Lenny's Podcast: Product | Growth | Career

Elizabeth Stone is the chief technology officer of Netflix. She previously served as vice president of product data science and engineering, and as vice president of data and insights, at Netflix. Before Netflix, Elizabeth was vice president of science at Lyft, chief operating officer at Nuna, a trader at Merrill Lynch, and an economist at Analysis Group. In our conversation, we discuss:

• Elizabeth’s advice for career advancement

• Netflix’s unique high-performance culture

• How, and why, Netflix maintains a high bar for excellence

• Intentional leadership practices

• How to foster an “open door” culture within your team

• The Keeper Test and how it contributes to maintaining a high bar for excellence

• The power of transparent communication

• Much more

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Brought to you by:

• Vanta—Automate compliance. Simplify security.

• Sendbird—The (all-in-one) communications API platform for mobile apps

• Explo—Embed customer-facing analytics in your product

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Find the full transcript at: https://www.lennyspodcast.com/how-netflix-builds-a-culture-of-excellence-elizabeth-stone-cto/

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Where to find Elizabeth Stone:

• LinkedIn: https://www.linkedin.com/in/elizabeth-stone-608a754/

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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) Elizabeth’s background

(04:36) Life as CTO vs. VP of Data

(05:57) The role of economists in tech companies

(08:32) Using economics to understand incentives

(10:07) Success and career growth

(20:15) Setting expectations

(25:02) Advice for how to avoid burnout

(27:44) Netflix culture: high talent density

(30:31) Netflix culture: candor and directness

(31:45) The Keeper Test

(39:01) Maintaining a high bar for excellence

(43:54) Netflix culture: freedom and responsibility

(46:18) Unconventional processes at Netflix

(47:55) Examples of candor

(51:44) Data and insights team structure

(01:00:12) Staying close to teams

(01:02:31) Advice on being present

(01:07:40) Lightning round

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Referenced:

• What to Know About the Netflix Cup, Today’s First-Ever Live Sports Event: https://www.netflix.com/tudum/articles/netflix-cup-live-event-date-news

• Ann Miura Ko interview | The Tim Ferriss Show (Podcast): https://www.youtube.com/watch?v=h2GO0Ks_VGg

• Netflix culture: https://jobs.netflix.com/culture

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

• Reed Hastings on LinkedIn: https://www.linkedin.com/in/reedhastings/

• Netflix’s “Keeper Test” and Why You Need It | Lorne Rubis: https://www.highlights.lornerubis.com/2015/08/the-netflix-keeper-test-and-the-courage-to-take-it/

• The Hunger Games: https://en.wikipedia.org/wiki/The_Hunger_Games

• Nan Yu on LinkedIn: https://www.linkedin.com/in/thenanyu/

• Work Life Philosophy: https://jobs.netflix.com/work-life-philosophy

• The Scoop: Netflix’s historic introduction of levels for software engineers: https://blog.pragmaticengineer.com/netflix-levels/

• Chaos Monkey: https://www.techtarget.com/whatis/definition/Chaos-Monkey

• Ali Rauh on LinkedIn: https://www.linkedin.com/in/ali-rauh/

• Keith Henwood on LinkedIn: https://www.linkedin.com/in/keith-henwood/

• Jeff Bezos’ Morning Routine of Puttering Around—How It Works: https://medium.com/illumination/jeff-bezos-morning-routine-of-puttering-around-how-it-works-9d73f359ac8d

• What I Talk About When I Talk About Running: A Memoir: https://www.amazon.com/What-Talk-About-When-Running/dp/0307389839

• A Fine Balance: https://www.amazon.com/Fine-Balance-Rohinton-Mistry/dp/140003065X

• Triangle of Sadness on Hulu: https://www.hulu.com/movie/triangle-of-sadness-f60937bd-45f4-469a-938f-db95026953a1

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

• Fellow pour-over coffee set: https://fellowproducts.com/products/stagg-xf-pour-over-set

• Peloton bikes: https://www.onepeloton.com/shop/bike

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

—

Lenny may be an investor in the companies discussed.

Jason Lemkin created and runs SaaStr, the world’s largest community for B2B/SaaS founders, and is the managing director of SaaStr Fund, a $90 million venture capital firm specializing in early-stage enterprise investments. He is also the mastermind behind two major tech conferences each year—one in the Bay Area, drawing in over 15,000 people, and another in Europe, with a crowd of more than 3,000 SaaS executives, founders, and entrepreneurs. Before SaaStr, Jason wore many hats: CEO and co-founder of EchoSign (later bought by Adobe), vice president at Adobe Systems, co-founder and president of NanoGram Devices Corp., vice president of NeoPhotonics, and a senior director at BabyCenter. In our conversation, we discuss:

• How far you should go without a salesperson

• Signs it’s time to hire salespeople

• Why you need to hire two salespeople

• How to compensate your salespeople

• How to interview salespeople

• When to hire a VP of Sales

• How to prevent their flaming out

• How to scale your sales org

• How to improve the relationship between your sales and product teams

• Much more

—

Brought to you by:

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

• Vanta—Automate compliance. Simplify security.

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

—

Find the full transcript at: https://www.lennyspodcast.com/building-a-world-class-sales-org-jason-lemkin-saastr/

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Where to find Jason Lemkin:

• X: https://twitter.com/jasonlk

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

• Website: https://www.saastr.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) Jason’s background

(06:18) The importance of sales in B2B businesses

(11:23) Signs that you should start hiring salespeople

(14:19) Attributes to look for in early sales reps

(19:08) Hiring a VP of Sales

(26:43) The role of a VP of Sales

(30:06) Interviewing salespeople

(45:16) Determining sales compensation and quota

(53:34) Transitioning from 100% commission to a smaller percentage

(56:58) Indicators of a hard-to-sell product

(59:39) Scaling the sales organization

(01:05:26) Understanding sales roles and titles

(01:10:02) Product involvement in sales, and vice versa

(01:20:32) Thoughts on product teams taking on P&L responsibilities

(01:27:23) One thing founders can do to become better at sales

(01:31:02) The ideal trial length for a free trial sales team

(01:39:50) Closing thoughts

(01:41:43) Lightning round

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Referenced:

• Marc Benioff on LinkedIn: https://www.linkedin.com/in/marcbenioff/

• Snowflake: https://www.snowflake.com/en/

• Yamini Rangan on LinkedIn: https://www.linkedin.com/in/yaminirangan/

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

• HubSpot: https://www.hubspot.com/

• Twilio: https://www.twilio.com/

• Cloudflare: https://www.cloudflare.com/

• GitHub: https://github.com/

• Columbo: https://www.imdb.com/title/tt1466074/

• What is Davos and why is it important? Your guide to the World Economic Forum’s annual meeting: https://www.euronews.com/next/2024/01/15/what-is-davos-and-why-is-it-important-your-guide-to-the-world-economic-forums-annual-meeti

• Adobe: https://www.adobe.com/

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

• Glengarry Glen Ross on Prime Video: https://www.amazon.com/Glengarry-Glen-Ross-James-Foley/dp/B002NN5F7A

• The Wolf of Wall Street on Prime Video: https://www.amazon.com/Wolf-Wall-Street-Leonardo-DiCaprio/dp/B00IIU9FQY

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

• Pipedrive: https://www.pipedrive.com/

• Sam Blond on LinkedIn: https://www.linkedin.com/in/sam-blond-791026b/

• Gong: https://www.gong.io/

• Zendesk: https://www.zendesk.com/

• ZoomInfo: https://www.zoominfo.com/

• Apollo: https://www.apollo.io/

• Daniel Chait on LinkedIn: https://www.linkedin.com/in/dhchait/

• SAP: https://www.sap.com/

• 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/

• VistaPrint: https://www.vistaprint.com/

• Procore: https://www.procore.com/

• Matt Mullenweg on LinkedIn: https://www.linkedin.com/in/mattm/

• Wordpress: https://wordpress.com/

• SaaStr University: https://app.saastruniversity.com/collections/20252

• From Impossible to Inevitable: How SaaS and Other Hyper-Growth Companies Create Predictable Revenue: https://www.amazon.com/Impossible-Inevitable-Hyper-Growth-Companies-Predictable/dp/1119531691

• Pavilion: https://www.joinpavilion.com/

• Top 10 Learnings about Free Trials with Tomasz Tunguz: https://www.youtube.com/watch?v=tfQNJpnxmMw

• The Terminal List on Prime Video: https://www.amazon.com/The-Terminal-List-Season-1/dp/B09HYNH8TK

• Top Gun: Maverick on Paramount: https://www.paramountmovies.com/movies/top-gun-maverick

• OpusClip app: https://www.opus.pro/

• OnePlus Open smartphone: https://www.amazon.com/OnePlus-Dual-SIM-Unlocked-Smartphone-Hasselblad/dp/B0CHN7M531/

• SaaStr conferences: https://www.saastr.com/events/

• Marketo: https://go.marketo.com/about-marketo-landingpage-emea.html

• Zoomtopia: https://zoomtopia.com/

• Money20/20: https://us.money2020.com/

• Shoptalk: https://shoptalk.com/

• Jeff Lawson on LinkedIn: https://www.linkedin.com/in/jeffiel/

• Eric Kwan on LinkedIn: https://www.linkedin.com/in/erickwan/

—

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

—

Lenny may be an investor in the companies discussed.

Jake Knapp and John Zeratsky are the authors of best-selling books Sprint and Make Time. They have helped more than 300 teams design new products and bring them to market, including those at YouTube, Gusto, One Medical Group, and Slack. Jake and John are co-founders of the venture capital firm Character, where they support startups with capital and sprints. Previously, they were operating partners at Google Ventures and, before that, design leaders at Google, where John worked on Google Ads and YouTube and Jake helped build Gmail and co-founded Google Meet. In our conversation, we discuss:

• “Busy bandwagon” and “infinity pools”

• Creating one “highlight” each day

• Their four-part framework for productivity

• How to use the calendar to design your day

• How creating friction can help you avoid distractions

• Tips on creating a distraction-free phone

• Strategies for managing email and distractions

• The importance of reflecting on the day and making time for meaningful work

• Design sprints

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Brought to you by:

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

• Whimsical—The iterative product workspace

• WorkOS—The modern API for auth and user identity

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Find the full transcript at: https://www.lennyspodcast.com/making-time-for-what-matters-jake-knapp-and-john-zeratsky-authors-of-sprint-and-make-time-co-fou/

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Where to find Jake Knapp:

• X: https://twitter.com/jakek

• LinkedIn: https://www.linkedin.com/in/jake-knapp/

• Website: https://jakeknapp.com/

—

Where to find John Zeratsky:

• X: https://twitter.com/jazer

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

• Website: https://johnzeratsky.com/

—

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) About Jake and John

(04:10) Recording the audiobook for Make Time

(06:06) What people often get wrong when trying to become more productive

(11:24) The busy bandwagon and infinity pools

(15:22) Real talk: Jake and John’s productivity levels

(20:10) The four-part framework for getting more done: Highlight, Laser, Energize, Reflect

(25:15) Step 1: Highlight

(28:08) Designing your day with a calendar

(30:52) The Groundhog Day mentality

(35:10) Tactical advice for implementing the highlight method

(39:30) An example of a failed highlight

(48:08) Step 2: Laser

(51:12) Creating intentional friction to avoid distractions

(57:28) Curating a distraction-free phone

(01:07:58) Resetting expectations and slowing your inbox

(01:14:51) Systems over willpower

(01:18:14) Managing email distractions

(01:18:49) Step 3: Energize

(01:22:05) Step 4: Reflect

(01:26:30) Introduction to Sprint

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Referenced:

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

• Sprint: How to Solve Big Problems and Test New Ideas in Just Five Days: https://www.amazon.com/Sprint-audiobook/dp/B019R2DQIY

• Make Time blog: https://maketime.blog/

• Make Time blog on X: https://twitter.com/maketimeblog

• Character: https://www.character.vc/

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

• Character Labs: https://www.character.vc/labs

• Strategies for becoming less distracted and improving focus | Nir Eyal (author of Indistractable and Hooked): https://www.lennyspodcast.com/strategies-for-becoming-less-distracted-and-improving-focus-nir-eyal-author-of-indistractable-and/

• Groundhog Day on Prime Video: https://www.amazon.com/Groundhog-Day-Bill-Murray/dp/B000SP1SH6

• Reclaim.ai: https://reclaim.ai/

• Feed Blocker for LinkedIn: https://chromewebstore.google.com/detail/feed-blocker-for-linkedin/eikaafmldiioljlilngpogcepiedpenf

• The Lord of the Rings: https://www.amazon.com/Lord-Rings-J-R-R-Tolkien/dp/0544003411

• MagSafe charger: https://www.amazon.com/Apple-MHXH3AM-A-MagSafe-Charger/dp/B08L5NP6NG/

• Nanit app: https://www.nanit.com/pages/nanit-app

• Arianna Huffington’s Phone Bed Charging Station: https://www.amazon.com/Arianna-Huffingtons-Charging-Station-Walnut/dp/B0799ZG1LY

• Cell Phone Lock Box with Timer: https://www.amazon.com/Portable-Android-Self-Discipline-Achieve-Addiction/dp/B0CG8V4YG3?th=1

• The 4-Hour Workweek: Escape 9-5, Live Anywhere, and Join the New Rich: https://www.amazon.com/4-Hour-Workweek-Escape-Live-Anywhere/dp/0307465357

• The Economist: https://www.economist.com/

• Odysseus: https://www.britannica.com/topic/Odysseus

• Mailman: https://www.mailmanhq.com/

• Future: https://www.future.co/

• Notion: https://www.notion.so/

• Miro: https://miro.com/

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

—

Lenny may be an investor in the companies discussed.

