Lenny’s Podcast91 min
David Placek · Jun 29, 2025
Key learnings- Expect that you won't recognize the right name immediately; Placek says clients almost always believe they will, but it rarely…
- Treat a strong brand name as a long-lasting asset, since it is used more often and for longer than design, messaging, or…
- Seek distinctiveness over descriptiveness; a descriptive name like 'Cloud Pro' blends into a crowded market, while a distinctive…
Lenny’s Newsletter♥ 528
Jun 24, 2025 · 14 min
Subscriber post — summary onlyA glossary explaining 20+ common AI terms in simple language, from models and LLMs to transformers, training, RLHF, RAG, evals, agents, and hallucinations. It aims to help readers follow AI conversations in meetings and…
Lenny’s Podcast153 min
Peter Deng · Jun 22, 2025
Key learnings- Before scaling past product-market fit, invest in systems and architecture that let the team move sustainably faster, since…
- Build a growth team early; a growth leader forces instrumentation and rigorous questioning of what is actually happening in the…
- Balance growth-focused and craft-focused people deliberately, so the tension between metrics and product quality produces…
Lenny’s Podcast117 min
Sander Schulhoff · Jun 19, 2025
Key learnings- Prompt engineering remains valuable: Sander argues that bad prompts can drop accuracy near zero on a task while good prompts can…
- Few-shot prompting is the highest-impact basic technique: give the model several examples of what good output looks like, using a…
- Ask the model to decompose a problem by first listing the subproblems it needs to solve, then solving each one before answering…
Lenny’s Newsletter♥ 278
Jun 17, 2025 · 14 min
Subscriber post — summary onlyLenny Rachitsky follows up his tech worker sentiment survey by investigating how people who avoid or effectively manage burnout do it. Drawing on open-ended video surveys and interviews, he introduces ARMOR, a five-part…
Lenny’s Podcast155 min
Hilary Gridley · Jun 15, 2025
Key learnings- When you feel criticized, skip litigating what others think and instead take one small action that demonstrates the opposite of…
- Use behavioral activation: act first on a small, concrete step, since action tends to lift mood and break negative spirals rather…
- Speak up in meetings with valuable input; fear of saying the wrong thing is the main blocker, and building the skill to take a…
Lenny’s Podcast148 min
Bob Baxley · Jun 12, 2025
Key learnings- Before joining a new company, check whether founders genuinely believe in design; design-led cultures are born that way, not…
- When changing cultures, keep your core values but re-express them in the new company's behaviors rather than carrying over old…
- Keep teams small when inventing something new; add people once the vision is clear, since more people slows creative convergence.
Lenny’s Newsletter♥ 294
Jun 10, 2025 · 20 min
Subscriber post — summary onlyColin Matthews explains how product teams can move beyond individual AI prototyping by building shared component libraries, using baselines and forks, and matching prototype fidelity to each stage of the product…
Lenny’s Podcast93 min
Mike Krieger · Jun 5, 2025
Key learnings- Use AI as an independent strategy critic: ask it to be brutal or to challenge your thinking, since default prompts tend to…
- As AI writes most code, bottlenecks shift upstream to deciding what to build and aligning people, and downstream to merge queues…
- Give teams a minimum viable strategy so people feel empowered to build and explore at the edge of model capabilities without…
Lenny’s Newsletter♥ 345
May 27, 2025 · 17 min
Subscriber post — summary onlyLenny Rachitsky and Noam Segal report results from a survey of over 8,200 tech workers on burnout, optimism, manager effectiveness, work setup, company size, career clarity and AI anxiety. The core argument is that…
Lenny’s Podcast95 min
Krithika Shankarraman · May 25, 2025
Key learnings- Don't copy competitors' playbooks blindly; first diagnose the real funnel problem, since a leaky bottom-of-funnel means…
- Use a four-step DATE approach: diagnose the problem, analyze competitors for gaps, take a deliberately different path, then…
- Judge marketing by pipeline, revenue, signups, and activation rather than vanity metrics like clicks, views, and impressions.
Lenny’s Podcast118 min
Mayur Kamat · May 22, 2025
Key learnings- Join fast-growing companies, since learning compounds much faster when you ship and learn daily rather than over multi-year…
- Identify your genuine strengths, through structured assessments or peer feedback, and seek roles where success depends on using…
- Early in your career, don't optimize for compensation; most earnings tend to come later, so prioritize learning and fit.
Lenny’s Newsletter · Free post♥ 195
May 20, 2025 · 14 min
Saumil Mehta, former CPO of Square, argues that the "skip lead" (the manager of managers) is pivotal to organizational health, since most manager problems trace back to how the skip leads hires, reviews, and coaches…
Lenny’s Podcast71 min
Aparna Chennapragada · May 18, 2025
Key learnings- Prototype and build to see what you want before committing; prompt sets and prototypes can replace traditional PRDs as the…
- Time to first demo is shrinking while time to full deployment grows, so raise the bar for what earns scale and avoid chasing…
- Treat conversational interfaces as designed products: prompts, editable plans, progress display, and follow-up suggestions are…
Lenny’s Podcast72 min
Dmitry Zlokazov · May 15, 2025
Key learnings- Treat product managers as end-to-end owners of their area, closer to local CEOs, with authority over the roadmap, team direction…
- Hire for raw intellect and an unquenched hunger to build things, rather than for years of experience, since experienced hires…
- Look for people who have founded startups or worked as tech co-founders, since they tend to be hands-on across many areas and…
Lenny’s Newsletter♥ 365
May 13, 2025 · 6 min
Subscriber post — summary onlyLenny Rachitsky revisits the product job market using TrueUp job-board data, finding a mostly optimistic picture for 2025. Open PM and engineering roles are rising, AI-related roles are growing rapidly, layoffs are…
Lenny’s Podcast134 min
Nabeel S. Qureshi · May 11, 2025
Key learnings- Define who your company is not for: Palantir screened for independent-minded, intellectually broad, intensely competitive people…
- Avoid meaningless principles like 'move fast'; write principles people can meaningfully disagree with, and pressure-test project…
- Use forward deployed engineers who are real builders empowered to create new product for a customer, working in person with the…
Lenny’s Podcast78 min
Jerry Colonna · May 8, 2025
Key learnings- Ask how you have been complicit, not responsible, in creating the conditions you say you don't want; this evokes personal agency…
- Use radical self-inquiry to examine what you claim to want versus what you actually feel, such as saying you dislike busyness…
- Notice whether your drive comes from proving your worth; separate the enjoyment of the work from the need to feel like somebody.
