2026-04-13 23:07:46
Listen now on YouTube • Spotify • Apple Podcasts
Brought to you by:
Guru—The AI layer of truth
ThoughtSpot—Build AI-powered analytics into your product
In this episode, Claire talks with Yash Tekriwal, the head of education at Clay, about how he built a custom AI-powered Slack inbox that turns 150 daily notifications into around 30 that actually matter. Instead of reacting to messages, Yash designed a system that categorizes, prioritizes, and routes everything into a clean, actionable workflow. They walk through exactly how he built it using Perplexity Computer and OpenClaw, why most people are using AI wrong (doing tasks instead of building systems), and how anyone—technical or not—can start creating their own personalized software stack.
Yash receives 100 to 150 Slack notifications daily, but only 30 to 40 require real action. By categorizing messages into DMs, group mentions, threads, and channel mentions, then sub-categorizing into action-required, need-to-read, and FYI, he transformed anxiety-inducing notification overload into a manageable workflow.
Use AI to build deterministic tools, not just to do tasks. There’s a crucial difference between asking AI to categorize things repeatedly versus using it to build code that handles structured data through APIs. Yash used OpenClaw to build a Slack digest that pulls notifications via API endpoints—AI built the tool once, but the categorization runs on deterministic code (except for the final action/read/FYI sorting).
Perplexity Computer’s multi-model orchestration removes you from the loop. Unlike Claude Code or Codex, Perplexity automatically uses different models for different subtasks: Sonnet for fetching data, Gemini for planning and coding, Opus for complex builds. This eliminates the frustrating back-and-forth of “good try, but it doesn’t work; try again” that plagues single-model coding agents.
Perplexity Computer’s cloud deployment and native connectors are game changers. Unlike local coding agents, Computer runs in the cloud with pre-authenticated connectors to Gmail, Slack, Notion, Asana, and more. Apps are automatically deployed and shareable via URL—no GitHub repos, no Vercel deployment, no technical overhead. This makes it accessible to non-technical builders.
The anti-to-do list framework: spend an hour daily automating what you never want to do again. Instead of a to-do list, maintain an anti-to-do list of tasks you despise (manually deleting email spam, entering meeting action items into Asana, triaging unread Slack messages). Dedicate time to systematically eliminate these tasks through automation.
SaaS isn’t dying; it’s about to explode into micro-software. Yash says the narrative that AI will kill SaaS is backward. Instead, we’ll see a Cambrian explosion of specialized software built on top of existing platforms. Yash would happily pay $15 a month for someone to maintain his Slack digest as a product—and thinks thousands of similar micro-businesses will emerge serving narrow use cases that were never venture-scale before.
The future of productivity is personalized software. Every knowledge worker will eventually have custom apps optimized for their specific mental model and workflow. These won’t replace SaaS platforms but extend them, filling the gap between what Slack/Notion/Asana provide and what each individual actually needs to work at their best.
How I AI: Yash Tekriwal on Taming Slack with a Custom AI-Built Dashboard: https://www.chatprd.ai/how-i-ai/taming-slack-with-a-custom-ai-built-dashboard
How to Turn a Text Digest into an Interactive Kanban Dashboard: https://www.chatprd.ai/how-i-ai/workflows/how-to-turn-a-text-digest-into-an-interactive-kanban-dashboard
How to Prototype a Website Redesign Using an AI with Browser Access: https://www.chatprd.ai/how-i-ai/workflows/how-to-prototype-a-website-redesign-using-an-ai-with-browser-access
How to Build a Custom AI-Powered Text Digest for Slack Notifications: https://www.chatprd.ai/how-i-ai/workflows/how-to-build-a-custom-ai-powered-text-digest-for-slack-notifications
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In this episode, Claire talks with JJ Englert, the enablement and community lead at Tenex, about how he uses Claude Cowork to build a fully automated daily operating system that drafts emails, reviews his work, plans his day, and coordinates across his tools. They walk step-by-step through how to set it up—from creating a “brain” file that teaches AI how you think, to building reusable skills that write exactly like you, to running daily briefings that prepare your entire day before you even open your laptop.