Logan Kilpatrick leads developer relations at OpenAI, supporting developers building with the OpenAI API and ChatGPT. He is also on the board of directors at NumFOCUS, the nonprofit organization that supports open source projects like Jupyter, Pandas, NumPy, and more. Before OpenAI, Logan was a machine-learning engineer at Apple and advised NASA on open source policy. In our conversation, we discuss:

• OpenAI’s fast-paced and innovative work environment

• The value of high agency and high urgency in your employees

• Tips for writing better ChatGPT prompts

• How the GPT Store is doing

• OpenAI’s planning process and decision-making criteria

• Where OpenAI is heading in the next few years

• Insight into OpenAI’s B2B offerings

• Why Logan “measures in hundreds”

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Brought to you by:

• Hex—Helping teams ask and answer data questions by working together

• Whimsical—The iterative product workspace

• Arcade Software—Create effortlessly beautiful demos in minutes

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Find the transcript for this episode and all past episodes at: https://www.lennyspodcast.com/episodes/. Today’s transcript will be live by 8 a.m. PT.

—

Where to find Logan Kilpatrick:

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

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

• Website: https://logank.ai/

—

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) Logan’s background

(03:49) The impact of recent events on OpenAI’s team and culture

(08:20) Exciting developments in AI interfaces

(09:52) Using OpenAI tools to make companies more efficient

(13:04) Examples of using AI effectively

(18:35) Prompt engineering

(22:12) How to write better prompts

(26:05) The launch of GPTs and the OpenAI Store

(32:10) The importance of high agency and urgency

(34:35) OpenAI’s ability to move fast and ship high-quality products

(35:56) OpenAI’s planning process and decision-making criteria

(40:22) The importance of real-time communication

(42:33) OpenAI’s team and growth

(44:47) Future developments at OpenAI

(47:42) GPT-5 and building toward the future

(50:38) OpenAI’s enterprise offering and the value of sharing custom applications

(52:30) New updates and features from OpenAI

(55:09) How to leverage OpenAI’s technology in products

(58:26) Encouragement for building with AI

(59:30) Lightning round

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Referenced:

• OpenAI: https://openai.com/

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

• Greg Brockman on X: https://twitter.com/gdb

• tldraw: https://www.tldraw.com/

• Harvey: https://www.harvey.ai/

• Boost Your Productivity with Generative AI: https://hbr.org/2023/06/boost-your-productivity-with-generative-ai

• Research: quantifying GitHub Copilot’s impact on developer productivity and happiness: https://github.blog/2022-09-07-research-quantifying-github-copilots-impact-on-developer-productivity-and-happiness/

• Lesson learnt from the DPD AI Chatbot swearing blunder: https://www.linkedin.com/pulse/lesson-learnt-from-dpd-ai-chatbot-swearing-blunder-kitty-sz57e/

• Dennis Yang on LinkedIn: https://www.linkedin.com/in/dennisyang/

• Tim Ferriss’s blog: https://tim.blog/

• Tyler Cowen on X: https://twitter.com/tylercowen

• Tom Cruise on X: https://twitter.com/TomCruise

• Canva: https://www.canva.com/

• Zapier: https://zapier.com/

• Siqi Chen on X: https://twitter.com/blader

• Runway: https://runway.com/

• Universal Primer: https://chat.openai.com/g/g-GbLbctpPz-universal-primer

• “I didn’t expect ChatGPT to get so good” | Unconfuse Me with Bill Gates: https://www.youtube.com/watch?v=8-Ymdc6EdKw

• Microsoft Azure: https://azure.microsoft.com/

• Lennybot: https://www.lennybot.com/

• Visual Electric: https://visualelectric.com/

• DALL-E: https://openai.com/research/dall-e

• The One World Schoolhouse: https://www.amazon.com/One-World-Schoolhouse-Education-Reimagined/dp/1455508373/ref=sr_1_1

• Why We Sleep: Unlocking the Power of Sleep and Dreams: https://www.amazon.com/Why-We-Sleep-Unlocking-Dreams/dp/1501144324

• Gran Turismo: https://www.netflix.com/title/81672085

• Gran Turismo video game: https://www.playstation.com/en-us/gran-turismo/

• Manta sleep mask: https://mantasleep.com/products/manta-sleep-mask

• WAOAW sleep mask: https://www.amazon.com/WAOAW-Sleep-Sleeping-Blocking-Blindfold/dp/B09712FSLY

—

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

—

Lenny may be an investor in the companies discussed.

Megan Cook is the head of product for Atlassian’s Jira software, which is used by 75% of Fortune 500 companies, has over 125,000 customers globally, over 15 different products, and is by far the most popular project management tool in the world. Megan has been at Atlassian for just under 11 years, and before this role, she was an analyst, a developer, and an Agile coach. In our conversation, we discuss:

• How to get buy-in for your ideas

• The value of starting small

• How, and why, creating space for play is so essential

• How Jira stays ahead of endless competition

• Atlassian’s approach to launching new product lines

• Tactical tips for making remote work, work

• A personal failure and the lessons learned from it

—

Brought to you by:

• Teal—Your personal career growth platform

• Sprig—Build a product people love

• Vanta—Automate compliance. Simplify security.

—

Find the transcript for this episode and all past episodes at: https://www.lennyspodcast.com/episodes/. Today’s transcript will be live by 8 a.m. PT.

—

Where to find Megan Cook:

• X: https://twitter.com/meganwcook

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

—

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) Megan’s background

(03:50) Creating space for play and psychological safety on teams

(07:36) Peer feedback groups

(10:30) Sharing stories of failure

(13:33) The “10 dollar” game for priorities

(15:24) Advice on making remote work, work

(24:16) Getting buy-in for your ideas

(28:33) The importance of staying open-minded

(34:05) A quick summary of how to get buy-in

(36:45) Fighting the good fight

(38:15) Identifying customer pain points

(43:04) Starting small and showing success

(46:08) Launching new product lines

(53:35) Atlassian’s gated process for new product ideas

(58:00) How Jira stays ahead of competitors

(01:04:28) Learning from failure

(01:08:30) Fight club

(01:10:08) Lightning round

—

Referenced:

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

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

• Bitbucket: https://bitbucket.org/product

• Ben Crowe on LinkedIn: https://www.linkedin.com/in/ben-crowe-67299714/

• Ash Barty on X: https://twitter.com/ashbarty

• Atlassian’s blog, Work Life: https://www.atlassian.com/blog

• Lessons learned: 1,000 days of distributed at Atlassian: https://www.atlassian.com/blog/distributed-work/distributed-work-report

• New research: How to make time for the work that matters: https://www.atlassian.com/blog/distributed-work/calendar-redesign-experiment

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

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

• Lenny’s swag store: https://lennyswag.com/

• What is CSAT and how do you measure it?: https://www.qualtrics.com/experience-management/customer/what-is-csat

• The UX research reckoning is here | Judd Antin (Airbnb, Meta): https://www.lennyspodcast.com/the-ux-research-reckoning-is-here-judd-antin-airbnb-meta/

• Charlie Sutton on LinkedIn: https://www.linkedin.com/in/charliesutton/

• Nokia 6100: https://en.wikipedia.org/wiki/Nokia_6100

• Compass: https://www.atlassian.com/software/compass

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

• Canva: https://www.canva.com/

• Inspired: How to Create Tech Products Customers Love: https://www.amazon.com/INSPIRED-Create-Tech-Products-Customers/dp/1119387507

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

• Foundation on AppleTV+: https://tv.apple.com/us/show/foundation/umc.cmc.5983fipzqbicvrve6jdfep4x3

• Foundation book series: https://www.amazon.com/Foundation-3-Book-Boxed-Set-Empire/dp/0593499573

• Traeger smoker: https://www.traeger.com/shop/wood-pellet-grills

—

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

—

Lenny may be an investor in the companies discussed.

Jonny Miller is the founder of Nervous System Mastery, a course that has helped hundreds of founders and tech leaders cultivate calm, reduce nervousness, enhance resilience, and elevate their sense of aliveness. Having personally benefited from Jonny’s teachings, I’m especially excited to have him on the show. In this episode, we discuss:

• How shifting your focus from the mind to the body can help ease nervousness

• The power of breath in changing states

• The importance of “interoception”

• Specific breathing exercises to both calm and excite your nervous system

• The A.P.E. (awareness, posture, and emotion) framework for recognizing body signals

• The “feather, brick, dump truck” phenomenon

• The concept of emotional debt and how to release it

• The competitive advantage of feeling emotions

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Jonny’s five-week boot camp, Nervous System Mastery, will equip you with evidence-backed protocols to cultivate greater calm and agency over your internal state. Learn to rewire maladaptive stress responses and improve your sleep (use code LENNY for $250 discount). Apply here.

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Brought to you by:

• Teal—Your personal career growth platform

• Vanta—Automate compliance. Simplify security.

• Miro—A collaborative visual platform where your best work comes to life

—

Find the full transcript at: https://www.lennyspodcast.com/managing-nerves-anxiety-and-burnout-jonny-miller-nervous-system-mastery/

—

Where to find Jonny Miller:

• X: https://twitter.com/jonnym1ller

• LinkedIn: https://www.linkedin.com/in/jonnym1ller/

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

• Podcast: podcast.curioushumans.com 

• Email: jonny@curioushumans.com

• Course: https://nsmastery.com/lenny

—

Where to find Lenny:

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

• X: https://twitter.com/lennysan

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

—

In this episode, we cover:

(00:00) Jonny’s background

(07:19) The bottom-up approach to nervousness and anxiety

(09:42) The power of breath in changing states

(11:47) The concept of state over story

(13:56) Personal experiences with nervousness

(15:01) Breathing exercises to calm you down

(20:40) The “espresso” breath exercise to give you energy

(25:44) Interoception and the A.P.E. framework

(34:47) The “feather, brick, dump truck” phenomenon

(37:40) Recognizing emotional debt and avoiding burnout

(40:47) Using somatic-oriented therapy for healing

(45:26) Telltale signs of emotional debt

(48:13) The competitive advantage of “feeling the feels”

(50:20) Advice for people overwhelmed by stimuli

(52:36) The NSDR (non-sleep deep rest) practice for emotional release

(55:38) Daily practices for emotional well-being

(58:23) Thoughts on meditation

(01:01:26) The Body Keeps the Score

(01:01:58) Contrarian corner

(01:04:43) Lightning round

—

Jonny’s If [This] Then [Breathe] Recipes:

• If [overwhelmed], then [hum]

• If [anxious], then [breath of calm]

• If [lethargic], then [espresso breath]

—

Referenced:

• The Operating Manual for Your Nervous System: https://every.to/p/the-operating-manual-for-your-nervous-system

• Afferent vs. Efferent Neurons: https://www.osmosis.org/answers/afferent-vs-efferent-neurons

• Insular cortex: https://en.wikipedia.org/wiki/Insular_cortex

• Jonny’s TED Talk, “The gifts of grief”: https://www.ted.com/talks/jonny_miller_the_gifts_of_grief/details

• Humming (Simple Bhramari Pranayama) as a Stress Buster: A Holter-Based Study to Analyze Heart Rate Variability (HRV) Parameters During Bhramari, Physical Activity, Emotional Stress, and Sleep: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10182780/

