Lenny’s Podcast: Product | Growth | Career

Bob Moesta, co-creator of the Jobs to Be Done framework, recently published a new book, Job Moves. Drawing from interviews with over 1,000 people about their career transitions, it offers a practical playbook for career development. In our conversation, we discuss:

• The four different “quests” that drive career changes

• Why job features (salary, title) matter less than experiences

• How to identify what gives you energy vs. drains you

• The power of taking a “jobcation”

• A template for crafting your career story

• Tips for hiring and retaining great talent

• The importance of prototyping potential careers

• Much more

—

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Find the transcript at: https://www.lennysnewsletter.com/p/how-to-find-work-you-love-bob-moesta

—

Where to find Bob Moesta:

• X: https://x.com/bmoesta

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

• Website: https://www.jobmoves.com/

• Podcast: https://pca.st/gg6goo1n

• The Re-Wired Group: https://therewiredgroup.com/

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Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

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

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In this episode, we cover:

(00:00) Bob's background

(05:10) Bob’s new book, Job Moves

(09:31) Job features vs. job experiences

(11:16) Four reasons people leave jobs

(17:20) Energy drivers and energy drains

(31:05) Prototyping your next job

(34:32) Pushes and pulls

(40:01) Understanding that no job is perfect

(43:18) Taking a jobcation

(51:22) Finding the right next step

(55:18) Navigating job applications and interviews

(58:28) How to craft your career story

(01:04:04) Strengths and weaknesses: leveraging your superpowers

(01:06:21) Hiring and writing job descriptions

(01:11:20) Self-awareness and founding a startup

(01:21:24) Conclusion and final thoughts

—

Referenced:

• The ultimate guide to JTBD | Bob Moesta (co-creator of the framework): https://www.lennysnewsletter.com/p/the-ultimate-guide-to-jtbd-bob-moesta

• Ethan S. Bernstein on LinkedIn: https://www.linkedin.com/in/ethanbernstein/

• National Geographic: https://www.nationalgeographic.com/

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

• Building a long and meaningful career | Nikhyl Singhal (Meta, Google): https://www.lennysnewsletter.com/p/building-a-long-and-meaningful-career

• The Story Spine (also known as Pixar’s Story Structure): https://www.storyprompt.com/blog/the-story-spine-also-known-as-pixars-story-structure

• Tobi Lütke on LinkedIn: https://www.linkedin.com/in/tobiaslutke

• Job Moves resources: https://www.jobmoves.com/resources

• Why Employees Quit: https://hbr.org/2024/11/why-employees-quit

—

Recommended book:

• Job Moves: 9 Steps for Making Progress in Your Career: https://www.amazon.com/Job-Moves-Making-Progress-Career/dp/0063283581

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

—

Lenny may be an investor in the companies discussed.

Uri Levine is a co-founder of Waze (which was acquired by Google for $1.3 billion in 2013), along with nine other companies (including another company he sold for over $1 billion). He’s also been on 20 boards and has been an advisor to over 50 startups. He recently released a new chapter of his best-selling book Fall in Love with the Problem, Not the Solution, which provides a guide to surviving crises at your company. In this episode, we cover:

• The two types of startup crisis and how to handle them

• Why speed of action is the most important thing

• How to keep your team motivated when things look dire

• A framework for deciding whether or not to pivot

• What to do when product-market fit disappears

• How to approach raising money during a crisis

• More

—

Brought to you by:

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

• Rippling—Automate HR, IT, and finance so you can scale faster

• OneSchema—Import CSV data 10x faster

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Find the transcript at: https://www.lennysnewsletter.com/p/a-founders-guide-to-crisis-management-uri-levine

—

Where to find Uri Levine:

• X: https://twitter.com/urilevine1

• LinkedIn: https://www.linkedin.com/in/uri-levine

• Website: https://urilevine.com

• Book: https://www.amazon.com/Fall-Love-Problem-Solution-Entrepreneurs/dp/1637746601/ref=tmm_pap_swatch_0?_encoding=UTF8&qid=&sr=

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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) Welcome back, Uri!

(05:10) The new chapter: navigating crises

(08:15) Types of crises founders face

(29:10) Navigating cash crises

(38:31) The importance of never giving up

(46:26) How to keep people engaged through a crises

(47:59) Transparency in crisis management

(56:58) Navigating product-market-fit challenges

(59:27) Deciding when to pivot or shut down

(01:13:34) Real-life startup survival stories

(01:17:06) Avoiding and preparing for crises

(01:21:21) Final thoughts and book promotion

—

Referenced:

• Waze: https://www.waze.com/

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

• Order Chat: https://www.crunchbase.com/organization/order-chat

• Fibo: https://finder.startupnationcentral.org/company_page/fibo

• Behind the founder: Drew Houston (Dropbox): https://www.lennysnewsletter.com/p/behind-the-founder-drew-houston-dropbox

• TomTom: https://www.tomtom.com/

• Khosla Ventures: https://www.khoslaventures.com/

• WeSki: https://www.weski.com/

• Larry Silverstein: https://en.wikipedia.org/wiki/Larry_Silverstein

• Oversee: https://oversee.biz/

• Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director): https://www.lennysnewsletter.com/p/lessons-from-1000-yc-startups

• Tobi Lütke’s leadership playbook: Playing infinite games, operating from first principles, and maximizing human potential (founder and CEO of Shopify): https://www.lennysnewsletter.com/p/tobi-lutkes-leadership-playbook

• Harley Finkelstein on LinkedIn: https://www.linkedin.com/in/harleyf/

• Zip: https://zip.co/us

• Qualcomm: https://www.qualcomm.com/

• Einstein quote: https://www.brainyquote.com/quotes/albert_einstein_148788

—

Recommended book:

• Fall in Love with the Problem, Not the Solution: A Handbook for Entrepreneurs (updated 2025 version): https://urilevine.com/book/#Pre-order

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

—

Lenny may be an investor in the companies discussed.

Karina Nguyen leads research at OpenAI, where she’s been pivotal in developing groundbreaking products like Canvas, Tasks, and the o1 language model. Before OpenAI, Karina was at Anthropic, where she led post-training and evaluation work for Claude 3 models, created a document upload feature with 100,000 context windows, and contributed to numerous other innovations. With experience as an engineer at the New York Times and as a designer at Dropbox and Square, Karina has a rare firsthand perspective on the cutting edge of AI and large language models. In our conversation, we discuss:

• How OpenAI builds product

• What people misunderstand about AI model training

• Differences between how OpenAI and Anthropic operate

• The role of synthetic data in model development

• How to build trust between users and AI models

• Why she moved from engineering to research

• Much more

—

Brought to you by:

• Enterpret—Transform customer feedback into product growth

• Vanta—Automate compliance. Simplify security

• Loom—The easiest screen recorder you’ll ever use

—

Find the transcript at: https://www.lennysnewsletter.com/p/why-soft-skills-are-the-future-of-work-karina-nguyen

—

Where to find Karina Nguyen:

• X: https://x.com/karinanguyen_

• LinkedIn: https://www.linkedin.com/in/karinanguyen28

• Website: https://karinanguyen.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) Introduction to Karina Nguyen

(04:42) Challenges in model training

(08:21) Synthetic data and its importance

(12:38) Creating Canvas

(18:33) Day-to-day operations at OpenAI

(20:28) Writing evaluations

(23:22) Prototyping and product development

(26:57) Building Canvas and Tasks

(33:34) Understanding the job of a researcher

(35:36) The future of AI and its impact on work and education

(42:15) Soft skills in the age of AI

(47:50) AI’s role in creativity and strategy development

(53:34) Comparing Anthropic and OpenAI

(57:11) Innovations and future visions

(01:07:13) The potential of AI agents

(01:11:36) Final thoughts and career advice

—

Referenced:

• What’s in your stack: The state of tech tools in 2025: https://www.lennysnewsletter.com/p/whats-in-your-stack-the-state-of

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

• OpenAI: https://openai.com/

• What is synthetic data—and how can it help you competitively?: https://mitsloan.mit.edu/ideas-made-to-matter/what-synthetic-data-and-how-can-it-help-you-competitively

• GPQA: https://datatunnel.io/glossary/gpqa/

• Canvas: https://openai.com/index/introducing-canvas/

• Barret Zoph on LinkedIn: https://www.linkedin.com/in/barret-zoph-65990543/

• Mira Murati on LinkedIn: https://www.linkedin.com/in/mira-murati-4b39a066/

• JSON Schema: https://json-schema.org/

• Anthropic—100K Context Windows: https://www.anthropic.com/news/100k-context-windows

• Claude 3 Haiku: https://www.anthropic.com/news/claude-3-haiku

• A.I. Chatbots Defeated Doctors at Diagnosing Illness: https://www.nytimes.com/2024/11/17/health/chatgpt-ai-doctors-diagnosis.html

• Cursor: https://www.cursor.com/

• How AI will impact product management: https://www.lennysnewsletter.com/p/how-ai-will-impact-product-management

• Lee Byron on LinkedIn: https://www.linkedin.com/in/lee-byron/

• GraphQL: https://graphql.org/

• Claude in Slack: https://www.anthropic.com/claude-in-slack

• Sam Altman on X: https://x.com/sama

• Jakub Pachocki on LinkedIn: https://www.linkedin.com/in/jakub-pachocki/

• Lennybot: https://www.lennybot.com/

• ElevenLabs: https://elevenlabs.io/

• Westworld on Prime Video: https://www.amazon.com/Westworld-Season-1/dp/B01N05UD06

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

• Tuple: https://tuple.app/

• How Shopify builds a high-intensity culture | Farhan Thawar (VP and Head of Eng): https://www.lennysnewsletter.com/p/how-shopify-builds-a-high-intensity-culture-farhan-thawar

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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

—

Lenny may be an investor in the companies discussed.

Tobi Lütke is the founder and CEO of Shopify, a $130 billion business that powers over 10% of all U.S. e-commerce. Starting as a snowboard shop in 2004, Shopify has become the leading commerce platform by consistently approaching problems differently. Tobi remains deeply technical, frequently coding alongside his team, and is known for his unique approach to leadership, product development, and company building. In our conversation, we discuss:

• Why complexity kills entrepreneurship

• How to develop and leverage your unique talent stack

• How specifically Tobi approaches thinking from first principles

• The importance of focusing on unquantifiable qualities like joy and delight

• Why Tobi works backward from a 100-year vision

• Why metrics should support decisions, not make them

• The power of following your curiosity

• What Tobi believes it takes to be a great product leader

• Much more

—

Brought to you by:

• Sinch—Build messaging, email, and calling into your product

• Liveblocks—Ready-made collaborative features to drop into your product

• Loom—The easiest screen recorder you’ll ever use

—

Find the transcript at: https://www.lennysnewsletter.com/p/tobi-lutkes-leadership-playbook

—

Where to find Tobi Lütke:

• X: https://x.com/tobi

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

• Website: https://tobi.lutke.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) Welcome and introduction

(04:17) The Tobi tornado

(07:10) Maximizing human potential

(11:05) Education and personal growth

(16:47) Operating without KPIs

(25:00) First-principles thinking

(40:04) Remote work

(45:59) Why Tobi never stopped coding

(54:46) Embracing disagreement

(01:01:27) The 100-year vision

(01:09:29) Balancing tactics and positioning

(01:17:15) Encouraging entrepreneurship

(01:19:34) The power of good UX

(01:28:42) The talent stack and unique opportunities

(01:34:30) The role of passion in product development

(01:36:39) Final thoughts and farewell

—

Referenced:

• How Shopify builds a high-intensity culture | Farhan Thawar (VP and Head of Eng): https://www.lennysnewsletter.com/p/how-shopify-builds-a-high-intensity-culture-farhan-thawar

• Breaking the rules of growth: Why Shopify bans KPIs, optimizes for churn, prioritizes intuition, and builds toward a 100-year vision | Archie Abrams (VP Product, Head of Growth at Shopify): https://www.lennysnewsletter.com/p/shopifys-growth-archie-abrams

• The ultimate guide to performance marketing | Timothy Davis (Shopify): https://www.lennysnewsletter.com/p/performance-marketing-timothy-davis

• Brandon Chu on building product at Shopify, how writing changed the trajectory of his career, the habits that make you a great PM, pros and cons of being a platform PM, how Shopify got through Covid: https://www.lennysnewsletter.com/p/brandon-chu-on-what-its-like-to-build

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

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

• Glen Coates on LinkedIn: https://www.linkedin.com/in/glcoates/

• How Shopify builds product: https://www.lennysnewsletter.com/p/how-shopify-builds-product

• The Last Dance on Netflix: https://www.netflix.com/title/80203144

• Autoregressive Models for Natural Language Processing: https://medium.com/@zaiinn440/autoregressive-models-for-natural-language-processing-b95e5f933e1f

• Archimedean property: https://en.wikipedia.org/wiki/Archimedean_property

• Tabula rasa: https://en.wikipedia.org/wiki/Tabula_rasa

• Daniel Weinand on LinkedIn: https://www.linkedin.com/in/danielweinand/

• World of Warcraft: https://worldofwarcraft.blizzard.com

• Harley Finkelstein on LinkedIn: https://www.linkedin.com/in/harleyf/

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

• The Sarbanes Oxley Act: https://sarbanes-oxley-act.com/

• Shopify builds Shopify Balance with Stripe to give small businesses an easier way to manage money: https://stripe.com/customers/shopify

• Stanford marshmallow experiment: https://en.wikipedia.org/wiki/Stanford_marshmallow_experiment

• Brian Armstrong on LinkedIn: https://www.linkedin.com/in/barmstrong/

• We are the Web: https://link.wired.com/public/32945405

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Recommended books:

• Finite and Infinite Games: https://www.amazon.com/Finite-Infinite-Games-James-Carse/dp/1476731713

• The Infinite Game: https://www.amazon.com/Infinite-Game-Simon-Sinek/dp/073521350X/

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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

—

Lenny may be an investor in the companies discussed.

