Lenny RachitskyModify

2026-05-26 23:25:52

👋 Hey there, I’m Lenny. Each week, I write about building product, driving growth, and accelerating your career. For more: Lenny’s Podcast | Lennybot | How I AI | My favorite AI/PM courses, public speaking course, and interview prep copilot

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I was a shy kid growing up, so I spent a lot of time reading books. I devoured sci-fi, nonfiction, and every programming book I could find. When the library didn’t have the C++ book I wanted, I taught myself to code by buying book after book from our local Borders (RIP). I was tearing through so many coding books that my dad started returning the ones I’d finished to the bookstore so we could afford to buy more.

I’ve always thought it was so cool that the smartest person in the world on a topic I care about spent years of their life distilling their best ideas into an enjoyable read, and I can get this for just $20. Amazing.

There’s endless free content flying at us now—newsletters, podcasts, tweets, oh my—but how many blog posts or tweets have had anywhere near the lasting impact on your life as a great book?

To continue my essential-reads series (don’t miss part 1 and part 2 of my favorite online essays), I’ve put together a collection of my all-time favorite books, organized by their jobs-to-be-done. When your manager tells you to work on a particular skill—or if you’re just feeling the itch for self-improvement—these are the books I recommend.

To keep this list extremely high signal-to-noise, I forced myself to pick only three books per category (so hard!), and only books I’ve completed. I included both classics and under-the-radar gems. I also agree with Marc Andreessen’s take that you should mostly read books that are over 10 years old (because those are the ones that have stood the test of time), so you’ll notice very few newer books.

There are so many great books that I didn’t include, either because I haven’t had a chance to read them or they just missed the cut. I probably forgot some important titles, too. That’s why there’ll be a part 2!

P.S. If you feel like you have no time to read, I was in the same boat. Bryan Johnson’s suggestion to read a book for 10 minutes before bed changed my life. I started reading more books, and I got better sleep! Try it out.

I want to improve my communication skills

I had never written anything online before starting this newsletter, so once I realized this was going to be a thing, I decided I needed to learn something about writing. Friends recommended many different books, and I read them all. But these three had the most practical, impactful, and lasting advice, which is still lodged in my head even now.

1. Nobody Wants to Read Your Sh*t by Steven Pressfield

2. On Writing Well by William Zinsser

3. Storyworthy by Matthew Dicks

Check out my conversation with Matthew Dicks.

I want to get better at executing

If you love this newsletter, you crave actionable, tactical advice and frameworks that you can put into practice immediately. The first two books will give you exactly that, and the third will give you a meta-framework that’ll level up how you approach everything at work.

1. The Great CEO Within by Matt Mochary

2. Scaling People by Claire Hughes Johnson

3. The Goal by Eliyahu Goldratt

Check out my conversations with Matt Mochary and Claire Hughes Johnson.

I want to get better at strategy

I remember reading these books and feeling like, okay, I finally understand what “strategy” is.

1. Good Strategy/Bad Strategy by Richard Rumelt

2. Playing to Win by Roger L. Martin

3. Working Backwards by Colin Bryar and Bill Carr

Check out my conversations with Richard Rumelt, Roger Martin, and Bill Carr.

I want to be inspired to build something great

This bucket of books might be my favorite of the bunch. They showed me how much a singular (relentless) mind can accomplish. Read them, and you’ll be ready to run through walls.

1. The Making of Prince of Persia by Jordan Mechner

2. Build by Tony Fadell

3. Shoe Dog by Phil Knight

I want to become a better manager

These books are among the most mentioned on my podcast. I remember reading High Output Management when I was a baby manager, and it finally taught me what my job actually was. The Making of a Manager is the modern version of that book. And Radical Candor forever shifted how I think about hard feedback.

1. High Output Management by Andy Grove

2. The Making of a Manager by Julie Zhuo

3. Radical Candor by Kim Scott

Check out my conversations with Kim Scott and Julie Zhuo.

I want to become a better leader

I love how the combination of these three books sums up great leadership: push people to do the best work of their lives, but be human about it, and, in the end, the score will take care of itself.

1. Amp It Up by Frank Slootman

2. The 15 Commitments of Conscious Leadership by Jim Dethmer, Diana Chapman, and Kaley Klemp

3. The Score Takes Care of Itself by Bill Walsh

I want to increase my product success rate

These classics taught me the fundamentals of product management: talking to customers, prioritizing roadmaps, and what it takes to build something valuable and impactful.

