Lenny's Podcast

Ryan Singer is one of the earliest employees and the former Head of Strategy at 37signals (the makers of Basecamp), where he spent nearly two decades refining a product development approach that helped the company build super-successful products with small teams. Based on these lessons, he wrote "Shape Up: Stop Running in Circles and Ship Work that Matters," and Ryan now works with companies of all sizes to help them escape the cycle of endless sprints, missed deadlines, and dragging projects. What you’ll learn: 1. Why traditional Agile and Scrum methods often lead teams into endless cycles of work without meaningful shipping milestones. 2. The “appetite-driven” approach to product development where teams set fixed timeboxes (usually six weeks maximum) and vary the scope instead of expanding timelines. 3. The exact process for running effective “shaping” sessions that collaboratively define projects before committing resources. 4. Why most teams struggle with too little detail in their planning, not too much. 5. Why a 30-to-50-person team size is the critical breaking point when growing startups need to adopt more structured processes. 6. Practical techniques for bridging the engineering-design divide by bringing technical and product perspectives together earlier in the process. 7. The powerful “breadboarding” and “fat marker sketching” techniques that help teams align on solutions without getting lost in high-fidelity details. 8. The clear warning signs that your current development process is failing before it’s too late to change course. 9. Proven strategies to implement Shape Up methods, whether you’re working in a startup or enterprise environment. 10. A step-by-step approach to transitioning from Scrum to Shape Up by piloting the methodology with a single team before broader implementation. 11. Why the PM role shifts upstream in Shape Up, focusing more on problem definition than project management. 12. How to adapt Shape Up principles to your company’s unique context, even if it’s nothing like Basecamp. — Brought to you by: • WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs: https://workos.com/lenny • Merge—A single API to add hundreds of integrations into your app: http://merge.dev/lenny • Airtable ProductCentral—Launch to new heights with a unified system for product development: https://www.airtable.com/lenny Find the transcript at: https://www.lennysnewsletter.com/p/shape-up-ryan-singer Where to find Ryan Singer: • X: https://x.com/rjs • LinkedIn: https://www.linkedin.com/in/feltpresence/ • Website: https://www.ryansinger.co/ • Course: https://www.ryansinger.co/srl/ Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ In this episode, we cover: (00:00) Ryan’s background (04:38) The origins of Shape Up (07:40) Implementing Shape Up in different companies (09:56) How Shape Up is different (19:02) The core elements of Shape Up (26:29) Shaping sessions and timeboxing (37:23) Flexible sprint planning (38:56) The output of a shaping session (46:57) Balancing detail and flexibility (53:50) A deep dive into shaping sessions (01:01:32) Fat marker sketches (01:02:48) Getting started using Shape Up (01:13:20) Signs it's time to try the Shape Up method (01:18:25) Feature factories (01:25:59) The role of the PM in Shape Up (01:28:26) What makes Basecamp unique (01:35:55) The second edition of the book (01:38:30) Linking product strategy and shaping (01:41:53) Conclusion and final thoughts Referenced: • Basecamp: https://basecamp.com/ • David Heinemeier Hansson on LinkedIn: https://www.linkedin.com/in/david-heinemeier-hansson-374b18221/ • Jason Fried on LinkedIn: https://www.linkedin.com/in/jason-fried/ • Jason Fried challenges your thinking on fundraising, goals, growth, and more: https://www.lennysnewsletter.com/p/jason-fried-challenges-your-thinking • Des Traynor on LinkedIn: https://www.linkedin.com/in/destraynor/ • Intercom: https://www.intercom.com/ ...References continued at: https://www.lennysnewsletter.com/p/shape-up-ryan-singer Recommended books: • Shape Up: Stop Running in Circles and Ship Work That Matters: https://basecamp.com/shapeup • Demand-Side Sales 101: Stop Selling and Help Your Customers Make Progress: https://www.amazon.com/Demand-Side-Sales-101-Customers-Progress/dp/1544509987/ • Competing Against Luck: The Story of Innovation and Customer Choice: https://www.amazon.com/Competing-Against-Luck-Innovation-Customer/dp/0062435612/ • Job Moves: 9 Steps for Making Progress in Your Career: https://www.amazon.com/Job-Moves-Making-Progress-Career/dp/0063283581 Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. Lenny may be an investor in the companies discussed.

Become an Epic Product Engineer is Kent C. Dodds's interview podcast about skills that stay valuable as AI takes on more implementation. It's all about product engineering. Blending technical depth with product judgment, user empathy, and problem clarity. Each episode is a long-form conversation with a guest who has shipped real software and cares about building the right thing before making it right. You get full audio, transcripts, structured show notes, homework (one concrete action to try), and links from the conversation. Canonical home for the show and every episode page: https://www.epicproduct.engineer/become-an-epic-product-engineer-podcast New episodes publish on Wednesdays. Complements Better with Kent — Kent's solo series on durable skills for people who ship software.