• 14-Minute Guided NSDR (non-sleep deep rest) practice: https://www.youtube.com/watch?v=vjXX2c72fYY

• Breathing Techniques to Reduce Stress and Anxiety | Dr. Andrew Huberman on the Physiological Sigh: https://www.youtube.com/watch?v=kSZKIupBUuc

• Interoception: the hidden sense that shapes well-being: https://www.theguardian.com/science/2021/aug/15/the-hidden-sense-shaping-your-wellbeing-interoception

• Exteroception: https://dictionary.apa.org/exteroception

• Interoceptive Awareness and ADHD: https://chadd.org/adhd-news/adhd-news-adults/interoceptive-awareness-and-adhd/

• Childhood Trauma Affects Stress-Related Interoceptive Accuracy: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6813623/

• The Hour Between Dog and Wolf: How Risk Taking Transforms Us, Body and Mind: https://www.amazon.com/Hour-Between-Dog-Wolf-Transforms/dp/0143123408

• Somatic Experiencing: https://www.somaticexperiencing.com/

• Hakomi Institute: https://hakomiinstitute.com/

• Decisions and Desire (about Antonio Damasio’s work): https://hbr.org/2006/01/decisions-and-desire

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

• What Is Yoga Nidra?: https://health.clevelandclinic.org/what-is-yoga-nidra

• Becoming Fully Yourself, What AI Wants, Family Rituals & Rites of Passage, with Kevin Kelly: https://podcast.curioushumans.com/episodes/becoming-fully-yourself-what-ai-wants-rites-of-passage-with-kevin-kelly

• Tim Ferriss: https://tim.blog/

• The Power of Sensations: Intermediate’s Vipassana Body Scan: https://insighttimer.com/carola.ananda/guided-meditations/the-power-of-sensations-intermediates-vipassana-body-scan-meditation

• Vipassana Meditation: https://www.dhamma.org/en/index

• The Body Keeps the Score: Brain, Mind, and Body in the Healing of Trauma: https://www.amazon.com/Body-Keeps-Score-Healing-Trauma/dp/0670785938

• Waking the Tiger: Healing Trauma: https://www.amazon.com/Waking-Tiger-Healing-Peter-Levine/dp/155643233X

• Consolations: The Solace, Nourishment and Underlying Meaning of Everyday Words: https://www.themarginalian.org/2015/04/29/david-whyte-consolations-words/

• The 15 Commitments of Conscious Leadership: A New Paradigm for Sustainable Success: https://www.amazon.com/15-Commitments-Conscious-Leadership-Sustainable/dp/0990976904/

• The Conscious Leadership Group: https://conscious.is/

• Recapture the Rapture: Rethinking God, Sex, and Death in a World That’s Lost Its Mind: https://www.amazon.com/Recapture-Rapture-Rethinking-Death-World/dp/0062905465

• Kubo and the Two Strings on Prime Video: https://www.amazon.com/Kubo-Two-Strings-Charlize-Theron/dp/B01K5BSWX0

• Wolfwalkers on AppleTV+: https://tv.apple.com/us/movie/wolfwalkers/umc.cmc.amuoq00hqelfi98j0gvg641x

• Scavengers Reign on Max: https://www.max.com/shows/scavengers-reign/50c8ce6d-088c-42d9-9147-d1b19b1289d4

• Jerry Colonna on LinkedIn: https://www.linkedin.com/in/jerry-colonna-reboot/

• Ra Optics “Sunset” blue-light blockers: https://raoptics.com/collections/night-lenses

• Nurosym vagal stimulation device: https://my.nurosym.com/vns1564/

• Pulsetto vagal stimulation device: https://pulsetto.tech/new-year/?gc_id=20124962116&h_ad_id=686249897188&gad_source=1

• Apollo vagus nerve stimulator: https://apolloneuro.com/products/apollo-wearable

—

Additional research:

• Cellular allostatic load is linked to increased energy expenditure and accelerated biological aging: https://www.sciencedirect.com/science/article/pii/S0306453023003001

• Somatic experiencing: using interoception and proprioception as core elements of trauma therapy: https://www.frontiersin.org/articles/10.3389/fpsyg.2015.00093/full

• Relationship between interoception and emotion regulation: New evidence from mixed methods: https://www.sciencedirect.com/science/article/abs/pii/S0165032718323723

• Out-of-the-blue panic attacks aren’t without warning: body sends signals for hour before: https://pubmed.ncbi.nlm.nih.gov/21783179/

—

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

—

Lenny may be an investor in the companies discussed.

Geoffrey Moore is an author, speaker, and advisor, widely known for his seminal book Crossing the Chasm: Marketing and Selling Disruptive Products to Mainstream Customers, which many consider the most important book ever written on go-to-market strategy. Moore’s work is focused on the market dynamics surrounding disruptive innovations, and how one overcomes the challenge of transitioning from serving early adopters to the mainstream. In this episode, we discuss:

• What “crossing the chasm” means

• What steps to take before you try crossing the chasm

• The importance of winning a marquee customer

• The role of executive sponsors in the sales process

• The differences between visionaries and pragmatists, and how to build for each

• Geoffrey’s four go-to-market playbooks based on stage: Early Market, Bowling Alley, Tornado, and Main Street

• The problem with discounting before crossing the chasm

• “Deadly sins” to avoid when crossing the chasm

—

Brought to you by:

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

• WorkOS—An API platform for quickly adding enterprise features

• Arcade Software—Create effortlessly beautiful demos in minutes

—

Find the full transcript at: https://www.lennyspodcast.com/geoffrey-moore-on-finding-your-beachhead-crossing-the-chasm-and-dominating-a-market/

—

Where to find Geoffrey Moore:

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

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

• LinkedIn posts: https://www.linkedin.com/in/geoffreyamoore/recent-activity/articles/

—

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) Geoffrey’s background

(04:03) What people often get wrong about Crossing the Chasm

(05:58) Finding your beachhead segment

(09:29) The four inflection points of the technology adoption lifestyle

(15:45) Geoffrey’s bonfire and bowling alley analogies

(18:36) Steps to take before trying to cross the chasm

(22:19) Signs you’re ready to cross the chasm

(25:19) Advice for startups on where to start

(27:31) Thoughts on venture capital

(27:53) A general timeline for crossing the chasm

(30:52) What exactly is the “chasm”?

(32:35) The difference between visionaries and pragmatists

(36:05) Finding the compelling reason to buy

(43:45) The Early Market playbook

(45:46) The Bowling Alley playbook

(48:39) Different sales approaches for early market and bowling alley

(51:26) Changing the value state of the company

(53:28) The Tornado playbook

(57:35) Why combining playbooks doesn’t work

(59:10) Using generative AI in different market phases

(01:03:02) The risks of discounting

(01:04:21) Other “deadly sins” of crossing the chasm

(01:09:09) Positioning in crossing the chasm

(01:10:36) Product-led growth and crossing the chasm

(01:13:54) The challenges of software and entrepreneurship

(01:16:35) How Geoffrey’s thinking has evolved

(01:19:30) The importance of entrepreneurship and impact

(01:20:42) His book The Infinite Staircase

(01:23:58) Connect with Geoffrey Moore

—

Referenced:

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

• Oracle: https://www.oracle.com/

• Documentum: https://www.opentext.com/products/documentum

• Figma: https://www.figma.com/

• Notion: https://www.notion.so/

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

• Intel: https://www.intel.com/

• Jason Fried challenges your thinking on fundraising, goals, growth, and more: https://www.lennyspodcast.com/jason-fried-challenges-your-thinking-on-fundraising-goals-growth-and-more/

• The Mayo Clinic: https://www.mayoclinic.org/

• Coda: https://coda.io/

• An inside look at how Figma ships product: https://coda.io/@yuhki/figma-product-roadmap

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

• Regis McKenna on Crunchbase: https://www.crunchbase.com/organization/regis-mckenna-inc

• Andrew Grove: https://en.wikipedia.org/wiki/Andrew_Grove

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

• Sales Pitch: How to Craft a Story to Stand Out and Win: https://www.amazon.com/Sales-Pitch-Craft-Story-Stand/dp/1999023021

• B2B Go-to-Market Playbooks and the Technology Adoption Life Cycle: https://www.linkedin.com/pulse/b2b-go-to-market-playbooks-technology-adoption-life-cycle-moore/

• Juniper: https://www.juniper.net/us/en.html

• Sal Khan on LinkedIn: https://www.linkedin.com/in/khanacademy/

• Khan Academy: https://www.khanacademy.org/

• How the Star Wars Kessel Run Turns Han Solo Into a Time-Traveler: https://www.wired.com/2013/02/kessel-run-12-parsecs/

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

• Martin Casado on LinkedIn: https://www.linkedin.com/in/martincasado/

• The Infinite Staircase: What the Universe Tells Us About Life, Ethics, and Mortality: https://www.amazon.com/Infinite-Staircase-Universe-Ethics-Mortality/dp/1950665984

—

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

—

Lenny may be an investor in the companies discussed.

Richard Rumelt is a legend in the world of strategy. He’s the author of Good Strategy/Bad Strategy and The Crux: How Leaders Become Strategists, both of which are often recommended by guests on this podcast. From his early days teaching in Iran at a Harvard-sponsored business school to teaching at Harvard Business School itself to over four decades teaching at UCLA’s Anderson School of Management, Richard’s impact resonates globally. His strategic insights are sought after by major corporations including Microsoft, Shell, Apple, AT&T, Intel, and Commonwealth Bank and by governmental organizations such as the U.S. Army Special Operations Command. In this episode, we discuss:

• The essential components of a good strategy

• The importance of coherence in strategy

• Common pitfalls that create a bad strategy

• How “power” plays into strategy, and common sources of power

• The value of knowing history when developing effective strategies

• Why a strategy should simply be called an “action agenda”

• The need for one decider in an organization

—

Brought to you by:

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

• Miro—A collaborative visual platform where your best work comes to life

• Vanta—Automate compliance. Simplify security.

—

Find the full transcript at: https://www.lennyspodcast.com/good-strategy-bad-strategy-richard-rumelt/

—

Where to find Richard Rumelt:

• Email: richard@generalimagination.com

• LinkedIn: https://www.linkedin.com/in/richard-rumelt-18520828/

• Website: https://thecruxbook.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) Richard’s background

(04:29) What is a strategy?

(06:23) The essential components of a good strategy (the “kernel”)

(15:04) An example of good strategy

(16:55) Bad strategy

(25:17) The importance of focus and power

(28:19) Identifying and utilizing power

(34:38) Types of power

(41:13) Implementing power

(48:15) The importance of historical knowledge

(55:23) How to write an action agenda

(01:02:47) The crux

(01:10:40) Challenges to executing a strategy

(01:15:44) The need for a decider

(01:20:39) Strategy for startups

(01:26:04) Richard’s “value denials” exercise

(01:31:01) Closing thoughts

(01:33:57) Lightning round

—

Referenced:

• China’s Xi says ‘reunification’ with Taiwan is inevitable: https://www.cnbc.com/2023/12/31/chinas-xi-says-reunification-with-taiwan-is-inevitable.html

• The Crux: How Leaders Become Strategists: https://www.amazon.com/Crux-How-Leaders-Become-Strategists/dp/1541701240

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

• Fundamental Issues in Strategy: A Research Agenda: https://www.amazon.com/Fundamental-Issues-Strategy-Research-Agenda/dp/0875843433/

• Strategy, Structure, and Economic Performance: https://www.amazon.com/Strategy-Structure-Economic-Performance-Richard/dp/0875841090

• There’s more than the CIA and FBI: The 17 agencies that make up the U.S. intelligence community: https://www.latimes.com/nation/la-na-17-intelligence-agencies-20170112-story.html

• Programme for International Student Assessment: https://www.oecd.org/pisa/

• Gerstner: Changing Culture at IBM—Lou Gerstner Discusses Changing the Culture at IBM: https://hbswk.hbs.edu/archive/gerstner-changing-culture-at-ibm-lou-gerstner-discusses-changing-the-culture-at-ibm

• Marvin Lieberman on LinkedIn: https://www.linkedin.com/in/marvin-lieberman-2a6b72/

• S&P 500: https://www.spglobal.com/spdji/en/indices/equity/sp-500/#overview

• Battle of Tora Bora: https://en.wikipedia.org/wiki/Battle_of_Tora_Bora

• Milton Friedman: https://en.wikipedia.org/wiki/Milton_Friedman

• The Louvre: https://www.louvre.fr/en

• How does SpaceX build its Falcon 9 reusable rocket?: https://www.sciencefocus.com/space/how-does-spacex-build-its-falcon-9-reusable-rocket

• Charles Darwin: History’s most famous biologist: https://www.nhm.ac.uk/discover/charles-darwin-most-famous-biologist.html

• Donald Rumsfeld: https://www.defense.gov/About/Biographies/Biography/Article/602800/

• Bush: The Decider-in-Chief: https://www.cbsnews.com/news/bush-the-decider-in-chief/

• Woodrow Wilson: https://www.whitehouse.gov/about-the-white-house/presidents/woodrow-wilson/

• How the Sinking of Lusitania Changed World War I: https://www.history.com/news/how-the-sinking-of-lusitania-changed-wwi

• Nokia: https://www.nokia.com/

• The Rise and Fall of Nokia: https://www.hbs.edu/faculty/Pages/item.aspx?num=46041

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

• These New Windows Let the Summer Breeze In, But Block the Street Noise: https://www.smithsonianmag.com/smart-news/these-new-windows-let-the-summer-breeze-in-but-block-the-street-noise-7906121/

• Stop it! (Bob Newhart): https://www.youtube.com/watch?v=jvujypVVBAY

• The Innovator’s Dilemma: The Revolutionary Book That Will Change the Way You Do Business: https://www.amazon.com/Innovators-Dilemma-Revolutionary-Change-Business/dp/0062060244

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

• Steve Jobs: https://www.amazon.com/Steve-Jobs-Walter-Isaacson/dp/1982176865

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

• Titan: The Life of John D. Rockefeller, Sr.: https://www.amazon.com/Titan-Life-John-Rockefeller-Sr/dp/1400077303/

• Yellowstone on Paramount+: https://www.paramountnetwork.com/shows/yellowstone

• Smart telescopes: https://milehighastro.com/collections/smart-telescopes

• Cassandra Clare: https://cassandraclare.com/

—

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

—

Lenny may be an investor in the companies discussed.

Heidi Helfand is the author of Dynamic Reteaming, which outlines practical strategies for orchestrating successful team and company org changes. Her work is informed by more than 20 years in the tech industry at notable companies like AppFolio, Procore, and Expertcity/GoToMeeting. Today, she dedicates her efforts to sharing her knowledge through workshops, comprehensive courses, and consultative services, helping organizations navigate and optimize their team structures. In this episode, we discuss:

• The importance of reteaming and reorging

• The benefits of embracing reteaming

• The five patterns of reteaming: one by one, grow and split, merging, isolation, and switching

• Examples of successful reteaming

• Why stable teams are not always ideal

• How change can lead to great career opportunities

• The RIDE framework for decision-making

• Advice on how to set up isolated teams for success

• The anti-patterns of reteaming and the challenges that can arise

• Tactical tips for becoming a better listener

—

Brought to you by:

• Productroadmap.ai—AI to connect your roadmaps to revenue

• Hex—Helping teams ask and answer data questions by working together

• Ahrefs—Improve your website’s SEO for free

—

Find the full transcript at: https://www.lennyspodcast.com/the-art-and-wisdom-of-changing-teams-heidi-helfand-author-of-dynamic-reteaming/

—

Where to find Heidi Helfand:

• X: https://twitter.com/heidihelfand

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

• Website: https://www.heidihelfand.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) Heidi’s background

(03:40) How Heidi got involved with reteaming and reorgs

(07:37) Advice for people dealing with reorgs

(11:56) The benefits of change and the RIDE framework

(17:11) The five patterns of reteaming

(20:00) The power of isolation

(27:38) Advice on how to be successful by isolating small teams

(33:27) Supporting and protecting internal startups

(34:33) The one-by-one pattern

(36:44) The grow and split pattern

(39:20) The merging pattern

(42:14) The switching pattern

(50:18) Anti-patterns of reteaming

(52:49) Embracing change and growth

(58:48) How to become a better listener

(01:01:28) Lightning round

—

Referenced:

• Dynamic Reteaming: The Art and Wisdom of Changing Teams: https://www.amazon.com/Dynamic-Reteaming-Wisdom-Changing-Teams/dp/1492061298

• O’Reilly: https://www.oreilly.com/

• Procore Technologies: https://www.procore.com/

• Kristian Lindwall on LinkedIn: https://www.linkedin.com/in/kristianlindwall/

• Chris Smith on LinkedIn: https://www.linkedin.com/in/chrissmithagile

• Transitions: Making Sense of Life’s Changes: https://www.amazon.com/Transitions-Making-Changes-Revised-Anniversary/dp/073820904X

• Pat Wadors on LinkedIn: https://www.linkedin.com/in/patwadors/

• The Four Steps to the Epiphany: Successful Strategies for Products That Win: https://www.amazon.com/Four-Steps-Epiphany-Successful-Strategies/dp/1119690358

• GoToMyPC: https://get.gotomypc.com/

• Teamwork: https://www.amazon.com/Teamwork-Right-Wrong-Interpersonal-Communication/dp/0803932901

• AppFolio: https://www.appfolio.com/

• SecureDocs: https://www.securedocs.com/

• Citrix: https://www.citrix.com/

• The Culture Code: The Secrets of Highly Successful Groups: https://www.amazon.com/Culture-Code-Secrets-Highly-Successful/dp/0804176981

• Tuckman’s stages of group development: https://en.wikipedia.org/wiki/Tuckman%27s_stages_of_group_development

• Rich Sheridan on LinkedIn: https://www.linkedin.com/in/menloprez/

 • Menlo Innovations: https://menloinnovations.com/

• Drive: The Surprising Truth About What Motivates Us: https://www.amazon.com/Drive-Surprising-Truth-About-Motivates/dp/1594484805

• Toyota Kata: Managing People for Improvement, Adaptiveness and Superior Results: https://www.amazon.com/Toyota-Kata-Managing-Improvement-Adaptiveness/dp/0071635238

• Paulo Freire: https://en.wikipedia.org/wiki/Paulo_Freire

• Jon Walker on LinkedIn: https://www.linkedin.com/in/jwalker/

• Managing Corporate Lifecycles: https://www.amazon.com/Managing-Corporate-Lifecycles-Ichak-Adizes/dp/9381860548

• The Adizes Institute: https://www.adizes.com/

• John Cutler on Lenny’s Podcast: https://www.lennyspodcast.com/what-differentiates-the-highest-performing-product-teams-john-cutler-amplitude-the-beautiful-mes/

• Co-Active Training Institute: https://coactive.com/

• Co-Active Coaching: The proven framework for transformative conversations at work and in life: https://www.amazon.com/Co-Active-Coaching-Fourth-transformative-conversations/dp/1473674980

• Creating Intelligent Teams: https://www.amazon.com/Creating-Intelligent-teams-Anne-R%C3%B8d/dp/186922583X

• The Surprising Power of Liberating Structures: Simple Rules to Unleash a Culture of Innovation: https://www.amazon.com/Surprising-Power-Liberating-Structures-Innovation/dp/0615975305

• Facilitator’s Guide to Participatory Decision-Making: https://www.amazon.com/Facilitators-Participatory-Decision-Making-Jossey-bass-Management/dp/1118404955

• The Bear on Hulu: https://www.hulu.com/series/the-bear-05eb6a8e-90ed-4947-8c0b-e6536cbddd5f

—

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

—

Lenny may be an investor in the companies discussed.

Ethan Evans is a writer, career coach, course instructor, and retired VP at Amazon. During his 15 years at Amazon, he helped invent Prime Video, Amazon Video, the Amazon Appstore, Prime Gaming (formerly Twitch Prime), and Twitch Commerce. Prior to Amazon, Ethan spent 12 years in technical leadership roles at several East Coast startups. He writes a newsletter, Level Up, which publishes candid career advice and has a growing community of ambitious professionals to connect with. Ethan also offers a range of Leadership Development Courses via live online classes and on-demand courses. In this episode, we discuss:

• The Magic Loop framework: a five-step process to grow your career

• A handful of reasons why people get stuck in their career growth

• Advice on how to break out of a career plateau

• How to cultivate inventiveness in your work

• How to stand out in interviews

• A personal story of failing Jeff Bezos and lessons learned

• Contrarian opinions on the return-to-office movement and doing business on a handshake

—

Brought to you by Sidebar—Accelerate your career by surrounding yourself with extraordinary peers | Sprig—Build a product people love | Arcade Software—Create effortlessly beautiful demos in minutes

—

Find the full transcript at: https://www.lennyspodcast.com/taking-control-of-your-career-ethan-evans-amazon/

—

Where to find Ethan Evans:

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

• Substack: https://levelupwithethanevans.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) Ethan’s background

(04:25) The Magic Loop

(08:31) The goal of the Magic Loop

(10:59) Clarifications on the framework

(12:46) Success stories

(17:22) The importance and effectiveness of the Magic Loop

(19:01) A quick summary of the steps in the Magic Loop

(21:46) What if you’re not pursuing a promotion?

(23:09) How to break out of a career plateau

(28:52) How to become systematically inventive

(36:04) Interview advice and how to stand out

(40:43) A story of failing Jeff Bezos

(50:31) Lessons learned from that failure

(57:30) What Ethan would have done differently

(01:00:35) Amazon’s leadership principles

(01:08:52) Contrarian corner: Returning to the office vs. staying remote

(01:10:39) Contrarian corner: Doing business on a handshake

(01:11:52) Lightning round

—

Referenced:

• The Magic Loop: https://www.lennysnewsletter.com/p/the-magic-loop

• SDE levels: https://www.masaischool.com/blog/understanding-sde-levels-sde-1-vs-sde-2-vs-sde-3-differences/

• 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

• Thomas Edison’s quote: https://www.brainyquote.com/quotes/thomas_a_edison_109928

• Jeff Bezos: Amazon and Blue Origin | Lex Fridman Podcast: https://www.youtube.com/watch?v=DcWqzZ3I2cY

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

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

• Jeff Wilke on X: https://twitter.com/jeffawilke

• Andy Jassy on LinkedIn: https://www.linkedin.com/in/andy-jassy-8b1615/

• Werner Vogels on LinkedIn: https://www.linkedin.com/in/wernervogels/

• Amazon’s Silk browser explained: https://www.androidpolice.com/amazon-silk-browser-explainer/

• Chickens and pigs: https://www.scrum.org/resources/chickens-and-pigs

• 58% of tech employees experience imposter syndrome. Here’s how to overcome it: https://medium.com/wearefutureworks/58-of-tech-employees-experience-imposter-syndrome-heres-how-to-overcome-it-78172d8a2258

• Jeff Bezos to exec after product totally flopped: ‘You can’t, for one minute, feel bad’: https://www.cnbc.com/2020/05/22/jeff-bezos-why-you-cant-feel-bad-about-failure.html

• Amazon’s leadership principles: https://www.amazon.jobs/content/en/our-workplace/leadership-principles

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

• Decisive: How to Make Better Choices in Life and Work: https://www.amazon.com/Decisive-Make-Better-Choices-Life/dp/0307956393

• Leadership and Self-Deception: Getting Out of the Box: https://www.amazon.com/Leadership-Self-Deception-Getting-Out-Box/dp/1523097809

• The Almanack of Naval Ravikant: A Guide to Wealth and Happiness: https://www.amazon.com/Almanack-Naval-Ravikant-Wealth-Happiness/dp/1544514212/

• Angel list: https://venture.angellist.com/naval/syndicate

• Naval Ravikant on X: https://twitter.com/naval

• 1923 on Paramount+: https://www.paramountplus.com/shows/1923/

• Yellowstone on Paramount+: https://www.paramountnetwork.com/shows/yellowstone

• Chuckit! dog toys: https://www.chuckit-toys.co.uk/

• Luke 12:48: https://law.utk.edu/2016/05/10/to-whom-much-is-given-much-will-be-required

• The Challenger space shuttle disaster: https://en.wikipedia.org/wiki/Space_Shuttle_Challenger_disaster

• Ethan’s popular course on Maven: https://maven.com/ethan-evans/break-through-to-executive

—

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

—

Lenny may be an investor in the companies discussed.