1. The Mom Test by Rob Fitzpatrick

2. Escaping the Build Trap by Melissa Perri

3. Continuous Discovery Habits by Teresa Torres

Check out my conversations with Melissa Perri and Teresa Torres.

I want to level up my product org

These books are also some of the most mentioned on my podcast, because they’ll shift how you think about the role of product within your organization, and how to make decisions in uncertain environments.

1. Empowered by Marty Cagan

2. Inspired by Marty Cagan

3. Thinking in Bets by Annie Duke

Check out my conversations with Marty Cagan (and, again, Marty Cagan) and Annie Duke.

I want to get better at sales and marketing

With AI making it easier to build, distribution is becoming the bigger bottleneck. This is not a natural strength for most builders, which is why you need to develop your marketing and sales muscle. I learned more about marketing and sales from these three books than from anywhere else.

1. Purple Cow by Seth Godin

2. Obviously Awesome by April Dunford

3. Founding Sales by Peter Kazanjy

Check out my conversations with Seth Godin, April Dunford, and Peter Kazanjy.

I want to be more productive

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2026-05-25 23:02:59

How the engineer behind Claude Cowork actually uses Claude | Felix Rieseberg (Anthropic)

Brought to you by:

• Magic Patterns—Prototypes that look like your product

• Guru—The AI layer of truth

Felix Rieseberg, the engineering lead for Claude Cowork and Claude Code Desktop at Anthropic, joins Claire to show how he actually uses Claude in his own life and work. In this episode, Felix walks through building a 3D floor planner from a 2D house plan, using email as a personal inventory database, creating live dashboards from connected apps, and hacking together a $20 hardware “Claude buddy.” He also shares his philosophy for getting more out of AI: go one abstraction layer up, let Claude work in the background, and stop assuming computers can’t solve some of the annoying little problems in your life.

Biggest takeaways:

1. The biggest barrier to AI adoption is people not realizing they can ask AI to solve almost any problem. Felix sees this constantly—the tools are incredibly powerful, but users haven’t built the muscle memory to reach for them. His advice: whenever you’re doing something annoying that doesn’t feel creative, pause and ask yourself if Claude could do it instead. The gap isn’t technical; it’s psychological.

2. Your email is an untapped gold mine of personal data. Felix used his email to inventory all his furniture when moving houses: every purchase receipt, every confirmation, every dimension. Claude parsed it all and built him a 3D floor planner with his actual furniture. This same principle applies to clothing, medical records, travel history, or any domain where you’ve been emailing receipts and confirmations for years. You already have a structured database—you just need to point Claude at it.

3. Go one abstraction layer up, then do it again. Felix started manually entering furniture dimensions into his floor planner, then stopped and asked Claude to figure out what furniture he had. Then he went another layer up and told Claude to find the furniture in his emails. This is the key pattern: every time you catch yourself doing tedious work, ask how Claude could do it instead. Then ask how Claude could figure out what to do without your telling it.

4. Live artifacts are Claude’s answer to keeping your personal dashboards always up-to-date. Unlike static artifacts, live artifacts refresh with real-time data from your connected services—Spotify, Gmail, Calendar, Notion, whatever you’ve authorized. Felix built a personal dashboard that looks like early-2000s software that updates throughout the day. The killer feature: you never have to manually update your pitch deck, your daily briefing, or your personal reports again.

5. Choose Opus when you don’t know what you’re really asking for. Felix’s heuristic for model selection: use Sonnet when the problem is well-scoped and specific. Reach for Opus when you need Claude to interpret what you actually want, not just what you said. It’s the difference between “make me a floor plan with units” (Sonnet territory) and “help me figure out how to organize my life” (Opus territory). For most tasks, Sonnet is perfectly capable, but when you need that extra layer of problem decomposition, Opus is worth it.

6. Kids are the best AI users because they aren’t afraid to ask for things. Felix gets videos from parents showing what their kids build with Claude—custom video games with hand-drawn characters, interactive stories, tools that would have required a software engineer just a few years ago. Adults have spent 20 years in a “mind prison” learning what computers can’t do. Unlearning that is the unlock.

