Lenny's Podcast: Product | Career | Growth
Alle afleveringen
366 afleveringen, van nieuw naar oud
-
10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling)
28 december 2025 · 1 uur 36 min
Matt MacInnis is the chief product officer and former longtime COO at Rippling, a unified workforce management platform valued at over $16 billion. Lees meer
We discuss:
1. Why “extraordinary results demand extraordinary efforts”
2. Why you should deliberately understaff projects, and how to know when you’ve gone too far
3. Matt’s transition from COO to CPO and what surprised him about leading product
4. The “high alpha, low beta” framework for evaluating people, processes, and products
5. When founders should quit their startups (hint: much earlier than VCs want you to)
6. How to fight entropy in your organization through relentless energy and intensity
—
Brought to you by:
Google Gemini—Your everyday AI assistant: https://ai.dev/
Datadog—Now home to Eppo, the leading experimentation and feature flagging platform: https://www.datadoghq.com/lenny
GoFundMe Giving Funds—Make year-end giving easy: http://gofundme.com/lenny
—
Transcript: https://www.lennysnewsletter.com/p/10-contrarian-leadership-truths
—
My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/181916584/my-biggest-takeaways-from-this-conversation
—
Where to find Matt MacInnis:
• X: https://x.com/stanine
• LinkedIn: https://www.linkedin.com/in/macinnis
• Email: macinnis@rippling.com
—
Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
In this episode, we cover:
(00:00) Introduction to Matt MacInnis and Rippling
(04:38) The importance of extraordinary efforts
(08:37) The challenges and rewards of relentless effort
(10:11) Your job as a leader is to preserve intensity
(12:39) You learn far more from success than failure
(16:34) Transitioning to chief product officer
(19:54) Fixing product management at Rippling
(25:27) The “high alpha, low beta” framework
(28:55) The PQL framework
(35:16) Hiring frameworks and team dynamics
(36:52) A h…
-
The coming AI security crisis (and what to do about it) | Sander Schulhoff
21 december 2025 · 1 uur 33 min
Sander Schulhoff is an AI researcher specializing in AI security, prompt injection, and red teaming. He wrote the first comprehensive guide on prompt engineering and ran the first-ever prompt injection competition, working with top AI labs and companies. His dataset is now used by Fortune 500 companies to benchmark their AI systems security, he’s spent more time than anyone alive studying how attackers break AI systems, and what he’s found isn’t reassuring: the guardrails companies are buying don’t actually work, and we’ve been lucky we haven’t seen more harm so far, only because AI agents aren’t capable enough yet to do real damage. Lees meer
We discuss:
1. The difference between jailbreaking and prompt injection attacks on AI systems
2. Why AI guardrails don’t work
3. Why we haven’t seen major AI security incidents yet (but soon will)
4. Why AI browser agents are vulnerable to hidden attacks embedded in webpages
5. The practical steps organizations should take instead of buying ineffective security tools
6. Why solving this requires merging classical cybersecurity expertise with AI knowledge
—
Brought to you by:
Datadog—Now home to Eppo, the leading experimentation and feature flagging platform: https://www.datadoghq.com/lenny
Metronome—Monetization infrastructure for modern software companies: https://metronome.com/
GoFundMe Giving Funds—Make year-end giving easy: http://gofundme.com/lenny
—
Transcript: https://www.lennysnewsletter.com/p/the-coming-ai-security-crisis
—
My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/181089452/my-biggest-takeaways-from-this-conversation
—
Where to find Sander Schulhoff:
• X: https://x.com/sanderschulhoff
• LinkedIn: https://www.linkedin.com/in/sander-schulhoff
• Website: https://sanderschulhoff.com
• AI Red Teaming and AI Security Masterclass on Maven: https://bit.ly/44lLSbC
—
Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/len…
-
The new AI growth playbook for 2026: How Lovable hit $200M ARR in one year | Elena Verna (Head of Growth)
18 december 2025 · 1 uur 32 min
Elena Verna is the head of growth at Lovable, the leading AI-powered app builder that hit $200 million in annual recurring revenue in under a year with just 100 employees. In this record fourth appearance on the podcast, Elena shares how the traditional growth playbook has been completely rewritten for AI companies. She explains why Lovable focuses on innovation over optimization, how they’ve shifted from activation to building new features, and why giving away their product for free has become their most powerful growth strategy. Lees meer
We discuss:
1. Why 60% to 70% of traditional growth tactics no longer apply in AI
2. Why you have to re-find product-market fit every 3 months
3. The specific growth tactics driving Lovable’s unprecedented growth
4. Why giving away product is a growth strategy that beats paid ads
5. “Minimum lovable product” as the new standard (not minimum viable product)
6. Why activation now belongs to product teams, not growth teams
7. Whether you should join an AI startup (honest tradeoffs)
—
Brought to you by:
WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs
Vercel—Your collaborative AI assistant to design, iterate, and scale full-stack applications for the web
Persona—A global leader in digital identity verification
—
Transcript: https://www.lennysnewsletter.com/p/the-new-ai-growth-playbook-for-2026-elena-verna
—
My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/181207556/my-biggest-takeaways-from-this-conversation
—
Where to find Elena Verna:
• X: https://x.com/elenaverna
• LinkedIn: https://www.linkedin.com/in/elenaverna
• Newsletter: https://www.elenaverna.com
—
Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
In this episode, we cover:
(00:00) Introduction to Elena Verna
(05:19) The scale and growth of Lovable
(08:55) Confidence in Lovab…
-
Why humans are AI’s biggest bottleneck (and what’s coming in 2026) | Alexander Embiricos (OpenAI Codex Product Lead)
14 december 2025 · 1 uur 25 min
Alexander Embiricos leads product on Codex, OpenAI’s powerful coding agent, which has grown 20x since August and now serves trillions of tokens weekly. Before joining OpenAI, Alexander spent five years building a pair programming product for engineers. He now works at the frontier of AI-led software development, building what he describes as a software engineering teammate—an AI agent designed to participate across the entire development lifecycle. Lees meer
We discuss:
1. Why Codex has grown 20x since launch and what product decisions unlocked this growth
2. How OpenAI built the Sora Android app in just 18 days using Codex
3. Why the real bottleneck to AGI-level productivity isn’t model capability—it’s human typing speed
4. The vision of AI as a proactive teammate, not just a tool you prompt
5. The bottleneck shifting from building to reviewing AI-generated work
6. Why coding will be a core competency for every AI agent—because writing code is how agents use computers best
—
Brought to you by:
WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs: https://workos.com/lenny
Fin—The #1 AI agent for customer service: https://fin.ai/lenny
Jira Product Discovery—Confidence to build the right thing: https://atlassian.com/lenny/?utm_source=lennypodcast&utm_medium=paid-audio&utm_campaign=fy24q1-jpd-imc
—
Transcript: https://www.lennysnewsletter.com/p/why-humans-are-ais-biggest-bottleneck
—
My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/180365355/my-biggest-takeaways-from-this-conversation
—
Where to find Alexander Embiricos:
• X: https://x.com/embirico
• LinkedIn: https://www.linkedin.com/in/embirico
—
Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
In this episode, we cover:
(00:00) Introduction to Alexander Embiricos
(05:13) The speed and ambition at OpenAI
(11:34) Codex: OpenAI’s…
-
The 100-person AI lab that became Anthropic and Google's secret weapon | Edwin Chen (Surge AI)
7 december 2025 · 1 uur 11 min
Edwin Chen is the founder and CEO of Surge AI, the company that teaches AI what’s good vs. what’s bad, powering frontier labs with elite data, environments, and evaluations. Surge surpassed $1 billion in revenue with under 100 employees last year, completely bootstrapped—the fastest company in history to reach this milestone. Before founding Surge, Edwin was a research scientist at Google, Facebook, and Twitter and studied mathematics, computer science, and linguistics at MIT. Lees meer
We discuss:
1. How Surge reached over $1 billion in revenue with fewer than 100 people by obsessing over quality
2. The story behind how Claude Code got so good at coding and writing
3. The problems with AI benchmarks and why they’re pushing AI in the wrong direction
4. How RL environments are the next frontier in AI training
5. Why Edwin believes we’re still a decade away from AGI
6. Why taste and human judgment shape which AI models become industry leaders
7. His contrarian approach to company building that rejects Silicon Valley’s “pivot and blitzscale” playbook
8. How AI models will become increasingly differentiated based on the values of the companies building them
—
Brought to you by:
Vanta—Automate compliance. Simplify security.
WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs
Coda—The all-in-one collaborative workspace
—
Transcript: https://www.lennysnewsletter.com/p/surge-ai-edwin-chen
—
My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/180055059/my-biggest-takeaways-from-this-conversation
—
Where to find Edwin Chen:
• X: https://x.com/echen
• LinkedIn: https://www.linkedin.com/in/edwinzchen
• Surge’s blog: https://surgehq.ai/blog
—
Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
In this episode, we cover:
(00:00) Introduction to Edwin Chen
(04:48) AI’s role in business efficien…
-
Why LinkedIn is turning PMs into AI-powered "full stack builders” | Tomer Cohen (LinkedIn CPO)
4 december 2025 · 1 uur 8 min
Tomer Cohen is the longtime chief product officer at LinkedIn, where he’s pioneering the Full Stack Builder program, a radical new approach to product development that fully embraces what AI makes possible. Under his leadership, LinkedIn has scrapped its traditional Associate Product Manager program and replaced it with an Associate Product Builder program that teaches coding, design, and PM skills together. He’s also introduced a formal “Full Stack Builder” title and career ladder, enabling anyone from any function to take products from idea to launch. In this conversation, Tomer explains why product development has become too complex at most companies and how LinkedIn is building an AI-powered product team that can move faster, adapt more quickly, and do more with less. Lees meer
We discuss:
1. How 70% of the skills needed for jobs will change by 2030
2. The broken traditional model: organizational bloat slows features to a six-month cycle
3. The Full Stack Builder model
4. Three pillars of making FSB work: platform, agents, and culture (culture matters most)
5. Building specialized agents that critique ideas and find vulnerabilities
6. Why off-the-shelf AI tools never work on enterprise code without customization
7. Top performers adopt AI tools fastest, contrary to expectations about leveling effects
8. Change management tactics: celebrating wins, making tools exclusive, updating performance reviews
—
Brought to you by:
Vanta—Automate compliance. Simplify security: https://vanta.com/lenny
Figma Make—A prompt-to-code tool for making ideas real: https://www.figma.com/lenny/
Miro—The AI Innovation Workspace where teams discover, plan, and ship breakthrough products: https://miro.com/lenny
—
Transcript: https://www.lennysnewsletter.com/p/why-linkedin-is-replacing-pms
—
My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/180042347/my-takeaways-from-this-conversation
—
Where to find Tomer Cohen:
• LinkedIn: https://ww…
-
What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google)
30 november 2025 · 1 uur 26 min
Jeanne DeWitt Grosser built world-class GTM teams at Stripe, Google, and, most recently, Vercel, where she serves as COO and oversees marketing, sales, customer success, revenue operations, and field engineering. She transformed Stripe’s early sales organization from the ground up and advises founders on GTM strategy. Lees meer
We discuss:
1. Why GTM is becoming more strategically important in the AI era
2. The rise of the GTM engineer
3. A primer on segmentation
4. How to build a sales org that engineers and product teams respect
5. The changing calculus of build vs. buy for go-to-market tools in the AI era
6. Why most customers buy to avoid pain rather than to gain upside
—
Brought to you by:
Datadog—Now home to Eppo, the leading experimentation and feature flagging platform: https://www.datadoghq.com/lenny
Lovable—Build apps by simply chatting with AI: https://lovable.dev/
Stripe—Helping companies of all sizes grow revenue: https://stripe.com/
—
Transcript: https://www.lennysnewsletter.com/p/what-the-best-gtm-teams-do-differently
—
My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/179503137/my-biggest-takeaways-from-this-conversation
—
Where to find Jeanne DeWitt Grosser:
• X: https://x.com/jdewitt29
• LinkedIn: https://www.linkedin.com/in/jeannedewitt
—
Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
In this episode, we cover:
(00:00) Introduction to Jeanne DeWitt Grosser
(05:26) Defining go-to-market
(08:43) The evolution of go-to-market roles
(11:23) The rise of the go-to-market engineer
(14:21) Implementing AI in sales processes
(15:28) Optimizing sales with AI agents
(23:47) Defining sales roles: SDRs and AEs
(26:04) When to hire a GTM engineer
(29:04) Hiring and scaling sales teams
(30:50) The ideal go-to-market engineer
(34:24) The go-to-market tool stack
(40:39) Advice on bui…
-
A guide to difficult conversations, building high-trust teams, and designing a life you love | Rachel Lockett
23 november 2025 · 1 uur 45 min
Rachel Lockett is a sought-after executive coach and former HR leader at Stripe and Pinterest who now works with CEOs, founders, and tech leaders on emotional intelligence, resilience, and leadership skills. In this episode, Rachel shares powerful frameworks for coaching reports, having difficult conversations, avoiding burnout, and strengthening co-founder relationships. She also demonstrates these techniques through a live coaching session with me. Lees meer
We discuss:
* When to coach and when to just tell people what to do [09:00]
* The GROW technique for helping people figure out a solution for themselves [18:37]
* Techniques for making difficult conversations less difficult [01:20:28]
* Avoiding burnout and designing a more energizing career [41:55]
* Building and sustaining a healthy co-founder relationship [01:06:50]
* Creating a one-page plan that aligns your entire company [01:31:47]
* Practical ways AI is transforming executive coaching and leadership development [01:36:50]
* Why you should ask, “Would I enthusiastically rehire this person?” to clarify talent decisions [23:55]
Also on Spotify and Apple Podcasts
Brought to you by:
Stripe—Helping companies of all sizes grow revenue
Vanta—Automate compliance. Simplify security.