Nan Yu is the head of product at Linear, one of the most beloved and fastest-growing B2B SaaS products out there today, and the gold standard for high-performing tech teams. In our conversation, we discuss:

• Why speed and quality aren’t actually at odds

• Linear’s unique approach to product development

• Nan’s systematic approach to creativity

• Linear’s philosophy on deadlines

• The “double triangle” framework for product management

• Nan’s approach to landing his dream product roles

• Much more

—

Brought to you by:

• Sinch—Build messaging, email, and calling into your product

• Paragon—Ship every SaaS integration your customers want

• Wix Studio—The web creation platform built for agencies

—

Find the transcript at: https://www.lennysnewsletter.com/p/linears-secret-to-building-beloved-b2b-products-nan-yu

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Where to find Nan Yu:

• X: https://x.com/thenanyu

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

—

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) Introduction to Nan Yu and Linear

(04:54) Survey insights: Linear vs. Jira

(07:51) The speed vs. quality myth

(09:24) Building and iterating quickly

(15:31) Avoiding bloat in enterprise software

(23:57) Understanding user needs deeply

(30:09) How to approach customer calls

(34:10) Creating strong emotional hooks

(40:31) Managing the product backlog

(44:46) Systemizing creativity

(48:16) Demo: Saving drafts in Linear

(51:38) Breaking constraints and building at extremes

(54:15) Adopting new tools

(58:22) The “double triangle” framework for product management

(01:04:23) Effective job-hunting strategies for PMs

(01:09:15) Thoughts on deadlines

(01:14:15) Lightning round

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Referenced:

• Jira: https://www.atlassian.com/software/jira

• Linear: https://linear.app/

• Patrick Collison’s post on X: https://x.com/patrickc/status/1869422495985750459

• Magnus Carlsen on X: https://x.com/magnuscarlsen

• Hikaru Nakamura on X: https://x.com/gmhikaru

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

• Customer Request feature on Linear: https://linear.app/customer-requests

• Everlane: https://www.everlane.com/

• Schlep Blindness: https://paulgraham.com/schlep.html

• Linear’s triage tool: https://linear.app/docs/triage

• Patrick Collison’s post about mental models on X: https://x.com/patrickc/status/1443215022029619200

• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach

• Unpacking Amazon’s unique ways of working | Bill Carr (author of Working Backwards): https://www.lennysnewsletter.com/p/unpacking-amazons-unique-ways-of

• Mode: https://mode.com/

• The Diplomat on Netflix: https://www.netflix.com/title/81288983

• Sakura Micron pens: https://www.amazon.com/SAKURA-PIGMA-MICRON-ESSENTIAL-COLORS/dp/B07VJFXT3C/

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Recommended books:

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

• The Design of Everyday Things: https://www.amazon.com/Design-Everyday-Things-Revised-Expanded/dp/0465050654/

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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

—

Lenny may be an investor in the companies discussed.

Chandra Janakiraman is the chief product officer, executive vice president, and a board member at VRChat. Previously, he was a product leader at Meta, where he led Facebook’s social experience interfaces and Reality Labs’ growth; served as CPO at Headspace, where he helped relaunch the platform, driving a 4x subscriber boost; and was a GM at Zynga, delivering massive hit games that reached hundreds of millions. In our conversation, Chandra shares:

• His playbook for developing a product strategy

• The difference between “small s” and “big S” strategy

• How to run strategy sprints

• Who should be involved in strategy work

• Common pitfalls in strategy development

• The role of AI in future strategy development

• More

—

Brought to you by:

• Eppo—Run reliable, impactful experiments

• Airtable ProductCentral—Launch to new heights with a unified system for product development

• OneSchema—Import CSV data 10x faster

—

Find the transcript at: https://www.lennysnewsletter.com/p/an-operators-guide-to-product-strategy-chandra-janakiraman

—

Where to find Chandra Janakiraman:

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

—

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) Chandra’s background

(04:47) The importance of strategy

(12:40) Defining product strategy

(15:42) Developing a winning strategy: an overview

(18:51) The preparation phase

(30:46) The strategy sprint process

(45:51) The design sprint

(51:19) Document writing

(57:39) Rolling out your strategy

(01:01:28) Resourcing and roadmapping

(01:04:42) Strategy lessons from Zynga

(01:11:34) Strategy lessons from Meta

(01:15:55) Big S strategy

(01:26:58) AI in strategy formulation

(01:38:12) Final thoughts and lightning round

—

Referenced:

• Headspace: https://www.headspace.com/

• Good Strategy, Bad Strategy | Richard Rumelt: https://www.lennysnewsletter.com/p/good-strategy-bad-strategy-richard

• 5 essential questions to craft a winning strategy | Roger Martin (author, advisor, speaker): https://www.lennysnewsletter.com/p/the-ultimate-guide-to-strategy-roger-martin

• VRChat: https://hello.vrchat.com/

• Andrew Chen on LinkedIn: https://www.linkedin.com/in/pmandrewchen/

• Template: Working Backwards PR FAQ: https://www.workingbackwards.com/resources/working-backwards-pr-faq

• How LinkedIn became interesting: The inside story | Tomer Cohen (CPO at LinkedIn): https://www.lennysnewsletter.com/p/how-linkedin-became-interesting-tomer-cohen

• Making time for what matters | Jake Knapp and John Zeratsky (authors of Sprint and Make Time, co-founders of Character Capital): https://www.lennysnewsletter.com/p/making-time-for-what-matters-jake

• Identify your bullseye customer in one day | Michael Margolis (UX Research Partner at Google Ventures): https://www.lennysnewsletter.com/p/finding-your-bullseye-customer-michael-margolis

• Chandra’s flow chart: https://docs.google.com/document/d/1SLmQ0oRFadzJnNM3MJetnLUvB18U4W4GXU4KtJ2ujEQ/edit?tab=t.0

• Chandra’s strategy template: https://docs.google.com/document/d/1iNeYUaMnpicvkpVZO-gj9cCxLeHfWN0xtGm_QoxgemE/edit?tab=t.0#heading=h.5d3jz6v86yrs

• Zynga: https://www.zynga.com/

• David Foster Wallace’s quote about water: https://www.goodreads.com/quotes/97082-there-are-these-two-young-fish-swimming-along-and-they

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

• Elon Musk’s quote: https://www.youtube.com/shorts/wf8TadbGYok

• Concept car: https://en.wikipedia.org/wiki/Concept_car

• Acquired podcast: The Mark Zuckerberg interview: https://www.acquired.fm/episodes/the-mark-zuckerberg-interview

• Armand Ruiz on LinkedIn: https://www.linkedin.com/in/armand-ruiz/

• What is a multi-armed bandit? Full explanation: https://amplitude.com/explore/experiment/multi-armed-bandit

• IF on Prime Video: https://www.amazon.com/IF-John-Krasinski/dp/B0CW19SCVW

• Dune: Part 2 on AppleTV+: https://tv.apple.com/us/movie/dune-part-two/umc.cmc.363aycnv6vy9qgekvew6fveb9

• Dune Prophecy on Max: https://www.max.com/shows/dune-prophecy-2024/57660b16-a32a-476f-89da-3302ac379e91

• Capybara Go on the App Store: https://apps.apple.com/ph/app/capybara-go/id6596787726

• Bluesky: https://bsky.app/

• Steve Jobs: The Lost Interview on Prime Video: https://www.amazon.com/Steve-Jobs-Lost-Interview/dp/B01IJD1BES

—

Recommended books:

• The Art of War: https://www.amazon.com/Art-War-Sun-Tzu/dp/1599869772

• Competitive Strategy: Techniques for Analyzing Industries and Competitors: https://www.amazon.com/Competitive-Strategy-Techniques-Industries-Competitors/dp/0684841487/

• Good Strategy Bad Strategy: The Difference and Why It Matters: https://www.amazon.com/Good-Strategy-Bad-Difference-Matters/dp/0307886239/

• Playing to Win: How Strategy Really Works: https://www.amazon.com/Playing-Win-Strategy-Really-Works/dp/142218739X

• Make Time: How to Focus on What Matters Every Day: https://www.amazon.com/Make-Time-Focus-Matters-Every/dp/0525572422

• Sprint: https://www.amazon.com/SPRINT-Jake-Zeratsky-Knapp/dp/0593076117

• Walt Disney: The Triumph of the American Imagination: https://www.amazon.com/Walt-Disney-Triumph-American-Imagination/dp/0679757473

• 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 Ten Faces of Innovation: Strategies for Heightening Creativity: https://www.amazon.com/dp/0385512074

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

—

Lenny may be an investor in the companies discussed.

Elena Verna is one of Silicon Valley’s most sought-after growth advisors and operators. She previously led growth at companies like Amplitude, Miro, Dropbox, and SurveyMonkey and is currently doing full-time advising for high-growth tech companies. In our conversation, Elena and I discuss:

• 10 growth tactics that never work

• Her 3 favorite growth frameworks

• How to increase your career optionality

—

Brought to you by:

• Sinch—Build messaging, email, and calling into your product

• Vanta—Automate compliance. Simplify security

• OneSchema—Import CSV data 10x faster

—

Find the transcript at: https://www.lennysnewsletter.com/p/10-growth-tactics-that-never-work-elena-verna

—

Where to find Elena Verna:

• Newsletter: https://www.elenaverna.com/

• X: https://x.com/elenaverna

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

—

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) Welcome back, Elena!

(06:02) Common mistakes growth teams make

(08:31) #1: Hiring for growth roles too soon

(15:09) #2: Hiring a head of growth to fix your problems

(19:20) #3: Doing a rebrand to drive growth

(25:11) #4: Obsessing over your competition

(34:00) #5: Believing that your problems are unique

(42:32) #6: Prioritizing other growth channels above earned channels

(50:55) #7: Failing to evolve your growth model

(01:01:06) #8: Not hiring advisors

(01:05:55) #9: Over-experimenting

(01:10:44) #10: Color optimizations, third-party signups, one-email wonders, and removing friction

(01:15:00) Elena’s favorite growth frameworks

(01:18:50) Contrarian corner: full-time jobs

(01:26:05) Lightning round and final thoughts

—

Referenced:

• Elena Verna on how B2B growth is changing, product-led growth, product-led sales, why you should go freemium not trial, what features to make free, and much more: https://www.lennysnewsletter.com/p/elena-verna-on-why-every-company

• The ultimate guide to product-led sales | Elena Verna: https://www.lennysnewsletter.com/p/the-ultimate-guide-to-product-led

• Six rules of hiring for growth: https://www.lennysnewsletter.com/p/hiring-growth

• Figma: https://www.figma.com/

• Miro: https://www.figma.com/

• Notion: https://www.figma.com/

• Carol Wong on LinkedIn: https://www.linkedin.com/in/carol-wong-14133927/

• Dropbox: https://www.dropbox.com/

• The Law of Shitty Clickthroughs: https://andrewchen.com/the-law-of-shitty-clickthroughs/

• Miroverse: https://miro.com/miroverse/

• GitHub: https://github.com/

• My 9 Favorite Growth Frameworks: https://www.elenaverna.com/p/my-9-favorite-growth-frameworks

• Growth Loops are the New Funnels: https://www.reforge.com/blog/growth-loops

• Racecar Growth Framework: https://www.reforge.com/blog/racecar-growth-framework

• The Adjacent User: https://andrewchen.com/the-adjacent-user-theory/

• Unorthodox frameworks for growing your product, career, and impact | Bangaly Kaba (YouTube, Instagram, Facebook, Instacart): https://www.lennysnewsletter.com/p/frameworks-for-growing-your-career-bangaly-kaba

• Why I’m Unquitting Full-Time Roles: https://www.elenaverna.com/p/why-im-unquitting-full-time-roles

• Noah Smith’s newsletter: https://www.noahpinion.blog/

• Beef on Netflix: https://www.netflix.com/title/81447461

• Veep on Max: https://www.max.com/shows/veep/37cb4217-c710-4166-8e9f-352a61f2cd3a

• The Last of Us on Max: https://www.max.com/shows/last-of-us/93ba22b1-833e-47ba-ae94-8ee7b9eefa9a

• Heated boots: https://www.amazon.com/heated-boots/s?k=heated+boots

• Airpods Max: https://www.apple.com/airpods-max/

• Memes by Elena: https://www.elenaverna.com/p/ten-funniest-growth-memes

—

Recommended books:

• Project Hail Mary: https://www.amazon.com/Project-Hail-Mary-Andy-Weir/dp/0593135229/

• The Martian: https://www.amazon.com/Martian-Andy-Weir/dp/0553418025

• We Are Legion (Bobiverse #1): https://www.amazon.com/We-Are-Legion-Bob-Bobiverse/dp/1680680587

• Fire Upon the Deep: https://www.amazon.com/Fire-Upon-Deep-Zones-Thought/dp/0812515285

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

—

Lenny may be an investor in the companies discussed.

Graham Weaver teaches a top-rated course at Stanford’s Graduate School of Business (GSB), where he often unexpectedly ends up helping students figure out what to do with their lives. He is also the founder and CEO of Alpine Investors, a people-driven private equity firm. In our conversation, we discuss:

• Why everything worthwhile requires suffering

• Why most people operate on autopilot, and how to break free

• The “genie methodology” for discovering your true path

• The Nine Lives exercise for exploring different life possibilities

• How to overcome limiting beliefs that hold you back

• Why “not now” is often just another way of saying “never”

• More

—

Brought to you by:

• Merge—A single API to add hundreds of integrations into your app

• Persona—A global leader in digital identity verification

• Liveblocks—Ready-made collaborative features to drop into your product

—

Find the transcript at: https://www.lennysnewsletter.com/p/how-to-break-out-of-autopilot-graham-weaver

—

Where to find Graham Weaver:

• LinkedIn: https://www.linkedin.com/in/graham-weaver-2b79

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

• YouTube: https://www.youtube.com/@grahamcweaver

• Website: https://www.grahamweaver.com

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

—

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) Graham’s background

(05:30) Helping students find their true path

(07:40) The genie methodology

(12:36) Breaking free from autopilot mode

(17:54) Identifying and overcoming limiting beliefs

(20:33) Teaching entrepreneurship and personal fulfillment

(22:53) The reality of long-term success

(35:14) The role of accountability and executive coaching

(40:22) Daily goal setting for success

(43:11) The Nine Lives framework

(48:01) The dangers of the “not now” mentality

(55:27) Navigating life’s transitions

(57:19) Failure corner

(01:00:24) When to quit and when to persevere

(01:02:18) Final thoughts and lightning round

—

Referenced:

• Setting Goals: Demystified: https://www.grahamweaver.com/blog/goals

• Tony Robbins’s website: https://www.tonyrobbins.com

• Alpine Investors: https://alpineinvestors.com

• Stanford GSB Last Lecture 2024—How to Live Your Life at Full Power: https://www.grahamweaver.com/blog/stanford-graduate-business-school-last-lecture-2024

• I turned 50 today. Here is the most important thing I learned in my first half century: https://www.grahamweaver.com/blog/turning-50

• Where the Crawdads Sing on Prime Video: https://www.amazon.com/Where-Crawdads-Sing-Daisy-Edgar-Jones/dp/B0B5KBKDNL

• Chilipad Cube Bed Cooling System: https://www.amazon.com/Chilipad-Cube-Bed-Cooling-System/dp/B07GT9MYRW

• Sleepme OOLER Sleep System: https://www.amazon.com/OOLER-Sleep-System-Temperature-Integration/dp/B07RX8LT9G

• Eightsleep: https://www.eightsleep.com

• Howard Thurman’s quote: https://www.goodreads.com/quotes/6273-don-t-ask-what-the-world-needs-ask-what-makes-you

—

Recommended books:

• Switch: How to Change Things when Change Is Hard: https://www.amazon.com/Switch-Change-Things-When-Hard/dp/0385528752

• The Untethered Soul: The Journey Beyond Yourself: https://www.amazon.com/Untethered-Soul-Journey-Beyond-Yourself/dp/1572245379

• Don’t Believe Everything You Think: Why Your Thinking Is the Beginning and End of Suffering: https://www.amazon.com/Dont-Believe-Everything-Think-Expanded/dp/B0D47VYQMY

• How to Win Friends and Influence People: https://www.amazon.com/How-Win-Friends-Influence-People/dp/0671027034

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

—

Lenny may be an investor in the companies discussed.

