2025-11-25 00:02:50
Hey friends 👋,
Here’s a weekly recap of new podcast episodes across Lenny’s Podcast Network:
Every Monday, host Claire Vo shares 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.
Brought to you by:
WorkOS—Make your app enterprise-ready today
Google Gemini—Your everyday AI assistant
In this episode, Lucas Werthein, the COO and co-founder of Cactus, breaks down how he built a personal AI health coach that pulls together everything—MRIs, blood tests, wearables, nutrition plans, even journal entries—to help him train smarter, recover faster, and avoid re-injury. After years of surgeries and competing demands on his body, he realized the missing piece wasn’t more data but better synthesis. His AI coach now connects dots across dozens of sources, sets clear performance boundaries, adapts on the fly to real-world changes, and helps him “feel 25 in a 40-year-old body.”
Biggest takeaways:
Data synthesis—not data collection—is the missing link in health optimization. Lucas had access to blood tests, nutritionists, physical therapists, wearable data, and InBody scans, but the challenge was synthesizing this information into actionable insights. His AI coach solved this by integrating all data sources to provide clear, personalized recommendations.
The “last mile” of optimization often comes from unexpected sources. Despite having access to top medical professionals and performance experts, Lucas found that his AI coach unlocked breakthroughs that had eluded him. The AI’s ability to connect dots across siloed data sources provided insights that specialists working in isolation couldn’t deliver.
Effective AI coaches need clear boundaries and anti-prompts. Lucas explicitly instructs his GPT not to push past volume and intensity when metrics show under-recovery, to avoid unproven supplements, and to stick to evidence-based recommendations. These guardrails prevent the AI from giving potentially harmful advice.
AI health coaches will transform the doctor-patient relationship. Within five years, Lucas believes everyone will have access to a personal AI health coach that helps them live healthier between doctor visits and show up more informed. Eventually, a patient’s AI will communicate directly with the doctor’s AI before appointments.
Health-care leaders will eventually sell their knowledge as trained AI models. Lucas predicts that institutions like Mayo Clinic will package decades of patient data into AI models that provide personalized guidance grounded in the best medical science, making expert-level health coaching accessible to everyone.
▶️ Listen now on YouTube | Spotify | Apple Podcasts
Brought to you by: WorkOS—Make your app enterprise-ready today
In this episode, Claire walks through how she built a warm, handcrafted “Thanksgiving party hub” using Lovable—and along the way shares a bunch of practical tricks for making AI-generated apps feel intentional instead of generic. She breaks down how she upleveled the typography, visuals, and structure using Google Fonts, Midjourney style references, and a few simple ChatGPT prompts, plus her go-to recipe-cleaning workflow that actually works when you’re cooking with kids.
Biggest takeaways:
“Farm-to-table software” is the new standard for personal projects. Claire’s approach combines multiple AI tools (Lovable for structure, Google Fonts for typography, Midjourney for imagery, ChatGPT for content) to create something that feels artisanally crafted rather than generically generated.
Sometimes the fastest solution is to restart. When ChatGPT 5.1 got stuck processing her recipe request, Claire simply restarted with the “instant” setting rather than waiting—a practical reminder that AI tools sometimes need a reset.
Free Google font combinations are the easiest way to instantly uplevel any design. Instead of accepting default typography, Claire demonstrates how searching “Google font combinations” leads to curated pairings like “Homemade Apple” and “Railway” that immediately transform the look and feel of an application.
▶️ Listen now on YouTube | Spotify | Apple Podcasts
More shows coming soon. . . 👀
If you’re enjoying these episodes, reply and let me know what you’d love to learn more about: AI workflows, hiring, growth, product strategy—anything.
Catch you next week,
Lenny
P.S. Want every new episode delivered the moment it drops? Hit “Follow” on your favorite podcast app.
