Carole Robin spent over 20 years teaching the Stanford Graduate School of Business course Interpersonal Dynamics, affectionately known as “Touchy Feely.” After leaving Stanford, she founded a nonprofit called Leaders in Tech, which applies the Touchy Feely principles to help Silicon Valley executives build their leadership and interpersonal skills. Carole co-authored the popular book Connect: Building Exceptional Relationships with Family, Friends, and Colleagues, which shares key insights from her decades of teaching these courses. In our conversation, we discuss:

• The benefits of building robust relationships, in life and work

• The 15% rule, and how it will help you build better relationships

• The power of vulnerability

• Examples of how to practice vulnerability

• Why mental models you build early in life hold you back later

• The “three realities” and “the net”

• The art of inquiry

• Practical tips for avoiding defensiveness when getting feedback

• The impact of long Covid on Carole’s life

—

Brought to you by:

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—

Find the transcript at: https://www.lennysnewsletter.com/p/build-robust-relationships-carole-robin

—

Where to find Carole Robin:

• LinkedIn: https://www.linkedin.com/in/carole-robin/

• Email: [email protected]

—

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) Carole’s background

(05:17) The importance of building robust relationships

(10:20) The “Touchy Feely” course at Stanford

(13:29) An example of the in-class experience

(17:19) Leaders in Tech: developing interpersonal competence

(21:36) Progressive disclosure and the 15% rule

(24:28) Appropriate disclosure

(26:52) The power of vulnerability

(34:57) Admitting mistakes and sharing feelings

(37:08) Understanding mental models

(42:57) The “three realities” framework

(53:52) The power of feedback and personal change

(58:47) The art of inquiry

(01:03:27) How to get better at giving feedback

(01:07:47) Exercises and continued learning

(01:10:49) “Advice hinders relationships”

(01:16:49) Failure corner: AFOG

(01:20:30) Takeaways

(01:21:51) Lessons from long Covid

—

Referenced:

• How to Build Better Relationships: https://www.gsb.stanford.edu/insights/how-build-better-relationships

• Connect: Building Exceptional Relationships with Family, Friends, and Colleagues: https://www.amazon.com/Connect-Building-Exceptional-Relationships-Colleagues-ebook/dp/B0894279WZ

• Leaders in Tech: https://leadersintech.org/

• Leaders in Tech Fellows: https://leadersintech.org/learnaboutfellows

• Steve Jobs: https://www.forbes.com/profile/steve-jobs/

• Sheryl Sandberg on X: https://twitter.com/sherylsandberg

• Ursula Burns: https://www.forbes.com/profile/ursula-burns/

• Application for Leaders in Tech: https://leadersintech.org/programs-and-applications

• Vygotsky’s Zone of Proximal Development and Scaffolding Theory: https://www.simplypsychology.org/zone-of-proximal-development.html

• The Best Leaders Aren’t Afraid to Be Vulnerable: https://hbr.org/2022/07/the-best-leaders-arent-afraid-of-being-vulnerable

• The Surprising Benefits of Admitting Mistakes: 5 Ways to Build Intellectual Humility: https://www.forbes.com/sites/tracybrower/2021/12/29/the-surprising-benefits-of-admitting-mistakes-5-ways-to-build-intellectual-humility/

• How to Build Conflict Skills—The Pinch/Crunch Model: https://www.forbes.com/sites/hannahart/2023/12/15/how-to-build-conflict-skills-the-pinchcrunch-model/

• Slides mentioned (The Three Realities Framework | The 15% Rule | Feedback Guidelines): https://pen-name.notion.site/Carole-Robin-4-25-5d47d38a620e4636966d31f4bf3c7d00?pvs=4

• Mindset: The New Psychology of Success: https://www.amazon.com/Mindset-Psychology-Carol-S-Dweck/dp/0345472322

• Management Time: Who’s Got the Monkey?: https://hbr.org/1999/11/management-time-whos-got-the-monkey

• Long COVID: major findings, mechanisms and recommendations: https://www.nature.com/articles/s41579-022-00846-2

• Leadership, acceptance, and self-management: my journey with long COVID: https://www.linkedin.com/pulse/leadership-acceptance-self-management-my-journey-long-carole-robin/

—

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.

Mihika Kapoor is a design-engineer-PM hybrid at Figma, where she was an early PM on FigJam and is now spearheading development on a new product at the company that’s coming out this June. She’s known as the go-to person at Figma for leading new 0-to-1 products, and, as you’ll hear in our conversation, beloved by everyone she works with. Her background includes founding Design Nation, a national nonprofit focused on democratizing design education for undergraduates; spearheading product launches at Meta; and community building within the NYC AI startup scene. In our conversation, we discuss:

• How to effectively take ideas from 0 to 1 at larger companies

• How to craft a compelling vision

• The importance of vulnerability and feedback

• The role of intuition and product sense in making decisions

• How to practically communicate your vision

• How to balance collaboration and strong opinions

• Advice for building a strong team culture

• Pivoting with grace and enthusiasm

• The current AI revolution and its impact on PM

—

Brought to you by:

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• Vanta—Automate compliance. Simplify security

—

Find the transcript at: https://www.lennysnewsletter.com/p/vision-conviction-hype-mihika-kapoor

—

Where to find Mihika Kapoor:

• X: https://twitter.com/mihikapoor

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

—

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) Mihika’s background

(04:29) Core attributes of great product managers

(07:34) Crafting a compelling vision

(12:12) The vision behind FigJam 

(18:25) Delivering a vision without design or engineering skills

(21:52) Creating momentum

(26:36) The importance of strong conviction

(27:45) Direct communication

(32:48) Building hype

(42:20) Immersing yourself in user insights

(47:16) Operationalizing user insights  

(50:33) Caring deeply about what you build

(54:01) Finding passion in your work

(57:00) Building a strong culture

(01:07:07) Pivoting with grace and enthusiasm

(01:11:48) Design Nation

(01:13:15) Mihika’s weaknesses

(01:16:07) Building new products at larger companies

(01:20:50) Coming up with a great idea

(01:22:49) The key to going from 0 to 1

(01:26:47) Spreading the idea across the company

(01:29:15) Closing thoughts

(01:32:11) Lightning round

—

Referenced:

• Figma: https://www.figma.com/

• Sho Kuwamoto on LinkedIn: https://www.linkedin.com/in/shokuwamoto/

• The Medici Effect: What Elephants and Epidemics Can Teach Us About Innovation: https://www.amazon.com/Medici-Effect-Preface-Discussion-Guide/dp/1633692949

• FigJam: https://www.figma.com/figjam/

• Cognition: https://www.cognition-labs.com/

• Devin: https://www.cognition-labs.com/introducing-devin

• David Hoang on LinkedIn: https://www.linkedin.com/in/dhoang2/

• Replit: https://replit.com/

• The Making of Maker Week at Figma: https://www.figma.com/blog/the-making-of-maker-week/

