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Lenny’s Podcast78 min

How have I been complicit in creating the conditions I say I don’t want?

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

The ultimate guide to negotiating your comp

May 6, 2025 · 28 min
Subscriber post — summary only

A 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…

SVPG · Marty CaganMay 5, 2025

INSPIRED in the Generative AI Era

May 5, 2025 · 5 min

Marty Cagan introduces a re-recorded audio edition of INSPIRED and reflects on how the book has held up since its 2007 and 2017 editions. He argues its focus on underlying principles rather than current process is why…

Lenny’s Podcast89 min

The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using

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 Podcast106 min

Inside monday.com’s transformation: radical transparency, impact over output, and their path to $1B ARR

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

Building a magical AI code editor used by over 1 million developers in four months: The untold story of Windsurf

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…
SVPG · Marty CaganApr 17, 2025

Team Autonomy and AI

Apr 17, 2025 · 3 min

Marty Cagan argues that product teams often conflate empowerment and autonomy, and that the two should be considered separately. Empowerment means a team can choose how to solve a problem, while autonomy means it can…

Lenny’s Podcast98 min

Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders

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

OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more

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 Podcast71 min

Become a better communicator: Specific frameworks to improve your clarity, influence, and impact

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 Podcast133 min

A better way to plan, build, and ship products

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

How to win in the AI era: Ship a feature every week, embrace technical debt, ruthlessly cut scope, and create magic your competitors can't copy

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…
HEY World · Jason FriedMar 25, 2025

Go do business

Mar 25, 2025

Jason Fried argues that business cannot be learned from books, posts, or threads, because it is a practical skill built through doing. He compares it to music and sports, where reading about a craft never substitutes…

Lenny’s Newsletter♥ 284

How to ship like a startup

Mar 25, 2025 · 13 min
Subscriber post — summary only

Mihika Kapoor, who helped build FigJam and launched Figma Slides, shares seven lessons for keeping a startup mindset inside a large company. The core argument is that speed, prototypes, open progress-sharing, strong…

SVPG · Marty CaganMar 24, 2025

Product, Design and AI

Mar 24, 2025 · 19 min

Marty Cagan and Bob Baxley argue that in the Generative AI era, strong product managers and product designers become more essential, not less, but only when those roles are defined by their specific, demanding skill…