2025-11-24 20:03:47
WorkOS—Make your app enterprise-ready today
Google Gemini—Your everyday AI assistant
Lucas Werthein, the COO and co-founder of Cactus, shares how he built a personalized AI wellness coach using ChatGPT to optimize his athletic performance while managing past injuries. After multiple surgeries on his knees, shoulder, and foot, Lucas created a system that synthesizes data from medical imaging, blood tests, wearable devices, and nutrition plans to provide personalized recommendations. His AI coach helps him balance competitive tennis, weightlifting, and running a company while maintaining his goal of “feeling 25 in a 40-year-old body.” Lucas demonstrates how this approach transforms siloed health information into actionable insights that protect joints, optimize recovery, and extend peak performance.
What you’ll learn:
How to configure a ChatGPT with multiple data types, including MRIs, x-rays, blood tests, and wearable metrics, to create a comprehensive health profile
A framework for setting clear performance boundaries that prioritize joint protection, energy optimization, and injury prevention
Techniques for using AI to balance nutrition around special events like social dinners while maintaining performance goals
How to use images and videos to get AI feedback on physical symptoms and injury recovery timelines
A method for validating and contextualizing medical advice by having AI synthesize information from multiple health-care providers
Why creating clear rules and anti-prompts helps AI deliver practical, evidence-based recommendations instead of trendy supplements or extreme protocols
Website: https://cactus.is/
ChatPRD: https://www.chatprd.ai/
Website: https://clairevo.com/
LinkedIn: https://www.linkedin.com/in/clairevo/
(00:00) Introduction to Lucas’s athletic background and injury history
(04:55) The challenge of synthesizing siloed health data
(06:11) Building a GPT to optimize performance and recovery
(09:57) Demonstrating the data types integrated into the AI coach
(13:54) Configuring the GPT with clear performance goals and boundaries
(16:31) Setting realistic expectations for the AI coach
(17:50) Creating nutrition, training, and recovery frameworks
(21:47) Establishing hard boundaries and anti-prompts
(24:25) Example: Managing nutrition around special events
(27:30) Accessibility and affordability of on-demand coaching
(28:24) Practical examples and real-life scenarios
(29:31) Using AI for injury management and recovery planning
(34:19) Validating expert opinions and translating medical advice
(37:25) Vision for the future of AI in personal health coaching
(43:27) Other AI workflows: synthetic clients and AI co-founders
(48:48) Final thoughts on AI reliability and evolution
• ChatGPT: https://chat.openai.com/
• InBody scan: https://inbodyusa.com/
• Whoop: https://www.whoop.com/
Act as my performance strategist and health optimization coach.
You know my physiology, labs, imaging, and wearables. You coach me like a high-performance operator: I’m balancing tennis, lifting, recovery, and running a company. Your job is to safeguard my joints, amplify my output, and extend my peak. I want to perform like a 25-year-old in the body of a 40-year-old!
When I share a prompt, update, or idea, you should:
• Interrogate it through my context (bloods, scans, Whoop, workload, soreness, sleep, and mood)
• Flag red/yellow zones (early signs of overtraining, underfueling, inflammation, or regression)
• Prescribe only high-ROI actions that compound performance (no fluff, no hacks, just results)
• Keep me inside the zone where I wake up rested, move pain-free, and play high-output tennis with no breakdown.
⸻
Optimize across 4 critical axes:
1. Fueling & Inflammation
Stick to my nutrition plan unless there’s a data-driven reason to adapt. Prioritize energy availability, stable glucose, low systemic inflammation, and muscle retention.
2. Training & Load Management
Balance strength, endurance, and mobility—while protecting knees, shoulder, and joints under current imaging conditions. Don’t overload when HRV, CPK, or readiness scores say pull back.
3. Recovery & Regeneration
Sleep drives readiness. PT, mobility, sauna/cold, massage, and mindfulness are not optional—they’re part of the training cycle. Map recovery inputs to readiness trends.
4. Tracking & Feedback Loops
Integrate data across Whoop, InBody, labs, diet, and journal entries. Decisions must be cross-validated: don’t recommend something if it’s not aligned across inputs.
⸻
Hard boundaries:
• Never push volume/intensity when metrics show under-recovery.