• Yuhki Yamashita on LinkedIn: https://www.linkedin.com/in/yuhki/

• Jeff Bezos’ Simple Decision-Making Framework Will Give You Clarity, Conviction, and Courage: https://medium.com/illumination/jeff-bezos-simple-decision-making-framework-will-give-you-clarity-conviction-and-courage-adf8d0183625

• Alice Ching on LinkedIn: https://www.linkedin.com/in/aliceching/

• Karl Jiang on LinkedIn: https://www.linkedin.com/in/karl-jiang-4a07424/

• Kris Rasmussen on LinkedIn: https://www.linkedin.com/in/kristopherrasmussen/

• Config: https://config.figma.com/

• Dev Mode: https://www.figma.com/dev-mode/

• Asana: https://asana.com/

• Julie Zhuo on LinkedIn: https://www.linkedin.com/in/julie-zhuo/

• StrengthsFinder test: https://www.gyfted.me/personality-quiz/strengthsfinder-test-free

• Dylan Field on LinkedIn: https://www.linkedin.com/in/dylanfield/

• Vishal Shah on LinkedIn: https://www.linkedin.com/in/vishalnshah/

• Design Disruptors: https://www.invisionapp.com/films/design-disruptors

• Daniel Burka on LinkedIn: https://www.linkedin.com/in/dburka/

• Jamie Myrold on LinkedIn: https://www.linkedin.com/in/jamiemyrold/

• Design Nation: https://dn.businesstoday.org/

• Stuart Weitzman on X: https://twitter.com/StuartWeitzman

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

• Building a long and meaningful career | Nikhyl Singhal (Meta, Google): https://www.lennyspodcast.com/building-a-long-and-meaningful-career-nikhyl-singhal-meta-google/

• Jambot: https://www.figma.com/community/widget/1274481464484630971/jambot

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

• Harry Potter series: https://www.amazon.com/Harry-Potter-Paperback-Box-Books/dp/0545162076

• Pachinko: https://www.amazon.com/Pachinko-National-Book-Award-Finalist/dp/1455563927/

• Creativity, Inc.: Overcoming the Unseen Forces That Stand in the Way of True Inspiration: https://www.amazon.com/Creativity-Inc-Expanded-Overcoming-Inspiration/dp/0593594649

• The Overstory: https://www.amazon.com/Overstory-Novel-Richard-Powers/dp/039335668X

• Severance on AppleTV+: https://tv.apple.com/us/show/severance/umc.cmc.1srk2goyh2q2zdxcx605w8vtx

• Dune on Max: https://www.max.com/movies/dune/e7dc7b3a-a494-4ef1-8107-f4308aa6bbf7

• Dune: Part 2: https://www.dunemovie.com/

• Arc browser: https://arc.net/

• Pika: https://pika.art/home

• The power of recognition: Why you should celebrate your employees | Josh Miller: https://www.lennyspodcast.com/videos/the-power-of-recognition-why-you-should-celebrate-your-employees-josh-miller/

—

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.

Dalton Caldwell is Managing Director and Group Partner at Y Combinator. Prior to YC, he was the co-founder and CEO of imeem (acquired by MySpace in 2009) and the co-founder and CEO of App.net. During his time at YC, he’s advised more than 35 YC unicorns, including DoorDash, Amplitude, Webflow, and Retool, and has worked across 21 different YC batches. He’s also racked up more than 6,500 office hours with founders. In our conversation, we discuss:

• Why founders need to adopt the mindset “Just don’t die”

• The most common reason startups fail

• When to pivot, and characteristics of a good pivot

• The concept of “tar pit ideas” and examples of bad startup ideas

• Why investors say no to startups

• The importance of market size in investment decisions

• The pitfalls of founders over-delegating

• Effective ways to talk to customers

• 20 ideas Dalton is looking to fund

—

Brought to you by:

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• Coda—The all-in-one collaborative workspace

—

Find the transcript at: https://www.lennysnewsletter.com/p/lessons-from-1000-yc-startups

—

Where to find Dalton Caldwell:

• X: https://twitter.com/daltonc

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

—

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) Dalton’s background

(04:41) The value of simple advice

(07:04) Dalton’s advice: “Just don’t die”

(08:39) Knowing when to stop

(11:45) Deciding to pivot

(14:26) Characteristics of a good pivot

(17:53) Knowing when to pivot

(19:03) Zip’s journey and finding a market

(21:22) Why Dalton says to “Move towards the mountains and the desert”

(23:45) Tar pit ideas

(26:49) Understanding why investors say no

(29:14) The importance of market size

(32:16) Avoiding over-delegation and hiring senior people too early

(36:43) Why startups fail

(40:30) Effectively talking to customers

(45:17) Examples of startups hustling to talk to customers

(48:01) Patterns of successful startups

(52:05) YC’s Request for Startups

(55:37) Early days of Silicon Valley

(01:05:33) Contrarian corner: growth hacking for early startups

(01:09:28) Failure corner

(01:11:15) Closing thoughts

(01:12:22) Lightning round

—

Referenced:

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

• Tiger Woods’s website: https://tigerwoods.com/

• Co-Founder Mistakes That Kill Companies & How to Avoid Them: https://www.youtube.com/watch?v=dlfjs_eEEzs

• Daniel Alberson’s LinkedIn post about Y Combinator: https://www.linkedin.com/posts/alberson_i-left-my-dream-job-as-a-product-manager-activity-7089677882431533056-jJ9H

• Companies in Y Combinator W17 Batch: https://www.ycdb.co/batch/w17

• Brex: https://www.brex.com/

• Retool: https://retool.com/

• Segment: https://segment.com/

• Mixpanel: https://mixpanel.com/

• Whatnot: https://www.whatnot.com/

• Andreessen Horowitz: https://a16z.com/

• Airbnb’s CEO says a $40 cereal box changed the course of the multibillion-dollar company: https://fortune.com/2023/04/19/airbnb-ceo-cereal-box-investors-changed-everything-billion-dollar-company/

• Rujul Zaparde on LinkedIn: https://www.linkedin.com/in/rujulz/

• Zip: https://ziphq.com/

• Lu Cheng on LinkedIn: https://www.linkedin.com/in/lu-cheng-973b7830/

• Avoid these tempting startup tar pit ideas: https://www.ycombinator.com/library/Ij-avoid-these-tempting-startup-tarpit-ideas

• Airbnb acquires Localmind to create crowdsourced advice about neighborhoods: https://skift.com/2012/12/13/airbnb-acquires-localmind-to-create-crowdsourced-advice-about-neighborhoods/