Persona—A global leader in digital identity verification
Where to find Rachel Lockett:
• LinkedIn: https://www.linkedin.com/in/rhlockett/
• Website: https://www.lockettcoaching.com
Referenced:
• One-page plan template: https://www.lockettcoaching.com/#resources
• Lockett Coaching Leadership Toolkit: https://www.dropbox.com/scl/fi/s74a9cn1ka1ebz6pglypf/Leadership-Toolkit_-Coaching-Rachel-Lockett.pdf?rlkey=yg2m9df2ziwy0fa6p0dt4gcfu&st=dgzvnf76&dl=0
• Renew Your Co-Founder Vows—and Other Tactics for Strengthening the Most Important Relationship in Your Startup: https://review.firstround.com/five-practices-to-strengthen-your-co-founder-relationship/
• First Round Guide to Co-Founder Check-Ins: https://docs.google.com/document…
-
Slack founder: Mental models for building products people love ft. Stewart Butterfield
20 november 2025 · 1 uur 31 min
Stewart Butterfield is the co-founder of Slack and Flickr, two of the most influential products in internet history. After selling Slack to Salesforce in one of tech’s biggest acquisitions, he’s been focused on family, philanthropy, and creative projects. In this rare podcast appearance, Stewart shares the product frameworks and leadership principles that most contributed to his success. From “utility curves” to “the owner’s delusion” to “hyper-realistic work-like activities,” his thoughts on craft, strategy, and leadership apply to anyone building products or leading teams. Lees meer
We discuss:
1. Hyper-realistic work-like activities
2. The owner’s delusion
3. Utility curves
4. “Don’t make me think”
5. “We don’t sell saddles here”
6. Tilting your umbrella
7. When to pivot
—
Brought to you by:
WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs
Metronome—Monetization infrastructure for modern software companies
Lovable—Build apps by simply chatting with AI
—
Transcript: https://www.lennysnewsletter.com/p/slack-founder-stewart-butterfield
—
My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/178320649/my-biggest-takeaways-from-this-conversation
—
Where to find Stewart Butterfield:
• X: https://x.com/stewart
• LinkedIn: https://www.linkedin.com/in/butterfield
—
Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
In this episode, we cover:
(00:00) Introduction to Stewart Butterfield
(04:58) Stewart’s current life and reflections
(06:44) Understanding utility curves
(10:13) The concept of divine discontent
(15:11) The importance of taste in product design
(19:03) Tilting your umbrella
(28:32) Balancing friction and comprehension
(45:07) The value of constant dissatisfaction
(47:06) Embracing continuous improvement
(50:03) The complexity of making things work
(54:27) Parkinson…
-
The Godmother of AI on jobs, robots, and why world models are next | Dr. Fei-Fei Li
16 november 2025 · 1 uur 20 min
Dr. Fei-Fei Li is known as the “godmother of AI.” She’s been at the center of AI’s biggest breakthroughs for over two decades. She spearheaded ImageNet, the dataset that sparked the deep-learning revolution we’re living right now, served as Google Cloud’s Chief AI Scientist, directed Stanford’s Artificial Intelligence Lab, and co-founded Stanford’s Institute for Human-Centered AI. In this conversation, Fei-Fei shares the rarely told history of how we got here—including the wild fact that just nine years ago, calling yourself an AI company was basically a death sentence. Lees meer
We discuss:
1. How ImageNet helped spark the AI explosion we’re living through
2. Why world models and spatial intelligence represent the next frontier in AI, beyond large language models
3. Why Fei-Fei believes AI won’t replace humans but will require us to take responsibility for ourselves
4. The surprising applications of Marble, from movie production to psychological research
5. Why robotics faces unique challenges compared with language models and what’s needed to overcome them
6. How to participate in AI regardless of your role
—
Brought to you by:
Figma Make—A prompt-to-code tool for making ideas real
Justworks—The all-in-one HR solution for managing your small business with confidence
Sinch—Build messaging, email, and calling into your product
—
Transcript: https://www.lennysnewsletter.com/p/the-godmother-of-ai
—
My biggest takeaways (for paid newsletter subscribers):
https://www.lennysnewsletter.com/i/178223233/my-biggest-takeaways-from-this-conversation
—
Where to find Dr. Fei-Fei Li
• X: https://x.com/drfeifei
• LinkedIn: https://www.linkedin.com/in/fei-fei-li-4541247
• World Labs: https://www.worldlabs.ai
—
Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
In this episode, we cover:
(00:00) Introduction to Dr. Fei-Fei Li
(05:31) The evolution of AI
… -
“Dumbest idea I’ve heard” to $100M ARR: Inside the rise of Gamma | Grant Lee (CEO)
13 november 2025 · 1 uur 54 min
Grant Lee is the co-founder of Gamma, the AI-powered presentation tool that’s one of the hottest and most interesting AI startups in the world right now. They’re valued at over $2 billion, and they hit $100 million ARR in just over two years, with a lean team of just around 30 people. Unlike many fast-growing AI startups, Gamma has been profitable for most of its history, has not raised significant funding, and they built a massive business in a category most investors dismissed. In fact, one investor told Grant his idea was “the dumbest idea he had ever heard.” Lees meer
We discuss:
• How Gamma found product-market fit by rethinking their onboarding
• Their process for building a “word-of-mouth machine”
• How they leveraged more than 1,000 micro-influencers instead of big names
• Why focusing on the “first 30 seconds” transformed their business
• Their approach to pricing that led to profitability within months
• How Grant thinks about building a durable “GPT wrapper” business
—
Brought to you by:
Vanta—Automate compliance. Simplify security.
Justworks—The all-in-one HR solution for managing your small business with confidence
Miro—A collaborative visual platform where your best work comes to life
—
Where to find Grant Lee:
• X: https://x.com/thisisgrantlee
• LinkedIn: https://www.linkedin.com/in/grantslee
—
Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
In this episode, we cover:
(00:00) Introduction to Grant Lee and Gamma
(05:59) The founding story of Gamma
(09:52) Achieving product-market fit
(15:43) Self-awareness as a founder
(17:17) The power of onboarding
(20:41) The original insight that led to Gamma
(22:42) Founder-led marketing and growth tactics
(29:20) Sharing online
(37:40) Getting to $100M ARR
(41:19) Influencer marketing as a growth strategy
(54:08) Virality is not an accident
(58:30) Investing in brand before pai…
-
"Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel
9 november 2025 · 1 uur 22 min
Jen Abel is GM of Enterprise at State Affairs and co-founded Jellyfish, a consultancy that helps founders learn zero-to-one enterprise sales. She’s one of the smartest people I’ve ever met on learning enterprise sales, and in this follow-up to our first chat two years ago (covering the zero to $1 million ARR founder-led sales phase), we focus on the skills founders need to learn to go from $1M to $10M ARR. Lees meer
We discuss:
1. Why the “mid-market” doesn’t exist
2. Why tier-one logos like Stripe and Tesla counterintuitively make the best early customers
3. The dangers of pricing your product at $10K-$20K
4. Why you need to vision-cast instead of problem-solve to win enterprise deals
5. Why services are the fastest way to get your foot in the door with enterprises
6. How to find and work with design partners
7. When to hire your first salesperson and what profile to look for
—
Brought to you by:
WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs
Lovable—Build apps by simply chatting with AI
Coda—The all-in-one collaborative workspace
—
Where to find Jen Abel:
• X: https://x.com/jjen_abel
• LinkedIn: https://www.linkedin.com/in/earlystagesales
• Website: https://www.jjellyfish.com
—
Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
In this episode, we cover:
(00:00) Welcome back, Jen!
