2025-08-08 01:15:26
Why is this in your inbox? Because How I AI, hosted by Claire Vo, is part of the Lenny’s Podcast Network. Every Monday, we share a 30- to 45-minute episode with a new guest demoing a practical, impactful way they’ve learned to use AI in their work or life. No pontificating—just specific and actionable advice. Prefer to skip future episode drops? Unsubscribe from How I AI podcast notifications here.
Brought to you by ChatPRD—an AI copilot for PMs and their teams
In this episode, I share my hands-on experience with OpenAI’s GPT-5, the company’s new frontier model. As one of the first users outside of OpenAI to test the model, I put GPT-5 head-to-head with GPT-4.1 across real-world product use cases—from writing PRDs to generating code to assisting with visual design work. This is my unfiltered look at what GPT-5 can (and can’t) do—and how it changes the game for builders.
What you’ll learn:
1. How GPT-5 differs from previous models with its engineering-focused approach to problem-solving and tendency to prioritize technical details over business context
2. A comparative analysis of how GPT-5 and GPT-4.1 generate different types of product requirement documents and prototypes for the same prompt
3. Why GPT-5 excels at technical writing, functional requirements, and code generation while potentially skipping important business discovery questions
4. The model’s impressive spatial awareness capabilities when generating images for interior design and other visual tasks
5. Practical considerations for choosing the right model based on your specific use case and audience
6. How GPT-5’s extensive tool-calling behavior and bullet-point communication style reflect its engineering-oriented design
To celebrate 25,000 YouTube followers, we’re doing a giveaway. Win a free year of my favorite AI products, including v0, Replit, Lovable, Bolt, Cursor, and, of course, ChatPRD, by leaving a rating and review on your favorite podcast app and subscribing to the podcast on YouTube. To enter: https://www.howiaipod.com/giveaway
ChatPRD: https://www.chatprd.ai/
Website: https://clairevo.com/
LinkedIn: https://www.linkedin.com/in/clairevo/
(00:00) Introduction to GPT-5
(04:34) Testing GPT-5 in ChatPRD for document generation
(07:10) Comparing GPT-5 and GPT-4.1 on business vs. technical orientation
(11:22) Side-by-side comparison of PRDs generated by both models
(15:23) Where GPT-5 excels: Technical considerations and documentation quality
(17:35) Comparing prototypes generated from different model outputs
(19:57) Testing homepage critique capabilities between models
(23:14) OpenAI’s strengths in API design and developer support
(25:37) GPT-5’s performance as a coding assistant
(27:26) Examining GPT-5 in ChatGPT’s interface
(28:50) Testing GPT-5’s front-end design capabilities
(31:17) Personal use case: bathroom remodel planning
(33:45) Comparing GPT-5 vs. GPT-4 for interior design visualization
(38:10) Summary of key findings and recommendations
• OpenAI: https://openai.com/
• ChatGPT: https://chat.openai.com/
• Claude: https://claude.ai/
• Gemini: https://gemini.google.com/
• Cursor: https://cursor.sh/
• v0: https://v0.dev/
• Lovable: https://lovable.dev/
• Bolt: https://bolt.com/
• LaunchDarkly AI Configs: https://launchdarkly.com/docs/home/ai-configs
• Benjamin Moore paints: https://www.benjaminmoore.com/
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
2025-08-05 21:03:39
👋 Welcome to a 🔒 subscriber-only edition 🔒 of my weekly newsletter. Each week I tackle reader questions about building product, driving growth, and accelerating your career. For more: Lenny’s Podcast | How I AI | Lennybot | Lenny’s Reads | Courses | Swag
Annual subscribers get a free year of Lovable, Bolt, n8n, Replit, Wispr Flow, Descript, Linear, Gamma, Superhuman, Granola, Warp, Perplexity, Raycast, Magic Patterns, Mobbin, and ChatPRD (while supplies last). Subscribe now.
What does it take to drive employee AI adoption at your company?
