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

—

Brought to you by:

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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/

—

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) 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 [email protected].

—

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

—

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

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• OneSchema—Import CSV data 10x faster

—

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=

—

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 [email protected].

—

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

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

—

Lenny may be an investor in the companies discussed.

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

—

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/

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

—

Lenny may be an investor in the companies discussed.

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

—

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

—

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/

—

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/

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

—

Lenny may be an investor in the companies discussed.

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 [email protected].

—

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

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—

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 [email protected].

—

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 [email protected].

—

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

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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 [email protected].

—

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 [email protected].

—

Lenny may be an investor in the companies discussed.