Lenny's Podcast: Product | Growth | Career

AI is rapidly changing how we live and work. Its exciting, but also overwhelming. If youre struggling to keep up, and wondering how to actually use these magical new tools to improve the quality and efficiency of your work, Im thrilled to introduce How I AI with Claire Vothe first ever new podcast under the Lennys Podcast network. Claire is an engineer, three-time CPO, and AI builder. In each episode, her guest shows you a specific, practical, and impactful way theyve learned to use AI. Forget theoretical debatesthis podcast is about real, valuable use cases. Expect 30-minute episodes, live demos, and tips/tricks/workflows you can implement immediately. Whether youre building products, leading teams, or just looking to level up your AI skills, How I AI is for you.

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Varun Mohan is the co-founder and CEO of Windsurf (formerly Codeium), an AI-powered development environment (IDE) that has been used by over 1 million developers in just four months and has quickly emerged as a leader in transforming how developers build software. Prior to finding success with Windsurf, the company pivoted twice—first from GPU virtualization infrastructure to an IDE plugin, and then to their own standalone IDE.

In this conversation, you'll learn:

1. Why Windsurf walked away from a profitable GPU infrastructure business and bet the company on helping engineers code

2. The surprising UI discovery that tripled adoption rates overnight.

3. The secret behind Windsurf's B2B enterprise plan, and why they invested early in an 80-person sales team despite conventional startup wisdom.

4. How non-technical staff at Windsurf built their own custom tools instead of purchasing SaaS products, saving them over $500k in software costs

5. Why Varun believes 90% of code will be AI-generated, but engineering jobs will actually increase

6. How training on millions of incomplete code samples gives Windsurf an edge, and creates a moat long-term

7. Why agency is the most undervalued and important skill in the AI era

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Brought to you by:

• Brex—The banking solution for startups

• Productboard—Make products that matter

• Coda—The all-in-one collaborative workspace

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Where to find Varun Mohan:

• X: https://x.com/_mohansolo

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

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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) Varun’s background

(03:57) Building and scaling Windsurf

(12:58) Windsurf: The new purpose-built IDE to harness magic

(17:11) The future of engineering and AI

(21:30) Skills worth investing in

(23:07) Hiring philosophy and company culture

(35:22) Sales strategy and market position

(39:37) JetBrains vs. VS Code: extensibility and enterprise adoption

(41:20) Live demo: building an Airbnb for dogs with Windsurf

(42:46) Tips for using Windsurf effectively

(46:38) AI’s role in code modification and review

(48:56) Empowering non-developers to build custom software

(54:03) Training Windsurf

(01:00:43) Windsurf’s unique team structure and product strategy

(01:06:40) The importance of continuous innovation

(01:08:57) Final thoughts and advice for aspiring developers

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Referenced:

• Windsurf: https://windsurf.com/

• VS Code: https://code.visualstudio.com/

• JetBrains: https://www.jetbrains.com/

• Eclipse: https://eclipseide.org/

• Visual Studio: https://visualstudio.microsoft.com/

• Vim: https://www.vim.org/

• Emacs: https://www.gnu.org/software/emacs/

• Lessons from a two-time unicorn builder, 50-time startup advisor, and 20-time company board member | Uri Levine (co-founder of Waze): https://www.lennysnewsletter.com/p/lessons-from-uri-levine

• IntelliJ: https://www.jetbrains.com/idea/

• Julia: https://julialang.org/

• Parallel computing: https://en.wikipedia.org/wiki/Parallel_computing

• Douglas Chen on LinkedIn: https://www.linkedin.com/in/douglaspchen/

• Carlos Delatorre on LinkedIn: https://www.linkedin.com/in/cadelatorre/

• MongoDB: https://www.mongodb.com/

• Cursor: https://www.cursor.com/

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

• Llama: https://www.llama.com/

• Mistral: https://mistral.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

• React: https://react.dev/

• Sonnet: https://www.anthropic.com/claude/sonnet

• OpenAI: https://openai.com/

• FedRamp: https://www.fedramp.gov/

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

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

• How to win in the AI era: Ship a feature every week, embrace technical debt, ruthlessly cut scope, and create magic your competitors can't copy | Gaurav Misra (CEO and co-founder of Captions): https://www.lennysnewsletter.com/p/how-to-win-in-the-ai-era-gaurav-misra

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Recommended book:

• Fall in Love with the Problem, Not the Solution: A Handbook for Entrepreneurs: https://www.amazon.com/Fall-Love-Problem-Solution-Entrepreneurs/dp/1637741987

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

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Lenny may be an investor in the companies discussed.