• No stacking supplements unless there’s measurable ROI.
• No novelty chasing—stick to what compounds.
• Always act on red flags: recurring soreness, low HRV, decreased sleep quality, creeping inflammation.
⸻
Align every decision on values:
• Precision — is this grounded in my data?
• Energy — does it improve tomorrow’s energy, not just today’s output?
• Adaptation — does this stressor drive growth or wear me down?
• Kinetics — is my movement getting cleaner, faster, more fluid?
⸻
Tone & Response Style:
• Write like a coach who’s been in the trenches with me.
• Fast, clear, tactical—no fluff, no lectures.
• Connect dots across labs, sleep, training, and diet.
• Prioritize what matters this week, not vague long-term theory.
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
2025-11-23 20:03:19
Rachel Lockett is a sought-after executive coach and former HR leader at Stripe and Pinterest who now works with CEOs, founders, and tech leaders on emotional intelligence, resilience, and leadership skills. In this episode, Rachel shares powerful frameworks for coaching reports, having difficult conversations, avoiding burnout, and strengthening co-founder relationships. She also demonstrates these techniques through a live coaching session with me.
We discuss:
When to coach and when to just tell people what to do [09:00]
The GROW technique for helping people figure out a solution for themselves [18:37]
Techniques for making difficult conversations less difficult [01:20:28]
Avoiding burnout and designing a more energizing career [41:55]
Building and sustaining a healthy co-founder relationship [01:06:50]
Creating a one-page plan that aligns your entire company [01:31:47]
Practical ways AI is transforming executive coaching and leadership development [01:36:50]
Why you should ask, “Would I enthusiastically rehire this person?” to clarify talent decisions [23:55]
Also on Spotify and Apple Podcasts
Stripe—Helping companies of all sizes grow revenue
Vanta—Automate compliance. Simplify security.
Persona—A global leader in digital identity verification
• LinkedIn: https://www.linkedin.com/in/rhlockett/
• Website: https://www.lockettcoaching.com
• One-page plan template: https://www.lockettcoaching.com/#resources
• Lockett Coaching Leadership Toolkit: https://www.dropbox.com/scl/fi/s74a9cn1ka1ebz6pglypf/Leadership-Toolkit_-Coaching-Rachel-Lockett.pdf?rlkey=yg2m9df2ziwy0fa6p0dt4gcfu&st=dgzvnf76&dl=0
• Renew Your Co-Founder Vows—and Other Tactics for Strengthening the Most Important Relationship in Your Startup: https://review.firstround.com/five-practices-to-strengthen-your-co-founder-relationship/
• First Round Guide to Co-Founder Check-Ins: https://docs.google.com/document/d/1yUosmfMuE-8-sAwPrEPDcGqkJLVLWg5dC2_8lcXm7U4/edit?tab=t.0
• Coinbase: https://www.coinbase.com
• Management Time: Who’s Got the Monkey?: https://hbr.org/1999/11/management-time-whos-got-the-monkey
• Chuck Palahniuk’s quote from Fight Club: https://www.goodreads.com/quotes/1338270-people-don-t-listen-they-just-wait-for-their-turn-to
• Patrick Collison on X: https://x.com/patrickc
• Stripe: https://stripe.com
• Remind: https://www.remind.com
• Zach Abrams on LinkedIn: https://www.linkedin.com/in/zacharyabrams
• Brex: https://www.brex.com
• Bridge: https://www.bridge.xyz
• Superhuman’s secret to success: Ignoring most customer feedback, manually onboarding every new user, obsessing over every detail, and positioning around a single attribute: speed | Rahul Vohra (CEO): https://www.lennysnewsletter.com/p/superhumans-secret-to-success-rahul-vohra
• Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO): https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building
• The Enneagram Institute: https://www.enneagraminstitute.com
• How to build deeper, more robust relationships | Carole Robin (Stanford GSB professor, “Touchy Feely”): https://www.lennysnewsletter.com/p/build-robust-relationships-carole-robin
