Lenny’s Podcast: Product | Growth | Career

Alex Komoroske is a strategic leader who merges the practice, theory, and mindset necessary to tackle complex problems. He spent 13 years at Google, where he worked on Search and DoubleClick and led Chrome’s Open Web Platform. He also spearheaded Augmented Reality in Google Maps and developed toolkits to align companywide strategy from the ground up. After serving as Head of Corporate Strategy at Stripe, he is now co-founding a startup aimed at reimagining the web for the AI era. Alex created the popular “Slime Molds” deck, which offers fresh insights into organizational dynamics. He is also the author of the widely read “Bits and Bobs,” a collection of thought-provoking reflections.In our conversation, we delve into:

• “Organizational kayfabe”

• “Gardening” vs. “building”

• How AI will soon change how we build product

• How and why to embrace the adjacent possible

• The power of reflection and how to build it into your workflow

• How to create emergent properties in organizations

• How to run effective “strategy salons” or “nerd clubs”

• Much more

—

Brought to you by:

• Eppo—Run reliable, impactful experiments

• Vanta—Automate compliance. Simplify security

• Coda—The all-in-one collaborative workspace

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Find the transcript and show notes at: https://www.lennysnewsletter.com/p/unconventional-product-advice-alex-komoroske

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Where to find Alex Komoroske:

• X: https://x.com/komorama

• LinkedIn: https://www.linkedin.com/in/alex-komoroske-6597336/

• Website: https://www.komoroske.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) Introduction to Alex

(01:53) Alex’s Bits and Bobs document

(06:20) The Compendium and note-taking process

(10:10) The impact of AI and LLMs on product development

(14:24) Skills to lean into as a product manager

(19:02) How AI makes us better as individuals

(23:04) Organizational kayfabe

(31:48) Gardening vs. building

(34:46) Emergence-oriented thinking

(41:55) Slime molds and organizational structure

(45:15) Identifying resonant ideas

(47:05) The power of metaphors

(48:02) Strategy salons and nerd clubs

(52:30) Building and sustaining communities

(55:59) Productivity hacks and self-control

(01:01:04) Life philosophy and personal insights

(01:07:52) The adjacent possible

(01:15:56) Lightning round

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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.

Benjamin Lauzier has been building and scaling marketplaces for almost 15 years. He was the VP of product and growth at Thumbtack, where he rebuilt the product team and Thumbtack’s growth levers, re-architected their revenue model, and helped double the company’s growth within three years. Prior to Thumbtack, Ben was at Lyft for six years, where he led the supply side of the product organization to a point where 1% of U.S. workers were driving for Lyft every month. Currently, he advises marketplace teams and founders, teaches a Reforge course on marketplace growth, and has recently launched a health tech company called Nurra, which connects users with care advocates to navigate the health-care system. In our conversation, we cover:

• What defines a marketplace business

• Strategies for growing supply and demand in the early stages

• How to measure liquidity and other marketplace health metrics

• How to evaluate if a marketplace model is right for your idea

• Lessons from Lyft, Thumbtack, and other successful marketplaces

• The differences between product management in the U.S. and Europe

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Brought to you by:

• Eppo—Run reliable, impactful experiments

• Paragon—Ship every SaaS integration your customers want

• Vanta—Automate compliance. Simplify security

—

Find the transcript and show notes at: https://www.lennysnewsletter.com/p/how-marketplaces-win-benjamin-lauzier

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Where to find Benjamin Lauzier:

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

• Ben’s Reforge course: https://www.reforge.com/courses/marketplace-growth/details

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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) Ben’s background

(02:24) Defining a marketplace

(07:52) Challenges in building a marketplace

(13:28) Methods for growing supply

(15:57) Understanding marketplace liquidity

(21:36) Identifying product-market fit in marketplaces

(24:10) Evaluating marketplace business models

(27:20) Common pitfalls and failures in marketplaces

(36:23) Managed marketplaces and quality control

(42:26) Lyft’s rental car initiative

(46:35) Mentorship and ambassador programs

(51:21) Driver recruitment strategies

(54:12) Lyft vs. Uber: a strategic analysis

(59:24) Cultural differences in tech: Europe vs. U.S.

(01:10:30) Building a health advocacy platform

(01:16:52) Lightning round and final thoughts

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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.

Tamar Yehoshua is the president of product and technology at Glean. Prior to joining Glean, Tamar was chief product officer at Slack, where she led product, design, and research as the company scaled, including a 10x increase in revenue, its public listing, and an acquisition by Salesforce. She also led product and engineering teams at Google, working on search, identity, and privacy, and at A9.com, an Amazon company. Tamar has served on the board of directors for RetailMeNot, ServiceNow, Snyk, and Yext. In our conversation, we discuss:

• Why you don’t need to be a well-run company to win

• The impact of AI on product management and the future of work

• How to build strong cross-functional relationships, especially with engineers

• Lessons learned from working with leaders like Jeff Bezos and Stewart Butterfield

• Strategies for staying ahead in a rapidly evolving tech landscape

• Much more

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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/you-dont-need-to-be-a-well-run-company-to-win-tamar-yehoshua

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Where to find Tamar Yehoshua:

• X: https://x.com/TYehoshua

• LinkedIn: https://www.linkedin.com/in/tamar-yehoshua-886217/

• Newsletter: https://tamaryehoshua.substack.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) Tamar’s background

(02:09) Key advice for career success

(06:54) Understanding people and motivations

(09:33) The importance of impact

(11:20) Navigating company chaos

(18:40) Career planning: a different perspective

(26:22) Lessons from industry leaders

(37:59) Building stronger cross-functional relationships

(42:00) Streamlining OKR reviews with async methods

(45:26) Why you shouldn’t worry so much about making users unhappy

(47:50) The power of listening in leadership

(52:34) How to leverage AI so you don’t fall behind

(01:06:39) Closing thoughts and lightning round

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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.

Tal Raviv is a product manager at Riverside, where he joined as its first PM. Over his 12-year career as an individual contributor, Tal has been an early PM at Patreon, AppsFlyer, and Wix, working in consumer growth, developer API platforms, and pricing. He started his career by co-founding a profitable SaaS company and also volunteers as a surf instructor for people with disabilities. In our conversation, Tal shares:

• Why he has chosen to stay an individual contributor rather than moving into management

• The rise of “super ICs” and how companies can support this career path

• Advice for succeeding as a long-term IC product manager

• How he uses AI to enhance his productivity

• How to build self-reliant teams and make yourself redundant

• Lessons from failures

• Much more

—

Brought to you by:

• Gamma—A new way to present, powered by AI

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

• Eppo—Run reliable, impactful experiments

—

Find the transcript and show notes at: https://www.lennysnewsletter.com/p/the-super-ic-pm-tal-raviv

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Where to find Tal Raviv:

• X: https://x.com/talraviv

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

• Maven course: https://maven.com/tal-raviv/product-manager-productivity-system/

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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) Tal’s background

(02:24) Choosing to stay an IC product manager

(07:05) The value of IC roles

(08:31) Compensation and career path

(12:37) Advice for companies on creating space for ICs

(14:33) Leveraging AI for productivity

(22:44) Build your personal PM productivity system

(37:39) Contrarian opinions and insights

(44:32) Book smart vs. street smart decision-making

(51:51) There’s no one right way to get things done

(57:03) Failure corner

(01:19:04) Lightning round

(01:26:50) Living through conflict

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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.

Eli Schwartz is a leading SEO consultant and the author of Product-Led SEO. He has worked with industry giants like Zapier, Tinder, Coinbase, Quora, LinkedIn, and WordPress to build and execute global SEO strategies that significantly enhanced their organic visibility at scale. In our conversation, Eli shares:

• How AI and LLMs are reshaping the SEO landscape

• Why you should be focused on mid-funnel SEO strategies

• How to determine if SEO is the right approach for your business

• Why SEO should be treated as a product rather than just a marketing tactic

• SEO myths

• The future of search in light of recent legal challenges faced by Google

• Much more

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Brought to you by:

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

• Brave Search—A smarter way to search

• OneSchema—Import CSV data 10x faster

—

Find the transcript and show notes at: https://www.lennysnewsletter.com/p/rethinking-seo-in-the-age-of-ai-eli-schwartz

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Where to find Eli Schwartz:

• X: https://x.com/5le

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

• Website: https://www.elischwartz.co/

• Newsletter: https://www.productledseo.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/

—

In this episode, we cover:

(00:00) Eli’s background

(02:10) The impact of AI on SEO strategies

(11:34) Understanding search intent

(15:30) Real-world impact and structured vs. unstructured data

(20:19) Top-of-funnel vs mid-funnel SEO strategies

(22:57) Case studies

(31:29) Steps for getting started with SEO

(35:20) Examples of when not to focus on SEO

(39:17) Evaluating SEO investment

(44:00) Understanding the tradeoffs in marketing channels

(46:23) SEO conversion metrics and expectations

(52:09) Understanding the time horizon of SEO

(59:37) The role of AI in content creation

(01:05:26) AI overviews 

(01:07:40) Brand building and SEO

(01:09:51) Programmatic vs. editorial SEO strategies

(01:16:06) Insights from the Google antitrust verdict

(01:20:36) Google’s dominance in search

(01:23:52) The future of SEO and user choice

(01:26:28) SEO myths debunked

(01:36:58) Forecasting SEO success

(01:44:18) The need for SEO expertise

(01:46:26) Lightning round and closing thoughts

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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.

Camille Fournier is the author of The Manager’s Path, which many consider the definitive guide for navigating one’s career path in tech. Camille was previously the CTO of Rent the Runway, VP of Technology at Goldman Sachs, Head of Platform Engineering at Two Sigma, and Global Head of Engineering and Architecture at JPMorgan Chase. She is about to release new newest book, Platform Engineering: A Guide for Technical, Product, and People Leaders. In our conversation, we discuss:

• What product managers do that annoys engineers

• Why major rewrites are a trap

• Why you should have fewer one-on-ones

• Strategies for organizing and working with platform teams

• Tips for new managers

• Advice for transitioning from individual contributor to manager

• Much more

—

Brought to you by:

• DX—A platform for measuring and improving developer productivity

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

• Coda—The all-in-one collaborative workspace

—

Find the transcript and show notes at: https://www.lennysnewsletter.com/p/engineering-leadership-camille-fournier

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Where to find Camille Fournier:

• LinkedIn: https://www.linkedin.com/in/camille-fournier-9011812/

• Website: https://skamille.medium.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) Camille’s background

(02:17) Common annoyances between PMs and engineers

(07:09) Avoiding the telephone game

(08:05) Hoarding ideas and over-engineering

(09:55) The importance of involving engineers in ideation

(11:37) The middle-person dilemma

(14:21) Rewriting systems: a big trap?

(20:40) Engineering leadership lessons

(36:02) Moving from IC to management

(40:32) One-on-one meetings

(45:10) Pushing beyond comfort zones

(45:27) Building a balanced work culture

(48:01) Effective time management strategies

(54:15) Advice for platform team success

(01:02:42) Platform team responsibilities

(01:04:43) When to form a platform team

(01:07:02) Thriving on a platform team

(01:12:48) AI corner

(01:17:03) Lightning round and final thoughts

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Referenced:

• Platform Engineering: A Guide for Technical, Product, and People Leaders: https://www.amazon.com/Platform-Engineering-Technical-Product-Leaders/dp/1098153642/

• The Manager’s Path: A Guide for Tech Leaders Navigating Growth and Change: https://www.amazon.com/Managers-Path-Leaders-Navigating-Growth/dp/1491973897

• 97 Things Every Engineering Manager Should Know: Collective Wisdom from the Experts: https://www.amazon.com/Things-Every-Engineering-Manager-Should/dp/1492050903

• Avoiding the Rewrite Trap: https://skamille.medium.com/avoiding-the-rewrite-trap-b1283b8dd39e

• Levelsio on X: https://x.com/levelsio

• Pieter Levels on the Lex Fridman Podcast: https://www.youtube.com/watch?v=oFtjKbXKqbg

• GraphQL: https://graphql.org/

• New Blue Sun by André 3000 on Spotify: https://open.spotify.com/album/33Ek6daAL3oXyQIV1uoItD

• Musk’s 5 Steps to Cut Internal Bureaucracy at Tesla and SpaceX: https://icecreates.com/insight/musk-s-5-steps-to-cut-internal-bureaucracy-at-tesla-and-spacex-you-may-say-it-s-his-algorithm/

• Ian Nowland on LinkedIn: https://www.linkedin.com/in/inowland/

• Studio Pulls ‘Megalopolis’ Trailer Using Fake Quotes from Famed Movie Critics: https://www.huffpost.com/entry/studio-pulls-megalopolis-trailer-using-fake-quotes-from-famed-movie-critics_n_66c74046e4b0f1ca469413c7

• Claude 2: https://www.anthropic.com/news/claude-2

• What Got You Here Won’t Get You There: How Successful People Become Even More Successful: https://www.amazon.com/What-Got-Here-Wont-There/dp/1401301304

• When Things Fall Apart: Heart Advice for Difficult Times: https://www.amazon.com/When-Things-Fall-Apart-Difficult/dp/1611803438

• Alien: Romulus: https://www.imdb.com/title/tt18412256/

• Whoop: https://www.whoop.com

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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.

Phyl Terry is the author of Never Search Alone, which I’ve seen so many people reference as the most impactful guide they read for finding a job. Phyl was on the founding team of the first company Amazon acquired back in the ’90s and then was CEO of pioneering product consulting firm Creative Good, with companies like Apple, Facebook, and Microsoft as customers. Today, Phyl is the founder and CEO of Collaborative Gain, which 20 years ago pioneered bringing councils to senior product leaders and GMs in Silicon Valley. That’s their day job—in addition to that, Phyl runs a free global community for job seekers based on their latest book. In our conversation, we discuss:

• Why you should never search for a job alone

• How job search councils work

• How to determine your “candidate-market fit”

• How to conduct a listening tour

• Creating your job mission and OKRs

• How to negotiate job offers

• The art of asking for help

• Tactics for effective networking and interviewing

• Much more

—

Brought to you by:

• Sidebar—Accelerate your career by surrounding yourself with extraordinary peers

• Sprig—Build products for people, not data points

• Dovetail—The customer insights hub for product teams

—

Find the transcript and show notes at: https://www.lennysnewsletter.com/p/land-your-dream-phyl-terry

—

Where to find Phyl Terry:

• X: https://x.com/phylterry

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

• Website: https://www.phyl.org/

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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) Phyl’s background

(01:58) The concept of job search councils

(04:27) The power of community in job searching

(08:55) The scale and structure of job search councils

(12:27) The impact of job search councils

(20:19) The concept of candidate-market fit

(22:50) Writing a Mnookin two-pager

(24:37) Conducting listening tours

(30:12) Creating a focused candidate-market fit

(36:20) Advice on finding the right stage of company for you

(40:37) Identifying your unique path

(45:30) Navigating tough job markets

(49:07) Playing to win

(53:36) Negotiation tactics for job offers

(01:05:12) The gratitude house exercise

(01:10:48) The power of asking for help

(01:19:18) How to ask for help

(01:28:40) Final thoughts and advice

(01:38:21) Lightning round

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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.

Tomer Cohen is the chief product officer at LinkedIn, responsible for setting the company’s product strategy, leading product development, user experience design, business development, content creation, and customer operations. He also hosts the Building One podcast, where he interviews exceptional builders across various disciplines. In our conversation, we discuss:

• How LinkedIn transformed its feed into an engaging content and social platform

• Tomer’s famous “We might be wrong, but we are not confused” mantra

• The importance of conviction and passion in product leadership

• LinkedIn’s approach to experimenting with and implementing AI features

• Lessons from Tomer’s rapid career progression at LinkedIn

• Strategies for embracing AI in product development

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Brought to you by:

• Gamma—A new way to present, powered by AI

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

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

—

Find the transcript at: https://www.lennysnewsletter.com/p/how-linkedin-became-interesting-tomer-cohen

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Where to find Tomer Cohen:

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

• Podcast: https://podcasts.apple.com/us/podcast/building-one-with-tomer-cohen/id1726672498

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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 Tomer Cohen and his role at LinkedIn

(02:28) The mantra “We might be wrong, but we are not confused”

(06:45) Clarity of thought and focus

(13:03) Setting ambitious goals and overdelivering

(16:18) Transforming LinkedIn’s feed: strategy and execution

(22:03) Running experiments at scale

(26:24) Goal setting and identifying opportunities 

(30:58) AI’s role in LinkedIn’s evolution

(35:38) The AI-first mindset at LinkedIn

(35:38) Developing an AI-first mindset

(44:49) Letting go of your roadmaps and allowing room for exploration

(49:12) Career growth and personal insights

(55:01) Takeaways

(56:39) Lightning round and final thoughts

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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.