(04:38) The myth of the mid-market
(08:08) Targeting tier-one logos
(10:50) Vision-casting vs. problem-selling
(15:35) The importance of high ACVs
(20:45) Don’t play the small business game with an enterprise company
(25:09) Design partners: the double-edged sword
(28:11) Finding the right company
(36:55) Enterprise sales: the art of the deal
(43:21) The problem with channel partnerships
(44:41) Quick summary
(50:24) Hiring the right enterprise salespeople
(56:49) Structuring sales compensation
(01:01:01) Building relationship…
-
The woman behind Canva shares how she built a $42B company from nothing | Melanie Perkins
2 november 2025 · 1 uur 6 min
Melanie Perkins is CEO and co-founder of Canva, currently valued at over $42 billion, generating over $3 billion in annual revenue, with more than 240 million monthly active users and, incredibly, eight consecutive years of profitability. But the journey was far from smooth. Melanie was rejected by over 100 investors during her first fundraising round, her team spent two years without being able to ship a new feature during a technical rewrite, and the company pivoted early from a yearbook publishing platform to become the design powerhouse it is today. Through it all, she maintained what she calls “column B” thinking: building toward a dream future rather than just using the bricks around you. Lees meer
We discuss:
1. How “column B” thinking helped Melanie build Canva, by starting with an impossible vision rather than existing constraints
2. The power of setting “crazy big goals”
3. How Canva survived a painful two-year period without shipping any new features while rewriting their codebase
4. How Melanie pushed through 100 investor rejections, and how she used each rejection to strengthen her pitch
5. Canva’s “two-step plan”: build one of the world’s most valuable companies, then do the most good possible
6. Melanie’s vision for 2050 and why she believes imagination is the first step toward a better world
—
Brought to you by:
Vanta—Automate compliance. Simplify security. https://vanta.com/lenny
Stripe—Helping companies of all sizes grow revenue: https://stripe.com/
Justworks—The all-in-one HR solution for managing your small business with confidence: https://www.justworks.com
—
Transcript: https://www.lennysnewsletter.com/p/the-making-of-canva
—
My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/176082995/my-biggest-takeaways-from-this-conversation
—
Where to find Melanie Perkins:
• X: https://x.com/melaniecanva
• LinkedIn: https://www.linkedin.com/in/melanieperkins/
—
Where to find Lenny:
• Newsletter: http…
-
How Block is becoming the most AI-native enterprise in the world | Dhanji R. Prasanna
26 oktober 2025 · 1 uur 27 min
Dhanji R. Prasanna is the chief technology officer at Block (formerly Square), where he’s managed more than 4,000 engineers over the past two years. Under his leadership, Block has become one of the most AI-native large companies in the world. Before becoming CTO, Dhanji wrote an “AI manifesto” to CEO Jack Dorsey that sparked a company-wide transformation (and his promotion to CTO). Lees meer
We discuss:
1. How Block’s internal open-source agent, called Goose, is saving employees 8 to 10 hours weekly
2. How the company measures AI productivity gains across technical and non-technical teams
3. Which teams are benefiting most from AI (it’s not engineering)
4. The boring organizational change that boosted productivity even more than AI tools
5. Why code quality has almost nothing to do with product success
6. How to drive AI adoption throughout an organization (hint: leadership needs to use the tools daily)
7. Lessons from building Google Wave, Google+, and other failed products
—
Brought to you by:
Sinch—Build messaging, email, and calling into your product: https://sinch.com/lenny
Figma Make—A prompt-to-code tool for making ideas real: https://www.figma.com/lenny/
Persona—A global leader in digital identity verification: https://withpersona.com/lenny
—
Where to find Dhanji R. Prasanna:
• LinkedIn: https://www.linkedin.com/in/dhanji/
—
Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
In this episode, we cover:
(00:00) Introduction to Dhanji
(05:26) The AI manifesto: convincing Jack Dorsey
(07:33) Transforming into a more AI-native company
(12:05) How engineering teams work differently today
(15:24) Goose: Block’s open-source AI agent
(20:18) Measuring AI productivity gains across teams
(21:38) What Goose is and how it works
(32:15) The future of AI in engineering and productivity
(37:42) The importance of human taste
(40:10) Building v…
-
Al Engineering 101 with Chip Huyen (Nvidia, Stanford, Netflix)
23 oktober 2025 · 1 uur 23 min
Chip Huyen is a core developer on Nvidia’s Nemo platform, a former AI researcher at Netflix, and taught machine learning at Stanford. She’s a two-time founder and the author of two widely read books on AI, including AI Engineering, which has been the most-read book on the O’Reilly platform since its launch. Unlike many AI commentators, Chip has built multiple successful AI products and platforms and works directly with enterprises on their AI strategies, giving her unique visibility into what’s actually happening inside companies building AI products. Lees meer
We discuss:
1. What people think makes AI apps better vs. what actually makes AI apps better
2. What pre-training vs. post-training is, and why fine-tuning should be your last resort
3. How RLHF (reinforcement learning from human feedback) actually works
4. Why data quality matters more than which vector database you choose
5. Why high performers are seeing the most gains from AI coding tools
6. Why most AI problems are actually UX issues
—
Brought to you by:
Dscout—The UX platform to capture insights at every stage: from ideation to production: https://www.dscout.com/
Justworks—The all-in-one HR solution for managing your small business with confidence: https://www.justworks.com
Persona—A global leader in digital identity verification: https://withpersona.com/lenny
—
Where to find Chip Huyen:
• X: https://x.com/chipro
• LinkedIn: https://www.linkedin.com/in/chiphuyen/
• Website: https://huyenchip.com/
• Substack: https://substack.com/@chiphuyen
—
Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
In this episode, we cover:
(00:00) Introduction to Chip Huyen
(04:28) Chip’s viral LinkedIn post
(07:05) Understanding AI training: pre-training vs. post-training
(08:50) Language modeling explained
(13:55) The importance of post-training
(15:20) Reinforcement learning and human feedback…
-
How to measure AI developer productivity in 2025 | Nicole Forsgren
19 oktober 2025 · 1 uur 8 min
Nicole Forsgren created the most widely used frameworks for measuring developer productivity—DORA and SPACE. She wrote the foundational book Accelerate and is about to release her newest book, Frictionless, a practical guide for helping teams move faster in the AI era. She’s currently Senior Director of Developer Intelligence at Google. Lees meer
We discuss:
1. Why most productivity metrics are a lie
2. Signs that your engineering team could be moving much faster
3. Why AI accelerates coding but developers aren’t speeding up as much as you think
4. AI’s impact on engineers getting into “flow”
5. Her framework for building and scaling a developer experience team
6. The three components of developer experience: flow state, cognitive load, and feedback loops
—
Brought to you by:
Mercury—The art of simplified finances: https://mercury.com/
WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs: https://workos.com/lenny
Coda—The all-in-one collaborative workspace: https://coda.io/lenny
—
Where to find Nicole Forsgren:
• Twitter: https://twitter.com/nicolefv
• LinkedIn: https://www.linkedin.com/in/nicolefv/
• Website: https://nicolefv.com/
—
Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
In this episode, we cover:
(00:00) Introduction to Nicole Forsgren
(05:09) The concept of developer experience (DevEx)
(08:33) Flow state and cognitive load in the age of AI
(12:02) Challenges in measuring productivity with AI
(21:19) The importance of developer experience for business value
(22:20) Common issues and solutions in developer experience
(26:49) Signs your eng team is moving too slow
(29:52) How AI is improving productivity
(33:32) Real examples of productivity improvements
(36:35) Introducing her new book, Frictionless
(43:40) How to get started building a DevEx team
(45:15) The impact of forming developer experience tea…
-
Figma’s CEO: Why AI makes design, craft, and quality the new moat for startups | Dylan Field
16 oktober 2025 · 1 uur 27 min
Dylan Field is co-founder and CEO of Figma, a beloved tool used by every modern product team. Founded in 2012, Figma has expanded from a single design tool to a comprehensive platform including FigJam, Slides, Dev Mode, and, most recently, Figma Make. After a $20 billion acquisition by Adobe fell through due to regulatory pushback, Dylan led the company to a successful IPO in 2025. Lees meer
What you’ll learn:
• How Dylan kept internal morale up after the Adobe acquisition fell through
• His approach to maintaining pace and a sense of urgency 13 years in
• How to systematically develop taste
• How Figma decides which product lines to add
• Why Dylan obsesses over “time to value”
• How AI is making design more valuable
—
Brought to you by:
Stripe—Helping companies of all sizes grow revenue
—
Transcript: https://www.lennysnewsletter.com/p/why-ai-makes-design-craft-and-quality-the-new-moat
—
My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/175569466/my-biggest-takeaways-from-this-conversation
—
Where to find Dylan Field:
• X: https://x.com/zoink
• LinkedIn: https://www.linkedin.com/in/dylanfield/
—
Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
In this episode, we cover:
(00:00) Introduction to Dylan Field
(03:58) The Adobe deal fallout
(05:50) Maintaining team morale post-deal
(09:13) Strategies for sustaining high performance
(13:37) Maintaining Figma’s unique company culture
(16:22) Dylan’s leadership evolution
(21:03) How to improve clarity as a leader
(24:40) The controversy behind FigJam
(31:06) Lessons from expanding Figma’s core product line
(39:32) Time-to-value
(45:14) Introduction to Figma Make
(48:26) AI app prototyping and the future of Figma Make
(53:38) Lessons from Figma’s AI product launch
(57:47) The importance of craft
(59:54) Developing good taste
(01:05:35) The…
-
Inside Google's AI turnaround: The rise of AI Mode, strategy behind AI Overviews, and their vision for AI-powered search | Robby Stein (VP of Product, Google Search)
11 oktober 2025 · 1 uur 22 min
Robby Stein is VP of Product at Google, where he oversees the core products of Google Search—including the new AI Overviews, AI Mode, search ranking, Google Lens, and more. Previously, he led consumer products at Instagram, where he and his teams built Stories, Reels, Close Friends, and other key features now used by billions. Lees meer
—
What you’ll learn:
Why Google’s AI products are suddenly taking off after years of perceived stagnation
How AI is expanding Search rather than replacing it, contrary to what many predicted
The three core product principles that have helped Robby build multiple billion-user products
Inside Instagram’s decision to build its own version of Snapchat Stories
His mantra of “relentless improvement”
How Google developed AI Mode from concept to launch in just one year
Why most teams give up too early on potentially transformative products
—
Brought to you by:
Vanta—Automate compliance. Simplify security: https://vanta.com/lenny
Jira Product Discovery—Confidence to build the right thing: https://atlassian.com/lenny/?utm_source=lennypodcast&utm_medium=paid-audio&utm_campaign=fy24q1-jpd-imc
Orkes—The enterprise platform for reliable applications and agentic workflows: https://www.orkes.io/
—
Transcript: https://www.lennysnewsletter.com/p/how-google-built-ai-mode-in-under-a-year
—
My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/175041217/my-biggest-takeaways-from-this-conversation
—
Where to find Robby Stein:
• X: https://x.com/rmstein
• LinkedIn: https://www.linkedin.com/in/robbystein/
—
Referenced:
• Google Gemini: https://gemini.google.com/app
• Nano Banana: https://aistudio.google.com/models/gemini-2-5-flash-image
• Chat GPT: https://chatgpt.com/
• Perplexity: https://www.perplexity.ai/
• Google Lens: https://lens.google/
• AI Google search: https://www.google.com/ai
• Why ChatGPT will be the next big growth channel (and how to capitalize on it) | Brian Balfour (Reforge): ht…
-
First interview with Scale AI’s CEO: $14B Meta deal, what’s working in enterprise AI, and what frontier labs are building next | Jason Droege
9 oktober 2025 · 1 uur 24 min
Jason Droege is the CEO of Scale AI, a company that provides foundational training data to every major AI lab. He previously co-founded Scour with Travis Kalanick and built Uber Eats from idea to $20 billion in revenue. In this conversation, Jason shares lessons from getting sued for $250 billion, discovering restaurant economics by weighing sandwich ingredients, and over 25 years of launching transformative technology businesses. Lees meer
What you’ll learn:
What actually happened with Meta’s $14 billion investment in Scale AI
Why AI models still need human experts to improve, and how that relationship is evolving
How AI models learn from experts building websites and debugging code
The business lessons from building Uber Eats from zero to $20 billion
Why most enterprise data is useless for AI models today
Why urgent daily problems beat super-valuable occasional problems when building products
How to think independently when building new products and businesses
—
Brought to you by:
Merge—The fastest way to ship 220+ integrations: http://merge.dev/lenny
Figma Make—A prompt-to-code tool for making ideas real: https://www.figma.com/lenny/
Mercury—The art of simplified finances: https://mercury.com/
—
Transcript: https://www.lennysnewsletter.com/p/first-interview-with-scale-ais-ceo-jason-droege
—
My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/174979621/my-biggest-takeaways-from-this-conversation
—
Where to find Jason Droege:
• X: https://x.com/jdroege
• LinkedIn: https://www.linkedin.com/in/jasondroege/
—
Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
In this episode, we cover:
(00:00) Introduction to Jason Droege
(06:01) Jason’s early career and lessons learned
(10:27) The current state of Scale AI
(12:37) The shift to expert data labeling
(17:02) Challenges and strategies in finding expert…
-
How to find hidden growth opportunities in your product | Albert Cheng (Duolingo, Grammarly, Chess.com)
5 oktober 2025 · 1 uur 25 min
Albert Cheng has led growth at three of the world’s most successful consumer subscription companies: Duolingo, Grammarly, and Chess.com. A former Google product manager (and serious pianist!), Albert developed a unique approach to finding and scaling growth opportunities through rapid experimentation and deep user psychology. His teams run 1,000 experiments a year, discovering counterintuitive insights that have driven tens of millions in revenue. Lees meer
What you’ll learn:
1. How to use the explore-exploit framework to find new growth opportunities
2. How showing premium features to free users doubled Grammarly’s upgrades to paid plans
3. What good retention looks like for a consumer subscription app
4. Why resurrected users drive 80% of mature product growth
5. Why “reverse trials” work better than time-based trials
6. The three pillars of successful gamification: core loop, metagame, and profile
—
Brought to you by:
Vanta—Automate compliance. Simplify security.
