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.

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/madhavansf

• LinkedIn: https://www.linkedin.com/in/madhavansf/

• Promo email for Scaling Innovation: [email protected] — If you’re purchasing more than five copies, send a screenshot of your receipt to enter Madhavan’s exclusive bundle raffle.

—

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 Madhavan and his work

(04:30) The core thesis of Scaling Innovation

(09:20) Common traps founders fall into

(12:06) Beautifully simple pricing

(15:00) Mastering negotiations

(26:51) Other strategies for effective pricing and monetization

(27:35) How AI pricing is different

(31:33) Handling POCs

(36:25) The importance of mastering monetization

(38:58) Choosing the right AI pricing model

(43:13) Current trends in AI pricing

(44:48) Strategizing for outcome-based models

(50:23) Packaging strategies for scaling

(51:37) Adapting pricing strategies over time

(53:40) Key axioms for pricing success

(58:00) Takeaways for founders

(01:01:33) Lightning round and final thoughts

—

Referenced:

• The art and science of pricing | Madhavan Ramanujam (Monetizing Innovation, Simon-Kucher): https://www.lennysnewsletter.com/p/the-art-and-science-of-pricing-madhavan

• Cursor: https://www.cursor.com/

• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell

• Sierra Finn: http://www.sierrafinn.com/

• Chargeflow: https://www.chargeflow.io/

• GitHub: https://github.com/

• Intercom: https://www.intercom.com/

• Warren Buffett’s quote: https://www.goodreads.com/quotes/11478913-if-you-ve-got-the-power-to-raise-prices-without-losing

• Sierra: https://sierra.ai/

• Clay Bavor on LinkedIn: https://www.linkedin.com/in/claybavor/

• Mission: Impossible—The Final Reckoning: https://www.imdb.com/title/tt9603208/

• Delphi: https://www.delphi.ai/

• Dara Ladjevardian on LinkedIn: https://www.linkedin.com/in/dara-ladjevardian/

• Sam Spelsberg on LinkedIn: https://www.linkedin.com/in/samuel-spelsberg/

• Lennybot: https://www.lennybot.com/

• Granola: https://www.granola.ai/

• Simon-Kucher: https://www.simon-kucher.com/

• Josh Bloom on LinkedIn: https://www.linkedin.com/in/joshuabloompricingconsulting/

—

Recommended books:

• Monetizing Innovation: How Smart Companies Design the Product Around the Price: https://www.amazon.com/Monetizing-Innovation-Companies-Design-Product/dp/1119240867

• Scaling Innovation: How Smart Companies Architect Profitable Growth: https://www.amazon.com/dp/1119633060

• Business Model Generation: A Handbook for Visionaries, Game Changers, and Challengers: https://www.amazon.com/Business-Model-Generation-Visionaries-Challengers/dp/0470876417

• Thinking Fast and Slow: https://www.amazon.com/Thinking-Fast-Slow-Daniel-Kahneman/dp/0374533555/

• Contagious: Why Things Catch On: https://www.amazon.com/Contagious-Things-Catch-Jonah-Berger/dp/1451686587/

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

Lenny may be an investor in the companies discussed.

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.

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) Defining AGI and the economic Turing test

(12:26) The impact of AI on jobs

(17:45) Preparing for an AI future

(24:05) Founding Anthropic

(27:06) Balancing AI safety and progress

(29:10) Constitutional AI and model alignment

(34:21) The importance of AI safety

(43:40) The risks of autonomous agents

(45:40) Forecasting superintelligence

(48:36) How hard is it to align AI?

(53:19) Reinforcement learning from AI feedback (RLAIF)

(57:03) AI's biggest bottlenecks

(01:00:11) Personal reflections on responsibilities

(01:02:36) Anthropic’s growth and innovations

(01:07:48) Lightning round and final thoughts

—

Referenced:

• Dario Amodei on LinkedIn: https://www.linkedin.com/in/dario-amodei-3934934/

• Anthropic CEO: AI Could Wipe Out 50% of Entry-Level White Collar Jobs: https://www.marketingaiinstitute.com/blog/dario-amodei-ai-entry-level-jobs

• Alexa+: https://www.amazon.com/dp/B0DCCNHWV5

• Azure: https://azure.microsoft.com/

• Sam Altman on X: https://x.com/sama

• Opus 3: https://www.anthropic.com/news/claude-3-family

• Claude’s Constitution: https://www.anthropic.com/news/claudes-constitution

• Greg Brockman on X: https://x.com/gdb

• Anthropic’s Responsible Scaling Policy: https://www.anthropic.com/news/anthropics-responsible-scaling-policy

• Agentic Misalignment: How LLMs could be insider threats: https://www.anthropic.com/research/agentic-misalignment

• Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next

• AI prompt engineering in 2025: What works and what doesn’t | Sander Schulhoff (Learn Prompting, HackAPrompt): https://www.lennysnewsletter.com/p/ai-prompt-engineering-in-2025-sander-schulhoff