600+ episodes to help you launch and grow your startup Whether you’ve launched your startup or you're just thinking about it, learn from successful founders who have been in your shoes. Subscribe & Review: iTunes: https://podcasts.apple.com/us/podcast/startups-for-the-rest-of-us/id366931951 Spotify: https://open.spotify.com/show/2Ww2e4JNO2cfxWC2ImR7DJ Stitcher: https://www.stitcher.com/podcast/startups-for-the-rest-of-us

A podcast by 37signals about the better way to work and run your business. Featuring Jason Fried and David Heinemeier Hansson, cofounders of 37signals (makers of Basecamp and HEY) and authors of books REWORK and It Doesn't Have to Be Crazy at Work. Hosted by 37signals' employee Kimberly Rhodes.

An LLM is an incredibly powerful brain that knows everything about humanity and nothing about you or the software you run. This video walks through the four buzzwords that turn that raw brain into a system you can trust: agent harness, loop engineering, LLM Ops, and eval. No jargon, step by step, technical or not. You can build anything. You can learn anything. 💪 Timeline 0:00 Intro: the 4 AI agent buzzwords 0:42 What an AI agent run actually is 1:52 The memory system: procedural, semantic, episodic 3:37 What "harness" really means (the horse) 5:07 Storing and updating memory (databases, skills, summarizer agent) 8:28 Retrieval: RAG, SQL vs semantic search 10:00 Tool calling and why agents loop 10:52 Loop engineering and end-loop guardrails 13:21 A Claude Code hooks example 14:18 Eval and LLM Ops: why you need them 15:55 Tracing every run (Langfuse, LangSmith) 16:43 Evaluation: LLM as a judge 17:20 Diagnosing what broke 18:16 The gate: ship the fix or fix the bug 18:57 Zoom out: the full system 19:53 Wrap up Launch Full-Stack App Template: https://github.com/ShenSeanChen/launch-mvp-stripe-nextjs-supabase My AI Agent Startup AutoManus.io is an AI sales lead manager for made-to-order product sales. We embed directly where conversations happen (WhatsApp, email, web chat) to capture inbound, automate follow‑ups, and kill CRM busywork; live with 4 pilots and 2 contracts in motion, pre‑seed backed by Character VC. Focused on US/UK/Germany, raising to expand engineering and scale deployments. ☕️ Buy me a coffee: https://buy.stripe.com/5kA176bA895ggog4gh - X: https://x.com/ShenSeanChen - Sean's Discord: https://discord.gg/tvECErKcFr - AutoManus Discord: https://discord.gg/5HhcNjCR - LinkedIn: https://linkedin.com/in/shen-sean-chen - Github Link: https://github.com/ShenSeanChen - Instagram: https://www.instagram.com/sean_ai_stories Sub Count when launched: 13,050 Top Github Repos - LaunchMVP NextJS,Supabase,Stripe (1015 stars): https://github.com/ShenSeanChen/launch-mvp-stripe-nextjs-supabase - ReactNextJSTips (114 stars): https://github.com/ShenSeanChen/yt-react-nextjs-tips - DeepResearchAgentBackend (70 stars): https://github.com/ShenSeanChen/yt-DeepResearch-Backend - SupabaseTipsKanban (64 stars): https://github.com/ShenSeanChen/yt-supabase-tips-kanban - RAGVectorDB (56 stars): https://github.com/ShenSeanChen/yt-rag - KimiK2Claude (37 stars): https://github.com/ShenSeanChen/yt-kimi-k2-claude - DeepResearchAgentFrontend (33 stars): https://github.com/ShenSeanChen/yt-DeepResearch-Frontend - AgenticRAG (13 stars): https://github.com/ShenSeanChen/yt-agentic-rag You Can Build Anything Playlist (Full-Stack Dev Without CS Degrees) - Core7: 95% React/NextJS Use Cases https://www.youtube.com/watch?v=vZzFlAjz4rA&list=PLE9hy4A7ZTmpGq7GHf5tgGFWh2277AeDR&index=16 - Core6: 95% Supabase Use Cases https://www.youtube.com/watch?v=Pnoq2tIif3s&list=PLE9hy4A7ZTmpGq7GHf5tgGFWh2277AeDR&index=15 - Core5: StripeNextJSSupabase https://www.youtube.com/watch?v=ad1BxZufer8&list=PLE9hy4A7ZTmpGq7GHf5tgGFWh2277AeDR&index=8 - Core4: AuthSupabaseGoogle https://www.youtube.com/watch?v=AZAU3ClAWWE&list=PLE9hy4A7ZTmpGq7GHf5tgGFWh2277AeDR&index=6 - Core3: FastapiGCPPro https://www.youtube.com/watch?v=u3sfqpzzo-U&list=PLE9hy4A7ZTmpGq7GHf5tgGFWh2277AeDR&index=5 - Core2: SupabaseHero https://www.youtube.com/watch?v=V0kmgkyPsVQ&list=PLE9hy4A7ZTmpGq7GHf5tgGFWh2277AeDR&index=4 - Core1: LaunchAnApp https://www.youtube.com/watch?v=iQ2izvGG4tQ&list=PLE9hy4A7ZTmpGq7GHf5tgGFWh2277AeDR&index=3 - Launch WhereToMeet w/ GoogleMaps, Calendar, Supabase, Cursor: https://www.youtube.com/watch?v=5xMjX1QxGUY&list=PLE9hy4A7ZTmpGq7GHf5tgGFWh2277AeDR&index=2 - Launch EncourageMe w/ Cursor, Supabase, Vercel https://www.youtube.com/watch?v=hnvL4xa2DHA&list=PLE9hy4A7ZTmpGq7GHf5tgGFWh2277AeDR