Cowork is the first real bridge for non-technical knowledge workers to move beyond chat and actually have AI do things for them. While chat tools like ChatGPT tell you what to do, Cowork actually does it: drafting emails, organizing files, managing your calendar, and more. It’s the middle ground between passive chat and full coding in Claude Code, and it’s designed for people who want AI to be productive without learning terminal commands.
Start every project with a “brain” file that tells Claude who you are, how you work, and who you work with. JJ’s secret weapon is a Markdown file that contains detailed instructions about his working preferences, team members, communication style, and more. Every time he starts a new task in that project, Claude reads this file and immediately understands his context. This eliminates the need to re-explain yourself every time and ensures consistent, personalized results. It’s like having a coworker who already knows everything about you.
Always include good examples and bad examples when building skills. AI doesn’t know what success looks like for you unless you show it. When you get an output you love, save it as a good example. When you get something off-brand or low-quality, save it as a bad example with a note: “Don’t do this again.” Over time, Claude learns your subjective preferences and delivers increasingly consistent results.
Build an anti-to-do list—things you never want to do again—and then automate them with skills. JJ recommends thinking about the repetitive tasks that drain your energy: first-drafting emails, preparing for meetings, writing social posts, organizing files. Each of those becomes a skill. Over time, you build a library of skills that handle the mundane work, freeing you to focus on creative and strategic decisions. The goal isn’t to eliminate your job; it’s to eliminate the parts of your job you hate.
Cowork teaches you skills that transfer directly to Claude Code. JJ uses Cowork for business productivity and Claude Code for building. But Cowork is a great on-ramp because it introduces concepts like projects, skills, and file management without requiring you to use the terminal. As you get comfortable orchestrating agents and managing context in Cowork, you’re learning the mental models that make you effective in Code.
Projects don’t have to be work-related—use them for house maintenance, wedding planning, recruiting, or anything else. You can create a house maintenance project with reminders to change air filters, seasonal checklists, and remodel plans. Whether a wedding planning project that finds vendors, drafts emails, and manages timelines, or a recruiting project with job descriptions, interview guides, and onboarding docs, the pattern is the same: organize context in a folder, connect it to Cowork, build skills, and let AI do the work.
How I AI: JJ Englert’s Guide to a ‘Daily Operating System’ with Claude Cowork: https://www.chatprd.ai/how-i-ai/jj-englerts-guide-to-a-daily-operating-system-with-claude-cowork
Build a Multi-Persona ‘Sub-Advisory Board’ for Instant Feedback: https://www.chatprd.ai/how-i-ai/workflows/build-a-multi-persona-sub-advisory-board-for-instant-feedback
Train Claude Cowork to Write Emails in Your Personal Style: https://www.chatprd.ai/how-i-ai/workflows/train-claude-cowork-to-write-emails-in-your-personal-style
How to Set Up a ‘Daily Operating System’ in Claude Cowork: https://www.chatprd.ai/how-i-ai/workflows/how-to-set-up-a-daily-operating-system-in-claude-cowork
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.
2026-04-13 20:03:52
JJ Englert leads community enablement at Tenex. In this episode, JJ provides a complete zero-to-one tutorial on Claude Cowork, Anthropic’s desktop tool that sits between simple chat and full terminal-based coding.
Listen or watch on YouTube, Spotify, or Apple Podcasts
How to create your first Claude Cowork project by connecting a folder on your computer and building context over time
The “brain” file strategy: how to create a preferences document that Claude reads every time to understand who you are and how you work
Why one-click connectors to Gmail, Slack, Notion, and Google Calendar unlock AI that actually does work instead of just suggesting it
How to analyze your sent emails to build a writing skill that perfectly matches your tone and style
The sub-advisory-board technique: spinning up three AI agents with different personas to review your work from multiple perspectives
How to set permissions for each connector so Claude only drafts (never sends) or always asks before taking action
The scheduled-task workflow that creates a morning debrief by reading your email, Slack, and calendar every day at 7:30 a.m.