Jira Product Discovery—Confidence to build the right thing
Miro—A collaborative visual platform where your best work comes to life
—
Where to find Albert Cheng:
• X: https://x.com/albertc248
• LinkedIn: https://www.linkedin.com/in/albertcheng1/
• Chess.com: https://www.chess.com/member/Goniners
—
Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
Referenced:
• How Duolingo reignited user growth: https://www.lennysnewsletter.com/p/how-duolingo-reignited-user-growth
• Inside ChatGPT: The fastest-growing product in history | Nick Turley (Head of ChatGPT at OpenAI): https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley
• Explore vs. Exploit: https://brianbalfour.com/quick-takes/explore-vs-exploit
• Grammarly: https://www.grammarly.com/
• Reforge: https://www.reforge.com/
• Chess.com: https://www.chess.com/
• Everyone’s an engineer now: Inside v0’s mission to create a hund…
-
A 4-step framework for building delightful products | Nesrine Changuel (Spotify, Google, Skype)
28 september 2025 · 1 uur 24 min
Nesrine Changuel helped build Spotify, Google Chrome, and Google Meet. Her work has helped her discover the importance of emotional connection in building successful products. At Google, she served as a dedicated “delight PM,” a role specifically focused on making products more delightful. She recently published Product Delight, a book that provides a practical framework for creating products that serve both functional and emotional needs. Based in Paris, she now coaches founders and CPOs on implementing delight strategies in their organizations. Lees meer
What you’ll learn:
1. Why delight is a business strategy, not just “sprinkling confetti” on top of functionality
2. How to identify emotional motivators that drive product retention
3. The 50-40-10 rule for balancing delight in your roadmap
4. The 4-step delight model
5. The origin story of Spotify’s Discover Weekly
6. Why B2B products need delight just as much as B2C products
7. How to get buy-in from skeptical leaders who think delight is a luxury
—
Brought to you by:
DX—The developer intelligence platform designed by leading researchers: https://getdx.com/lenny
Jira Product Discovery—Confidence to build the right thing: https://atlassian.com/lenny
LucidLink—Real-time cloud storage for teams: https://www.lucidlink.com/lenny
—
Transcript: https://www.lennysnewsletter.com/p/a-4-step-framework-for-building-delightful-products
—
My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/174199489/my-biggest-takeaways-from-this-conversation
—
Where to find Nesrine Changuel:
• LinkedIn: https://www.linkedin.com/in/nesrinechanguel/
• Newsletter: https://nesrinechanguel.substack.com/
• Website: https://nesrine-changuel.com/
—
Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
In this episode, we cover:
(00:00) Introduction to Nesrine and product delight
(04:56…
-
Why AI evals are the hottest new skill for product builders | Hamel Husain & Shreya Shankar (creators of the #1 eval course)
25 september 2025 · 1 uur 47 min
Hamel Husain and Shreya Shankar teach the world’s most popular course on AI evals and have trained over 2,000 PMs and engineers (including many teams at OpenAI and Anthropic). In this conversation, they demystify the process of developing effective evals, walk through real examples, and share practical techniques that’ll help you improve your AI product. Lees meer
What you’ll learn:
1. WTF evals are
2. Why they’ve become the most important new skill for AI product builders
3. A step-by-step walkthrough of how to create an effective eval
4. A deep dive into error analysis, open coding, and axial coding
5. Code-based evals vs. LLM-as-judge
6. The most common pitfalls and how to avoid them
7. Practical tips for implementing evals with minimal time investment (30 minutes per week after initial setup)
8. Insight into the debate between “vibes” and systematic evals
—
Brought to you by:
Fin—The #1 AI agent for customer service
Dscout—The UX platform to capture insights at every stage: from ideation to production
Mercury—The art of simplified finances
—
Where to find Shreya Shankar
• X: https://x.com/sh_reya
• LinkedIn: https://www.linkedin.com/in/shrshnk/
• Website: https://www.sh-reya.com/
• Maven course: https://bit.ly/4myp27m
—
Where to find Hamel Husain
• X: https://x.com/HamelHusain
• LinkedIn: https://www.linkedin.com/in/hamelhusain/
• Website: https://hamel.dev/
• Maven course: https://bit.ly/4myp27m
—
In this episode, we cover:
(00:00) Introduction to Hamel and Shreya
(04:57) What are evals?
(09:56) Demo: Examining real traces from a property management AI assistant
(16:51) Writing notes on errors
(23:54) Why LLMs can’t replace humans in the initial error analysis
(25:16) The concept of a “benevolent dictator” in the eval process
(28:07) Theoretical saturation: when to stop
(31:39) Using axial codes to help categorize and synthesize error notes
(44:39) The results
(46:06) Building an LLM-as-judge to evaluate specific failure modes
(48:…
-
From managing people to managing AI: The leadership skills everyone needs now | Julie Zhuo (Facebook VP, Sundial CEO, The Making of a Manager author)
21 september 2025 · 1 uur 36 min
Julie Zhuo is the former VP and Head of Design at Facebook (now Meta), author of the bestselling book The Making of a Manager, and co-founder of Sundial, an AI-powered data analysis company. Also, my first-ever podcast guest over 3 years ago! Lees meer
In our conversation, we discuss:
1. The three core manager skills that translate directly to managing AI agents
2. How her team uses AI to learn new skills 10x faster
3. The “diagnose with data, treat with design” framework for balancing gut and data
4. Why hypergrowth AI companies have terrible data infrastructure (and why it doesn’t matter)
5. How to give feedback that actually lands—including Julie’s exact script for difficult conversations
6. What Julie’s teaching her kids about an AI future (hint: it’s not coding or STEM)
—
Brought to you by:
Mercury — The art of simplified finances
DX — The developer intelligence platform designed by leading researchers
PostHog—How developers build successful products
—
Transcript: https://www.lennysnewsletter.com/p/from-managing-people-to-managing-ai-julie-zhuo
—
My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/172723725/my-biggest-takeaways-from-this-conversation
—
Where to find Julie Zhuo:
• X: https://x.com/joulee
• LinkedIn: https://www.linkedin.com/in/julie-zhuo/
• Website: https://www.juliezhuo.com/
• Newsletter: https://lg.substack.com/
• Sundial: https://sundial.so/
—
Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
In this episode, we cover:
(00:00) Welcome back, Julie!
(05:18) The success of The Making of a Manager
(08:41) Why AI will make everyone a manager
(11:38) The future of management roles
(14:00) Empowering teams with AI
(21:30) Specific roles being accelerated by AI
(26:53) Data analysis in AI companies
(32:02) The role of data in design
(37:21) The evolving role of managers in t…
-
Why experts writing AI evals is creating the fastest-growing companies in history | Brendan Foody (CEO of Mercor)
18 september 2025 · 1 uur 7 min
Brendan Foody is the CEO and co-founder of Mercor, the fastest-growing company in history to go from $1M to $500M in revenue (in just 17 months!). At 22, he is also the youngest American unicorn founder ever. Mercor works with 6 of the Magnificent 7 and all top 5 AI labs to help them hire experts to create evaluations and training data that improve their models. In this conversation, Brendan explains why evals have become the critical bottleneck for AI progress, how he discovered this massive opportunity, and what the future of work might look like in an AI-driven economy. Lees meer
What you’ll learn:
1. Why evals are becoming the primary bottleneck for AI progress and what this means for AI startups
2. How Mercor grew to $500M revenue in 17 months (fastest in history)
3. Brendan’s meeting with xAI that changed his company’s trajectory
4. Which skills and jobs will remain most valuable as AI continues to advance (hint: jobs with “elastic” demand)
5. Why Brendan believes AGI and superintelligence are not happening anytime soon
6. The three unique core values that drove Mercor’s success
7. How Harvard Lampoon writers are making Claude funnier
—
Brought to you by:
WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs
Jira Product Discovery—Atlassian’s new prioritization and roadmapping tool built for product teams
Enterpret—Transform customer feedback into product growth
—
Transcript: https://www.lennysnewsletter.com/p/experts-writing-ai-evals-brendan-foody
—
My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/173303790/my-biggest-takeaways-from-this-conversation
—
Where to find Brendan Foody:
• X: https://x.com/BrendanFoody
• LinkedIn: https://www.linkedin.com/in/brendan-foody-2995ab10b/
—
Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
In this episode, we cover:
(00:00) Introductio…
-
The ultimate guide to AEO: How to get ChatGPT to recommend your product | Ethan Smith (Graphite)
14 september 2025 · 1 uur 12 min
Ethan Smith is the CEO of Graphite—the leading SEO growth agency—and my go-to expert on SEO. After 18 years of mastering traditional SEO, Ethan has been at the forefront of what is called AEO: answer engine optimization, or, more simply, getting your product to show up in ChatGPT/Claude/Gemini/Perplexity answers. He’s discovered that ChatGPT traffic converts six times better than Google search—and most companies are completely missing this opportunity. Lees meer
In our conversation, we discuss:
1. His 7-step playbook to rank #1 in ChatGPT
2. Why ChatGPT traffic converts 6x better than Google
3. How early-stage startups can win at AEO immediately (unlike with SEO, which takes years)
4. The three tactics that actually work: landing pages, YouTube videos, and Reddit comments
5. Why help-center content can suddenly be your highest-ROI investment
6. The specific Reddit strategy that works (spoiler: be authentic)
7. Why AI-generated content doesn’t work
—
Brought to you by:
Orkes—The enterprise platform for reliable applications and agentic workflows
Vanta—Automate compliance. Simplify security.