Longtime product operator and creator Peter Yang has been investigating, sharing, and applying AI best practices for years now, and he’s been getting this question more than any other. So have I! We decided to collaborate to bring you the best, most in-depth answer to this increasingly important topic.
Peter interviewed founders and product leaders at six fast-growing AI-forward companies and collected all of their best tactics for driving employee AI adoption. This post includes their best 25 battle-tested AI tips that you can implement right away at your company.
Peter shares more practical AI tips via his newsletter and YouTube channel.
P.S. You can now also listen to these posts in convenient podcast form: Spotify / Apple / YouTube.
I never feel alone anymore when I’m stuck on a problem.
From summarizing user feedback to crafting product strategy, having AI as a patient, knowledgeable, and always-available thought partner has completely transformed how I do product work.
But here’s the reality: According to a recent Gallup poll, only 8% of U.S. workers use AI daily. Meanwhile, teams that crack the AI adoption code are seeing incredible results. For example, Zapier’s sales reps save 10 hours per week on lead research, Ramp built AI user personas that give PMs instant feedback on any spec, and Duolingo went from 100 courses in 12 years to 150 courses in just 12 months with AI’s help.
From what I’ve seen and from talking to leaders at AI-forward companies, I’ve learned that:
The biggest barrier to AI adoption isn’t technology; it’s organizational change.
At many companies, employees are struggling with vague AI mandates, procurement bottlenecks, and lack of guidance on the highest-impact use cases to focus on first.
After interviewing leaders at the 6 AI-forward companies below, I’ve identified 5 recurring steps that companies can take to supercharge AI adoption:
Explain the how
Track and reward adoption
Cut the red tape
Turn enthusiasts into teachers
Prioritize the high-impact tasks
Let’s break down exactly how these companies made it work.
Saying “we are AI-first” means nothing if employees don’t know what that actually means for their day-to-day work.
The companies that succeed provide specific tactics that employees and teams can adopt to meet those expectations.
Here’s what this can look like:
Include specific tactics in your memo: Tobi Lütke, CEO of Shopify, didn’t just say that “using AI is now a baseline expectation” in his now-famous memo. Instead, he shared concrete tactics he expects to see, like making AI prototyping part of the company’s GSD (get shit done) process.
Declare a “code red” moment: Wade Foster, CEO of Zapier, called an all-hands-on-deck moment in March 2023 after ChatGPT’s launch. He then shared a playbook and gave all employees a week off to put it into practice.
Define what “embracing AI” means: Luis von Ahn, Duolingo’s CEO, defined AI adoption as both “making our products better” and “empowering employees to do their best work.” Teams were encouraged to use AI for everything from speeding up lesson creation to prototyping.
Embed with individual teams: Darragh Curran, Intercom’s CTO, set a goal to “2x productivity with AI” and then spent a week every month embedded with individual teams to identify and execute on the 2x opportunities.
Lead by example in real time: When a PM brings a problem to Hilary Gridley, Whoop’s Head of Product, she’ll say, “Want me to show you how I solve this with AI?” Then she shares her workflows live.
You don’t need to be an executive to drive this change. At Roblox, I constantly share my favorite AI workflows in Slack and one-on-ones. I’ve even started screen sharing AI’s output during meetings to solve problems with my teammates in real time. Seeing a colleague save time with AI is an incredibly strong incentive to try it yourself.
Like any good PM, you should track AI adoption as inputs (who’s using AI) and outputs (what business value it’s creating). You should also reward employees who are leading the charge to keep the momentum going.
Here’s how top companies are tracking and rewarding adoption:
Make AI adoption part of performance reviews: Shopify asks employees to rate colleagues on a 1-to-5 scale for how well they “reflexively use AI tools for improving and amplifying work outputs.”
Publish AI usage by team: At Ramp, leadership shares the number of AI power users (5+ actions a week) for tools like Cursor, Claude Code, and ChatGPT. This transparency creates natural accountability across teams.
