Lenny's Podcast: Product | Growth | Career Lenny Rachitsky

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
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Find the transcript at: https://www.lennysnewsletter.com/p/lessons-from-1000-yc-startups
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Where to find Dalton Caldwell:
• X: https://twitter.com/daltonc
• LinkedIn: https://www.linkedin.com/in/daltoncaldwell/
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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) 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
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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://ww

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
—
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• Paragon—Ship every SaaS integration your customers want
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Find the transcript at: https://www.lennysnewsletter.com/p/the-gitlab-way
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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
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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) 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
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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-mar

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
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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
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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 | Geof

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
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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
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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/
—
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
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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

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
—
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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.l

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
—
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• Coda—Meet the evolution of docs
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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
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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/
—
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
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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.
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Lenny may be an investor in the companies discussed.


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