Great Question—Empower everyone to run great research
—
Where to find Ethan Smith:
• Twitter: https://twitter.com/ethan_l_s
• LinkedIn: https://bit.ly/ethans-linkedin
• Graphite: https://graphite.io/
• Graphite Research Papers: https://bit.ly/graphite-five-percent
—
Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
In this episode, we cover:
(00:00) Welcome back, Ethan
(04:34) The changing landscape of SEO
(06:19) AEO (answer engine optimization) vs. GEO (generative engine optimization)
(08:13) The impact of AEO
(11:51) How early-stage startups can win at AEO
(14:34) The quality of AEO leads
(15:35) On-site vs. off-site traffic
(16:32) Reddit’s role in AEO and avoiding spam
(20:11) How AI models use citations (RAG)
(21:41) Key principles for winn…
-
$46B of hard truths from Ben Horowitz: Why founders fail and why you need to run toward fear (a16z co-founder)
11 september 2025 · 1 uur 38 min
Ben Horowitz is the co-founder of Andreessen Horowitz, Silicon Valley’s largest and most influential venture capital firm, with over $46B in committed capital across multiple funds. He took Loudcloud public with just $2 million in revenue (dubbed “the IPO from hell”), sold it for $1.6 billion, and has backed companies from Facebook to Stripe to Airbnb to OpenAI to Databricks (now worth more than $100 billion). His management philosophy—forged through near-death experiences and refined through coaching hundreds of CEOs—contradicts most conventional startup wisdom. Lees meer
In our conversation, Ben shares:
1. Why “founder mode” is half right and half dangerously wrong
2. The story behind “Good Product Manager/Bad Product Manager” and why it went viral despite being written in anger
3. Where the biggest AI startup opportunities remain
4. Why you need to run toward fear, never away
5. The one trait that predicts that a founder will fail as CEO
6. Inside Paid in Full, Ben’s nonprofit awarding pensions to pioneering hip-hop artists
—
Brought to you by:
DX—The developer intelligence platform designed by leading researchers: http://getdx.com/lenny
Basecamp—The famously straightforward project management system from 37signals: https://www.basecamp.com/lenny
Miro—A collaborative visual platform where your best work comes to life: https://miro.com/lenny
—
Transcript: https://www.lennysnewsletter.com/p/46b-of-hard-truths-from-ben-horowitz
—
My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/172439345/my-biggest-takeaways-from-this-conversation
—
Where to find Ben Horowitz:
• X: https://x.com/bhorowitz
• LinkedIn: https://www.linkedin.com/in/behorowitz/
• Website: https://benhorowitz.com/
• Andreessen Horowitz’s website: https://a16z.com/
—
Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
In this episode, we …
-
How AI is reshaping the product role | Oji and Ezinne Udezue
7 september 2025 · 1 uur 18 min
Ezinne and Oji Udezue have over 50 years of combined product leadership experience at Microsoft, Twitter, Atlassian, WP Engine, Typeform, and Calendly. They’ve witnessed every major shift in product management, and, despite their seniority, they’re taking beginner AI courses and learning from engineers half their age, and Oji is coding more now than in the past decade—from Waterfall to Agile to AI. They are also the authors of Building Rocketships, a guide to building great products. In this conversation, the couple shares hard-won lessons they’ve learned from companies successfully adapting to AI, including their “shipyard” framework and their “sharp problem” methodology. Lees meer
What you’ll learn:
1. The “shipyard” framework: why the best AI teams embrace controlled chaos
2. Why Oji writes more code now than in the past 10 years—despite being a PM for more than 25 years
3. The three skills that matter most for PMs in 2025: curiosity, humility, and agency
4. How to identify “sharp problems”
5. AI at the core vs. AI at the edge: why companies that are building entirely new AI-centric codebases will beat those just “sprinkling AI” on existing products
6. The counterintuitive truth: engineers are moving so fast with AI that PMs are now the bottleneck
7. Their biggest product lesson from 50 combined years
—
Brought to you by:
Mercury—The art of simplified finances
Vanta—Automate compliance. Simplify security.
Coda—The all-in-one collaborative workspace
—
Where to find Oji and Ezinne:
• ProductMind on Substack: https://substack.com/@ojiudezue
• ProductMind on LinkedIn: https://www.linkedin.com/company/productmindco
• ProductMind on YouTube: https://www.youtube.com/@ProductMindX/videos
• ProductMind on Spotify: https://open.spotify.com/show/07OVh5pdSv0szHPwWktzQQ
• ProductMind website: https://www.productmind.co/
• Oji on LinkedIn: https://www.linkedin.com/in/ojiudezue/
• Ezinne on LinkedIn: https://www.linkedin.com/in/ezinne/
—
Where to find Lenny:
• N…
-
How we restructured Airtable’s entire org for AI | Howie Liu (co-founder and CEO)
31 augustus 2025 · 1 uur 41 min
Howie Liu is the co-founder and CEO of Airtable, the no-code platform valued at around $12 billion. After a viral tweet declared “Airtable is dead” based on incorrect data, Howie led a radical transformation: reorganizing the entire company around AI, becoming an “IC CEO” who codes daily, and achieving over $100 million in free cash flow. Lees meer
What you’ll learn:
1. The “fast thinking” vs. “slow thinking” team structure that lets Airtable ship AI features weekly (inspired by Daniel Kahneman)
2. Why Howie uses AI hourly (not daily) and is Airtable’s #1 inference-cost user globally
3. Why CEOs must become ICs again in the AI era (and how to restructure your calendar to make it possible)
4. Why “playing” with AI tools should be mandatory—Howie tells employees to cancel all meetings for a week to experiment
5. The specific skills product managers, engineers, and designers need to develop to succeed in the AI era
6. Why evals can kill innovation (and when to use “vibes” instead)
—
Brought to you by:
LucidLink—Real-time cloud storage for teams
DX—The developer intelligence platform designed by leading researchers
Claude.ai—The AI for problem solvers and enterprise
—
Where to find Howie Liu
• X: https://x.com/howietl
• LinkedIn: https://www.linkedin.com/in/howieliu/
• Email: howie@airtable.com
—
Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
In this episode, we cover:
(00:00) Introduction to Howie Liu and Airtable
(04:05) The “Airtable is dead” viral tweet controversy
(08:07) The rise of IC CEOs
(10:57) AI’s paradigm shift in product development
(16:27) Specific changes Airtable has made
(21:38) Fast- and slow-thinking teams
(32:57) The emergence of new form factors in AI models
(34:48) Airtable’s vision and philosophy
(40:20) Empowering teams with AI tools
(46:50) Encouraging experimentation and play
(50:55) Cross-functional skills…
-
How 80,000 companies build with AI: products as organisms, the death of org charts, and why agents will outnumber employees by 2026 | Asha Sharma (CVP of AI Platform at Microsoft)
28 augustus 2025 · 57 min
Asha Sharma leads AI product strategy at Microsoft, where she works with thousands of companies building AI products and has unique visibility into what’s working (and what’s not) across more than 15,000 startups and enterprises. Before Microsoft, Asha was COO at Instacart, and VP of Product & Engineering at Meta, notably leading product for Messenger. Lees meer
What you’ll learn:
1. Why we’re moving from “product as artifact” to “product as organism” and what this means for builders
2. Microsoft’s “seasons” planning framework that allows them to adapt quickly in the AI era
3. The death of the org chart: how agents are turning hierarchies into task networks and why “the loop, not the lane” is the new organizing principle
4. Why post-training will soon see more investment than pre-training—and how to build your own AI moat with fine-tuning
5. Her prediction for the “agentic society”—where org charts become work charts and agents outnumber humans in your company
6. The three-phase pattern every successful AI company follows (and why most fail at phase one)
7. The rise of code-native interfaces and why GUIs might be going the way of the desktop
8. What Asha learned from Satya Nadella about optimism
—
Brought to you by:
Enterpret—Transform customer feedback into product growth: https://enterpret.com/lenny
DX—The developer intelligence platform designed by leading researchers: http://getdx.com/lenny
Fin—The #1 AI agent for customer service: https://fin.ai/lenny
—
Transcript: https://www.lennysnewsletter.com/p/how-80000-companies-build-with-ai-asha-sharma
—
My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/171413445/my-biggest-takeaways-from-this-conversation
—
Where to find Asha Sharma:
• LinkedIn: https://www.linkedin.com/in/aboutasha/
• Blog: https://azure.microsoft.com/en-us/blog/author/asha-sharma/
—
Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• Lin…
-
Inside the expert network training every frontier AI model | Garrett Lord (Handshake CEO)
24 augustus 2025 · 1 uur 10 min
Garrett Lord is co-founder and CEO of Handshake, which started as a career network for college students and new grads but recently discovered something extraordinary: they were sitting on the world’s largest network of academic experts—exactly what frontier AI labs desperately needed. With 500,000 PhDs and 3 million advanced degree holders creating training data, in just eight months they’ve built a new business that hit $50 million in revenue in its first four months and is on track to blow past $100M in the first 12 months. Lees meer
What you’ll learn:
1. How Handshake found an opportunity to leverage their proprietary network of experts to launch a data-labeling business that’s on track to blow past $100 million ARR in 12 months
2. Why AI models need human experts (e.g. physics PhDs) to improve, and what this “data labeling” actually involves
3. Inside the actual work: what a biology PhD does for 8 hours that makes GPT-5 smarter
4. The playbook for building a startup inside a startup: separate teams, separate offices, separate everything
5. Why the shift from “generalist” to “expert” data labeling created a once-in-a-lifetime business opportunity
6. Why AI won’t eliminate entry-level jobs—it’s creating “Iron Man suits” that make junior employees 10x more productive
—
Brought to you by:
CodeRabbit—Cut code review time and bugs in half. Instantly: https://coderabbit.link/lenny
Orkes—The enterprise platform for reliable applications and agentic workflows: https://www.orkes.io/
Claude.ai—The AI for problem solvers and enterprise: http://claude.ai/
—
Transcript: https://www.lennysnewsletter.com/p/inside-handshake-garrett-lord
—
My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/171410958/my-biggest-takeaways-from-this-conversation
—
Where to find Garrett Lord:
• X: https://x.com/garrettlord
• LinkedIn: https://www.linkedin.com/in/garrettlord/
• Email: Garrett@joinhandshake.com
—
Where to find Lenny:
• Newsletter: …
-
How Intercom rose from the ashes by betting everything on AI | Eoghan McCabe (founder and CEO)
21 augustus 2025 · 1 uur 23 min
Eoghan McCabe is the founder and CEO of Intercom, a customer service platform that has successfully pivoted to become an AI-first company with its agent product, Fin. After stepping away from the CEO role in 2020 due to health issues, Eoghan returned to find the company’s growth had stalled. Just one month after his return, ChatGPT launched, and within six weeks, Intercom had a working prototype of what would become Fin. In this conversation, Eoghan shares the brutal reality of transforming a late-stage SaaS business valued at multiple billions into an AI-first company that’s now growing faster than most public software companies. Lees meer
We discuss:
1. Why Eoghan believes most late-stage companies won’t survive the AI transition
2. The “founder mode” transformation that required firing 40% of staff and resulted in 98% employee satisfaction
3. Why having “nothing to lose” is the ultimate advantage in AI transformation (and why comfortable companies will fail)
4. How Intercom transformed from a plateauing SaaS business to an AI-first company growing at 300%+
5. How Intercom’s pricing evolved from “the most hated in SaaS” to a model that charges just $0.99 per resolved ticket
6. The cultural transformation required to compete with AI-native startups
7. How 12 years of therapy and a period of “ego death” shaped Eoghan’s leadership approach
—
Brought to you by:
Great Question—Empower everyone to run great research: https://www.greatquestion.com/lenny
WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs: https://workos.com/lenny
DX—The developer intelligence platform designed by leading researchers: http://getdx.com/lenny
—
Transcript: https://www.lennysnewsletter.com/p/how-intercom-rose-from-the-ashes-eoghan-mccabe
—
My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/170710700/my-biggest-takeaways-from-this-conversation
—
Where to find Eoghan McCabe:
• X: https://x.com/eoghan
• LinkedIn: https://w…
-
Why ChatGPT will be the next big growth channel (and how to capitalize on it) | Brian Balfour (Reforge)
17 augustus 2025 · 1 uur 29 min
Brian Balfour is the founder of Reforge, the former VP of Growth at HubSpot, and a student (and teacher) of product growth. Brian has studied every major platform shift—from Facebook to Apple to Google—and he’s spotted a pattern that’s about to repeat with ChatGPT. Lees meer
In this conversation, you’ll learn:
1. The 4-step cycle every platform follows (and why ChatGPT just entered step 2)
2. Why ChatGPT’s platform launch could be bigger than Facebook’s early platform
3. The exact signals that ChatGPT will launch a third-party platform within six months
4. Why you have six months (not years) to make your platform bet
5. Why companies that don’t integrate with ChatGPT will lose to competitors that do
6. How Zynga grew to $1B by betting on Facebook’s platform early (before it was obvious)
7. Why so few companies are actually doing what they need to be doing right now
—
Brought to you by:
DX—The developer intelligence platform designed by leading researchers: http://getdx.com/lenny
Basecamp—The famously straightforward project management system from 37signals: https://www.basecamp.com/lenny
Miro—A collaborative visual platform where your best work comes to life: https://miro.com/lenny
—
Transcript: https://www.lennysnewsletter.com/p/why-chatgpt-will-be-the-next-big-growth-channel-brian-balfour
—
My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/170294620/my-biggest-takeaways-from-this-conversation
—
Where to find Brian Balfour:
• X: https://twitter.com/bbalfour
• LinkedIn: https://www.linkedin.com/in/bbalfour/
• Website: https://brianbalfour.com/
• Substack: https://blog.brianbalfour.com/
• Podcast: https://www.reforge.com/podcast/unsolicited-feedback
—
Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
In this episode, we cover:
(00:00) Welcome back, Brian!