• Foursquare: https://foursquare.com/

• Razorpay: https://razorpay.com/

• Total Addressable Market: https://www.productplan.com/glossary/total-addressable-market/

• Lenny Bogdonoff on LinkedIn: https://www.linkedin.com/in/rememberlenny/

• Milk Video: https://milkvideo.com/

• Lessons from working with 600+ YC startups | Gustaf Alströmer (Y Combinator, Airbnb): https://www.lennyspodcast.com/lessons-from-working-with-600-yc-startups-gustaf-alstromer-y-combinator-airbnb/

• How the most successful B2B startups came up with their original idea: https://www.lennysnewsletter.com/p/how-the-most-successful-b2b-startups

• Collison installation: https://news.ycombinator.com/item?id=18400504

• Stripe: https://stripe.com/

• Patrick Collison on LinkedIn: https://www.linkedin.com/in/patrickcollison/

• John Collison on LinkedIn: https://www.linkedin.com/in/johnbcollison/

• Tony Xu on LinkedIn: https://www.linkedin.com/in/xutony/

• Grant LaFontaine on LinkedIn: https://www.linkedin.com/in/grantlafontaine/

• Ryan Petersen on LinkedIn: https://www.linkedin.com/in/rpetersen/

• Lessons on building product sense, navigating AI, optimizing the first mile, and making it through the messy middle | Scott Belsky (Adobe, Behance): https://www.lennyspodcast.com/lessons-on-building-product-sense-navigating-ai-optimizing-the-first-mile-and-making-it-through-t/

• YC’s latest Request for Startups: https://www.ycombinator.com/blog/ycs-latest-request-for-startups

• ERPs: https://www.ycombinator.com/rfs#new-enterprise-resource-planning-software

• Commercial open source companies: https://www.ycombinator.com/rfs#commercial-open-source-companies

• New space companies: https://www.ycombinator.com/rfs#new-space-companies

• A way to end cancer: https://www.ycombinator.com/rfs#a-way-to-end-cancer

• Spatial computing: https://www.ycombinator.com/rfs#spatial-computing

• New defense technology: https://www.ycombinator.com/rfs#new-defense-technology

• Bringing manufacturing back to America: https://www.ycombinator.com/rfs#bring-manufacturing-back-to-america

• Better enterprise glue: https://www.ycombinator.com/rfs#better-enterprise-glue

• Small fine-tuned models, as an alternative to giant generic ones: https://www.ycombinator.com/rfs#small-finetuned-models-as-an-alternative-to-giant-generic-ones

• Reid Hoffman on LinkedIn: https://www.linkedin.com/in/reidhoffman/

• Sam Altman on X: https://twitter.com/sama

• Sean Parker on LinkedIn: https://www.linkedin.com/in/parkersean/

• Owen Van Natta on LinkedIn: https://www.linkedin.com/in/owen-van-natta-444a7/

• Marc Andreessen on X: https://twitter.com/pmarca

• Picplz 1, Instagram 0 as VC firm Andreessen Horowitz chooses photo app rival: https://www.reuters.com/article/idUS2587232395/

• Gustaf Alstromer—How to Get Users and Grow: https://www.youtube.com/watch?v=T9ikpoF2GH0

• Getting to Yes: Negotiating Agreement Without Giving In: https://www.amazon.com/Getting-Yes-Negotiating-Agreement-Without/dp/0143118757

• Founding Sales: The Early Stage Go-to-Market Handbook: https://www.amazon.com/Founding-Sales-Go-Market-Handbook-ebook/dp/B08PMK17Z1

• Founder-led sales | Pete Kazanjy (Founding Sales, Atrium): https://www.lennyspodcast.com/founder-led-sales-pete-kazanjy-founding-sales-atrium/

• The Sopranos on HBO: https://www.hbo.com/the-sopranos

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

• Columbo on Prime Video: https://www.amazon.com/Columbo-Season-1/dp/B008SA89HA

• Oura ring: https://ouraring.com/

• Apple watch: https://www.apple.com/watch/

• SiPhox: https://siphoxhealth.com/

• Dalton & Michael on YouTube: https://www.youtube.com/playlist?list=PLQ-uHSnFig5Nd98Sc9I-kkc0ZWe8peRMC

• How Future Billionaires Get Sh*t Done: https://www.youtube.com/watch?v=ephzgxgOjR0

• The Student’s Guide to Becoming a Successful Startup Founder: https://www.youtube.com/watch?v=O5KCB2p6SB8

—

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 DeSanto is the chief product officer of GitLab, which is the largest remote-only company in the world. They share many of their team meetings on YouTube, and they’ve grown from being an open-source code management product competing with GitHub to a multi-product platform that covers security, compliance, continuous integration, project management, and deployment tools, many of which are infused with AI magic. In our conversation, we discuss:

• How GitLab operationalizes transparency

• The philosophy behind recording and sharing team meetings on YouTube

• Their extensive public employee handbook

• GitLab’s core value of having “short toes”

• Challenges and advice for doing remote work well

• Strategies for ensuring effective communication in a remote work environment

• GitLab’s breadth-over-depth strategy

• The company’s unique approach to AI

• The value of using humor in high-stakes conversations

—

Brought to you by:

• Orb—The flexible billing engine for modern pricing

• Eppo—Run reliable, impactful experiments

• Paragon—Ship every SaaS integration your customers want

—

Find the transcript at: https://www.lennysnewsletter.com/p/the-gitlab-way

—

Where to find David DeSanto:

• X: https://twitter.com/david_desanto

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

• Threads: https://www.threads.net/@david.the.beard

—

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) David’s background

(04:20) Maintaining an epic beard

(05:29) Why GitLab publicly shares team meetings

(09:49) The GitLab Handbook

(11:30) GitLab’s issue tracker

(14:29) How to successfully build a culture of transparency

(18:11) Benefits of operating with transparency

(19:55) The value of building in public

(21:53) How GitLab implements their core value of kindness

(25:16) What it means to have “short toes”

(27:41) Other core values

(32:16) Common reasons for not fitting in at GitLab

(34:42) Advice for remote teams

(42:04) Advice for getting into product

(43:52) Advice for PMs who are struggling in a remote world

(48:25) Specific tools that help with remote work

(53:13) Time zones and remote work

(57:18) Breadth-over-depth strategy

(01:04:14) AI at GitLab

(01:13:11) GitLab’s products and solutions

(01:14:54) Lightning round

—

Referenced:

• GitLab: https://about.gitlab.com/

• UX Showcase—David DeSanto introduction to UX team and AMA: https://www.youtube.com/watch?v=fEdsmnVKNj4

