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Want to steal a customer from your competitor? 99% of sales reps, 95% of CROs, and 99% of CEOs never ask the one question that would get it done. And its so, so simple: What would it take for you to move over to us? What

Watch now (24 mins) | Meta launched Muse Wonder with claims of frontier agentic performance, so I ran it headlessly through Claude Code against nearly 20 tasks to find out if any of it is true

Most B2B + AI companies are locking their 2027 event budgets between now and January. Most will spread that budget across too many events, picked from lists built on organizer press releases. By Q3, half of those booths

Every time I see a CRO that doesnt sell themselves, they fail. Every time I see a CTO that doesnt code themselves, they fail. Every time I see a CMO that doesnt market themselves, they fail. Every time I see a CCO that i

A framework for assessing whether the company youre considering joining is built to last

Venture is on fire right now. AI rounds are closing at speeds and sizes we havent seen before, and the VC asset class has held up better than most people expected a year ago. Private equity is in a very different spot. P

We just shipped the biggest update yet to our AI Agent Playbook for GTM. It is the October 2026 edition: 53 pages, 27 parts, every number, every mistake, and every framework from running SaaStr on 3 humans and 21+ AI age

Your weekly listens from How I AI, part of the Lenny's Podcast Network

I asked our agent for SaaStr AI Connect a simple question this week: if we wanted to move hosting, where should we go? It came back with a full evaluation and one line at the top: For hosting the app, Id pick Render. In

Listen now | Alex Cornell explains how Muse serves your mom and an engineer with the same interface, and demos a SkyMall-style catalog, golf recaps, and a blog turned podcast

My cut of the episode where Dev Ittycheria, one week back as CEO of MongoDB, told me I was wrong about the biggest story of the week. Thursdays recap covered all four of us. This is my side of it: ten decisions Id make s

Listen now (62 mins) | Josh Woodward of Google Labs on where great ideas come from, knowing when to kill them, and building for a world where whats possible changes every week

Sherif Mansour has been at Atlassian for 17 years. He runs AI across the product portfolio and owns the product management craft, which means 450 PMs. Atlassian has more than 20 apps. Six were built in the gen AI era and

Community Wisdom 301

Remote is a seven-year-old global payroll and employment platform based in Amsterdam. It leaned in early to making payroll (and more) for distributed and global teams work, and is one of the most trusted vendors in the s

An IPO should be Plan A. Its the best outcome for almost everyone on the cap table. But founders, employees and even a lot of VCs treat the IPO date as the liquidity date. For most of the cap table most of the money come

With Harry Stebbings, Jason Lemkin, Rory ODriscoll, and special guest Dev Ittycheria, back in the CEO seat at MongoDB Dev Ittycheria joined us one week into his second run as CEO of MongoDB. CJ Desai stepped down on Sept

Cloudflare latest quarter reported of $696.1 million, up 36%, which annualizes to $2.8 billion. Three months earlier, it had cut more than 1,100 roles, about 20% of the company, and the stock dropped 23%. In Q2 growth ac

Your weekly listens from How I AI, part of the Lennys Podcast Network

Watch now (36 mins) | Kath Korevec demos ChatGPT Sites live at OpenAI DevDay, showing how to turn Slack, Notion, and calendar data into internal tools that adapt to each person on your team

Listen now (37 mins) | Tibo Sottiaux on why Dots is OpenAIs biggest bet, why agents will dominate internet traffic, and what builders are still getting wrong

Community Wisdom 301

When a new CRO / VP Sales shows up to the first board meeting and doesnt know: The top accounts cold The top deals in flight cold Their team and leaders cold The top deals at risk cold Theres like 0% chance it will work

Watch now (24 mins) | Claire tests OpenAIs DevDay releases, from Dots, Spaces, and Sites to AI-picked thumbnails and a $97 game, and shares whats worth trying first

Watch now (46 mins) | Educator and developer John Lindquist shares eight Jev demos, from live voice classification and deduplication to agent routing, showing how low costs make once-impractical ideas worth trying

Plus, some reflections and takeaways from the day

Your weekly listens from How I AI, part of the Lenny's Podcast Network

Watch now (26 mins) | Jev returns type-safe structured values instead of text, which makes it the fastest, cheapest classification layer Ive ever put in a pipelineand this week I shipped three real projects with it

Listen now (94 mins) | Molly Graham revisits her famous career advice for the AI era, and explains why delegating to a robot is nothing like delegating to a human

Community Wisdom 300

Watch now (39 mins) | I ran blind evaluations across writing, frontend prototypes, long-running agentic tasks, SVGs, coding, and video editing, then put Opus 5.5 through Barbie Bench

Watch now (25 mins) | I abandoned Claude for months because it drove me insane. Opus 5.5 changed that, and I'll show you exactly where it's earning a spot back in my stack for frontend, SVGs, and agentic tasks

Why you should never skip error discovery

Your weekly listens from How I AI, part of the Lennys Podcast Network

Watch now (47 mins) | Warp CEO Zach Lloyd shows how his team turns requests from Slack, Linear, and GitHub into tracked, tested pull requests, then measures and improves its cloud-based AI software factory over time

Listen now (97 mins) | Peter Sellis on designing teams like terrorist organizations, riding your best people hard, and the three oxymorons of a truly great PM

Community Wisdom 299

Watch now (38 mins) | I gave Metas Muse my calendar, my email, and my kids chaotic schedule, and it produced a one-shot family PDF more beautiful than anything Ive ever made with Claude or Codex