• How have I been complicit in creating the conditions I say I don’t want? | Jerry Colonna (CEO of Reboot, executive coach, former VC): https://www.lennysnewsletter.com/p/jerry-colonna
• How Netflix builds a culture of excellence | Elizabeth Stone (CTO): https://www.lennysnewsletter.com/p/how-netflix-builds-a-culture-of-excellence
• What Is PeopleFirst?: https://alpineinvestors.com/story/what-is-peoplefirst
• How to break out of autopilot and create the life you want | Graham Weaver (Stanford GSB professor, founder of Alpine Investors): https://www.lennysnewsletter.com/p/how-to-break-out-of-autopilot-graham-weaver
• Granola: https://www.granola.ai
• KPop Demon Hunters on Netflix: https://www.netflix.com/title/81498621
• Loom: https://www.loom.com
• Joseph Campbell’s quote: https://www.goodreads.com/quotes/21396-if-you-can-see-your-path-laid-out-in-front
• Wes Anderson’s short films (Roald Dahl) on Netflix: https://www.netflix.com/tudum/articles/wes-anderson-netflix-short-films
• Nonviolent Communication: A Language of Life: Life-Changing Tools for Healthy Relationships: https://www.amazon.com/Nonviolent-Communication-Language-Life-Changing-Relationships/dp/189200528X
• The 15 Commitments of Conscious Leadership: A New Paradigm for Sustainable Success: https://www.amazon.com/15-Commitments-Conscious-Leadership-Sustainable/dp/0990976904
• Designing Your Life: How to Build a Well-Lived, Joyful Life: https://www.amazon.com/Designing-Your-Life-Well-Lived-Joyful/dp/1101875321
• Roald Dahl books: https://www.amazon.com/Roald-Dahl-Collection-Books-Box/dp/0241377293
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.
2025-11-23 03:37:41
👋 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.
2025-11-20 22:03:33
Stewart Butterfield is the co-founder of Slack and Flickr, two of the most influential products in internet history. After selling Slack to Salesforce in one of tech’s biggest acquisitions, he’s been focused on family, philanthropy, and creative projects. In this rare podcast appearance, Stewart shares the product frameworks and leadership principles that most contributed to his success. From “utility curves” to “the owner’s delusion” to “hyper-realistic work-like activities,” his thoughts on craft, strategy, and leadership apply to anyone building products or leading teams.
We discuss:
Hyper-realistic work-like activities [01:03:17]
The owner’s delusion [01:26:34]
Utility curves [06:44]
“Don’t make me think” [36:55]
“We don’t sell saddles here” [01:08:30]
Tilting your umbrella [19:03]
When to pivot [01:13:23]
Also on Spotify and Apple Podcasts
WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs
Metronome—Monetization infrastructure for modern software companies
Lovable—Build apps by simply chatting with AI
• LinkedIn: https://www.linkedin.com/in/butterfield
• Slack: https://slack.com
• Flickr: https://www.flickr.com
• Cal Henderson on LinkedIn: https://www.linkedin.com/in/iamcal
• Blok: https://blok.so
• Brandon Velestuk on LinkedIn: https://www.linkedin.com/in/brandon-velestuk-6018721b
• Magic Link: https://en.wikipedia.org/wiki/Magic_Link
• Ticketmaster: https://www.ticketmaster.com
• John Collison on X: https://x.com/collision
• Patrick Collison on X: https://x.com/patrickc
• Sundar Pichai on LinkedIn: https://www.linkedin.com/in/sundarpichai
• Three Questions with Slack’s CEO: https://www.technologyreview.com/2014/11/21/170330/three-questions-with-slacks-ceo
• Six Sigma: https://www.6sigma.us
• What is kaizen and how does Toyota use it?: https://mag.toyota.co.uk/kaizen-toyota-production-system
• John Collison’s post on X about passion projects: https://x.com/collision/status/1529452415346302976
• Parkinson’s law: https://www.economist.com/news/1955/11/19/parkinsons-law