Track team-specific impact: Zapier tracks the impact of AI adoption by function. In sales, for example, when targeted leads engage with marketing content, AI auto-packages that information for the account rep—leading to 10 hours saved per week per rep.
Use proxy metrics for productivity: Intercom tracks merged pull requests as a proxy for productivity gains. They’re already seeing a “durable improvement (about 20% year-over-year)” from AI-assisted development.
Make it a daily habit: Whoop gave employees a 30-day challenge with bite-size 2-minute tasks to complete and rewarded those who kept the longest streak.
The point is that:
People will change their behavior with the right incentives.
Tracking both the leading indicators (AI usage) and lagging indicators (business results) creates a link between AI adoption and the real impact on teams, businesses, and people’s careers. Connect the dots on impact for your employees and you’ll see adoption skyrocket.
Most companies have long approval processes for AI tools. But what they don’t realize is that their employees are already using AI. They’re just using it from their personal accounts.
Cut the red tape if you don’t want employees to use AI tools that aren’t approved:
Create an AI learning budget: Duolingo gave every employee $300 to try AI tools, courses, and subscriptions. This incentivizes constant experimentation.
Assign a lead to expedite approvals: Zapier assigned a lead PM to own working with procurement, legal, and engineering to fast-track AI tool approvals and eliminate bottlenecks.
Give employees time to tinker: “No time” was the main reason employees cited for not trying new AI tools, so Intercom CTO Darragh encouraged managers to give employees dedicated time to skill up.
Provide multiple tool options: Shopify provides access to a wide range of tools, including Claude, Perplexity, Cohere, Gemini, Cursor, Copilot, and Claude Code. They also encourage employees to contribute to a growing library of AI prompts and agents.
Embrace internal enthusiasm: Whoop lets employees nominate tools they’re excited to trial, like Fireflies for note-taking and Zapier for automation.
If you’re wondering which tools to approve, here are my personal favorites:
As an employee, don’t be afraid to champion your favorite AI tools even if you’re not responsible for procurement.
2025-08-05 17:00:57
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Add the private feed to your podcast app at add.lennysreads.com
Peter Yang interviewed leaders at six of the most AI-forward companies—Zapier, Ramp, Duolingo, Shopify, Intercom, and Whoop—to uncover 25 real-world tactics for driving employee AI adoption. If your team is still struggling to get value from AI tools, this episode is packed with practical advice, internal playbooks, and strategies you can use right away.
In this episode, you’ll learn
The five steps to driving AI adoption at your company
Why vague AI-first mandates don’t work—and what to do instead
How to track and reward adoption, usage, and outcomes
How to cut through red tape and unblock company-wide access
How to turn AI power users into internal teachers
Which high-impact tasks top companies are automating first
What separates real AI adoption from flashy demo theater
References
2025-08-04 19:03:31
Why is this in your inbox? Because How I AI, hosted by Claire Vo, is part of the Lenny’s Podcast Network. Every Monday, we share a 30- to 45-minute episode with a new guest demoing a practical, impactful way they’ve learned to use AI in their work or life. No pontificating—just specific and actionable advice. Prefer to skip future episode drops? Unsubscribe from How I AI podcast notifications here.
Lovable—Build apps by simply chatting with AI
Persona—Trusted identity verification for any use case
Andrew Mason (founder of Groupon, now CEO of Descript) and Nabeel Hyatt (General Partner at Spark Capital) teamed up to open a physical board-game social club in Berkeley, with AI as their business partner. In this episode, they break down how they used Claude to generate a full business plan, model financials, plan the space layout, navigate Berkeley permitting, categorize hundreds of games using a custom Dewey Decimal–style system, and build an AI concierge that matches players with games via text. They also share how working on this side project helped rewire how they use AI in their day jobs—and why more people should use AI to build real-world things.