• Unitree: https://www.unitree.com/

• Arthur C. Clarke: https://en.wikipedia.org/wiki/Arthur_C._Clarke

• How Reinforcement Learning from AI Feedback Works: https://www.assemblyai.com/blog/how-reinforcement-learning-from-ai-feedback-works

• RLHF: https://en.wikipedia.org/wiki/Reinforcement_learning_from_human_feedback

• Jared Kaplan on LinkedIn: https://www.linkedin.com/in/jared-kaplan-645843213/

• Moore’s law: https://en.wikipedia.org/wiki/Moore%27s_law

• Machine Intelligence Research Institute: https://intelligence.org/

• Raph Lee on LinkedIn: https://www.linkedin.com/in/raphaeltlee/

• “The Last Question”: https://en.wikipedia.org/wiki/The_Last_Question

• Beth Barnes on LinkedIn: https://www.linkedin.com/in/elizabethmbarnes/

• “The Last Question”: https://en.wikipedia.org/wiki/The_Last_Question

• Good Strategy, Bad Strategy | Richard Rumelt: https://www.lennysnewsletter.com/p/good-strategy-bad-strategy-richard

• Pantheon on Netflix: https://www.netflix.com/title/81937398

• Ted Lasso on AppleTV+: https://tv.apple.com/us/show/ted-lasso/umc.cmc.vtoh0mn0xn7t3c643xqonfzy

• Kurzgesagt—In a Nutshell: https://www.youtube.com/channel/UCsXVk37bltHxD1rDPwtNM8Q

• 5 tips to poop like a champion: https://8enmann.medium.com/5-tips-to-poop-like-a-champion-3292481a9651

—

Recommended books:

• Superintelligence: Paths, Dangers, Strategies: https://www.amazon.com/Superintelligence-Dangers-Strategies-Nick-Bostrom/dp/0198739834

• The Hacker and the State: Cyber Attacks and the New Normal of Geopolitics: https://www.amazon.com/Hacker-State-Attacks-Normal-Geopolitics/dp/0674987551

• Replacing Guilt: Minding Our Way: https://www.amazon.com/Replacing-Guilt-Minding-Our-Way/dp/B086FTSB3Q

• Good Strategy/Bad Strategy: The Difference and Why It Matters: https://www.amazon.com/Good-Strategy-Bad-Difference-Matters/dp/0307886239

• The Alignment Problem: Machine Learning and Human Values: https://www.amazon.com/Alignment-Problem-Machine-Learning-Values/dp/0393635821

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

Lenny may be an investor in the companies discussed.

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.

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

(04:04) Hot takes on AI and job reshoring

(07:06) The power of Claude Code for non-coders

(14:35) The future of AI in business operations

(18:45) AI’s role in enhancing human skills

(22:26) The evolution of AI tools and their applications

(25:40) Building an AI-first company

(29:50) Innovative AI operations and team dynamics

(35:35) Dan's AI stack

(41:26) Compounding engineering

(48:29) The impact of AI on learning and development

(50:10) Accelerating career growth with AI

(51:36) Revolutionizing code review and workflow

(53:07) The importance of coding knowledge

(57:26) Building AI-driven products

(01:02:01) Innovative fundraising strategies

(01:08:45) Consulting and AI adoption in companies

(01:17:01) The allocation economy and future skills

(01:20:12) The value of generalists in the AI age

(01:24:07) Lightning round and final thoughts

—

Referenced:

• Claude Code: https://www.anthropic.com/claude-code

• Gemini CLI: https://blog.google/technology/developers/introducing-gemini-cli-open-source-ai-agent/

• Microsoft Copilot: https://copilot.microsoft.com/

• Cursor: https://www.cursor.com/

• Base44: https://base44.com/

• Solo founder, $80M exit, 6 months: The Base44 bootstrapped startup success story | Maor Shlomo: https://www.lennysnewsletter.com/p/the-base44-bootstrapped-startup-success-story-maor-shlomo

• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell

• Plato’s Argument Against Writing: https://fs.blog/an-old-argument-against-writing/

• From ChatGPT to Instagram to Uber: The quiet architect behind the world’s most popular products | Peter Deng: https://www.lennysnewsletter.com/p/the-quiet-architect-peter-deng

• Granola: https://www.granola.ai/

• Tobi Lutke’s post on X about context engineering: https://x.com/tobi/status/1935533422589399127

• Tobi Lütke’s leadership playbook: Playing infinite games, operating from first principles, and maximizing human potential (founder and CEO of Shopify): https://www.lennysnewsletter.com/p/tobi-lutkes-leadership-playbook

• Every: https://every.to/

• Cora: https://www.cora.computer/

• Sparkle: https://makeitsparkle.co/

• Spiral: https://spiral.computer/

• Lex: https://lex.page/

• Nathan Baschez on LinkedIn: https://www.linkedin.com/in/nbashaw/

• Kate Lee on LinkedIn: https://www.linkedin.com/in/kate-lee-506768/

• Katie Parrott on LinkedIn: https://www.linkedin.com/in/katieparrott/

• Animalz: https://www.animalz.co/

• Rachel Woods on X: https://x.com/rachel_l_woods

• Nityesh Agarwal on LinkedIn: https://www.linkedin.com/in/nityeshaga

• Claude Opus 4: https://www.anthropic.com/claude/opus

• Codex: https://openai.com/index/introducing-codex/

• Superwhisper: https://superwhisper.com/

• Wispr Flow: https://wisprflow.ai/

• Notion: https://www.notion.com/

• Kieran Klaassen on LinkedIn: https://www.linkedin.com/in/kieran-klaassen/

• Friday: https://www.friday.run/

• Charlie: https://www.gocharlie.ai/product/ai-agents/

• Avengers: https://en.wikipedia.org/wiki/Avengers_(Marvel_Cinematic_Universe)