Rohini Pandhi is a product leader at Mercury, and previously spent over seven years at Square/Block leading product work on Square payments, invoicing, and the Bitkey hardware Bitcoin wallet. She’s also the co-founder of the startup bootcamp Transparent Collective and is an active angel investor. In our conversation, we discuss:

• Key indicators that it’s time to hire PMs

• How to build your early PM team

• Why founders should initially take on the product manager role themselves

• How to attract top PM talent

• What she’s learned about going multi-product

• A case for investing in quality

• More

—

Skip the Mercury Personal waitlist: https://mercurytechnologies.typeform.com/lenny

—

Brought to you by:

• Cloudinary—The foundational technology for all images and video on the internet

• OneSchema—Import CSV data 10x faster

• Airtable ProductCentral—Launch to new heights with a unified system for product development

—

Find the transcript at: https://www.lennysnewsletter.com/p/how-to-build-your-product-team-from-scratch-rohini-pandhi

—

Where to find Rohini Pandhi:

• X: https://x.com/rohinip

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

—

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) Rohini’s background

(05:00) The role of product managers at Mercury

(09:51) Key indicators that it’s time to hire PMs

(13:18) Building the product team at Mercury

(19:53) Why you should avoid hiring PMs too early

(22:26) The different flavors of product management

(26:15) How to attract top talent

(35:59) Advocating for quality in product development

(44:10) Going multi-product

(46:37) Organizational structure for multi-product success

(50:57) Organizational culture for multi-product success

(52:07) Customer obsession and product development

(57:36) More lessons from going multi-product

(01:05:57) Transparent Collective: supporting underrepresented founders

(01:09:54) Lightning round

—

Referenced:

• Immad Akhund on X: https://x.com/immad

• Mercury: https://mercury.com

• Square: https://squareup.com

• Product management career ladders: https://www.lennysnewsletter.com/p/product-management-career-ladders

• Pioneers, Settlers, Town Planners [Wardley]: https://orghacking.com/pioneers-settlers-town-planners-wardley-9dcd3709cde7

• Jason Zhang on LinkedIn: https://www.linkedin.com/in/jason-zhang-5645a860

• What is ‘Dogfooding’?: https://www.nytimes.com/2022/11/14/business/dogfooding.html

• Mercury Bill Pay: https://mercury.com/bill-pay

• Zip: https://zip.co

• Jira: https://www.atlassian.com/software/jira

• The art and science of pricing | Madhavan Ramanujam (Monetizing Innovation, Simon-Kucher): https://www.lennysnewsletter.com/p/the-art-and-science-of-pricing-madhavan

• Gokul Rajaram on designing your product development process, when and how to hire your first PM, a playbook for hiring leaders, getting ahead in you career, how to get started angel investing, more: https://www.lennysnewsletter.com/p/gokul-rajaram-on-designing-your-product

• Gokul Rajaram on X: https://x.com/gokulr

• Transparent Collective: https://www.transparentcollective.com

• 16 Reading Tips from Naval Ravikant: https://alexandbooks.com/archive/16-reading-tips-from-naval-ravikant

• Shrinking on AppleTV+: https://tv.apple.com/us/show/shrinking

• Bad Sisters on AppleTV+: https://tv.apple.com/us/show/bad-sisters

• Slow Horses on AppleTV+: https://tv.apple.com/us/show/slow-horses

• Severance on AppleTV+: https://tv.apple.com/us/show/severance

• Presumed Innocent on AppleTV+: https://tv.apple.com/us/show/presumed-innocent

• Waymo: https://waymo.com

• Adam Robinson on X: https://x.com/IAmAdamRobinson

• Cyan Banister—From Homeless and Broke to Top Angel Investor (Uber, SpaceX, and 100+ More): https://tim.blog/2024/11/28/cyan-banister

• Bobby Matson on LinkedIn: https://www.linkedin.com/in/bobbymatson

• Jobs at Mercury: https://mercury.com/jobs

—

Recommended books:

• Vectors: Aphorisms & Ten-Second Essays: https://www.amazon.com/Vectors-Aphorisms-Ten-Second-James-Richardson/dp/0967266890

• The Inner Game of Tennis: The Classic Guide to the Mental Side of Peak Performance: https://www.amazon.com/Inner-Game-Tennis-Classic-Performance/dp/0679778314

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

• Cutting for Stone: https://www.amazon.com/Cutting-Stone-Abraham-Verghese/dp/0375714367

• The Song of Achilles: https://www.amazon.com/Song-Achilles-Novel-Madeline-Miller/dp/0062060627

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

—

Lenny may be an investor in the companies discussed.

Drew Houston is the co-founder and CEO of Dropbox. Under his leadership, Dropbox has grown from a simple idea to a service used by over 700 million registered users globally, with a valuation exceeding $9 billion. Drew has led Dropbox through multiple phases, from explosive viral growth, to battling all the tech giants at once, to reinventing the company for the future of work. In our conversation, he opens up about:

• The three eras of Dropbox’s growth and evolution

• The challenges he’s faced over the past 18 years

• What he learned about himself

• How he’s been able to manage his psychology as a founder

• The importance of maintaining your learning curve

• Finding purpose beyond metrics and growth

• The micro, macro, and meta aspects of building companies

• Much more

—

Brought to you by:

• Paragon—Ship every SaaS integration your customers want

• Explo—Embed customer-facing analytics in your product

• Vanta—Automate compliance. Simplify security

—

Find the transcript at: https://www.lennysnewsletter.com/p/behind-the-founder-drew-houston-dropbox

—

Where to find Drew Houston:

• X: https://x.com/drewhouston

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

—

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) Introduction to Drew and Dropbox

(04:44) The three eras of Dropbox

(07:53) The first era: Viral growth and early success

(14:19) The second era: Challenges and competition

(20:49) Strategic shifts and refocusing

(29:36) Personal reflections and leadership lessons

(40:19) Unlocking mindfulness and building support systems

(43:14) The Enneagram test

(50:35) The challenges of being a founder CEO

(58:11) The third era: Rebooting the team and core business

(01:22:41) Lessons and advice for aspiring founders

(01:27:46) Balancing personal and professional growth

(01:42:38) Final reflections and future outlook

—

Referenced:

• Dropbox: https://www.dropbox.com/

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

• Paul Graham’s website: https://www.paulgraham.com/

• Hacker News: https://news.ycombinator.com/

• Arash Ferdowsi on LinkedIn: https://www.linkedin.com/in/arashferdowsi/

• Sequoia Capital: https://www.sequoiacap.com/

• Pejman Nozad on LinkedIn: https://www.linkedin.com/in/pejman/

• Mike Moritz on LinkedIn: https://www.linkedin.com/in/michaelmoritz/

• TechCrunch Disrupt: https://techcrunch.com/events/tc-disrupt-2024/

• Dropbox viral demo: https://youtu.be/7QmCUDHpNzE

• Digg: https://digg.com/

• Reddit: https://www.reddit.com/

• Hadi and Ali Partovi: https://www.partovi.org/

• Zynga: https://www.zynga.com/

• Steve Jobs announces Apple’s iCloud: https://www.youtube.com/watch?v=ilnfUa_-Rbc

• Dropbox Carousel: https://en.wikipedia.org/wiki/Dropbox_Carousel

• Dropbox Is Buying Mega-Hyped Email Startup Mailbox: https://www.businessinsider.com/dropbox-is-buying-mega-hyped-email-startup-mailbox-2013-3

• 5 essential questions to craft a winning strategy | Roger Martin (author, advisor, speaker): https://www.lennysnewsletter.com/p/the-ultimate-guide-to-strategy-roger-martin

• Intel: https://www.intel.com/

• Gordon Moore: https://en.wikipedia.org/wiki/Gordon_Moore

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

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

• Bill Campbell: https://en.wikipedia.org/wiki/Bill_Campbell_(business_executive)

• Enneagram type descriptions: https://www.enneagraminstitute.com/type-descriptions/

• The Myers-Briggs Type Indicator: https://www.themyersbriggs.com/en-US/Products-and-Services/Myers-Briggs

• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach

• Ben Horowitz on X: https://x.com/bhorowitz

• Why Read Peter Drucker?: https://hbr.org/2009/11/why-read-peter-drucker

• GitLab: https://about.gitlab.com/

• Automattic: https://automattic.com/

• Dropbox Dash: https://www.dash.dropbox.com/

• Welcome Command E to Dropbox: https://blog.dropbox.com/topics/company/welcome-command-e-to-dropbox-

• StarCraft: https://en.wikipedia.org/wiki/StarCraft_(video_game)

• Procter & Gamble and the Beauty of Small Wins: https://hbr.org/2009/10/the-beauty-of-small-wins

• Teaching Smart People How to Learn: https://hbr.org/1991/05/teaching-smart-people-how-to-learn

—

Recommended books:

• Guerrilla Marketing: Easy and Inexpensive Strategies for Making Big Profits from Your Small Business: https://www.amazon.com/Guerilla-Marketing-Inexpensive-Strategies-Business/dp/0618785914

• Playing to Win: How Strategy Really Works: https://www.amazon.com/Playing-Win-Strategy-Really-Works/dp/142218739X

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

• Only the Paranoid Survive: How to Exploit the Crisis Points That Challenge Every Company: https://www.amazon.com/Only-Paranoid-Survive-Exploit-Challenge/dp/0385483821

• Zone to Win: Organizing to Compete in an Age of Disruption: https://www.amazon.com/Zone-Win-Organizing-Compete-Disruption/dp/1682302113

• Warren Buffett’s books: https://www.amazon.com/warren-buffett-Books/s?k=warren+buffett&rh=n%3A283155

• Poor Charlie’s Almanack: The Essential Wit and Wisdom of Charles T. Munger: https://www.amazon.com/Poor-Charlies-Almanack-Essential-Charles/dp/1953953239

• Invent and Wander: The Collected Writings of Jeff Bezos: https://www.amazon.com/Invent-Wander-Collected-Writings-Introduction/dp/1647820715/

• The 15 Commitments of Conscious Leadership: A New Paradigm for Sustainable: https://www.amazon.com/15-Commitments-Conscious-Leadership-Sustainable-ebook/dp/B00R3MHWUE

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

—

Lenny may be an investor in the companies discussed.

Alisa Cohn is an executive coach who has worked with C-suite executives at startups like Venmo, Etsy, Wirecutter, and DraftKings, and Fortune 500 companies like Microsoft, Google, Pfizer, Dell, and IBM. Inc. Magazine named Alisa one of the top 100 leadership speakers, and she was named one of the Top 50 coaches in the world by Thinkers50 and the #1 startup coach for the past four years by Global Gurus. She is also the author of From Start-Up to Grown-Up, which won the 2022 Independent Press Award and the American Book Fest 2023 Best Book Award for Entrepreneurship, and is the creator and host of a podcast of the same name. In our conversation, we discuss:

• The psychology behind why we avoid difficult conversations

• Specific scripts for having five common difficult conversations

• How to handle defensive reactions in the moment

• The three questions you should end every meeting with

• “The founder prenup” that every founding team should work through

• Common leadership myths

• Stories of failure from Alisa’s career

—

Brought to you by:

• Eppo—Run reliable, impactful experiments

• Rippling—Automate HR, IT, and finance so you can scale faster

• Liveblocks—Ready-made collaborative features to drop into your product

—

Find the transcript at: https://www.lennysnewsletter.com/p/scripts-for-difficult-conversations-alisa-cohn

—

Where to find Alisa Cohn:

• X: https://x.com/AlisaCohn

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

• Website: https://www.alisacohn.com

• Podcast: https://www.alisacohn.com/podcast

—

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) Alisa’s background

(04:48) Having difficult conversations

(12:48) Scripts for performance feedback

(20:20) How to respond when someone is defensive or upset

(25:07) Scripts for handling promotion disappointments

(31:00) Scripts for handling terminations

(35:44) The importance of positive feedback

(38:49) Understanding your job as a leader

(44:55) Recognizing your own blind spots

(49:38) Three vital questions to ask in every meeting

(55:57) The founder prenup

(01:08:24) Failure corner

(01:13:00) Final thoughts and lightning round

—

Referenced:

• Alisa’s free PDF downloads for Lenny’s listeners: https://www.alisacohn.com/Lenny/

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

• Non-Violent Communication (NVC) Model: https://www.ucop.edu/ombuds/_files/nvc-model-requesting-change-remove.pdf

• Sheryl Sandberg on LinkedIn: https://www.linkedin.com/in/sheryl-sandberg-5126652

• How embracing emotions will accelerate your career | Joe Hudson (executive coach, Art of Accomplishment): https://www.lennysnewsletter.com/p/embracing-your-emotions-joe-hudson

• Joe Gebbia on X: https://x.com/jgebbia

• Noam Wasserman on LinkedIn: https://www.linkedin.com/in/noam-wasserman-462425

• Core Values List: https://jamesclear.com/core-values

• How Cofounders Can Prevent Their Relationship from Derailing: https://hbr.org/2022/04/how-cofounders-can-prevent-their-relationship-from-derailing

• Inside Out 2 on Disney+: https://www.disneyplus.com/movies/inside-out-2/6MeZYf9JkFii

• Ninja CREAMi: https://www.amazon.com/Ninja-NC299AMZ-Milkshakes-One-Touch-Container/dp/B09QV24FFZ

• Joseph Campbell quote: https://www.goodreads.com/quotes/136819-if-the-path-before-you-is-clear-you-re-probably-on

—

Recommended books:

• From Start-Up to Grown-Up: Grow Your Leadership to Grow Your Business: https://www.amazon.com/Start-Up-Grown-Up-Grow-Leadership-Business/dp/1398601403

• Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity: https://www.amazon.com/Radical-Candor-Revised-Kick-Ass-Humanity/dp/1250235375

• Working Backwards: Insights, Stories, and Secrets from Inside Amazon: https://www.amazon.com/Working-Backwards-Insights-Stories-Secrets/dp/1250267595

• Unpacking Amazon’s unique ways of working | Bill Carr (author of Working Backwards): https://www.lennysnewsletter.com/p/unpacking-amazons-unique-ways-of

• Walt Disney: The Triumph of the American Imagination: https://www.amazon.com/Walt-Disney-Triumph-American-Imagination/dp/0679757473

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

—

Lenny may be an investor in the companies discussed.