What you’ll learn:
1. How to use Claude Projects as your business copilot to create comprehensive business plans, financial projections, and space layouts
2. A workflow for categorizing hundreds of board games using an AI-generated “Dewey Decimal System” that makes game discovery intuitive
3. How they built an AI concierge service that matches players with games and coordinates group play sessions via text message
4. Why AI enables side projects that would otherwise be impossible due to time constraints and specialized knowledge requirements
5. A simple system for creating customer personas that inform your business model and event programming
6. How to use model context protocols (MCPs) to connect AI assistants to business tools like Airtable without complex coding
LinkedIn: https://www.linkedin.com/in/andrewmason/
LinkedIn: https://www.linkedin.com/in/nabeelhyatt/
ChatPRD: https://www.chatprd.ai/
Website: https://clairevo.com/
LinkedIn: https://www.linkedin.com/in/clairevo/
(00:00) Introduction to the board-game social club concept
(02:44) How AI made a challenging side project possible
(06:14) Using Claude as a business copilot for planning
(12:53) Developing customer personas with AI
(15:45) Using AI to determine business viability
(21:02) Navigating Berkeley real estate and permitting
(25:18) Building an AI concierge for game matchmaking
(28:10) Database design with Airtable for non-technical founders
(32:04) Creating a custom board-game categorization system
(36:20) Demo of the text-based AI concierge service
(40:38) Enabling experiences that wouldn’t exist without AI
(43:42) Lightning round and final thoughts
• Claude: https://claude.ai/
• Airtable: https://airtable.com/
• n8n: https://n8n.io/
• Twilio: https://www.twilio.com/
• Cursor: https://cursor.sh/
• Windsurf: https://www.windsurf.io/
• Python: https://www.python.org/
• Model context protocol (MCP): https://www.anthropic.com/news/model-context-protocol
• Tabletop Library: https://tabletoplibrary.com/
• Descript: https://www.descript.com/
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
2025-08-03 19:02:41
Great Question—Empower everyone to run great research
Vanta—Automate compliance. Simplify security.
Coda—The all-in-one collaborative workspace
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.
In this conversation, we discuss:
The reality of Brian Chesky in “founder mode”—the good, bad, and stressful
How Chip went from running 52 boutique hotels to becoming Airbnb’s in-house mentor in his 50s
The “mentor and intern” mindset: how to simultaneously teach others and stay curious like a beginner
Why AI might actually favor older workers (hint: human wisdom vs. artificial intelligence)
His framework for navigating midlife transitions and finding meaning after 40
Specific tactics for older professionals to thrive in tech companies
Surprising data that midlife is often the happiest time of life—and how to leverage your 40s, 50s, and beyond
Chip’s formula for managing anxiety and fear (and how to regain control when worry strikes)
• LinkedIn: https://www.linkedin.com/in/chipconleysf/
• Website: https://chipconley.com/
• Modern Elder Academy: https://www.meawisdom.com/
• Podcast: https://www.meawisdom.com/podcast/
(00:00) Introduction to Chip Conley
(04:30) Chip’s journey with Airbnb
(11:44) Insights on working with Brian Chesky
(18:27) Tactics to be effective when working with founders in founder mode
(21:08) The value of intergenerational collaboration
(27:03) Addressing ageism in tech
(31:18) Advice for thriving as an older individual in tech
(35:01) Advice for hiring managers
(42:37) Chip’s early career and founding Joie de Vivre
(44:12) A life-changing near-death experience