7. When Claude makes mistakes, debug your workflow, not the model. Felix doesn’t curse at Claude (though he notes it’s useful for the team to know when people do). Instead, he asks it: “Here’s what I expected. Can you walk me through where things went differently? How can we prevent this in the future?” Usually the fix isn’t “Claude can’t do this”; it’s “I need to change the prompt, clean up the data source, or set up a dry run.” Treat Claude like a collaborator who needs better instructions, not a tool that’s broken.

What launched at Google I/O 2026 (30-minute day 1 recap)

Brought to you by:

• Magic Patterns—Prototypes that look like your product

• ThoughtSpot—Build AI-powered analytics into your product

Claire breaks down the biggest launches from Google I/O 2026—from Gemini 3.5 Flash and Antigravity 2.0 to Google AI Studio, Omni, Flow, Stitch, and Pomelli. In this episode, she tests the tools live, shares what actually works, and explains where Google is catching up, where it may be pulling ahead, and why its launch-to-availability gap is still such a problem for builders.

Biggest takeaways:

1. Gemini 3.5 Flash rivals leading frontier coding models in Google’s benchmarks while running four times faster. Google positions this as their agentic coding model, optimized for tasks requiring both high reasoning and rapid execution. If the benchmarks hold in practice, this speed advantage could shift the coding agent landscape toward Google’s tools.

2. Antigravity 2.0 brings Google’s IDE to feature parity with Claude Code and Codex—but it’s playing catch-up. The update includes projects (folder-constrained workspaces), scheduled tasks on Cron, and subagents for specific tasks. The UI looks nearly identical to Codex, and the features match what Anthropic and OpenAI shipped months ago. The advantage is speed: if Gemini 3.5 Flash delivers, developers might choose Antigravity for well-scoped tasks that need to ship fast.

3. The /grill-me slash command is Antigravity’s aggressive take on Claude Code’s polite clarification tool. Instead of gently asking questions, /grill-me promises to interrogate your requirements and get to the heart of what you’re building. Whether this is actually more hardcore or just clever branding remains to be seen, but it signals Google’s attempt to differentiate on personality.

4. Google AI Studio now integrates directly with Workspace apps—or it’s supposed to. The promise: build no-code apps that read Sheets, draft Gmails, organize Drive, and see Calendar without setup. Claire couldn’t get it to work during testing. If it delivers, it would capture internal enterprise productivity use cases and personal assistant workflows where Google already owns the data layer.

5. Omni is Google’s answer to Sora, focused on longer, production-quality video. The model creates 10-second videos (versus Sora’s 6 or 7 seconds), maintains character consistency across edits, and allows conversational editing. Claire tested it by animating her kid’s drawing, and the output was impressive. The real power will be in production workflows where you iterate on the same characters and scenes multiple times.

6. Flow is Google’s production-grade video editor built on Omni. It lets you define characters, create avatars, and edit videos conversationally while maintaining cinematic quality. The tool targets creators and marketers who need consistent, high-quality video at scale. Claire tried creating an avatar of herself, but the feature failed—a recurring theme throughout I/O announcements.

7. Stitch and Pomelli are Google’s design and marketing tools. Stitch is like in-browser Figma with streaming design generation, inline AI edits, and code sync. Pomelli creates brand books, campaign assets, and websites from a URL. Both show promise but suffer from “Google slop,” the generic aesthetic of AI-generated design.

8. Gemini’s multimodal capabilities remain its strongest differentiator. For work involving files, videos, or transformative work across modalities (document to video, image to text), Gemini models excel. Claire uses them for generating blog posts from podcast videos and animating drawings. The 3.5 family continues this strength; for these use cases, Gemini’s multimodal performance is best-in-class.

9. The biggest problem: half the features don’t actually work yet. Claire encountered broken features, missing integrations, and “coming soon” disclaimers throughout testing. Workspace integration in AI Studio? Couldn’t access it. Avatar creation in Flow? Didn’t work. When you announce features that aren’t ready, people lose patience and stop trusting your roadmap.

If you’re enjoying these episodes, reply and let me know what you’d love to learn more about: AI workflows, hiring, growth, product strategy—anything.

Catch you next week,
Lenny

P.S. Want every new episode delivered the moment it drops? Hit “Follow” on your favorite podcast app.

