"Using coding agents well is taking every inch of my 25 years of experience as a software engineer." Simon Willison (@simonw) is one of the most prolific independent software engineers and most trusted voices on how AI is changing the craft of building software. He co-created Django, coined the term "prompt injection," and popularized the terms "agentic engineering" and "AI slop." In our in-depth conversation, we discuss: 🔸 Why November 2025 was an inflection point 🔸 The "dark factory" pattern 🔸 Why mid-career engineers (not juniors) are the most at risk right now 🔸 Three agentic engineering patterns he uses daily: red/green TDD, thin templates, hoarding 🔸 Why he writes 95% of his code from his phone while walking the dog 🔸 Why he thinks we're headed for an AI Challenger disaster 🔸 How a pelican riding a bicycle became the unofficial benchmark for AI model quality Listen now 👇 t.co/wlEIyOehU8

How Anthropic’s product team moves faster than anyone else I sat down with @_catwu, Head of Product for Claude Code at @AnthropicAI, to get a peek into their unprecedented shipping pace, how AI is changing the PM role, and how to be the right amount of AGI-pilled. We discuss: 🔸 How Anthropic’s shipping cadence went from months to weeks to days 🔸 The emerging skills PMs need to develop right now 🔸 Why you should build products that don't work yet—then wait for the model to catch up 🔸 Why a 95% automation isn't really an automation 🔸 Cat’s most underrated AI skill (introspection) 🔸 What Cat actually looks for when hiring PMs now (hint: it's not traditional PM skills) Listen now 👇 t.co/uymmT55Nq6

Automation is a lie. CLIs are over. The SaaSpocalypse is dumb. A year ago @danshipper came on the podcast to predict where AI was heading. He was remarkably right—including the call that everyone was sleeping on Claude Code. Dan has a unique lens into where things are going because his team at @every is possibly the most AI-pilled group of people in tech. I always learn a ton talking to Dan. So I brought him back for round two. We'll score these in exactly a year: 🔸 Every company will have one “super-agent” in Slack. 🔸 Codex and Claude Code will become the new operating system for knowledge work. 🔸 The AI job apocalypse is not happening. 🔸 PMs and designers will thrive. 🔸 We will read way more AI-generated writing and we will like it. 🔸 "I would buy SaaS stocks right now." Listen now 👇 t.co/wzxQ5bz49h

Design lead for Claude: The classic design process is dead. Here's what's replacing it. Jenny Wen (@jennywen) leads design for Claude at @AnthropicAI, was previously director of design at @Figma, and a designer at @Dropbox, @Square, and @Shopify. In our in-depth conversation, we discuss: 🔸 Why the classic discovery → mock → iterate design process is becoming obsolete 🔸 What a day in the life of a designer at Anthropic looks like, including her AI tool stack 🔸 Whether AI will eventually surpass humans in taste and judgment 🔸 Why Jenny left a director role at Figma to return to IC work 🔸 The three archetypes Jenny is hiring for now This conversation changed how I think about the future of design. Listen now 👇 t.co/r4HICq4Ytn

Software is not a moat Over the last 15+ years, nearly every innovation @EvanSpiegel and his team shipped got copied. Stories. AR glasses. Swipe-based navigation. The camera-first interface. And yet @Snapchat is the only independent consumer social app that has lasted. Nearly 1 billion MAUs. ~$6B in annual revenue. Over 8 billion AI photos shared on Snapchat *every day*. In our in-depth conversation, we discuss: 🔸 Why distribution—not product—is now the biggest challenge for startups 🔸 How Snap keeps inventing with a 9-to-12-person design team 🔸 How AI is changing the way designers work 🔸 Why humanity's comfort with AI will be a bigger bottleneck than the technology 🔸 Why Evan is calling this year a "crucible moment" for Snap Listen now 👇 t.co/2KO5eH2GHC

What's a product under $250 that has genuinely improved your life?

Amol (Head of Growth at @AnthropicAI) just joined Twitter. Follow for free alpha. BTW, can you believe they hit $30B ARR before they even released Mythos?

Claude Code launched just one year ago. Today it writes 4% of all GitHub commits, and DAU 2x'd last month alone. In my conversation with @bcherny, creator and head of Claude Code, we dig into: 🔸 Why he considers coding "largely solved" 🔸 What tech jobs will be transformed next 🔸 The counterintuitive bet that made Claude Code take off 🔸 Why he left for Cursor and what brought him back 🔸 Practical tips for getting the most out of Claude Code and Cowork 🔸 Much more Listen now👇 t.co/4hHAEq0Nto

Anthropic is on an unprecedented growth run. Just in the past year they grew from $1B to $19B ARR. They added $6B in ARR just in *February*. Companies like Palantir and Atlassian took 15-20 years to reach ~$5B ARR. Anthropic is adding that every month. Amol Avasare is head of growth at Anthropic, and one of the most impressive people I've had on the podcast. In his first ever public interview, Amol shares: 🔸 How Anthropic is automating growth experiments with Claude (their internal tool called “CASH”) 🔸 Why activation is the single highest-leverage growth problem in AI 🔸 Why Amol is hiring more PMs, not less 🔸 How he uses Cowork to automatically detect team misalignment in Slack 🔸 How the company’s focus on AI coding created a research flywheel that accelerated their models 🔸 How Amol landed his role by cold emailing Anthropic’s CPO @mikeyk 🔸 The brain injury that nearly ended Amol's career Listen now 👇 t.co/YEn8K2xjCQ

