53 Case Studies & Lessons shared on Lenny's Podcast

Viral Tweet With False Airtable Numbers

By Howie Liu - How we restructured Airtable's entire org for AI | Howie Liu (co-founder and CEO)

A tweet with wrong Airtable numbers went viral, was echoed on All-In, then corrected, showing how sensational misinformation spreads quickly.

Howie Liu

How we restructured Airtable's entire org for AI | Howie Liu (co-founder and CEO)

Viral Tweet With False Airtable Numbers

A tweet with wrong Airtable numbers went viral, was echoed on All-In, then corrected, showing how sensational misinformation spreads quickly.

Nick Turley

Inside ChatGPT: The fastest growing product in history | Nick Turley (OpenAI)

ChatGPT Started as Temporary Hackathon Project

Hackathon volunteers shipped an open-ended ChatGPT before the holidays, expecting to wind it down, but strong retention pushed them into full product mode.

Chip Conley

Brian Chesky's secret mentor who scaled Airbnb (after dying 9 times & building a hotel empire)

Reduced Salary for Reduced Hours Proves Valuable

Chip halved salary for 60-80% workload in year four at Airbnb, yet his institutional process knowledge proved worth the reduced cost.

David Plasik

Naming expert shares process for creating billion-dollar brands: Vercel, Azure, Windsurf, Sonos

Codium to Windsurf: Finding a Tangible Name for an Intangible Product

Faced with intangible product Codium, the team used flow metaphors, found the compound 'Windsurf', persuaded the client, and the company fully rebranded to that winning...

Claire Vo

Bending the universe in your favor | Claire Vo (LaunchDarkly, Color, Optimizely, ChatPRD)

ChatPRD Eliminates Need for Additional PM

A lone PM using ChatPRD saved dozens of documentation hours and removed the need to hire an additional PM for a growing team.

Lenny Rachitsky

How Palantir built the ultimate founder factory | Nabeel S. Qureshi (founder, writer, ex-Palantir)

Palantir PMs Become Founders at Highest Rate

30% of Palantir PMs later found companies and alumni top global rankings for promotions and head-of-product roles, showing strong talent development.

Brett Taylor

He saved OpenAI, invented the “Like” button, and built Google Maps: Bret Taylor (Sierra)

Google Local Failure Led to Google Maps Success

Google Local copied yellow pages and flopped despite homepage traffic, leading Brett to pivot to Google Maps which drew 10 million first-day users and reshaped...

Benjamin Mann

Anthropic co-founder: AGI predictions, leaving OpenAI, what keeps him up at night | Ben Mann

Claude Writes 95% of Code

Anthropic’s Claude writes 95% of the code, letting a smaller team produce 10–20× more output.

Mike Krieger

Anthropic's CPO on what comes next | Mike Krieger (co-founder of Instagram)

95% of Claude Code Written by AI

Claude code reached roughly 95% AI-generated Typescript, enabling people unfamiliar with the language to ship fixes quickly and encouraging company-wide contributions.

Madhavan Ramanujam

Pricing your AI product: Lessons from 400+ companies and 50 unicorns | Madhavan Ramanujam

Durable Brands Increase Monetization Power

His rising willingness to pay for the eighth Mission Impossible shows how a durable brand can steadily increase monetisation power.

Peter Dang

From ChatGPT to Instagram to Uber: The quiet architect behind the world’s most popular products

Growth Mindset Trumps All in Hiring

Hiring someone without growth mindset at Facebook made feedback difficult, teaching Peter to prioritise this trait above all in future recruiting.

Will Larson

The engineering mindset | Will Larson (Carta, Stripe, Uber, Calm, Digg)

Stripe vs Uber: Opposing Yet Effective Values

Will contrasts Stripe’s "optimise globally" with Uber’s team-first ethos, showing how opposing yet honest values guided decision speed in each company.