(47:51) The importance of company culture
(52:20) The Peak Model
(57:09) The Modern Elder Academy (MEA)
(01:00:30) The upside of aging
(01:06:43) Who MEA is for
(01:08:05) AI in daily life
(01:10:20) Lightning round and final thoughts
• Brian Chesky on LinkedIn: https://www.linkedin.com/in/brianchesky/
• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach
• Natalie Tucci on LinkedIn: https://www.linkedin.com/in/natalietuccishoff/
• Laura Modi on LinkedIn: https://www.linkedin.com/in/laurahughes6/
• How to build a cult-like brand | Laura Modi (Bobbie): https://www.lennysnewsletter.com/p/from-growth-to-slowth-the-making
• George Tenet: https://en.wikipedia.org/wiki/George_Tenet
• Joie de Vivre Hospitality: https://www.hyatt.com/jdv-by-hyatt/en-US
• Fest300: https://en.wikipedia.org/wiki/Fest300
• John Q. Smith on LinkedIn: https://www.linkedin.com/in/johnqsmith/
•Will A.I. Replace New Hires or Middle Managers?: https://www.nytimes.com/2025/07/07/business/ai-job-cuts.html
• Burning Man: https://burningman.org/
• Sheryl Sandberg on LinkedIn: https://www.linkedin.com/in/sheryl-sandberg-5126652/
• Bill Graham: https://en.wikipedia.org/wiki/Bill_Graham_(promoter)
• Maslow’s hierarchy: https://en.wikipedia.org/wiki/Maslow%27s_hierarchy_of_needs
• Measuring what makes life worthwhile: https://www.ted.com/talks/chip_conley_measuring_what_makes_life_worthwhile
• Jonathan Mildenhall on LinkedIn: https://www.linkedin.com/in/mildenhall/
• Becca Levy’s website: https://becca-levy.com/
• Kabuki Springs & Spa: https://kabukisprings.com/
• How positive age beliefs can support positive health outcomes with Becca Levy, PhD: https://www.ama-assn.org/delivering-care/population-care/how-positive-age-beliefs-can-support-positive-health-outcomes-becca
• The U-shape of Happiness Across the Life Course: Expanding the Discussion: https://pmc.ncbi.nlm.nih.gov/articles/PMC7529452/
• The Midlife Unraveling: https://brenebrown.com/articles/2018/05/24/the-midlife-unraveling/
• Four Seasons: https://www.fourseasons.com/
• Blue Zones: https://www.bluezones.com/
• The Esalen Institute: https://www.esalen.org/
• Wisdom Well blog: https://www.meawisdom.com/wisdom-well/
• Elizabeth Gilbert TED Talk: Your elusive creative genius: https://www.ted.com/talks/elizabeth_gilbert_your_elusive_creative_genius
• Ted Lasso on AppleTV+: https://tv.apple.com/us/show/ted-lasso/umc.cmc.vtoh0mn0xn7t3c643xqonfzy
• I’ll Push You: https://www.illpushyou.com/
• Vuori shorts: https://vuoriclothing.com/collections/shorts
• Fly Ranch: https://flyranch.burningman.org/
• Wisdom at Work: The Making of a Modern Elder: https://www.amazon.com/Wisdom-Work-Making-Modern-Elder/dp/0525572902
• Range: Why Generalists Triumph in a Specialized World: https://www.amazon.com/Range-Generalists-Triumph-Specialized-World/dp/0735214484
• Peak: How Great Companies Get Their Mojo from Maslow: https://www.amazon.com/Peak-Great-Companies-Their-Maslow/dp/0787988618
• Learning to Love Midlife: 12 Reasons Why Life Gets Better with Age: https://www.amazon.com/Learning-Love-Midlife-Reasons-Better/dp/0316567027
• Man’s Search for Meaning: https://www.amazon.com/Mans-Search-Meaning-Viktor-Frankl/dp/0807060100/
• Emotional Equations: Simple Steps for Creating Happiness + Success in Business + Life: https://www.amazon.com/Emotional-Equations-Creating-Happiness-Business/dp/1451607261/
• Big Magic: Creative Living Beyond Fear: https://www.amazon.com/Big-Magic-Creative-Living-Beyond/dp/1594634726
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.
2025-08-02 23:50:01
👋 Hello and welcome to this week’s edition of ✨ Community Wisdom ✨ a subscriber-only email, delivered every Saturday, highlighting the most helpful conversations in our members-only Slack community.