Sean Ellis is one of the earliest and most influential thinkers and operators in growth. He coined the term “growth hacking,” invented the ICE prioritization framework, was one of the earliest people to use freemium as a growth lever, and, most famously, developed the Sean Ellis Test for product-market fit (which a large percentage of founders use today to track if they’ve found PMF). Over the course of his career, Sean was head of growth at Dropbox and Eventbrite; helped companies like Microsoft and Nubank refine their growth strategy; was on the founding team of LogMeIn, which sold for over $4 billion; and is the author of one of the most popular growth books of all time, Hacking Growth, which has sold over 750,000 copies. In our conversation, he shares:

• The proper use of the Sean Ellis Test for measuring product-market fit

• How to increase your activation and retention rates

• How to select the right North Star metric for your business

• Case studies from his work growing Dropbox and other products

• How growth strategy has changed over the past decade

• How AI is impacting growth efforts

• Much more

—

Brought to you by:

• Gamma—A new way to present, powered by AI

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

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

—

Find the transcript and show notes at: https://www.lennysnewsletter.com/p/the-original-growth-hacker-sean-ellis

—

Where to find Sean Ellis:

• X: https://x.com/seanellis

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

• Website: https://www.seanellis.me/

• Substack: https://substack.com/@seanellis

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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) Sean’s background

(02:18) The Sean Ellis test explained

(06:28) The 40% rule

(08:06) Case study: improving product-market fit

(12:34) Understanding and leveraging customer feedback

(16:50) Challenges and nuances of product-market fit

(22:22) When to use the Sean Ellis Test

(23:46) When not to use the Sean Ellis Test and other caveats

(27:13) Defining your own threshold and how the Sean Ellis Test came about

(36:13) Tools for implementing the survey 

(37:30) Transitioning from surveys to retention cohorts

(39:13) Nubank’s approach

(40:18) Case study: Superhuman’s strategy for increasing product-market fit

(45:18) Coining the term “growth hacking”

(48:24) How to approach growth

(57:25) Improving activation and onboarding

(01:05:17) Identifying effective growth channels

(01:10:28) The power of customer conversations

(01:12:43) Developing the Dropbox referral program

(01:14:47) The importance of word of mouth

(01:15:23) Freemium models and engagement

(01:19:21) Picking a North Star metric

(01:24:30) The evolution of growth strategies

(01:27:12) The ICE and RICE frameworks

(01:30:11) AI’s role in growth and experimentation

(01:32:52) Final thoughts and lightning round

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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.

Vlad Loktev spent 10 years at Airbnb, where he started as an IC PM and quickly advanced to lead the core Airbnb marketplace business and then GM the entire homes business, managing over 1,000 people and reporting directly to CEO Brian Chesky. He recently left Airbnb and joined Index Ventures as their newest partner. Vlad was my manager at Airbnb for many years, and is the person I credit most for teaching me how to be a great product manager. Prior to Airbnb, Vlad spent a year at Zynga, where he helped grow Words with Friends to over 14 million daily active users. In our conversation, Vlad shares:

• Insight into Brian Chesky’s leadership style

• Why success as a PM is all about impact, impact, impact

• Why chaos can be good

• Why as a leader it’s OK to let some fires burn

• Why you should learn to “poke the bear”

• Balancing product release speed with quality

• Lessons on prioritization, decision-making, and organizational design

• Advice for founders on building company culture

• 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

• Eppo—Run reliable, impactful experiments

—

Find the transcript and show notes at: https://www.lennysnewsletter.com/p/impact-impact-impact-vlad-loktev

—

Where to find Vlad Loktev:

• X: https://x.com/vladimirloktev

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

—

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) Vlad’s background

(02:54) Reflecting on transformative years at Airbnb

(04:28) Skills and mindsets for success

(11:03) Impact-driven mindset

(13:16) Saying no and inquiry before advocacy 

(17:54) “Poking the bear”

(22:46) Psychological tools for leadership

(30:08) Building and scaling teams

(36:12) Letting fires burn

(47:34) Embracing chaos

(54:40) The unsell email strategy

(01:02:01) Finding your place in an organization

(01:05:38) The importance of company culture

(01:13:16) Airbnb’s unique approach to product management

(01:26:41) Failure corner

(01:31:32) Lightning round and final thoughts

—

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

—

Lenny may be an investor in the companies discussed.

Nikita Bier is one of the most in-demand consumer, social, and growth experts in the world. He’s the co-founder of TBH (sold to Meta for more than $30 million) and Gas (sold to Discord for millions more) and has helped more consumer apps that have hit #1 in the app stores than any other person I’ve come across. He currently spends his time advising founders on growth, product, and design and is an investor and advisor to some of the best consumer tech companies, including Flo, Locket, Eight Sleep, Citizen, BeReal, Captions, and more. In our conversation, we discuss:

• The inside story of how TBH and Gas achieved explosive growth

• Strategies for building viral consumer apps

• Why teens are such a great audience

• Fighting the human trafficking hoax at Gas

• The challenge of creating durable social products

• His experience working as a PM at Facebook

• Advice for founders on building consumer apps

• Much more

—

Brought to you by:

• Webflow—The web experience platform

• Vanta—Automate compliance. Simplify security

• Explo—Embed customer-facing analytics in your product

—

Book Nikita for 1:1 consultation/mentoring: https://intro.co/NikitaBier

—

Find the transcript and show notes at: https://www.lennysnewsletter.com/p/how-to-consistently-go-viral-nikita-bier

—

Where to find Nikita Bier:

• X: https://x.com/nikitabier 

• Threads: https://www.threads.net/@nikitabier

• Website: https://intro.co/NikitaBier

—

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) Nikita’s background 

(06:08) Nikita’s early ventures: Politify and Outline

(08:42) Transition to consumer apps

(13:45) The birth of TBH

(16:43) Building for teens vs. adults

(20:00) TBH’s viral success

(32:18) Leveraging live chat

(34:08) Lasting lessons from TBH

(37:00) Selling TBH to Facebook

(42:19) Big-tech product management

(48:46) Nikita on why “product management is not real”

(51:49) The Tim Cook painting story

(53:53) Leaving Facebook and starting a new venture

(58:02) Rebuilding TBH and overcoming challenges

(59:46) Addressing criticism

(01:04:24) The human trafficking hoax

(01:09:51) Selling to Discord and lessons learned

(01:11:36) Lasting lessons from Gas

(01:13:14) Building durable consumer apps

(01:22:35) The VC route

(01:23:27) Contact permissions in iOS 18

(01:26:53) The success of Dupe

(01:31:53) Advice for startup founders

(01:34:14) Work with Nikita

—

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.

Deb Liu is the CEO of Ancestry and former longtime VP of Product at Facebook. At Facebook, Deb led the creation of Facebook Marketplace, developed the first mobile ad product for apps, built the company’s games business, and launched Facebook Pay. She’s also held leadership roles at PayPal and eBay, serves on the board of Intuit, and is the author of Take Back Your Power. In our conversation, we discuss:

• Why you should PM your career like you PM your product

• Strategies for incubating new products within large companies

• Creating a successful 30-60-90-day plan when starting a new job

• The pitfalls of perfectionism

• The challenges introverts face in the workplace and how to overcome them

• The value of resilience and turning failures into stepping stones

• How to leverage coaching in your career development

—

Brought to you by:

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

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

• Webflow—The web experience platform

—

Find the transcript and show notes at: https://www.lennysnewsletter.com/p/succeeding-as-an-introvert-deb-liu

—

Where to find Deb Liu:

• Threads: https://www.threads.net/@debliu

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

• Substack: https://debliu.substack.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 Deb Liu

(02:18) Deb’s career journey and key advice

(09:45) Navigating new roles and challenges

(11:27) Overcoming adversity and failure

(15:07) Building billion-dollar businesses at Facebook

(19:33) Strategies for zero-to-one innovation

(23:40) PM your career like a product

(33:53) Challenges and strategies for introverts in business

(39:19) Reframing self-promotion

(42:25) The power of accountability

(46:15) Growth: a game of inches

(50:52) The 30-60-90-day plan

(56:52) Contrarian corner: career and marriage

(58:57) Final nuggets of wisdom

(01:03:09) How to find a coach

(01:04:47) Lightning round

—

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

—

Lenny may be an investor in the companies discussed.

Kevin Yien leads product for merchant experiences at Stripe. Before that, he meandered his way from being a technical designer to a product manager, built the restaurants business and ecosystem team at Square, and most recently was head of product and design at Mutiny. He also makes ice cream and teaches for fun. In our conversation, we discuss:

• Why aspiring PMs should start in engineering, design, or sales

• The importance of writing skills, and how to become a better writer

• How to automate user research

• Kevin’s “unsell email” technique for hiring

• The value of keeping a decision log

• Insights on AI and its impact on future generations

• Lessons from failure

—

Brought to you by:

• BuildBetter—AI for product teams

• OneSchema—Import CSV data 10x faster

• Eppo—Run reliable, impactful experiments

—

Find the transcript and show notes at: https://www.lennysnewsletter.com/p/unorthodox-pm-wisdom-kevin-yien

—

Where to find Kevin Yien:

• X: https://x.com/kevinyien

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

• Website: https://kevinyien.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) Kevin’s background 

(02:00) The story behind Kevin’s profile picture

(08:41) The role of a product manager

(10:48) Getting started in product management

(12:47) The importance of writing skills

(15:06) Becoming a better writer

(19:10) The PM’s role with engineering and design

(28:41) Drawing the perimeter for your team

(31:37) Feedback tips

(35:13) Decision logs and product sense

(45:36) Unorthodox hiring strategies

(47:01) The unsell email strategy

(54:01) Automating user research

(01:02:27) AI in everyday life

(01:06:05) Lessons from failure

(01:14:34) Lightning round

—

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

—

Lenny may be an investor in the companies discussed.

Evan LaPointe is the founder of CORE Sciences, which teaches companies and individuals how our brains work and how that translates to improved collaboration, better products, faster decision-making, and more growth. Previously, Evan was the co-founder of Satellite, the fourth-largest analytics product on the internet today (it mostly runs behind the scenes, and pretty much everyone listening will have used it today without knowing it), which was acquired by Adobe, where he later ran product strategy, innovation, and long-range thinking for Adobe’s digital experiences business. In our conversation, we discuss:

• The three different systems of the brain

• How knowing this can help you become more influential

• How understanding different brain states will help you increase productivity and creativity

• How to improve your vision and strategy skills

• How to design a work environment that fosters innovation

• How to build better relationships at work

• Much more

—

Use discount code “LENNY” for $5 off the CORE Sciences personality profile: https://www.core-sciences.com/new-core-identity

—

Brought to you by:

• Webflow—The web experience platform

• Explo—Embed customer-facing analytics in your product

• Eppo—Run reliable, impactful experiments

—

Find the transcript and references at: https://www.lennysnewsletter.com/p/understanding-your-brain-evan-lapointe

—

Where to find Evan LaPointe:

• X: https://x.com/evanlapointe

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

• Website: https://www.core-sciences.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) Evan’s background

(02:37) Understanding the brain’s complex systems

(07:17) The three core brain systems: safety, reward, and purpose

(11:03) Applying brain science to team dynamics

(14:27) The role of personality in team performance

(17:27) Creating effective work environments

(23:16) The science of meetings and decision-making

(29:35) Enhancing strategy and vision

(54:46) Understanding personality traits in strategy and vision

(58:58) Tactical tips for increasing openness

(01:05:46) Building influence and effective relationships

(01:21:17) The importance of trust and appeal in relationships

(01:36:47) Creating a positive organizational habitat

(01:50:35) Enhancing focus and productivity

(02:00:58) Practical tips for deep work and gamma time

(02:07:11) Lightning round

—

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

—

Lenny may be an investor in the companies discussed.

Joe Hudson is one of the most sought-after executive coaches in Silicon Valley. He is the founder of Art of Accomplishment, a transformational coaching program that has helped tens of thousands of people, including many tech executives and founders from companies like Apple, OpenAI, and Google. His unique method of transformation comes from over 25 years of exploring neurological, psychological, and spiritual traditions, tested against real-world challenges. In our conversation, Joe shares:

• Why the critical voice in your head is always wrong, and how to change your relationship with that voice

• Why authenticity trumps self-improvement

• The importance of embracing all of your emotions

• How to create more enjoyable and effective meetings

• The power of gratitude in transforming your life

• Practical experiments for personal growth

• Much more

—

Apply for Joe’s Connection Course:

Thousands of students have taken Joe’s most popular experience, the Connection Course. Unlike most online courses, there is no reading, lectures, or written homework. It is a three-week experiential deep dive where you will apply your learnings to real-life problems—how to make your team more productive, communicate more effectively, and resolve conflicts with ease. Apply here and use the code LENNY for $300 off your enrollment: view.life/lenny.

—

Brought to you by:

• BuildBetter—AI for product teams

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

• Coda—The all-in-one collaborative workspace

—

Find the transcript and references at: https://www.lennysnewsletter.com/p/embracing-your-emotions-joe-hudson

—

Where to find Joe Hudson:

• X: https://x.com/FU_joehudson

• LinkedIn: https://www.linkedin.com/in/joe-hudson/

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

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

• Linktree: https://linktr.ee/theartofaccomplishment

—

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) Joe’s background

(02:31) The critical voice in your head

(06:39) Changing your relationship with the critical voice

(13:19) Understanding and embracing emotions

(19:52) The importance of emotional fluidity

(24:40) Questioning assumptions and self-perception

(30:25) The consequences of avoiding emotions

(36:57) Experimenting with self-improvement

(39:42) Understanding efficiency and enjoyment

(43:17) The power of enjoyment in daily tasks

(45:03) Innate enjoyment vs. learned enjoyment

(46:31) Authenticity vs. self-improvement

(50:01) Embracing emotional experiences

(55:49) How understanding your emotions helps you make better decisions

(01:02:53) Creating effective teams and meetings

(01:10:40) Gratitude practice for personal growth

(01:15:36) Conclusion and final thoughts

—

Lenny may be an investor in the companies discussed.

Brian Tolkin is the Head of Product at Opendoor. Previously, he was one of the early employees at Uber, where he was instrumental in launching and growing UberPool, UberHop, and UberExpress and started one of the first product operations teams in tech. In our conversation, we dive into:

• How to enable product and ops to work well together

• How to run great product reviews

• How to make good decisions with limited data

• How he uses the jobs-to-be-done framework at Opendoor

• How to stay calm under pressure as a leader

• Wild stories from his time at Uber

• Challenges faced at Opendoor during the pandemic

• Much more

—

Brought to you by:

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

• Explo—Embed customer-facing analytics in your product

• Attio—The powerful, flexible CRM for fast-growing startups

—

Find the transcript and references at: https://www.lennysnewsletter.com/p/scaling-uber-and-opendoor-brian-tolkin

—

Where to find Brian Tolkin:

• X: https://x.com/briantolkin

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

—

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) Brian’s background

(02:14) Career beginnings at Uber

(02:49) Transitioning from product operations to product management

(06:47) Product and operations synergy

(10:00) Surge pricing at Uber

(12:18) Scaling challenges, and stories

(15:47) Opendoor and Covid adaptations

(25:38) Product reviews and Jobs to Be Done

(40:30) The challenges of A/B testing

(42:23) Increasing conviction in solutions

(44:33) Leveraging intuition in product decisions

(47:07) Partnering with Zillow

(52:55) Staying calm under pressure

(56:25) Finding the “kernel of truth” in product management

(01:00:21) Failure corner: Early days of Uber Pool

(01:06:11) Lightning round and final thoughts

—

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

—

Lenny may be an investor in the companies discussed.

Timothy Davis has led performance marketing for all of Shopify for the past 2.5 years, and as a consultant has helped companies like Pinterest, LinkedIn, Redfin, and Eventbrite kickstart and scale their performance marketing teams. In every one of those cases, he got them so performant at paid growth that they significantly scale spend and investment in these channels. In our conversation, we cover:

• When and how to start investing in performance marketing

• Common mistakes companies make with paid ads

• How to build and structure a performance marketing team

• How to get your creatives performing better

• Strategies for optimizing workflows and team efficiency

• How AI will change performance marketing

• Much more

—

Brought to you by:

• BuildBetter—AI for product teams

• OneSchema—Import CSV data 10x faster

• Eppo—Run reliable, impactful experiments

—

Find the transcript and references at: https://www.lennysnewsletter.com/p/performance-marketing-timothy-davis

—

Where to find Timothy Davis:

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

—

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) Timothy’s background 

(02:31) Understanding performance marketing 

(06:31) The importance of paid search 

(08:39) Identifying growth potential 

(09:54) Case studies: Hairstory and Ipsy 

(12:22) Experimenting with new platforms 

(18:57) Choosing the right platforms 

(20:23) LinkedIn for B2B marketing 

(27:56) When to start investing in paid growth 

(33:33) Common mistakes in performance marketing 

(37:41) Working with agencies and consultants 

(40:36) Hiring for performance marketing 

(47:33) Metrics that matter 

(54:43) Competitor analysis and CPC insights 

(56:15) Custom reports and data visualization

(56:38) Understanding impression and click share 

(59:10) True competition metrics 

(01:02:14) Attribution and incrementality 

(01:08:52) Building a performance marketing team 

(01:10:53) Creative and ad copy collaboration 

(01:15:48) Managing workload and hiring strategy 

(01:20:52) Training and onboarding new hires 

(01:24:41) Impact of ATT on performance marketing 

(01:25:56) The power of creative in ads 

(01:29:47) Using AI in performance marketing 

(01:37:16) Lightning round 

—

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

—

Lenny may be an investor in the companies discussed.