Guillermo Rauch is the founder and CEO of Vercel, creators of v0 (one of the most popular AI app building tools), and the mind behind foundational JavaScript frameworks like Next.js and Socket.io. An open source pioneer and legendary engineer, Guillermo has built tools that power some of the internet’s most innovative products, including Midjourney, Grok, and Notion. His mission is to democratize product creation, expanding the pool of potential builders from 5 million developers to over 100 million people worldwide.

In this episode, you’ll learn:

1. How AI will radically speed up product development—and the three critical skills PMs and engineers should master now to stay ahead

2. Why the future of building apps is shifting toward prompts instead of code, and how that affects traditional product teams

3. Specific ways to improve your design “taste,” plus practical tips to consistently create beautiful, user-loved products

4. How Guillermo built a powerful app in under two hours for $20 (while flying and using plane Wi-Fi) that would normally take weeks and thousands of dollars in engineering time

5. The exact strategies Vercel uses internally to leverage AI tools like v0 and Cursor, enabling their team of 600 to ship faster and better than ever before

6. Guillermo’s actionable advice on increasing your product quality through rapid iteration, real-world user feedback, and creating intentional “exposure hours” for your team

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Brought to you by:

• WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs

• Vanta — Automate compliance. Simplify security

• LinkedIn Ads—Reach professionals and drive results for your business

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Where to find Guillermo Rauch:

• X: https://x.com/rauchg

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

• Website: https://rauchg.com/

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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) Introduction to Guillermo Rauch

(04:43) v0's mission

(07:03) The impact and growth of v0

(15:54) The future of product development with AI

(19:05) Empowering engineers and product builders

(24:01) Skills for the future: coding, math, and eloquence

(35:05) v0 in action: real-world applications

(36:40) Tips for using v0 effectively

(45:46) Core skills for building AI apps

(49:44) Live demo

(59:45) Understanding how AI thinks

(01:04:35) AI integration and future prospects

(01:07:22) Building taste

(01:13:43) Limitations of v0

(01:16:54) Improving the design of your product

(01:20:09) The secret to product quality

(01:22:35) Vercel’s AI-driven development

(01:25:43) Guillermo's vision for the future

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Referenced:

• v0: https://v0.dev/

• Vercel: https://vercel.com/

• GitHub: https://github.com/

• Cursor: https://www.cursor.com/

• Next.js Framework: https://nextjs.org/

• Claude: https://claude.ai/new

• Grok: https://x.ai/

• Midjourney: https://www.midjourney.com

• SocketIO: https://socket.io/

• Notion’s lost years, its near collapse during Covid, staying small to move fast, the joy and suffering of building horizontal, more | Ivan Zhao (CEO and co-founder): https://www.lennysnewsletter.com/p/inside-notion-ivan-zhao

• Notion: https://www.notion.com/

• Automattic: https://automattic.com/

• 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

• v0 Community: https://v0.dev/chat/community

• Figma: https://www.figma.com/

• Git Commit: https://www.atlassian.com/git/tutorials/saving-changes/git-commit

• What are Artifacts and how do I use them?: https://support.anthropic.com/en/articles/9487310-what-are-artifacts-and-how-do-i-use-them

• Design Engineering at Vercel: https://vercel.com/blog/design-engineering-at-vercel

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

• Tailwind: https://tailwindcss.com/

• Wordcel / Shape Rotator / Mathcel: https://knowyourmeme.com/memes/wordcel-shape-rotator-mathcel

• Steve Jobs’s Ultimate Lesson for Companies: https://hbr.org/2011/08/steve-jobss-ultimate-lesson-fo

• Bloom Hackathon: https://bloom.build/

• Expenses Should Do Themselves | Saquon Barkley x Ramp (Super Bowl Ad): https://www.youtube.com/watch?v=p1Tgsy7D0Jg

• Velocity over everything: How Ramp became the fastest-growing SaaS startup of all time | Geoff Charles (VP of Product): https://www.lennysnewsletter.com/p/velocity-over-everything-how-ramp