Eilon Reshef is the co-founder and chief product officer at Gong, one of the most ubiquitous B2B products in the world. In our conversation, we discuss:

• Gong’s unique approach to working with design partners

• Their unique pod model

• Why Eilon makes big decisions quickly

• Lessons learned from being early in AI

• The power of extreme focus

• His “spiral method” for learning complex topics quickly

• How to maintain quality while optimizing for speed

—

Brought to you by:

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

• Think Fast Talk Smart—Tools and techniques to help you communicate more effectively

• Vanta—Automate compliance. Simplify security

—

Find the transcript at: https://www.lennysnewsletter.com/p/inside-gong-eilon-reshef

—

Where to find Eilon Reshef:• LinkedIn: https://www.linkedin.com/in/eilonreshef

—

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) Eilon’s background

(04:20) The pod model

(06:33) Working with design partners

(09:13) Finding and coordinating design partners

(13:12) Balancing customer feedback and vision

(15:10) Gong's 95% feature adoption

(17:05) The importance of autonomy and trust

(23:30) How to implement this unique way of working

(27:15) Speed and decision-making

(31:47) Early AI adoption and lessons learned

(35:50) Building effective AI teams

(38:16) The spiral method for learning

(41:36) Narrowing down the initial customer profile

(44:24) Failure corner

(46:35) Lightning round

—

Referenced:

• Gong: https://www.gong.io

• Cisco: https://www.cisco.com/

• How Gong builds product: https://www.lennysnewsletter.com/p/how-gong-builds-product

• What is Montessori education?: https://amshq.org/About-Montessori/What-Is-Montessori

• Isaac Asimov: https://en.wikipedia.org/wiki/Isaac_Asimov

• Amit Bendov on LinkedIn: https://www.linkedin.com/in/amitbendov/

• Lessons from scaling Spotify: The science of product, taking risky bets, and how AI is already impacting the future of music | Gustav Söderström (Co-President, CPO, and CTO at Spotify): https://www.lennysnewsletter.com/p/lessons-from-scaling-spotify-the

• Nvidia: https://www.nvidia.com

• Figma: https://www.figma.com

• The Spiral Method: https://www.gong.io/blog/using-the-spiral-method/

• Webex: https://www.webex.com/

• L’Oréal: https://www.lorealparisusa.com/

• American Express: https://www.americanexpress.com/

• Slow Horses on AppleTV+: https://tv.apple.com/us/show/slow-horses/umc.cmc.2szz3fdt71tl1ulnbp8utgq5o

• Dishwasher basket: https://www.amazon.com/Munchkin-High-Capacity-Dishwasher-Basket/dp/B07ZPMYKKS/

• What most people miss about marketing | Rory Sutherland (Vice Chairman of Ogilvy UK, author): https://www.lennysnewsletter.com/p/what-most-people-miss-about-marketing

• Occam’s razor: https://en.wikipedia.org/wiki/Occam%27s_razor

• Hanlon’s razor: https://en.wikipedia.org/wiki/Hanlon%27s_razor

• Sabich: https://en.wikipedia.org/wiki/Sabich#Ingredients_and_description

• Careers at Gong: https://www.gong.io/careers

—

Recommended books:

• Marty Cagan’s books: https://www.amazon.com/stores/Marty-Cagan/author/B00J21JTNM

• “The Machine That Won the War”: https://www.goodreads.com/book/show/18402398-the-machine-that-won-the-war

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

• The Ideal Executive: https://www.amazon.com/Ideal-Executive-Ichak-Kalderon-Adizes/dp/0937120030/

• Crucial Conversations: Tools for Talking when Stakes Are High: https://www.amazon.com/Crucial-Conversations-Tools-Talking-Stakes/dp/1260474186/

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

—

Lenny may be an investor in the companies discussed.

Shaun Clowes is the chief product officer at Confluent and former CPO at Salesforce’s MuleSoft and at Metromile. He was also the first head of growth at Atlassian, where he led product for Jira Agile and built the first-ever B2B growth team. In our conversation, we discuss:

• Why most PMs are bad, and how to fix this

• Why great AI products are all about the data

• Why he changed his mind about being data-driven

• How to build your B2B growth team

• How to choose your next career stop

• Much more

—

Brought to you by:

• Enterpret—Transform customer feedback into product growth

• BuildBetter—AI for product teams

• Wix Studio—The web creation platform built for agencies

—

Find the transcript at: https://www.lennysnewsletter.com/p/why-great-ai-products-are-all-about-the-data-shaun-clowes

—

Where to find Shaun Clowes:

• X: https://x.com/ShaunMClowes

• LinkedIn: https://www.linkedin.com/in/shaun-clowes-80795014/

• Website: https://shaunclowes.com/about-shaun

• Reforge: https://www.reforge.com/profiles/shaun-clowes

—

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) Shaun’s background

(05:08) The state of product management

(09:33) Becoming a 10x product manager

(13:23) Specific ways to leverage AI in product management

(17:15) Feedback rivers

(19:20) AI's impact on data management

(24:35) The future of enterprise businesses with AI

(35:41) Data-driven decision-making

(45:50) Building effective growth teams

(50:18) The evolution of product-led growth

(56:16) Career insights and decision-making

(01:07:45) Failure corner

(01:12:32) Final thoughts and lightning round

—

Referenced:

• Steve Blank’s website: https://steveblank.com/

• Getting Out of the Building. 2 Minutes to See Why: https://www.youtube.com/watch?v=TbMgWr1YVfs

• OpenAI: https://openai.com/

• Claude: https://claude.ai/

• Sachin Rekhi on LinkedIn: https://www.linkedin.com/in/sachinrekhi/

• Video: Building Your Product Intuition with Feedback Rivers: https://www.sachinrekhi.com/video-building-your-product-intuition-with-feedback-rivers

• Confluent: https://www.confluent.io

• Workday: https://www.workday.com/

• Lenny and Friends Summit: https://lennyssummit.com/

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

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

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

• Atlassian: https://www.atlassian.com/

• Jira: https://www.atlassian.com/software/jira

• Ashby: https://www.ashbyhq.com/

• Occam’s razor: https://en.wikipedia.org/wiki/Occam%27s_razor

• Breaking the rules of growth: Why Shopify bans KPIs, optimizes for churn, prioritizes intuition, and builds toward a 100-year vision | Archie Abrams (VP Product, Head of Growth at Shopify): https://www.lennysnewsletter.com/p/shopifys-growth-archie-abrams

• Charlie Munger quote: https://www.goodreads.com/quotes/11903426-show-me-the-incentive-and-i-ll-show-you-the-outcome

• Elena Verna on how B2B growth is changing, product-led growth, product-led sales, why you should go freemium not trial, what features to make free, and much more: https://www.lennysnewsletter.com/p/elena-verna-on-why-every-company

• The ultimate guide to product-led sales | Elena Verna: https://www.lennysnewsletter.com/p/the-ultimate-guide-to-product-led

• Metromile: https://www.metromile.com/

• Tom Kennedy on LinkedIn: https://www.linkedin.com/in/tom-kennedy-37356b2b/

• Building Wiz: the fastest-growing startup in history | Raaz Herzberg (CMO and VP Product Strategy): https://www.lennysnewsletter.com/p/building-wiz-raaz-herzberg

• Wiz: https://www.wiz.io

• Colin Powell’s 40-70 rule: https://www.42courses.com/blog/home/2019/12/10/colin-powells-40-70-rule

• Detroiters on Netflix: https://www.netflix.com/title/80165019

• Glean: https://www.glean.com/

• Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity: https://www.amazon.com/Radical-Candor-Kick-Ass-Without-Humanity/dp/1250103509

• Listen: Five Simple Tools to Meet Your Everyday Parenting Challenges: https://www.amazon.com/Listen-Simple-Everyday-Parenting-Challenges/dp/0997459301

• Empress Falls Canyon and abseiling: https://bmac.com.au/blue-mountains-canyoning/empress-falls-canyon-and-abseiling

—

Recommended books:

• The Lean Startup: How Today’s Entrepreneurs Use Continuous Innovation to Create Radically Successful Businesses: https://www.amazon.com/Lean-Startup-Entrepreneurs-Continuous-Innovation/dp/0307887898

• Inspired: How to Create Products Customers Love: https://www.amazon.com/Inspired-Create-Products-Customers-Love/dp/0981690408

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

—

Lenny may be an investor in the companies discussed.

Marc Benioff is the co-founder and CEO of Salesforce, the second-largest software company in the world. He started programming at age 15, selling his first program for $75, and went on to build Salesforce into a company worth more than $300 billion that also owns Slack, Tableau, Quip, and MuleSoft. Marc is known as a marketing legend, and is now leading Salesforce into the era of AI agents. In our conversation, we discuss:

• The importance of maintaining a beginner’s mind

• His approach to product launches and marketing

• Managing through tough times and layoffs

• His relationship with Steve Jobs and lessons learned

• Why Salesforce is betting big on AI agents

• Many stories from his entrepreneurial roller coaster

• Much more

—

Brought to you by:

• Cloudinary—The foundational technology for all images and video on the internet

• Enterpret—Transform customer feedback into product growth

• Coda—The all-in-one collaborative workspace

—

Find the transcript at: https://www.lennysnewsletter.com/p/behind-the-founder-marc-benioff

—

Where to find Marc Benioff:

• X: https://x.com/benioff

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

—

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) Introduction to Marc Benioff and Salesforce

(03:54) Marc’s early career and domain names

(05:59) The App Store story and lessons from Steve Jobs

(15:18) Lessons from launching Salesforce

(22:03) The importance of keeping a beginner’s mindset

(29:53) Why Marc calls Salesforce the “25-year startup”

(31:47) Agentforce

(36:09) Why Marc says AI is the defining technology of our lifetime

(40:12) AI’s impact on the workforce

(42:31) Entrepreneurs need to be like conductors

(46:02) Failure corner

(50:32) The future of AI agents

(56:34) Final thoughts and farewell

—

Referenced:

• Bill.com: https://www.bill.com

• App Store: https://www.apple.com/app-store/

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

• Oracle: https://www.oracle.com

• Larry Ellison on X: https://x.com/larryellison

• Siebel Systems: https://en.wikipedia.org/wiki/Siebel_Systems

• Saba Software: https://talentedlearning.com/lms-vendor-directory/saba-software

• Tom Siebel on LinkedIn: https://www.linkedin.com/in/thomassiebel

• Avon: https://www.avon.com

• Salesforce Chief Has Pulled Some Crazy Stunts: https://www.businessinsider.com/marc-benioff-salesforcecom-chief-has-pulled-some-crazy-stunts-2012-3

•  Matthew McConaughey on Instagram: https://www.instagram.com/officiallymcconaughey

• Woody Harrelson on Instagram: https://www.instagram.com/woodyharrelson

• “Ask More of AI” with Matthew McConaughey: https://www.youtube.com/playlist?list=PLnobS_RgN7JaxOsLD8WH0I9E6osK3UrfI

• Marc’s tweet about the ad with McConaughey and Harrelson: https://x.com/Benioff/status/1866175950062239784

• Chris Rock on Instagram: https://www.instagram.com/chrisrock

• Sushi Iwa: http://www.sushiiwa.jp/en/

• Ryoanji Temple Rock Garden: https://www.japan.travel/en/spot/1145/

• Neil Young Archives on Instagram: https://www.instagram.com/neilyoungarchives

• Mount Tam: https://en.wikipedia.org/wiki/Mount_Tamalpais

• Spirit Rock: https://www.spiritrock.org

• Jack Kornfield: https://www.spiritrock.org/teachers/jack-kornfield

• Agentforce: https://www.salesforce.com/form/agentforce/demo

• Minority Report on Prime: https://www.amazon.com/Minority-Report-Tom-Cruise/dp/B00A2FSSHK

• Peter Schwartz on X: https://x.com/peterschwartz2

• UCSF Health: https://www.ucsfhealth.org

• A.I. Chatbots Defeated Doctors at Diagnosing Illness: https://www.nytimes.com/2024/11/17/health/chatgpt-ai-doctors-diagnosis.html

• Does AI improve doctors’ diagnoses? Study puts it to the test: https://www.sciencedaily.com/releases/2024/11/241113123419.htm

• A.I. Will Transform the Global Economy—if Humans Let It: https://www.nytimes.com/2024/12/07/special-series/ai-transform-global-economy.html

• Wargames on Prime: https://www.amazon.com/Wargames-Dabney-Coleman/dp/B0011EQBOS

• Her on Prime: https://www.amazon.com/Her-Joaquin-Phoenix/dp/B00KATY250

• AI (Einstein) at Salesforce: https://www.salesforce.com/in/artificial-intelligence

• Salesforce Signs Definitive Agreement to Acquire Airkit.ai: https://www.salesforce.com/news/stories/salesforce-signs-definitive-agreement-to-acquire-airkit-ai

• Salesforce Buys Big Data Startup RelateIQ for Up to $390M: https://techcrunch.com/2014/07/11/salesforce-buys-big-data-startup-relateiq-for-up-to-390m

• Salesforce to cut workforce by 10% after hiring ‘too many people’ during the pandemic: https://techcrunch.com/2023/01/04/salesforce-to-cut-workforce-by-10-after-hiring-too-many-people-during-the-pandemic

• Michael Dell on LinkedIn: https://www.linkedin.com/in/mdell

• Bret Taylor on LinkedIn: https://www.linkedin.com/in/brettaylor

• Akio Toyoda: https://en.wikipedia.org/wiki/Akio_Toyoda

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

• TRS-80: https://en.wikipedia.org/wiki/TRS-80

• CLOAD Magazine: https://archive.org/details/cload_newsletter

—

Recommended books:

• Ghost Fleet: A Novel of the Next World War: https://www.amazon.com/Ghost-Fleet-Novel-Next-World/dp/054470505X

• Behind the Cloud: The Untold Story of How Salesforce.com Went from Idea to Billion-Dollar Company—and Revolutionized an Industry: https://www.amazon.com/Behind-Cloud-Salesforce-com-Billion-Dollar-Company/dp/0470521163

• Trailblazer: The Power of Business as the Greatest Platform for Change: https://www.amazon.com/Trailblazer-Business-Greatest-Platform-Change/dp/1984825194

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

—

Lenny may be an investor in the companies discussed.