(04:13) The changing landscape of produc…
-
The one question that saves product careers | Matt LeMay
14 augustus 2025 · 1 uur 32 min
Matt LeMay spent 13 years as a music critic at Pitchfork before becoming one of product management’s most influential voices. He’s consulted with companies from startups to Fortune 500s and authored two essential PM books, including Impact-First Product Teams. After watching countless product teams get laid off despite “doing everything right,” he discovered a harsh truth: most PMs are optimizing for the wrong things. Lees meer
In this conversation, you’ll learn:
1. The one question that predicts if your team will survive the next layoffs (and why most teams can’t answer it)
2. Why following product “best practices” perfectly can actually accelerate your path to unemployment
3. The “low-impact PM death spiral”—how teams accidentally make themselves irrelevant
4. How to push back on executives without saying “no” (the options, plus a recommendation framework)
5. The counterintuitive reason why the happiest PMs are also the most commercially minded
6. The Liz Phair review that made Matt an internet villain for 22 years—and what it taught him about product management
—
Brought to you by:
Enterpret—Transform customer feedback into product growth: https://enterpret.com/lenny
Pragmatic Institute—Industry‑recognized product, marketing, and AI training & certifications: https://pragmaticinstitute.com/lenny
Claude.ai—The AI for problem solvers and enterprise: http://claude.ai/
—
Transcript: https://www.lennysnewsletter.com/p/the-one-question-that-saves-product-careers-matt-lemay
—
My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/168109376/my-biggest-takeaways-from-this-conversation
—
Where to find Matt LeMay:
• Instagram: https://www.instagram.com/mttlmy
• LinkedIn: https://www.linkedin.com/in/mattlemay/
• Website: https://mattlemay.com/
—
Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
In this episode, w…
-
Inside ChatGPT: The fastest-growing product in history | Nick Turley (Head of ChatGPT at OpenAI)
9 augustus 2025 · 1 uur 36 min
Nick Turley is Head of ChatGPT, the fastest-growing product in history, with 700 million weekly active users (10% of the world’s population). He was part of the original hackathon team that shipped ChatGPT in just 10 days, helped it grow from zero to billions in revenue, and leads product for what may be the most consequential product of our time. We recorded this the day before GPT-5 launched. Lees meer
We discuss:
1. The 10-day sprint from deciding to ship ChatGPT to Sam Altman’s tweet (and why it was originally called “Chat with GPT-3.5”)
2. How they ran a willingness-to-pay Van Westendorp survey in their Discord to decide on the $20/month price point that everyone copied
3. The “Is it maximally accelerated?” philosophy that drives OpenAI’s insane shipping velocity
4. Why ChatGPT’s retention curve “smiles”—users leave, then come back months later using it more
5. The accidental decisions that changed history, including not having a waitlist
6. The impact ChatGPT will have on SEO and product growth
7. The counterintuitive reason why shipping unpolished AI features beats waiting for perfection
8. Why ChatGPT intentionally shipped with that “ugly” model-chooser dropdown
9. How TikTok comments became a primary user research channel early on
—
Brought to you by:
Orkes—The enterprise platform for reliable applications and agentic workflows: https://www.orkes.io/
Vanta—Automate compliance. Simplify security: https://vanta.com/lenny
PostHog—How developers build successful products: https://posthog.com/lenny
—
Transcript: https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley
—
My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/170411252/my-biggest-takeaways-from-this-conversation
—
Where to find Nick Turley
• X: https://x.com/nickaturley
• LinkedIn: https://www.linkedin.com/in/nicholasturley/
• Website: https://nickturley.com/
—
Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https…
-
Brian Chesky's secret mentor who died 9 times, started the Burning Man board, and built the world's first midlife wisdom school | Chip Conley (founder of MEA)
3 augustus 2025 · 1 uur 20 min
Chip Conley is the founder of Joie de Vivre hotels, the second-largest boutique hotel brand in the world. At age 52, he joined Airbnb as Head of Global Hospitality and Strategy, reporting to CEO Brian Chesky, who was 21 years younger. He earned the title of Airbnb’s “Modern Elder” by guiding the young founders on leadership and culture while learning Silicon Valley’s tech mindset himself. Today, Chip leads the Modern Elder Academy, the world’s first midlife wisdom school, and is the author of best-selling books like Wisdom@Work and Peak. He champions the idea that age and experience are assets—and that midlife can be a launchpad for renewed purpose and impact. Lees meer
In this conversation, we discuss:
1. The reality of Brian Chesky in “founder mode”—the good, bad, and stressful
2. How Chip went from running 52 boutique hotels to becoming Airbnb’s in-house mentor in his 50s
3. The “mentor and intern” mindset: how to simultaneously teach others and stay curious like a beginner
4. Why AI might actually favor older workers (hint: human wisdom vs. artificial intelligence)
5. His framework for navigating midlife transitions and finding meaning after 40
6. Specific tactics for older professionals to thrive in tech companies
7. Surprising data that midlife is often the happiest time of life—and how to leverage your 40s, 50s, and beyond
8. Chip’s formula for managing anxiety and fear (and how to regain control when worry strikes)
—
Brought to you by:
Great Question—Empower everyone to run great research: https://www.greatquestion.com/lenny
Vanta—Automate compliance. Simplify security: https://vanta.com/lenny
Coda—The all-in-one collaborative workspace: https://coda.io/lenny
—
Transcript: https://www.lennysnewsletter.com/p/chip-conley
—
My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/168435278/my-biggest-takeaways-from-this-conversation
—
Where to find Chip Conley:
• LinkedIn: https://www.linkedin.com/in/chipconleysf/
…
-
He saved OpenAI, invented the “Like” button, and built Google Maps: Bret Taylor on the future of careers, coding, agents, and more
31 juli 2025 · 1 uur 29 min
Bret Taylor’s legendary career includes being CTO of Meta, co-CEO of Salesforce, chairman of the board at OpenAI (yes, during that drama), co-creating both Google Maps and the Like button, and founding three companies. Today he’s the founder and CEO of Sierra, an AI agent company transforming customer service. He’s one of the few people I’ve met who’s been wildly successful at every level—from engineer to C-suite executive to founder—and across almost every discipline, including PM, engineer, CTO, COO, CPO, CEO, and board member. Lees meer
In this conversation, you’ll learn:
1. The brutal product review that nearly ended his Google career—and how that failure led to creating Google Maps
2. The question Sheryl Sandberg taught him to ask every morning (“What’s the most impactful thing I can do today?”) that transformed how he approached every role
3. The three AI market segments that matter
4. Why AI agents will replace SaaS products
5. His framework for knowing whose advice to actually listen to—and how that came in handy during the OpenAI board drama
6. The counterintuitive go-to-market strategy most AI startups get wrong
7. Sierra’s outcome-based pricing model that’s transforming how enterprise software is sold (and why every SaaS company should adopt it)
8. What he’s teaching his kids about AI that every parent should know
—
Brought to you by:
CodeRabbit—Cut code review time and bugs in half. Instantly: https://coderabbit.link/lenny
Basecamp—The famously straightforward project management system from 37signals: https://www.basecamp.com/lenny
Vanta—Automate compliance. Simplify security: https://vanta.com/lenny
—
Transcript: https://www.lennysnewsletter.com/p/he-saved-openai-bret-taylor
—
My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/168905359/my-biggest-takeaways-from-this-conversation
—
Where to find Bret Taylor:
• X: https://x.com/btaylor
• LinkedIn: https://www.linkedin.com/in/brettaylor/
—
Where to fi…
-
Pricing your AI product: Lessons from 400+ companies and 50 unicorns | Madhavan Ramanujam
27 juli 2025 · 1 uur 12 min
Madhavan Ramanujam is the world’s foremost expert on pricing and monetization strategy. As managing partner at Simon-Kucher, he helped over 250 companies, including 30 unicorns, architect their pricing strategies. He’s the author of the definitive book on pricing, Monetizing Innovation. Now he’s back with a sequel, Scaling Innovation, which reveals how to build enduring businesses by dominating both market share and wallet share. He recently left Simon-Kucher to launch his own fund, 49 Palms, focused on helping early-stage AI companies. Lees meer
In this conversation, we discuss:
1. The 2x2 framework that identifies your optimal pricing model
2. Why AI companies can capture 25% to 50% of value created, vs. 10% to 20% for traditional SaaS products
3. Why popular AI coding tools may have already doomed themselves with underpricing
4. The “give-and-get” framework top negotiators use to extract maximum value from every deal
5. The negotiation strategy that helped one founder 4x their deal size overnight
6. How to frame POCs as “business case creation” instead of technical demos (and why this changes everything)
7. Why AI companies must get monetization right from day one—not “figure it out later”
8. How companies like Intercom’s Fin and Sierra pioneered outcome-based pricing (charging $0.99 per AI resolution)
9. The single question that reveals if your pricing is too complex
—
Brought to you by:
Enterpret—Transform customer feedback into product growth: https://enterpret.com/lenny
DX—A platform for measuring and improving developer productivity: https://getdx.com/lenny
Persona—A global leader in digital identity verification: https://withpersona.com/lenny
—
Transcript: https://www.lennysnewsletter.com/p/pricing-and-scaling-your-ai-product-madhavan-ramanujam
—
My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/168109183/my-biggest-takeaways-from-this-conversation
—
Where to find Madhavan Ramanujam:
• X: https://x.com/m…
-
Anthropic co-founder on quitting OpenAI, AGI predictions, $100M talent wars, 20% unemployment, and the nightmare scenarios keeping him up at night | Ben Mann
20 juli 2025 · 1 uur 15 min
Benjamin Mann is a co-founder of Anthropic, an AI startup dedicated to building aligned, safety-first AI systems. Prior to Anthropic, Ben was one of the architects of GPT-3 at OpenAI. He left OpenAI driven by the mission to ensure that AI benefits humanity. In this episode, Ben opens up about the accelerating progress in AI and the urgent need to steer it responsibly. Lees meer
In this conversation, we discuss:
1. The inside story of leaving OpenAI with the entire safety team to start Anthropic
2. How Meta’s $100M offers reveal the true market price of top AI talent
3. Why AI progress is still accelerating (not plateauing), and how most people misjudge the exponential
4. Ben’s “economic Turing test” for knowing when we’ve achieved AGI—and why it’s likely coming by 2027-2028
5. Why he believes 20% unemployment is inevitable
6. The AI nightmare scenarios that concern him most—and how he believes we can still avoid them
7. How focusing on AI safety created Claude’s beloved personality
8. What three skills he’s teaching his kids instead of traditional academics
—
Brought to you by:
Sauce—Turn customer pain into product revenue: https://sauce.app/lenny
LucidLink—Real-time cloud storage for teams: https://www.lucidlink.com/lenny
Fin—The #1 AI agent for customer service: https://fin.ai/lenny
—
Transcript: https://www.lennysnewsletter.com/p/anthropic-co-founder-benjamin-mann
—
My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/168107911/my-biggest-takeaways-from-this-conversation
—
Where to find Ben Mann:
• X: https://x.com/8enmann
• LinkedIn: https://www.linkedin.com/in/benjamin-mann/
• Website: https://benjmann.net/
—
Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
In this episode, we cover:
(00:00) Introduction to Benjamin
(04:43) The AI talent war
(06:28) AI progress and scaling laws
(10:50) Defi…
-
The AI-native startup: 5 products, 7-figure revenue, 100% AI-written code | Dan Shipper (co-founder/CEO of Every)
17 juli 2025 · 1 uur 35 min
Dan Shipper is the co-founder and CEO of Every. With just 15 people, Every publishes a daily AI newsletter, ships multiple AI products, and operates a million-dollar-a-year consulting arm—all while their engineers write virtually zero code. It’s the most radical example of AI-first operations, and Dan is a prolific writer who has become a leading voice on how AI is transforming the way we build and work. Lees meer
Learn:
1. Why Dan thinks AI won’t steal jobs en masse—and may actually reshore many jobs to the U.S.
2. The most underrated AI tool for non-programmers
3. An inside look at Every’s AI-first workflow
4. Why every company needs an “AI operations lead”
5. How Dan’s team uses an arsenal of AI agents (Claude, Codex, “Friday,” “Charlie”) in parallel, treating each AI like a specialist with unique strengths
6. Why generalists will thrive in an AI-first world, as rigid job titles blur and everyone becomes a “manager” of AI tools
7. Dan’s playbook for making any company AI-first—from the CEO setting the example, to hosting internal prompt-sharing sessions, to upskilling teams on AI tools
—
Brought to you by:
CodeRabbit—Cut code review time and bugs in half. Instantly: https://coderabbit.link/lenny
DX—A platform for measuring and improving developer productivity: https://getdx.com/lenny
PostHog—How developers build successful products: https://posthog.com/lenny
—
Transcript: https://www.lennysnewsletter.com/p/inside-every-dan-shipper
—
My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/167681269/my-biggest-takeaways-from-this-conversation
—
Where to find Dan Shipper:
• X: https://x.com/danshipper
• LinkedIn: https://www.linkedin.com/in/danshipper/
• Podcast: https://every.to/podcast
—
Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
In this episode, we cover:
(00:00) Welcome and introduction
(04:…
-
Rapidly test and validate any startup idea with the 2-day Foundation Sprint (from the creators of the Design Sprint) | Jake Knapp & John Zeratsky (Character Capital)
13 juli 2025 · 1 uur 42 min
Jake Knapp and John Zeratsky are the co-creators of the Design Sprint (the famous five-day product innovation process) and authors of the bestselling book Sprint. After decades of working with over 300 startups in the earliest stages, they discovered that most startups fail not because they can’t build, but because they build the wrong thing. The very beginning of a startup is your highest-leverage moment, and most teams waste months or years by skipping a few critical early questions. Jake and John developed the Foundation Sprint to help startups validate ideas and compress months of work into just two days. Lees meer
What you’ll learn:
1. The step-by-step Foundation Sprint process that compresses three or four months of validation into two days—including templates you can use immediately
2. Why differentiation is the #1 predictor of startup success (with the 2x2 framework that you can use with your team)
3. The three fundamental questions every founder should answer before writing a line of code
4. The “note and vote” technique that eliminates groupthink and gets honest answers from your colleagues
5. The seven “magic lenses” for choosing between multiple product ideas
6. The biggest mistake engineers make when building with AI tools
7. The paradox of speed: why “building nothing first” can get you to product-market fit faster
—
Brought to you by:
Brex—The banking solution for startups: https://www.brex.com/product/business-account?ref_code=bmk_dp_brand1H25_ln_new_fs
Paragon—Ship every SaaS integration your customers want: https://www.useparagon.com/lenny
Coda—The all-in-one collaborative workspace: https://coda.io/lenny
—
Transcript: https://www.lennysnewsletter.com/p/the-foundation-sprint-jake-knapp-and-john-zeratsky
—
My biggest takeaways (for paid newsletter subscribers):
https://www.lennysnewsletter.com/i/167485876/my-biggest-takeaways-from-this-conversation
—
Where to find Jake Knapp:
• X: https://twitter.com/jakek
• LinkedIn: https://www.linked…
-
Solo founder, $80M exit, 6 months: The Base44 bootstrapped startup success story | Maor Shlomo
6 juli 2025 · 1 uur 32 min
Maor Shlomo is the founder of Base44, an AI-powered app builder that he bootstrapped to an over $80 million acquisition by Wix in just six months. As a solo founder (with severe ADHD), he hit $1 million ARR just three weeks after launch and grew the product to more than 400,000 users, all while navigating two wars in Israel and never raising a dollar of outside funding. Lees meer
What you’ll learn:
1. The growth playbook that took Base44 from three friends to 400,000 users without spending any money on marketing
2. How he hasn’t written a single line of front-end code in three months—and how to structure your code repository to make it easier for AI to write your code
3. His AI productivity stack that allowed him to compete against heavily funded competitors
4. Why being a solo founder in AI might be the ultimate advantage (and the wedding story that almost killed the business)
5. The story of signing the $80M acquisition deal while war broke out with Iran
6. How to identify when to sell vs. stay independent (and why Maor chose acquisition despite being highly profitable)
7. The counterintuitive product decision that tripled activation by removing a “helpful” feature
8. How building in public on LinkedIn drove more growth than any paid channel
—
Brought to you by:
Sauce—Turn customer pain into product revenue: https://sauce.app/lenny
Dscout—The UX platform to capture insights at every stage: from ideation to production: https://www.dscout.com/
Contentsquare—Create better digital experiences: https://contentsquare.com/lenny/
—
Transcript: https://www.lennysnewsletter.com/p/the-base44-bootstrapped-startup-success-story-maor-shlomo
—
My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/167384119/my-biggest-takeaways-from-this-conversation
—
Where to find Maor Shlomo:
• X: https://x.com/ms_base44
• LinkedIn: https://www.linkedin.com/in/maor-shlomo-1088b4144/
—
Where to find Lenny:
• Newsletter: https://www.lennysnews…
-
I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny)
3 juli 2025 · 1 uur 28 min
Andrew Wilkinson is the co‑founder of Tiny, a holding company that quietly owns more than three dozen profitable internet and consumer brands, including Dribbble and the AeroPress coffee maker. Starting as a teenage barista and web designer, he’s created a portfolio approaching $300 million in yearly sales (and he was personally worth over $1 billion at one point)—all without ever raising venture capital. Lees meer
In this conversation, you’ll learn:
1. The “fish where the fish are” framework for spotting high‑margin niches no one else notices
2. The exact agent stack (Lindy, Replit, Limitless, and more) that supercharges Andrew’s day-to-day productivity (and has replaced his assistant)
3. How Andrew evaluates companies in less than 15 minutes using Buffett‑style moats and “lazy leadership”
4. Telltale signs you should shut down (or never start) that startup idea
5. His journey from crippling anxiety to clarity through SSRIs and ADHD medication
6. His prediction that most knowledge work will be automated—and the skills to teach your kids now
—
Brought to you by:
Sauce—Turn customer pain into product revenue
Enterpret—Transform customer feedback into product growth
Miro—A collaborative visual platform where your best work comes to life
—
Where to find Andrew Wilkinson:
• X: https://x.com/awilkinson
• LinkedIn: https://www.linkedin.com/in/awilkinson/
—
Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
In this episode, we cover:
(00:00) Introduction to Andrew Wilkinson
(04:07) Finding the right business idea
(07:18) Avoiding common business pitfalls
(11:58) Finding your unfair advantage
(17:08) Fish where the fish are
(20:08) Why boring is good
(25:30) Bootstrapping vs. venture capital
(31:20) Lessons from acquiring and managing businesses
(36:47) Avoiding people problems
(42:39) Leveraging AI in business and life
(49:30) The Limitless …
-
Naming expert shares the process behind creating billion-dollar brand names like Azure, Vercel, Windsurf, Sonos, Blackberry, and Impossible Burger | David Placek (Lexicon Branding)
29 juni 2025 · 1 uur 23 min
David Placek is the founder of Lexicon Branding, a company that focuses exclusively on the development of brand names for competitive advantage. Lexicon is behind iconic names such as Sonos, Microsoft’s Azure, Windsurf, Vercel, Impossible Foods, BlackBerry, Intel’s Pentium, Apple’s PowerBook, and Swiffer. Over 40 years, David’s team has named nearly 4,000 brands and companies, employing over 250 linguists and pioneering naming innovation. Lees meer
What you’ll learn:
1. The three-step process that generated names like Windsurf and Vercel
2. How a name can give you the edge that no marketing budget can buy
3. Why you won’t “know it when you see it”
4. Why Microsoft called Azure “a dumb name” before it became their billion-dollar cloud platform
5. Why polarizing opinions are the strongest signal that you’ve found the right name
6. How every letter of the alphabet creates a specific psychological vibration
7. The diamond framework: a 4-step process any founder can use to find their perfect name
8. Why domain names don’t matter anymore in the age of AI
—
Brought to you by:
WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs
Stripe—Helping companies of all sizes grow revenue
OneSchema—Import CSV data 10x faster
—
Where to find David Placek:
• LinkedIn: https://www.linkedin.com/in/david-placek-05a82/
• Website: https://www.lexiconbranding.com
—
Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
In this episode, we cover:
(00:00) Introduction to David and Lexicon Branding
(04:44) The story of Sonos
(09:27) The psychology of naming
(11:33) The initial resistance to Microsoft's Azure
(14:35) The importance of a great brand name
(18:11) The three steps of naming: create, invent, implement
(28:23) Qualities of great brand name creators
(31:24) How long the naming process takes
(32:12) The Windsurf case study
(36:10) Naming i…
-
From ChatGPT to Instagram to Uber: The quiet architect behind the world’s most popular products | Peter Deng
22 juni 2025 · 1 uur 55 min
Peter Deng has led product teams at OpenAI, Instagram, Uber, Facebook, Airtable, and Oculus and helped build products used by billions—including Facebook’s News Feed, the standalone Messenger app, Instagram filters, Uber Reserve, ChatGPT, and more. Currently he’s investing in early-stage founders at Felicis. In this episode, Peter dives into his most valuable lessons from building and scaling some of tech’s most iconic products and companies. Lees meer
What you’ll learn:
1. Peter’s one‑sentence test for hiring superstars
2. Why your product (probably) doesn’t matter
3. Why you don’t need a tech breakthrough to build a huge business
4. The five PM archetypes, and how to build a team of Avengers
5. Counterintuitive lessons on growing products from 0 to 1, and 1 to 100
6. The importance of data flywheels and workflows
—
Brought to you by:
Paragon—Ship every SaaS integration your customers want
Pragmatic Institute—Industry‑recognized product, marketing, and AI training and certifications
Contentsquare—Create better digital experiences
—
Where to find Peter Deng:
• X: https://x.com/pxd
• LinkedIn: https://www.linkedin.com/in/peterxdeng/
—
In this episode, we cover:
(00:00) Introduction to Peter Deng
(05:41) AI and AGI insights
(11:35) The future of education with AI
(16:53) The power of language in leadership
(21:01) Building iconic products
(36:44) Scaling from zero to 100
(41:56) Balancing short- and long-term goals
(47:12) Creating a healthy tension in teams
(50:02) The five archetypes of product managers
(55:39) Primary and secondary archetypes
(58:47) Hiring for growth mindset and autonomy
(01:15:52) Effective management and communication strategies
(01:19:23) Presentation advice and self-advocacy
(01:25:50) Balancing craft and practicality in product management
(01:30:40) The importance of empathy in design thinking
(01:35:45) Career decisions and learning opportunities
(01:42:05) Lessons from product failures
(01:45:42) Lightning round a…
-
AI prompt engineering in 2025: What works and what doesn’t | Sander Schulhoff (Learn Prompting, HackAPrompt)