Roger Martin is one of the world’s leading experts on strategy and the author of Playing to Win, one of the most beloved books on strategy. He’s written extensively for the Harvard Business Review; consulted for dozens of Fortune 500 companies, including P&G, Lego, and Ford; and written 11 other books. In our conversation, we discuss:

• The five key questions you need to answer to develop an effective strategy

• Why most companies get strategy wrong

• How to avoid “playing to play” instead of playing to win

• Real-world strategy examples from Procter & Gamble, Southwest Airlines, Lego, and Figma

• How to think about differentiation vs. low cost

• Shortcomings of current strategy education

• Much more

—

Correction: Roger pointed out that he made an error during our chat. When I asked him about Richard Rumelt (~16 mins), he thought I said Richard D'Aveni.

—

Brought to you by:

• Webflow—The web experience platform

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

• Cycle—Your feedback hub, on autopilot

—

Find the transcript at: https://www.lennysnewsletter.com/p/the-ultimate-guide-to-strategy-roger-martin

—

Where to find Roger Martin:

• X: https://x.com/RogerLMartin

• LinkedIn: https://www.linkedin.com/in/roger-martin-9916911a9/

• Website: https://rogerlmartin.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) Roger’s background

(02:20) The importance of strategy

(07:00) Challenges in developing strategy

(08:30) Critique of modern strategy education

(14:00) Hamilton Helmer and Richard Rumelt

(17:40) Defining strategy

(19:12) The Strategy Choice Cascade

(23:20) Playing to win vs. playing to play

(24:57) Examples of strategic success

(30:49) Differentiation and moats

(40:23) Applying strategy to real-world scenarios

(43:47) Customer-centric strategy

(44:45) Defining the market and product

(45:59) Value chain and distribution

(48:28) Cost leadership vs. differentiation

(53:16) Capabilities and management systems

(57:14) Competitive advantage and market positioning

(01:02:41) Counterpositioning and fault lines

(01:05:53) Adapting to AI and market changes

(01:14:11) Betterment over perfection

(01:18:42) Final thoughts on strategy

—

Referenced:

• Nearly 10% of S&P 500 CEOs are alumni of Procter & Gamble: https://www.bizjournals.com/cincinnati/news/2023/02/06/10-of-s-p-500-ceos-pg.html

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

• Figma: https://www.figma.com/

• What Is Resource-Based Theory?: https://www.igi-global.com/dictionary/the-impact-of-technological-governance-and-political-capabilities-on-firms-performances-under-economic-turbulence/67915

• Michael Porter on LinkedIn: https://www.linkedin.com/in/professorporter/

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

• VRIO Framework Explained: https://strategicmanagementinsight.com/tools/vrio/

• Business strategy with Hamilton Helmer (author of 7 Powers): https://www.lennysnewsletter.com/p/business-strategy-with-hamilton-helmer

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

• 7 Powers: The Foundations of Business Strategy: https://www.amazon.com/7-Powers-Foundations-Business-Strategy/dp/0998116319

• Boston Consulting Group: https://www.bcg.com/

• Bruce Henderson: https://en.wikipedia.org/wiki/Bruce_Henderson

• Lego: https://www.lego.com

• Vanguard: https://investor.vanguard.com/

• Southwest Airlines: https://www.southwest.com/

• How Amazon Managed to Dethrone Walmart: https://www.nytimes.com/interactive/2021/08/20/technology/how-amazon-beat-walmart.html

• GM Lost a 10-Year Battle with Tesla, Pulling the Plug on a Long Line of EVs: https://www.forbes.com/sites/brookecrothers/2023/07/09/gm-killed-its-electric-cars-and-lost-a-10-year-battle-with-tesla/

• Westlaw: https://www.westlawinternational.com/

• What Is an Economic Moat? Why Warren Buffett Says It Matters for Investors: https://finance.yahoo.com/news/economic-moat-why-warren-buffett-160046125.html

• Salomon Brothers: https://en.wikipedia.org/wiki/Salomon_Brothers

• US Airways: https://en.wikipedia.org/wiki/US_Airways

• Four Seasons: https://www.fourseasons.com/

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

• Bill Gates on LinkedIn: https://www.linkedin.com/in/williamhgates/

• Mandarin Oriental: https://www.mandarinoriental.com/en/

• Continental Lite: https://en.wikipedia.org/wiki/Continental_Lite

• Ted (airline): https://en.wikipedia.org/wiki/Ted_(airline)

• Case Study: Oil of Olay: https://www.studocu.com/es/document/universidad-de-murcia/estrategia-de-marketing/case-study-old-of-olay/95079369

• AG Lafley on LinkedIn: https://www.linkedin.com/in/ag-lafley-2381b3201/

• Jack Bogle: https://en.wikipedia.org/wiki/John_C._Bogle

• Seven Ways Windows 95 Changed the World: https://www.forbes.com/sites/ianmorris/2015/08/24/windows-95-changed-the-world/

• Where to Start with Strategy? Focus on Betterment: https://rogermartin.medium.com/where-to-start-with-strategy-bae40506304c

• Brick by brick: The man who rebuilt the house of Lego shares his leadership secrets: https://www.washingtonpost.com/news/on-leadership/wp/2016/12/08/brick-by-brick-the-man-who-rebuilt-the-house-of-lego-shares-his-leadership-secrets/

• A New Way to Think: Your Guide to Superior Management Effectiveness: https://www.amazon.com/New-Way-Think-Management-Effectiveness/dp/164782351X/

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

• The Design of Business: Why Design Thinking Is the Next Competitive Advantage: https://www.amazon.com/Design-Business-Thinking-Competitive-Advantage/dp/1422177807

• The Opposable Mind: How Successful Leaders Win Through Integrative Thinking: https://www.amazon.com/Opposable-Mind-Successful-Integrative-Thinking/dp/1422118924

• When More Is Not Better: Overcoming America’s Obsession with Economic Efficiency: https://www.amazon.com/When-More-Not-Better-Overcoming/dp/1647820065

—

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.

Rory Sutherland is widely regarded as one of the most influential (and most entertaining) thinkers in marketing and behavioral science. He’s the vice chairman of Ogilvy UK, the author of Alchemy: The Dark Art and Curious Science of Creating Magic in Brands, Business, and Life, and the founder of Nudgestock, the world’s biggest festival of behavioral science and creativity. He champions thinking from first principles and using human psychology—what he calls “thinking psycho-logically”—over mere logic. In our conversation, we cover:

• Why good products don’t always succeed, and bad ones don’t necessarily fail

• Why less functionality can sometimes be more valuable

• The importance of fame in building successful brands

• The importance of timing in product success

• The concept of “most advanced, yet acceptable”

• Why metrics-driven workplaces can be demotivating

• Lots of real-world case studies

• Much more

Note: We encountered some technical difficulties that led to less than ideal video quality for this episode, but the lessons from this conversation made it impossible for me to not publish it anyway. Thanks for your understanding and for bearing with the less-than-ideal video quality. 

—

Brought to you by:

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

• Cycle—Your feedback hub, on autopilot

• Coda—The all-in-one collaborative workspace

—

Find the transcript at: https://www.lennysnewsletter.com/p/what-most-people-miss-about-marketing

—

Where to find Rory Sutherland:

• X: https://x.com/rorysutherland

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

• Book: Alchemy: The Dark Art and Curious Science of Creating Magic in Brands, Business, and Life: https://www.amazon.com/Alchemy-Curious-Science-Creating-Business/dp/006238841X

—

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) Rory’s background

(02:37) The success and failure of products

(04:08) Why the urge to appear serious can be a disaster in marketing

(08:05) The role of distinctiveness in product design

(12:29) The MAYA principle

(15:50) How thinking irrationally can be advantageous

(17:40) The fault of multiple-choice tests

(21:31) Companies that have successfully implemented out-of-the-box thinking

(30:31) “Psycho-logical” thinking

(31:45) The hare and the dog metaphor

(38:51) Marketing’s crucial role in product adoption

(49:21) The quirks of Google Glass

(55:44) Survivorship bias

(56:09) Balancing rational ideas with irrational ideas

(01:06:19) The rise and fall of tech innovations

(01:09:54) Consistency, distinctiveness, and clarity

(01:21:12) Considering psychological, technological, and economic factors in parallel

(01:23:35) Where to find Rory

—

Referenced:

• Google Glass: https://en.wikipedia.org/wiki/Google_Glass

• Meta Portal TV: https://www.meta.com/portal/products/portal-tv/

• Rory’s quote in a LinkedIn post: https://www.linkedin.com/posts/brad-jackson-04766642_the-urge-to-appear-serious-is-a-disaster-activity-7093497742710210560-1LYN/

• The MAYA Principle: Design for the Future, but Balance It with Your Users’ Present: https://www.interaction-design.org/literature/article/design-for-the-future-but-balance-it-with-your-users-present

• Ogilvy: https://www.ogilvy.com/

• MCI: https://www.mci.world/

• Veuve Clicquot: https://en.wikipedia.org/wiki/Veuve_Clicquot

• Why do the French call the British ‘the roast beefs’?: http://news.bbc.co.uk/2/hi/2913151.stm

• The Killing on Hulu: https://www.hulu.com/series/the-killing-f5da5c2d-4626-4ba9-bcf3-ff5f891771fb

• Original The Killing on BBC: https://www.bbc.co.uk/programmes/b017h7m1

• The Mandarin Oriental, Hong Kong: https://www.mandarinoriental.com/en/hong-kong/victoria-harbour

• SAT: https://satsuite.collegeboard.org/sat

• The Widening Racial Scoring Gap on the SAT College Admissions Test: https://www.jbhe.com/features/49_college_admissions-test.html

• What is the age of the captain?: https://www.icopilots.com/what-is-the-age-of-the-captain/

• Octopus Energy: https://octopus.energy/

• Kraken: https://octopusenergy.group/kraken-technologies

• Toby Shannan: https://theorg.com/org/shopify/org-chart/toby-shannan

• Dunbar’s number: Why we can only maintain 150 relationships: https://www.bbc.com/future/article/20191001-dunbars-number-why-we-can-only-maintain-150-relationships

• AO: https://ao.com/

• Zappos: https://www.zappos.com/

• Joe Cano on LinkedIn: https://www.linkedin.com/in/joeycano/

• John Ralston Saul’s website: https://www.johnralstonsaul.com/

• Voltaire’s Bastards: The Dictatorship of Reason in the West: https://www.amazon.com/Voltaires-Bastards-Dictatorship-Reason-West/dp/0679748199

• Psycho-Logic: Why Too Much Logic Deters Magic: https://coffeeandjunk.com/psycho-logic/

• Herbert Simon’s Decision-Making Approach: https://bura.brunel.ac.uk/bitstream/2438/4995/1/Fulltext.pdf

• Robert Trivers’s website: https://roberttrivers.com/Welcome.html

• Crazy Ivan: https://jollycontrarian.com/index.php?title=Crazy_Ivan

• The Joys of Being a Late Tech Adopter: https://www.nytimes.com/2019/08/28/technology/personaltech/joys-late-tech-adopter.html

• Jean-Claude Van Damme: https://en.wikipedia.org/wiki/Jean-Claude_Van_Damme

• Tim Berners-Lee: https://en.wikipedia.org/wiki/Tim_Berners-Lee

• Edward Jenner and the history of smallpox and vaccination: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1200696/

• The real story behind penicillin: https://www.pbs.org/newshour/health/the-real-story-behind-the-worlds-first-antibiotic

• What Are Japanese Toilets?: https://www.bigbathroomshop.co.uk/info/blog/japanese-toilets/

• reMarkable: https://remarkable.com/

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

• Survivorship bias: https://en.wikipedia.org/wiki/Survivorship_bias

• Jony Ive: https://en.wikipedia.org/wiki/Jony_Ive

• Marc Newson’s website: https://marc-newson.com/

• Designing Men: https://www.vanityfair.com/news/business/2013/11/jony-ive-marc-newson-design-auction

• Qantas A330: https://marc-newson.com/qantas-a330/

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

• Big Decision? Consider It Both Drunk and Sober: https://www.forbes.com/sites/chunkamui/2016/03/22/wine-and-sleep-make-for-better-decisions/?sh=5c97fdc524b1

• How Henry Ford and Thomas Edison killed the electric car: https://www.speakev.com/threads/how-henry-ford-and-thomas-edison-killed-the-electric-car.4270/

• Watch Jay Leno get nostalgic and swoon over this 1909 EV: https://thenextweb.com/news/jay-leno-talk-about-electric-car-1909-baker

• Jay Leno’s Garage: https://www.youtube.com/@jaylenosgarage

• Nudgestock: https://nudgestock.com/

• Akio Morita: https://en.wikipedia.org/wiki/Akio_Morita

• Don Norman on LinkedIn: https://www.linkedin.com/in/donnorman/

• What Makes Tesla’s Business Model Different: https://www.investopedia.com/articles/active-trading/072115/what-makes-teslas-business-model-different.asp

• Monica Lewinsky on X: https://x.com/MonicaLewinsky

• Blindsight: The (Mostly) Hidden Ways Marketing Reshapes Our Brains: azon.com/Blindsight-Mostly-Hidden-Marketing-Reshapes-ebook/dp/B07ZKZ5DWF

• Branding That Means Business: https://www.amazon.com/Branding-that-Means-Business-Economist-ebook/dp/B09QBCCH9N

• PwC: https://www.pwc.com

• Ryanair: https://www.ryanair.com

• British Airways: https://www.britishairways.com/

• Wrigley’s began as a soap business: know when to pivot: https://theamericangenius.com/entrepreneur/wrigleys-began-as-soap-know-when-to-pivot/

• Transport for Humans: https://www.amazon.com/Transport-Humans-Perspectives-Pete-Dyson/dp/1913019357

—

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.

Jessica Lachs is the global head of analytics and data science at DoorDash, where she’s built one of the largest and most respected data organizations in tech. In her more than 10 years at DoorDash, she has served as the first general manager, responsible for launching new markets; the head of business ops and analytics; and the VP of analytics and data science. Previously, Jessica founded GiftSimple, a social gifting startup, and started her career at Lehman Brothers as an investment banking analyst. In our conversation, she shares:

• How to structure and scale a high-impact analytics organization

• Centralized vs. decentralized data teams

• How to pick the right metric and aligning incentives

• Advice for data people on how and when to push back

• Lessons learned from building a global data team

• How to foster a culture of extreme ownership

• The role of AI in improving analytics team productivity

• Advice for aspiring data leaders without formal training

—

Brought to you by:

• Webflow—The web experience platform

• Anvil—The fastest way to build software for documents

• Attio—The powerful, flexible CRM for fast-growing startups

—

Find the transcript at: https://www.lennysnewsletter.com/p/building-a-world-class-data-org-jessica-lachs

—

Where to find Jessica Lachs:

• X: https://x.com/jesslachs

• LinkedIn: https://www.linkedin.com/in/jessica-lachs/

—

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

(04:59) Centralized vs. embedded analytics teams

(10:52) The benefits of a centralized analytics team

(15:10) Balancing proactive and reactive work

(20:45) Advice on how to push back effectively

(24:20) Hiring for curiosity and problem solving

(28:57) Coming from a non-traditional background

(34:40) The early days and culture at DoorDash

(40:39) Encouraging cross-functional roles

(44:39) Defining effective metrics

(46:30) Simplifying metrics for better outcomes

(55:28) Focusing on edge cases and fail states

(01:00:12) Managing a global data organization

(01:02:31) Leveraging AI for productivity

(01:05:25) Building diverse and skilled data teams

(01:08:40) Lightning round

—

Referenced:

• How Netflix builds a culture of excellence | Elizabeth Stone (CTO): https://www.lennysnewsletter.com/p/how-netflix-builds-a-culture-of-excellence

• Riley Newman on LinkedIn: https://www.linkedin.com/in/rileynewman/

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

• Imposter Syndrome: Why You May Feel Like a Fraud: https://www.verywellmind.com/imposter-syndrome-and-social-anxiety-disorder-4156469

• Stanley Tang on LinkedIn: https://www.linkedin.com/in/stanleytang/

• Andy Fang on LinkedIn: https://www.linkedin.com/in/fangsterr/

• Evan Moore on LinkedIn: https://www.linkedin.com/in/evanmoore/

• How WeDash became the flagship employee program for DoorDash: https://careers.doordash.com/blog/wedash-doordash-employee-program-how-does-it-work

• Leading with empathy | Keith Yandell (DoorDash, Uber): https://www.lennysnewsletter.com/p/leading-with-empathy-keith-yandell

• The Rose Code: https://www.amazon.com/Rose-Code-Novel-Kate-Quinn/dp/006305941X

• Libby app: https://libbyapp.com/

• The West Wing on Prime: https://www.amazon.com/West-Wing-Complete-First-Season/dp/B000KZPG04

• Alias on Prime: https://www.amazon.com/Alias-Season-1/dp/B00748O13S

• Joseon sunscreens: https://beautyofjoseon.com/

• Innisfree sunscreens: https://us.innisfree.com/

• John Steinbeck quote: https://www.brainyquote.com/quotes/john_steinbeck_103825

• Vanessa Roberts on LinkedIn: https://www.linkedin.com/in/vanessa-roberts-b8a509a/

• Tia Sherringham on LinkedIn: https://www.linkedin.com/in/tiasherringham/

• Elizabeth Jarvis-Shean on LinkedIn: https://www.linkedin.com/in/elizabeth-jarvis-shean-141a7966/

• Regina (Gina) Tarone on LinkedIn: https://www.linkedin.com/in/regina-tarone-a565a2/overlay/about-this-profile/

• My Journey (Part 1): I have a job that I would never be hired for: https://www.linkedin.com/posts/jessica-lachs_anniversary-datascience-finance-activity-7216912300056727553-mEv6/?utm_source=share&utm_medium=member_desktop

• Starting an Analytics Org From Scratch — Lessons From a Decade at DoorDash: https://review.firstround.com/starting-an-analytics-org-from-scratch-lessons-from-a-decade-at-doordash/

—

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.

Jeff Weinstein is a product lead at Stripe, where he helped grow their payment APIs to hundreds of billions in volume and transformed the way founders start companies into a few simple clicks with Atlas. Prior to Stripe, Jeff led several startups and sold companies to Groupon and Box. He’s known for his customer obsession, craft, quality, and building beloved products businesses rely on. In our conversation, we discuss:

• The power of customer obsession and how to operationalize it in the product development process

• How to pick the right metrics and use them to drive impact

• Techniques for getting things done at big companies

• A group practice Jeff started to uplevel product craft, called Study Group

• The story behind Stripe Atlas and its mission to increase entrepreneurship globally

• Lessons from working with the founders of Stripe

—

Brought to you by:

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

• Cycle—Your feedback hub, on autopilot

• Anvil—The fastest way to build software for documents

—

Find the transcript at: https://www.lennysnewsletter.com/p/creating-a-culture-of-excellence

—

Where to find Jeff Weinstein:

• X: https://x.com/jeff_weinstein

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

• Email: [email protected]

—

Where to find Lenny:

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

• X: https://twitter.com/lennysan

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

—

In this episode, we cover:

(00:00) Jeff’s background 

(10:16)  The “go, go, go ASAP + optimistic, long-term compounding” approach

(15:38) The importance of craft and quality

(24:15) Effective customer communication strategies

(28:57) The importance of speed in customer interactions 

(33:19) Narrowing your focus

(36:53) Why you should pay attention only to paying-customer feedback

(40:24) Practicing silence when communicating 

(45:33) The role of metrics in product success

(54:08) Empowering teams with a single metric

(58:23) Picking the right metric for your audience

(01:05:10) The importance of metric hygiene

(01:11:33) How Stripe uses “study groups” for product improvement

(01:37:20) Stripe’s Atlas: simplifying company formation

(01:50:38) Automation and operational efficiency

(01:55:13) Diversity and team building

(02:03:09) Building new products within a large company

(02:21:10) Lightning round

—

Referenced:

• Atlas: https://stripe.com/atlas

• Stripe: https://stripe.com/

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

• GitHub: https://github.com/

• Linear: https://linear.app/

• Figma: https://www.figma.com/

• Jeff’s tweet about Stripe’s bug-finder program: https://x.com/jeff_weinstein/status/1777487507934040300

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

• How we use friction logs to improve products at Stripe: https://dev.to/stripe/how-we-use-friction-logs-to-improve-products-at-stripe-i6p

• Fidelity: https://www.fidelity.com/

• 83(b) election: https://docs.stripe.com/atlas/83b-election

• Jeff’s tweet about Atlas’s NPS score: https://x.com/jeff_weinstein/status/1788644576330469638

• What is a Delaware corporation? Here’s what makes this state so attractive to businesses: https://stripe.com/resources/more/what-is-a-delaware-corporation

• Incorporating in Delaware explained: Why it’s such a popular option for businesses: https://stripe.com/resources/more/incorporating-in-delaware-explained

• 7 of Pixar’s Best Storyboard Examples and the Stories Behind Them: https://boords.com/blog/7-of-pixars-best-storyboard-examples-and-the-stories-behind-them

• Alex Kehayias on LinkedIn: https://www.linkedin.com/in/alexkehayias/

• Patrick McKenzie on LinkedIn: https://www.linkedin.com/in/patrickmckenzie/

• AngelList: https://www.angellist.com/

• Dan Hightower on LinkedIn: https://www.linkedin.com/in/danhighto/

• Stripe Atlas perks partners: https://support.stripe.com/questions/stripe-atlas-perks-partners

• 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

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

• Orbiting the Giant Hairball: A Corporate Fool’s Guide to Surviving with Grace: https://www.amazon.com/Orbiting-Giant-Hairball-Corporate-Surviving/dp/0670879835

• 7 Powers: The Foundations of Business Strategy: https://www.amazon.com/7-Powers-Foundations-Business-Strategy/dp/0998116319

• Business strategy with Hamilton Helmer (author of 7 Powers): https://www.lennysnewsletter.com/p/business-strategy-with-hamilton-helmer

• Box: https://www.box.com/

• Patrick Collison on X: https://x.com/patrickc

• How to with John Wilson on HBO: https://www.hbo.com/how-to-with-john-wilson

• The Quiet Girl on Hulu: https://www.hulu.com/movie/the-quiet-girl-b50a4b8e-d3ff-4635-b806-5e7dbd292ca4

• Raycast: https://www.raycast.com/

• Quicksilver: https://qsapp.com/

• Alfred: https://www.alfredapp.com/help/workflows/automations/

• CleanShot: https://cleanshot.com/

• John Collison on X: https://x.com/collision

—

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.

Mike Maples, Jr. is a legendary early-stage startup investor and a co-founder and partner at Floodgate. He’s made early bets on transformative companies like Twitter, Lyft, Twitch, Okta, Rappi, and Applied Intuition and is one of the pioneers of seed-stage investing as a category. He’s been on the Forbes Midas List eight times and enjoys sharing the lessons he’s learned from his years studying iconic companies. In his new book, Pattern Breakers: Why Some Start-Ups Change the Future, co-authored with Peter Ziebelman, he discusses what he’s found separates startups and founders that break through and change the world from those that don’t. After spending years reviewing the notes and decks from the thousands of startups he’s known over the past two decades, he’s uncovered three ways that breakthrough founders think and act differently. In our conversation, Mike talks about:

• The three elements of breakthrough startup ideas

• Why you need to both think and act differently

• How to avoid the “comparison trap” and “conformity trap”

• The importance of movements, storytelling, and healthy disagreeableness in startup success

• How to apply pattern-breaking principles within large companies

• Mike’s one piece of advice for founders

• Much more

Pre-order Mike’s book here and get a second signed copy for free. Limited copies are available, so order ASAP: patternbreakers.com/lenny.

—

Brought to you by:

• Enterpret—Transform customer feedback into product growth

• Anvil—The fastest way to build software for documents

• Webflow—The web experience platform

—

Find the transcript at: https://www.lennysnewsletter.com/p/how-to-find-a-great-startup-idea-mike-maples-jr

—

Where to find Mike Maples, Jr.:

• X: https://x.com/m2jr

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

• Substack: https://greatness.substack.com/

• Website: https://www.floodgate.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) Mike’s background

(03:10) The inspiration behind Pattern Breakers

(08:09) Uncovering startup insights

(11:37) A quick summary of Pattern Breakers

(13:52) Coming up with an idea

(15:30) Inflections

(17:09) Examples of inflections

(28:10) Insights

(36:58) The power of surprises

(47:36) Founder-future fit

(55:33) Advice for aspiring founders

(56:41) Living in the future: valid opinions

(55:34) Case study: Maddie Hall and Living Carbon

(58:40) Identifying lighthouse customers

(01:00:53) The importance of desperation in customer needs

(01:03:57) Creating movements and storytelling

(01:24:22) The role of disagreeableness in startups

(01:34:42) Applying these principles within a company

(01:40:43) Lightning round

—

Referenced:

• Pattern Breakers: Why Some Start-Ups Change the Future: https://www.amazon.com/Pattern-Breakers-Start-Ups-Change-Future/dp/1541704355

• Justin.tv: https://en.wikipedia.org/wiki/Justin.tv

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

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

• The Unconventional Exit: How Justin Kan Sold His First Startup on eBay: https://medium.datadriveninvestor.com/the-unconventional-exit-how-justin-kan-sold-his-first-startup-on-ebay-4d705afe1354

• Kyle Vogt on LinkedIn: https://www.linkedin.com/in/kylevogt/

• The State of Telehealth Before and After the COVID-19 Pandemic: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9035352/

• The Craigslist Killers: https://www.gq.com/story/craigslist-killers

• The social radar: Y Combinator’s secret weapon | Jessica Livingston (co-founder of Y Combinator, author, podcast host): https://www.lennysnewsletter.com/p/the-social-radar-jessica-livingston

• Michael Seibel on LinkedIn: https://www.linkedin.com/in/mwseibel/

• The Airbnb Story: How Three Ordinary Guys Disrupted an Industry, Made Billions ... and Created Plenty of Controversy: https://www.amazon.com/Airbnb-Story-Ordinary-Disrupted-Controversy/dp/0544952669

• Scott Cook: https://www.forbes.com/profile/scott-cook/

• Chegg: https://www.chegg.com/

• Aayush Phumbhra on LinkedIn: https://www.linkedin.com/in/aayush/

• Osman Rashid on LinkedIn: https://www.linkedin.com/in/osmanrashid/

• Okta: https://www.okta.com/

• The Man Who Makes the Future: Wired Icon Marc Andreessen: https://www.wired.com/2012/04/ff-andreessen/

• Peter Ludwig on LinkedIn: https://www.linkedin.com/in/peterwludwig/

• Qasar Younis on LinkedIn: https://www.linkedin.com/in/qasar/

• Paul Allen’s website: https://paulallen.com/

• Louis Pasteur quote: https://www.forbes.com/quotes/6145/

• What was Atrium and why did it fail? https://www.failory.com/cemetery/atrium

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

• Drew Houston on LinkedIn: https://www.linkedin.com/in/drewhouston/

• William Gibson’s quote: https://www.goodreads.com/quotes/681-the-future-is-already-here-it-s-just-not-evenly

• Maddie Hall on LinkedIn: https://www.linkedin.com/in/maddie-hall-76293135/

• Living Carbon: https://www.livingcarbon.com

• Zenefits (now Trinet): https://connect.trinet.com/

• Sam Altman on X: https://x.com/sama

• Steve Wozniak on LinkedIn: https://www.linkedin.com/in/wozniaksteve/

• Horsley Bridge Partners: https://www.horsleybridge.com/

• David Swensen: https://en.wikipedia.org/wiki/David_F._Swensen

• Judith Elsea on LinkedIn: https://www.linkedin.com/in/judithelsea/

• 7 Powers: The Foundations of Business Strategy: https://www.amazon.com/7-Powers-Foundations-Business-Strategy/dp/0998116319

• Business strategy with Hamilton Helmer (author of 7 Powers): https://www.lennysnewsletter.com/p/business-strategy-with-hamilton-helmer

• Lyft’s Focus on Community and the Story Behind the Pink Mustache: https://techcrunch.com/2012/09/17/lyfts-focus-on-community-and-the-story-behind-the-pink-mustache/

• Logan Green on LinkedIn: https://www.linkedin.com/in/logangreen/

• John Zimmer on LinkedIn: https://www.linkedin.com/in/johnzimmer11/

• Storytelling with Nancy Duarte: How to craft compelling presentations and tell a story that sticks: https://www.lennysnewsletter.com/p/storytelling-with-nancy-duarte-how

• Steve Jobs Introducing the iPhone at MacWorld 2007: https://www.youtube.com/watch?v=x7qPAY9JqE4

• Jonathan Livingston Seagull: https://www.amazon.com/Jonathan-Livingston-Seagull-Richard-Bach/dp/0743278909

• The paths to power: How to grow your influence and advance your career | Jeffrey Pfeffer (author of 7 Rules of Power, professor at Stanford GSB): https://www.lennysnewsletter.com/p/the-paths-to-power-jeffrey-pfeffer

• Robin Roberts on LinkedIn: https://www.linkedin.com/in/robin-roberts-393a934b/

• Skunkworks: https://www.lockheedmartin.com/en-us/who-we-are/business-areas/aeronautics/skunkworks.html

• 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

• Hard-won lessons building 0 to 1 inside Atlassian | Tanguy Crusson (Head of Jira Product Discovery): https://www.lennysnewsletter.com/p/building-0-to-1-inside-atlassian-tanguy-crusson

• Figma: https://www.figma.com/

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

• Vinod Khosla: https://www.khoslaventures.com/team/vinod-khosla/

• Top Five Regrets of the Dying: A Life Transformed by the Dearly Departing: https://www.amazon.com/Top-Five-Regrets-Dying-Transformed-ebook/dp/B07KNRLY1L

• Chase, Chance, and Creativity: The Lucky Art of Novelty: https://www.amazon.com/Chase-Chance-Creativity-Lucky-Novelty/dp/0262511355

• Clay Christensen’s books: https://www.amazon.com/stores/Clayton-M.-Christensen/author/B000APPD3Y

• Resonate: Present Visual Stories That Transform: https://www.amazon.com/Resonate-Present-Stories-Transform-Audiences/dp/0470632011

• Ferrari on Prime: https://www.amazon.com/Ferrari-Adam-Driver/dp/B0CNDBN672

• Montblanc fountain pens: https://www.montblanc.com/en-us

—

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.

Dylan Field is the co-founder and CEO of Figma, the collaborative design platform that has revolutionized how product teams work. In my first-ever live podcast, recorded at Figma Config, Dylan and I dig into:

• How intuition and product taste drive Dylan’s decision-making

• The challenge of keeping things simple

• Dylan’s thoughts on the future of product management

• Lessons from Figma’s early days

• How Figma built their initial user base

• Dylan’s journey from intern to CEO of a 1,000+-person company

• The future of design tools and AI

—

Brought to you by:

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

• Anvil—The fastest way to build software for documents

• User Testing—Human understanding. Human experiences.

—

Find the transcript at: https://www.lennysnewsletter.com/p/dylan-field-live-at-config

—

Where to find Dylan Field:

• X: https://x.com/zoink?lang=en

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

—

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

(01:11) Welcoming Dylan Field

(02:36) Highlights and surprises from Config

(06:58) The philosophy of design

(08:01) Raccoon feet and muffin hands

(09:57) Building and refining intuition and product taste

(12:50) How to influence leadership

(16:14) The role of product managers

(21:12) The future of product management

(22:20) The importance of simplicity in design

(26:10) The long road to Figma’s launch

(27:44) Advice for aspiring entrepreneurs

(29:07) Knowing when it’s time to ship

(30:39) Early user acquisition strategies

(35:50) Spotting trends and future innovations

(39:20) Reflections on leadership and growth

(43:16) Lightning round

—

Referenced:

• Mihika Kapoor on LinkedIn: https://www.linkedin.com/in/mihikakapoor/

• Rick Rubin on the Creative Act—60 Minutes: https://www.youtube.com/watch?v=sE1teB5bN-w

• Figma pages: https://help.figma.com/hc/en-us/articles/360038511293-Create-and-manage-pages

• Leading through uncertainty: A design-led company—Brian Chesky (Config 2023): https://www.youtube.com/watch?v=Dkfijg7s76o

• An inside look at how Figma builds product | Yuhki Yamashita (CPO of Figma): https://www.lennysnewsletter.com/p/an-inside-look-at-how-figma-builds

• 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

• An inside look at Figma’s unique GTM motion | Claire Butler (first GTM hire): https://www.lennysnewsletter.com/p/an-inside-look-at-figmas-unique-bottom

• Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO): https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building

• Nadia Singer on LinkedIn: https://www.linkedin.com/in/nadiasinger/

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

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

• Tim Van Damme on LinkedIn: https://www.linkedin.com/in/tim-van-damme-maxvoltar/

• Coda: https://coda.io/

• Shishir Mehrotra on LinkedIn: https://www.linkedin.com/in/shishirmehrotra/

• Websim: https://websim.ai/

• eToys.com commercial (from Dylan’s childhood acting career): https://www.youtube.com/watch?v=k3Y92aCmmbU

—

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.

Jessica Livingston is a co-founder of Y Combinator, the first and most successful startup accelerator. Y Combinator has funded over 5,000 companies, 200 of which are now unicorns, including Airbnb, Dropbox, DoorDash, Stripe, Coinbase, and Reddit. Jessica played a crucial role in YC’s early success, when she was nicknamed the “social radar” because of her uncanny ability to quickly evaluate people—an essential skill when investing in early-stage startups. She’s also the host of the popular podcast The Social Radars, where she interviews billion-dollar-startup founders, and the author of the acclaimed book Founders at Work, which captures the origin stories of some of today’s most interesting companies. In our conversation, we discuss:

• How Jessica gained the affectionate title of the “social radar”

• Why defensive founders are a red flag

• How to develop your social radar

• What she looks for in founders during YC interviews

• How YC’s early inexperience in angel investing led to the batch model

• Her favorite stories from interviews with Airbnb, Rippling, and more

• Lessons learned from hosting her own podcast

• Much more

—

Brought to you by:

• Enterpret—Transform customer feedback into product growth

• Anvil—The fastest way to build software for documents

• Vanta—Automate compliance. Simplify security

—

Find the transcript at: https://www.lennysnewsletter.com/p/the-social-radar-jessica-livingston

—

Where to find Jessica Livingston:

• X: https://x.com/jesslivingston

• LinkedIn: https://www.linkedin.com/in/jessicalivingston1/

• Podcast: https://www.thesocialradars.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) Jessica’s background

(02:42) Thoughts on being under-recognized

(07:52) Jessica’s superpower: the social radar

(15:11) Evaluating founders: key traits and red flags

(21:00) The Airbnb story: a lesson in hustle and determination

(25:57) A YC success story

(28:26) The importance of earnestness

(32:45) Confidence vs. defensiveness

(34:43) Commitment and co-founder disputes

(37:46) Relentless resourcefulness

(40:00) Jessica’s social radar: origins and insights

(43:24) Honing her social radar skills

(45:44) Conviction and scams: a Y Combinator story

(46:50) The interview process: challenges and insights

(48:20) Operationalizing founder evaluation

(49:38) Advice for building social radar skills

(52:08) The “Reading the Mind in the Eyes” quiz

(55:19) Jessica’s podcast: The Social Radars

(01:00:34) Lessons from podcasting and interviewing

(01:09:58) Lightning round

—

Referenced:

• Paul Graham’s post about Jessica: https://paulgraham.com/jessica.html

• Paul Graham on X: https://x.com/paulg

• Robert Tappan Morris: https://en.wikipedia.org/wiki/Robert_Tappan_Morris

• Trevor Blackwell on X: https://x.com/tlbtlbtlb

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

• “The Founders” examines the rise and legend of PayPal: https://www.economist.com/culture/2022/02/19/the-founders-examines-the-rise-and-legend-of-paypal

• Patrick Collison on X: https://x.com/patrickc

• John Collison on X: https://x.com/collision

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

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

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

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

• Parker Conrad on LinkedIn: https://www.linkedin.com/in/parkerconrad/

• Zenefits: https://connect.trinet.com/hr-platform

• Goat: https://www.goat.com/

• Eddy Lu on LinkedIn: https://www.linkedin.com/in/eddylu/

• Drew Houston on LinkedIn: https://www.linkedin.com/in/drewhouston/

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

• 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

•Bitcoin launderer pleads guilty, admits to massive Bitfinex hack: https://www.cnbc.com/2023/08/03/new-york-man-admits-being-original-bitfinex-hacker-during-guilty-plea-in-dc-to-bitcoin-money-laundering.html

• Paul Graham’s tweet with the facial recognition test: https://x.com/paulg/status/1782875262855663691

• SmartLess podcast: https://www.smartless.com

• Jason Bateman on X: https://x.com/batemanjason

• Will Arnett on X: https://x.com/arnettwill

• Sean Hayes on X: https://x.com/seanhayes

• The Social Radars with Tony Xu, Co-Founder & CEO of DoorDash: https://www.ycombinator.com/library/Ja-tony-xu-co-founder-ceo-of-doordash

• The Social Radars with Brian Chesky: https://www.ycombinator.com/library/JW-brian-chesky-co-founder-ceo-of-airbnb

• The Social Radars with Patrick and John Collison: https://www.ycombinator.com/library/Kx-patrick-john-collison-co-founders-of-stripe

• The Social Radars with Brian Armstrong: https://www.ycombinator.com/library/K3-brian-armstrong-co-founder-and-ceo-of-coinbase

• The Social Radars with Emmett Shear: https://www.ycombinator.com/library/KM-emmett-shear-co-founder-of-twitch

• The Social Radars with Paul Graham: https://www.ycombinator.com/library/JV-paul-graham-co-founder-of-y-combinator-and-viaweb

• The Social Radars with Adora Cheung: https://www.ycombinator.com/library/L0-adora-cheung-co-founder-of-homejoy-instalab

• Founders at Work: Stories of Startups’ Early Days: https://www.amazon.com/Founders-Work-Stories-Startups-Early/dp/1430210788

• Startup School: https://www.startupschool.org/

• The Social Radars with Parker Conrad: https://www.ycombinator.com/library/Ky-parker-conrad-founder-of-zenefits-rippling

• Rippling: https://www.rippling.com/

• Carry on, Jeeves: https://www.amazon.com/Carry-Jeeves-Dover-Thrift-Editions/dp/0486848957

• Very Good, Jeeves: https://www.amazon.com/Very-Good-Jeeves-Wooster-Book-ebook/dp/B0051GST06

• Right Ho, Jeeves: https://www.amazon.com/Right-Ho-Jeeves-P-Wodehouse-ebook/dp/B083FFDNHN/

• Life: https://www.amazon.com/Life-Keith-Richards-ebook/dp/B003UBTX72/

• My Name Is Barbra: https://www.amazon.com/My-Name-Barbra-Streisand/dp/0525429522

• Clarkson’s Farm on Prime: https://www.amazon.com/Clarksons-Farm-Season-1/dp/B095RHJ52R

• Schitt’s Creek on Hulu: https://www.hulu.com/series/schitts-creek-a2e7a946-9652-48a8-884b-3ea7ea4de273

• Yellowstone on Peacock: https://www.peacocktv.com/stream-tv/yellowstone

• Sam Altman on X: https://x.com/sama

• Justin Kan on LinkedIn: https://www.linkedin.com/in/justinkan/

• Alexis Ohanian on X: https://x.com/alexisohanian

• Steve Huffman on LinkedIn: https://www.linkedin.com/in/shuffman56/

• Breaking News: Condé Nast/Wired Acquires Reddit: https://techcrunch.com/2006/10/31/breaking-news-conde-nastwired-acquires-reddit/

• Charles River Venture: https://www.crv.com/

—

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

—

Lenny may be an investor in the companies discussed.

Ami Vora is the Chief Product Officer of Faire, which connects independent retailers and brands around the world. Before Faire, Ami spent over 15 years at Meta, including as VP of Product and Design for WhatsApp (2B+ users), VP of Product for Facebook’s ads system (now $130B of annual revenue), and director at Instagram. She began her career working on developer tools at Microsoft. In our conversation, we discuss:

• Why execution eats strategy for breakfast

• Using metaphor to rally teams around one shared goal

• How to build cross-functional relationships

• “Dinosaur brain,” “Toddler soccer,” and the “hill climbing” metaphors

• A tactic for handling disagreement

• Tips for working well with product-minded founders as a product leader

• The story of Ami’s incredible 15-year journey from temp to VP at Meta

• Much more

—

Brought to you by:

• Sidebar—Accelerate your career by surrounding yourself with extraordinary peers.

• Anvil—The fastest way to build software for documents.

• User Testing—Human understanding. Human experiences.

—

Find the transcript at: https://www.lennysnewsletter.com/p/authenticity-and-curiosity-ami-vora

—

Where to find Ami Vora:

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

• Substack: https://amivora.substack.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) Ami’s background

(02:00) The myth of perfection in success

(07:55) Emotionally connecting with the job

(09:55) Embracing curiosity in moments of challenge

(13:16) Thinking in feedback loops

(17:17) The “dinosaur brain” metaphor in product reviews

(20:20) Strategies for conducting effective product reviews

(26:33) Using metaphors and imagery to communicate your vision

(29:35) The power of having a shared narrative

(31:55) WhatsApp: an example of metaphor in action

(34:44) Emulating people that inspire you

(36:19) WhatsApp video calling

(37:35) Why execution is greater than strategy

(41:36) Time allotment for strategy vs. execution

(45:10) How to become a better strategic thinker

(47:59) The intricacies of implementing feedback

(51:53) Being a female leader in tech

(55:13) Advice for young women in tech

(56:07) Setting goals and aligning incentives

(01:01:40) Acknowledging hard truths

(01:05:46) Lessons from transitioning to Faire

(01:08:40) The importance of a good CPO/CEO relationship

(01:11:17) Vetting heads of product and maintaining customer focus

(01:12:40) How Ami went from intern to leading major products at Meta

(01:14:53) The one thing you should do to be successful in product

(01:17:25) Lightning round

—

Referenced:

• Faire: https://www.faire.com/

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

•  Community Wisdom: AMA with Dan Hockenmaier + Facilitating a roadmap session, structuring product teams, navigating an acquisition, companies not needing PMs anymore, and much more: https://www.lennysnewsletter.com/p/making-meta-andrew-boz-bosworth-cto

• Developing a growth model + marketplace growth strategy | Dan Hockenmaier (Faire, Thumbtack, Reforge): https://www.lennysnewsletter.com/p/developing-a-growth-model-marketplace

• Dan Hockenmaier’s website: https://www.danhock.com/

• On Reviews: https://boz.com/articles/reviews

• Finding a global optimum always feels like a hill climb: https://www.linkedin.com/posts/amvora_finding-a-global-optimum-always-feels-like-activity-7074776143882588161-jhyy/

• Dolores Park: https://sfrecpark.org/892/Mission-Dolores-Park

• Rob Goldman on LinkedIn: https://www.linkedin.com/in/robgoldman/

• Execution eats strategy for breakfast, but execution without strategy leads to burnout: https://rationalpm.substack.com/p/execution-eats-strategy-for-breakfast

• The goal of a “strategy” is to change our own team’s behavior: https://amivora.substack.com/p/the-goal-of-a-strategy-is-to-change

• The paths to power: How to grow your influence and advance your career | Jeffrey Pfeffer (author of 7 Rules of Power, professor at Stanford GSB): https://www.lennysnewsletter.com/p/the-paths-to-power-jeffrey-pfeffer

• Path to Power course outline: https://jeffreypfeffer.com/wp-content/uploads/2019/10/Pfeffer-OB377-Course-Outline-2018.pdf

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

• Max Rhodes on LinkedIn: https://www.linkedin.com/in/max-rhodes/

• Coupa Coffee: https://www.coupacafe.com/

• Brandee Barker on LinkedIn: https://www.linkedin.com/in/brandeedbarker/

• Year of Yes: How to Dance It Out, Stand In the Sun and Be Your Own Person: https://www.amazon.com/Year-Yes-Dance-Stand-Person/dp/1476777128 

• How to tell better stories | Matthew Dicks (Storyworthy): https://www.lennyspodcast.com/how-to-tell-better-stories-matthew-dicks-storyworthy/

• A life of yes: Matthew Dicks at TEDxSomerville: https://www.youtube.com/watch?v=F3TaQFcaMk4

• The Office on Peacock: https://www.peacocktv.com/stream-tv/the-office

• 30 Rock on Peacock: https://www.peacocktv.com/watch-online/tv/30-rock/6240863759978157112

• Dall-E-2: https://openai.com/index/dall-e-2/

• ChatGPT: https://chatgpt.com

• Fellow kettles: https://fellowproducts.com/products/stagg-ekg-electric-pour-over-kettle

• TikTok’s “Roman Empire” Meme, Explained: https://www.forbes.com/sites/danidiplacido/2023/09/21/tiktoks-roman-empire-meme-explained/

—

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.

Tanguy Crusson is the product lead for Jira Product Discovery at Atlassian. In his more than 10 years at the company, he has been instrumental in taking several new products from zero to one, including HipChat, Statuspage, and Jira Product Discovery. In this episode, we dive deep into the struggles of innovating and building new products inside a large company. Tanguy shares candid stories about what worked, what didn’t, and his many hard-won lessons learned about how to successfully build 0 to 1. We cover:

• Why large companies with so many advantages still fail at creating new products

• Lessons learned from building HipChat

• How to avoid common pitfalls like competitive myopia and premature scaling

• Lessons learned from the acquisition and integration of Statuspage

• Insights from the success of Jira Product Discovery

• Tactics for protecting your “ugly babies”

• The power of “lighthouse users”

• The importance of having a “why now”

• Much more

—

Brought to you by:

• Vanta—Automate compliance. Simplify security

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

• Coda—The all-in-one collaborative workspace

—

Find the transcript at: https://www.lennysnewsletter.com/p/building-0-to-1-inside-atlassian-tanguy-crusson

—

Where to find Tanguy Crusson:

• X: https://x.com/tanguycrusson

• LinkedIn: https://www.linkedin.com/in/tanguy-crusson-99832a

—

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) Tanguy’s background

(02:30) Tanguy’s journey at Atlassian

(07:03) The challenges of innovating in large companies

(10:42) Atlassian's high bar for excellence 

(12:58) The HipChat story: successes, failures, and lessons learned

(20:47) Lessons learned from building HipChat

(33:49) Statuspage: a journey of perseverance

(39:48) Acquisition challenges and lessons

(47:22) Strategic decisions: build, buy, or partner?

(48:17) Learning to articulate "why now"

(54:08) A quick summary of lessons in this episode

(55:40) The success and pain of launching Jira Product Discovery 

(58:10) Incubating new products: the Point A program

(01:00:13) Failure is the most likely outcome

(01:04:15) Atlassian's four-phase approach to launching new products

(01:09:20) Breaking rules without breaking trust

(01:16:16) Early success and team autonomy

(01:17:22) Innovating without disrupting existing customers

(01:23:17) The Lighthouse Users program

(01:30:00) Protecting and nurturing new ideas

(01:36:14) Balancing innovation with personal well-being

(01:38:17) A reminder to look after yourself

(01:42:06) Lightning round

—

Referenced:

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

• HipChat: https://community.atlassian.com/t5/Hipchat/ct-p/hipchat

• Stride: https://community.atlassian.com/t5/Stride/ct-p/stride

• Statuspage: https://www.atlassian.com/software/statuspage

• Opsgenie: https://www.atlassian.com/software/opsgenie

• Jira Product Discovery: https://www.atlassian.com/software/jira/product-discovery

• HipChat billboard: https://x.com/HubSpot/status/654696998126272512

• Announcing our new partnership with Slack: https://www.atlassian.com/blog/announcements/new-atlassian-slack-partnership

• Slack shows it’s worried about Microsoft Teams with a full-page newspaper ad: https://www.theverge.com/2016/11/2/13497766/slack-microsoft-teams-new-york-times-ad

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

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

• Confluence: https://www.atlassian.com/software/confluence

• PagerDuty: https://www.pagerduty.com/

• New Relic: https://newrelic.com/

• BigPanda: https://www.bigpanda.io/

• Transparent Uptime: http://www.transparentuptime.com/

• 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

• Figma: https://www.figma.com/

• Lessons from Atlassian: Launching new products, getting buy-in, and staying ahead of the competition | Megan Cook (head of product, Jira): https://www.lennysnewsletter.com/p/lessons-from-atlassian-launching

• Noah Weiss on LinkedIn: https://www.linkedin.com/in/noahw/

• Tanguy’s LinkedIn post about “lighthouse users”: https://www.linkedin.com/posts/tanguy-crusson-99832a_lighthouse-users-one-of-the-pm-techniques-activity-7176654510801502210-hWNi/

• Pixar Chief: Protect Your ‘Ugly Babies’ (Your Unsightly Ideas): https://www.forbes.com/sites/andyboynton/2014/03/17/pixar-chief-protect-your-ugly-babies-your-unsightly-ideas/

• Atlas: https://www.atlassian.com/software/atlas

• Point A: https://www.atlassian.com/point-a

• Scott Farquhar on LinkedIn: https://www.linkedin.com/in/scottfarquhar

• Who: A Method for Hiring: https://www.amazon.com/Who-Method-Hiring-HC-2008/dp/B004C79SRS/

• Hakim’s Odyssey: Book 1: From Syria to Turkey: https://www.amazon.com/Hakims-Odyssey-Book-Syria-Turkey/dp/1637790007

• Living with the Earth, Volume 1: Permaculture, Ecoculture: Inspired by Nature: https://www.amazon.com/Living-Earth-Gardeners-Permaculture-Ecoculture/dp/1856232603/

• INRIA: https://en.wikipedia.org/wiki/French_Institute_for_Research_in_Computer_Science_and_Automation

• How a Hydrofoil Works: https://web.mit.edu/2.972/www/reports/hydrofoil/hydrofoil.html

• What Is Kitefoil or Foilboarding?: https://www.whenitswindy.com/wp/?page_id=534

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

• Tanguy’s freediving stats: https://www.aidainternational.org/Athletes/Profile-00000000-0000-0000-0000-000000000a45

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

—

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

—

Lenny may be an investor in the companies discussed.