The full enterprise sales cycle, step by step with @jjen_abel Most people think there are 5 sales stages. There are actually 15. Skip a step and 💀 We discuss: 🔸 The “pincer model” for landing the first meeting 🔸 How to craft a winning 2-3 sentence cold outreach pitch 🔸 How to run an intro call that extracts maximum intelligence 🔸 The correct 2-3 day pilot structure 🔸 Pro tips for navigating pricing and procurement 🔸 So much more 84 minutes of enterprise sales alpha. Listen now 👇 youtube.com/watch

"I design teams like terrorist organizations." 90 minutes of unfiltered product advice from @petersellis We discuss: 🔸 What it's really like to manage @nikitabier 🔸 Why growth almost always comes from the core 🔸 Why great taste is knowing when to stop 🔸 Why the median PM is so bad 🔸 Designing teams like terrorist organizations Listen now 👇 youtube.com/watch

My biggest takeaways from Claude Code's Head of Product @_catwu: 1. Anthropic’s product development timelines have gone from six months to one month, sometimes one week, sometimes one day. Part of this acceleration is access to the latest models (i.e. Mythos). Another is shipping new products into “research preview,” making clear it's early, experimental, and might not be supported forever. Another is an evergreen "launch room "where engineers post ready features and marketing turns around announcements the next day. 2. The PM role is shifting from coordinating multi-month roadmaps to enabling teams to ship daily. As Cat puts it, “There should be less emphasis on making sure you are aligning your multi-quarter roadmaps with your partner teams and more emphasis on, OK, how can we figure out the fastest way to get something out the door?” 3. The most efficient shipping unit is an engineer with great product taste. On Cat’s team, many engineers go end-to-end—from seeing user feedback on Twitter to shipping a product by the end of the week—without a PM involved. Also, almost all the PMs on the Claude Code team have either been engineers or ship code themselves, and the designers have been front-end engineers. The roles are merging, and the most valuable skill is product taste, not job title. 4. Build products that are on the edge of working. Claude Code’s code review product failed multiple times because earlier models weren’t accurate enough. But because the prototype was already built, they could swap in Opus 4.5 and 4.6 and immediately test whether the gap was closed. Teams that wait for the model to be ready will always be a cycle behind. 5. The most underrated skill for building AI products is asking the model to introspect on its own mistakes. Cat regularly asks the model why it made an unexpected decision. The model will explain that something in the system prompt was confusing, or that it delegated verification to a subagent that didn’t check its work. This reveals what misled the model so the team can fix the harness. 6. Every model release forces their team to revisit existing products and audit their system prompt to remove features the model no longer needs. Claude Code’s to-do list was a crutch for earlier models that couldn’t track their own work. With Opus 4, the model handles it natively. Features built as scaffolding for weaker models become debt when the model catches up—so the team actively strips them. 7. Anthropic employees build custom internal tools instead of buying SaaS products. A sales team member built a web app that pulls from Salesforce, Gong, and call notes to auto-customize pitch decks—work that used to take 20 to 30 minutes now takes seconds. Their core stack is Claude Code, Cowork, and Slack. No Notion, no Linear, no Figma. 8. People underestimate how much Claude’s personality contributes to its success. As Cat describes it, “When you reflect on everyone you’ve worked with, there’s just some people where you’re like, I really like their energy, their vibe.” Claude is designed to be low-ego, positive, competent, and earnest—qualities that make it feel like a great coworker, not just a tool. This isn’t cosmetic; it’s what makes people want to use Claude for hours every day. The team has a dedicated person, Amanda, who “molds Claude’s character,” and it’s one of the hardest roles at the company because success is so subjective. 9. The future of work is managing fleets of AI agents, not doing the work yourself. Cat sees a clear progression: first, individual tasks become successful. Then people start running multiple tasks at the same time (multi-Clauding). Next, people will run 50 or 100 tasks simultaneously, which will require new infrastructure—remote execution, better interfaces for managing tasks, agents that fully verify their work, and self-improving systems that incorporate feedback. The human role shifts from doing the work to knowing which tasks to look into, verifying outputs, and giving feedback that makes the system better over time. 10. Hire people who lean into chaos and face every challenge with a smile. At Anthropic, there are weeks when a P0 on Sunday becomes a P00 by Monday and a P000 by Monday afternoon. If you get too stressed about any one thing, you’ll burn out. Their team looks for people who can look at a hard challenge and say, “Wow, that’s gonna be hard. But I’m excited to tackle it and I’m gonna do the best that I possibly can.” This mindset—optimism, resilience, and comfort with constant change—is increasingly essential as the pace of AI development accelerates. Don't miss the full conversation: t.co/1wOUHcdYQN

"High performance machines don't have psychological safety. They're about winning." Keith Rabois (@rabois) was COO of Square, part of the PayPal Mafia, an early investor in Stripe, Palantir, Airbnb, DoorDash, and Ramp, and a 2x founder. He's spent 25 years obsessing over how to build world-class teams. In our in-depth conversation, we discuss: 🔸 How to identify undiscovered talent 🔸 Keith's barrels vs. ammunition hiring framework 🔸 The three traits of the best-performing companies right now 🔸 Why talking to customers is actively harmful for consumer products 🔸 Why the PM role is dying 🔸 The specific interview question he asks every senior candidate 🔸 Why CMOs (not engineers) are becoming the #1 consumer of AI tokens Watch now 👇 t.co/7E1uyvJvQv