2026-05-25 20:03:53

Felix Rieseberg is the engineering lead for Claude Cowork and Claude Code Desktop at Anthropic. He previously spent five years at Slack building developer tools. In this episode, Felix demonstrates how he uses Claude to solve real-life problems: analyzing floor plans to build interactive 3D house walkthroughs, automatically tracking promises he makes on Twitter, and building a $20 hardware device that physically approves Claude actions with a button press.

What you’ll learn:

1. How to use Claude Cowork to turn a 2D floor plan into an interactive 3D walkthrough where you can move furniture around

2. The “go one abstraction layer up” philosophy: why you should never manually enter data Claude can find itself

3. How to use your email as an inventory database for furniture, clothing, and personal purchases

4. When to use Opus vs. Sonnet 4.6 (hint: it’s about how well you can scope the problem, not technical complexity)

5. How live artifacts work and why they’re powerful for dashboards that refresh with real-time data from your connectors

6. The product philosophy behind making latency delightful

7. How to build your own $20 hardware device using Claude Code (no hardware experience required)

8. Why Felix never reads the code Claude writes and judges it purely on output

Brought to you by:

Magic Patterns—Prototypes that look like your product

Guru—The AI layer of truth

In this episode, we cover:

(00:00) Introduction to Felix Rieseberg

(02:40) Felix’s role at Anthropic

(03:25) The multiple tabs in Claude and why they exist

(05:55) Using Claude Cowork to design a new house using floor plans

(09:52) When to use Opus versus Sonnet 4.6

(12:37) Building an interactive 3D furniture planner

(14:30) Using your email as a source of truth for personal inventory

(15:58) The anti-to-do list: going one abstraction layer up

(23:14) Introduction to live artifacts

(26:02) Building a personal dashboard with live data

(28:37) Being polite to Claude (and why it matters for your humanity)

(30:28) Claude interaction tips

(32:33) Looking at the daily dashboard

(33:55) How live artifacts work with connectors

(35:02) Redesigning the dashboard

(37:55) The biggest gap: people don’t know what problems AI can solve

(41:52) The reverse interview

(42:30) Making latency delightful through asynchronous design

(44:05) The redesigned dashboard

(45:28) AI should free up your creative energy

(46:44) Building a $20 hardware Claude buddy

(52:33) Why kids are magical AI users

(54:30) Recap and final thoughts

Tools referenced:

• Claude Cowork: https://www.anthropic.com/product/claude-cowork

• Claude Code: https://claude.ai/code

• Claude for Chrome: https://code.claude.com/docs/en/chrome

• Claude Desktop: https://claude.ai/download

• Live Artifacts: https://support.claude.com/en/articles/14729249-use-live-artifacts-in-claude-cowork

• Connectors (Spotify, Gmail, Calendar, Notion): https://claude.ai/settings/connectors

• Slack: https://slack.com/

Where to find Felix Rieseberg:

Website: https://felixrieseberg.com/

LinkedIn: https://www.linkedin.com/in/felixrieseberg/

X: https://x.com/felixrieseberg

GitHub: https://github.com/felixrieseberg

Where to find Claire Vo:

ChatPRD: https://www.chatprd.ai/

Website: https://clairevo.com/

LinkedIn: https://www.linkedin.com/in/clairevo/

X: https://x.com/clairevo

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

2026-05-24 20:31:49

Dan Shipper is the co-founder and CEO of Every, a media and software company that’s become a living laboratory for the future of work. Everyone at his company of about 30 people is an AI early adopter; from editors to ops people, they use AI to do much of their work, giving Every a unique lens into where the world is heading. A year ago on this show, Dan predicted that people were sleeping on Claude Code for nontechnical work, which proved to be remarkably prescient. Today he’s back with another set of calls: the SaaS apocalypse is dumb, CLIs are over, the forward deployed engineer is the most valuable new hire, and the only thing you need to do to stay employed is ride the models.