Farhan Thawar is the head of engineering at Shopify, where he oversees more than 1,000 engineers and a platform that powers over 10% of all U.S. e-commerce. Before Shopify, he was VP of engineering at Pivotal Labs and Xtreme Labs, and co-founder of Helpful.com. In our conversation, Farhan shares:

• Why choosing the harder path leads to better outcomes

• How to create intensity within your org (without burnout)

• Why every company should be embracing pair programming

• How he hires without interviewing

• How he built the world’s largest internship program

• His mission to create a “crafter’s paradise” for engineers

• Much more

—

Brought to you by:

• DX—A platform for measuring and improving developer productivity

• Persona—A global leader in digital identity verification

• Vanta—Automate compliance. Simplify security

—

Find the transcript at: https://www.lennysnewsletter.com/p/how-shopify-builds-a-high-intensity-culture-farhan-thawer

—

Where to find Farhan Thawar:

• X: https://x.com/fnthawar

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

—

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) Farhan’s background

(05:38) Choosing the hard path

(09:37) Getting comfortable with looking dumb

(13:20) Lessons from working with visionaries

(19:19) Creating intensity in organizations

(22:06) The power of pair programming

(29:18) Shopify’s culture of intensity

(37:18) Meeting Armageddon: revolutionizing company meetings

(39:46) Reducing distractions

(41:10) Deleting 1M+ lines of code

(49:05) Three buckets of building

(57:45) Remote work and trust battery

(01:00:29) Finding stability in uncomfortable times

(01:03:14) Hiring philosophy

(01:11:41) Internship programs and co-op systems

(01:15:32) Lessons from managing 120 direct reports

(01:20:40) Failure corner

(01:27:46) Lightning round and closing thoughts

—

Referenced:

• The Steve Jobs quote about connecting dots: https://www.goodreads.com/quotes/463176-you-can-t-connect-the-dots-looking-forward-you-can-only

• Shopify: https://www.shopify.com/

• GitHub: https://github.com/

• Farhan’s “questions to ask” framework: https://x.com/fnthawar/status/1514193402828574721

• Palantir: https://www.palantir.com/

• Joe Liemandt: https://www.linkedin.com/in/liemandt

• Chamath Palihapitya: https://en.wikipedia.org/wiki/Chamath_Palihapitiya

• Xtreme Labs: https://www.xtremelabs.io

• Parkinson’s law: https://www.verywellmind.com/what-is-parkinsons-law-6674423

• Pair programming: https://dev.to/documatic/pair-programming-best-practices-and-tools-154j

• Cody Fauser on LinkedIn: https://www.linkedin.com/in/codyfauser

• How Shopify builds product: https://www.lennysnewsletter.com/p/how-shopify-builds-product

• Chaos Monkey: We look at Shopify’s new ‘culture of focus’: https://www.siliconrepublic.com/careers/shopify-chaos-monkey-meetings-culture-deann-evans

• Empowering devs with AI: How Shopify made GitHub Copilot core to its culture: https://www.youtube.com/watch?v=wVKBwcm5dbw&t=2318s

• Tobi Lütke of Shopify: Powering a Team with a ‘Trust Battery’: https://www.nytimes.com/2016/04/24/business/tobi-lutke-of-shopify-powering-a-team-with-a-trust-battery.html

• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach

• Stop Being Deceived by Interviews When You’re Hiring: https://www.forbes.com/sites/forbesleadershipforum/2012/02/07/stop-being-deceived-by-interviews-when-youre-hiring/

• Shopify’s made the Life Story a major part of their interview: https://news.ycombinator.com/item?id=39294140

• Internships at Shopify: https://internships.shopify.com

• Nick Adams on LinkedIn: https://www.linkedin.com/in/nick-adams-32b28139

• React Native: https://reactnative.dev

• Swift: https://www.swift.org

• Acquired podcast: The Mark Zuckerberg interview: https://www.acquired.fm/episodes/the-mark-zuckerberg-interview

• The Power of Performance Reviews: Use This System to Become a Better Manager: https://review.firstround.com/the-power-of-performance-reviews-use-this-system-to-become-a-better-manager

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

• The Secret to a Great Planning Process—Lessons from Airbnb and Eventbrite: https://review.firstround.com/the-secret-to-a-great-planning-process-lessons-from-airbnb-and-eventbrite

• How to do great work: https://www.paulgraham.com/greatwork.html

• Challengers on Prime: https://www.amazon.com/Challengers-Luca-Guadagnino/dp/B0CX5MZ9M4

• Halt and Catch Fire on Prime: https://www.amazon.com/Halt-Catch-Fire-Season-1/dp/B0CKXZNT96

• Meta Ray-Bans: https://www.meta.com/smart-glasses/shop-all

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

—

Recommended books:

• The Undoing Project: A Friendship That Changed Our Minds: https://www.amazon.com/Undoing-Project-Friendship-Changed-Minds/dp/0393254593

• Range: Why Generalists Triumph in a Specialized World: https://www.amazon.com/Range-Generalists-Triumph-Specialized-World/dp/0735214484

• Manna: Two Visions of Humanity’s Future: https://www.amazon.com/Manna-Two-Visions-Humanitys-Future-ebook/dp/B007HQH67U

• Business Adventures: Twelve Classic Tales from the World of Wall Street: https://www.amazon.com/Business-Adventures-Twelve-Classic-Street/dp/1504000021

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

—

Lenny may be an investor in the companies discussed.

Jackson Shuttleworth is a Group PM at Duolingo, where he leads the retention team and the powerful streak feature. The streak feature, which gamifies consecutive days of learning, has been Duolingo’s most important and innovative growth lever and a key driver of their growth to a $14 billion business with almost 600 million users. In our conversation, we dive deep into the history and lessons of this feature:

• The evolution of the streak feature

• Biggest insights from over 600 streak-related experiments

• Biggest specific wins and misses along the way

• Key principles for building effective streak mechanics

• How to operate a high-velocity product team

• Tips for building engaging notification systems

• Much more

—

Brought to you by:

• Pendo—The only all-in-one product experience platform for any type of application

• Vanta—Automate compliance. Simplify security

• Coda—The all-in-one collaborative workspace

—

Find the transcript at: https://www.lennysnewsletter.com/p/behind-the-product-duolingo-streaks

—

Where to find Jackson Shuttleworth:• LinkedIn: https://www.linkedin.com/in/jackson-shuttleworth/

—

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) Jackson’s background and an overview of Duolingo’s streak feature

(06:00) The impact of streaks on Duolingo’s success

(09:58) The origin and evolution of streaks

(14:50) Key experiments and insights

(24:38) User psychology and engagement strategies

(28:36) Duolingo’s product review structure

(33:07) Designing for clarity and adaptability

(46:59) Developing the Streak Freeze feature

(50:47) Balancing monetization and retention

(54:08) Notification strategies

(58:15) The Perfect Streak feature

(01:00:40) Enhancing the user experience 

(01:04:47) Team operations and experimentation

(01:18:57) Who can benefit from streaks

(01:21:00) Lightning round

—

Referenced:

• Duolingo streaks: https://duolingo.fandom.com/wiki/Streak

• How to make learning as addictive as social media: https://www.ted.com/talks/luis_von_ahn_how_to_make_learning_as_addictive_as_social_media?subtitle=en

• Luis von Ahn on LinkedIn: https://www.linkedin.com/in/luis-von-ahn-duolingo/

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

• Royal Match: https://www.dreamgames.com/games/royal-match

• How Duolingo reignited user growth: https://www.lennysnewsletter.com/p/how-duolingo-reignited-user-growth

• You’re on fire! Or, how we brought the streak milestone to life: https://blog.duolingo.com/streak-milestone-design-animation/

• Duolingo Doubles Down on Design and Animation with Acquisition of Hobbes: https://investors.duolingo.com/news-releases/news-release-details/duolingo-doubles-down-design-and-animation-acquisition-hobbes

• Hobbes: https://www.hobbes.work/

• Jira: https://www.atlassian.com/software/jira

• Atlassian: https://www.atlassian.com/

• Bing Gordon on LinkedIn: https://www.linkedin.com/in/binggordon/

• Peloton: https://www.onepeloton.com/

• Bluey on Disney+: https://www.disneyplus.com/series/bluey/1xy9TAOQ0M3r

• Emily in Paris on Netflix: https://www.netflix.com/title/81037371

• Multi-position ladders at Home Depot: https://www.homedepot.com/b/Building-Materials-Ladders-Multi-Position-Ladders/N-5yc1vZasew

—

Recommended books:

• A Guide to Midwestern Conversation: https://www.amazon.com/Guide-Midwestern-Conversation-Taylor-Phillips/dp/1984861336

• Fate Is the Hunter: A Pilot’s Memoir: https://www.amazon.com/Fate-Hunter-Ernest-K-Gann/dp/0671636030

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

—

Lenny may be an investor in the companies discussed.

Seth Godin is a legend. He’s a marketer, teacher, entrepreneur, and author of more than 20 books, including Purple Cow, Permission Marketing, and Linchpin. He also writes one of the most popular and longest-running blogs in the world (approaching publishing 10,000 in a row!) and continues to shape how we think about marketing, brand, product, and creating lasting change in the world. In our conversation, we discuss:

• How to build remarkable products that spread

• The four critical strategic choices that determine your future

• How to develop good taste and high standards

• The role of tension in great strategy

• How Seth used Claude to write his newest book

• Much more

—

Brought to you by:

• DX—A platform for measuring and improving developer productivity

• Vanta—Automate compliance. Simplify security

• Paragon—Ship every SaaS integration your customers want

—

Find the transcript at: https://www.lennysnewsletter.com/p/seth-godins-tactics-for-building-remarkable-products

—

Where to find Seth Godin:

• Blog: http://seths.blog/

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

• Website: https://www.sethgodin.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) Seth’s background

(05:17) Understanding good taste and upholding high standards

(08:09) Become the best at whatever you do

(09:48) Seth’s journey as a product manager

(14:09) What people often get wrong when building products

(16:00) Building a brand in the age of AI

(19:04) Using AI to enhance writing

(22:40) Four critical elements for an effective strategy

(27:38) The role of tension in strategy

(29:15) The concept of the purple cow

(33:11) "Safe is risky"

(34:56) The power of systems

(37:07) Better waves make better surfers

(38:10) Rebranding vs. re-logoing

(43:07) Empathetic leadership

(44:14) Conclusion and farewell

—

Referenced:

• Seth Godin on the Tim Ferriss Show: https://tim.blog/2024/03/20/seth-godin-3/

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

• Spinnaker: https://spinnaker.io

• Ray Bradbury: https://en.wikipedia.org/wiki/Ray_Bradbury

• Arthur C. Clarke: https://en.wikipedia.org/wiki/Arthur_C._Clarke

• Isaac Asimov: https://en.wikipedia.org/wiki/Isaac_Asimov

• Roger Zelazny: https://en.wikipedia.org/wiki/Roger_Zelazny

• Herbie Hancock: https://en.wikipedia.org/wiki/Herbie_Hancock

• Fahrenheit 451 (game): https://www.filfre.net/2013/09/fahrenheit-451-the-game/

• RTFM: https://en.wikipedia.org/wiki/RTFM#

• Intercom: https://www.intercom.com

• Claude: https://claude.ai

• ChatGPT: https://chatgpt.com

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

• Steam: https://store.steampowered.com

• P.F. Flyers: https://pfflyers.com

• Steve Blank’s website: https://steveblank.com

• Marissa Mayer on X: https://x.com/marissamayer

• Jaguar unveils new logo ahead of electric relaunch: https://www.bbc.com/news/articles/cgr0pw00n7qo

• IHOP Becomes IHOb, the International House of ... Burgers: https://www.npr.org/2018/06/11/618844977/ihop-becomes-ihob-the-international-house-of-burgers

• Oreo’s Super Bowl Power-Outage Tweet Was 18 Months in the Making: https://www.businessinsider.com/oreos-super-bowl-power-outage-tweet-was-18-months-in-the-making-2013-3

• Tesla’s New ‘Ludicrous Mode’ Makes the Model S a Supercar: https://www.wired.com/2015/07/teslas-new-ludicrous-mode-makes-model-s-supercar

—

Recommended books:

• This Is Strategy: Make Better Plans (Create a Strategy to Elevate Your Career, Community & Life): https://www.amazon.com/This-Strategy-Better-Elevate-Community/dp/B0D47T8S7N• Purple Cow: Transform Your Business by Being Remarkable: https://www.amazon.com/Purple-Cow-New-Transform-Remarkable/dp/1591843170

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

—

Lenny may be an investor in the companies discussed.

Jonathan Lowenhar is the co-founder of Enjoy The Work, an executive coaching firm that helps founders become great CEOs. Over the past decade, Enjoy The Work has supported over 165 founders on their journey to becoming better leaders. In our conversation, we discuss:

• The difference between being a founder and being a CEO

• Common failure modes for startup CEOs and how to avoid them

• The four key elements of an effective go-to-market strategy

• A framework for evaluating potential acquisitions: the magic box paradigm

• How to find and hire the best people

• How to build a repeatable GTM machine

• Why founders need to trust their intuition

• Much more

—

Brought to you by:

• Pendo—The only all-in-one product experience platform for any type of application

• OneSchema—Import CSV data 10x faster

• Vanta—Automate compliance. Simplify security

—

Find the transcript at: https://www.lennysnewsletter.com/p/how-a-great-founder-becomes-a-great-ceo-jonathan-lowenhar

—

Where to find Jonathan Lowenhar:

• X: https://x.com/jlowenhar

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

• Enjoy the Work: https://etw.live/lenny

—

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) Jonathan’s background

(02:56) Understanding the rhythm of well-run companies

(09:20) The founder mode vs. manager mode debate

(12:05) Common company failure modes

(13:36) Common CEO failure modes

(25:25) The magic box paradigm for selling your startup

(43:07) Advice for founders on building relationships

(49:28) Hiring and building an amazing team

(57:11) Types of executives: architect, optimizer, scaler

(59:45) Working backward in hiring

(01:02:54) Four key components of a go-to-market strategy

(01:15:01) Trusting founder intuition

(01:19:12) Founder vs. CEO: different roles, different skills

(01:20:52) Closing thoughts and lightning round

—

Referenced:

• Founder mode memes: https://techcrunch.com/2024/09/04/those-founder-mode-memes-keep-coming/

• Founder mode: https://paulgraham.com/foundermode.html

• “Founder Mode” Is a Dangerous Red Herring: https://enjoythework.com/founder-mode-is-a-dangerous-red-herring/

• Magic Box Paradigm: A Framework for Startup Acquisitions: https://www.amazon.com/Magic-Box-Paradigm-Framework-Acquisitions/dp/0692778047

• Facebook Buys Instagram for $1 Billion: https://archive.nytimes.com/dealbook.nytimes.com/2012/04/09/facebook-buys-instagram-for-1-billion/

• Chris Voss on X: https://x.com/fbinegotiator

• Who: https://www.amazon.com/Who-Geoff-Smart/dp/0345504194

• Brian Chesky on LinkedIn: https://www.linkedin.com/in/brianchesky/

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

• Nathan Blecharczyk on LinkedIn: https://www.linkedin.com/in/blecharczyk/

• 4 questions Shreyas Doshi wishes he’d asked himself sooner | Former PM leader at Stripe, Twitter, Google: https://www.lennysnewsletter.com/p/shreyas-doshi-live

• Traction: How Any Startup Can Achieve Explosive Customer Growth: https://www.amazon.com/Traction-Startup-Achieve-Explosive-Customer/dp/1591848369

• Adam Grant on LinkedIn: https://www.linkedin.com/in/adammgrant/

• 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

• How to identify your ideal customer profile (ICP): https://www.lennysnewsletter.com/p/how-to-identify-your-ideal-customer

• How to get your marketing team to drive more impact: https://www.lennysnewsletter.com/p/how-to-get-your-marketing-team-to

• The Five Dysfunctions of a Team: A Leadership Fable: https://www.amazon.com/Five-Dysfunctions-Team-Leadership-Fable/dp/0787960756

• The Untethered Soul: The Journey Beyond Yourself: https://www.amazon.com/Untethered-Soul-Journey-Beyond-Yourself/dp/1572245379

• Will & Harper on Netflix: https://www.netflix.com/title/81760197

• Slow Horses on AppleTV+: https://tv.apple.com/us/show/slow-horses/umc.cmc.2szz3fdt71tl1ulnbp8utgq5o

• Aura frames: https://auraframes.com/

• Augie studio: https://augie.studio/

• Harrah’s Entertainment: https://en.wikipedia.org/wiki/Harrah%27s_Entertainment

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

—

Lenny may be an investor in the companies discussed.