Sam Schillace is deputy CTO and corporate vice president at Microsoft. Prior to working at Microsoft, Sam started a company called Writely, which was acquired by Google and became the foundation of what today is Google Docs. While at Google, Sam helped lead many of Google’s consumer products, including Gmail, Blogger, PageCreator, Picasa, Reader, Groups, and more recently Maps and Google Automotive Services. Sam was also a principal investor at Google Ventures, has founded six startups, and was the SVP of engineering at Box through their IPO. In this episode, we discuss:

• The journey of building Google Docs

• The importance of taking risks, embracing failure, and finding joy in your work

• The importance of asking “what if” questions vs. “why not”

• Why convenience always wins

• How, and why, Sam stays optimistic

• Inside Microsoft’s culture

• Why you should solve problems without asking for permission

• Early-career advice

• Why “pixels are free” and “bots are docs”

—

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—

Find the full transcript at: https://www.lennyspodcast.com/how-to-be-more-innovative-sam-schillace-microsoft-deputy-cto-creator-of-google-docs/

—

Where to find Sam Schillace:

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

• Newsletter: https://sundaylettersfromsam.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) Sam’s background

(03:45) The first Google Docs file

(06:45) Disruptive innovation

(10:11) First-principles thinking

(11:00) Recognizing disruptive ideas

(13:17) Examples of first-principles thinking

(15:46) The power of optimism

(19:47) Sam’s motto: Get to the edge of something and f**k around

(21:53) User value and laziness

(24:31) People are lazy (and what to do about it)

(28:36) Building Google Docs

(31:06) The evolution of Google Docs

(37:15) Finding product-market fit

(39:52) The future of documents

(44:57) The value of playing with technology

(47:58) Taking risks and embracing failure

(49:21) Thinking in the future

(53:48) Finding joy in your work

(01:01:20) Just do the best you can

(01:02:34) The transformational power of AI

(01:09:27) Advice for approaching AI

(01:13:07) The culture at Microsoft

(01:16:51) Closing thoughts

(01:17:32) Lightning round

—

Referenced:

• Google Docs began as a hacked-together experiment, says creator: https://www.theverge.com/2013/7/3/4484000/sam-schillace-interview-google-docs-creator-box

• Edna Mode: https://disney.fandom.com/wiki/Edna_Mode

• Sergey Brin’s profile on Forbes: https://www.forbes.com/profile/sergey-brin/

• People Who Were No Smarter Than You: https://medium.com/thrive-global/people-who-were-no-smarter-than-you-4e1c88c3fee6

• Nat Torkington (O’Reilly Media): https://www.oreilly.com/people/nathan-torkington/

• How Tesla Has Shaken (Not Stirred) Established Carmakers—and Why It Really Matters: https://www.forbes.com/sites/jenniferdungs/2021/04/23/how-tesla-has-shaken-not-stirred-established-carmakersand-why-it-really-matters/

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

• Ashton Tate: https://en.wikipedia.org/wiki/Ashton-Tate

• Learning by Doing: https://www.linkedin.com/pulse/learning-doing-sam-schillace

• Kevin Scott on LinkedIn: https://www.linkedin.com/in/jkevinscott/

• How do we make sense of all of this?: https://sundaylettersfromsam.substack.com/p/how-do-we-make-sense-of-all-of-this

• Steve Newman on LinkedIn: https://www.linkedin.com/in/stevescalyr/

• Eric Schmidt on LinkedIn: https://www.linkedin.com/in/eric-schmidt-02158951/

• Michael Arrington on X: https://twitter.com/arrington

• TechCrunch: https://techcrunch.com/

• “Hello, Computer” scene from Star Trek: https://www.youtube.com/watch?v=hShY6xZWVGE

• Writely—Process Words with your Browser: https://techcrunch.com/2005/08/31/writely-process-words-with-your-browser/

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

• Poor Charlie’s Almanack: The Essential Wit and Wisdom of Charles T. Munger: https://press.stripe.com/poor-charlies-almanack

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

• This Quote from Seth Godin Could Change How You Think About Pursuing Your Passion: https://friedchickenandsushi.com/blog/2021/7/5/this-quote-from-seth-godin-could-change-how-you-think-about-pursuing-your-passion

• AI isn’t a feature of your product: https://sundaylettersfromsam.substack.com/p/ai-isnt-a-feature-of-your-product

• Introducing Gemini: our largest and most capable AI model: https://blog.google/technology/ai/google-gemini-ai/

• Invisible Cities: https://www.amazon.com/Invisible-Cities-Italo-Calvino/dp/0156453800

• The Wasp Factory: https://www.amazon.com/WASP-FACTORY-NOVEL-Iain-Banks/dp/0684853159

• Where Good Ideas Come From: The Natural History of Innovation: https://www.amazon.com/Where-Good-Ideas-Come-Innovation/dp/1594485380/

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

• Monarch: Legacy of Monsters on Apple TV+: https://tv.apple.com/us/show/monarch-legacy-of-monsters/umc.cmc.62l8x0ixrhyq3yaqa5y8yo7ew?mttn3pid

• Scavengers Reign on Max: https://www.max.com/shows/scavengers-reign/50c8ce6d-088c-42d9-9147-d1b19b1289d4

• 2023 Mustang Mach-E: https://www.ford.com/suvs/mach-e/

• Boccalone Salumeria (now closed) on X: https://twitter.com/boccalone

—

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

—

Lenny may be an investor in the companies discussed.

Will Larson is Chief Technology Officer at Carta. Prior to joining Carta, he was the CTO at Calm and held engineering leadership roles at Stripe, Uber, and Digg. He is the author of two foundational engineering career books, An Elegant Puzzle and Staff Engineer, and The Engineering Executive’s Primer, which will be released in February. In our conversation, we discuss:

• Systems thinking: what it is and how to apply it

• Advice for product managers on fostering productive relationships with engineering managers

• Why companies should treat engineers like adults

• How to best measure developer productivity

• Writing and its impact on his career

• How to balance writing with a demanding job

• How to develop your company values

—

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—

Find the full transcript at: https://www.lennyspodcast.com/the-engineering-mindset-will-larson-carta-stripe-uber-calm-digg/

—

Where to find Will Larson:

• X: https://twitter.com/Lethain

• LinkedIn: https://www.linkedin.com/in/will-larson-a44b543/

• Website: https://lethain.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) Will’s background

(04:12) Changes in the field of engineering

(06:27) We need to stop treating engineers like children

(08:32) Systems thinking

(13:23) Implementing systems thinking in hiring

(16:32) Engineering strategy

(20:21) Examples of engineering strategies

(25:08) How to get good at strategy

(26:48) The importance of writing about things that excite you

(32:40) The biggest risk to content creation is quitting too soon

(35:24) How to make time for writing

(37:41) Tips for aspiring writers

(41:18) Building productive relationships between product managers and engineers

(43:45) Giving the same performance rating to EMs and PMs

(48:24) Measuring engineering productivity

(55:53) Defining company values

(01:02:10) Failure corner: the Digg rewrite

(01:11:05) Will’s upcoming book, The Engineering Executive’s Primer

(01:12:04) Lightning round

—

Referenced:

• The end of the “free money” era: https://www.theguardian.com/technology/2023/apr/11/techscape-zirp-tech-boom

• Work on what matters: https://lethain.com/work-on-what-matters/

• Sheryl Sandberg to Harvard Biz Grads: “Find a Rocket Ship”: https://www.forbes.com/sites/kashmirhill/2012/05/24/sheryl-sandberg-to-harvard-biz-grads-find-a-rocket-ship/?sh=708c9a93b37a

• What Is Systems Thinking?: https://www.snhu.edu/about-us/newsroom/business/what-is-systems-thinking

• Introduction to systems thinking: https://lethain.com/systems-thinking/

• Thinking in Systems: https://www.amazon.com/Thinking-Systems-Donella-H-Meadows/dp/1603580557

• Silent Spring: https://www.amazon.com/Silent-Spring-Rachel-Carson/dp/0618249060

• Writing an engineering strategy: https://lethain.com/eng-strategies/

• Carta: https://carta.com/

• Eric Vogl on LinkedIn: https://www.linkedin.com/in/ericvogl/

• Good Strategy/Bad Strategy: The difference and why it matters: https://www.amazon.com/Good-Strategy-Bad-difference-matters/dp/1781256179

• The Crux: How Leaders Become Strategists: https://www.amazon.com/Crux-How-Leaders-Become-Strategists/dp/1541701240/

• How Big Things Get Done: The Surprising Factors That Determine the Fate of Every Project, from Home Renovations to Space Exploration and Everything in Between: https://www.amazon.com/How-Big-Things-Get-Done/dp/0593239512/

• Technology Strategy Patterns: Architecture as Strategy: https://www.amazon.com/Technology-Strategy-Patterns-Architecture/dp/1492040878/

• The Value Flywheel Effect: Power the Future and Accelerate Your Organization to the Modern Cloud: https://www.amazon.com/Value-Flywheel-Effect-Accelerate-Organization/dp/1950508579

• The Phoenix Project: A Novel about IT, DevOps, and Helping Your Business Win: https://www.amazon.com/Phoenix-Project-DevOps-Helping-Business/dp/1942788290

• The Engineering Executive’s Primer: Impactful Technical Leadership: https://www.amazon.com/Engineering-Executives-Primer-Impactful-Leadership/dp/1098149483

• An Elegant Puzzle: Systems of Engineering Management: https://press.stripe.com/an-elegant-puzzle

• Staff Engineer: Leadership beyond the management track: https://www.amazon.com/Staff-Engineer-Leadership-beyond-management-ebook/dp/B08RMSHYGG

• Gergely Orosz’s newsletter: https://blog.pragmaticengineer.com/author/gergely/

• Leaving big tech to build the #1 technology newsletter | Gergely Orosz (The Pragmatic Engineer): https://www.lennyspodcast.com/videos/leaving-big-tech-to-build-the-1-technology-newsletter-gergely-orosz-the-pragmatic-engineer/

• The art of product management | Shreyas Doshi (Stripe, Twitter, Google, Yahoo): https://www.lennyspodcast.com/videos/the-art-of-product-management-shreyas-doshi-stripe-twitter-google-yahoo/

• Henry Ward on LinkedIn: https://www.linkedin.com/in/heward/

• Vrushali Paunikar on LinkedIn: https://www.linkedin.com/in/vrushali-paunikar/

• Accelerate: The Science of Lean Software and DevOps: Building and Scaling High Performing Technology Organizations: https://www.amazon.com/Accelerate-Software-Performing-Technology-Organizations/dp/1942788339

• How to measure and improve developer productivity | Nicole Forsgren (Microsoft Research, GitHub, Google): https://www.lennyspodcast.com/how-to-measure-and-improve-developer-productivity-nicole-forsgren-microsoft-research-github-goo/

• DORA: https://dora.dev/

• Setting engineering org values: https://lethain.com/setting-engineering-org-values/

• Digg: https://digg.com/

• Kevin Rose on LinkedIn: https://www.linkedin.com/in/kevinrose/

• Digg’s v4 launch: an optimism born of necessity: https://lethain.com/digg-v4/

• Dash Gopinath on LinkedIn: https://www.linkedin.com/in/dashgopinath/

• Rich Schumacher on LinkedIn: https://www.linkedin.com/in/richschumacher/

• The ALL NEW Don’t Think of an Elephant!: Know Your Values and Frame the Debate: https://www.amazon.com/ALL-NEW-Dont-Think-Elephant-ebook/dp/B00NP9LHFA

• Top Chef on Peacock: https://www.peacocktv.com/watch-online/tv/top-chef/5172289448907967112

• Hard to work with: https://lethain.com/hard-to-work-with/

—

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

—

Lenny may be an investor in the companies discussed.