• Alex Duffy on LinkedIn: https://www.linkedin.com/in/alex-d/

• Danny Aziz on LinkedIn: https://www.linkedin.com/in/dannyaziz/

• Dia: https://www.diabrowser.com/

• Reid Hoffman’s website: https://www.reidhoffman.org/

• Starting Line VC: https://www.startingline.vc/

• Walleye Capital: https://walleyecapital.com/

• At This $10 Billion Hedge Fund, Using AI Just Became Mandatory: https://every.to/podcast/at-this-10-billion-hedge-fund-using-ai-just-became-mandatory

• Reflexive AI usage is now a baseline expectation at Shopify: https://x.com/tobi/status/1909251946235437514

• Klarna CEO Sebastian Siemiatkowski on Getting AI to Do the Work of 700 Customer Service Reps: https://www.sequoiacap.com/podcast/training-data-sebastian-siemiatkowski/

• The Pin Factory: https://www.adamsmithworks.org/pin_factory.html

• Deadwood on HBO: https://www.hbo.com/deadwood

• Joel Spolsky on X: https://x.com/spolsky

• Jason Fried’s website: https://world.hey.com/jason

• Jason Fried challenges your thinking on fundraising, goals, growth, and more: https://www.lennysnewsletter.com/p/jason-fried-challenges-your-thinking

• Sam Harris’s website: https://www.samharris.org/

• Bill Simmons on X: https://x.com/billsimmons

—

Recommended books:

• War and Peace: https://www.amazon.com/War-Peace-Vintage-Classics-Tolstoy/dp/1400079985

• Anna Karenina: https://www.amazon.com/Anna-Karenina-Leo-Tolstoy/dp/0143035002

• Playing and Reality: https://www.amazon.com/Playing-Reality-Routledge-Classics-86/dp/0415345464

• The Death of Ivan Ilyich: https://www.amazon.com/Death-Ivan-Ilyich-Leo-Tolstoy/dp/1468014315

• A Swim in a Pond in the Rain: https://www.amazon.com/Swim-Pond-Rain-Russians-Writing/dp/1984856022

• The Master and His Emissary: The Divided Brain and the Making of the Western World: https://www.amazon.com/Master-His-Emissary-Divided-Western/dp/0300245920/

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

Lenny may be an investor in the companies discussed.

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.

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.linkedin.com/in/jake-knapp/

• Website: https://jakeknapp.com/

—

Where to find John Zeratsky:

• X: https://twitter.com/jazer

• LinkedIn: https://www.linkedin.com/in/johnzeratsky/

• Website: https://johnzeratsky.com/

—

In this episode, we cover:

(00:00) Introduction to Jake Knapp and John Zeratsky

(04:41) Origins of the Design Sprint

(11:06) The Foundation Sprint process

(14:40) Phase one: The basics

(16:57) Case study: Latchet

(28:50) Phase two: Differentiation

(36:24) The importance of differentiation

(40:15) Thoughts on price differentiation

(43:37) Case study: Mellow

(46:04) Custom differentiators

(49:30) The mini manifesto

(52:02) Phase three: Approach to the project

(54:50) Magic lenses activity

(01:02:39) Prototyping and testing

(01:10:00) Real-world examples and success stories

(01:15:15) Motivation behind The Foundation Sprint

(01:17:15) The outcome of the sprint: The founding hypothesis

(01:19:28) The Design Sprint

(01:28:19) The role of AI in prototyping

(01:36:50) Final thoughts and resources

—

Referenced:

• Introducing the Foundation Sprint: From the creators of the Design Sprint: https://www.lennysnewsletter.com/p/introducing-the-foundation-sprint

• Making time for what matters | Jake Knapp and John Zeratsky (authors of Sprint and Make Time, co-founders of Character Capital): https://www.lennysnewsletter.com/p/making-time-for-what-matters-jake

• Eli Blee-Goldman on LinkedIn: https://www.linkedin.com/in/eli-blee-goldman/

• Character Capital: https://www.character.vc/

• Character Labs: https://www.character.vc/labs

• Etsy: https://www.etsy.com/

• Shopify: https://www.shopify.com/

• Naming expert shares the process behind creating billion-dollar brand names like Azure, Vercel, Windsurf, Sonos, Blackberry, and Impossible Burger | David Placek (Lexicon Branding): https://www.lennysnewsletter.com/p/naming-expert-david-placek

• Sonos: https://www.sonos.com/

• Vercel: https://vercel.com/

• Windsurf: https://windsurf.com/

• April Dunford on product positioning, segmentation, and optimizing your sales process: https://www.lennysnewsletter.com/p/april-dunford-on-product-positioning

• Positioning: https://www.lennysnewsletter.com/p/positioning

• 10 things we know to be true: https://about.google/company-info/philosophy/

• Gandalf: https://en.wikipedia.org/wiki/Gandalf

• Frodo: https://en.wikipedia.org/wiki/Frodo_Baggins

• Mordor: https://en.wikipedia.org/wiki/Mordor

• 35 years of product design wisdom from Apple, Disney, Pinterest, and beyond | Bob Baxley: https://www.lennysnewsletter.com/p/35-years-of-product-design-wisdom-bob-baxley

• The Primal Mark: How the Beginning Shapes the End in the Development of Creative Ideas: https://www.gsb.stanford.edu/faculty-research/publications/primal-mark-how-beginning-shapes-end-development-creative-ideas

• Base44: https://base44.com/

• Solo founder, $80M exit, 6 months: The Base44 bootstrapped startup success story | Maor Shlomo: https://www.lennysnewsletter.com/p/the-base44-bootstrapped-startup-success-story-maor-shlomo

• Google Meet: https://meet.google.com/

• Blue Bottle Coffee: https://bluebottlecoffee.com

• Reclaim: https://reclaim.ai/

• The official Foundation Sprint + Design Sprint template: https://www.character.vc/miro-template

• Rippling: https://www.rippling.com/

• Latchet: https://latchet.com/

• Mellow: http://getmellow.com/

• AxionOrbital: https://axionorbital.space/

—

Recommended books:

• Sprint: How to Solve Big Problems and Test New Ideas in Just Five Days: https://www.amazon.com/Sprint-audiobook/dp/B019R2DQIY

• Make Time: How to Focus on What Matters Every Day: https://www.amazon.com/Make-Time-Focus-Matters-Every/dp/0525572422

• Click: How to Make What People Want: https://www.amazon.com/Click-Make-What-People-Want/dp/1668072114

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

—

Lenny may be an investor in the companies discussed.

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.

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.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

—

In this episode, we cover:

(00:00) Introduction to Maor and Base44

(08:16) The origin story: how Base44 came to be

(14:55) Bootstrapping and solo founding: challenges and insights

(22:52) Productivity hacks and tech stack for solo founders

(27:23) How to get started using Base44

(28:47) Thoughts on raising money

(34:05) Distribution in the age of AI

(36:09) Ambition and goals

(40:05) Growth strategies: from first users to thousands

(51:32) Building in public

(57:42) The solo founder journey

(01:00:23) Community support

(01:03:23) Hackathons and partnerships

(01:06:42) The importance of velocity in product development

(01:08:20) Technical stack and infrastructure insights

(01:15:24) Activation lessons

(01:18:19) The acquisition journey with Wix

(01:25:14) Final thoughts and advice for founders

—

Referenced:

• Base44: https://base44.com/

• Retool: https://retool.com/

• Tzofim: https://www.israelscouts.org/

• Y Combinator: https://www.ycombinator.com/

• RescueTime: https://www.rescuetime.com/

• Cursor: https://www.cursor.com/

• Wix: https://www.wix.com/

• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell

• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika

• Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder and CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons

• Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad

• Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch

• Snowflake: https://www.snowflake.com

• Yoav Orlev on LinkedIn: https://www.linkedin.com/in/yoav-orlev-4a044b72

• WhatsApp: https://www.whatsapp.com/

• Amazon: https://www.amazon.com/

• Google: https://about.google/

• MongoDB: https://www.mongodb.com/

• Deloitte: https://www.deloitte.com/

• Render: Render.com

• Claude 4: https://www.anthropic.com/news/claude-4

• Gemini: https://gemini.google.com/app

• Cloudflare: https://www.cloudflare.com/

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

Lenny may be an investor in the companies discussed.

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.

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 device

(53:13) Job displacement and AI’s future impact

(58:20) Advice for new grads

(01:02:50) Parenting in the age of AI

(01:05:26) The pursuit of happiness beyond wealth

(01:10:10) Mental health and medication

(01:16:45) Lightning round and final thoughts

—

Referenced:

• Andrew’s post on X with the Charlie Munger quote: https://x.com/awilkinson/status/1265653805443506182

• Metalab: https://www.metalab.com/

• Letterboxd: https://letterboxd.com/

• AeroPress: https://aeropress.com/

• Brian Armstrong on X: https://x.com/brian_armstrong

• Warren Buffett’s quote: https://quotefancy.com/quote/931119/Warren-Buffett-I-am-a-better-investor-because-I-am-a-businessman-and-a-better-businessman

• Flow: https://www.getflow.com/

• Instacart: https://www.instacart.com/

• Things: https://culturedcode.com/things/

• Dustin Moskovitz on LinkedIn: https://www.linkedin.com/in/dmoskov/

• Salesforce: https://www.salesforce.com/

• Serato: https://serato.com/

• Chris Sparling on X: https://x.com/_sparling_

• Lindy: https://www.lindy.ai/

• Replit: https://replit.com/

• Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad

• David Ogilvy: https://en.wikipedia.org/wiki/David_Ogilvy_(businessman)

• Malcolm Gladwell’s website: https://www.gladwellbooks.com/

• Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder and CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons

• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika

• Limitless: https://www.limitless.ai/

• Perplexity: https://www.perplexity.ai/

• Claude: https://claude.ai/

• ChatGPT: https://chatgpt.com/

• Gemini: https://gemini.google.com/app

• William Gibson’s quote: https://www.goodreads.com/quotes/681-the-future-is-already-here-it-s-just-not-evenly

• Palm Treo: https://en.wikipedia.org/wiki/Palm_Treo

• Sam Altman on X: https://x.com/sama

• Dario Amodei on X: https://x.com/darioamodei

• Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next

• Challengers on AppleTV+: https://tv.apple.com/us/movie/challengers/umc.cmc.53cuz33n4e74ixj8whccj87oc

• Matic vacuum: https://maticrobots.com/

• Jerzy Gregorek’s quote: https://www.goodreads.com/quotes/8652595-hard-choices-easy-life-easy-choices-hard-life

• Tiny: https://www.tiny.com/

• Dribbble: https://dribbble.com/

—

Recommended books:

• The Laws of Human Nature: https://www.amazon.com/Laws-Human-Nature-Robert-Greene/dp/0525428143

• How to Get Rich: One of the World’s Greatest Entrepreneurs Shares His Secrets: https://www.amazon.com/How-Get-Rich-Greatest-Entrepreneurs/dp/1591842719

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

—

Lenny may be an investor in the companies discussed.

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.

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 in the AI era

(39:37) When to change your name

(43:10) The role of linguists

(45:54) The power of letters in branding

(48:15) The Vercel case study

(50:12) The implementation phase

(52:52) Client management and market success

(55:16) The diamond exercise

(01:04:23) Suspending judgment

(01:07:31) Polarization and boldness

(01:11:01) Domain names

(01:12:48) Final thoughts and lightning round

—

Referenced:

• PowerBook: https://en.wikipedia.org/wiki/PowerBook

• Pentium: https://en.wikipedia.org/wiki/Pentium

• BlackBerry: https://en.wikipedia.org/wiki/BlackBerry

• Swiffer: https://www.swiffer.com/

• Impossible Burger: https://impossiblefoods.com/

• Vercel: https://vercel.com/

• Windsurf: https://windsurf.com/

• CapCut: https://www.capcut.com/

• Azure: https://azure.microsoft.com/

• Sonos: https://www.sonos.com/

• John MacFarlane on LinkedIn: https://www.linkedin.com/in/john-macfarlane-08a8aa20/

• Harry Potter: https://en.wikipedia.org/wiki/Harry_Potter_(film_series)

• The Call of the Wild: https://en.wikipedia.org/wiki/The_Call_of_the_Wild

• Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch

• Sound symbolism: https://en.wikipedia.org/wiki/Sound_symbolism

• Anduril: https://www.anduril.com/

• Anthropic: https://www.anthropic.com/

• Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder and CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons

• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell

• Building a magical AI code editor used by over 1 million developers in four months: The untold story of Windsurf | Varun Mohan (co-founder and CEO): https://www.lennysnewsletter.com/p/the-untold-story-of-windsurf-varun-mohan

• Y Combinator: https://www.ycombinator.com/

• Chevrolet Corvette: https://en.wikipedia.org/wiki/Chevrolet_Corvette

• Viagra: https://www.viagra.com/

• In vino veritas: https://en.wikipedia.org/wiki/In_vino_veritas

• Infoseek: https://en.wikipedia.org/wiki/Infoseek

• Andy Grove: https://en.wikipedia.org/wiki/Andrew_Grove

• Churchill at War on Netflix: https://www.netflix.com/title/81609374

• Yellowstone on Prime Video: https://www.amazon.com/Yellowstone-Season-1/dp/B07D7FBB8Z

• 1883 on Prime Video: https://www.amazon.com/1883-Season-1/dp/B0B8JTS8QW

• 1923 on Paramount+: https://www.paramountplus.com/shows/1923/

• Taylor Sheridan on X: https://x.com/taylorSheridan

• Hardy fly rods: https://www.hardyfishing.com/collections/fly-rods

• T.E. Lawrence quote: https://www.goodreads.com/quotes/11340-all-men-dream-but-not-equally-those-who-dream-by

• Lawrence of Arabia: https://www.imdb.com/title/tt0056172/

• DreamWorks: https://www.dreamworks.com/

—

Recommended books:

• Thucydides’ Melian Dialogue: Commentary, Text, and Vocabulary: https://www.amazon.com/Thucydides-Melian-Dialogue-Commentary-Vocabulary/dp/0692772367

• Resilience: Hard-Won Wisdom for Living a Better Life: https://www.amazon.com/Resilience-Hard-Won-Wisdom-Living-Better/dp/054432398X/

• Churchill: Walking with Destiny: https://www.amazon.com/Churchill-Walking-Destiny-Andrew-Roberts/dp/1101980990

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

—

Lenny may be an investor in the companies discussed.