Lenny’s Newsletter♥ 240
May 6, 2025 · 28 min
Subscriber post — summary onlyA guest-authored paid guide from a full-time executive negotiation coach who presents GAINS, a five-step framework (Gather, Align, Influence, Navigate, Secure) for negotiating senior compensation. The core argument is…
Lenny’s Podcast89 min
Michael Truell · May 1, 2025
Key learnings- Build the product you and your team actually use every day (dogfooding) so you never ship anything that isn't genuinely useful…
- When working with AI coding tools, chop tasks into small specify-generate-review loops rather than handing over one giant…
- Spend time on side projects deliberately pushing AI to its limits to build a calibrated gut feeling for what current models can…
Lenny’s Newsletter♥ 325
Apr 29, 2025 · 25 min
Subscriber post — summary onlyTal Raviv, guest-writing for Lenny's Newsletter, offers a hands-on guide to using AI agents to offload repetitive product management work. He walks through setting up a simple customer-prep agent, a checklist for…
Lenny’s Podcast106 min
Daniel Lereya · Apr 27, 2025
Key learnings- Treat a competitor's rapid shipping as a gift that proves a goal is possible, then set an ambitious target that forces you to…
- Measure product managers by the impact they validate for customers, not by features shipped; define the problem, the opportunity…
- Ask each quarter what your product will do differently for customers a quarter from now, and check whether you can name your…
Lenny’s Podcast107 min
Varun Mohan · Apr 20, 2025
Key learnings- Expect your first big bet to be wrong; stay irrationally optimistic about the vision while ruthlessly testing and discarding the…
- Be willing to pivot fully and quickly when hypotheses break, as Varun's team did when model architectures converged on…
- Build the interface where AI-generated code gets reviewed, not just where it gets typed; Windsurf's tripled acceptance rate after…
Lenny’s Podcast98 min
Guillermo Rauch · Apr 13, 2025
Key learnings- Treat taste as a skill you can build by increasing exposure hours: deliberately spend time watching people use your product and…
- Learn how systems work under the hood, since knowing the right technical tokens helps you steer AI models toward your intent more…
- Put product feedback loops inside the product itself, as Rauch suggests borrowing from Stripe's in-product feedback button…
Lenny’s Podcast116 min
Kevin Weil · Apr 10, 2025
Key learnings- Build products at the edge of current model capabilities, since models improve every few months and a barely-working product can…
- Treat evals as unit tests for models: define hero use cases, write evals for them, and hill-climb on those evals to know whether…
- Expect AI behavior to be fuzzy: a model right 60%, 95%, or 99.5% of the time implies very different product designs, so study…
Lenny’s Newsletter♥ 579
Apr 8, 2025 · 15 min
Subscriber post — summary onlyAman Khan argues that writing evaluations is becoming a defining skill for AI product managers, since evals measure how each part of a system affects quality. The post explains what evals are, compares human, code-based…
Lenny’s Podcast71 min
Wes Kao · Apr 6, 2025
Key learnings- Spend less time on why an idea matters and more on the specific how: concrete steps, nuances, and examples that let people apply…
- Cut backstory and preamble; start right before the juicy part of the story, as Wes puts it, 'right before you get eaten by the…
- Recognize that formats like Twitter or keynotes allow more BS, while courses and cohort settings demand rigor because students…
Lenny’s Newsletter · Free post♥ 481
Apr 1, 2025 · 40 min
“Annual subscribers now get a free year of Perplexity Pro, Notion, Superhuman, Linear, and Granola. Subscribe now. A lot of you are having a hard time finding a job. I hear stories from readers who send out hundreds of resumes and get zero responses, go through month-long interview loops that often end in getting ghosted, and continue on without ever hearing honest feedback about what they could do differently. I want to help. In the…”
Lenny’s Podcast133 min
Ryan Singer · Mar 30, 2025
Key learnings- Start from a fixed time budget (appetite) and shape a solution that fits it, rather than estimating a large idea and hoping it…
- Hold shaping sessions where product, design, and a senior engineer work together to sketch the idea and surface technical…
- Aim for a shaped idea describable in under about ten moving pieces; if it takes more, it likely isn't shaped well enough.
Lenny’s Podcast110 min
Gaurav Misra · Mar 27, 2025
Key learnings- Aim for every engineer to ship a marketable product each week, sliced down to an MVP so the team can gather real user feedback…
- When time is tight, cut scope rather than quality: repeatedly remove elements from a feature until removing anything more would…
- Treat technical debt as financial leverage for startups, but track it like interest: once debt consumes most engineering time…