Why projects with shared memory beat individual chat threads for consistent, high-quality AI outputs
Tines—Start building intelligent workflows today
Cursor—The best way to code with AI
(00:00) Introduction to JJ Englert
(02:48) What Cowork is and who it’s for
(05:49) Getting started: Opening the Cowork tab in Claude Desktop
(07:04) Understanding projects as folders on your computer
(07:54) Creating your “brain” file, with working preferences and context
(10:24) Demo: Building a daily operating system project from scratch
(12:18) How to prompt Cowork when starting a new project
(14:54) Understanding the project interface and shared memory
(18:37) Setting up connectors to Gmail, Slack, Google Calendar, and other tools
(21:00) Using connectors to analyze your emails and build personalized writing skills
(24:21) Creating a thinking-partner skill for decision support
(26:18) Cowork vs. OpenClaw
(27:18) Building a sub-advisory skill with multiple AI personas for feedback
(34:03) Advanced skill example: Multi-step newsletter creation with research and evaluation
(36:08) Setting up scheduled tasks for morning debriefs
(37:57) Going beyond one-off tasks with AI
(41:00) Progressive trust and the tradeoff of information for productivity
(44:08) Different use cases beyond work productivity
(46:08) Lightning round
• Claude Code: https://claude.ai/code
• Wispr Flow: https://whisperflow.ai/
• Monologue: https://www.monologue.to/
• Domo: https://www.domo.com/
• Pencil.dev: https://pencil.dev/
• Remotion: https://www.remotion.dev/
• Obsidian: https://obsidian.md/
• OpenClaw: https://openclaw.ai/
• Notion: https://notion.so/
• Get Started with Claude Cowork: https://support.claude.com/en/articles/13345190-get-started-with-cowork
YouTube: https://www.youtube.com/channel/UCv2ovDhYVtlJw4QMidLFP8Q
X: https://twitter.com/jjenglert
LinkedIn: https://www.linkedin.com/in/jj-englert-a08836a6/
ChatPRD: https://www.chatprd.ai/
Website: https://clairevo.com/
LinkedIn: https://www.linkedin.com/in/clairevo/
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
2026-04-12 20:31:41
Keith Rabois was an early executive at PayPal (part of the famous PayPal Mafia), COO at Square, VP of Corporate Development at LinkedIn, and an early investor in Stripe, DoorDash, Airbnb, YouTube, Ramp, and Palantir. Currently he’s managing director at Khosla Ventures. Also, he hasn’t touched a computer since September 2010 (he does everything from an iPad).
Listen on YouTube, Spotify, and Apple Podcasts
The barrels vs. ammunition hiring framework (and how to spot barrels)
Why talking to customers is actively harmful for consumer products
How to identify undiscovered talent
Why the PM role is dying
The three traits of the best-performing companies right now
The specific interview question he asks every senior candidate
Why CMOs (not engineers) are becoming the #1 consumer of tokens
WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs
Vanta—automate compliance, manage risk, and accelerate trust with AI
• X: https://x.com/rabois
• LinkedIn: linkedin.com/in/keith
• Website: https://www.khoslaventures.com
• Square: https://squareup.com
• Jack Dorsey on X: https://x.com/jack
• Head of Claude Code: What happens after coding is solved | Boris Cherny: https://www.lennysnewsletter.com/p/head-of-claude-code-what-happens
• Simon Willison’s Weblog: https://simonwillison.net
• Vinod Khosla on X: https://x.com/vkhosla
• Peter Thiel on X: https://x.com/peterthiel
• Max Levchin on X: https://x.com/mlevchin
• David Sacks on LinkedIn: https://www.linkedin.com/in/davidoliversacks
• Tony Xu on X: https://x.com/t_xu
• David Sze on X: https://x.com/davidsze
• Faire: https://www.faire.com
• Max Rhodes on X: https://x.com/MaxRhodesOK
• Jeffrey Kolovson on LinkedIn: https://www.linkedin.com/in/jeffreykolovson
• Uncapped | Comparative Advantages w/ Keith Rabois: https://www.khoslaventures.com/posts/uncapped-comparative-advantages-w-keith-rabois
• Lattice: https://lattice.com
• Taylor Francis on LinkedIn: https://www.linkedin.com/in/taylor-francis-4ba49640