• JavaScript: https://www.javascript.com/

• React: https://react.dev/

• Mapbox: https://www.mapbox.com/

• Leaflet: https://leafletjs.com/

• Escape hatches: https://react.dev/learn/escape-hatches

• Supreme: https://supreme.com/

• Shadcn: https://ui.shadcn.com/

• Charles Schwab: https://www.schwab.com/

• Fortune: https://fortune.com/

• Semafor: https://www.semafor.com/

• AI SDK: https://sdk.vercel.ai/

• DeepSeek: https://www.deepseek.com/

• Stripe: https://stripe.com/

• Vercel templates: https://vercel.com/templates

• GC AI: https://getgc.ai/

• OpenEvidence: https://www.openevidence.com/

• Paris Fashion Week: https://www.fhcm.paris/en/paris-fashion-week

• Guillermo’s post on X about making great products: https://x.com/rauchg/status/1887314115066274254

• Everybody Can Cook billboard: https://www.linkedin.com/posts/evilrabbit_activity-7242975574242037760-uRW9/

• Ratatouille: https://www.imdb.com/title/tt0382932/

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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.

Kevin Weil is the chief product officer at OpenAI, where he oversees the development of ChatGPT, enterprise products, and the OpenAI API. Prior to OpenAI, Kevin was head of product at Twitter, Instagram, and Planet, and was instrumental in the development of the Libra (later Novi) cryptocurrency project at Facebook.

In this episode, you’ll learn:

1. How OpenAI structures its product teams and maintains agility while developing cutting-edge AI

2. The power of model ensembles—using multiple specialized models together like a company of humans with different skills

3. Why writing effective evals (AI evaluation tests) is becoming a critical skill for product managers

4. The surprisingly enduring value of chat as an interface for AI, despite predictions of its obsolescence

5. How “vibe coding” is changing how companies operate

6. What OpenAI looks for when hiring product managers (hint: high agency and comfort with ambiguity)

7. “Model maximalism” and why today’s AI is the worst you’ll ever use again

8. Practical prompting techniques that improve AI interactions, including example-based prompting

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Brought to you by:

• Eppo—Run reliable, impactful experiments

• Persona—A global leader in digital identity verification

• OneSchema—Import CSV data 10x faster

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Where to find Kevin Weil:

• X: https://x.com/kevinweil

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

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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) Kevin’s background

(04:06) OpenAI’s new image model

(06:52) The role of chief product officer at OpenAI

(10:18) His recruitment story and joining OpenAI

(17:20) The importance of evals in AI

(24:59) Shipping quickly and consistently

(28:34) Product reviews and iterative deployment

(39:35) Chat as an interface for AI

(43:59) Collaboration between researchers and product teams

(46:41) Hiring product managers at OpenAI

(48:45) Embracing ambiguity in product management

(51:41) The role of AI in product teams

(53:21) Vibe coding and AI prototyping

(55:55) The future of product teams and fine-tuned models

(01:04:36) AI in education

(01:06:42) Optimism and concerns about AI’s future

(01:16:37) Reflections on the Libra project

(01:20:37) Lightning round and final thoughts

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Referenced:

• OpenAI: https://openai.com/

• The AI-Generated Studio Ghibli Trend, Explained: https://www.forbes.com/sites/danidiplacido/2025/03/27/the-ai-generated-studio-ghibli-trend-explained/

• Introducing 4o Image Generation: https://openai.com/index/introducing-4o-image-generation/

• Waymo: https://waymo.com/

• X: https://x.com

• Facebook: https://www.facebook.com/

• Instagram: https://www.instagram.com/

• Planet: https://www.planet.com/

• Sam Altman on X: https://x.com/sama

• A conversation with OpenAI’s CPO Kevin Weil, Anthropic’s CPO Mike Krieger, and Sarah Guo: https://www.youtube.com/watch?v=IxkvVZua28k

• OpenAI evals: https://github.com/openai/evals

• Deep Research: https://openai.com/index/introducing-deep-research/

• Ev Williams on X: https://x.com/ev

• OpenAI API: https://platform.openai.com/docs/overview

• Dwight Eisenhower quote: https://www.brainyquote.com/quotes/dwight_d_eisenhower_164720