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.

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 and final thoughts

—

Referenced:

• OpenAI: https://openai.com/

• Artificial general intelligence (AGI): https://en.wikipedia.org/wiki/Artificial_general_intelligence

• Head of ChatGPT answers philosophical questions about AI at SXSW 2024 with SignalFire’s Josh Constine: https://www.youtube.com/watch?v=mgbgI0R6XCw

• Professors Are Using A.I., Too. Now What?: https://www.npr.org/2025/05/21/1252663599/kashmir-hill-ai#:~:text=Now%20What

• Herbert H. Clark: https://web.stanford.edu/~clark/

• Russian speakers get the blues: https://www.newscientist.com/article/dn11759-russian-speakers-get-the-blues/

• Ilya Sutskever (OpenAI Chief Scientist)—Building AGI, Alignment, Future Models, Spies, Microsoft, Taiwan, & Enlightenment: https://www.dwarkesh.com/p/ilya-sutskever

• Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next

• Kevin Systrom on LinkedIn: https://www.linkedin.com/in/kevinsystrom/

• Building a magical AI code editor used by over 1 million developers in four months: The untold story of Windsurf | Varun Mohan (co-founder and CEO): https://www.lennysnewsletter.com/p/the-untold-story-of-windsurf-varun-mohan

• Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada: https://www.lennysnewsletter.com/p/microsoft-cpo-on-ai

• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell

• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika

• Granola: https://www.granola.ai/

• Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder and CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons

• OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai

• Fidji Simo on LinkedIn: https://www.linkedin.com/in/fidjisimo/

• Airtable: https://www.airtable.com/

• George Lee on LinkedIn: https://www.linkedin.com/in/geolee/

• Andrew Chen on LinkedIn: https://www.linkedin.com/in/andrewchen/

• Lauryn Motamedi on LinkedIn: https://www.linkedin.com/in/laurynmotamedi/

• Twilio: https://www.twilio.com/

• Nick Turley on LinkedIn: https://www.linkedin.com/in/nicholasturley/

• Ian Silber on LinkedIn: https://www.linkedin.com/in/iansilber/

• Thomas Dimson on LinkedIn: https://www.linkedin.com/in/thomasdimson/

• Joey Flynn on LinkedIn: https://www.linkedin.com/in/joey-flynn-8291586b/

• Ryan O’Rourke’s website: https://www.rourkery.com/

• Joanne Jang on LinkedIn: https://www.linkedin.com/in/jangjoanne/

• Behind the founder: Marc Benioff: https://www.lennysnewsletter.com/p/behind-the-founder-marc-benioff

• Jill Hazelbaker on LinkedIn: https://www.linkedin.com/in/jill-hazelbaker-3aa32422/

• Guy Kawasaki’s website: https://guykawasaki.com/

• Eric Antonow on LinkedIn: https://www.linkedin.com/in/antonow/

• Sachin Kansal on LinkedIn: https://www.linkedin.com/in/sachinkansal/

• IDEO design thinking: https://designthinking.ideo.com/

• The 7 Steps of the Design Thinking Process: https://www.ideou.com/blogs/inspiration/design-thinking-process

• Linear’s secret to building beloved B2B products | Nan Yu (Head of Product): https://www.lennysnewsletter.com/p/linears-secret-to-building-beloved-b2b-products-nan-yu

• Jeff Bezos’s quote: https://news.ycombinator.com/item?id=27778175

• Friendster: https://en.wikipedia.org/wiki/Friendster

• Myspace: https://en.wikipedia.org/wiki/Myspace

• How LinkedIn became interesting: The inside story | Tomer Cohen (CPO at LinkedIn): https://www.lennysnewsletter.com/p/how-linkedin-became-interesting-tomer-cohen

• “Smile” by Jay-Z: https://www.youtube.com/watch?v=SSumXG5_rs8&list=RDSSumXG5_rs8&start_radio=1

• The Wire on HBO: https://www.hbo.com/the-wire

• Felicis: https://www.felicis.com/

—

Recommended books:

• Sapiens: A Brief History of Humankind: https://www.amazon.com/Sapiens-Humankind-Yuval-Noah-Harari/dp/0062316095

• The Design of Everyday Things: https://www.amazon.com/Design-Everyday-Things-Revised-Expanded/dp/0465050654

• The Silk Roads: A New History of the World: https://www.amazon.com/Silk-Roads-New-History-World/dp/1101912375

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

—

Lenny may be an investor in the companies discussed.

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.

