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The Looking Glass podcastApr 14, 2026

How to Spot a World-Class Designer

Apr 14, 2026
Key learnings
  • World-class designers are distinguished by judgment and taste, not just the ability to execute polished visuals.
  • Excellent designers obsess over the underlying problem before jumping to solutions, which separates them from those who iterate…
  • Strong designers can articulate why a decision is right, tying craft choices back to user needs and business constraints.
Lenny’s Newsletter♥ 458

Not all AI agents are created equal

Apr 14, 2026 · 15 min
Subscriber post — summary only

The post argues that 'AI agent' covers very different systems, so teams should first categorize each idea by architecture before prioritizing. It proposes three categories (deterministic automation, reasoning and acting…

Lenny’s Podcast105 min

Hard truths about building in the AI era

Keith Rabois · Apr 12, 2026
Key learnings
  • Build the team first: Rabois argues the team you assemble determines the company you build, so hiring quality outranks market…
  • Check hires 30 days after they join by asking whether you would make the same decision again; he says this short loop predicts…
  • Run ruthless referencing with many references per senior hire, and frame questions around whether the person can be a world-class…
SVPG · Marty CaganApr 9, 2026

Commercial vs Internal Products

Apr 9, 2026 · 4 min

Marty Cagan argues that internal products, while worth treating as real products, carry a lower bar on value, usability, feasibility and viability than commercial products. Internal users cannot switch to competitors…

Product Talk · Teresa TorresApr 6, 2026

Ch. 5: Continuous Customer Interviews

Apr 6, 2026 · 8 min

This book club reading guide introduces Chapter 5 of Continuous Discovery Habits, focused on continuous customer interviewing. Teresa Torres argues that product trios should interview customers on a weekly cadence…

Lenny’s Podcast148 min

Anthropic’s $1B to $19B growth run: how Claude became the fastest-growing AI product in history

Amol Avasare · Apr 5, 2026
Key learnings
  • Expect most growth time to go to 'success disasters' once growth is rapid; firefighting breaking systems matters as much as new…
  • In AI-first products, skew the growth portfolio toward larger swings, since future product value could be orders of magnitude…
  • Treat activation as a top lever in AI products: identify user traits that predict which feature fits them, then guide them there.
Lenny’s Podcast142 min

An AI state of the union: We’ve passed the inflection point, dark factories are coming, and automation timelines

Simon Willison · Apr 2, 2026
Key learnings
  • Coding agents crossed a reliability threshold around November 2025, so they now usually do what you ask, which changed how…
  • Writing code is now cheap, so the bottlenecks move to ideation, prototyping, testing, and process; build several quick prototypes…
  • Use test-driven development with agents: have them write tests, run them, and watch them fail first (Red/Green TDD) to keep…
Lenny’s Podcast134 min

From skeptic to true believer: How OpenClaw changed my life

Claire Vo · Mar 29, 2026
Key learnings
  • Run several purpose-built agents instead of one general agent; splitting tasks keeps each agent's context focused and reduces…
  • Install OpenClaw on a separate clean machine such as an old laptop or Mac Mini, with its own local admin account, rather than…
  • Onboard the agent like a new employee: give it its own email and calendar, share access selectively, and expand trust…
Lenny’s Podcast116 min

The art of influence: The single most important skill that AI can’t replace

Jessica Fain · Mar 22, 2026
Key learnings
  • Treat stakeholder conversations as discovery interviews: go in to learn and strengthen your plan, not simply to get approval for…
  • Remember executives have chaotic calendars and little context on your topic, so spend under 60 seconds at the start restating why…
  • Ground your pitch in the executive's success metrics and board pressures, and show explicitly how your proposal moves those…
Lenny’s Newsletter♥ 328

How I built LennyRPG

Mar 17, 2026 · 23 min
Subscriber post — summary only

Designer Ben Shih describes building LennyRPG, a Pokémon-style pixel game where players meet and quiz Lenny's Podcast guests using transcripts from 300+ episodes. The post walks through his AI-assisted workflow…

The Looking Glass podcastMar 11, 2026

What Excellent Growth Teams See That Others Miss

Mar 11, 2026
Key learnings
  • Excellent growth teams look for opportunities that others in the organization tend to overlook, rather than only chasing the…
  • Growth work at a marketplace like DoorDash requires balancing consumers, merchants, and dashers, so teams should consider the…
  • Seven lessons framing suggests growth is treated as a repeatable discipline with distinct principles rather than a series of…
Lenny’s Newsletter♥ 420

A guide to advanced B2B positioning

Mar 10, 2026 · 15 min
Subscriber post — summary only

Lenny's paid guest post by April Dunford, a positioning expert who has worked with 300+ B2B companies, covers four advanced roadblocks that derail positioning work. It argues that disagreement over competitors, product…