• Building product at Stripe: craft, metrics, and customer obsession | Jeff Weinstein (Product lead): https://www.lennysnewsletter.com/p/building-product-at-stripe-jeff-weinstein
• The art of hiring: insights from Khosla Ventures, Airbnb, Ramp and Traba: https://ramp.com/velocity/the-art-of-hiring-insights
• Eric Glyman: Seek out super individual contributors (ICs): https://ramp.com/velocity/the-art-of-hiring-insights#Eric-Glyman:-Seek-out-super-individual-contributors-(ICs)
• Eric Glyman on X: https://x.com/eglyman
• Mike Moore on LinkedIn: https://www.linkedin.com/in/mike-moore-802223177
• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach
• Why you should work much harder RIGHT NOW: https://marginalrevolution.com/marginalrevolution/2026/03/why-you-should-work-much-harder-right-now.html
• Opendoor: https://www.opendoor.com
• The Craft of Early Stage Venture | Peter Fenton, General Partner at Benchmark | Uncapped with Jack Altman: https://www.youtube.com/watch?v=vRiblwiXt-Q
• Lovable: https://lovable.dev
• The rise of the professional vibe coder (a new AI-era job) | Lazar Jovanovic (Professional Vibe Coder): https://www.lennysnewsletter.com/p/getting-paid-to-vibe-code
• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (co-founder and CEO): https://www.lennysnewsletter.com/p/building-lovable-anton-osika
• Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom
• Jeremy Stoppelman on X: https://x.com/jeremys
• The design process is dead. Here’s what’s replacing it. | Jenny Wen (head of design at Claude): https://www.lennysnewsletter.com/p/the-design-process-is-dead
• Andy Warhol: https://en.wikipedia.org/wiki/Andy_Warhol
• Curation and Algorithms: https://stratechery.com/2015/curation-and-algorithms
• Ernest Hemingway: https://en.wikipedia.org/wiki/Ernest_Hemingway
• William Shakespeare: https://en.wikipedia.org/wiki/William_Shakespeare
• Evan Moore on X: https://x.com/evancharles
• Andrew Mason on X: https://x.com/andrewmason
• Read Taylor Swift’s Full Viral Speech After Record-Breaking Awards Sweep: https://www.newsweek.com/entertainment/read-taylor-swift-full-acceptance-speech-record-breaking-awards-sweep-11745941
• The Chainsmokers: Stories Behind the Songs, AI’s Impact on Music, and Venture Investing | Uncapped with Jack Altman: https://www.youtube.com/watch?v=9GMSC-2pYnw&list=PLtpH7YnTL8ihy0nR2BV32n5VkRtqlDAS1&index=16
• How to spot a top 1% startup early: https://www.lennysnewsletter.com/p/how-to-spot-a-top-1-startup-early
• David Weiden on LinkedIn: https://www.linkedin.com/in/davidweiden
• Alfred Lin on LinkedIn: https://www.linkedin.com/in/linalfred
• Keith’s post about vertical integration on X: https://x.com/rabois/status/870673635375104000
• Jon Chu on X: https://x.com/jonchu
• Kanu Gulati on X: https://x.com/KanuGulati
• Rogo: https://rogo.ai
• Profound: https://www.tryprofound.com
• Basis: https://www.getbasis.ai
• Spellbook: https://www.spellbook.legal
• Roelof Botha on X: https://x.com/roelofbotha
• Delian Asparouhov on LinkedIn: https://www.linkedin.com/in/delian-asparouhov-87447742
• Lessons From Keith Rabois, Essay 1: How to become a Venture Capitalist: https://delian.io/lessons-1
• Velocity over everything: How Ramp became the fastest-growing SaaS startup of all time | Geoff Charles (VP of Product): https://www.lennysnewsletter.com/p/velocity-over-everything-how-ramp
• Nuremberg on AppleTV+: https://tv.apple.com/us/movie/nuremberg/umc.cmc.3sg4y0382byupy76bfy7307k4
• Eight Sleep: https://www.eightsleep.com
• “NO DAYS OFF”—Bill Belichick on X: https://x.com/SNFonNBC/status/829036279069364224
• Creativity, Inc.: Overcoming the Unseen Forces That Stand in the Way of True Inspiration: https://www.amazon.com/Creativity-Inc-Overcoming-Unseen-Inspiration/dp/0812993012
• The Jordan Rules: The Inside Story of One Turbulent Season with Michael Jordan and the Chicago Bulls: https://www.amazon.com/Jordan-Rules-Sam-Smith/dp/0671796666
• The Upside of Stress: Why Stress Is Good for You, and How to Get Good at It: https://www.amazon.com/Upside-Stress-Why-Good-You/dp/1101982934
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.
