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Lenny’s Podcast100 min

The non-technical PM’s guide to building with Cursor

Zevi Arnovitz · Jan 18, 2026
Key learnings
  • Start slowly with a ChatGPT project acting as a skeptical 'CTO' before moving to coding tools, gradually easing into code to…
  • Capture ideas quickly as Linear issues using reusable slash commands, so you can pick them up later with context already gathered.
  • Separate the workflow into explore, plan, execute, review, and document phases, and have the AI ask clarifying questions before…
Substack · Shreyas Doshi♥ 49

The Genuine Anti-Sell

Jan 15, 2026

Shreyas Doshi describes a counterintuitive lesson he picked up from observing a manager at Stripe: the most persuasive way to win people over is often to stop selling and instead be genuinely candid about tradeoffs…

Lenny’s Podcast129 min

How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook

Sam Lessin · Jan 15, 2026
Key learnings
  • Aim to enter a room with a low heart rate and an abundance mindset rather than scarcity, since the conversation is a…
  • Arrive a little early, roughly 10 to 15 minutes, and never make a late guest feel bad; a simple apology is enough.
  • When you forget someone's name, introduce your partner first and let the moment hang so the other person picks up the name, or…
HEY World · Jason FriedJan 14, 2026

Great design was a Cuisinart

Jan 14, 2026

Jason Fried argues that the original Cuisinart food processor is a near-perfect example of interface design. Its two large paddle buttons, one latching for continuous ON and one spring-loaded for momentary PULSE/OFF…

Lenny’s Podcast117 min

The power user’s guide to Codex: parallelizing workflows, planning techniques, advanced context engineering tips, automating code reviews, and more

Alexander Embiricos · Jan 12, 2026
Key learnings
  • Ship a product to a small group first, then learn empirically from usage rather than over-planning, especially in fast-moving AI…
  • Onboard users into agentic tools by first working alongside them in the local IDE or terminal, then gradually configure…
  • Give AI coding tools your hardest real tasks rather than trivial ones, and build trust by having the agent first understand the…
Lenny’s Podcast110 min

Aishwarya Naresh Reganti + Kiriti Badam

Aishwarya Naresh Reganti + Kiriti Badam · Jan 11, 2026
Key learnings
  • AI products differ from traditional software mainly because user inputs and model outputs are both non-deterministic, so behavior…
  • Each time you grant an AI system more decision-making autonomy, you give up some human control; autonomy should be earned through…
  • Start with low-agency, high-human-control versions (e.g., suggestions to human agents) and log human corrections to build a…
Medium · Hiten ShahJan 7, 2026

The Drama Triangle Is Organizational Debt

Jan 7, 2026 · 3 min

Hiten Shah argues that many workplace problems are simple to solve once they reach the people directly involved, but they become costly when routed indirectly through intermediaries. Drawing on experiences at…

HEY World · Jason FriedJan 6, 2026

The joy of delegating to competence

Jan 6, 2026

Jason Fried argues that the excitement around AI agents comes less from the technology itself and more from the psychological experience they create: delegating a task to someone fully competent. He notes that most…

Lenny’s Newsletter♥ 255

Best of Lenny’s Newsletter 2025

Jan 6, 2026 · 8 min
Subscriber post — summary only

Lenny Rachitsky's year-end roundup collects the most popular posts from his newsletter, grouped by theme such as AI, career, strategy, growth, and execution, plus a few all-time classics. He also reviews his 2025 goals…

HEY World · Jason FriedJan 5, 2026

The big regression

Jan 5, 2026 · 3 min

Jason Fried describes staying in a brand-new rental house packed with smart-home technology and finds it worse than basic, older equipment. Lights, a TV, a dishwasher that needs an app, a thermostat, and an alarm panel…

Lenny’s Podcast120 min

The high-growth handbook: Molly Graham’s frameworks for leading through chaos, change, and scale

Molly Graham · Jan 4, 2026
Key learnings
  • Keep handing off the work you've mastered so you can take on the next, bigger challenge; the job keeps growing, so you must keep…
  • Name and externalize the emotional reactions to change, then give them about two weeks; anything lasting longer deserves a real…
  • When a team struggles, snorkel before you scuba: check structure (goals, roles, expectations) and team dynamics before blaming…
Substack podcastJan 3, 2026

Time Management: a deep dive

Jan 3, 2026
Key learnings
  • Treat time management as an ongoing experiment rather than a fixed system, testing methods and keeping what actually works for…
  • Advanced time management ideas go beyond to-do lists to focus on how you allocate attention across competing priorities.
  • Protect blocks of deep, uninterrupted work time, since product work is often fragmented by meetings and reactive requests.
Lenny’s Podcast175 min

We replaced our sales team with 20 AI agents—here’s what happened

Jason M Lemkin · Jan 1, 2026
Key learnings
  • Don't abandon a sales motion to chase pure product-led growth if customers need help to buy; many self-serve startups later need…
  • Founders can close the first 10 customers themselves because they excel at the middle of conversations; focus on asking for next…
  • Start hiring sales reps once founders spend about 20% of their time in sales and 20% recruiting; hire at least two reps so you…
Substack · Shreyas Doshi♥ 324

10 ideas for 2026

Dec 30, 2025

Shreyas Doshi argues that clear thinking underpins everything product people do, yet most of us have significant gaps in how we reason. In this year-end essay he offers ten ideas for 2026, framed explicitly as useful to…

Lenny’s Podcast123 min

10 contrarian leadership truths every leader needs to hear

Matt MacInnis · Dec 28, 2025
Key learnings
  • Extraordinary outcomes require extraordinary effort; if people feel comfortable at work, something has gone wrong, and leaders…
  • Deliberately understaff projects, since overstaffing invites politics and pulls people onto low-priority work before it is clear…
  • Withholding feedback is selfish because it optimizes for your own comfort; escalate issues in public and give direct feedback…
Substack podcastDec 27, 2025

Is Writing Really Thinking: a deep-dive

Dec 27, 2025
Key learnings
  • Writing can sharpen thinking by forcing you to make vague ideas explicit and expose gaps in your reasoning.
  • The claim 'writing is thinking' is useful but overextended; not all thinking happens through writing, and writing alone does not…
  • Treat writing as one tool among several for thinking, alongside conversation, sketching, and deliberate reflection.
SVPG · Marty CaganDec 19, 2025

The Product Model at Google

Dec 19, 2025 · 11 min

Marty Cagan and Elias Lieberich describe how the product model shows up at Google, a company with nine products that each exceed one billion monthly users. The article frames the model around three parts: leaders…