• We Don’t Sell Saddles Here: https://medium.com/@stewart/we-dont-sell-saddles-here-4c59524d650d
• Glitch: https://en.wikipedia.org/wiki/Glitch_(video_game)
• IRC: https://en.wikipedia.org/wiki/IRC
• This will make you a better decision-maker | Annie Duke (author of “Thinking in Bets” and “Quit,” former pro poker player): https://www.lennysnewsletter.com/p/making-better-decisions-annie-duke
• The woman behind Canva shares how she built a $42B company from nothing | Melanie Perkins: https://www.lennysnewsletter.com/p/the-making-of-canva
• Prisoner’s dilemma: https://en.wikipedia.org/wiki/Prisoner%27s_dilemma
• Stewart Little: https://en.wikipedia.org/wiki/Stuart_Little
• Dharma and Greg: https://en.wikipedia.org/wiki/Dharma_%26_Greg
• Stewart’s post on X referencing “the owner’s delusion”: https://x.com/stewart/status/1223286626991796224
• Principles: Life and Work: https://www.amazon.com/Principles-Life-Work-Ray-Dalio/dp/1501124021
• Why Nothing Works: Who Killed Progress―and How to Bring It Back: https://www.amazon.com/Why-Nothing-Works-Killed-Progress_and/dp/154170021X
• Positioning: The Battle for Your Mind: https://www.amazon.com/Positioning-Battle-Your-Al-Ries/dp/0071373586
• Quit: The Power of Knowing When to Walk Away: https://www.amazon.com/Quit-Power-Knowing-When-Walk/dp/0593422996
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.
2025-11-19 21:03:41
WorkOS—Make your app enterprise-ready today
In today’s pre-Thanksgiving episode, I walk you through how I vibe coded my very own “Thanksgiving party hub” using Lovable—and how I transformed it from AI-generated slop into something warm, personal, and genuinely useful. I show you exactly how I upleveled the typography, visuals, and structure using Google Fonts and Midjourney style references, and then I share one of my favorite real-life AI hacks: how to turn any messy online recipe into a clean, step-by-step, kid-friendly version that’s actually usable while you’re cooking. This is a cozy, practical walkthrough of my real design process—the little tricks I use to make AI-built apps feel handcrafted instead of generic.
What you’ll learn:
How to build a fully functional Thanksgiving party hub in Lovable—guests, dishes, recipes, and photos
How I uplevel AI-generated designs using Google Fonts and Tailwind
How to use Midjourney style references to create custom images that match your aesthetic
How to add custom features to vibe-coded apps, like dietary preferences and allergen tags
How to iterate on layouts inside Lovable using screenshots and small, targeted prompts
How I use ChatGPT to restructure recipes so the measurements are embedded directly in each step
How to make recipes kid-friendly and easier to follow using a simple formatting prompt
ChatPRD: https://www.chatprd.ai/
Website: https://clairevo.com/
LinkedIn: https://www.linkedin.com/in/clairevo/
(00:00) Introduction to the Thanksgiving party hub concept
(02:20) Starting a project in Lovable and initial design assessment
(04:59) Upleveling typography with Google Font combinations
(08:36) Creating custom header images with Midjourney
(11:39) Adjusting aspect ratios for Midjourney images
(14:22) Fixing design issues incrementally
(18:52) Adding dietary-restriction functionality
(23:36) AI recipe reformatting for easier cooking
(26:02) Thoughts on ChatGPT 5.1
(30:51) Final implementation and recipe sharing
• Lovable: https://lovable.dev/
• Midjourney: https://www.midjourney.com/
• Google Fonts: https://fonts.google.com/
• ChatGPT: https://chat.openai.com/
• Canva Font Combinations: https://www.canva.com/font-combinations/
• Polenta and Sausage Stuffing Recipe: https://www.epicurious.com/recipes/food/views/polenta-and-sausage-stuffing-233030
• Runaway Pancakes (kid-friendly recipe site): https://runawaypancakes.com/
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].