19 juni 2025 · 1 uur 38 min
Sander Schulhoff is the OG prompt engineer. He created the very first prompt engineering guide on the internet (two months before ChatGPT’s release) and recently wrote the most comprehensive study of prompt engineering ever conducted (co-authored with OpenAI, Microsoft, Google, Princeton, and Stanford), analyzing over 1,500 academic papers and covering more than 200 prompting techniques. He also partners with OpenAI to run what was the first and is the largest AI red teaming competition, HackAPrompt, which helps discover the most state-of-the-art prompt injection techniques (i.e. ways to get LLMS to do things it shouldn’t). Sander teaches AI red teaming on Maven, advises AI companies on security, and has educated millions of people on the most state-of-the-art prompt engineering techniques. Lees meer
In this episode, you’ll learn:
1. The 5 most effective prompt engineering techniques
2. Why “role prompting” and threatening the AI no longer works—and what to do instead
3. The two types of prompt engineering: conversational and product/system prompts
4. A primer on prompt injection and AI red teaming—including real jailbreak tactics that are still fooling top models
5. Why AI agents and robots will be the next major security threat
6. How to get started in AI red teaming and prompt engineering
7. Practical defense to put in place for your AI products
—
Brought to you by:
Eppo—Run reliable, impactful experiments
Stripe—Helping companies of all sizes grow revenue
Vanta—Automate compliance. Simplify security
—
Where to find Sander Schulhoff:
• X: https://x.com/sanderschulhoff
• LinkedIn: https://www.linkedin.com/in/sander-schulhoff/
• Website: https://sanderschulhoff.com/
• AI Red Teaming and AI Security Masterclass on Maven: https://bit.ly/44lLSbC
• Free Lightning Lesson “How to Secure Your AI System” on 6/24: https://bit.ly/4ld9vZL
—
Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https:/…
-
How to build a team that can “take a punch”: A playbook for building resilient, high-performing teams | Hilary Gridley (Head of Core Product, Whoop)
15 juni 2025 · 1 uur 55 min
Hilary Gridley is the Head of Core Product at WHOOP and a passionate thought leader in leveraging AI to elevate product teams and management practices. With extensive experience tackling challenging problems in regulated industries and high-stakes environments, Hilary emphasizes the importance of building resilience and adaptability within teams. Previously, she was a senior director of product at Big Health and a senior product marketing manager at Dropbox. Lees meer
In this episode, you’ll learn:
• How to teach your team to be able to “take a punch”
• Specific tactics to counter negative perceptions and reframe setbacks productively
• Powerful behavioral strategies to form positive habits
• Practical approaches for creating space in your workday to encourage creativity and deep thinking
• The underestimated potential of AI in accelerating your personal and professional growth
• Why you’re not the protagonist at your company (and why that’s liberating)
• How WHOOP uses reward loops to drive real behavior change
—
Brought to you by:
WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs
Persona—A global leader in digital identity verification
Attio—The powerful, flexible CRM for fast-growing startups
—
Where to find Hilary Gridley:
• X: https://x.com/yourgirlhils
• LinkedIn: https://www.linkedin.com/in/hilarygridley/
• Newsletter: https://hils.substack.com/
• Maven course: https://maven.com/hilary-gridley/ai-powered-people-management
—
Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
In this episode, we cover:
(00:00) Hilary’s background
(04:31) Teaching teams to handle criticism and setbacks
(17:57) Behavioral activation and mental health in the workplace
(22:59) The importance of putting yourself out there
(27:51) Transparency and communication in leadership
(38:10) How to respectfully disagree with your manager
(4…
-
35 years of product design wisdom from Apple, Disney, Pinterest, and beyond | Bob Baxley
12 juni 2025 · 1 uur 42 min
Bob Baxley is a design leader who has shaped products used by billions at Apple, Pinterest, Yahoo, and ThoughtSpot. During his eight years at Apple, he led design for the online store and the App Store, and witnessed the iPhone’s transformative launch while working under Steve Jobs. A student of history turned software craftsman, Bob discovered his calling after exploring photography, filmmaking, and music, ultimately recognizing software as the most powerful creative medium of our time. Bob champions the moral obligation designers have to reduce frustration in people’s daily digital interactions. Lees meer
What you’ll learn:
• Why design should report to engineering, not product
• The “Beatles principle”—why the best products come from teams of 4 to 6, not 40 to 60
• How to create design tenets vs. principles (with real examples)
• The counterintuitive reason to delay drawing or prototyping as long as possible
• Why software is fundamentally a medium, like film or music (not just a tool)
• Why Bob “bounced off the culture” at Pinterest, and lessons from failure
• The lunar landing story that teaches us about championing radical ideas
• How to evaluate if a company truly values design before joining
• The moral obligation of software makers to build great products
—
This entire episode is brought to you by Stripe—helping companies of all sizes grow revenue.
—
Where to find Bob Baxley:
• Instagram: https://www.instagram.com/baxley/
• LinkedIn: https://www.linkedin.com/in/bbaxley/
• Website: http://www.bobbaxley.com/
—
Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
In this episode, we cover:
(00:00) Introduction to Bob Baxley
(03:52) Apple's lasting culture
(06:15) Navigating unique company cultures
(13:19) Finding a company that truly values your role
(15:46) What is design?
(17:17) How to help founders understand the value of design
…
-
How Mercado Libre built Latin America's most valuable company: 18k engineers, 30k deploys a day, and their own fleet of planes | Sebastian Barrios
8 juni 2025 · 1 uur 19 min
Sebastian Barrios was the longtime head of product and engineering at Mercado Libre, the largest company in Latin America—valued at over $100 billion and home to more than 100,000 employees. There, he led a team of more than 18,000 engineers across 18 countries and oversaw an astonishing 30,000 code deployments a day. Before Mercado Libre, he founded multiple startups, including a ridesharing company that competed directly with Uber in Latin America. And at just 17, he got a personal phone call from Steve Jobs asking him to take his app off the App Store. Today, Sebastian is the SVP of Engineering at Roblox. Lees meer
What you’ll learn:
• Why Mercado Libre operates with 95% fewer PMs than typical tech companies (and how it actually works)
• How to maintain product quality with 30,000 daily deployments and distributed ownership
• The weekly email system Sebastian uses to maintain alignment with leadership
• How to build a culture of radical candor and direct feedback in a traditionally hierarchical region
• The counterintuitive approach to product reviews that keeps 18,000 engineers aligned
• How to evaluate hype cycles (crypto, AI) pragmatically while staying innovative
—
Brought to you by:
Merge—A single API to add hundreds of integrations into your app
Vanta—Automate compliance. Simplify security
LinkedIn Ads—Reach professionals and drive results for your business
—
Where to find Sebastian Barrios:
• LinkedIn: https://www.linkedin.com/in/zebas/
—
Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
In this episode, we cover:
(00:00) Introduction to Sebastian Barrios and Mercado Libre
(05:03) Mercado Libre’s scale and unique ways of operating
(14:48) AI’s impact on operations
(19:19) Empowering teams and reducing fear of failure
(34:20) The importance of radical candor
(38:26) Weekly updates
(41:03) Avoiding hype cycles
(44:24) When Steve …
-
Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram)
5 juni 2025 · 1 uur 6 min
Mike Krieger is the chief product officer of Anthropic and the co-founder of Instagram. After leaving Meta, he co-founded Artifact, an AI-powered news app that I absolutely loved, and joined Anthropic to lead product in 2024. Lees meer
In this episode, you'll learn:
• How Anthropic uses AI to write 90-95% of code for some products and the surprising new bottlenecks this creates
• Why embedding product managers with AI researchers yields 10x the impact of traditional product development
• The three areas where product teams can still add massive value as AI gets smarter
• How Anthropic plans to compete with OpenAI long-term
• How to use Claude as your product strategy partner (with specific prompting techniques)
• Why Mike shut down Artifact despite loving the product, and what founders can learn from it
• Where AI startups should build to avoid getting killed by OpenAI, Anthropic, and Google
• Why MCP (Model Context Protocol) might reshape how all software works
• The counterintuitive product metrics that matter for AI
• How to evaluate whether your company is maximizing AI’s potential or just scratching the surface
—
Brought to you by:
Productboard—Make products that matter
Stripe—Helping companies of all sizes grow revenue
OneSchema—Import CSV data 10x faster
—
Where to find Mike Krieger:
• X: https://x.com/mikeyk
• LinkedIn: https://www.linkedin.com/in/mikekrieger/
—
Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
In this episode, we cover:
(00:00) Introduction to Mike Krieger
(04:20) What Mike has changed his mind about regarding AI capabilities
(07:38) How to avoid scary AI scenarios
(08:55) Skills kids will need in an AI world
(11:53) How product development changes when 90% of code is written by AI
(17:07) Claude helping with product strategy
(21:16) A new way of working
(23:55) The future value of product teams in an AI wo…
-
Why Uber’s CPO delivers food on weekends | Sachin Kansal
1 juni 2025 · 1 uur 22 min
Sachin Kansal is chief product officer at Uber, where he oversees the Rider, Driver, Delivery, Grocery, and New Verticals product lines used for 33 million daily trips worldwide. He’s been in product for over 25 years (at Google, Palm, Flywheel, and now Uber). He is known for his “extreme dogfooding” ethos—personally completing almost a thousand Uber driving and delivery trips to sharpen his product insight and user empathy—and his “ship, ship, ship” mantra, which drives rapid iteration across Uber’s global teams. Lees meer
What you will learn:
1. Dogfooding at scale
2. “Ship, ship, ship” as a cultural mantra
3. Obsession with inputs over outputs
4. Uber’s hybrid marketplace vision for autonomy
5. How Uber changed its culture to focus on profitability
6. What to do when data says “no” but your gut says “yes”
7. Career advice: maximize cycles
8. AI as a research assistant, not an oracle
9. Uber rider etiquette tips
—
Brought to you by:
• Paragon—Ship every SaaS integration your customers want
• Stripe—Financial infrastructure to grow your revenue
• Coda—The all-in-one collaborative workspace
—
Where to find Sachin Kansal:
• LinkedIn: https://www.linkedin.com/in/sachinkansal/
—
Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
In this episode, we cover:
(00:00) Sachin’s background
(05:00) Dogfooding in practice
(11:24) Empathy and understanding drivers
(20:18) Balancing metrics and user experience
(22:04) Operationalizing dogfooding
(24:26) Challenges and solutions in dogfooding
(29:49) The motto: “ship, ship, ship”
(36:37) Product announcements and live demos
(40:49) Career advice for product managers
(43:51) The evolution of product management with AI
(46:55) Collaboration between engineers and product managers
(49:36) Uber’s vision for self-driving cars
(55:59) Uber’s path to profitability
(01:01:58) Balancing data and gut deci…