Michael Margolis has been a UX research partner at Google Ventures (GV) for nearly 15 years. He has developed a unique approach to helping startups identify their “bullseye customer”—the specific subset of their target market who initially is most likely to adopt their product. Michael has conducted over 300 hands-on research sprints with GV portfolio companies across various industries and helped develop the “design sprint” process made famous by the book Sprint. In our conversation, we discuss:

• The step-by-step process of running a bullseye customer sprint

• The most common mistakes founders make when picking their first customers

• Practical tips for conducting effective customer interviews

• How to create simple but effective prototypes for user research

• The power of “watch parties” in aligning teams around customer insights

• How to apply these methods beyond typical tech startups

—

Brought to you by:

• Eppo—Run reliable, impactful experiments

• Paragon—Ship every SaaS integration your customers want

• Enterpret—Transform customer feedback into product growth

—

Find the transcript at: https://www.lennysnewsletter.com/p/finding-your-bullseye-customer-michael-margolis

—

Where to find Michael Margolis:

• X: https://x.com/mmargolis

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

• Website: https://www.learnmorefaster.com/

• Medium: https://medium.com/@mmargolis

—

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) Michael’s background

(09:11) Bullseye customers vs. ideal customer profiles (ICPs)

(12:32) An overview of the bullseye customer sprint

(20:56) When to use the bullseye customer sprint

(22:19) Step one: Agree on goals and key questions

(23:48) Step two: Define your bullseye customer

(25:52) The importance of a narrow target audience

(29:00) An example of step two in action

(38:24) Narrowing attributes and exclusion criteria

(43:28) Step three: Recruiting and compensating participants

(56:11) Step four: Creating effective prototypes

(01:01:10) Step five: Drafting your interview guide

(01:08:49) Step six: The watch party method

(01:19:40) Common pitfalls and final thoughts

(01:24:43) Closing thoughts and where to find Michael

—

Referenced:

• Learn More Faster: How to Find Your Bullseye Customer and Their Perfect Product: https://www.learnmorefaster.com

• Alcoa: https://www.alcoa.com

• Dupont: https://www.dupont.com

• Ericsson: https://www.ericsson.com

• Google Ventures: https://www.gv.com/

• Kate Aronowitz on LinkedIn: https://www.linkedin.com/in/katearonowitz/

• Vanessa Cho on LinkedIn: https://www.linkedin.com/in/veecho/

• How to kickstart and scale a consumer business—Step 2: Identify your super-specific who: https://www.lennysnewsletter.com/p/consumer-business-super-specific-who

• When enough is enough | Andy Johns (ex-FB, Twitter, Quora): https://www.lennysnewsletter.com/p/when-enough-is-enough-andy-johns

• Zipline for health care: https://www.flyzipline.com/solutions/healthcare

• Jobs to Be Done framework: https://www.christenseninstitute.org/theory/jobs-to-be-done

• User Interviews: https://www.userinterviews.com/

• Respondent: https://www.respondent.io/

• Flatiron Health: https://flatiron.com/

• How to identify your ideal customer profile (ICP): https://www.lennysnewsletter.com/p/how-to-identify-your-ideal-customer

• Gong: https://www.gong.io

• Linear: https://linear.app

• Gusto: https://gusto.com/

• Humble Inquiry: The Gentle Art of Asking Instead of Telling: https://bookshop.org/p/books/humble-inquiry-second-edition-the-gentle-art-of-asking-instead-of-telling-edgar-h-schein/14739375

• Figma: https://www.figma.com

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

—

Lenny may be an investor in the companies discussed.

Jen Abel is the co-founder of JJELLYFISH, where she and her team have worked with over 300 early-stage founders to learn how to sell, do early customer discovery, and set up a repeatable sales motion on the way to their first $1M ARR. In our conversation, Jen shares:

• Why founder-led sales is so crucial early on

• The sales process, step by step

• How to craft effective outreach messages

• Where to find leads

• What three channels work best for outreach

• What to say on your first call

• How to maintain momentum

• Strategies for navigating procurement and closing deals

• Common pitfalls in the sales process and how to avoid them

—

Brought to you by:

• Brave Search—A smarter way to search

• Vanta—Automate compliance. Simplify security

• Paragon—Ship every SaaS integration your customers want

—

Find the transcript at: https://www.lennysnewsletter.com/p/master-founder-led-sales-jen-abel

—

Where to find Jen Abel:

• X: https://x.com/jjen_abel

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

—

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) Jen’s background

(02:20) The importance of founder-led sales

(08:24) The steps of a sales cycle

(12:01) Tactics for effective cold outreach

(16:47) Conversion rate vs. win rate

(20:20) The time it takes to find product-market fit

(23:06) Identifying and engaging prospects

(30:58) Nailing the first phone call

(34:14) Buying vs. selling

(38:08) Testing the questions to ask

(41:57) Avoiding common sales questions and securing the second call

(43:08) Co-authoring with customers

(45:06) Time-boxing service contracts

(49:20) Why you should avoid demos on the first call

(51:05) Dealing with procurement

(54:22) The power of enterprise sales

(58:14) Getting a signature

(01:00:15) Choosing a focus and overcoming sales challenges

(01:02:19) General timelines

(01:04:27) Final thoughts and advice

(01:13:32) Working with Jen

—

Referenced:

• Wiz: https://www.wiz.io/

• JJELLYFISH: https://www.jjellyfish.com/

• Clay: https://www.clay.com/

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

• Airtable: https://www.airtable.com/

• Figma: https://www.figma.com/

• GitHub: https://github.com/

• Vanta: https://www.vanta.com/

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

• Glengarry Glen Ross: https://www.imdb.com/title/tt0104348/

• A step-by-step guide to crafting a sales pitch that wins | April Dunford (author of Obviously Awesome and Sales Pitch): https://www.lennysnewsletter.com/p/a-step-by-step-guide-to-crafting

• Sales Pitch: How to Craft a Story to Stand Out and Win: https://www.amazon.com/Sales-Pitch-Craft-Story-Stand-ebook/dp/B0CHY6BNDN

• Sprig: https://sprig.com/

• Zip: https://zip.co/

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

—

Lenny may be an investor in the companies discussed.

Amjad Masad is the co-founder and CEO of Replit, a browser-based coding environment that allows anyone to write and deploy code. Replit has 34 million users globally and is one of the fastest-growing developer communities in the world. Prior to Replit, Amjad worked at Facebook, where he led the JavaScript infrastructure team and contributed to popular open-source developer tools. Additionally, he played a key role as a founding engineer at the online coding school Codecademy. In our conversation, Amjad shares:

• A live demo of Replit in action

• How Replit’s AI agent can build full-stack web applications from a simple text prompt

• The implications of AI-powered development for product managers, designers, and engineers

• How this might reshape companies and careers

• Why being “generative” will become an increasingly valuable skill

• “Amjad’s law” and how learning to debug AI-generated code is becoming ever more valuable

• Much more

—

Brought to you by:

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

• Persona—A global leader in digital identity verification

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

—

Find the transcript at: https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad

—

Where to find Amjad Masad:

• X: https://x.com/amasad

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

• Website: https://amasad.me/

—

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) Introduction to Amjad Masad and Replit

(02:41) The vision and challenges of Replit

(06:50) Replit’s growth and user stories

(10:49) Demo of Replit’s capabilities

(16:51) Building and iterating with Replit

(25:04) Real-world applications and use cases

(30:13) The technology stack

(33:48) The evolution of Replit and its capabilities

(39:36) The future of AI in software development

(44:04) Skills for the future: generative thinking and coding

(47:26) Amjad’s law

(50:36) Replit’s new developments and future plans

—

Referenced:

• Replit: https://replit.com/

• Cursor: https://www.cursor.com

• Aman Mathur on LinkedIn: https://www.linkedin.com/in/aman-mathur/

• Node: https://nodejs.org/en

• Claude: https://claude.ai/

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

• Wasm: https://webassembly.org/

• Figma: https://www.figma.com/

• Codecademy: https://www.codecademy.com/

• Hacker News: https://news.ycombinator.com/news

• Paul Graham’s website: https://www.paulgraham.com/

• Jevons paradox: https://en.wikipedia.org/wiki/Jevons_paradox

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

• Open AI: https://openai.com/

• Amjad’s tweet about “society of models”: https://x.com/amasad/status/1568941103709290496

• About HCI: https://www.designdisciplin.com/p/hci-profession

• Taylor Swift’s website: https://www.taylorswift.com/

• Andrew Wilkinson on LinkedIn: https://www.linkedin.com/in/awilkinson/

• Haya Odeh on LinkedIn: https://www.linkedin.com/in/haya-odeh-b0725928/

• Amjad’s law: https://x.com/snowmaker/status/1847377464705896544

• Ray Kurzweil’s website: https://www.thekurzweillibrary.com/

• God of the gaps: https://en.wikipedia.org/wiki/God_of_the_gaps

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

—

Lenny may be an investor in the companies discussed.

Raaz Herzberg is the chief marketing officer and VP of product strategy at Wiz. Wiz hit $100 million ARR within 18 months (the fastest growth in startup history) and, five years in, is generating over $500 million ARR. It also serves over 45% of the Fortune 100. Raaz was one of the first five employees at Wiz, joining as the first product manager, and helped the team pivot to what may be the most intense PMF in history. Before Wiz, Raaz led security products at Microsoft, including Azure Sentinel. In our conversation, we discuss:

• How Wiz pivoted from their initial idea and found deep product-market fit

• What Raaz learned about listening to customers

• Why she moved from product to marketing, despite no prior experience

• How she thinks differently as a marketer with a product background

• Lessons learned from scaling a hypergrowth startup like Wiz

• Much more

—

Brought to you by:

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

• Rippling—Automate HR, IT, and finance so you can scale faster

• Cloudinary—The foundational technology for all images and video on the internet

—

Find the transcript at: https://www.lennysnewsletter.com/p/building-wiz-raaz-herzberg

—

Where to find Raaz Herzberg:

• X: https://x.com/raazherzberg

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

—

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) Raaz’s background

(02:54) Early challenges and Wiz’s essential pivot

(06:41) Finding product-market fit

(11:31) Lessons from early customer interactions

(14:54) The power in speaking up when you don’t understand something

(17:46) How Wiz pivoted from their initial idea

(23:52) Marketing and leadership insights

(34:12) The challenges of being a marketing leader

(28:05) Following the “heat” in your organization

(30:22) How Raaz found success as CMO

(34:01) Common CMO mistakes

(36:23) Creating noise and standing out

(40:28) Embracing failure and taking risks

(44:53) The importance of clear communication

(48:32) The “dummy” explanation

(51:00) Building trust and company culture

(53:45) Contrarian corner

(56:34) Lightning round

—

Referenced:

• Wiz: https://www.wiz.io/

• An inside look at Deel’s unprecedented growth | Meltem Kuran Berkowitz (Head of Growth): https://www.lennysnewsletter.com/p/an-inside-look-at-deels-unprecedented

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

• Assaf Rappaport on LinkedIn: https://www.linkedin.com/in/assafrappaport/

• How LinkedIn became interesting: The inside story | Tomer Cohen (CPO at LinkedIn): https://www.lennysnewsletter.com/p/how-linkedin-became-interesting-tomer-cohen

• Shardul Shah on LinkedIn: https://www.linkedin.com/in/shardul-shah-3589062/

• Doug Leone on LinkedIn: https://www.linkedin.com/in/douglas-leone-a2714/

• Jeff Horing on LinkedIn: https://www.linkedin.com/in/jeffhoring2009/

• RSA Conference: https://www.rsaconference.com/

• Microsoft acquires Adallom to advance identity and security in the cloud: https://blogs.microsoft.com/blog/2015/09/08/microsoft-acquires-adallom-to-advance-identity-and-security-in-the-cloud/

• Imposter syndrome: https://www.psychologytoday.com/us/basics/imposter-syndrome

• Careers at Wiz: https://www.wiz.io/careers

• Setting the Table: The Transforming Power of Hospitality in Business: https://www.amazon.com/Setting-Table-Transforming-Hospitality-Business/dp/0060742763

• No Rules Rules: Netflix and the Culture of Reinvention: https://www.amazon.com/No-Rules-Netflix-Culture-Reinvention/dp/1984877860/

• Gong: https://www.gong.io/

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

• Raaz’s pen holder recommendation: https://www.paper-republic.com/products/le-loop-penholder

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

—

Lenny may be an investor in the companies discussed.

Aman Khan is Director of Product at Arize AI, an observability company for AI engineers at companies like Uber, Instacart, and Discord. Previously he was an AI Product Manager at Spotify on the ML Platform team, enabling hundreds of engineers to build and ship products across the company. He has also led and worked on products at Cruise, Zipline, and Apple. In our conversation, we discuss:

• What is an “AI product manager”?

