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Lenny’s Podcast93 min

OpenAI Codex lead on the new shape of product work

Andrew Ambrosino · Jun 28, 2026
Key learnings
  • Implementation is no longer the expensive part of building; the scarce skill is taste, meaning deciding what to build and…
  • Pick the medium deliberately: use a document to clarify a vague product area, and a prototype to stress-test an interaction…
  • Prototypes can look production-ready and anchor teams too early, so label whether something is an exploration or a shipping…
Lenny’s Podcast129 min

Building the most AI-pilled engineering team in the world

Fiona Fung · Jun 21, 2026
Key learnings
  • Manage with AI by running recurring Claude sessions over repos, Slack, and metrics to summarize shipped work and turn it into…
  • Automate daily leadership rituals such as scanning feedback channels with scheduled routines that surface themes and draft PRs…
  • Give Claude explicit frameworks such as checked-in specs and skills describing what good looks like, so automated code review can…
The Beautiful Mess · John Cutler♥ 48

TBM 426: The Trouble With Mirrors

Jun 16, 2026

John Cutler examines the difference between using mirrors and practicing mirroring, two ways of reflecting back what teams and people do. He describes how his own thinking about this distinction has evolved over the…

Lenny’s Podcast107 min

The hidden pattern behind successful products

Mark Pincus · Jun 14, 2026
Key learnings
  • Use Proven, Better, New: master what already works first, make it measurably better in ways 10 out of 10 existing users would…
  • Assume your instincts are right but your specific ideas are often wrong; test many ideas in your innovation zone and fail for the…
  • Start humbly and small; ambitious visions before product-market fit tend to cause failure, and early wins usually come from…
The Looking Glass · Julie Zhuo♥ 195

To All the Folks Who Are About to Be Rich

Jun 13, 2026
Subscriber post — summary only

Julie Zhuo writes to people about to become wealthy through an IPO, acquisition, or successful business, framing a sudden liquidity event as a turning point. The essay appears to address how to handle that new reality…

The Looking Glass podcastJun 9, 2026

The Art and Excellence of Sales

Jun 9, 2026
Key learnings
  • Treat sales as a craft worth mastering, not a lesser discipline; understanding how customers buy makes product leaders far more…
  • Learn to listen closely to what customers are actually trying to accomplish before proposing solutions or pitching value.
  • Build trust through consistent follow-through, since credibility compounds over repeated interactions with buyers and internal…
The Beautiful Mess · John Cutler♥ 83

TBM 425: AI and Agency

Jun 7, 2026

The piece argues that organizations asking their teams to find ways to use AI for company benefit are undermining that goal by stripping away the agency people need to experiment and decide. The core claim is that…

Lenny’s Podcast121 min

Father of the iPod and iPhone on building taste, judgment, and creativity in the AI era

Tony Fadell · Jun 7, 2026
Key learnings
  • Start product ideas from a real, persistent customer pain, then ask whether a new technology can solve it in a way that…
  • For a true 1.0 in a new category, rely on a small group of named opinion-based decision makers, since data from analogs is…
  • Micromanage the few decisions that truly matter to the customer, cost, or long-term vision, and delegate the rest, instead of…
Lenny’s Podcast109 min

A rational conversation on where AI is actually going

Benedict Evans · May 31, 2026
Key learnings
  • Treat AI as roughly as big as the internet or mobile, and recognize we are early, like 1997, with most applications not yet built…
  • Expect adoption to be very uneven; survey data shows many people are not using AI at all, so don't assume the people in your…
  • Ask whether a job is a task that can be automated or a deeper outcome; consultants and professionals are hired for judgment…
Lenny’s Podcast118 min

The AI paradox: More automation, more humans, more work

Dan Shipper · May 24, 2026
Key learnings
  • Keep using the newest models and agent tools for your real work, and experiment on your own time if your employer restricts…
  • Expect most company AI to start as one shared agent that everyone can talk to, likely in Slack, rather than many personal agents…
  • Design products so agents can be users too: make them easy to drive via CLI and browser-friendly, because the customer's own AI…
Substack · Shreyas Doshi♥ 83

On Blunt Feedback

May 19, 2026

Shreyas Doshi argues that blunt feedback can be transformative, but its value depends heavily on the giver's intent and judgment. Feedback delivered bluntly without care or accuracy can cause harm rather than growth…