• The GitLab Handbook: https://handbook.gitlab.com/

• Sid Sijbrandij on LinkedIn: https://www.linkedin.com/in/sijbrandij/

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

• GitLab issues: https://docs.gitlab.com/ee/user/project/issues/

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

• GitLab values: https://handbook.gitlab.com/handbook/values

• GitLab organizational structure: https://handbook.gitlab.com/handbook/company/structure

• GitLab direction: https://about.gitlab.com/direction/

• Dogfooding: A simple practice to help you build better products: https://medium.com/agileinsider/dogfooding-a-simple-practice-to-help-you-build-better-products-b5954af4d5f7

• The ultimate guide to adding a PLG motion | Hila Qu (Reforge, GitLab): https://www.lennysnewsletter.com/p/the-ultimate-guide-to-adding-a-plg

• 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

• HubSpot: https://www.hubspot.com/

• Crossing the Chasm: Marketing and Selling Disruptive Products to Mainstream Customers: https://www.amazon.com/Crossing-Chasm-3rd-Disruptive-Mainstream/dp/0062292986

• Geoffrey Moore on finding your beachhead, crossing the chasm, and dominating a market: https://www.lennyspodcast.com/geoffrey-moore-on-finding-your-beachhead-crossing-the-chasm-and-dominating-a-market/

• Open-core model: https://en.wikipedia.org/wiki/Open-core_model

• GitLab Duo: https://about.gitlab.com/gitlab-duo/

• GitLab Docs: https://docs.gitlab.com/

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

• GitLab Acquires UnReview to Expand Its DevOps Platform with Machine Learning Capabilities: https://about.gitlab.com/press/releases/2021-06-02-gitlab-acquires-unreview-machine-learning-capabilities/

• Essentialism: The Disciplined Pursuit of Less: https://www.amazon.com/Essentialism-Disciplined-Pursuit-Greg-McKeown/dp/0804137382

• The Mission Critical Core/Context Model for Product Managers: https://secretpmhandbook.com/the-mission-critical-corecontext-model-for-product-managers/

• The Devil’s Hour on AppleTV+: https://tv.apple.com/us/show/the-devils-hour/umc.cmc.3zw4tyzd4lvor5mwhujms63x3

• Glass Onion: A Knives Out Mystery on Netflix: https://www.netflix.com/title/81458416

• Taylor Swift’s The Eras Tour on Prime Video: https://www.amazon.com/TAYLOR-SWIFT-ERAS-EXTENDED-VERSION/dp/B0CP99SN2B

• The STAR method: https://capd.mit.edu/resources/the-star-method-for-behavioral-interviews/

• Artifact News: https://artifact.news/

• Superhuman: https://superhuman.com/

• Arc browser: https://arc.net/

• An inside look at how The Browser Company builds product: https://www.lennysnewsletter.com/p/competing-with-giants-an-inside-look

—

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.

Todd Jackson is a Partner at First Round Capital. Before moving into venture capital, he played a crucial role as VP of Product and Design at Dropbox, guiding the company until its IPO in 2018. Prior to Dropbox, Todd led product management for Twitter’s Content and Discovery teams after selling his startup, Cover, to Twitter in 2014. Before Cover, Todd oversaw product development for Facebook’s Newsfeed, Photos, and Groups. He kickstarted his career at Google as an associate product manager and eventually led product for Gmail, witnessing its growth from beta to 200 million users. In our conversation, we discuss:

• Why product-market fit (PMF) matters

• First Round Capital’s four-part PMF framework

• Level one: Nascent product-market fit

• Level two: Developing product-market fit

• Level three: Strong product-market fit

• Level four: Extreme product-market fit

• Examples of companies at each level

• How to know if you’re stuck at a level, and how to get unstuck

• What to change if you’re stuck: persona, problem, promise, and product

• The goals and challenges at each stage

—

Brought to you by:

• WorkOS—The modern API for auth and user identity

• Eppo—Run reliable, impactful experiments

• CommandBar—AI-powered user assistance for modern products and impatient users

—

Find the full transcript at: https://www.lennysnewsletter.com/p/a-framework-for-finding-product-market

—

Where to find Todd Jackson:

• X: https://twitter.com/tjack

• LinkedIn: https://www.linkedin.com/in/toddj0/

—

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) Todd’s background

(06:07) First Round Capital’s PMF framework

(09:07) Why product-market fit is so important

(11:02) Who can benefit from this framework

(12:55) The product-market fit method

(16:54) Broad overview of the framework

(21:35) Level one: nascent product-market fit

(33:16) The four P’s

(39:13) Level two: developing product-market fit

(49:13) Signs you’re stuck at level two, and what to do

(55:12) Level three: strong product-market fit

(01:00:17) Signs you’re stuck at level three, and what to do

(01:02:22) Level four: extreme product-market fit

(01:06:55) Rough timelines for each level

(01:11:18) A quick recap of the framework

(01:12:15) Diving deeper on the four P’s: what to do if you’re stuck

(01:13:56) Dollar-driven discovery

(01:25:11) Apply for the product-market-fit method program

—

Referenced:

• First Round: https://firstround.com/

• Twitter Acquires Cover: https://www.vox.com/2014/4/7/11625332/twitter-acquires-cover-an-android-mobile-startup

• Dropbox: https://www.dropbox.com/

• Rahul Vohra on LinkedIn: https://www.linkedin.com/in/rahulvohra/

• How Superhuman Built an Engine to Find Product Market Fit: https://review.firstround.com/how-superhuman-built-an-engine-to-find-product-market-fit/

• How to validate your startup idea: https://www.lennysnewsletter.com/p/validating-your-startup-idea

• How the most successful B2B startups came up with their original idea: https://www.lennysnewsletter.com/p/how-the-most-successful-b2b-startups

• How to know if you’ve got product-market fit: https://www.lennysnewsletter.com/p/how-to-know-if-youve-got-productmarket

• A guide for finding product-market fit in B2B: https://www.lennysnewsletter.com/p/finding-product-market-fit

• Product-market fit method: http://pmf.firstround.com/

• Stripe: https://stripe.com/

• Plaid: https://plaid.com/

• Paths to PMF: https://review.firstround.com/series/product-market-fit/

• WeWork: https://www.wework.com/

• Casper: https://casper.com/

• Vanta: https://www.vanta.com/

• Christina Cacioppo on LinkedIn: https://www.linkedin.com/in/ccacioppo/

• Ramp: https://ramp.com/

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

• Jack Altman on LinkedIn: https://www.linkedin.com/in/jackealtman/

• Lattice: https://lattice.com/

• Zachary Perret on LinkedIn: https://www.linkedin.com/in/zperret/

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

• Retool: https://retool.com/

• David Hsu on LinkedIn: https://www.linkedin.com/in/dvdhsu/

• Persona: https://withpersona.com/

• Rick Song on LinkedIn: https://www.linkedin.com/in/rick-song-25198b24/

• Lloyd Tabb on LinkedIn: https://www.linkedin.com/in/lloydtabb/

• Looker: https://en.wikipedia.org/wiki/Looker_(company)