Judd Antin has spent 15 years leading research and design teams at companies like Yahoo, Meta, and Airbnb. His direct reports have gone on to lead user research at Figma, Notion, Slack, Robinhood, Duolingo, AllTrails, and more. In our conversation, we unpack the transformation that the user-research field is experiencing. Specifically:

• Where user research went wrong over the past decade

• The three types of research—macro, middle-range, and micro—and the purpose of each

• How to effectively integrate researchers into the product development process

• The “user-centered performance” phenomenon and why it’s a waste of time

• Common tropes about PMs, from researchers

• The ideal ratio of researchers in a company

• Why Judd says NPS is useless, and what to use instead

—

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—

Find the full transcript at: https://www.lennyspodcast.com/the-ux-research-reckoning-is-here-judd-antin-airbnb-meta/

—

Where to find Judd Antin:

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

• Website: https://juddantin.com/

• Blog: https://medium.com/onebigthought

—

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) Judd’s background

(04:16) Critiques and responses to Judd’s post “The UX Research Reckoning Is Here”

(07:33) The state of user research

(08:53) Macro, middle-range, and micro research

(14:05) What teams get wrong when it comes to research

(15:46) The importance of integrating research from the beginning

(17:30) Traits of great researchers

(19:53) Advice for evaluating user researchers

(21:10) Balancing business and product focus

(23:55) User-centered performance

(26:42) The role of intuition in product development

(30:15) Checking your gut instincts

(32:54) Common tropes about PMs, from researchers

(41:02) A/B testing vs. user research

(43:15) Hindsight bias and narrative fallacy

(44:55) Making recommendations based on research

(47:26) Advice for teams on how to leverage researchers

(51:18) How product managers can be better partners to user researchers

(56:53) The ideal ratio of researchers in a company

(59:43) Empowering user researchers to drive impact

(01:03:39) The limitations of NPS as a metric

(01:06:48) The risks of dogfooding

(01:08:51) Lightning round

—

Referenced:

• Matt Gallivan on LinkedIn: https://www.linkedin.com/in/mattgallivan/

• Janna Bray on LinkedIn: https://www.linkedin.com/in/janna-bray-a4046a25/

• Celeste Ridlen on LinkedIn: https://www.linkedin.com/in/celesteridlen/

• Rebecca Gray on LinkedIn: https://www.linkedin.com/in/rebeccagray2/

• Hannah Pileggi on LinkedIn: https://www.linkedin.com/in/hannah-pileggi-43169314/

• Louise Beryl on LinkedIn: https://www.linkedin.com/in/louise-beryl-13225833/

• The UX Research Reckoning Is Here: https://medium.com/onebigthought/the-ux-research-reckoning-is-here-c63710ea4084

• The end of the “free money” era: https://www.theguardian.com/technology/2023/apr/11/techscape-zirp-tech-boom

• Cognitive biases: https://en.wikipedia.org/wiki/List_of_cognitive_biases

• IDEO design thinking: https://designthinking.ideo.com/

• Everything Is Obvious: How Common Sense Fails Us: https://www.amazon.com/Everything-Obvious-Common-Sense-Fails/dp/0307951790

• Patrick Collison’s tweet: https://twitter.com/patrickc/status/1443215022029619200?lang=en

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

• Brian Chesky on Lenny’s Podcast: https://www.lennyspodcast.com/brian-cheskys-new-playbook/

• NPS: https://en.wikipedia.org/wiki/Net_promoter_score

• What is CSAT and how do you measure it?: https://www.qualtrics.com/experience-management/customer/what-is-csat/

• Michael Murakami on LinkedIn: https://www.linkedin.com/in/michaelhmurakami/

• Bad Leadership: What It Is, How It Happens, Why It Matters: https://www.amazon.com/Bad-Leadership-Happens-Matters-Common/dp/1591391660

• Demon Copperhead: https://www.amazon.com/Demon-Copperhead-Novel-Barbara-Kingsolver/dp/0063251922

• All Systems Red: The Murderbot Diaries: https://www.amazon.com/All-Systems-Red-Murderbot-Diaries/dp/0765397536

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

• Belay glasses: https://www.amazon.com/Belay-Glasses-Climbing-Comfortable-Sturdy/dp/B08GSBYDKQ/

• Epictetus: Control What You Can—Especially Yourself: https://www.shortform.com/blog/epictetus-control/

• The 7 Habits of Highly Effective People: Powerful Lessons in Personal Change: https://www.amazon.com/Habits-Highly-Effective-People-Powerful/dp/0743269519

—

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

—

Lenny may be an investor in the companies discussed.

Nir Eyal is the author of two best-selling books, Hooked: How to Build Habit-Forming Products and Indistractable: How to Control Your Attention and Choose Your Life. He writes, consults, and teaches at the intersection of psychology, technology, and business. His books have sold over 1 million copies in more than 30 languages; he has taught at Stanford’s Graduate School of Business and its Design School; and he has started and sold two startups since 2003. In our conversation, we discuss:

• Strategies for becoming less distractible and improving focus

• The difference between distraction and “traction”

• Reactive work vs. reflexive work and why you should book time in your calendar

• The 10-minute rule to overcome internal triggers and stay focused

• The problem with to-do lists, and what to do instead

• The value of creating a timebox schedule that aligns with personal values and priorities

• The use of pacts as a last line of defense against distraction

• How to develop a high-agency mindset

• Advice for leaders on helping employees improve focus in the workplace

—

Brought to you by Vanta—Automate compliance. Simplify security | Jira Product Discovery—Atlassian’s new prioritization and roadmapping tool built for product teams | Teal—Your personal career growth platform

—

Find the full transcript at: https://www.lennyspodcast.com/strategies-for-becoming-less-distracted-and-improving-focus-nir-eyal-author-of-indistractable-and/

—

Where to find Nir Eyal:

• X: https://twitter.com/nireyal

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

• Website: https://www.nirandfar.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) Nir’s background

(04:20) How to become less distractible

(07:43) Understanding distraction and traction

(12:52) The four steps to becoming indistractable

(13:53) Mastering internal triggers

(18:49) Surfing the urge with a 10-minute timer

(23:20) Making time for traction with a timebox schedule

(25:02) How to turn your values into time

(28:36) Booking deep work time

(29:22) Making pacts to prevent distraction

(31:00) The problem with to-do lists

(34:31) The drawback of deadlines

(36:08) Distraction is an emotion regulation problem

(39:54) Hacking back external triggers

(45:03) Preventing distraction with pacts

(48:18) Specific tools to hold you accountable

(53:42) Managing emotions and discomfort

(56:37) Taking responsibility and being high-agency

(01:00:09) Becoming indistractable at work

(01:05:04) Schedule syncing to align with managers

(01:09:36) We are not as hooked on technology as people think

(01:16:00) Life purpose and personal responsibility

(01:17:38) Lightning round

—

Referenced:

• Indistractable: How to Control Your Attention and Choose Your Life: https://www.amazon.com/Indistractable-Control-Your-Attention-Choose/dp/194883653X

• Hooked: How to Build Habit-Forming Products: https://www.amazon.com/Hooked-How-Build-Habit-Forming-Products/dp/1591847788

• Dorothy Parker’s quote: https://twitter.com/nireyal/status/1472280598723108866

• “Writing is bleeding” quote: https://www.hemingwaysociety.org/quotation-controversy-writing-and-bleeding

• The Pomodoro Technique Explained: https://www.forbes.com/sites/bryancollinseurope/2020/03/03/the-pomodoro-technique/

• Timeboxing: Why It Works and How to Get Started in 2024: https://www.nirandfar.com/timeboxing/

• Using your working time well - Issue 22: https://www.lennysnewsletter.com/p/time-management-issue-22

• All-In podcast: https://www.allinpodcast.co/

• Nir’s post about “the planning fallacy”: https://www.linkedin.com/posts/nireyal_why-do-tasks-always-seem-to-take-longer-than-activity-7137440438939959297-XIUB/

• How the Ancient Greeks Beat Distraction: https://www.nirandfar.com/tantalizing-distractions/

• Jeremy Bentham: https://iep.utm.edu/jeremy-bentham

• An overview of Sigmund Freud’s pleasure principle: https://www.sciencedirect.com/topics/nursing-and-health-professions/pleasure-principle

• The Matrix “There is no spoon” scene: https://www.youtube.com/watch?v=uAXtO5dMqEI

• Outlet timer: https://www.amazon.com/Century-Indoor-24-Hour-Mechanical-Outlet/dp/B01LPSGBZS

• Forest app: https://www.forestapp.cc/

• Focusmate: https://www.focusmate.com/

• Have We Been Thinking About Willpower the Wrong Way for 30 Years?: https://hbr.org/2016/11/have-we-been-thinking-about-willpower-the-wrong-way-for-30-years

• We Need Social Antibodies to Fight the Disease of Distraction: https://nireyal.medium.com/we-need-social-antibodies-to-fight-the-disease-of-distraction-51f9187be016

• The Mere Presence of Your Smartphone Reduces Brain Power, Study Shows: https://news.utexas.edu/2017/06/26/the-mere-presence-of-your-smartphone-reduces-brain-power

• Leading in Tough Times: HBS Faculty Member Amy C. Edmondson on Psychological Safety: https://www.hbs.edu/recruiting/insights-and-advice/blog/post/leading-in-tough-times

• If Tech Is So Distracting, How Do Slack Employees Stay So Focused?: https://www.nirandfar.com/slack-use/

• Managing up: https://www.lennysnewsletter.com/p/managing-up

• Duolingo: https://www.duolingo.com/

• FitBot: https://www.fitbotapp.com/

• Paulo Coelho’s quote: https://twitter.com/paulocoelho/status/416264984188825600

• 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

• The Experience Machine: How Our Minds Predict and Shape Reality: https://www.amazon.com/Experience-Machine-Minds-Predict-Reality/dp/1524748455

• Empire of the Sun on Prime Video: https://www.amazon.com/Empire-Sun-Christian-Bale/dp/B001N3JY82

• Sesame grinder: https://www.miyacompany.com/450-014-450-014

• Muji pens: https://www.muji.us/collections/pen-pencils

—

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

—

Lenny may be an investor in the companies discussed.

Sarah Tavel is a General Partner at Benchmark and sits on the boards of Chainalysis, Hipcamp, Rekki, Cambly, and Medely. She is a founding member of All Raise, the nonprofit organization working to accelerate the success of women in the venture-capital and VC-backed startup ecosystem. Before Benchmark, Sarah was a partner at Greylock Partners. She joined Pinterest in 2012 as their first PM and launched their first search and recommendations features. She also led three acquisitions as she helped the company scale through a period of hypergrowth. In this episode, we discuss:

Sarah’s Hierarchy of Engagement framework for growing a consumer startup

• The three levels of the Hierarchy of Engagement: core action, retention, and self-perpetuation

• The importance of measuring cohorts and maintaining focus on the core action

• Examples of core user actions from Pinterest and YouTube

Sarah’s Hierarchy of Marketplaces framework for building a marketplace startup

• The three vectors of growth for dominating a marketplace

• Advice on “tipping the marketplace” and ultimately dominating the market

• The value of focusing on a constrained market

• How to avoid disruption

—

This entire episode is brought to you by Gelt—Redefine your approach to taxes.

—

Find the full transcript at: https://www.lennyspodcast.com/the-hierarchy-of-engagement-sarah-tavel-benchmark-greylock-pinterest/

—

Where to find Sarah Tavel:

• X: https://twitter.com/sarahtavel

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

• Substack: https://www.sarahtavel.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) Sarah’s background

(03:33) Framework 1: The Hierarchy of Engagement

(06:03) Level 1: Core action

(10:33) Level 2: Retention

(14:00) Level 3: Self-perpetuation

(19:32) The importance of focus

(23:54) The challenge of anonymity

(26:04) Advice for founders who want to increase retention

(29:34) What founders often get wrong

(31:43) Examples of core actions

(37:37) Finding your North Star Metric

(38:12) Who should use the Hierarchy of Engagement framework

(38:54) The Hierarchy of Marketplaces framework

(46:09) Level 1: Focus on a constrained opportunity

(50:19) Sarah’s “happy GMV” and “minimum viable happiness” concepts

(54:47) Thumbtack: a counterexample to this approach

(56:36) Signs you’re ready to move to level 2

(58:06) Level 2: Tipping the marketplace

(01:04:15) Tipping loops

(01:10:53) Not all markets are susceptible to tipping

(01:15:55) The challenge of homogeneity in B2B marketplaces

(01:20:29) Signs you’re tipping successfully

(01:21:43) Level 3: Dominating the market

(01:28:29) The opportunity in underestimated markets

(01:30:11) The challenges of chasing GMV and losing focus

(01:36:36) Recognizing currents and momentum in the market

(01:39:20) You can never rest on your laurels

(01:41:03) How to apply these frameworks outside of marketplaces

(01:42:57) Three ways to find marketplace opportunity

(01:45:10 ) Lightning round

—

Referenced:

• Hierarchy of Engagement, Expanded: https://sarahtavel.medium.com/the-hierarchy-of-engagement-expanded-648329d60804

• Pinterest: https://www.pinterest.com/

• Evernote: https://evernote.com/

• Notion: https://www.notion.so/

• Houseparty app: https://en.wikipedia.org/wiki/Houseparty_(app)