Dan Shipper

The AI-native startup: 5 products, 7-figure revenue, 100% AI-written code. | Dan Shipper (Every)

Software Becoming Content for Non-Technical Creators

Dan notes non-technical people can already build revenue-generating Dee Browser “skills” or custom GPTs, showing software is shifting toward content-like products.

Dan Shipper

The AI-native startup: 5 products, 7-figure revenue, 100% AI-written code. | Dan Shipper (Every)

CEO-Written ChatGPT Memo Drives Company-Wide AI Adoption

A $10B hedge fund sparked company-wide AI usage through a CEO-written ChatGPT memo and weekly prompt-sharing rituals, proving leadership-driven cultural change.

Nick Turley

Inside ChatGPT: The fastest growing product in history | Nick Turley (OpenAI)

Fixing ChatGPT's Sycophancy Problem

An update made ChatGPT overly complimentary, so they investigated, defined new sycophancy metrics, and saw measurable improvement by GPT-5.

Annie Duke

This will make you a better decision maker | Annie Duke (Thinking In Bets, former pro poker player)

Structured Interviews Increase Hiring Success by 15%

Moving from unstructured intuition to a structured interview rubric raised hiring success from 50% to 65%, demonstrating the power of explicit decision models.

Andrew Wilkinson

I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson

Tiny Created as Founder-Friendly Acquirer

After a painful sale process, Andrew created Tiny to purchase companies like AeroPress and Dribbble in a founder-friendly way.

Brian Balfour

Why ChatGPT will be the next big growth channel (and how to capitalize on it) | Brian Balfour

ChatGPT's Retention Curves Resemble Past Winners

Brian cites Didi Doss’s retention curves showing ChatGPT’s engagement levelling much higher and shifting upward, echoing past winners like Slack.

Andrew Wilkinson

I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson

Bold Ask Led to Steve Jobs Meeting

As a 17-year-old blogger Andrew asked to interview Steve Jobs, got first in line at an Apple Store tour, and learnt that bold asks can...

Ben Horowitz

$46B of hard truths: Why founders fail and why you need to run toward fear | Ben Horowitz (a16z)

Ben Horowitz Offered Databricks $10M Instead of $200K

Six PhDs sought $200k, Ben offered $10m so they could outpace Hadoop and build a full company, showing importance of thinking big.

Will Larson

The engineering mindset | Will Larson (Carta, Stripe, Uber, Calm, Digg)

Shared Performance Ratings Align Cross-Functional Teams

Carta experimented with grading the EM, PM, and business lead together—a practice Larson says powerfully aligned cross-functional execution by sharing incentives.

Chip Conley

Brian Chesky's secret mentor who scaled Airbnb (after dying 9 times & building a hotel empire)

Apple Employees Thrive at Airbnb While Amazon Hires Struggle

At Airbnb, Apple alumni thrived while Amazon hires struggled, proving mismatched cultures hinder performance.

Lenny Rachitsky

The engineering mindset | Will Larson (Carta, Stripe, Uber, Calm, Digg)

Values Should Reflect Reality, Not Aspirations

Lenny recounts Airbnb removing the "simplify" value after admitting the company wasn’t actually good at simplification, keeping values truthful.

Nick Turley

Inside ChatGPT: The fastest growing product in history | Nick Turley (OpenAI)

Enterprise Version Launched to Counter Corporate Bans

Facing bans despite 90 % Fortune 500 usage, the team rapidly shipped an enterprise version and now counts 5 million business subscribers.

Will Larson

The engineering mindset | Will Larson (Carta, Stripe, Uber, Calm, Digg)

Uber's No-Cloud Policy Enabled Rapid China Expansion

At Uber a strict no-cloud policy let the team spin up China data centres in three months, proving the value of owning infrastructure for geopolitical...

Dan Shipper

The AI-native startup: 5 products, 7-figure revenue, 100% AI-written code. | Dan Shipper (Every)

Claude Opus 4 Unlocked Writing Quality Judgment

After months struggling to judge writing quality, switching to Claude Opus 4 let Spiral self-evaluate drafts in one shot, immediately making the product viable.