Jeffrey Pfeffer teaches the single most popular (and somewhat controversial) class at Stanford’s Graduate School of Business: The Paths to Power. He’s also the author of 16 books, including 7 Rules of Power: Surprising—But True—Advice on How to Get Things Done and Advance Your Career. He has taught at Harvard, the London Business School, and IESE and has written for publications like Fortune and the Washington Post. Recognized by the Academy of Management and listed in the Thinkers50 Hall of Fame, Jeffrey also serves on several corporate and nonprofit boards, bringing his expertise to global audiences through seminars and executive education. In our conversation, we discuss:

• Jeffrey’s seven rules of power

• How individuals can acquire and use power in business

• Networking, and how to do it effectively

• How to build a non-cringe personal brand

• How to increase your influence to amplify your impact

• Examples and stories of people building power

• Tradeoffs and challenges that come with power

—

Brought to you by:

• Uizard—AI-powered prototyping for visionary product leaders

• Webflow—The web experience platform

• Heap—Cross-platform product analytics that converts, engages, and retains customers

—

Find the transcript at: https://www.lennysnewsletter.com/p/the-paths-to-power-jeffrey-pfeffer

—

Where to find Jeffrey Pfeffer:

• X: https://x.com/JeffreyPfeffer

• LinkedIn: https://www.linkedin.com/in/jeffrey-pfeffer-57a01b6/

• Website: https://jeffreypfeffer.com/

• Podcast: https://jeffreypfeffer.com/pfeffer-on-power/

—

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) Jeffrey’s background 

(02:54) Understanding discomfort with power

(04:56) Power skills for underrepresented groups

(07:51) The popularity and challenges of Jeffrey’s class at Stanford

(12:21) The seven rules of power

(13:03) Success stories from his course

(15:43) Building a personal brand

(21:11) Getting out of your own way

(26:04) Breaking the rules to gain power

(30:34) Networking relentlessly

(40:10) Why Jeffrey says to “pursue weak ties”

(42:00) Using your power to build more power

(44:34) The importance of appearance and body language

(47:15) Mastering the art of presentation

(55:12) Examples of homework assignments that Jeffrey gives students

(59:11) People will forget how you acquired power

(01:03:58) More good people need to have power

(01:10:49) The price of power and autonomy

(01:17:13) A homework assignment for you

—

Referenced:

• Gerald Ferris on LinkedIn: https://www.linkedin.com/in/gerald-r-ferris-5816b1b5/

• Political Skill at Work: https://tarjomefa.com/wp-content/uploads/2015/10/4173-engilish.pdf

• Laura Esserman, MD: https://cancer.ucsf.edu/people/esserman.laura

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

• Matthew 7: https://www.biblegateway.com/passage/?search=Matthew%207&version=NIV

• Mother Teresa quote: https://www.goodreads.com/quotes/2887-if-you-judge-people-you-have-no-time-to-love

• Paths to Power course description: https://jeffreypfeffer.com/wp-content/uploads/2019/10/Pfeffer-OB377-Course-Outline-2018.pdf

• 7 Rules of Power: https://jeffreypfeffer.com/books/7-rules-of-power/

• The Knowing-Doing Gap: https://jeffreypfeffer.com/books/the-knowing-doing-gap/

• Derek Kan on LinkedIn: https://www.linkedin.com/in/derekkan/

• Mitt Romney on X: https://x.com/mittromney

• Elaine Chao’s website: https://www.elainechao.com/

• Tony Hsieh: https://en.wikipedia.org/wiki/Tony_Hsieh

• Zappos: https://www.zappos.com/

• How I Did It: Zappos’s CEO on Going to Extremes for Customers: https://hbr.org/2010/07/how-i-did-it-zapposs-ceo-on-going-to-extremes-for-customers

• McKinsey & Company: https://www.mckinsey.com/

• Bain & Company: https://www.bain.com/

• BCG: https://www.bcg.com/

• Keith Ferrazzi’s website: https://www.keithferrazzi.com/

• Deloitte: https://www2.deloitte.com/

• Tristan Walker: https://www.linkedin.com/in/tristanwalker/

• Foursquare: https://foursquare.com/

• Laura Chau on LinkedIn: https://www.linkedin.com/in/laura-chau/

• Canaan Partners: https://www.canaan.com/

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

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

• Greylock: https://greylock.com/

• The Women Who Venture (WoVen) Podcast: https://www.canaan.com/woven/podcasts

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

• Gary Loveman and Harrah’s Entertainment: https://www.gsb.stanford.edu/faculty-research/case-studies/gary-loveman-harrahs-entertainment

• “If you need help, just ask”: Underestimating compliance with direct requests for help: https://www.gsb.stanford.edu/faculty-research/publications/if-you-need-help-just-ask-underestimating-compliance-direct-requests

• Life story of Kathleen Frances Fowler: https://www.forevermissed.com/kathleenfowler/lifestory

• Jason Calacanis on LinkedIn: https://www.linkedin.com/in/jasoncalacanis/

• Jason Calacanis: A Case Study in Creating Resources: https://www.gsb.stanford.edu/faculty-research/case-studies/jason-calacanis-case-study-creating-resources

• You’re Invited: The Art and Science of Connection, Trust, and Belonging: https://www.amazon.com/Youre-Invited-Science-Cultivating-Influence/dp/0063030977

• View from the Top: https://www.gsb.stanford.edu/experience/learning/guest-speakers/view-top

• Omid Kordestani on LinkedIn: https://www.linkedin.com/in/omid-kordestani-46515151/

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

•  Esther Wojcicki on LinkedIn:  https://www.linkedin.com/in/estherwojcicki/

• Leanne Williams: https://med.stanford.edu/profiles/leanne-williams

• Precision Psychiatry: Using Neuroscience Insights to Inform Personally Tailored, Measurement-Based Care: https://www.amazon.com/Precision-Psychiatry-Neuroscience-Personally-Measurement-Based/dp/1615371583

• Mark Granovetter on LinkedIn: https://www.linkedin.com/in/mark-granovetter-8161704/

• The Strength of Weak Ties: https://snap.stanford.edu/class/cs224w-readings/granovetter73weakties.pdf

• Getting a Job: https://www.amazon.com/Getting-Job-Study-Contacts-Careers/dp/0226305813

• Acting with Power: https://www.amazon.com/Acting-Power-More-Powerful-Believe/dp/110190397X

• Articles by Herminia Ibarra: https://herminiaibarra.com/articles/

• Kingdom of the Planet of the Ape: https://www.imdb.com/title/tt11389872/

• Jim Collins’s website: https://www.jimcollins.com/

• Dana Carney on LinkedIn: https://www.linkedin.com/in/danarosecarney/

• Baba Shiv: https://www.gsb.stanford.edu/faculty-research/faculty/baba-shiv

• Tony Hayward: https://en.wikipedia.org/wiki/Tony_Hayward

• Lloyd Blankfein: https://en.wikipedia.org/wiki/Lloyd_Blankfein

• Regis McKenna: https://en.wikipedia.org/wiki/Regis_McKenna

• Jack Valenti: https://en.wikipedia.org/wiki/Jack_Valenti

• Salman Rushdie quote: https://www.pinterest.com/pin/434175220328596286/

• How to build deeper, more robust relationships | Carole Robin (Stanford GSB professor, “Touchy Feely”): https://www.lennysnewsletter.com/p/build-robust-relationships-carole-robin

• Carole Robin’s 15% rule: https://pen-name.notion.site/Carole-Robin-on-Lenny-s-Podcast-dc7159208e4242428f4b11ebc92285eb

• Karlie Kloss on Instagram: https://www.instagram.com/karliekloss

• Lindsey Graham’s website: https://www.lindseygraham.com/

• Was Microsoft’s Empire Built on Stolen Code? We May Never Know: https://www.wired.com/2012/08/ms-dos-examined-for-thef/

• Who’s who of Jeffrey Epstein’s powerful friends, associates and possible co-conspirators: https://www.cnn.com/2019/08/12/us/jeffrey-epstein-associates-possible-accomplices/index.html

• Why Did Martha Stewart Go to Prison? A Look Back at Her 2004 Fraud Case: https://people.com/martha-stewart-fraud-case-prison-sentence-look-back-8550277

• Dianne Feinstein: https://www.congress.gov/member/dianne-feinstein/F000062

• Richard Blum: https://en.wikipedia.org/wiki/Richard_C._Blum

• Athena Care Network: https://www.athenacarenetwork.org

• James G. March: https://en.wikipedia.org/wiki/James_G._March

• Satya Nadella on LinkedIn: https://www.linkedin.com/in/satyanadella/

• Trump Organization fined $1.6 million for tax fraud: https://apnews.com/article/politics-legal-proceedings-new-york-city-donald-trump-manhattan-e2f1d01525dafb64be8738c8b4f32085

• Rudy Giuliani: https://en.wikipedia.org/wiki/Rudy_Giuliani

• Harvard president resigns amid claims of plagiarism and antisemitism backlash: https://www.theguardian.com/education/2024/jan/02/harvard-president-claudine-gay-resigns

• Stanford president resigns after fallout from falsified data in his research: https://www.npr.org/2023/07/19/1188828810/stanford-university-president-resigns

• Rudy Crew: https://en.wikipedia.org/wiki/Rudy_Crew

—

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 the co-founder of Waze, the world’s largest community-based traffic and navigation app, acquired by Google for over $1 billion. He’s also founded nine other companies, been on the board of 20 companies, and advised more than 50 companies. He’s most recently the author of Fall in Love with the Problem, Not the Solution: A Handbook for Entrepreneurs, hailed by Steve Wozniak as the “Bible for entrepreneurs.” Uri is dedicated to creating impactful startups that solve real-world problems and has seen everything from failure to moderate success to big success. In our conversation, we dig into:

• Why falling in love with the problem is key to startup success

• The phases of the startup journey and how to navigate them

• Why firing is more important than hiring

• How Waze iterated to achieve product-market fit

• Tactics for telling a compelling story when fundraising

• Much more

—

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—

Find the transcript at: https://www.lennysnewsletter.com/p/lessons-from-uri-levine

—

Where to find Uri Levine:

• X: https://twitter.com/urilevine1

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

• Website: https://urilevine.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) Uri’s background

(02:50) Falling in love with the problem

(09:03) Signs this is a big enough problem

(10:54) The importance of passion

(12:06) A pivot example

(14:01) Where to find startup ideas

(21:57) Finding product-market fit at Waze

(29:45) The different phases of a startup journey

(36:47) What investors don’t want to hear

(39:53) Fundraising tips

(48:02) How to make your presentations stronger

(50:32) A wild fundraising story

(53:46) Firing and hiring

(59:50) The 30-day test

(01:04:12) Understanding users

(01:12:10) Talking to the right users

(01:15:36) Lightning round

—

Referenced:

• Fall in Love with the Problem, Not the Solution: A Handbook for Entrepreneurs: https://www.amazon.com/Fall-Love-Problem-Solution-Entrepreneurs/dp/1637741987

• Waze: https://www.waze.com/

• Ben Horowitz on LinkedIn: https://www.linkedin.com/in/behorowitz/

• Ben Horowitz quote: https://quotefancy.com/quote/1635284/Ben-Horowitz-As-a-startup-CEO-I-slept-like-a-baby-I-woke-up-every-2-hours-and-cried

• Michael Jordan quote: https://www.forbes.com/quotes/11194/#:~:text=I've%20lost%20almost%20300,that%20is%20why%20I%20succeed.

• Steph Curry: https://en.wikipedia.org/wiki/Stephen_Curry

• How Airbnb Used Word of Mouth to Change the Travel Industry Forever: https://truested.com/story/airbnb

• Space Mountain: https://en.wikipedia.org/wiki/Space_Mountain_(Disneyland)

• How Netflix builds a culture of excellence | Elizabeth Stone (CTO): https://www.lennysnewsletter.com/p/how-netflix-builds-a-culture-of-excellence

• Steve Wozniak on LinkedIn: https://www.linkedin.com/in/wozniaksteve/

• Uri’s post about the conference in Guatemala with Steve Wozniak: https://www.linkedin.com/posts/uri-levine_jewishnewyear-speakers-book-activity-6980089544079486976-0ADa/

• Leonardo da Vinci quote: https://www.goodreads.com/quotes/9010638-simplicity-is-the-ultimate-sophistication-when-once-you-have-tasted

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

• Nana Korobi Ya Oki: https://ikigaitribe.com/vlog/nana-korobi-ya-oki/

• That Will Never Work: The Birth of Netflix and the Amazing Life of an Idea: https://www.amazon.com/That-Will-Never-Work-Netflix/dp/0316530204

• Atomic Habits: An Easy & Proven Way to Build Good Habits & Break Bad Ones: https://www.amazon.com/Atomic-Habits-Proven-Build-Break/dp/0735211299

• 8 Great Chess Apps for Beginners and Grand Masters: https://www.wired.com/story/best-chess-apps/

• Pontera: https://pontera.com/

—

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

—

Lenny may be an investor in the companies discussed.

Cameron Adams is the co-founder and chief product officer of Canva. Canva is one of the world’s most valuable private software companies, used by 95% of Fortune 500 companies. Since its launch in 2013, Canva has grown to over 150 million monthly users in more than 190 countries, generating $2.3 billion in annual revenue. Prior to Canva, Cameron ran a design consultancy, worked at Google on Google Wave, and founded the email startup Fluent. He is also an author of five web design books and a regular speaker at global conferences. In our conversation, we discuss:

• Why they spent a year building their minimum viable product (MVP) before launch

• Why Canva has no managers, and their unique approach to coaching and performance reviews

• Why they encourage employees to “give away their Legos”

• Insights into Canva’s SEO growth strategy

• Their three-pillar framework for integrating AI into their product

• Stories from the early days

—

Brought to you by:

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—

Find the transcript at: https://www.lennysnewsletter.com/p/inside-canva-with-cameron-adams

—

Where to find Cameron Adams:

• X: https://twitter.com/themaninblue

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

• Website: https://themaninblue.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) Cameron’s background

(02:00) Reflecting on the success of Canva

(04:50) Reflecting on hard times

(10:01) Canva’s product-obsessed culture

(12:02) Why they prioritize internal promotions and hires

(13:56) What makes Canva unique

(16:31) The concept of giving away your Legos

(21:44) Why Canva has no managers

(24:29) Product management at Canva

(27:56) Reflections on working with a married couple

(30:37) Why they spent a year building their MVP before launch

(33:49) Advice for building an MVP

(41:23) Canva’s onboarding transformation

(44:25) Canva’s SEO strategy

(50:37) The success of Canva’s freemium strategy

(54:24) Integrating AI into Canva’s product

(01:01:50) Where to find Cameron

—

Referenced:

• Canva: https://www.canva.com/

• Melanie Perkins on LinkedIn: https://www.linkedin.com/in/melanieperkins

• Cliff Obrecht on LinkedIn: https://www.linkedin.com/in/cliff-obrecht-79ba9920

• Jennie Rogerson, Head of People, LinkedIn post about “season opener” events: https://www.linkedin.com/posts/jennierogerson_season-opener-is-one-of-my-favourite-events-activity-7006815614556135424-73bD/

• Game of Thrones on HBO: https://www.hbo.com/game-of-thrones

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

• ‘Give Away Your Legos’ and Other Commandments for Scaling Startups: https://review.firstround.com/give-away-your-legos-and-other-commandments-for-scaling-startups/

• Minimum viable product (MVP): https://www.productboard.com/glossary/minimum-viable-product-mvp

• Canva’s SEO Strategy Is Elite: https://thegrowthplaybook.substack.com/p/canvas-seo-strategy-is-elite

• The SEO Strategy That Led Canva to a $40 Billion Valuation: https://www.youtube.com/watch?v=INyGKt6LAqM

• Andrianes Pinantoan on LinkedIn: https://www.linkedin.com/in/andrianes/

• Canva Create: https://www.canva.com/canva-create/

—

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

—

Lenny may be an investor in the companies discussed.

Matt Dixon is one of the world’s foremost experts in sales and the author of The Challenger Sale, which sold over a million copies worldwide and was a #1 Amazon and Wall Street Journal bestseller. His most recent book, The JOLT Effect, focuses on overcoming customer indecision—one of the biggest challenges to closing deals. Outside of writing, Matt co-founded DCM Insights, a boutique consultancy helping organizations understand customer behavior, and is a frequent contributor to the Harvard Business Review, with more than 20 print and online articles to his credit. In our conversation, we discuss:

• Why 40% to 60% of qualified sales opportunities are lost due to customer indecision

• Why dialing up FOMO doesn’t work, and what to do instead

• The “pings and echoes” technique to catch issues early

• The JOLT method for overcoming indecision

• Key lessons from The Challenger Sale

• Practical examples of how to apply these principles to close more deals

—

Brought to you by:

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• Webflow—The web experience platform

• Heap—Cross-platform product analytics that converts, engages, and retains customers

—

Find the transcript at: https://www.lennysnewsletter.com/p/close-more-deals-matt-dixon

—

Where to find Matt Dixon:

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

• Website: https://www.jolteffect.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) Matt’s background

(01:57) The research behind Matt’s books

(06:08) Insights from The JOLT Effect

(10:15) FOMO vs. FOMU

(18:18) An example of selling software

(26:04) The JOLT method Step 1: Judge their level of indecision

(29:41) The “pings and echoes” technique

(34:49) Step 2: Offer a recommendation

(38:36) Step 3: Limit the exploration

(41:43) Step 4: Take risk off the table

(45:58) When to hit the pause button with a customer

(47:27) Insights from The Challenger Sale

(49:07) An example of a challenger sale

(55:23) Where to find Matt

—

Referenced:

• 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

• The Challenger Sale: Taking Control of the Customer Conversation: https://www.amazon.com/Challenger-Sale-Control-Customer-Conversation/dp/0670922854

• The JOLT Effect: How High Performers Overcome Customer Indecision: https://www.amazon.com/JOLT-Effect-Performers-Overcome-Indecision/dp/0593538102

• Gartner acquires CEB: https://www.gartner.com/en/about/acquisitions/history/ceb-acquisition

• Tiger King on Netflix: https://www.netflix.com/title/81115994

• Why sourdough went viral: https://www.economist.com/1843/2020/08/04/why-sourdough-went-viral

• Neil Rackham: https://en.wikipedia.org/wiki/Neil_Rackham

• Status quo bias in decision-making: https://en.wikipedia.org/wiki/Status_quo_bias

• Omission bias: https://thedecisionlab.com/biases/omission-bias

• Gartner Magic Quadrant & Critical Capabilities: https://www.gartner.com/en/research/magic-quadrant

• Dunning-Kruger effect: https://en.wikipedia.org/wiki/Dunning%E2%80%93Kruger_effect

• Stop Losing Sales to Customer Indecision: https://hbr.org/2022/06/stop-losing-sales-to-customer-indecision

• Dentsply Sirona: https://www.dentsplysirona.com/

• “We happy?” Briefcase scene from Tarantino’s Pulp Fiction: https://www.youtube.com/watch?v=FGchDuOpbhE

• Nupro Freedom Cordless Prophy System: https://www.dentsplysirona.com/en-us/discover/discover-by-category/preventive/hygiene-handpieces.html

—

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.

Bangaly Kaba was an early growth PM at Facebook, head of growth at Instagram, and VP of Product at Instacart and is currently Director of Product at YouTube overseeing a global team working on creator monetization. Bangaly has also been a growth advisor to dozens of companies, including Twitter, on the board of multiple companies, and is an active angel investor. In our conversation, we discuss:

• A simple framework for choosing where to work and what to work on

• The importance of “understand work”

• The “adjacent users” theory and how it can help you drive growth

• Advice for coaching product managers

• Invaluable lessons from his time at Instagram, Facebook, and YouTube

• Much more

—

Brought to you by:

• Uizard—AI-powered prototyping for visionary product leaders

• Mercury—The powerful and intuitive way for ambitious companies to bank

• Vanta—Automate compliance. Simplify security.

—

Find the transcript and references at: https://www.lennysnewsletter.com/p/frameworks-for-growing-your-career-bangaly-kaba

—

Where to find Bangaly Kaba:

• X: https://twitter.com/iambangaly

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

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

—

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) Bangaly’s background

(06:31) Choosing where to work and what to work on

(08:39) The impact factor

(10:53) Evaluating the environment

(15:53) The manager component

(18:27) The skills part of the equation

(23:49) Advice on finding a mentor

(25:42) The power of “understand work”

(31:17) Operationalizing understand work

(37:55) Balancing understand work

(41:25) Managing complex change

(45:26) Effective management of product managers

(51:35) The role of product managers as coaches and team leaders

(54:52) Driving growth through flywheels and value proposition

(01:03:14) Understanding adjacent users

(01:08:41) The role of partnerships and SEO in Instagram’s early growth

(01:16:08) The secret behind Instagram’s growth

(01:25:37) Lessons from Facebook

(01:29:15) Failure corner

(01:31:58) Lightning round

—

Referenced:

• Impact = Environment x Skills: How to Make Career Decisions: https://www.reforge.com/blog/how-to-make-career-decisions

• Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub): https://www.lennysnewsletter.com/p/thinking-beyond-frameworks-casey

• Casey Winters’s blog: https://caseyaccidental.com/

• Ben Thompson’s newsletter: https://stratechery.com/about/

• 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

• George Lee on LinkedIn: https://www.linkedin.com/in/geolee/

• Bangaly Kaba: The Path to 1 Billion: Lessons Learned from Growing Instagram—CXL LIVE 2018: https://www.youtube.com/watch?v=L9ZHlb6kj_E

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

• Bloom’s taxonomy: https://en.wikipedia.org/wiki/Bloom%27s_taxonomy

• Kevin Systrom on LinkedIn: https://www.linkedin.com/in/kevinsystrom/

• Mike Krieger on LinkedIn: https://www.linkedin.com/in/mikekrieger/

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

• Kobe Bryant: https://en.wikipedia.org/wiki/Kobe_Bryant

•  Mike Krzyzewski: https://en.wikipedia.org/wiki/Mike_Krzyzewski

• John Calipari: https://en.wikipedia.org/wiki/John_Calipari

• Stripe: https://stripe.com/

• Chief: https://chief.com/

• Jobs to be done framework: https://jobs-to-be-done.com/jobs-to-be-done-a-framework-for-customer-needs-c883cbf61c90

• The Adjacent User: https://brianbalfour.com/quick-takes/the-adjacent-user

• How the biggest consumer apps got their first 1,000 users: https://www.lennysnewsletter.com/p/how-the-biggest-consumer-apps-got

• Alex Zhu on LinkedIn: https://www.linkedin.com/in/keepsilence/

• From Brush to Canvas with Alex Zhu of Musical.ly: https://www.youtube.com/watch?v=ey15v81pwII

• Selena Gomez on Instagram: https://www.instagram.com/selenagomez/

• Kim Kardashian on Instagram: https://www.instagram.com/kimkardashian/

• Rob Andrews on LinkedIn: https://www.linkedin.com/in/robby-andrews-64669720/

• Instagram’s growth speeds up as it hits 700 million users: https://techcrunch.com/2017/04/26/instagram-700-million-users/

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

• Deep Work: Rules for Focused Success in a Distracted World: https://www.amazon.com/Deep-Work-Focused-Success-Distracted/dp/1455586692

• Start at the End: How to Build Products That Create Change: https://www.amazon.com/Start-End-Products-Create-Change/dp/0525534423

• Flighty app: https://www.flightyapp.com/

• Adam Grant on Instagram: https://www.instagram.com/adamgrant/

—

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.

Kenneth Berger coaches startup leaders on how to prevent burnout, advocate for their desired lifestyle, and make a meaningful impact on the world. He’s spent more than 20 years in the tech industry, is a former founder backed by top investors, and was the first product manager at Slack. Kenneth’s core mission is to help startup leaders change the world by learning to ask for what they want, living with integrity, and building genuine relationships even with the people they find most challenging. Currently he is writing a book, Ask for What You Want, in which he aims to share his actionable strategies for creating change in the world. In our conversation, we explore:

• Why asking for what you want is so impactful

• Three steps to effectively ask for what you want

• Challenges that arise when people struggle to ask for what they want

• Why hearing “no” is a normal part of the process

• The “dream behind the complaint” technique for uncovering desires

• Kenneth’s experience of being fired three times from Slack

• How embracing fear and discomfort is key to getting what you want

• Why discipline is overrated

—

Brought to you by:

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• Vanta—Automate compliance. Simplify security

—

Find the transcript at: https://www.lennysnewsletter.com/p/ask-for-what-you-want-kenneth-berger

—

Where to find Kenneth Berger:

• X: https://twitter.com/kberger

• Threads: https://www.threads.net/@kberger

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

• Website: https://kberger.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) Kenneth’s background

(04:31) The importance of asking for what you want

(06:36) Challenges that arise when people struggle to ask for what they want

(08:09) A personal example of failing to ask for what you want

(09:17) Signs this is a skill you need to work on

(10:49) How to get better at knowing what you want

(15:28) Why hearing “no” is a normal part of the process

(17:29) Getting a “yes” vs. a “hell yes”

(19:20) Step 1: Articulate what you want

(24:07) Doing an integrity check

(26:56) Step 2: Ask for what you want intentionally

(30:45) Understanding your influence

(34:48) Using complaints as inspiration

(36:24) Internal family systems

(38:00) Giving feedback

(41:24) Step 3: Accept the response

(45:22) Kenneth’s experience of being fired three times from Slack

(57:30) Advice on being the first PM at a company or startup

(01:04:58) Contrarian corner: anti-discipline

(01:05:52) Lightning round

—

Referenced:

• Joining as the first product manager: https://www.lennysnewsletter.com/p/joining-as-the-first-product-manager

• Internal Family Systems: https://ifs-institute.com/

• How to build deeper, more robust relationships | Carole Robin (Stanford GSB professor, “Touchy Feely”): https://www.lennysnewsletter.com/p/build-robust-relationships-carole-robin

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

• The Three Realities Framework | The 15% Rule | Feedback Guidelines: https://www.lennysnewsletter.com/p/build-robust-relationships-carole-robin

• T-group weekends at Stanford: https://www.gsb.stanford.edu/experience/learning/leadership/interpersonal-dynamics/facilitation-training-program/intro-tgroup

• DBT skill DEAR MAN: https://www.therapistaid.com/therapy-worksheet/dbt-dear-man

• Dialectical behavior therapy (DBT): https://my.clevelandclinic.org/health/treatments/22838-dialectical-behavior-therapy-dbt

• 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

• Stewart Butterfield on LinkedIn: https://www.linkedin.com/in/butterfield/

• How to fire people with grace, work through fear, and nurture innovation | Matt Mochary (CEO coach): https://www.lennysnewsletter.com/p/how-to-fire-people-with-grace-work

• 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

• Jonny Miller’s Nervous System Mastery course: https://nsmastery.com/lenny

• Managing nerves, anxiety, and burnout | Jonny Miller (Nervous System Mastery): https://www.lennysnewsletter.com/p/managing-nerves-anxiety-and-burnout

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

• Break Point on Netflix: https://www.netflix.com/title/81569920

• Living on Netflix: https://www.netflix.com/title/81582076

• Wimbledon tennis: https://www.wimbledon.com

• Wenshan Baozhong tea: https://redblossomtea.com/products/wenshan-baozhong?variant=31629962820

• Tea From Taiwan: https://www.teafromtaiwan.com/

—

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

—

Lenny may be an investor in the companies discussed.

Jag Duggal is chief product officer at Nubank, a decacorn neobank founded in Brazil. It’s valued at over $30 billion, is bigger than Coinbase, Robinhood, Affirm, and SoFi combined, has 100 million customers (more than Bank of America!) while only operating in three countries in Latin America, and 80% to 90% of its growth comes through word of mouth. Prior to Nubank, Jag was a director of product management at Facebook, a senior vice president at Quantcast, and a product leader at Google. In our conversation, we discuss:

• How Nubank builds a fanatical user base

• Tactics for driving word-of-mouth growth

• Measuring customer love through the Sean Ellis score

• The importance of strategic clarity

• The role of category design in creating successful products

• Why companies should strive to be “fundamentally different,” not “incrementally better”

• Nubank’s vision for an AI-powered banking future

—

Brought to you by:

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

• Mercury—The powerful and intuitive way for ambitious companies to bank

• OneSchema—Import CSV data 10x faster

—

Find the transcript at: https://www.lennysnewsletter.com/p/be-fundamentally-different-jag-duggal

—

Where to find Jag Duggal:

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

—

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) Jag’s background

(04:34) Nubank’s remarkable achievements

(06:01) Nubank’s product development process

(11:23) Nubank’s values

(12:16) Building products people love fanatically

(15:21) The Sean Ellis score

(21:27) An example project using the Sean Ellis score

(25:07) Picking up the phone and calling customers

(28:20) The importance of starting small and iterating

(30:42) Pushing back effectively

(34:10) Uncovering pain points through customer research

(37:53) An example of setting a clear hypothesis

(42:01) Developing a strategy

(52:16) “Be fundamentally different, not incrementally better”

(53:10) Category design

(57:37) Nubank’s founding story and goals for the future

(01:00:46) Advice for adding new product lines

(01:03:46) The future of fintech and banking

(01:09:23) AI corner

(01:12:34) Failure corner

(01:20:24) Key takeaways

(01:22:11) Lightning round

—

Referenced:

• Nubank: https://nubank.com.br/en/

• Coinbase: https://www.coinbase.com/

• Robinhood: https://www.robinhood.com/

• SoFi: https://www.sofi.com/

• Affirm: https://www.affirm.com/

• Lemonade: https://www.lemfi.com/

• Bank of America: https://www.bankofamerica.com/

• Nubank achieves a world record with more than 7 million people participating in NuBolão in one month: https://building.nubank.com.br/nubank-achieves-world-record-with-nubolao

• Nu México carries out first financial transaction 20 meters under the depth of the sea: https://www.bnamericas.com/en/news/nu-mexico-carries-out-first-financial-transaction-20-meters-under-the-depth-of-the-sea

• David Vélez on LinkedIn: https://www.linkedin.com/in/david-v%C3%A9lez-1004875

• Cristina Junqueira on LinkedIn: https://www.linkedin.com/in/crisjunqueira

• Edward Wible on LinkedIn: https://www.linkedin.com/in/adamedwardwible

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

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

• Nubank’s real foundation: our culture and values: https://building.nubank.com.br/nubank-culture-and-values/

• Working Backwards Press Release Template and Example: https://www.linkedin.com/pulse/working-backwards-press-release-template-example-ian-mcallister/

• Sean Ellis test: https://productcoalition.com/using-sean-ellis-test-for-measuring-your-product-market-fit-c8ac98053c2c

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

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

• Ultravioleta: Nubank expands its premium card offer and adds new features on the product’s first anniversary: https://international.nubank.com.br/company/ultravioleta-nubank-expands-its-premium-card-offer-and-adds-new-features-on-the-products-first-anniversary/

• Jeff Bezos: Amazon and Blue Origin | Lex Fridman Podcast #405: https://www.youtube.com/watch?v=DcWqzZ3I2cY

• The Innovation Method Behind Swiffer Madness: https://www.fastcompany.com/3006797/innovation-method-behind-swiffer-madness

• Kevin Systrom on LinkedIn: https://www.linkedin.com/in/kevinsystrom/

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

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

• The Crux: How Leaders Become Strategists: https://www.amazon.com/Crux-How-Leaders-Become-Strategists/dp/1541701240/

• How to become a category pirate | Christopher Lochhead (author of Play Bigger, Niche Down, Category Pirates, more): https://www.lennysnewsletter.com/p/how-to-become-a-category-pirate-christopher

• Play Bigger: How Pirates, Dreamers, and Innovators Create and Dominate Markets: https://www.amazon.com/Play-Bigger-Dreamers-Innovators-Dominate/dp/0062407619

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

• A framework for finding product-market fit | Todd Jackson (First Round Capital): https://www.lennysnewsletter.com/p/a-framework-for-finding-product-market

• Citi: https://www.citi.com/

• Santander Bank: https://www.santanderbank.com/

• Fidji Sumo on LinkedIn: https://www.linkedin.com/in/fidjisimo/

• Harvard Kennedy School: https://www.hks.harvard.edu/

• Susan Wojcicki on LinkedIn: https://www.linkedin.com/in/susan-wojcicki-b136a99/

• Coldplay—“Lost+” ft. Jay-Z: https://www.youtube.com/watch?v=PkCDRm_YRFg

• Google Buys DoubleClick for $3.1 Billion: https://www.nytimes.com/2007/04/14/technology/14DoubleClick.html

• Real-time bidding: https://support.google.com/authorizedbuyers/answer/6136272

• From Third World to First: The Singapore Story: 1965-2000: https://www.amazon.com/Third-World-First-Singapore-1965-2000/dp/0060197765/

• The Gilded Age on HBO: https://www.hbo.com/the-gilded-age

• Lomi: https://lomi.com/

• Nubank careers: https://international.nubank.com.br/careers/

—

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.

Vikrama Dhiman heads all things product at Gojek, including product management, design, program management, and research, across Indonesia, Singapore and India. He has over 16 years of experience building internet products, consults with Fortune 500 companies, and is among the most well-known and respected product leaders in all of Asia. In our conversation, we discuss:

• The most common traits among successful product managers

• The 3 W’s framework for PM career growth

• The Four A’s of leveling up in product management

• The right way to push back as a PM

• Common pitfalls that stall PM careers

• Vikrama’s advice for transitioning into product management

• Why intent alone is not enough

—

Brought to you by:

• Uizard—AI-powered prototyping for visionary product leaders

• Webflow—The web experience platform

• Coda—The all-in-one collaborative workspace

—

Find the transcript at: https://www.lennysnewsletter.com/p/a-framework-for-pm-skill-development

—

Where to find Vikrama Dhiman:

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

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

• Website: https://www.vikramadhiman.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) Vikrama’s background

(03:56) Three common traits among great PMs

(07:09) The first W: What you produce

(15:40) The second W: What you bring to the table

(18:58) The third W: What’s your operating model?