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://www.linkedin.com/in/lennyrachitsky/

—

In this episode, we cover:

(00:00) Introduction to Sander Schulhoff

(04:29) The importance of prompt engineering

(06:30) Real-world applications and examples

(10:54) Basic prompt engineering techniques

(23:46) Advanced prompt engineering techniques

(29:00) The role of context and additional information

(39:24) Ensembling techniques and thought generation

(49:48) Conversational techniques for better results

(50:46) Introduction to prompt injection

(52:27) AI red teaming and competitions

(54:23) The growing importance of AI security

(01:02:45) Techniques to bypass AI safeguards

(01:05:21) Challenges in AI security and future outlook

(01:18:33) Misalignment and AI's potential risks

(01:25:03) Final thoughts and lightning round

—

Referenced:

• Reid Hoffman’s tweet about using AI agents: https://x.com/reidhoffman/status/1930416063616884822

• AI Engineer World’s Fair: https://www.ai.engineer/

• What Is Artificial Social Intelligence?: https://learnprompting.org/blog/asi

• Devin: https://devin.ai/

• Cursor: https://www.cursor.com/

• Inside Devin: The world’s first autonomous AI engineer that’s set to write 50% of its company’s code by end of year | Scott Wu (CEO and co-founder of Cognition): https://www.lennysnewsletter.com/p/inside-devin-scott-wu

• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell

• Granola: https://www.granola.ai/

• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika

• Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder & CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons

• Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad

• Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch

• Technique #3: Examples in Prompts: From Zero-Shot to Few-Shot: https://learnprompting.org/docs/basics/few_shot?srsltid=AfmBOor2owyGXtzJZ8n0fJVCctM7UPZgZmH-mBuxRW4t9-kkaMd3LJVv

• The Prompt Report: Insights from the Most Comprehensive Study of Prompting Ever Done: https://learnprompting.org/blog/the_prompt_report?srsltid=AfmBOoo7CRNNCtavzhyLbCMxc0LDmkSUakJ4P8XBaITbE6GXL1i2SvA0

• State-of-the-Art Prompting for AI Agents | Y Combinator: https://www.youtube.com/watch?v=DL82mGde6wo

• Use XML tags to structure your prompts: https://docs.anthropic.com/en/docs/build-with-claude/prompt-engineering/use-xml-tags

• Role Prompting: https://learnprompting.org/docs/basics/roles?srsltid=AfmBOor2jcxJQvWBZyFa030Qt0fIIov3hSiWvI9VFyjO-Qp478EPJIU7

• Is Role Prompting Effective?: https://learnprompting.org/blog/role_prompting?srsltid=AfmBOooiiyLD-0CsCYZ4m3SDhYOmtTyaTzeDo0FvK_i1x1gLM8MJS-Sn

• Introduction to Decomposition Prompting Techniques: https://learnprompting.org/docs/advanced/decomposition/introduction?srsltid=AfmBOoojJmTQgBlmSlGYQ8kl-JPpVUlLKkL4YcFGS5u54JyeumUwlcBI

• LLM Self-Evaluation: https://learnprompting.org/docs/reliability/lm_self_eval

• Philip Resnik on X: https://x.com/psresnik

• Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next

• Introduction to Ensembling Prompting: https://learnprompting.org/docs/advanced/ensembling/introduction?srsltid=AfmBOooGSyqsrjnEbXSYoKpG0ZlpT278NHQA6Fd8gMvNTJlWu7-qEYzh

• Random forest: https://en.wikipedia.org/wiki/Random_forest

• Chain-of-Thought Prompting: https://learnprompting.org/docs/intermediate/chain_of_thought?srsltid=AfmBOoqwE7SXlluy2sx_QY_VOKduyBplWtIWKEJaD6FkJW3TqeKPSJfx

• Prompt Injecting: https://learnprompting.org/docs/prompt_hacking/injection?srsltid=AfmBOoqGgqbfXStrD6vlw5jy8HhEaESgGo2e57jyWL8lkZKktt_P6Zvn

• Announcing HackAPrompt 2.0: The World’s Largest AI Red-Teaming Hackathon: https://learnprompting.org/blog/announce-hackaprompt-2?srsltid=AfmBOopXKsHxy4aUtsvPCUtEu7x74NCAEnlTIdNzo7nfMDVwZ9ilTlkp

• Infant with rare, incurable disease is first to successfully receive personalized gene therapy treatment: https://www.nih.gov/news-events/news-releases/infant-rare-incurable-disease-first-successfully-receive-personalized-gene-therapy-treatment

• Building a magical AI code editor used by over 1 million developers in four months: The untold story of Windsurf | Varun Mohan (co-founder and CEO): https://www.lennysnewsletter.com/p/the-untold-story-of-windsurf-varun-mohan

• Copilot: https://copilot.microsoft.com/chats/rcxhzvKgZvz8ajUrKdBtX

• GitHub Copilot: https://github.com/features/copilot

• Defensive Measures: https://learnprompting.org/docs/prompt_hacking/defensive_measures/introduction

• Sam Altman on X: https://x.com/sama

• Three Laws of Robotics: https://en.wikipedia.org/wiki/Three_Laws_of_Robotics

• Anthropic’s new AI model turns to blackmail when engineers try to take it offline: https://techcrunch.com/2025/05/22/anthropics-new-ai-model-turns-to-blackmail-when-engineers-try-to-take-it-offline/

• Palisade Research: https://palisaderesearch.org/

• When AI Thinks It Will Lose, It Sometimes Cheats, Study Finds: https://time.com/7259395/ai-chess-cheating-palisade-research/

• A.I. Chatbots Defeated Doctors at Diagnosing Illness: https://www.nytimes.com/2024/11/17/health/chatgpt-ai-doctors-diagnosis.html

• 1883 on Paramount+: https://www.paramountplus.com/shows/1883/

• Black Mirror on Netflix: https://www.netflix.com/title/70264888

• Daylight Computer: https://daylightcomputer.com/

• Theodore Roosevelt’s quote: https://www.goodreads.com/quotes/622252-i-wish-to-preach-not-the-doctrine-of-ignoble-ease

• HackAPrompt 2.0: https://www.hackaprompt.com/

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Recommended books:

• Ender’s Game: https://www.amazon.com/Enders-Ender-Quintet-Orson-Scott/dp/0812550706

• The River of Doubt: Theodore Roosevelt’s Darkest Journey: https://www.amazon.com/River-Doubt-Theodore-Roosevelts-Darkest/dp/0767913736

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

—

Lenny may be an investor in the companies discussed.

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.

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

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—

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

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Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

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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

(41:49) How to use “magic questions” to decode how people think

(49:54) Why you’re not the protagonist at your company

(52:48) Aligning with the CEO's vision

(01:01:02) Building effective habits

(01:11:14) Promoting team well-being

(01:14:28) Creating space for creativity

(01:20:45) AI’s role in accelerating learning

(01:30:35) Pivotal career moments

(01:37:21) Lessons from failure

(01:39:49) Exciting new features of WHOOP 5.0

(01:44:19) Lightning round and final thoughts

—

Referenced:

• How to become a supermanager with AI: https://www.lennysnewsletter.com/p/how-to-become-a-supermanager-with

• How custom GPTs can make you a better manager | Hilary Gridley (Head of Core Product at Whoop): https://www.lennysnewsletter.com/p/how-custom-gpts-can-make-you-a-better-manager

• WHOOP: https://www.whoop.com/

• Big Health: https://www.bighealth.com/

• What is behavioral activation?: https://www.medicalnewstoday.com/articles/behavioral-activation

• Will Ahmed on LinkedIn: https://www.linkedin.com/in/willahmed/

• Joe Gebbia on LinkedIn: https://www.linkedin.com/in/jgebbia/

• Zach Abrams on LinkedIn: https://www.linkedin.com/in/zacharyabrams/

• Coinbase: https://www.coinbase.com/

• Bridge: https://www.bridge.xyz/

• Stripe: https://stripe.com/

• The paths to power: How to grow your influence and advance your career | Jeffrey Pfeffer (author of 7 Rules of Power, professor at Stanford GSB): https://www.lennysnewsletter.com/p/the-paths-to-power-jeffrey-pfeffer

• Paths to Power course: https://jeffreypfeffer.com/wp-content/uploads/2019/10/Pfeffer-OB377-Course-Outline-2018.pdf

• VO₂ max: https://en.wikipedia.org/wiki/VO2_max

• Peter Attia on X: https://x.com/PeterAttiaMD

• Hilary Gridley’s 30 days of GPT: https://docs.google.com/spreadsheets/d/1zJ4rbi9YcQuGqGxc6-AQD0-44oT9l4Eyono0AdpgJbA/edit?gid=0#gid=0

• The Handle Bar in Boston: https://www.thehandlebarstudios.com/ourstudios/charlestown

• From chalkboards to chatbots: Transforming learning in Nigeria, one prompt at a time: https://blogs.worldbank.org/en/education/From-chalkboards-to-chatbots-Transforming-learning-in-Nigeria

• Product Management Logic Coach GPT: https://chatgpt.com/g/g-673290301700819084afa36bdbcdfa3b-product-management-logic-coach

• Dropbox: https://www.dropbox.com/

• WHOOP Advanced Labs: https://www.whoop.com/us/en/waitlist/?srsltid=AfmBOor2pP5qC3n7I23Z0ZIrYE99CjAKT9xSHQxbuyxmz_wFUBGH3e-n

• Negative capability: https://en.wikipedia.org/wiki/Negative_capability

• John Keats: https://en.wikipedia.org/wiki/John_Keats

• The Rehearsal: https://www.hbo.com/the-rehearsal

• Zwift: https://www.zwift.com/

• Beavis and Butthead Do ‘Creep’: https://www.youtube.com/watch?v=zv_gSmH0Ieg

• “Sea Grapes” by Derek Walcott: https://www.poetryfoundation.org/poems/57111/sea-grapes

• Free month of WHOOP: https://join.whoop.com/us/en/hilary/

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Recommended books:

• 7 Rules of Power: https://jeffreypfeffer.com/books/7-rules-of-power/

• Outlive: The Science and Art of Longevity: https://www.amazon.com/Outlive-Longevity-Peter-Attia-MD/dp/0593236599

• East of Eden: https://www.amazon.com/East-Eden-John-Steinbeck-Centennial/dp/0142004235

• The Sun Also Rises: https://www.amazon.com/Sun-Also-Rises-Hemingway-Library/dp/1501121960/

• Anna Karenina: https://www.amazon.com/Anna-Karenina-Leo-Tolstoy/dp/0143035002

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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

—

Lenny may be an investor in the companies discussed.