Strategy
Featured Quotes
“Lenny, you're the legend around here, not me.”
April Dunford on product positioning, segmentation, and optimizing your sales process
“You're the guy. You're like Madonna. You're just a one-name guy now. You're Lenny, the Lenny.”
April Dunford on product positioning, segmentation, and optimizing your sales process
“That sounds amazing. That's a high bar, but I will try to live up to your expectations.”
How marketplaces win: Liquidity, growth levers, quality, and more | Benjamin Lauzier (Lyft, Thumbtack, Reforge)
“WorkOS also recently launched AuthKit, a complete authentication and user management service.”
LENNY RACHITSKY
Kunal Shah on winning in India, second-order thinking, the philosophy of startups, and more
“That sounds awesome, and thank you so much for having me, Lenny. I mean, it's a true pleasure to be here with you.”
"Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel
“It's essentially a modern alternative to Auth0, but with better pricing and more flexible APIs.”
LENNY RACHITSKY
Kunal Shah on winning in India, second-order thinking, the philosophy of startups, and more
Episodes (162)
Jenny Wen
Jenny Wen
Dr. Becky Kennedy
A child psychologist’s guide to working with difficult adults | Dr. Becky Kennedy
Jason Cohen
5 questions to ask when your product stops growing | Jason Cohen (2x unicorn founder)
Matt MacInnis
10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling)
Elena Verna 4.0
Elena Verna 4.0
Jeanne Grosser
What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google)
Rachel Lockett
A guide to difficult conversations, building high-trust teams, and designing a life you love | Rachel Lockett
Dr. Fei Fei Li
The Godmother of AI on jobs, robots & why world models are next | Dr. Fei-Fei Li
Grant Lee
“Dumbest idea I’ve heard” to $100M ARR: Inside the rise of Gamma | Grant Lee (CEO)
Jen Abel
"Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel
People (161)
Ada Chen Rekhi
Co-Founder & COO
Adam Fishman
Executive in Residence / Advisor
Adam Grenier
VP of Growth
Adriel Frederick
VP of Product, Reddit X
Alex Komoroske
Co-Founder & CEO
Alisa Cohn
Executive Coach & Author
Andrew Wilkinson
Co-Founder & Executive Chairman
Andy Raskin
Strategic Narrative Consultant
Anneka Gupta
Chief Product Officer
Annie Pearl
CVP & GM, Azure Experiences
Anuj Rathi
Founder (Stealth)
Aparna Chennapragada
Chief Product Officer, Experiences & Devices
Newsletters (201)
How to build your PM second brain with ChatGPT
Use AI to amplify your craft, not replace it
How to spot a top 1% startup early
Three key lessons from people who picked multiple iconic companies before they were obvious
Ecosystem is the next big growth channel
How to stand out in a noisy landscape by leveraging partners who already have access and trust with your target audience
A builder’s guide to living a long and healthy life
For something a little different
How to find the perfect name
A step-by-step playbook for naming in a noisy and AI-driven product landscape
Essential reading for product builders—part 2
10 more timeless essays you probably haven’t read but should
Build your personal AI copilot
A guide to using AI as a long-term thinking partner (including prompts to get you started)
Essential reading for product builders—part 1
7 timeless essays you likely haven’t read but should
The definitive guide to mastering analytical thinking interviews
A step-by-step playbook to help you ace your PM interviews
Taking the week off
Back next week!