• Clubhouse: https://www.clubhouse.com/

• How to price your product | Naomi Ionita (Menlo Ventures): https://www.lennyspodcast.com/how-to-price-your-product-naomi-ionita-menlo-ventures/

• TikTok: https://www.tiktok.com/

• Lessons on building a viral consumer app: The story of Saturn: https://www.lennysnewsletter.com/p/lessons-on-building-a-viral-consumer

• Saturn: https://www.joinsaturn.com/

• What happened to Secret?: https://www.failory.com/cemetery/secret

• How to determine your activation metric: https://www.lennysnewsletter.com/p/how-to-determine-your-activation

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

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

• Engagement Hierarchy: Core Actions: https://sarahtavel.medium.com/engagement-hierarchy-core-actions-dd4f72042100

• Choosing Your North Star Metric: https://www.lennysnewsletter.com/p/choosing-your-north-star-metric

• Hierarchy of Marketplaces: https://sarahtavel.medium.com/the-hierarchy-of-marketplaces-introduction-and-level-1-983995aa218e

• Mike Williams on LinkedIn: https://www.linkedin.com/in/yoroomie/

• Everything Marketplaces: https://www.everythingmarketplaces.com/

• Fabrice Grinda on LinkedIn: https://www.linkedin.com/in/fabricegrinda/

• OLX: https://www.olx.com/

• DoorDash Loves the ’Burbs as Much as You Do: https://www.wsj.com/articles/doordash-loves-the-burbs-as-much-as-you-do-11605618001

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

• NPS: https://en.wikipedia.org/wiki/Net_promoter_score

• Sean Ellis on LinkedIn: https://www.linkedin.com/in/seanellis/

• Rekki: https://rekki.com/

• Ronen Givon on LinkedIn: https://www.linkedin.com/in/ronen-givon-535b2514

• Hipcamp: https://www.hipcamp.com/

• Demand driving supply: The little-understood growth loop behind a surprising number of iconic billion-dollar companies: https://www.lennysnewsletter.com/p/demand-driving-supply-marketplaces

• Inside the Revolution at Etsy: https://www.nytimes.com/2017/11/25/business/etsy-josh-silverman.html

• Faire: https://www.faire.com/

• Bill Gurley on LinkedIn: https://www.linkedin.com/in/billgurley/

• Mechanical Turk: https://www.mturk.com/

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

• Rippling: https://www.rippling.com/

• “White Space” for Building a Marketplace: How to Find Your Competition’s Vulnerabilities—and Capitalize: https://sarahtavel.medium.com/white-space-for-building-a-marketplace-how-to-find-your-competitions-vulnerabilities-and-79674aa4d399

• Pachinko: https://www.amazon.com/Pachinko-National-Book-Award-Finalist/dp/1455563935

• The Five Temptations of a CEO: https://www.amazon.com/Five-Temptations-CEO-Anniversary-Leadership/dp/0470267585

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

• Tesla: https://www.tesla.com/

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

• What Is A Good Activation Rate: https://www.lennysnewsletter.com/p/what-is-a-good-activation-rate

—

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

—

Lenny may be an investor in the companies discussed.

Christian Idiodi is a partner at Silicon Valley Product Group. After a long product career and founding multiple companies, Christian now spends his time working closely with product leaders at companies big and small to implement and improve their discipline of product management. In today’s episode, we discuss:

• Why there’s often a negative perception of product managers, and how we can fix this

• The four attributes of a product manager’s job: value, usability, viability, and feasibility

• The power of finding reference customers

• How Christian developed a process for high-volume hiring to help companies like McDonald’s and Starbucks

• Tactical tips for coaching, building relationships, and building trust as a leader

—

Brought to you by Jira Product Discovery—Atlassian’s new prioritization and roadmapping tool built for product teams | Vanta—Automate compliance. Simplify security | Teal—Your personal career growth platform

—

Find the full transcript at: https://www.lennyspodcast.com/the-essence-of-product-management-christian-idiodi-svpg/

—

Where to find Christian Idiodi:

• X: https://twitter.com/CIdiodi

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

• Website: https://www.svpg.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) Christian’s background

(03:56) The negative perception of product managers

(07:58) How to become a PM people want to work with

(11:30) The definition of a product manager

(14:46) Where new PMs fail

(16:59) Reference customers: what they are and why they are so important

(24:05) A quick summary of how to build a product that people want and love

(26:44) How to determine product-market fit

(29:54) The benefits of this approach

(34:11) Real examples of using reference customers

(40:06) Doing things that don’t scale

(48:40) How to get better at coaching and build trust with leaders

(55:53) The fastest way to build trust

(01:00:01) What to do in the absence of good coaching

(01:02:51) How to get into product management

(01:04:16) The pitfalls of early promotions

(01:11:11) How to train someone for a promotion before giving the promotion

(01:13:30) How to find a good coach

(01:14:40) Christian’s product work in Africa

(01:21:22) The importance of passion and empathy in product work

(01:22:54) Lightning round

—

Referenced:

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

• The nature of product | Marty Cagan, Silicon Valley Product Group: https://www.lennyspodcast.com/the-nature-of-product-marty-cagan-silicon-valley-product-group/

• Silicon Valley Product Group: https://www.svpg.com/

• Enhanced Product Discovery by SVPG Partner Christian Idiodi at Lean Product Meetup: https://www.youtube.com/watch?v=eQKaFEqhiqc

• Geoffrey Moore’s technology adoption curve: https://fourweekmba.com/technology-adoption-curve/

• Stripe: https://stripe.com/

• Building a culture of excellence | David Singleton (CTO of Stripe): https://www.lennyspodcast.com/building-a-culture-of-excellence-david-singleton-cto-of-stripe/

• Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft): https://www.lennyspodcast.com/building-beautiful-products-with-stripes-head-of-design-katie-dill-stripe-airbnb-lyft/

• Rippling: https://www.rippling.com/

• Snagajob: https://www.snagajob.com/

• Howard Schultz on LinkedIn: https://www.linkedin.com/in/howardschultz/

• Tesla portable charger: https://shop.tesla.com/product/mobile-connector

• Innovate Africa Foundation: https://www.innovateafrica.io/about/

• Inspire Africa Conference: https://www.inspireafricaconference.com/

• Inspired: How to Create Tech Products Customers Love: https://www.svpg.com/books/inspired-how-to-create-tech-products-customers-love-2nd-edition/

• Empowered: Ordinary People, Extraordinary Products: https://www.svpg.com/books/empowered-ordinary-people-extraordinary-products/

• Transformed: Moving to the Product Operating Model: https://www.svpg.com/books/transformed-moving-to-the-product-operating-model/

• Succession on HBO: https://www.hbo.com/succession

• Billions on Showtime: https://www.sho.com/billions

• Real sports app: https://www.realapp.link/

—

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

—

Lenny may be an investor in the companies discussed.

Jason Fried is the co-founder and CEO of 37signals, the maker of Basecamp and HEY. 37signals is a very different kind of company. With fewer than 80 employees, they have over 100,000 customers, generate tens of millions of dollars in profit each year, and have no investors, board, or any plans to ever raise money or sell the company. In our conversation, we explore a path many tech founders never consider—bootstrapping. We discuss:

• Why he and his team prioritize profit above all else

• The unexpected challenges with raising venture capital

• The “Shape Up” framework for building products

• Why, and how, to foster a gut-driven culture

• Jason’s thoughts on why work should not feel like war

• Advice for starting a bootstrapped business

• The philosophy behind Once, 37signals’s new line of software products

—

Brought to you by Coda—Meet the evolution of docs | Sidebar—Accelerate your career by surrounding yourself with extraordinary peers | Wix Studio—The web creation platform built for agencies

—

Find the full transcript at: https://www.lennyspodcast.com/jason-fried-challenges-your-thinking-on-fundraising-goals-growth-and-more/#transcript

—

Where to find Jason Fried:

• X: https://twitter.com/jasonfried

• LinkedIn: https://www.linkedin.com/in/jason-fried/

• Email: jason@hey.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) Jason’s background

(03:49) The success of 37signals

(06:46) When raising money makes sense

(09:58) The power of small teams

(13:55) Defining success and goals

(17:08) Playing “infinite games” in life

(20:11) Starting a business vs. staying in business

(22:13) Lessons from 25 years in business

(27:28) Venture scale vs. bootstrapping

(30:30) Choosing the right path for your business

(33:19) The “Shape Up” framework

(37:59) The drawback of promises

(39:56) Adopting a new way of working

(41:36) The two-week cooldown

(43:53) Trusting intuition and gut

(46:41) Creating a gut-driven culture

(49:44) What Jason looks for in new hires

(56:19) Advice on making changes and adapting

(01:00:06) What Jason has changed his mind about

(01:02:33) Planning in 6-week stretches and figuring it out as you go

(01:06:43) Being proud of the work you do

(01:09:05) Jason’s thoughts on why work should not feel like war

(01:11:31) Advice for starting a bootstrapped business

(01:14:33) You must be at peace with the worst that can happen

(01:15:42) The benefits of bootstrapping

(01:19:11) The value of constraints in business

(01:22:00) Jason’s philosophy: “Just keep making great s**t”

(01:23:19) Once, 37signals’s new line of software products

(01:26:33) The philosophy behind Once

(01:35:47) Closing thoughts

(01:37:23) Lightning round

—

Referenced:

• 37 Signals: https://www.smartsheet.com/

• Basecamp: https://basecamp.com/

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

• Ingram Micro: https://www.ingrammicro.com/

• Once: https://once.com/

• Basecamp’s Shape Up framework: https://basecamp.com/shapeup

• Hill charts: https://basecamp.com/features/hill-charts

• Jason Fried’s quote about long-term business planning: https://medium.com/@farkhan569/unless-you-are-a-fortune-teller-long-term-business-planning-is-a-fantasy-jason-fried-quote-a69e8778e9c4

• Brian Chesky’s new playbook: https://www.lennyspodcast.com/brian-cheskys-new-playbook/

• Matt Mullenweg on X: https://twitter.com/photomatt

• Leo Polovets on X: https://twitter.com/lpolovets

• HEY: https://www.hey.com/

• Redefining success, money, and belonging | Paul Millerd (The Pathless Path): https://www.lennyspodcast.com/redefining-success-money-and-belonging-paul-millerd-the-pathless-path/

• It Doesn’t Have to Be Crazy at Work: https://www.amazon.com/Doesnt-Have-Be-Crazy-Work/dp/0062874780

• Squarespace: https://www.squarespace.com/

• Stoic negative visualization: https://dailystoic.com/premortem/

• Linear: https://linear.app/

• Peter Rahal on LinkedIn: https://www.linkedin.com/in/peter-rahal-037bba43/

• RXBAR: https://www.rxbar.com/en_US/home.html

• Jason’s LinkedIn post: https://www.linkedin.com/posts/jason-fried_just-keep-making-great-s**t-keep-your-costs-activity-7130978623523614720-VBGX/?trk=public_profile

• Several Short Sentences About Writing: https://www.amazon.com/Several-Short-Sentences-About-Writing/dp/0307279413

• Hell Yeah or No: What’s Worth Doing: https://www.amazon.com/Hell-Yeah-No-whats-worth/dp/1988575117/

• Home-Made: Contemporary Russian Folk Artifacts: https://www.amazon.com/Home-Made-Contemporary-Russian-Folk-Artifacts/dp/0955006139

• Oppenheimer: https://www.oppenheimermovie.com/

• Tom Petty’s “Crawling Back to You” on Spotify: https://open.spotify.com/track/1JenqZNMU6unIwVWmoP3J0

• Poor Charlie’s Almanack: The Essential Wit and Wisdom of Charles T. Munger: https://press.stripe.com/poor-charlies-almanack

—

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

—

Lenny may be an investor in the companies discussed.