• 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

• StackBlitz: https://stackblitz.com/

• Claude 3.5 Sonnet: https://www.anthropic.com/news/claude-3-5-sonnet

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

• Four-minute mile: https://en.wikipedia.org/wiki/Four-minute_mile

• Chad: https://chatgpt.com/g/g-3F100ZiIe-chad-open-a-i

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

• Figma: https://www.figma.com/

• Julia Villagra on LinkedIn: https://www.linkedin.com/in/juliavillagra/

• Andrej Karpathy on X: https://x.com/karpathy

• Silicon Valley CEO says ‘vibe coding’ lets 10 engineers do the work of 100—here’s how to use it: https://fortune.com/2025/03/26/silicon-valley-ceo-says-vibe-coding-lets-10-engineers-do-the-work-of-100-heres-how-to-use-it/

• Cursor: https://www.cursor.com/

• Windsurf: https://codeium.com/windsurf

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

• Patrick Srail on X: https://x.com/patricksrail

• Khan Academy: https://www.khanacademy.org/

• CK-12 Education: https://www.ck12.org/

• Sora: https://openai.com/sora/

• Sam Altman’s post on X about creative writing: https://x.com/sama/status/1899535387435086115

• Diem (formerly known as Libra): https://en.wikipedia.org/wiki/Diem_(digital_currency)

• Novi: https://about.fb.com/news/2020/05/welcome-to-novi/

• David Marcus on LinkedIn: https://www.linkedin.com/in/dmarcus/

• Peter Zeihan on X: https://x.com/PeterZeihan

• The Wheel of Time on Prime Video: https://www.amazon.com/Wheel-Time-Season-1/dp/B09F59CZ7R

• Top Gun: Maverick on Prime Video: https://www.amazon.com/Top-Gun-Maverick-Joseph-Kosinski/dp/B0DM2LYL8G

• Thinking like a gardener not a builder, organizing teams like slime mold, the adjacent possible, and other unconventional product advice | Alex Komoroske (Stripe, Google): https://www.lennysnewsletter.com/p/unconventional-product-advice-alex-komoroske

• MySQL: https://www.mysql.com/

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Recommended books:

• Co-Intelligence: Living and Working with AI: https://www.amazon.com/Co-Intelligence-Living-Working-Ethan-Mollick/dp/059371671X

• The Accidental Superpower: Ten Years On: https://www.amazon.com/Accidental-Superpower-Ten-Years/dp/1538767341

• Cable Cowboy: https://www.amazon.com/Cable-Cowboy-Malone-Modern-Business/dp/047170637X

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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.

Wes Kao is an entrepreneur, coach, and advisor. She co-founded the live learning platform Maven, backed by First Round and a16z. Before Maven, Wes co-created the altMBA with best-selling author Seth Godin. Today, Wes teaches a popular course on executive communication and influence. Through her course and one-on-one coaching, she’s helped thousands of operators, founders, and product leaders master the art of influence through clear, compelling communication. Known for her surgical writing style and no-BS frameworks, Wes returns to the pod to deliver a tactical master class on becoming a sharper, more persuasive communicator—at work, in meetings, and across your career.

What you’ll learn:

1. The #1 communication mistake leaders make—and Wes’s proven fix to instantly gain buy-in

2. Wes’s MOO (Most Obvious Objection) framework to consistently anticipate and overcome pushback in meetings

3. How to master concise communication—including Wes’s tactical approach for brevity without losing meaning

4. The art of executive presence: actionable strategies for conveying confidence and clarity, even under pressure

5. The “sales, then logistics” framework—and why your ideas keep getting ignored without it

6. The power of “signposting”—and why executives skim your docs without it

7. Exactly how to give feedback that works—Wes’s “strategy, not self-expression” principle to drive behavior change without friction

8. Practical ways to instantly improve your writing, emails, and Slack messages—simple techniques Wes teaches executives

9. Managing up like a pro: Wes’s clear, practical advice on earning trust, building credibility, and aligning with senior leaders

10. Career accelerators: specific habits and tactics from Wes for growing your influence, advancing your career, and standing out

11. Real-world communication examples—Wes breaks down real scenarios she’s solved, providing step-by-step solutions you can copy today

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Brought to you by:

• WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs

• Vanta—Automate compliance. Simplify security

• Coda—The all-in-one collaborative workspace

—

Where to find Wes Kao:

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

• Website: https://www.weskao.com/

• Maven course: https://maven.com/wes-kao/executive-communication-influence

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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) Introduction to Wes Kao

(05:34) Working with Wes

(06:58) The importance of communication

(10:44) Sales before logistics

(18:20) Being concise

(24:31) Books to help you become a better writer

(27:30) Signposting and formatting

(32:05) How to develop and practice your communication skills

(40:41) Slack communication

(42:23) Confidence in communication

(50:17) The MOO framework

(54:00) Staying calm in high-stakes conversations

(57:36) Which tactic to start with

(58:53) Effective tactics for managing up

(01:04:53) Giving constructive feedback: strategy, not self-expression

(01:09:39) Delegating effectively while maintaining high standards

(01:16:36) The swipe file: collecting inspiration for better communication

(01:19:59) Leveraging AI for better communication

(01:22:01) Lightning round

—

Referenced:

• Persuasive communication and managing up | Wes Kao (Maven, Seth Godin, Section4): https://www.lennysnewsletter.com/p/persuasive-communication-wes-kao

• Making Meta | Andrew ‘Boz’ Bosworth (CTO): https://www.lennysnewsletter.com/p/making-meta-andrew-boz-bosworth-cto

• Communication is the job: https://boz.com/articles/communication-is-the-job

• Maven: https://maven.com/

• Sales, not logistics: https://newsletter.weskao.com/p/sales-not-logistics

• How to be more concise: https://newsletter.weskao.com/p/how-to-be-concise

• Signposting: How to reduce cognitive load for your reader: https://newsletter.weskao.com/p/sign-posting-how-to-reduce-cognitive

• Airbnb’s Vlad Loktev on embracing chaos, inquiry over advocacy, poking the bear, and “impact, impact, impact” (Partner at Index Ventures, Airbnb GM/VP Product): https://www.lennysnewsletter.com/p/impact-impact-impact-vlad-loktev

• Tone and words: Use accurate language: https://newsletter.weskao.com/p/tone-and-words-use-accurate-language

• Quote by Joan Didion: https://www.goodreads.com/quotes/264509-i-don-t-know-what-i-think-until-i-write-it

• Strategy, not self-expression: How to decide what to say when giving feedback: https://newsletter.weskao.com/p/strategy-not-self-expression

• 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

• The CEDAF framework: Delegating gets easier when you get better at explaining your ideas: https://newsletter.weskao.com/p/delegating-and-explaining

• Swipe file: https://en.wikipedia.org/wiki/Swipe_file

• Apple Notes: https://apps.apple.com/us/app/notes/id1110145109

• Claude: https://claude.ai/new

• ChatGPT: https://chatgpt.com/

• Arianna Huffington’s phone bed charging station (Oak): https://www.amazon.com/Arianna-Huffingtons-Phone-Charging-Station/dp/B079C5DBF4?th=1

• The Harlan Coben Collection on Netflix: https://www.netflix.com/browse/genre/81180221

• Oral-B Pro 1000 rechargeable electric toothbrush: https://www.amazon.com/dp/B003UKM9CO/

• The Best Electric Toothbrush: https://www.nytimes.com/wirecutter/reviews/best-electric-toothbrush/

• Glengarry Glen Ross on Prime Video: https://www.amazon.com/Glengarry-Glen-Ross-James-Foley/dp/B002NN5F7A

• 1,000,000: https://www.lennysnewsletter.com/p/1000000

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Recommended books:

• On Writing Well: The Classic Guide to Writing Nonfiction: https://www.amazon.com/Writing-Well-Classic-Guide-Nonfiction/dp/0060891548/

• Stein on Writing: A Master Editor of Some of the Most Successful Writers of Our Century Shares His Craft Techniques and Strategies: https://www.amazon.com/Stein-Writing-Successful-Techniques-Strategies/dp/0312254210/

• On Writing: A Memoir of the Craft: https://www.amazon.com/Writing-Memoir-Craft-Stephen-King/dp/1982159375

• Several Short Sentences About Writing: https://www.amazon.com/Several-Short-Sentences-About-Writing/dp/0307279413/

• High Output Management: https://www.amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884

• Your Brain at Work: Strategies for Overcoming Distraction, Regaining Focus, and Working Smarter All Day Long: https://www.amazon.com/Your-Brain-Work-Revised-Updated/dp/0063003155/

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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.