(20:36) Three traits that make you a great PM to work with

(21:49) How to improve the quality and quantity of your outputs

(23:26) The art of the pushback

(26:55) Common factors that impede career growth

(33:39) Vikrama’s personal reflections

(39:33) Choosing which skill(s) to focus on developing

(46:28) The ambiguity of the PM role

(51:47) The 8 axis for PM growth

(56:57) Contrarian corner: Why intent alone is not enough

(59:30) Lightning round

—

Referenced:

• Taxi mafias, cash vaults, and 100% MoM growth: The story behind Southeast Asia’s biggest startup | Kevin Aluwi (Gojek): https://www.lennysnewsletter.com/p/taxi-mafias-cash-vaults-and-100-mom

• How to scrappily hire for, measure, and unlock growth | Crystal Widjaja, Gojek and Kumu: https://www.lennysnewsletter.com/p/how-to-hire-for-measure-and-unlock

• Gojek: https://www.gojek.com/en-id

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

• Oracle: https://www.oracle.com/

• Crystal Widjaja on LinkedIn: https://www.linkedin.com/in/crystalwidjaja

• Raditya Wibowo: https://www.linkedin.com/in/raditya-wibowo-a0845436/?originalSubdomain=id

• Sidu Ponnappa on LinkedIn: https://www.linkedin.com/in/sidup

• Leveraging mentors to uplevel your career | Jules Walter (YouTube, Slack): https://www.lennysnewsletter.com/p/leveraging-mentors-to-uplevel-your

• Kevin Aluwi on LinkedIn: https://www.linkedin.com/in/kaluwi/

• Workday: https://www.workday.com/

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

• Small Data: The Tiny Clues That Uncover Huge Trends: https://www.amazon.com/Small-Data-Clues-Uncover-Trends/dp/1250080681

• Originals: How Non-Conformists Move the World: https://www.amazon.com/Originals-How-Non-Conformists-Move-World/dp/014312885X

• Thinking, Fast and Slow: https://www.amazon.com/Thinking-Fast-Slow-Daniel-Kahneman/dp/0374533555

• Miss Congeniality on Prime Video: https://www.amazon.com/Miss-Congeniality-Sandra-Bullock/dp/B002R5HQDK

• Schitt’s Creek on Prime Video: https://www.amazon.com/Schitts-Creek/dp/B083LDRW9F

• DramaBox: https://www.dramaboxapp.com/

• Am I Overthinking This?: Over-Answering Life’s Questions in 101 Charts: https://www.amazon.com/Am-Overthinking-This-Over-answering-questions/dp/1452175861/

• Crazy Rich Asians on Prime Video: https://www.amazon.com/Crazy-Rich-Asians-Constance-Wu/dp/B07JGJFXBF

• 9 Best Hawker Centers in Singapore—and What to Eat There: https://www.afar.com/magazine/best-hawker-centers-in-singapore-and-what-to-eat-there

—

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.

Hamilton Helmer is one of the world’s leading experts on business strategy and the author of the seminal book 7 Powers: The Foundations of Business Strategy, which provides a comprehensive framework for understanding what it really takes to achieve and sustain a competitive advantage. With more than three decades of experience in the strategic consulting industry, Hamilton has advised over 200 companies—from burgeoning startups to Fortune 100 giants—on how to identify, build, and leverage their unique strategic powers. In our conversation, we discuss:

• Potential sources of power that startups should develop from an early stage

• Common misconceptions among companies about the types of power they possess

• How power relates to strategy

• The difference between a moat and a power

• Practical strategies for non-leaders to leverage insights about power and strategy in their work

• AI’s impact on competitive advantages and barriers to entry

—

Brought to you by:

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

• Vanta—Automate compliance. Simplify security

• Paragon—Ship every SaaS integration your customers want

—

Find the transcript and references at: https://www.lennysnewsletter.com/p/business-strategy-with-hamilton-helmer

—

Where to find Hamilton Helmer:

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

• LinkedIn: https://www.linkedin.com/in/hamilton-helmer-42983/

• Website: https://7powers.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) Hamilton’s background

(04:08) When power becomes important

(08:24) How strategy relates to power

(12:09) How power informs strategy

(14:46) The sequence of powers

(21:13) Common misconceptions

(24:39) Network effects vs. network economies

(26:58) Uber’s success

(29:16) Moats vs. powers

(31:12) Strategies for non-leaders to leverage power and strategy

(37:51) Advice on how to become a strategic thinker

(39:27) AI’s impact on the seven powers

(45:43) Why moving fast is not a power

(50:24) Three things that create value in a company

(51:16) The debt trajectory of the U.S.

(56:35) Optimism for the future

(59:25) Lightning round

—

Referenced:

• 7 Powers: The Foundations of Business Strategy: https://www.amazon.com/7-Powers-Foundations-Business-Strategy/dp/0998116319

• John von Neumann: https://en.wikipedia.org/wiki/John_von_Neumann

• Pearl Harbor: https://www.history.com/topics/world-war-ii/pearl-harbor

• Where the Japanese Went Wrong at Pearl Harbor: https://pearlharbor.org/blog/where-japanese-went-wrong-pearl-harbor/

• The ‘7 Powers’ of business success—from one of Netflix’s early investors: https://www.qualitycompounders.com.au/post/the-7-powers-of-business-success-from-one-of-netflix-s-early-investors

• 7 Powers: Foundations of Business Strategy (Key Takeaways): https://www.linkedin.com/pulse/7-powers-foundations-business-strategy-key-takeaways-nikita-maloo/

• Strategy Capital: https://strategycapital.com/

• Warren Buffett: https://www.forbes.com/profile/warren-buffett/

• Charlie Munger: https://www.forbes.com/profile/charles-munger/

• Poor Charlie’s Almanack: The Essential Wit and Wisdom of Charles T. Munger: https://www.stripe.press/poor-charlies-almanack

• Bill Gates reveals why Warren Buffett was an invaluable source of support during the stormiest period of his career: https://www.businessinsider.com/bill-gates-interview-warren-buffett-support-microsoft-antitrust-lawsuit-2019-6

•  Billionaire Warren Buffett’s Secret Love Affair With Castles, Revealed: https://www.thestreet.com/opinion/billionaire-warren-buffett-s-secret-love-affair-with-castles-revealed-14290973

• Netflix didn’t kill Blockbuster—how Netflix almost lost the movie rental wars: https://www.cnbc.com/2020/09/22/how-netflix-almost-lost-the-movie-rental-wars-to-blockbuster.html

• Michael Porter on LinkedIn: https://www.linkedin.com/in/professorporter/

• What Is Strategy?: https://hbr.org/1996/11/what-is-strategy

• TSMC: https://www.tsmc.com/english

• Toyota Production System: https://en.wikipedia.org/wiki/Toyota_Production_System

• America will be left with ‘severe, irreversible scars’ if national debt goes unchecked. Now, a blockbuster report warns the bill is higher than believed, hitting $141T by 2054: https://fortune.com/2024/04/01/america-social-economic-scars-us-debt-gomes-price/

• Ben S. Bernanke: https://www.federalreservehistory.org/people/ben-s-bernanke

• Forty-four of 50 U.S. states worsen inequality with ‘upside-down’ taxes: https://www.theguardian.com/us-news/2024/jan/10/states-wealth-inequality-taxes

• Joseph A. Schumpeter: https://en.wikipedia.org/wiki/Joseph_Schumpeter

• Theory of Economic Development: https://www.amazon.com/Theory-Economic-Development-Science-Classics/dp/0878556982

• The Road to Reality: A Complete Guide to the Laws of the Universe: https://www.amazon.com/Road-Reality-Complete-Guide-Universe/dp/0679776311

• The Gene: An Intimate History: https://www.amazon.com/Gene-Intimate-History-Siddhartha-Mukherjee/dp/147673352X

• American Fiction on Prime Video: https://www.amazon.com/American-Fiction-Jeffrey-Wright/dp/B0CQKR72NX

• Farahan Sarouk rugs: https://nazmiyalantiquerugs.com/persian-sarouk-farahan-rugs/

• Rory Sutherland on LinkedIn: https://www.linkedin.com/in/rorysutherland

• Ogilvy: https://www.ogilvy.com/

• Clint Eastwood quote: https://www.brainyquote.com/quotes/clint_eastwood_168005

• Winston Churchill: https://en.wikipedia.org/wiki/Winston_Churchill

• Michelangelo, God’s Architect: The Story of His Final Years and Greatest Masterpiece: https://www.amazon.com/Michelangelo-Gods-Architect-Greatest-Masterpiece/dp/0691195498

• The Last Judgment: https://en.wikipedia.org/wiki/The_Last_Judgment_(Michelangelo)

• Theodore Roosevelt: https://www.whitehouse.gov/about-the-white-house/presidents/theodore-roosevelt/

—

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.

Annie Duke is a former professional poker player, a decision-making expert, and a special partner at First Round Capital. She is the author of Thinking in Bets (a national bestseller) and Quit: The Power of Knowing When to Walk Away and the co-founder of the Alliance for Decision Education, a nonprofit whose mission is to improve lives by empowering students through decision skills education. In our conversation, we cover:

• What Annie learned from the late Daniel Kahneman

• The power of pre-mortems and “kill criteria”

• The relationship between money and happiness

• The power of “mental time travel”

• The nominal group technique for better decision quality

• How First Round Capital improved their decision-making process

• Many tactical decision-making frameworks

—

Brought to you by:

• Vanta—Automate compliance. Simplify security.

• UserTesting—Human understanding. Human experiences.

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

—

Find the transcript at: https://www.lennysnewsletter.com/p/making-better-decisions-annie-duke

—

Where to find Annie Duke:

• X: https://twitter.com/AnnieDuke

• LinkedIn: https://www.linkedin.com/in/annie-duke/

• Website: https://www.annieduke.com/

• Substack: https://www.annieduke.com/substack/

—

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) Annie’s background

(03:53) Lessons from Daniel Kahneman: humility, curiosity, and open-mindedness

(09:15) The importance of unconditional love in parenting

(15:15) Mental time travel and “nevertheless”

(20:06) The extent of improvement possible in decision-making 

(24:54) Independent brainstorming for better decisions

(35:36) Making sure people feel heard

(42:41) The “3Ds” framework to make better decisions

(44:49) Decision quality

(55:46) Improving decision-making at First Round Capital

(01:05:05) Using pre-mortems and kill criteria

(01:10:15) Making explicit what’s implicit

(01:10:55) The challenges of quitting and knowing when to walk away

(01:19:23) Where to find Annie

—

Referenced:

• Daniel Kahneman, Who Plumbed the Psychology of Economics, Dies at 90: https://www.nytimes.com/2024/03/27/business/daniel-kahneman-dead.html

• Adversarial collaboration: https://en.wikipedia.org/wiki/Adversarial_collaboration

• Does more money correlate with greater happiness?: https://penntoday.upenn.edu/news/does-more-money-correlate-greater-happiness-Penn-Princeton-research#

• Income and emotional well-being: A conflict resolved: https://pubmed.ncbi.nlm.nih.gov/36857342/

• Strategic decisions: When can you trust your gut?: https://www.mckinsey.com/capabilities/strategy-and-corporate-finance/our-insights/strategic-decisions-when-can-you-trust-your-gut

• Cass Sunstein on X: https://twitter.com/CassSunstein

• Dr. Becky on Instagram: https://www.instagram.com/drbeckyatgoodinside

• A framework for finding product-market fit | Todd Jackson (First Round Capital): https://www.lennysnewsletter.com/p/a-framework-for-finding-product-market

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

• Brett Berson on X: https://twitter.com/brettberson

• Renegade Partners: https://www.renegadepartners.com/

• Renata Quintini on X: https://twitter.com/rquintini

• Roseanne Wincek on X: https://twitter.com/imthemusic

• Josh Kopelman on X: https://twitter.com/joshk

• Bill Trenchard on X: https://twitter.com/btrenchard

• Linnea Gandhi on X: https://twitter.com/linneagandhi

• Maurice Schweitzer on X: https://twitter.com/me_schweitzer

• Problems with premortems: https://sjdm.org/presentations/2021-Poster-Gandhi-Linnea-debiasing-premortem-selfserving~.pdf

• Create a Solid Plan on How to Fail Big This Year: https://www.forbes.com/sites/forbesfinancecouncil/2020/02/07/create-a-solid-plan-on-how-to-fail-big-this-year/

• Quit: The Power of Knowing When to Walk Away: https://www.amazon.com/Quit-Power-Knowing-When-Walk/dp/0593422996/

• Richard Thaler on X: https://twitter.com/R_Thaler

• Stewart Butterfield on X: https://twitter.com/stewart

• Glitch: https://en.wikipedia.org/wiki/Glitch_(video_game)

• How the Founder of Slack & Flickr Turned Colossal Failures into Billion-Dollar Companies: https://medium.com/swlh/how-the-founder-of-slack-flickr-turned-failures-into-million-and-billion-dollar-companies-7bcaf0d35d66

• The Most Fascinating Profile You’ll Ever Read About a Guy and His Boring Startup: https://www.wired.com/2014/08/the-most-fascinating-profile-youll-ever-read-about-a-guy-and-his-boring-startup/

• The Alliance for Decision Education: https://alliancefordecisioneducation.org/

• Make Better Decisions course on Maven: https://maven.com/annie-duke/make-better-decisions

—

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.

Kayvon Beykpour was the longest-serving head of product at Twitter and was GM of Twitter’s consumer division until the platform was acquired by Elon Musk. He originally joined Twitter in 2015 through the acquisition of his company, Periscope, the largest live video streaming platform at the time. Periscope pioneered technology that inspired Instagram Live, TikTok Live, Facebook Live, and other social networks’ expansion into video streaming. In our conversation, we discuss:

• The story of being let go from Twitter after Elon’s acquisition

• How he turned Twitter’s stagnant culture around

• Kayvon’s thoughts on the limitations of frameworks like Jobs to Be Done

• Why Periscope failed

• Advice for building consumer products

• When to copy, when to innovate

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Find the transcript at: https://www.lennysnewsletter.com/p/twitters-former-head-of-product-kayvon-beykpour

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Where to find Kayvon Beykpour:

• X: https://twitter.com/kayvz

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

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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) Kayvon’s background

(04:31) Getting Elon up to speed at Twitter

(11:34) The story of being let go from Twitter after Elon’s acquisition

(21:09) Changing the product culture at Twitter

(29:44) Building the “hide replies” feature

(32:02) Sacred crows, taking bold bets, and reigniting growth

(34:28) Aquihires and their impact

(42:40) Tips for successful acquisitions and staffing

(47:00) The limitations of frameworks like JTBD

(53:20) Signs you’ve gone too far with a framework

(57:44) Lessons from building Periscope

(01:00:41) Reasons why Periscope failed

(01:07:24) The challenges of implementing video at Twitter

(01:12:05) Copying ideas in good taste

(01:17:58) How to get better at building consumer products

(01:19:51) What Kayvon is building

(01:20:31) Lightning round

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Referenced:

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

• What it’s like to sell your startup for ~$120 million before it’s even launched: Meet Twitter’s new prized possession, Periscope: https://www.businessinsider.com/what-is-periscope-and-why-twitter-bought-it-2015-3

• Walter Isaacson on LinkedIn: https://www.linkedin.com/in/walter-isaacson-b8b81520/

• Elon Musk on X: https://twitter.com/elonmusk

• Parag Agrawal on LinkedIn: https://www.linkedin.com/in/parag-agrawal-5a14742a/

• Jack Dorsey on LinkedIn: https://www.linkedin.com/in/jack-dorsey-a43b07242/

• Blackboard: https://en.wikipedia.org/wiki/Blackboard_Inc.

• Keith Coleman on X: https://twitter.com/kcoleman

• Esther Crawford on LinkedIn: https://www.linkedin.com/in/esthercrawford/

• Twitter acquires Chroma Labs: https://tech.hindustantimes.com/tech/news/twitter-acquires-chroma-labs-story-aqvcRPAoYXqXJuAbefA6cN.html

• John Barnett on LinkedIn: https://www.linkedin.com/in/johnbarnettt/

• Jobs to Be Done framework: https://jobs-to-be-done.com/jobs-to-be-done-a-framework-for-customer-needs-c883cbf61c90

• Hot takes and techno-optimism from tech’s top power couple: https://www.lennyspodcast.com/hot-takes-and-techno-optimism-from-techs-top-power-couple-sriram-and-aarthi/

• Nike Is Unveiling the Kobe 11 Tomorrow Using Periscope: https://sneakernews.com/2015/12/13/nike-is-unveiling-the-kobe-11-tomorrow-using-periscope/

• Chris Sacca’s website: https://chrissacca.com/

• Facebook Live: https://www.facebook.com/formedia/tools/facebook-live

• Kevin Hart on X: https://twitter.com/KevinHart4real