• Jason Boehmig on LinkedIn: https://www.linkedin.com/in/jboehmig/

• Ironclad: https://ironcladapp.com/

• Lessons in leadership | Scaling an org and tactical management advice | Jack Altman (Lattice): https://www.youtube.com/watch?v=cZzXqf61mrQ

• Filip Kaliszan on LinkedIn: https://www.linkedin.com/in/kaliszan/

• Verkada: https://www.verkada.com/

• Ali Ghodsi on LinkedIn: https://www.linkedin.com/in/alighodsi/

• Databricks: https://www.databricks.com/

• Stripe Radar: https://stripe.com/radar

• Stripe Atlas: https://stripe.com/atlas

• Square Stand: https://squareup.com/shop/hardware/us/en/products/ipad-pos-stand-integrated-card-reader

• Cash App: https://cash.app/

• Square Checking: https://squareup.com/us/en/campaign/banking/checking

• Square Loan: https://squareup.com/help/us/en/article/5654-get-started-with-square-capital

• Casey Winters on LinkedIn: https://www.linkedin.com/in/caseywinters/

• How to sell your ideas and rise within your company | Casey Winters, Eventbrite: https://www.lennyspodcast.com/how-to-sell-your-ideas-and-rise-within-your-company-casey-winters-eventbrite/

• Josh Kopelman on LinkedIn: https://www.linkedin.com/in/jkopelman/

• The art and science of pricing | Madhavan Ramanujam (Monetizing Innovation, Simon-Kucher): https://www.lennyspodcast.com/videos/the-art-and-science-of-pricing-madhavan-ramanujam-monetizing-innovation-simon-kucher/

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

Claire Vo is the chief product officer at LaunchDarkly and the founder of ChatPRD, likely the most popular PM-specific AI product out there. Before LaunchDarkly, she was a longtime chief product officer at Color and Optimizely. Claire has founded and managed two other companies, Pretty HQ and Experiment Engine, the latter of which Optimizely acquired in 2017. In our conversation, we discuss:

• Knowing what you want in your career and being clear about it

• Finding your zone of genius and how to operate within it

• How to maintain a fast pace in larger companies

• How to make it easy for your boss to help you achieve your goals

• Advice for navigating the tech industry as a woman

• The role of a CPTO and the benefits it brings to organizations

• Why she built ChatPRD

• Tips for building your own AI tools

• The impact of AI on product management and what skills will continue to be important

—

Brought to you by:

• Orb—The flexible billing engine for modern pricing

• Dovetail—Bring your customer into every decision

• Vanta—Automate compliance. Simplify security

—

Find the full transcript at: https://www.lennysnewsletter.com/p/bending-the-universe-in-your-favor

—

Where to find Claire Vo:

• X: https://twitter.com/clairevo

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

• TikTok: https://www.tiktok.com/@chiefproductofficer

—

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) Claire’s background

(04:50) How to achieve career progression

(10:11) Avoiding promotion obsession

(13:50) How Claire stepped into leadership roles

(17:24) Operating in your zone of genius

(23:03) How to maintain a fast pace

(27:46) Setting a high bar for quality and talent

(29:54) Normalizing feedback

(33:09) Being a woman in tech

(47:09) The role of a CPTO

(54:19) Building ChatPRD

(59:39) Tips for building a GPT

(01:02:27) The impact of AI on product management

(01:08:08) How AI is changing the product management role

(01:14:36) Efficiency gains with ChatPRD

(01:16:39) Contrarian corner: sales-led product organizations

(01:20:11) Lightning round

—

Referenced:

• LaunchDarkly: https://launchdarkly.com/

• Define your zone of genius: Laura Garnett at TEDxMillRiver: https://www.youtube.com/watch?v=gQ7_r2oWlrw

• Energy Audit: https://beta.mocharymethod.com/blog-post/energy-audit

• How to fire people with grace, work through fear, and nurture innovation | Matt Mochary: https://www.lennyspodcast.com/videos/how-to-fire-people-with-grace-work-through-fear-and-nurture-innovation-matt-mochary/

• Radical Candor: From theory to practice with author Kim Scott: https://www.lennyspodcast.com/radical-candor-from-theory-to-practice-with-author-kim-scott/

• Optimizely: https://www.optimizely.com/

• GitLab: https://about.gitlab.com/

• ChatPRD: https://www.chatprd.ai/

• You should be playing with GPTs at work: https://www.lennysnewsletter.com/p/you-should-be-playing-with-gpts-at

• SpaceX’s Starship: https://www.spacex.com/vehicles/starship/

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

• Product management theater | Marty Cagan (Silicon Valley Product Group): https://www.lennyspodcast.com/product-management-theater-marty-cagan-silicon-valley-product-group/

• High Growth Handbook: Scaling Startups from 10 to 10,000 People: https://www.amazon.com/High-Growth-Handbook-Elad-Gil/dp/1732265100

• Scaling People: Tactics for Management and Company Building: https://www.amazon.com/Scaling-People-Tactics-Management-Building/dp/1953953212

• Stripe Press: https://press.stripe.com/

• Circe: https://www.amazon.com/Circe-Madeline-Miller/dp/0316556327

• Poor Things: https://www.imdb.com/title/tt14230458/

• Mythic Quest on AppleTV+: https://tv.apple.com/us/show/mythic-quest/umc.cmc.1nfdfd5zlk05fo1bwwetzldy3

• Silicon Valley on HBO: https://www.hbo.com/silicon-valley

• Chrysler Pacifica: https://www.chrysler.com/pacifica.html

• Waymo: https://waymo.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.

Dharmesh Shah is the co-founder and CTO of HubSpot (currently valued at $30 billion) and one of the most fascinating founders I’ve ever met. Dharmesh is the keeper of HubSpot’s Culture Code, built ChatSpot (an AI chatbot built on top of HubSpot CRM) and a game called WordPlay (which grew to 16 million users), and also founded and writes for OnStartups, a top-ranking startup blog and community with more than 1M members. He’s also invested in 100+ startups including OpenAI, AngelList, Coinbase, and Dropbox. In our conversation, we discuss:

• The biggest lessons he has learned from building HubSpot

• The importance of leaning into your strengths

• Dharmesh’s data-oriented approach to public speaking

• How he developed HubSpot’s culture code

• The decision-making process at HubSpot

• His contrarian approach to building products

• Why founders and product teams are all fighting the second law of thermodynamics

• How “flash tags” can save your teams time

• How to decide what ideas are worth investing in

—

Brought to you by:

• Explo—Embed customer-facing analytics in your product

• Vanta—Automate compliance. Simplify security

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

—

Find the full transcript at: https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building

—

Where to find Dharmesh Shah:

• X: https://twitter.com/dharmesh

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

• Website: https://dharmesh.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) Dharmesh’s background

(04:20) Fun facts about Dharmesh

(06:31) His data-oriented approach to public speaking

(11:45) Advice for adding humor to your presentations

(15:28) Why he has no direct reports

(18:46) You can shape the universe to your liking

(20:02) Lessons from building HubSpot

(23:43) Contrarian ways of running a company

(37:26) Fighting the second law of thermodynamics

(40:29) The importance of simplicity in running a business

(45:22) Succeeding in the SMB market

(50:29) Zigging when others are zagging

(54:17) When it makes sense to go “wide and deep”

(57:33) Using flashtags to communicate opinions

(01:02:44) HubSpot’s decision-making process

(01:09:41) Deciding what ideas to invest in

(01:15:26) Defining and maintaining company culture

(01:30:46) The potential of AI

(01:37:03) Practical advice for learning AI

(01:40:07) Where to find Dharmesh

—

Referenced:

• WordPlay: https://wordplay.com/article/unlimited

• ChatSpot: https://chatspot.ai/

• Indian-origin entrepreneur buys ‘chat.com’ for over $10 million, then sells, donates $250,000 to Khan Academy: https://www.businesstoday.in/technology/news/story/indian-origin-entrepreneur-buys-chatcom-for-over-10-million-then-sells-donates-250000-to-khan-academy-382907-2023-05-26

• Kipp Bodnar on LinkedIn: https://www.linkedin.com/in/kippbodnar/

• The surprising metric presenters should analyze: https://lars-sudmann.com/the-surprising-metric-presenters-should-analyze/

• SoloWare: https://www.linkedin.com/posts/dharmesh_for-3-decades-now-in-addition-to-my-day-activity-7166500611247583232-kZgb/

• Brian Halligan on LinkedIn: https://www.linkedin.com/in/brianhalligan/

• First Principles: Elon Musk on the Power of Thinking for Yourself: https://jamesclear.com/first-principles

• Peter Thiel on LinkedIn: https://www.linkedin.com/in/peterthiel/

• The second law of thermodynamics: https://en.wikipedia.org/wiki/Second_law_of_thermodynamics

• What is an SMB?: https://www.techtarget.com/whatis/definition/SMB-small-and-medium-sized-business-or-small-and-midsized-business

• Shopify: https://www.shopify.com/

• Relentless curiosity, radical accountability, and HubSpot’s winning growth formula | Christopher Miller (VP of Product, Growth and AI): https://www.lennyspodcast.com/relentless-curiosity-radical-accountability-and-hubspots-winning-growth-formula-christopher-mil/

• FlashTags: A Simple Hack for Conveying Context Without Confusion: https://www.onstartups.com/flashtags-a-simple-hack-for-conveying-context-without-confusion

• What it means to “disagree and commit”: https://news.ycombinator.com/item?id=16949021

• A Simple Decision Framework: Debate, Decide and Unite: https://connectingdots.com/p/debate-decide-unite

• Dharmesh Shah’s Frameworks for Creating a $1 Billion Net Worth: https://hakune.co/dharmesh-shah-networth/

• Zip: https://ziphq.com/

• The HubSpot Culture Code: Creating a Company We Love: https://blog.hubspot.com/blog/tabid/6307/bid/34234/the-hubspot-culture-code-creating-a-company-we-love.aspx

• How defining values and culture helped Airbnb achieve worldwide success: https://lattice.com/library/how-defining-values-and-culture-helped-airbnb-achie

• What is SQL?: https://aws.amazon.com/what-is/sql/

• GrowthBot: https://community.hubspot.com/t5/Releases-and-Updates/Meet-GrowthBot-from-HubSpot-Labs/ba-p/417985

—

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.

Matt Abrahams is a renowned communication expert, with decades of teaching, coaching, and consulting experience. At Stanford University, he teaches a business school class on strategic communication. Beyond academia, he’s a sought-after keynote speaker and consultant, guiding presenters from IPO road shows to prestigious platforms like TED, the World Economic Forum, and the United Nations. His acclaimed podcast, Think Fast, Talk Smart, garners millions of listeners, and his book, Think Faster, Talk Smarter, equips speakers with practical skills for impromptu success. With a previous bestseller, Speaking Up Without Freaking Out, Matt has empowered countless individuals to speak confidently and authentically. In our conversation, we discuss:

• The concept of “daring to be dull”

• The power of visualization to desensitize oneself to speaking situations

• Managing negative self-talk

• The WHAT structure for delivering toasts (why we are here, how you are connected, anecdote, thanks)

• The ADD structure for Q&As (answer, detailed example, describe relevance)

• Breathing techniques to reduce anxiety, such as the double exhale

• Concrete speaking structures like What? So What? Now What? and the Four I’s (information, impact, invitation, implications)

• Much more

—

Brought to you by:

• Sprig—Build a product people love

• Dovetail—Bring your customer into every decision

• Coda—Meet the evolution of docs

—

Find the transcript and references at: https://www.lennysnewsletter.com/p/how-to-speak-more-confidently-and

—

Where to find Matt Abrahams:

• X: https://twitter.com/tftsthepod

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

• Website: https://mattabrahams.com/

• Podcast: https://open.spotify.com/show/6ll0MwobDt1JW9gYaOONEo

—

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) Matt’s background

(04:50) Techniques for managing anxiety in public speaking

(10:57) Dare to be dull

(13:40) Reframing anxiety as excitement

(16:08) Using mantras to boost confidence

(18:45) Managing negative self-talk

(20:03) Normalizing speaking anxiety

(23:12) Using conversation as a communication technique

(24:52) Using the double-exhale breathing technique

(28:29) Getting present-oriented

(29:46) Using tongue twisters

(33:34) Broad advice for speaking on the spot

(38:35) The PREP structure

(38:59) The What? So What? Now What? structure

(42:10) Toastmasters and improv

(45:31) Getting better at small talk

(51:05) The importance of sharing back

(52:33) Giving feedback

(56:31) Improving toasts and tributes

(01:02:57) Mastering Q&A sessions

(01:07:25) Apologizing effectively

(01:09:29) Closing thoughts

—

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.

Kunal Shah is one of the most well-known and admired product leaders in India. He is the CEO and founder of CRED, an Indian-based fintech startup valued at over $6 billion. Prior to CRED, he founded three other startups, including Freecharge, which he sold for over $400 million to Snapdeal. He has also been an advisor to India’s most influential organizations. In our conversation, we discuss:

• The prevalence of successful Indian immigrants in top CEO roles across the tech industry

• Why companies in India can grow DAUs but not ARPU—and what that means for building products for India

• What most sets India’s market apart

• Challenges and opportunities in the Indian market

• The Delta 4 framework for building new products

• Lessons from building CRED so far

• The power of curiosity and second-order thinking

• Lessons from failure

—

Brought to you by:

• WorkOS—The modern API for auth and user identity

• Orb—The flexible billing engine for modern pricing

• Dovetail—Bring your customer into every decision

—

Find the transcript and references at: https://www.lennysnewsletter.com/p/kunal-shah-on-winning-in-india-second

—

Where to find Kunal Shah:

• X: https://twitter.com/kunalb11

• LinkedIn: https://www.linkedin.com/in/kunalshah1/

• Podcast: https://www.youtube.com/@CRED_club

—

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) Kunal’s background

(04:22) The Delta 4 framework

(11:00) The success of Indian CEOs in the U.S.

(19:55) Challenges and opportunities in India

(23:04) DAUs vs. ARPU in Indian markets

(25:50) The perception of time in India

(27:55) The curse of focus in Asian markets

(30:33) Challenges and opportunities in India (continued)

(33:23) Lessons learned from building CRED

(36:40) Profit pools can provide valuable insights into the values of a country

(37:55) Founders’ role in company growth

(39:55) Profitability and Indian business culture

(43:24) Advice for staying positive amid criticism

(44:41) The promising market in India

(47:35) The power of curiosity

(52:59) Who Kunal looks up to

(55:31) Kunal’s favorite sources of content

(58:42) Asking great questions

(01:02:54) Contrarian corner: Wealth is nothing but storage of energy

(01:05:26) Failure corner

(01:08:57) Closing thoughts: Share your learnings

(01:09:38) Lightning round

—

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.

Emilie Gerber is the founder and CEO of Six Eastern, a top PR agency that’s worked with over 100 tech companies, from stealth startups to publicly traded companies. Before starting her own firm, she worked at Uber, where she led PR for the business development team and B2B programs. Prior to that, she worked at Box on product communications, with a focus on product launches and partnership announcements. In our conversation, we discuss:

• Why, and when, getting press is worth your time

• Common misconceptions about the impact press can have

• The second-order effects of press

• Which areas each publication (TechCrunch, Axios, The Verge, etc.) cares most about

• How to craft your pitch

• How to find and reach reporters

• How pitching press is different from pitching customers

• The effectiveness of direct communication through social media versus traditional press

—

Brought to you by:

• Sprig—Build a product people love

• Eppo—Run reliable, impactful experiments

• Vanta—Automate compliance. Simplify security.

—

Find the full transcript at: https://www.lennysnewsletter.com/p/the-ultimate-guide-to-pr-emilie-gerber

—

Where to find Emilie Gerber:

• Substack: http://onbackgroundintel.substack.com

• LinkedIn: https://www.linkedin.com/in/emilie-gerber-59612230/

• Website: https://sixeastern.com/

• Email: [email protected]

—

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) Emilie’s background

(04:56) The value of press and second-order effects

(13:00) When press is not worth your time

(17:01) Different publications and their suitability

(25:36) Avoiding negative stories

(27:23) Finding aligned podcasts and awards

(31:12) Advice for reaching out to reporters

(37:23) Controversial pitches

(41:16) Avoiding category creation

(43:26) Examples of pitches that have worked well

(53:32) Pitching to Lenny

(55:46) Effective pitching strategies

(57:45) Improving pitch announcements

(01:03:01) Press releases

(01:07:06) Crafting a compelling story

(01:09:43) Traditional press vs. newsletters, podcasts, and social media

(01:15:50) Building a social media presence

(01:17:51) How to get a Morning Brew feature

(01:19:32) Advice on choosing a PR agency

(01:22:25) Timing and budget for PR

(01:25:39) Lightning round

—

Referenced:

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

• Who is Lenny Rachitsky? And what does he know that you don’t about making millions writing online?: https://www.fastcompany.com/90940453/lenny-rachitsky-newsletter-podcast-job-board-substack

• 42-year-old brings in an average of $41,000 a month from his podcast and works on it just 5 hours a week: https://www.cnbc.com/2024/01/11/lenny-rachitsky-podcast-brings-in-more-than-500k-a-year-heres-how.html

• How This Newsletter Writer Got More Than 300,000 Subscribers, and Now Makes “Significantly More” Than He Did at His Day Job: https://www.entrepreneur.com/starting-a-business/how-this-newsletter-writer-got-more-than-300000/447172

• Business Insider: https://www.businessinsider.com/

• Contraline: https://www.contraline.com/

• Forbes: https://www.forbes.com/

• TechCrunch: https://techcrunch.com/

• Axios: https://www.axios.com/

• Fortune: https://fortune.com/

• Term Sheet: https://fortune.com/tag/term-sheet/

• The Verge: https://www.theverge.com/

• Wall Street Journal: https://www.wsj.com/

• New York Times: https://www.nytimes.com/

• Found podcast: https://techcrunch.com/tag/found/

• Equity podcast: https://techcrunch.com/tag/equity-podcast/

• VentureBeat: https://venturebeat.com/

• Fast Company: https://www.fastcompany.com/

• Clockwise: https://www.getclockwise.com

• Shopify deleted 322,000 hours of meetings. Should the rest of us be jealous?: https://www.npr.org/2023/02/15/1156804295/shopify-delete-meetings-zoom-virtual-productivity

• Shopify canceled all recurring meetings. Should you too?: https://www.getclockwise.com/blog/shopify-cancels-meetings

• Shopify’s new meeting cost calculator is well intentioned—but it’s not addressing the issue: https://www.fastcompany.com/90930137/shopifys-new-meeting-cost-calculator-is-well-intentioned-but-its-not-addressing-the-issue

• Matt Martin on LinkedIn: https://www.linkedin.com/in/voxmatt/

• Ramp: https://ramp.com/welcome

• Corporate card start-up Ramp targets Bill.com with free payments software: https://www.cnbc.com/2021/10/26/corporate-cards-ramp-targets-billcom-with-free-payments-software.html

• Bill: https://www.bill.com/

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

• Column Tax: https://www.columntax.com/

• Propel: https://www.joinpropel.com/

• Gamma: https://gamma.app/

• Gamma brings in $7M to bring the slide deck into the 21st century: https://techcrunch.com/2021/10/28/gamma-brings-in-7m-to-bring-the-slide-deck-into-the-21st-century/

• NewBank: https://www.newbankusa.com/

• Backed by a16z, Relay races to market with Zapier in its crosshairs: https://techcrunch.com/2023/10/11/relay-a16z-zapier-google/

• Zapier: https://zapier.com/

• Rajiv Ayyangar’s thread on X about tag lines: https://twitter.com/rajivayyangar/status/1758179077629100482

• Entropy: https://entropytechnologydesign.com/

• Money 20/20: https://www.money2020.com/

• Jim Bankoff on LinkedIn: https://www.linkedin.com/in/jimbankoff/

• Ramping Up: https://www.notboring.co/p/ramping-up

• Aaron Levie on LinkedIn: https://www.linkedin.com/in/boxaaron/

• Aaron Levie on X: https://twitter.com/levie

• Duolingo on TikTok: https://www.tiktok.com/@duolingo

• Morning Brew: https://www.morningbrew.com/

• Tech Brew: https://www.emergingtechbrew.com/

• HR Brew: https://www.hr-brew.com/

• Mark Zuckerberg on Morning Brew Daily: https://www.youtube.com/watch?v=xQqsvRHjas4&t=1309s

• How to Change Your Mind: What the New Science of Psychedelics Teaches Us About Consciousness, Dying, Addiction, Depression, and Transcendence: https://www.amazon.com/Change-Your-Mind-Consciousness-Transcendence/dp/1594204225

• The Walking Dead on Netflix: https://www.netflix.com/title/70177057

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

• The Last of Us on HBO: https://www.hbo.com/the-last-of-us

• Apple Vision Pro: https://www.apple.com/apple-vision-pro

• TNB Tech Minute: Startup Perplexity Challenges Google With AI Search: https://www.wsj.com/podcasts/tech-news-briefing/tnb-tech-minute-startup-perplexity-challenges-google-with-ai-search/984362d5-a8f0-48b4-8b55-ad7e570a74d2

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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.

Noam Lovinsky has had a distinguished career in product, leaving an indelible mark at Facebook, YouTube, Thumbtack, and currently as the chief product officer at Grammarly. At Facebook, Noam helped establish the New Product Experimentation team; at Thumbtack, he was chief product officer; and at YouTube, he was one of the early product leaders overseeing the consumer experience. In our conversation, we discuss:

• Challenges and lessons from reviving growth at YouTube and Thumbtack

• Lessons from building Facebook’s New Product Experimentation team

• Insights into Grammarly’s success

• Knowing when it’s time to kill your project

• Why diversifying your growth channels is critical

• The power of visioning and storytelling in shaping product strategy

• How to create space for innovation at large companies

• The resilience and motivation of Grammarly’s team in Ukraine

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Brought to you by:

• Whimsical—The iterative product workspace

• Vanta—Automate compliance. Simplify security.

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

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Find the full transcript at: https://www.lennysnewsletter.com/p/the-happiness-and-pain-of-product

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Where to find Noam Lovinsky:

• X: https://twitter.com/noaml

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

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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) Noam’s background

(04:18) Noam’s lack of online presence

(08:06) Lessons from YouTube: advocating for what’s best for yourself and the team

(14:31) Prioritizing what’s best for the business

(19:37) Knowing when it’s time to kill a project

(21:47) Lessons from Thumbtack: diversifying growth channels and overcoming challenges

(26:24) How Thumbtack turned growth around

(31:44) Building Airbnb’s instant booking feature

(35:28) Lessons from Thumbtack: team collaboration and product strategy

(38:38) Lessons from Facebook: building the New Product Experimentation team

(40:43) The importance of starting small and building community density

(46:07) Advice for building a startup within a startup

(48:52) Having an incentive system

(49:34) Lessons from Grammarly: adapting to changing user needs and building for the masses

(54:20) The scrappiness and profitability of Grammarly

(56:56) The resilience and motivation of the Grammarly team in Ukraine

(59:08) General career advice

(01:01:02) When to pull back

(01:02:58) Closing thoughts

(01:03:56) Lightning round

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Referenced:

• Substack: https://substack.com/

• Hunter Walk on LinkedIn: https://www.linkedin.com/in/hunterwalk/

• The rituals of great teams | Shishir Mehrotra of Coda, YouTube, Microsoft: https://www.lennyspodcast.com/the-rituals-of-great-teams-shishir-mehrotra-coda-youtube-microsoft/

• Salar Kamangar on LinkedIn: https://www.linkedin.com/in/salar-kamangar-5a059712/

• Grammarly: https://www.grammarly.com/

• Thumbtack: https://www.thumbtack.com/

• FRED on YouTube: https://www.youtube.com/FRED

• How Airbnb Proved That Storytelling Is the Most Important Skill in Design: https://www.inc.com/yazin-akkawi/the-surprising-technique-airbnb-uses-to-better-sell-an-experience.html

• Google+: https://en.wikipedia.org/wiki/Google%2B

• Marco Zappacosta on LinkedIn: https://www.linkedin.com/in/marcozappacosta/

• Bryan Schreier on LinkedIn: https://www.linkedin.com/in/bryanschreier/

• Whitney Steele on LinkedIn: https://www.linkedin.com/in/whitneydsteele/

• David Shein on LinkedIn: https://www.linkedin.com/in/davidshein/

• The magic of thinking big, by Lenny Rachitsky: https://www.mindtheproduct.com/the-magic-of-thinking-big-by-lenny-rachitsky/

• What Seven Years at Airbnb Taught Me About Building a Business: https://www.lennysnewsletter.com/p/what-seven-years-at-airbnb-taught

• New apps, new experiences: NPE Team, from Facebook: https://tech.facebook.com/engineering/2019/7/npe-team-from-facebook/

• The Origin Story of the BRC Trash Fence: https://journal.burningman.org/2016/05/black-rock-city/leaving-no-trace/the-origin-story-of-the-brc-trash-fence/

• Nike opens high-tech research and innovation lab: https://www.just-style.com/news/nike-opens-high-tech-research-and-innovation-lab/

• ChatGPT: https://chat.openai.com/

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

• How to grow a subscription business | Yuriy Timen (Grammarly, Canva, Airtable): https://www.lennyspodcast.com/how-to-grow-a-subscription-business-yuriy-timen-grammarly-canva-airtable/

• “The cave you fear to enter holds the treasure you seek”: https://gointothestory.blcklst.com/the-cave-you-fear-to-enter-holds-the-treasure-you-seek-d624e28c3848

• Build: An Unorthodox Guide to Making Things Worth Making: https://www.amazon.com/Build-Unorthodox-Guide-Making-Things/dp/0063046067

• For All Mankind on AppleTV+: https://tv.apple.com/us/show/for-all-mankind/umc.cmc.6wsi780sz5tdbqcf11k76mkp7

• Fargo TV series on Hulu: https://www.fxnetworks.com/shows/fargo

• Arc browser: https://arc.net/

• Competing with giants: An inside look at how The Browser Company builds product | Josh Miller (CEO): https://www.lennyspodcast.com/competing-with-giants-an-inside-look-at-how-the-browser-company-builds-product-josh-miller-ceo/

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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.