Matthew Dicks is a best-selling author, columnist, blogger, podcaster, playwright, and teacher. He wrote my all-time favorite book on storytelling, Storyworthy. He is an elementary school teacher by day and by night teaches storytelling and public speaking to individuals, corporations, universities, religious institutions, and school districts around the world. He’s taught storytelling at Yale, MIT, Harvard, and Purdue, along with Amazon, Salesforce, Slack, Lego, and others. In this conversation, Matthew shares insights and techniques for effective storytelling, including:

• The benefits of good storytelling in business

• The five-second moment and why it’s so important

• Why you should start every story at the end

• How to build a vault of stories that can be deployed in business situations

• Tips on how to be funnier

• His life-changing “Homework for Life” practice

• Advice for dealing with nervousness in public speaking

• The power of saying yes

—

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Find the full transcript at: https://www.lennyspodcast.com/how-to-tell-better-stories-matthew-dicks-storyworthy/

—

Where to find Matthew Dicks:

• Website: https://matthewdicks.com/

• X: https://twitter.com/MatthewDicks

• LinkedIn: https://www.linkedin.com/in/matthew-dicks-84a95711/

• YouTube: https://www.youtube.com/channel/UC4K0fcEJkzJLso5h6CN00LQ

• Storyworthy: https://www.storyworthymd.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) Matthew’s background

(04:27) The five-second moment

(10:29) Knowing the ending

(14:28) The importance of including a transformation

(15:59) The dinner test

(18:19) You can’t tell someone else’s story

(20:24) Vacation stories

(23:14) Adding stakes to the story

(25:12) The power of surprise

(29:20) The benefits of storytelling in business

(32:20) An example of adding stakes

(34:02) Storytelling in the workplace

(44:29) Using personal inventory to make stories relatable

(48:46) Four ways to keep people listening

(50:52) Using humor in business storytelling

(53:09) Advice for adding humor

(58:43) An example of how storytelling helped a biotech company sell product

(1:02:06) Advice for people who don’t want to become storytellers

(1:06:35) The power of “Homework for Life”

(01:15:26) Practical tips for starting Homework for Life

(01:19:28) Dealing with nervousness in public speaking

(01:24:42) Preparing for a talk or presentation

(01:25:24) The power of saying yes

(01:30:55) Lightning round

—

Referenced:

• How ‘Star Wars’ answers our biggest religious questions: https://www.washingtonpost.com/posteverything/wp/2015/04/21/how-star-wars-answers-our-biggest-religious-questions/

• When Harry Met Sally on Prime Video: https://www.amazon.com/When-Harry-Sally-Billy-Crystal/dp/B001Q556QG

• Persuasive communication and managing up | Wes Kao (Maven, Seth Godin, Section4): https://www.lennyspodcast.com/persuasive-communication-and-managing-up-wes-kao-maven-seth-godin-section4/

• Kurt Vonnegut’s 8 Tenets of Storytelling: https://www.themarginalian.org/2012/04/03/kurt-vonnegut-on-writing-stories/

• Vertigo on Prime Video: https://www.amazon.com/Vertigo-James-Stewart/dp/B000I9YLXU

• Ocean’s Eleven on Prime Video: https://www.amazon.com/Oceans-Eleven-George-Clooney/dp/B001EBV0JE

• David Mamet | JCCSF: https://www.youtube.com/watch?v=aZOT1jCHfhI

• Pulp Fiction on Prime Video: https://www.amazon.com/Pulp-Fiction-John-Travolta/dp/B005T3AX6E

• Charity Thief: Boston Moth StorySLAM: https://www.youtube.com/watch?v=YjrlGhAB4a4

• Boris Levin on LinkedIn: https://www.linkedin.com/in/boris-levin-ab95404/

• Masha Reutovski on LinkedIn: https://www.linkedin.com/in/masha-reutovski/

• Top Three Steve Jobs Speeches: https://www.pcworld.com/article/482269/top_three_steve_jobs_speeches.html

• The Javits Center: https://www.javitscenter.com/

• Stranger Things on Netflix: https://www.netflix.com/title/80057281

• 1989 (Taylor’s Version) on Spotify: https://open.spotify.com/album/64LU4c1nfjz1t4VnGhagcg

• Classic Sesame Street—one of these things is not like the other: https://www.youtube.com/watch?v=gCxrkl2igGY

• Homework for Life: https://matthewdicks.com/homework-for-life/

• Homework for Life | Matthew Dicks | TEDxBerkshires: https://www.youtube.com/watch?v=x7p329Z8MD0

• Seth Meyers: https://en.wikipedia.org/wiki/Seth_Meyers

• David Sedaris on MasterClass: https://www.masterclass.com/classes/david-sedaris-teaches-storytelling-and-humor

• Happy-Go-Lucky: https://www.amazon.com/Happy-Go-Lucky-David-Sedaris/dp/0316392456

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

• New York Comedy Festival: https://nycomedyfestival.com/

• In the Heart of the Sea: The Tragedy of the Whaleship Essex: https://www.amazon.com/Heart-Sea-Tragedy-Whaleship-Essex/dp/0141001828

• The Tale of Despereaux: https://www.amazon.com/Tale-Despereaux-Being-Princess-Thread/dp/0763680893

• I’ll Show Myself Out: Essays on Midlife and Motherhood: https://www.amazon.com/Ill-Show-Myself-Out-Motherhood/dp/0062981595

• You’ll Grow Out of It: https://www.amazon.com/Youll-Grow-Out-Jessi-Klein/dp/1455531200

• David Sedaris books: https://www.amazon.com/stores/David-Sedaris/author/B000AQ3YUW

• Sure, I’ll Join Your Cult: A Memoir of Mental Illness and the Quest to Belong Anywhere: https://www.amazon.com/Sure-Ill-Join-Your-Cult/dp/1982168560

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

• Barbie: https://www.barbie-themovie.com/

• Krinner tree genie on Amazon: https://www.amazon.com/Krinner-Genie-Christmas-Stand-Small-Green/dp/B081D78FTP

• Power Pod: https://powerpodshop.com/

• Nostalgia hotdog toaster: https://www.amazon.com/Nostalgia-HDT600RETRORED-Pop-Up-Toaster-Retro/dp/B005Q8X6IO

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

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Lenny may be an investor in the companies discussed.

In this special compilation episode, we delve into failure—an overlooked source of wisdom. From freezing onstage in front of thousands of people, to coworkers staging an intervention, to huge product investments that went to zero, we’ve pulled our favorite stories of failure from 100+ podcast episodes. I hope these stories serve as a gentle nudge to view failure not as a setback but as a crucial detour toward growth.

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Brought to you by Sendbird—The (all-in-one) communications API platform for mobile apps | Eppo—Run reliable, impactful experiments

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Find the full transcript at: https://www.lennyspodcast.com/failure/

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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, you’ll hear from:

(00:00) Lenny: Why I’m focusing on failure

(03:25) Katie Dill: The single meeting that changed how Katie leads forever

(08:03) Paul Adams: Freezing onstage in front of thousands of people

(18:38) Tom Conrad: Lessons from Pets.com and Quibi—two of the most famous product disasters of all time

(33:19) Sri Batchu: When you fail, make sure you fail conclusively

(39:00) Jiaona Zhang (JZ): One of the biggest product misses at Airbnb

(44:32) Gina Gotthilf: Everyone has an “A side” and a “B side,” and we should all share our B sides more

(57:57) Maggie Crowley: Her favorite interview question about failure, and lessons from a personal failure

(1:00:33) Thanks for listening

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

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Lenny may be an investor in the companies discussed.

Kim Scott is the author of Radical Candor, currently the #1 most recommended book on this podcast. The book has sold over 1 million copies and has been translated into 23 languages. Before writing, Kim was a CEO coach at Dropbox, Qualtrics, Twitter, and other tech companies. She was also a member of the faculty at Apple University and before that led AdSense, YouTube, and DoubleClick teams at Google. This spring she’ll be launching Radical Respect, which she considers to be a prequel to Radical Candor. In today’s conversation, we go deep on Kim’s popular framework, including:

• What separates radical candor and obnoxious aggression

• Tactical advice on delivering constructive feedback

• How well-meaning empathy can become ruinous

• Strategies for effectively soliciting and responding to feedback

• The importance of having regular career conversations

• The false dichotomy of a good leader versus a kind person

• A sneak peek into Radical Respect

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Brought to you by Jira Product Discovery—Atlassian’s new prioritization and roadmapping tool built for product teams

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Find the full transcript at: https://www.lennyspodcast.com/radical-candor-from-theory-to-practice-with-author-kim-scott/#transcript

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Where to find Kim Scott:

• X: https://twitter.com/kimballscott

• LinkedIn: https://www.linkedin.com/in/kimm4/

• Website: https://www.radicalcandor.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) Kim’s background

(03:13) A brief overview of Radical Candor

(06:46) How people fail with ruinous empathy, manipulative insincerity, and obnoxious aggression

(08:37) The impact of radical candor on Kim’s life

(14:16) How to communicate feedback effectively

(20:34) A story illustrating the problem with ruinous empathy and manipulative insincerity

(27:50) How to get over the need to be liked

(31:31) How to have career conversations with your direct reports

(29:40) Reflections on how Kim handled an underperforming employee

(33:31) Best practices for soliciting feedback as a leader

(35:53) How to respond to feedback

(39:22) How often to ask for feedback

(41:48) Whether or not to accept “no feedback” as an answer

(50:48) Investing time in feedback

(54:04) How to ask for feedback as an employee

(57:42) Why obnoxious aggression is not the best way to deliver feedback

(1:01:23) A notable example of problematic management 

(1:03:43) Why context matters when diagnosing obnoxious aggression 

(1:07:39) Empathy is a good thing, but empathy can paralyze

(1:10:47) Reflections on the limitations of radical candor in a society riddled with biases 

(1:14:41) Kim’s new book, Radical Respect

(1:15:51) Tactical advice to get better at radical candor

(1:16:46) Lightning round

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Referenced:

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

• Radical Respect: How to Work Together Better: https://www.amazon.com/Radical-Respect-Work-Together-Better/dp/1250623766/

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

• Radical Candor diagram: https://www.radicalcandor.com/our-approach/

• A behavioral scientist explains why we should reacquaint ourselves with the telephone: https://news.uchicago.edu/story/nicholas-epley-explains-why-phone-calls-can-connect-us-better-zoom

• How to get promoted: https://www.lennysnewsletter.com/p/how-to-get-promoted

• When They Win, You Win: Being a Great Manager Is Simpler Than You Think: https://www.amazon.com/When-They-Win-You-Manager/dp/1250279666

• Peter Kazanjy on X: https://twitter.com/Kazanjy

• Christa Quarles on LinkedIn: https://www.linkedin.com/in/christaquarles/

• Jason Rosoff on LinkedIn: https://www.linkedin.com/in/jason-r-rosoff/

• Andrew Grove: https://en.wikipedia.org/wiki/Andrew_Grove

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

• Squid Game on Netflix: https://www.netflix.com/title/81040344

• Leveraging mentors to uplevel your career | Jules Walter (YouTube, Slack): https://www.lennyspodcast.com/leveraging-mentors-to-uplevel-your-career-jules-walter-youtube-slack/

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

• Bridgewater: https://www.bridgewater.com/

• The Fund: Ray Dalio, Bridgewater Associates, and the Unraveling of a Wall Street Legend: https://www.amazon.com/Fund-Bridgewater-Associates-Unraveling-Street/dp/1250276934/

• Tim Cook on X: https://twitter.com/tim_cook

• Elon Musk: https://www.amazon.com/Elon-Musk-Walter-Isaacson/dp/1982181281

• Building high-performing teams | Melissa Tan (Webflow, Dropbox, Canva): https://www.lennyspodcast.com/building-high-performing-teams-melissa-tan-webflow-dropbox-canva/

• Middlemarch: https://www.amazon.com/Middlemarch-Penguin-Classics-George-Eliot/dp/0141439548

• The Bluest Eye: https://www.amazon.com/Bluest-Eye-Vintage-International/dp/0307278441

• Song of Solomon: https://www.amazon.com/Song-Solomon-Toni-Morrison/dp/140003342X

• Orlando: https://www.amazon.com/Orlando-Biography-Virginia-Woolf/dp/015670160X

• The Color Purple: https://www.amazon.com/Color-Purple-Novel-Alice-Walker/dp/0143135694

• The Deptford Trilogy: Fifth Business; The Manticore; World of Wonders: https://www.amazon.com/Deptford-Trilogy-Business-Manticore-Wonders/dp/0140147551

• Grey’s Anatomy on Netflix: https://www.netflix.com/title/70140391

• My year of saying yes to everything: https://www.ted.com/talks/shonda_rhimes_my_year_of_saying_yes_to_everything

• Attitude: https://attitudeliving.com/collections/adult-hair-care

• Dostoevsky books: https://www.amazon.com/Fyodor-Dostoevsky-Books/s?k=Fyodor+Dostoevsky

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

—

Lenny may be an investor in the companies discussed.