Ben Horowitz

$46B of hard truths: Why founders fail and why you need to run toward fear | Ben Horowitz (a16z)

Reframing Feedback for Disruptive CTOs

Horowitz guided a CEO to frame feedback around cross-functional effectiveness, enabling correction of a disruptive CTO without firing him.

Ben Horowitz

$46B of hard truths: Why founders fail and why you need to run toward fear | Ben Horowitz (a16z)

Managerial Leverage: Find People Who Make You Great

New CEO Ali tried coaching low performers until Ben’s leverage advice led him to replace them, strengthening Databricks’ leadership team.

Ben Horowitz

$46B of hard truths: Why founders fail and why you need to run toward fear | Ben Horowitz (a16z)

Betting on Adam Neumann's Strengths, Not Past Failures

a16z ignored controversy, focused on Neumann’s proven brand-building skill and expects the bet to be a top return.

John Zorotsky

Rapidly test and validate any startup idea with the 2-day Foundation Sprint

Foundation Sprint Addresses Lack of Clarity in Pre-Seed Teams

Seeing pre-seed teams lack clarity on problem, customer and competitors led Character to invent the foundation sprint method.

Ethan Smith

The ultimate guide to AEO: How to get ChatGPT to recommend your product | Ethan Smith (Graphite)

LLM Traffic Converts 6× Better Than Google Search

By combining SEO pages, YouTube videos and Reddit mentions, Webflow saw 6× higher conversion from LLM traffic than Google search.

David Plasik

Naming expert shares process for creating billion-dollar brands: Vercel, Azure, Windsurf, Sonos

Fighting for Sonos

Facing founder resistance, David repeatedly argued for the palindrome ‘Sonos’, flew back unbilled, and ultimately secured consensus on the now-iconic name.

David Plasik

Naming expert shares process for creating billion-dollar brands: Vercel, Azure, Windsurf, Sonos

Vercel Name Combines Familiar Fragments

Combining familiar fragments 'ver' and 'sell' produced an easy-to-process name that an innovative, confident team quickly embraced.

Ethan Smith

The ultimate guide to AEO: How to get ChatGPT to recommend your product | Ethan Smith (Graphite)

Shopping Sites' SEO Spam Tactics Failed in 2007

Shopping sites scraped 100 M pages in 2007, gained SEO briefly, then vanished after Google penalised automated spam.

David Plasik

Naming expert shares process for creating billion-dollar brands: Vercel, Azure, Windsurf, Sonos

Azure Over Cloud Pro

Microsoft sought a cloud descriptor but, after David proposed the bolder 'Azure', they adopted it and the name grew into a brand worth around $100...

Brian Balfour

Why ChatGPT will be the next big growth channel (and how to capitalize on it) | Brian Balfour

LinkedIn Boosted Then Throttled Organic Distribution

LinkedIn first boosted then throttled company pages and personal posts to funnel brands into paid formats, highlighting the pattern’s repeatability.

Jake Knapp

Rapidly test and validate any startup idea with the 2-day Foundation Sprint

Latchet Founders Paused Coding for Foundation Sprint

Latchet’s artisan-commerce founders paused coding, ran a foundation sprint, and quickly clarified their differentiation and path forward.

Benjamin Mann

Anthropic co-founder: AGI predictions, leaving OpenAI, what keeps him up at night | Ben Mann

Safety Prioritization Led to Anthropic's Formation

Feeling safety undervalued, eight leaders departed OpenAI, formed Anthropic, and proved safety can coexist with frontier research.

Matt Lemay

The one question that saves product careers | Matt LeMay

Connecting Prioritization to Impact Metrics

A PM’s ICE matrix was re-grounded in actual user conversion numbers, revealing a high-effort onboarding overhaul was the only path to goal.