In this episode, I sit down with Alex Finn for a full, screen-shared walkthrough of Hermes Desktop, the new desktop home for the Hermes AI agent. I open with a clear challenge: by the end, sell me on installing Hermes Desktop, show me real ways to make money and stay productive, and explain his move from OpenClaw. Alex tours every major surface — sessions, profiles, artifacts, skills, cron jobs, and sub-agents — and shares money-saving tactics at each step. We close on the idea that matters most to me: aiming these agents at other people's challenges as the clearest path to real value. Timestamps 00:00 – Intro 04:04 – Sessions and Context Management 06:10 – Profiles Explained 08:49 – Model-Based vs Role-Based Profiles 12:58 – Artifacts as a Second Brain 14:32 – Why Alex Switched From OpenClaw 17:32 – Skills, Tools, and Tool Sets 19:19 – Messaging and Cron Setup 21:44 – Reverse Prompting and the Brain Dump 28:09 – Sub-Agents vs Profiles 32:12 – Putting It Together: Solving Challenges 32:38 – The Daily Business Opportunity Scan 37:05 – Local Models: Mac Studio vs DGX Spark 39:03 – Reframing Cost as Investment 41:59 – The Real Way to Make Money With Hermes 42:51 – Closing Thoughts Key Points * Hermes Desktop pulls sessions, profiles, artifacts, skills, and cron jobs into one polished, Apple-style interface. * Smart session and context management keeps each message slim and keeps monthly costs low. * Profiles map to different models — Opus 4.8 for strategy, ChatGPT 5.5 for coding, a local Qwen model for free research — so each task runs on its best fit. * Reverse prompting plus a personal brain dump produces far stronger prompts, cron jobs, and outputs. * Sub-agents handle one skill across many parallel tasks; profiles handle work where each step needs a distinct skill set. * The biggest opportunity: aim your agent at Reddit and X to surface real problems you are positioned to solve. Numbered Section Summaries 1. The Moment Hermes Overtook OpenClaw Alex shares his screen and calls Hermes Desktop the best AI agent experience available right now, framing the recent release as the moment Hermes pulled ahead. He compares the focused, polished Hermes updates to Apple and the broader OpenClaw approach to Android, and notes his switch came purely for the love of the game. 2. Sessions and Context Management Alex shows how each new chat opens its own session, keeping context clean and separated by topic. He explains that slim context keeps every message small, and small messages keep monthly bills modest — his top money-saving tip. 3. Profiles Mapped to Models Profiles are separate Hermes agents, each with its own skills, a soul.md personality, and its own memories. Alex organizes his by model — Opus 4.8 for high-level strategy, ChatGPT 5.5 for coding, and a local Qwen model for free, fast research — and picks the profile whose strengths match the task. 4. Artifacts as a Productized Second Brain Artifacts gathers every link, image, and file you send your agent into one searchable place. Alex drops links to his "Librarian" profile and lets Artifacts file them automatically, which turns the agent into a tidy, searchable second brain. 5. Skills, Tools, and the Cron Section Alex walks the Skills interface, where 150-plus skills ship out of the box and you keep only the ones you use to trim context and cost. He highlights tool sets as a fresh way to group skills together, and praises the Cron section for giving one-click confirmation that scheduled tasks truly exist. 6. Reverse Prompting and the Brain Dump My favorite tip from Alex: brain dump everything about yourself — interests, goals, skills — then ask the agent for the best prompt to use. He demos it live by building a morning brief, and the reverse prompt returns a detailed, well-formatted instruction that pulls fresh, real headlines, prices, and scores from the last 24 hours. 7. Sub-Agents vs Profiles Alex clarifies the difference: sub-agents are copies of your main agent that share its skills, ideal for running one skill across many parallel tasks, like building several features of a micro-SaaS at once. Profiles each carry distinct skill sets and memories, ideal when a job needs a researcher, a writer, and a designer working in sequence. The #1 tool to find startup ideas/trends - https://www.ideabrowser.com/ LCA helps Fortune 500s and fast-growing startups build their future - from Warner Music to Fortnite to Dropbox. We turn 'what if' into reality with AI, apps, and next-gen products https://latecheckout.agency/ The Vibe Marketer - Resources for people into vibe marketing/marketing with AI: https://www.thevibemarketer.com/ FIND ME ON SOCIAL X/Twitter: https://twitter.com/gregisenberg Instagram: https://instagram.com/gregisenberg/ LinkedIn: https://www.linkedin.com/in/gisenberg/ FIND ALEX ON SOCIAL Youtube: https://www.youtube.com/@AlexFinnOfficial/videos X/Twitter: https://x.com/AlexFinnX Creator Buddy: https://www.creatorbuddy.io/