the most sought-after executive coaches in Silicon Valley, working with influential leaders like Sam Altman (OpenAI CEO) and founders and execs across Apple, Google, X, and more. | https://www.lennysnewsletter.com/p/the-new-inner-game-your-unfair-advantage |
| Jun 9 | Essential books for product builders—part 2 | 24 more timeless books that’ll make you a better builder, leader, and person | Lenny Rachitsky | 1021 | On the heels of part 1 of my essential books for product builders series, I’m excited to share part 2. | https://www.lennysnewsletter.com/p/essential-books-for-product-builderspart-611 |
| May 26 | Essential books for product builders—part 1 | 36 timeless books that’ll make you a better builder, leader, and person | Lenny Rachitsky | 1064 | I was a shy kid growing up, so I spent a lot of time reading books. | https://www.lennysnewsletter.com/p/essential-books-for-product-builderspart |
| May 19 | The Lenny and Friends Summit is back! | September 10th in San Francisco. Applications are now open. | Lenny Rachitsky | 517 | Two years ago, we held the first-ever Lenny and Friends Summit. | https://www.lennysnewsletter.com/p/the-lenny-and-friends-summit-is-back |
| May 5 | Why SaaS freemium playbooks don’t work in AI, and what to do instead | How to build an AI monetization strategy that actually works | Vikas Kansal | 1663 | Today’s guest author, Vikas Kansal, leads product for Google AI, arguably the most successful consumer subscription bundle in history, with Gemini 3.1, Nano Banana, NotebookLM, Veo3, and terabytes (!) of cloud storage. | https://www.lennysnewsletter.com/p/why-saas-freemium-playbooks-dont |
| Apr 28 | Your Couch-to-5K for AI | A step-by-step guide to building an AI habit that sticks | Hilary Gridley | 937 | I’m teaming up with AI native and my many-time collaborator Hilary Gridley on a project that will accelerate your AI learning more than anything you’ve tried. | https://www.lennysnewsletter.com/p/your-couch-to-5k-for-ai |
| Apr 21 | New: A free year of Cursor, Google AI Pro, Notion, Supabase, Gumloop, and Fin for subscribers | Now 25 incredible products totaling over $30,000 in value—free with your Lenny’s Newsletter subscription | Lenny Rachitsky | 1542 | Update: The Product Pass has been updated since this post was published. | https://www.lennysnewsletter.com/p/new-a-free-year-of-cursor-google |
| Apr 14 | Not all AI agents are created equal | A framework for categorizing and prioritizing your agent initiatives | Hamza Farooq and Jaya Rajwani | 2901 | Agents are so hot right now. | https://www.lennysnewsletter.com/p/not-all-ai-agents-are-created-equal |
| Apr 7 | A visual guide to getting out of a creative slump | On creating work like a human (and all the feelings that come with it) | Michelle Rial | 1329 | I’m so, so excited to share a guest post by Michelle Rial, my wife! | https://www.lennysnewsletter.com/p/a-visual-guide-to-getting-out-of |
| Mar 31 | OpenClaw: The complete guide to building, training, and living with your personal AI agent | I built a team of 9 AI agents that run my work and life. Here's how you can too. | Claire Vo | 2271 | Claire Vo has put together the definitive step-by-step guide to getting started with and mastering OpenClaw. | https://www.lennysnewsletter.com/p/openclaw-the-complete-guide-to-building |
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