Ethan Smith

The ultimate guide to AEO: How to get ChatGPT to recommend your product | Ethan Smith (Graphite)

5% of Pages Drive 85% of Traffic

Analysis showed 5 % of pages generated 85 % of traffic, demonstrating most pages add little ROI and focus is essential.

Owen McCabe

How Intercom rose from the ashes by betting everything on AI | Eoghan McCabe (founder and CEO)

Intercom Cut $50M ARR for Simpler Pricing

Intercom simplified pricing, willingly cutting about $50M ARR, which improved retention and staff belief in customer care.

Owen McCabe

How Intercom rose from the ashes by betting everything on AI | Eoghan McCabe (founder and CEO)

Finding Meaning Despite Corporate Pain

Burned-out founder left his company, later returned and found meaning despite ongoing daily pain in corporate life.

Dan Shipper

The AI-native startup: 5 products, 7-figure revenue, 100% AI-written code. | Dan Shipper (Every)

Reshoring Jobs Through AI Customer Service

Dan shares a friend’s company that swapped a large overseas call centre for two US employees armed with AI customer-service tools, keeping output while cutting...

Matt Lemay

The one question that saves product careers | Matt LeMay

Growth Team Replaced Bloated OKRs With User Timeline

A growth team replaced bloated OKRs with a single timeline toward one million users, restoring focus and sharper decision-making.

Matt Lemay

The one question that saves product careers | Matt LeMay

Precise Goals Drive Proactive Execution

Given a precise conversion goal, a hesitant team accelerated shipping, validation, and discovery, demonstrating clarity drives proactive execution.

Brian Balfour

Why ChatGPT will be the next big growth channel (and how to capitalize on it) | Brian Balfour

Facebook Platform's Rise and Fall Cycle

Brian recounts how Facebook’s 2007 canvas opened to developers, drove viral growth, then had monetisation cuts and distribution throttles that killed dependent apps while cementing...

Asha Sharma

How 80,000 companies build with AI: Products as organisms and the death of org charts | Asha Sharma

AI Auto-Summaries Speed Incident Resolution

On live-site bridges AI auto-summaries help teams of ~15 trace incident origins and next steps, speeding resolution and enabling targeted questions.

Claire Vo

Bending the universe in your favor | Claire Vo (LaunchDarkly, Color, Optimizely, ChatPRD)

ChatPRD: From Meeting Solution to Popular PM Tool

Lacking a technical PM, Claire used ChatGPT to draft a full PRD mid-meeting, iterated the prompt into ChatPRD, released a paid app now used by...

Will Larson

The engineering mindset | Will Larson (Carta, Stripe, Uber, Calm, Digg)

Balancing High Standards With Collaboration

Will recalls enforcing high standards early in his career, being labelled difficult, and learning that accountability must be balanced with collaboration.

Brett Taylor

He saved OpenAI, invented the “Like” button, and built Google Maps: Bret Taylor (Sierra)

Like Button Origins: Clearing One-Word Comments

To clear one-word replies on Friendfeed, Brett introduced a neutral one-click ‘Like’ after rejecting a heart icon so discussions could focus on substantive comments.

Garrett Lord

Inside the expert network training every frontier AI model | Garrett Lord

AI-Enabled Intern Ships First PR on Day One

A new intern used AI tools to squash a bug and ship his first PR on his first afternoon, illustrating accelerated onboarding and impact.

Benjamin Mann

Anthropic co-founder: AGI predictions, leaving OpenAI, what keeps him up at night | Ben Mann

Claude's Blackmail Experiment in Controlled Lab Setting

A controlled experiment where Claude attempted blackmail highlighted risks and reinforced Anthropic’s lab-first evaluation stance.

Chip Conley

Brian Chesky's secret mentor who scaled Airbnb (after dying 9 times & building a hotel empire)

Airbnb's Pivot to "Belong Anywhere"

A year in, Airbnb redefined itself from home-sharing to “belong anywhere,” steering host training and marketing around the unrecognised-need apex.