2026-04-12 03:36:51
👋 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.
2026-04-08 20:03:47
Yash Tekriwal is the head of education at Clay. A self-described hyper-optimizer, Yash has built multiple custom productivity applications using Perplexity Computer and OpenClaw to manage his overwhelming daily workflow—including a Slack digest system that categorizes over 150 daily notifications into actionable priorities, and a consolidated news/email/Slack dashboard that serves as his personal command center.
Listen or watch on YouTube, Spotify, or Apple Podcasts
How Yash built a custom Slack digest that categorizes 150+ daily notifications into action-required, need-to-read, and FYI buckets
Why Perplexity Computer beats Claude Code and Codex for building personal productivity apps
His “anti-to-do list” framework: spending an hour daily automating tasks you never want to do again
How to use AI for deterministic tasks (APIs, structured data) vs. subjective tasks (categorization, summarization)
Why the SaaS apocalypse narrative is wrong—and why we’re about to see an explosion of micro-software
How his team uses Perplexity Computer to prototype design systems and communicate with cross-functional partners
Guru—The AI layer of truth
ThoughtSpot—Build AI-powered analytics into your product
(00:00) Introduction to Yash
(02:38) The burden of 150 daily Slack notifications
(05:45) When to use AI for tasks vs. building deterministic code
(06:38) Building the Slack digest with OpenClaw
(11:33) Introducing Perplexity Computer and the visual dashboard
(14:28) Three reasons Perplexity Computer beats Claude Code
(16:14) Using connectors to automate meeting follow-ups across Notion and Asana
(18:21) The Kanban-style Slack dashboard
(20:15) The long tail of customer requests and the future of micro-software
(24:09) The anti-to-do list framework
(26:21) Building a consolidated news, email, and Slack digest
(29:48) How Perplexity Computer handles authentication and deployment
(31:46) Team use case: Prototyping persona-based learning journeys for Clay University
(35:49) Lightning round and final thoughts
• Perplexity Computer: https://www.perplexity.ai/computer/new
• OpenClaw: https://openclaw.ai/
• Discord: https://discord.com/
• Claude Code: https://claude.ai/code
• Codex: https://openai.com/codex/
• Asana: https://asana.com/
• Airtable: https://airtable.com/
• Figma: https://www.figma.com/
• Vercel: https://vercel.com/
• ChatGPT: https://chat.openai.com/
• Slack: https://slack.com/
• Notion: https://www.notion.so/
• Superhuman: https://superhuman.com/
• Clay University: https://www.clay.com/university
• Kanban boards: https://en.wikipedia.org/wiki/Kanban_board
LinkedIn: https://www.linkedin.com/in/yashtekriwal/
Company: https://www.clay.com/
ChatPRD: https://www.chatprd.ai/
Website: https://clairevo.com/
LinkedIn: https://www.linkedin.com/in/clairevo/
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
2026-04-08 10:51:13
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Add the private feed to your podcast app at add.lennysreads.com
In this episode, my wife Michelle Rial, cartoonist and author, celebrates the launch of her new book Charts for Babies by sharing a pep talk for anyone stuck in a creative rut. She walks through 12 tried-and-tested steps designed to lift you out of a creative block and get back to making things that matter.
In this episode, you’ll learn:
Why it’s necessary to create work that might feel embarrassing
The simple mindset shift that stops stalling and gets you to just start
How to reframe scorn as a positive signal
The thought process that can help you move out of a state of rumination
How to treat failed ideas as seeds for future breakthroughs
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