• How to break into AI PM

• What separates top 5% AI PMs

• How to thrive as an individual-contributor PM

• Common pitfalls to avoid when building AI products

• The importance of energy and curiosity in product roles

• Much more

—

Brought to you by:

• Pendo—The only all-in-one product experience platform for any type of application

• Vanta—Automate compliance. Simplify security

• Paragon—Ship every SaaS integration your customers want

—

Find the transcript at: https://www.lennysnewsletter.com/p/becoming-an-ai-pm-aman-khan

—

Where to find Aman Khan:

• X: https://x.com/_amankhan

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

• Website: https://amanalikhan.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) Aman’s background

(06:16) Understanding AI product management roles

(13:29) Getting started as an AI product manager

(18:14) Building a portfolio and standing out

(22:31) Why product management is not dead

(28:56) How to thrive as an AI product manager

(35:42) Finding good ideas that are AI-oriented

(39:27) Be careful not to automate away every customer experience

(42:53) What separates top 5% AI PMs

(46:55) Key habits for long-term IC success

(52:48) The importance of energy in meetings

(57:00) Wandering vs. waiting

(01:01:41) Amplifying signal through AI tools

(01:03:18) Just have fun

(01:05:36) Lightning round

—

Referenced:

• AI Resources and Tools for PMs (Updated Oct 2024): https://open.substack.com/pub/amankhan1/p/ai-resources-and-tools-for-pms-updated

• Unlocking the AI PM Dream: Your Roadmap to Success: https://amankhan1.substack.com/p/unlocking-the-ai-pm-dream-your-roadmap

• Arize: https://arize.com/

• Ryzen: https://www.amd.com/en/products/processors/business-systems/ryzen-ai.html

• NotebookLM: https://notebooklm.google/

• Figma: https://www.figma.com/

• Cursor: https://www.cursor.com/

• Replit: https://replit.com/

• Excalidraw: https://excalidraw.com/

• Vercel: https://vercel.com/

• v0: https://v0.dev/

• 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

• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach

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

• Dall-E: https://openai.com/index/dall-e-3/

• Introducing the Realtime API: https://openai.com/index/introducing-the-realtime-api/

• Intro to Large Language Models | Andrej Karpathy: https://www.youtube.com/watch?v=zjkBMFhNj_g

• Watch Me Build an App in 60 Minutes With o1 and Cursor: https://www.youtube.com/watch?v=9Zmhe6_T-xU

• Greg Isenberg on LinkedIn: https://www.linkedin.com/in/gisenberg/

• Vision, conviction, and hype: How to build 0 to 1 inside a company | Mihika Kapoor (Product at Figma): https://www.lennysnewsletter.com/p/vision-conviction-hype-mihika-kapoor

• Spotify: https://open.spotify.com/

• Instacart: https://www.instacart.com/

• How to grow a subscription business | Yuriy Timen (Grammarly, Canva, Airtable): https://www.lennysnewsletter.com/p/transform-your-subscription-growth

• When Identifying the Problem Isn’t Enough: Lessons from Boxed Cake Mix by Ann M. Aly, TechFlow Director of Human Centered Design: https://www.techflow.com/when-identifying-the-problem-isnt-enough-lessons-from-boxed-cake-mix/

• Waymo: https://waymo.com/

• The Ikea effect: https://thedecisionlab.com/biases/ikea-effect

• Blue Apron: https://www.blueapron.com/

• Unorthodox PM wisdom: Automating user insights, unselling job candidates, logging every decision, more | Kevin Yien (Stripe, Square, Mutiny): https://www.lennysnewsletter.com/p/unorthodox-pm-wisdom-kevin-yien

• LeBron James: https://en.wikipedia.org/wiki/LeBron_James

• The Secrets Behind Lyft’s Dynamic Culture: https://www.forbes.com/sites/marissaperetz/2018/05/16/the-secrets-behind-lyfts-dynamic-culture/

• Aparna Dhinakaran on LinkedIn: https://www.linkedin.com/in/aparnadhinakaran/

• Why most public speaking advice is wrong—and how to finally overcome your speaking anxiety | Tristan de Montebello (CEO & co-founder of Ultraspeaking): https://www.lennysnewsletter.com/p/master-public-speaking-tristan-de-montebello

• Ultraspeaking: https://ultraspeaking.com/lenny/

• A Short History of Nearly Everything: https://www.amazon.com/Short-History-Nearly-Everything/dp/076790818X

• Designing Your Life: How to Build a Well-Lived, Joyful Life: https://www.amazon.com/Designing-Your-Life-Well-Lived-Joyful/dp/1101875321

• Tour de France: Unchained on Netflix: https://www.netflix.com/title/81153133

• Formula 1: Drive to Survive on Netflix: https://www.netflix.com/title/80204890

• Websim: https://websim.ai/

• Appeel Books: https://appeel.brandeditems.com/

• Steve Jobs quote: https://www.goodreads.com/quotes/374630-your-time-is-limited-so-don-t-waste-it-living-someone#

• Becoming a conscious leader: Leading without fear, finding your life’s objective function, and getting better at vision and strategy | John Mark Nickels (Uber, Waymo, DoorDash): https://www.lennysnewsletter.com/p/becoming-a-conscious-leader-john-mark-nickels

• Aman Khan (cricket player): https://en.wikipedia.org/wiki/Aman_Hakim_Khan

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

—

Lenny may be an investor in the companies discussed.

Melissa Perri is the founder of Product Institute, author of Escaping the Build Trap, and host of the Product Thinking Podcast. She has worked with startups, Fortune 50 companies, and everything in between to help them build better products and level up their product teams. In our conversation, we discuss:

• The history of the product owner role

• The differences between product owners and product managers

• How to transition from product owner to product manager

• The evolution of and problems with the SAFe framework

• How large non-tech companies can improve their product practices

• Much more

—

Brought to you by:

• Pendo—The only all-in-one product experience platform for any type of application

• OneSchema—Import CSV data 10x faster

• Coda—The all-in-one collaborative workspace

—

Find the transcript at: https://www.lennysnewsletter.com/p/product-owners-melissa-perri

—

Where to find Melissa Perri:

• X: https://twitter.com/lissijean

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

• Website: https://melissaperri.com/

• Product Institute: https://productinstitute.com/

• Podcast: https://www.produxlabs.com/product-thinking

—

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) Melissa’s background

(02:12) The rise of the product owner role

(06:37) Understanding Agile and Scrum

(08:27) Challenges in Agile transformations

(10:41) The history of the product owner role

(13:58) The Scrum Guide

(15:43) Product owner responsibilities

(21:01) Adopting Scrum in organizations

(26:21) The origins and implementation of SAFe

(35:20) Why Melissa doesn’t recommend SAFe

(40:33) Advice for implementing a digital transformation

(49:12) An example of SAFe adoption

(51:27) The value of experienced product leaders

(56:53) Career paths for product owners

(01:04:14) Transitioning from product owner to product manager

(01:06:41) Be careful relying on certifications

(01:11:43) Evaluating existing product owners

(01:16:55) Final thoughts on Agile and product management

—

Referenced:

• Escaping the Build Trap: How Effective Product Management Creates Real Value: https://www.amazon.com/Escaping-Build-Trap-Effective-Management/dp/149197379X

• Lean UX: https://leanuxnyc.co/

• Scrum: https://www.scrum.org/

• What is Extreme Programming? https://www.agilealliance.org/glossary/xp/

• Capital One: https://www.capitalone.com/

• The Agile Manifesto: https://www.atlassian.com/agile/manifesto

• Ken Schwaber on X: https://x.com/kschwaber

• Jeff Sutherland on X: https://x.com/jeffsutherland

• Kanban: https://www.atlassian.com/agile/kanban

• What is a kanban board?: https://www.atlassian.com/agile/kanban/boards

• Ron Jeffries’s website: https://www.ronjeffries.com/

• Jeff Patton on X: https://x.com/jeffpatton

• The Scrum Guide: https://www.scrum.org/resources/scrum-guide

• OpenSky: https://www.openskycc.com/

• SAFe: https://scaledagileframework.com/

• Dean Leffingwell on LinkedIn: https://www.linkedin.com/in/deanleffingwell/

• Capital One scraps 1,100 tech positions: https://www.reuters.com/technology/capital-one-scraps-1100-tech-positions-source-2023-01-19/

• Product management theater | Marty Cagan (Silicon Valley Product Group): https://www.lennysnewsletter.com/p/product-management-theater-marty

• Marty Cagan on LinkedIn: https://www.linkedin.com/in/cagan/

• Jeff Gothelf on X: https://x.com/jboogie

• Shruti Patel on LinkedIn: https://www.linkedin.com/in/shruti-patel-32bb573a/

• Product Thinking Podcast: Mastering Product Focus: Balancing Legacy and Innovation with Shruti Patel: https://www.produxlabs.com/product-thinking-blog/2024/9/25/episode-190-mastering-product-focus-balancing-legacy-and-innovation-with-shruti-patel

• Melissa Douros on LinkedIn: https://www.linkedin.com/in/melissadouros/

• Mind the Product: https://www.mindtheproduct.com/

• Athenahealth: https://www.athenahealth.com/

• McKinsey: https://www.mckinsey.com/

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

—

Lenny may be an investor in the companies discussed.

Archie Abrams is the VP of Product and Head of Growth at Shopify, where he leads a 600+ person growth org across product, design, engineering, data, ops, and growth marketing. Shopify powers over 10% of e-commerce in the United States, with $235 billion in GMV in 2023 (roughly the size of Finland’s economy). He previously led Consumer product and growth at Lyft and was at Udemy for 8 years as SVP of Product having joined the company when it was 10 people. In our conversation, we discuss:

• Why Shopify optimizes for churn

• Why the core product team doesn’t use metrics-based goals

• Why they keep multi-year experiment holdouts

• How they structure their growth team

• The benefits of not having a CMO

• Lessons learned about integrating sales into a product-led growth model

• The power of discounting as a growth lever

• Much more

—

Brought to you by:

• Explo—Embed customer-facing analytics in your product

• Dovetail—The customer insights hub for product teams

—

Find the transcript at: https://www.lennysnewsletter.com/p/shopifys-growth-archie-abrams

—

Where to find Archie Abrams:

• X: https://x.com/archieabrams

• LinkedIn: https://www.linkedin.com/in/archie-abrams-b6aa8b6/

—

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) Archie’s background 

(02:30) Shopify’s impressive growth

(06:17) Shopify’s unique approach to churn and retention

(08:43) Monetization model and success metrics

(11:08) Long-term experimentation and metrics

(23:00) Examples of big wins that Archie’s team has shipped

(26:42) Monetary friction

(27:14) Metrics

(29:47) Shopify’s growth team structure

(33:03) Goal setting and forecasting

(37:10) Examples of long-term results within Shopify

(41:36) Shipping neutral experiments

(42:05) Building a hundred-year company

(48:04) Why Shopify doesn’t use KPIs

(51:30) Shopify’s “Get s**t done” framework

(54:30) Cross-team collaboration 

(58:48) The importance of an opinionated founder 

(01:01:12) Growth and sales integration

(01:06:42) Shopify’s marketing structure

(01:08:49) Insights on discounting from Udemy

(01:11:09) Lightning round

—

Referenced:

• Shopify: https://www.shopify.com/

• Tobias Lütke on LinkedIn: https://www.linkedin.com/in/tobiaslutke

• Gross Merchandise Value: Calculation and Best Practices: https://www.shopify.com/retail/gross-merchandise-value

• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach

• Glen Coates on LinkedIn: https://www.linkedin.com/in/glcoates

• Harley Finkelstein on LinkedIn: https://www.linkedin.com/in/harleyf

• Udemy: https://www.udemy.com/

• Scientific Advertising: https://www.amazon.com/Scientific-Advertising-Original-Claude-Hopkins/dp/1640954252

• Four-Minute Mile: https://www.amazon.com/Four-Minute-Mile-Roger-Bannister/dp/1493038753/

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

• Suno: https://suno.com/

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

—

Lenny may be an investor in the companies discussed.

Alistair Croll is the co-author of the best-selling book Lean Analytics and a longtime product manager, entrepreneur, and startup advisor. He was also instrumental in my starting a company, funding it, and helping us exit to Airbnb as part of his Year One Labs incubator. He’s chaired notable events such as O’Reilly’s Strata and UBM’s Cloud Connect and founded FWD50. In our conversation, we focus on lessons from an upcoming book by Alistair and his co-author, Emily Ross, Just Evil Enough, which is set for release in late 2024. We cover:

• The importance of subversive marketing strategies in most startups’ growth

• 11 specific subversive tactics that successful companies have used

• Examples of companies like Netflix, Airbnb, and Tesla that used clever tactics early on

• A framework for scanning your market for opportunities

• The importance of finding your “zero-day marketing exploit”

• How to apply these tactics ethically without actually being evil

• Much more

—

Brought to you by:

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

• Hex—Helping teams ask and answer data questions by working together

• Vanta—Automate compliance. Simplify security

—

Find the transcript and show notes at: https://www.lennysnewsletter.com/p/just-evil-enough-alistair-croll

—

Where to find Alistair Croll:

• X: https://x.com/acroll

• Threads: https://www.threads.net/@alistairish

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

• Website: https://justevilenough.com/

• Substack: https://acroll.substack.com/

• Just Evil Enough on X: https://x.com/evilenough

• Just Evil Enough on LinkedIn: https://www.linkedin.com/company/just-evil-enough/

—

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) Alistair’s background 

(02:00) The story behind Alistair and Emily’s book Just Evil Enough

(06:17) Examples of subversive tactics

(07:43) The importance of unfair advantage

(10:36) The origin of the title “Just Evil Enough”

(14:24) System awareness and novelty

(19:16) How to use this thinking successfully 

(22:37) Normalizing disagreeable thinking 

(25:49) Recon canvas and market scanning

(32:43) 11 tactics for subversive marketing

(57:01) Implementing subversive strategies

(01:05:01) Ethical considerations in marketing

(01:08:19) Lightning round

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

—

Lenny may be an investor in the companies discussed.

Shreyas Doshi is a former product leader at Stripe, Twitter, Google, and Yahoo. He’s now a full-time advisor and coach to founders and executives. Shreyas is known for his incredibly insightful writing on products, which has garnered him a passionate following in the PM and startup community. Last week, we sat down together at the very first Lenny and Friends Summit in San Francisco for a special live episode. We covered:

• Why product leaders often feel overwhelmed with work, and how to combat it

• The importance of developing good taste, and how to do it

• How to reduce frustration in your product leadership role

• The critical skill of truly listening as a leader

• Common pitfalls in annual planning and decision-making

• Lots of laughs

—

To learn more from Shreyas, check out these courses:

• Improving Your Product Sense: https://bit.ly/product-sense

• Managing Your PM Career: https://bit.ly/pm-career-course

—

Brought to you by:

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

• Paragon—Ship every SaaS integration your customers want

• Vanta—Automate compliance. Simplify security

—

Find the transcript at: https://www.lennysnewsletter.com/p/shreyas-doshi-live

—

Where to find Shreyas Doshi:

• X: https://x.com/shreyas

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

• Threads: https://www.threads.net/@shreyas.threads

• Linktree: https://linktr.ee/shreyasdoshi

• YouTube: https://www.youtube.com/@ShreyasDoshiVideos

—

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) Introduction

(05:35) Question one: Why am I so busy?

(10:08) Annual planning as an example

(16:48) Tactical tips for staying less busy

(25:20) Question two: Do I actually have good taste?

(38:09) Question three: Why does my job feel so frustrating?

(43:29) Question four: Am I really listening?