Dan’s predictions:

1. The future of work will happen inside Codex or Claude Code.

2. Every company will have one “super-agent” inside their Slack that every employee talks to regularly.

3. SaaS is not dead—in fact, Dan is bullish on SaaS stocks. His contrarian take: “I would buy SaaS stocks right now.”

4. SaaS economics will shift: users will bring their own AI tokens into apps, which actually improves SaaS margins.

5. PMs will thrive in the AI era.

6. Full-stack designers will become superheroes.

7. The AI job apocalypse is not happening.

8. Forward deployed engineer is the new most essential role.

9. CLIs are over.

10. Automation is a lie.

11. We will read way more AI-generated writing and we will like it.

12. We’ll be building software for humans and agents to use together.

Brought to you by:

WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more

Vanta—Automate compliance, manage risk, and accelerate trust with AI

Where to find Dan Shipper:

• X: https://x.com/danshipper

• LinkedIn: https://www.linkedin.com/in/danshipper/

• Podcast: https://every.to/podcast

• Website: https://danshipper.com

Referenced:

• The AI-native startup: 5 products, 7-figure revenue, 100% AI-written code | Dan Shipper (co-founder/CEO of Every): https://www.lennysnewsletter.com/p/inside-every-dan-shipper

• Claude Cowork: https://claude.com/product/cowork

• Codex: https://chatgpt.com/codex

• Everyone should be using Claude Code more: https://www.lennysnewsletter.com/p/everyone-should-be-using-claude-code

• Every: https://every.to

• Kieran Klaassen on X: https://x.com/kieranklaassen

• Cora: https://cora.computer

• Kate Lee: https://every.to/@kate_1767

• METR (Model Evaluation and Threat Research): https://metr.org

• OpenClaw: https://openclaw.ai

• Shopify: https://www.shopify.com

• Ramp: https://ramp.com

• Brandon Gell on LinkedIn: linkedin.com/in/brandongell

• Proof: https://every.to/on-every/introducing-proof

• Devin: https://devin.ai

• Cursor: https://cursor.com

• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell

• SpaceX: https://www.spacex.com

• GitHub: https://github.com

• Lenny’s post on X on AI changing job responsibilities: https://x.com/lennysan/status/2054664138039992600

• General Assembly: https://generalassemb.ly

• Marcus Moretti: https://every.to/@marcus_fd8302_1

• Spiral: https://every.to/on-every/introducing-spiral

• Axios: https://www.axios.com

• Hermes: https://hermes-agent.nousresearch.com

• Viktor: https://www.viktor.ai

• The Dark Wizard on HBO: https://www.hbomax.com/shows/dark-wizard/76e78c26-21c9-45b4-b84b-4c3e1f8ff763

• Alex Honnold: https://en.wikipedia.org/wiki/Alex_Honnold

• 100 Foot Wave on HBO Max: https://www.hbomax.com/shows/100-foot-wave/34e489ad-2eca-4078-adb6-6d2b521b407e

• Rob Burbea talks: https://www.youtube.com/@boubabuddha/playlists

• David Goggins: https://en.wikipedia.org/wiki/David_Goggins

Recommended books:

• The Golden Compass: https://www.amazon.com/Golden-Compass-His-Dark-Materials/dp/0807204714

• The Writing Life: https://www.amazon.com/Writing-Life-Annie-Dillard/dp/0060919884

• The Second World War: https://www.amazon.com/Second-World-War-Volumes/dp/B005NS30ZG

• The Rigor of Angels: Borges, Heisenberg, Kant, and the Ultimate Nature of Reality: https://www.amazon.com/Rigor-Angels-Heisenberg-Ultimate-Reality/dp/0593315073

• The Power Broker: Robert Moses and the Fall of New York: https://www.amazon.com/Power-Broker-Robert-Moses-Fall/dp/0394720245

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

Lenny may be an investor in the companies discussed.

My biggest takeaways from this conversation:

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2026-05-24 04:33:09

👋 Hello and welcome to this week’s edition of ✨ Community Wisdom ✨ a subscriber-only email, delivered every Saturday, highlighting the most helpful conversations in our members-only Slack community.

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2026-05-22 23:41:05

After a year of bringing you these audio versions of my newsletter, I’ve decided it’s time to wind down this experiment.

It’s been a lot of fun making these episodes and it’s been incredible to see how far the technology has developed!

I’m going to keep all of the Lenny’s Reads episodes up on this channel for another week.

Thank you so much for listening, it's been great having you along for the ride.

If you want to keep up with all my content, make sure to keep up to date here:

• Twitter: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

• Podcast: https://www.youtube.com/@LennysPodcast

• Newsletter: http://lennysnewsletter.com/

I'll see you there.