(44:35) Closing remarks

—

Referenced:

• Shreyas Doshi on pre-mortems, the LNO framework, the three levels of product work, why most execution problems are strategy problems, and ROI vs. opportunity cost thinking: https://www.lennysnewsletter.com/p/episode-3-shreyas-doshi

• LNO framework: https://twitter.com/shreyas/status/1492345184171945984

• Time management techniques that actually work: https://www.lennysnewsletter.com/p/time-management-techniques-that-actually

• Part 2: Time management techniques that actually work: https://www.lennysnewsletter.com/p/part-2-time-management-techniques

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

• Stripe Connect: https://stripe.com/connect

• Jeff Bezos explains one-way door decisions and two-way door decisions: https://www.youtube.com/watch?v=rxsdOQa_QkM

• Spotify Is America’s Most Loved Workplace: https://www.newsweek.com/2021/10/29/spotify-americas-most-loved-workplace-1639982.html

• Shreyas on “thinking is cheap”: https://www.linkedin.com/posts/shreyasdoshi_thinking-is-very-cheap-doing-is-very-expensive-activity-7225237421813116929-Qzi3/

• Good Product Strategy, Bad Product Strategy from Shreyas: https://x.com/shreyas/status/1244810075908128768

• Shreyas on annual planning and metrics:

https://x.com/shreyas/status/1302423854095036421

https://x.com/shreyas/status/1304628719374544896

• Jensen Huang on LinkedIn: https://www.linkedin.com/in/jenhsunhuang/

• Patrick Mahomes’s website: https://www.adidas.com/us/patrick_mahomes

• Virat Kohli: https://en.wikipedia.org/wiki/Virat_Kohli

• Reversible and Irreversible Decisions: https://fs.blog/reversible-irreversible-decisions/

• Fail fast: https://en.wikipedia.org/wiki/Fail_fast

• 3 levels of product work: https://twitter.com/shreyas/status/1370248637842812936

• Shakespeare quote: https://nosweatshakespeare.com/quotes/famous/to-thine-own-self-be-true/

• Rick Rubin: Legendary Music Producer | Lex Fridman Podcast #275: https://Dwww.youtube.com/watch?v=H_szemxPcTI

• Blake Burge on Rick Ruben: https://x.com/blakeaburge/status/1794470295828341222

• Rick Rubin on X: https://x.com/RickRubin

• Dee Hock on X: https://x.com/deewhock

• Dee Hock quote on listening: https://x.com/shreyas/status/1351279398423465984

• Peter Drucker: https://en.wikipedia.org/wiki/Peter_Drucker

• Peter Drucker quotes on listening: https://www.azquotes.com/author/4147-Peter_Drucker/tag/listening

• Lenny’s first podcast recording: https://www.youtube.com/watch?v=YP_QghPLG-8

• A Recipe to Become a Great Listener: https://www.youtube.com/watch?v=gUQJkiDy2Ko

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

—

Lenny may be an investor in the companies discussed.

Naomi Gleit is head of product at Meta, joined as employee #29, and is the longest-serving executive at Meta other than Mark Zuckerberg. She’s been at the center of some of the company’s most foundational products, including Facebook’s early growth team. In our conversation, we discuss:

• How she originally landed at Facebook

• The evolution of Facebook’s growth team and key metrics

• Lessons from working with Mark Zuckerberg

• Insights from Facebook’s activation metric and retention strategies

• Leadership lessons and “Naomiisms” for effective product management

• Tactics for creating extreme clarity in team communication

• Advice for running effective meetings

• More

—

Brought to you by:

• Pendo—The only all-in-one product experience platform for any type of application

• Vanta—Automate compliance. Simplify security

• Eppo—Run reliable, impactful experiments

—

Find the transcript and show notes at: https://www.lennysnewsletter.com/p/metas-head-of-product-naomi-gleit

—

Where to find Naomi Gleit:

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

• LinkedIn: https://www.linkedin.com/in/naomi-gleit/

• Website: https://naomi.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) Introduction to Naomi Gleit

(01:53) Naomi’s journey at Meta

(06:18) Landing a job at Facebook

(10:40) Becoming a product manager

(13:40) Working as Head of Product at Meta

(14:55) Insights on working with Mark Zuckerberg

(20:04) Small Groups and “disagreeable givers”

(24:28) The legendary growth team

(33:45) Activation metrics and onboarding

(43:44) Naomi’s leadership and PM philosophy

(53:00) Canonical documents

(55:55) Simplifying complex projects

(01:00:33) Teen accounts: a case study

(01:06:37) Running effective meetings

(01:12:10) The importance of exercise

(01:16:36) The role of a product manager

(01:25:49) Lightning round

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

—

Lenny may be an investor in the companies discussed.

Jessica Hische is a lettering artist and New York Times bestselling author based in Oakland, California. She specializes in typographical work for logos, film, books, and other commercial applications. Her clients include Wes Anderson, The United States Postal Service, Target, Hallmark, and Penguin Books, and her work has been featured in design and illustration annuals both in the U.S. and internationally. She’s been named a Print Magazine New Visual Artist (20 under 30), one of Forbes 30 under 30 in Art and Design, an ADC Young Gun, a “Person to Watch” by GD USA, and an Adweek “Creative 100.” In our conversation, we discuss:

• My new logo and brand!

• Jessica’s process for refreshing my logo/brand

• Why most startups shouldn’t worry about their logo/brand

• The psychology behind different typography choices

• Balancing creativity with business needs in logo design

• Jessica’s unique approach to pricing logo work

• How AI is (and isn’t) impacting the design world

• Jessica’s other creative pursuits, including children’s books and art supply stores

—

Brought to you by:

• The Enterprise Ready Conference — For B2B leaders building enterprise SaaS

• OneSchema — Import CSV data 10x faster

• Merge — A single API to add hundreds of integrations into your app

—

Find the transcript at: https://www.lennysnewsletter.com/p/seeing-like-a-designer-jessica-hische

—

Where to find Jessica Hische:

• Threads: https://www.threads.net/@jessicahische

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

• Website: https://jessicahische.is

—

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) Jessica’s background

(01:32) The logo refresh process

(09:45) When to refresh your logo

(11:45) High-level overview

(18:04) Approaching Lenny’s brand refresh

(24:25) How to see like a designer

(37:53) Lenny’s new logo: where we landed

(44:07) Brand’s role in company success

(50:04) Jessica’s flexible pricing strategies and collaborative design process

(57:14) Balancing multiple creative projects

(01:01:48) Using AI in creative work

(01:05:50) Upcoming projects and final thoughts

(01:08:24) Lightning round

—

Referenced:

• Jeni’s: https://jenis.com

• James Edmondson on LinkedIn: https://www.linkedin.com/in/jamestedmondson/

• Figma Config: https://config.figma.com/

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

• MyFonts: https://www.myfonts.com/

• Geometric sans serif fonts: https://www.myfonts.com/pages/tags/geometric%20sans%20serif-fonts

• The Rise of Fractional Executives: https://www.reforge.com/blog/leveraging-fractional-executives

• JH&F: https://jessicahische.shop/pages/my-oakland-store

• Drawling: https://drawling.shop/

• Jessica Hische’s books on Amazon: https://www.amazon.com/stores/Jessica-Hische/author/B082XDN54V

• Dreamforce: https://www.salesforce.com/dreamforce

• Bezier handles: https://www.tella.tv/definition/bezier-handles

• My First Book of Fancy Letters: https://www.amazon.com/My-First-Book-Fancy-Letters/dp/0593385012/r

• The Creative Act: A Way of Being: https://www.amazon.com/Creative-Act-Way-Being/dp/0593652886/

• Inside Paragraphs: Typographic Fundamentals: https://www.amazon.com/Inside-Paragraphs-Fundamentals-Cyrus-Highsmith/dp/1616899417

• Just Kids: https://www.amazon.com/Just-Kids-Patti-Smith/dp/0060936223

• Robert Mapplethorpe: https://en.wikipedia.org/wiki/Robert_Mapplethorpe

• The Emperor of All Maladies: A Biography of Cancer: https://www.amazon.com/Emperor-All-Maladies-Biography-Cancer/dp/1439170916/r

• Severance on Prime Video: https://www.amazon.com/Severance-Toby-Stephens/dp/B001ARYGCU

• Penco brown bag stand: https://penco.jp/en/products/db079/

• XOXO: https://xoxofest.com/

• Mariame Kaba quotes: https://www.goodreads.com/author/quotes/8156101.Mariame_Kaba

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

—

Lenny may be an investor in the companies discussed.

Anneka Gupta is the Chief Product Officer at Rubrik, a leading B2B cybersecurity company. She previously spent 11 years at LiveRamp, where she was the President and Head of Product and Platforms leading product development and go-to-market operations and strategy. Anneka also sits on the board of directors for Tinuiti and teaches product management at Stanford University. In our conversation, we discuss:

• Navigating “founder mode” dynamics in organizations

• Navigating difficult personalities and aligning teams

• The PM skill of summarization

• Giving and receiving hard feedback effectively

• The value of a positive mindset

• Tips for breaking into product management

• Much more

—

Brought to you by:

• The Enterprise Ready Conference — For B2B leaders building enterprise SaaS

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

• Eppo — Run reliable, impactful experiments

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Find the transcript at: https://www.lennysnewsletter.com/p/becoming-more-strategic-anneka-gupta

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Where to find Anneka Gupta:

• X: https://x.com/annekagupta

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

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Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

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

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In this episode, we cover:

(00:00) Introduction to Anneka Gupta

(01:43) Key mindsets for success

(05:30) Managing energy for optimal performance

(09:05) Founder mode

(18:26) Becoming more strategic

(27:54) The importance of decision-making

(37:18) Navigating difficult personalities

(41:38) Techniques for giving and receiving feedback

(51:01) Transitioning into product management

(54:56) Advice for aspiring product managers

(59:39) Leveraging AI tools in product management

(01:01:27) The power of a positive mindset

(01:04:30) Lightning round

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Referenced:

• Founder Mode: https://paulgraham.com/foundermode.html

• Building a long and meaningful career | Nikhyl Singhal (Meta, Google): https://www.lennysnewsletter.com/p/building-a-long-and-meaningful-career

• The Skip community: https://www.linkedin.com/company/skip-community/

• Rubrik: https://www.rubrik.com/

• 5 essential questions to craft a winning strategy | Roger Martin (author, advisor, speaker): https://www.lennysnewsletter.com/p/the-ultimate-guide-to-strategy-roger-martin

• Playing to Win: How Strategy Really Works: https://www.amazon.com/Playing-Win-Strategy-Really-Works/dp/142218739X

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

• Acquired podcast interviews Zuckerberg in San Francisco: https://transistor.fm/acquired-live/

• Hema Mohan on LinkedIn: https://www.linkedin.com/in/hemamohan/

• Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity: https://www.amazon.com/Radical-Candor-Kick-Ass-Without-Humanity/dp/1250103509

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

• LiveRamp: https://liveramp.com/

• Product Management class at Stanford: https://www.gsb.stanford.edu/experience/learning/experiential-learning/action-learning-program/product-management

• Figma: https://www.figma.com/

• Dovetail: https://try.dovetail.com/

• The Remarkable Advantage of Abundant Thinking: https://review.firstround.com/the-remarkable-advantage-of-abundant-thinking/

• The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers: https://www.amazon.com/Hard-Thing-About-Things-Building/dp/0062273205

• Brandon Sanderson’s books: https://www.amazon.com/stores/Brandon-Sanderson/author/B001IGFHW6

• Fallout on Prime Video: https://www.amazon.com/dp/B0CN4HV16N

• Thunderbolt 4 ( 3-meter cable): https://www.apple.com/shop/product/MW5H3AM/A/thunderbolt-4-usb%E2%80%91c-pro-cable-3-m

• Isaac Asimov: https://en.wikipedia.org/wiki/Isaac_Asimov

• The complete Foundation series: https://www.amazon.com/Complete-Asimovs-Foundation-Foundations-Prelude/dp/B01EFDEMS8

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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.

Tristan de Montebello is the co-creator of Ultraspeaking, the most effective method I’ve come across for rapidly improving communication and presentation skills. In 2017, Tristan became the fastest person ever to reach the finals of the World Championship of Public Speaking, achieving this feat in just seven months with no prior experience. In our conversation, we discuss:

• Why public speaking is a meta skill that can transform your life

• Practical games and exercises to improve your speaking skills

• The “Accordion Method” for preparing talks without memorization

• The “Bow and Arrow Technique” for crafting memorable presentations

• Tristan’s journey to the World Championship of Public Speaking finals

• Lenny doing some of the exercises live on-screen

Tristan is offering a limited-time discount to Ultraspeaking. Both codes are valid until November 14, 2024:

→ $500 off an Unlimited Membership with code UNLIMITEDLENNY500

→ $200 off a Rapid Tier pass for a single cohort with code RAPIDLENNY200

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Brought to you by:

• Eppo—Run reliable, impactful experiments

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

• Brave Search—A smarter way to search

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Find the transcript at: https://www.lennysnewsletter.com/p/master-public-speaking-tristan-de-montebello

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Where to find Tristan de Montebello:

• X: https://x.com/Montebello

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

• Website: https://ultraspeaking.com

• Free email course: https://ultraspeaking.com/lenny/

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Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

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

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In this episode, we cover:

(00:00) Introduction to Tristan de Montebello and Ultraspeaking

(01:42) Personal experiences with public speaking

(05:35) Misconceptions and meta skills in public speaking

(08:56) Enjoyment as a barometer for effective speaking

(15:30) Tactical tips for public speaking

(29:15) The importance of practice and games

(34:50) Game 1: The Conductor (Accessing different emotional states)

(45:54) Mindset shift: playing the game

(51:07) Game 2: Triple Step (Staying focused amid distractions)

(01:07:51) Quieting the noise

(01:09:46) Game 3: Conviction Prompts (Building executive presence)

(01:17:27) The Accordion Method explained

(01:37:57) The Bow and Arrow technique

(01:43:43) Final thoughts and encouragement

(01:44:55) Lightning round

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Referenced:

• Michael Gendler on LinkedIn: https://www.linkedin.com/in/michaelgendler

• Alienor playing Conductor: https://www.youtube.com/watch?v=nmholFWwHro

• Triple Step: https://ultraspeaking.com/triple-step-game/

• Rapid Fire Analogies: https://ultraspeaking.com/rapid-fire-game/

• Joe Rogan Experience #1309 — Naval Ravikant: https://www.youtube.com/watch?v=3qHkcs3kG44

• The Big Leap: Conquer Your Hidden Fear and Take Life to the Next Level: https://www.amazon.com/Big-Leap-Conquer-Hidden-Level/dp/0061735361

• Tall poppy syndrome: https://en.wikipedia.org/wiki/Tall_poppy_syndrome

• Peaky Blinders on Netflix: https://www.netflix.com/title/80002479

• The Nice Guys on Prime Video: https://www.amazon.com/Nice-Guys-Russell-Crowe/dp/B01FV1GLR8

• Ember temperature control smart mug: https://www.amazon.com/Ember-Temperature-Control-1-5-hr-Battery/dp/B07NQRM6ML

• How I got to the World Championships of Public Speaking in 7 months: https://medium.com/the-mission/3000-people-staring-c2cbd14c6d6c

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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.

Raiza Martin is a senior product manager for AI at Google Labs, where she leads the team behind NotebookLM, an AI-powered research tool that includes a delightful podcast-on-demand feature called “Audio Overviews.” NotebookLM started as a 20% project and has grown into a product that’s spreading across social media and has a Discord server with over 60,000 users. Raiza previously worked on AI Test Kitchen and has a background in startups, payments, and ads. In our conversation, we discuss:

• The origin story of NotebookLM

• The future road map for NotebookLM

• How Google Labs operates differently from the rest of Google

• The development of the “Audio Overviews” feature

• Key metrics and growth of NotebookLM

• Stories about collaborating with author Steven Johnson

• Navigating potential misuse of AI technology

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Brought to you by:

• Explo — Embed customer-facing analytics in your product

• Sprig⁠⁠ — Build products for people, not data points

• Sidebar — Accelerate your career by surrounding yourself with extraordinary peers

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Find the transcript and show notes at: https://www.lennysnewsletter.com/p/googles-notebooklm-raiza-martin

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Where to find Raiza Martin:

• X: https://x.com/raiza_abubakar

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

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Where to find Lenny: