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    My favorite interview questions from 100+ guests

    enNovember 29, 2023
    What was the main topic of the podcast episode?
    Summarise the key points discussed in the episode?
    Were there any notable quotes or insights from the speakers?
    Which popular books were mentioned in this episode?
    Were there any points particularly controversial or thought-provoking discussed in the episode?
    Were any current events or trending topics addressed in the episode?

    Podcast Summary

    • Assessing self-awareness and curiosity in job candidatesAsking 'To what do you attribute your success? And you can't say luck' reveals a candidate's self-awareness and curiosity, crucial traits for potential success. Utilize tools like Sendbird and EPO to enhance in-app communication and experimentation for better engagement, conversion, and retention.

      The importance of self-awareness and curiosity in determining an interviewee's potential for success. The host discussed his favorite interview questions shared by previous podcast guests, which included Eike DiMaliano, former head of product at Retool and PM at Stripe, who posed the question, "To what do you attribute your success? And you can't say luck." By asking this question, Eike aimed to assess a candidate's self-awareness and curiosity. This question can help uncover a candidate's ability to reflect on their accomplishments, understand their strengths and weaknesses, and demonstrate a growth mindset. Additionally, the episode highlighted Sendbird, an all-in-one communications API platform, and EPO, a next-generation AB testing and feature management platform, both of which can significantly enhance in-app communication and experimentation, respectively. By using these tools, businesses can improve engagement, conversion, and retention, making them valuable resources for forward-thinking companies.

    • Exploring individual approaches to challengesUnderstanding how individuals approach challenges can reveal their thought processes and work ethic. Asking the right questions and identifying essential information are crucial for effective problem-solving.

      Understanding how individuals approach and overcome challenges can provide valuable insights into their thought processes and work ethic. This was explored in interviews with Jeff Charles, head of product at Ramp, and Shashir Marhotra, CEO and co-founder of Coda. Jeff discussed the hardest thing he's ever done and how he overcame it, revealing his perspective on difficulty and determination. Shashir shared his favorite interview question, which involves imagining a teleportation device and being asked to create a plan with only two allowed questions. This question highlights the importance of identifying essential information and prioritizing questions effectively. Both discussions underscore the significance of asking the right questions and understanding how individuals tackle complex problems.

    • Understanding the root causes of problemsAsking the right questions and understanding underlying motivations and conflicts can lead to better problem-solving and effective solutions.

      Understanding the underlying questions behind a problem can help identify the key factors and potential solutions. This was highlighted in a discussion about hypothetical teleportation devices, where two seemingly contradictory scenarios were identified based on the cost and safety considerations. The ability to simplify complex problems, as demonstrated by children, was also emphasized. Moreover, the interview question from Yuki Yamashita about a controversial product assistant experience underscores the importance of acknowledging and addressing conflicts in product development. By understanding the reasons behind these conflicts, we can gain valuable insights and make informed decisions. The discussion also emphasized the importance of asking item questions to understand the factors that drive the placement and success of various products, such as gas stations. Overall, the key takeaway is that asking the right questions and understanding the underlying motivations and conflicts can lead to better problem-solving and more effective solutions.

    • Assessing a candidate's storytelling and ambiguity handling skillsAsking about proudest work and past ambiguous situations reveals a candidate's values, motivations, and work ethic, as well as their ability to navigate ambiguity and communicate effectively as a product manager.

      Effective product managers possess strong storytelling communication skills and the ability to navigate ambiguity. During interviews, asking candidates about their proudest work allows product managers to understand their values, motivations, and work ethic. This question also provides insight into what good outcomes look like to the candidate. Additionally, asking behavioral questions about how candidates have handled ambiguous situations in the past helps assess their ability to put structure and a clear path forward in the ambiguous role of a product manager.

    • Seeking constant feedback and growthSuccessful product leaders value humility, curiosity, self-awareness, and seek to build teams of passionate, curious, and committed individuals.

      Successful product leaders are constantly seeking feedback, learning from their experiences, and striving for personal and professional growth. They value humility, curiosity, and self-awareness, and are always looking for ways to improve themselves and their teams. When interviewing potential hires, they evaluate not only professional qualifications but also cultural fit and alignment with values. Asking thought-provoking questions like "What unfair secrets have you learned?" or "Tell me about your diversity, equity, inclusion initiatives" can reveal a candidate's character and approach to problem-solving. Ultimately, the goal is to build a team of individuals who are passionate, curious, and committed to creating great products and experiences for their users.

    • Asking insightful questions in product management interviewsAsking about past challenges, unconventional wisdom, and unexpected outcomes can reveal a candidate's self-awareness, problem-solving abilities, and authenticity.

      Effective interviewing for product management roles involves asking questions that reveal a candidate's self-awareness, problem-solving abilities, and authenticity. During the discussion, the interviewees shared their preferred questions and why they find them valuable. For instance, asking about a time something went wrong helps evaluate a candidate's mindset and self-awareness when faced with challenges. Asking about conventional wisdom they bet against tests their ability to think critically and authentically. Lastly, asking about unexpected outcomes of past decisions assesses their introspective nature and learning abilities. These questions can provide valuable insights into a candidate's character and problem-solving skills, making them invaluable additions to the interview process.

    • Encouraging self-reflection during interviewsAsking thoughtful questions that encourage self-reflection can help interviewers gain insights into a candidate's character, motivations, and potential for growth.

      Self-reflection and introspection are crucial for growth, both personally and professionally. During interviews, it's essential to ask questions that encourage candidates to think deeply about their experiences and motivations. Lauren Isford's question about delivering something impactful is a great example, as it encourages candidates to discuss their intrinsic motivation and the significance of their contributions. Another valuable insight comes from Paul Adams' advice on conducting reference checks. By asking candidates what feedback they would expect in their first performance review, interviewers can gain a better understanding of their self-awareness and growth mindset. Overall, these interview questions aim to uncover valuable insights about a candidate's character, motivations, and potential for growth. By asking thoughtful questions and encouraging self-reflection, interviewers can make more informed hiring decisions and build strong, impactful teams.

    Recent Episodes from Lenny's Podcast: Product | Growth | Career

    Airbnb’s Vlad Loktev on embracing chaos, inquiry over advocacy, poking the bear, and “impact, impact, impact” (Partner at Index Ventures, Airbnb GM/VP Product)

    Airbnb’s Vlad Loktev on embracing chaos, inquiry over advocacy, poking the bear, and “impact, impact, impact” (Partner at Index Ventures, Airbnb GM/VP Product)

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

    • Insight into Brian Chesky’s leadership style

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

    • Why chaos can be good

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

    • Why you should learn to “poke the bear”

    • Balancing product release speed with quality

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

    • Advice for founders on building company culture

    • Much more

    Brought to you by:

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

    Vanta—Automate compliance. Simplify security

    Eppo—Run reliable, impactful experiments

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

    Where to find Vlad Loktev:

    • X: https://x.com/vladimirloktev

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

    Where to find Lenny:

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

    • X: https://twitter.com/lennysan

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

    In this episode, we cover:

    (00:00) Vlad’s background

    (02:54) Reflecting on transformative years at Airbnb

    (04:28) Skills and mindsets for success

    (11:03) Impact-driven mindset

    (13:16) Saying no and inquiry before advocacy 

    (17:54) “Poking the bear”

    (22:46) Psychological tools for leadership

    (30:08) Building and scaling teams

    (36:12) Letting fires burn

    (47:34) Embracing chaos

    (54:40) The unsell email strategy

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

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

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

    (01:26:41) Failure corner

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

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

    Lenny may be an investor in the companies discussed.



    Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

    How to consistently go viral: Nikita Bier’s playbook for winning at consumer apps (co-founder of TBH, Gas, advisor, investor)

    How to consistently go viral: Nikita Bier’s playbook for winning at consumer apps (co-founder of TBH, Gas, advisor, investor)

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

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

    • Strategies for building viral consumer apps

    • Why teens are such a great audience

    • Fighting the human trafficking hoax at Gas

    • The challenge of creating durable social products

    • His experience working as a PM at Facebook

    • Advice for founders on building consumer apps

    • Much more

    Brought to you by:

    Webflow—The web experience platform

    Vanta—Automate compliance. Simplify security

    Explo—Embed customer-facing analytics in your product

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

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

    Where to find Nikita Bier:

    • X: https://x.com/nikitabier 

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

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

    Where to find Lenny:

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

    • X: https://twitter.com/lennysan

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

    In this episode, we cover:

    (00:00) Nikita’s background 

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

    (08:42) Transition to consumer apps

    (13:45) The birth of TBH

    (16:43) Building for teens vs. adults

    (20:00) TBH’s viral success

    (32:18) Leveraging live chat

    (34:08) Lasting lessons from TBH

    (37:00) Selling TBH to Facebook

    (42:19) Big-tech product management

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

    (51:49) The Tim Cook painting story

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

    (58:02) Rebuilding TBH and overcoming challenges

    (59:46) Addressing criticism

    (01:04:24) The human trafficking hoax

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

    (01:11:36) Lasting lessons from Gas

    (01:13:14) Building durable consumer apps

    (01:22:35) The VC route

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

    (01:26:53) The success of Dupe

    (01:31:53) Advice for startup founders

    (01:34:14) Work with Nikita

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

    Lenny may be an investor in the companies discussed.



    Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

    Succeeding as an introvert, building zero-to-one, and why you should PM your career like you PM your product | Deb Liu (CEO of Ancestry, ex-Facebook, PayPal, eBay)

    Succeeding as an introvert, building zero-to-one, and why you should PM your career like you PM your product | Deb Liu (CEO of Ancestry, ex-Facebook, PayPal, eBay)

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

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

    • Strategies for incubating new products within large companies

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

    • The pitfalls of perfectionism

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

    • The value of resilience and turning failures into stepping stones

    • How to leverage coaching in your career development

    Brought to you by:

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

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

    Webflow—The web experience platform

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

    Where to find Deb Liu:

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

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

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

    Where to find Lenny:

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

    • X: https://twitter.com/lennysan

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

    In this episode, we cover:

    (00:00) Introduction to Deb Liu

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

    (09:45) Navigating new roles and challenges

    (11:27) Overcoming adversity and failure

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

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

    (23:40) PM your career like a product

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

    (39:19) Reframing self-promotion

    (42:25) The power of accountability

    (46:15) Growth: a game of inches

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

    (56:52) Contrarian corner: career and marriage

    (58:57) Final nuggets of wisdom

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

    (01:04:47) Lightning round

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

    Lenny may be an investor in the companies discussed.



    Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

    Unorthodox PM wisdom: Automating user insights, unselling job candidates, logging every decision, more | Kevin Yien (Stripe, Square, Mutiny)

    Unorthodox PM wisdom: Automating user insights, unselling job candidates, logging every decision, more | Kevin Yien (Stripe, Square, Mutiny)

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

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

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

    • How to automate user research

    • Kevin’s “unsell email” technique for hiring

    • The value of keeping a decision log

    • Insights on AI and its impact on future generations

    • Lessons from failure

    Brought to you by:

    BuildBetter—AI for product teams

    OneSchema—Import CSV data 10x faster

    Eppo—Run reliable, impactful experiments

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

    Where to find Kevin Yien:

    • X: https://x.com/kevinyien

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

    • Website: https://kevinyien.com/

    Where to find Lenny:

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

    • X: https://twitter.com/lennysan

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

    In this episode, we cover:

    (00:00) Kevin’s background 

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

    (08:41) The role of a product manager

    (10:48) Getting started in product management

    (12:47) The importance of writing skills

    (15:06) Becoming a better writer

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

    (28:41) Drawing the perimeter for your team

    (31:37) Feedback tips

    (35:13) Decision logs and product sense

    (45:36) Unorthodox hiring strategies

    (47:01) The unsell email strategy

    (54:01) Automating user research

    (01:02:27) AI in everyday life

    (01:06:05) Lessons from failure

    (01:14:34) Lightning round

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

    Lenny may be an investor in the companies discussed.



    Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

    Improve strategy, influence, and decision-making by understanding your brain | Evan LaPointe (founder of CORE Sciences)

    Improve strategy, influence, and decision-making by understanding your brain | Evan LaPointe (founder of CORE Sciences)

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

    • The three different systems of the brain

    • How knowing this can help you become more influential

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

    • How to improve your vision and strategy skills

    • How to design a work environment that fosters innovation

    • How to build better relationships at work

    • Much more

    Brought to you by:

    Webflow—The web experience platform

    Explo—Embed customer-facing analytics in your product

    Eppo—Run reliable, impactful experiments

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

    Where to find Evan LaPointe:

    • X: https://x.com/evanlapointe

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

    • Website: https://www.core-sciences.com/

    Where to find Lenny:

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

    • X: https://twitter.com/lennysan

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

    In this episode, we cover:

    (00:00) Evan’s background

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

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

    (11:03) Applying brain science to team dynamics

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

    (17:27) Creating effective work environments

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

    (29:35) Enhancing strategy and vision

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

    (58:58) Tactical tips for increasing openness

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

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

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

    (01:50:35) Enhancing focus and productivity

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

    (02:07:11) Lightning round

    Referenced:

    • The Most Complicated Object in the Universe: https://today.uconn.edu/2018/03/complicated-object-universe/#

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

    • The Big Five personality test: https://www.thepersonalitylab.org/

    • The Enneagram personality test: https://enneagramtest.com/

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

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

    • Dylan Field live at Config: Intuition, simplicity, and the future of design: https://www.lennysnewsletter.com/p/dylan-field-live-at-config

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

    • Inside Canva: Coaches not managers, giving away your Legos, and running profitably | Cameron Adams (co-founder and CPO): https://www.lennysnewsletter.com/p/inside-canva-with-cameron-adams

    • The Science-Business Mismatch That Puts Your Change at Risk: https://changemanagementreview.com/the-science-business-mismatch-that-puts-your-change-at-risk/

    • Daniel Pink on LinkedIn: https://www.linkedin.com/in/danielpink/

    • Trello: https://trello.com/

    • Cron: https://cronhq.notion.site/

    • The Double Diamond framework for design thinking: https://www.fluxspace.io/resources/the-4-ds-double-diamond-design-thinking-model

    • CORE Sciences - Tips on Priming Great Meetings PDF: https://www.dropbox.com/scl/fi/gm21cj0vi0bjosyu8kd69/CORE-Sciences-Tips-on-Priming-Great-Meetings.pdf?rlkey=6fznhv7bbsxm8nj8m4luej17t&st=2eduirad&dl=0

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

    • Brené Brown’s website: https://brenebrown.com/

    • The CORE personality test: https://www.core-sciences.com/new-core-identity

    • Burning Man: https://burningman.org/

    • Stripe: https://stripe.com/

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

    • Albert Einstein quote: https://www.goodreads.com/quotes/7133605-make-things-as-simple-as-possible-but-no-simpler

    • Elden Ring: https://en.bandainamcoent.eu/elden-ring/elden-ring

    • Abilene paradox: https://en.wikipedia.org/wiki/Abilene_paradox

    The Challenger Sale: Taking Control of the Customer Conversation: https://www.amazon.com/Challenger-Sale-Control-Customer-Conversation/dp/1591844355

    • The surprising truth about what closes deals: Insights from 2.5m sales conversations | Matt Dixon (author of The Challenger Sale and The JOLT Effect): https://www.lennysnewsletter.com/p/close-more-deals-matt-dixon

    • Siqi Chan on X: https://x.com/blader

    • Runway: https://runway.com/

    • Shreyas Doshi on pre-mortems, the LNO framework, the three levels of product work, why most execution problems are strategy problems, and ROI vs. opportunity cost thinking: https://www.lennysnewsletter.com/p/episode-3-shreyas-doshi

    • Wolfgang Puck’s website: https://wolfgangpuck.com/

    • Steven Spielberg on X: https://x.com/sspielberg93

    • John Williams’s website: https://www.johnwilliams.org/

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

    • Warby Parker: https://www.warbyparker.com/

    • Simon Sinek’s website: https://simonsinek.com/

    • What is the function of the various brainwaves?: https://www.scientificamerican.com/article/what-is-the-function-of-t-1997-12-22/

    • CORE Sciences - Your Brain's 9 Modes PDF: https://www.dropbox.com/scl/fi/figg8upeaawir1hnxv0ew/CORE-Sciences-Your-Brain-s-9-Modes.pdf?rlkey=u3zaonxvycvupurq6pwysckfq&st=os06xjnr&dl=0

    Never Split the Difference: Negotiating As If Your Life Depended On It: Unlock Your Persuasion Potential in Professional and Personal Life: https://www.amazon.com/Never-Split-Difference-Negotiating-Depended/dp/0062407805

    The Person and the Situation: Perspectives of Social Psychology: https://www.amazon.com/Person-Situation-Perspectives-Social-Psychology/dp/1905177445

    Cambridge Fundamentals of Neuroscience in Psychology: https://www.amazon.com/Cambridge-Fundamentals-Neuroscience-Psychology/dp/B08QYNDNYX

    • Robert Greene’s books on Amazon: https://www.amazon.com/stores/Robert-Greene/author/B001IGV3IS

    Misbehaving: The Making of Behavioral Economics: https://www.amazon.com/Misbehaving-Behavioral-Economics-Richard-Thaler/dp/039335279X

    • Beehiiv: https://www.beehiiv.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.



    Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

    How embracing your emotions will accelerate your career | Joe Hudson (executive coach, Art of Accomplishment)

    How embracing your emotions will accelerate your career | Joe Hudson (executive coach, Art of Accomplishment)

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

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

    • Why authenticity trumps self-improvement

    • The importance of embracing all of your emotions

    • How to create more enjoyable and effective meetings

    • The power of gratitude in transforming your life

    • Practical experiments for personal growth

    • Much more

    Apply for Joe’s Connection Course:

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

    Brought to you by:

    BuildBetter—AI for product teams

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

    Coda—The all-in-one collaborative workspace

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

    Where to find Joe Hudson:

    • X: https://x.com/FU_joehudson

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

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

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

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

    Where to find Lenny:

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

    • X: https://twitter.com/lennysan

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

    In this episode, we cover:

    (00:00) Joe’s background

    (02:31) The critical voice in your head

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

    (13:19) Understanding and embracing emotions

    (19:52) The importance of emotional fluidity

    (24:40) Questioning assumptions and self-perception

    (30:25) The consequences of avoiding emotions

    (36:57) Experimenting with self-improvement

    (39:42) Understanding efficiency and enjoyment

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

    (45:03) Innate enjoyment vs. learned enjoyment

    (46:31) Authenticity vs. self-improvement

    (50:01) Embracing emotional experiences

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

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

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

    (01:15:36) Conclusion and final thoughts

    Referenced:

    Descartes’ Error: Emotion, Reason, and the Human Brain: https://www.amazon.com/Descartes-Error-Emotion-Reason-Human/dp/014303622X/

    • Joe’s quote about joy: https://x.com/FU_joehudson/status/1756837774743790030

    • “Emotional Inquiry”: https://www.artofaccomplishment.com/podcast/emotional-inquiry

    Inside Out 2: https://movies.disney.com/inside-out-2

    • “Question the Assumption”: https://www.artofaccomplishment.com/podcast/question-the-assumption

    • Bodega Bay: https://www.bodegabay.com/

    • Elon Musk reveals the interview question he asks every candidate to instantly spot a liar: https://www.good.is/elon-musk-reveals-the-one-job-interview-question-he-asks-every-candidate-to-instantly-spot-a-liar

    • Great Decisions course: https://www.artofaccomplishment.com/course/great-decisions-course

    • HBR Analytic Services: https://hbr.org/hbr-analytic-services

    • Connection Course: https://www.artofaccomplishment.com/course/the-connection-course

    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.



    Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

    Lessons from scaling Uber and Opendoor | Brian Tolkin (Head of Product at Opendoor, ex-Uber)

    Lessons from scaling Uber and Opendoor | Brian Tolkin (Head of Product at Opendoor, ex-Uber)

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

    • How to enable product and ops to work well together

    • How to run great product reviews

    • How to make good decisions with limited data

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

    • How to stay calm under pressure as a leader

    • Wild stories from his time at Uber

    • Challenges faced at Opendoor during the pandemic

    • Much more

    Brought to you by:

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

    Explo—Embed customer-facing analytics in your product

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

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

    Where to find Brian Tolkin:

    • X: https://x.com/briantolkin

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

    Where to find Lenny:

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

    • X: https://twitter.com/lennysan

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

    In this episode, we cover:

    (00:00) Brian’s background

    (02:14) Career beginnings at Uber

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

    (06:47) Product and operations synergy

    (10:00) Surge pricing at Uber

    (12:18) Scaling challenges, and stories

    (15:47) Opendoor and Covid adaptations

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

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

    (42:23) Increasing conviction in solutions

    (44:33) Leveraging intuition in product decisions

    (47:07) Partnering with Zillow

    (52:55) Staying calm under pressure

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

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

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

    Referenced:

    • Twitter’s former Head of Product opens up: being fired, meeting Elon, changing stagnant culture, building consumer product, more | Kayvon Beykpour: https://www.lennysnewsletter.com/p/twitters-former-head-of-product-kayvon-beykpour

    • Opendoor: https://sell.opendoor.com/

    • How to sell your ideas and rise within your company | Casey Winters, Eventbrite: https://www.lennysnewsletter.com/p/how-to-sell-your-ideas-and-rise-within

    • Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub): https://www.lennysnewsletter.com/p/thinking-beyond-frameworks-casey

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

    • FlashTags: A Simple Hack for Conveying Context Without Confusion: https://www.onstartups.com/flashtags-a-simple-hack-for-conveying-context-without-confusion

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

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

    • Zillow: https://www.zillow.com/

    • Zillow, Opendoor announce multi-year partnership: https://investor.opendoor.com/news-releases/news-release-details/zillow-opendoor-announce-multi-year-partnership

    • Building product at Stripe: craft, metrics, and customer obsession | Jeff Weinstein (Product lead): https://www.lennysnewsletter.com/p/building-product-at-stripe-jeff-weinstein

    • Stripe Atlas: https://stripe.com/atlas

    Founders podcast: https://www.founderspodcast.com/

    • Uber will deliver ice cream to you today: https://www.dispatch.com/story/lifestyle/food/2016/07/13/uber-will-deliver-ice-cream/24201840007/

    • UberKittens: https://www.uber.com/newsroom/uberkittens/

    • UberPuppies: https://www.uber.com/blog/uberpuppies-want-to-play/

    Shoe Dog: A Memoir by the Creator of Nike: https://www.amazon.com/Shoe-Dog-Memoir-Creator-NIKE/dp/1471146723

    The Black Swan: The Impact of the Highly Improbable: https://www.amazon.com/Black-Swan-Impact-Improbable-Incerto/dp/1400063515

    The Design of Everyday Things: https://www.amazon.com/dp/0465050654

    Shantaram: https://www.amazon.com/Shantaram-SHANTARAM-Paperback-GregoryDavidRoberts/dp/B00QPVJESC

    Full Swing on Netflix: https://www.netflix.com/title/81483353

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

    Break Point on Netflix: https://www.netflix.com/title/81569920

    Air on Prime Video: https://www.amazon.com/AIR-Matt-Damon/dp/B0B8Q3JMCG

    • Fi smart dog collar: https://tryfi.com/

    • Particle: https://particlenews.ai/

    • Sara Beykpour on LinkedIn: https://www.linkedin.com/in/sarabeykpour/

    • A new-parent gift guide for product managers: https://www.lennysnewsletter.com/p/a-new-parent-gift-guide-for-product

    • Jeff Holden on LinkedIn: https://www.linkedin.com/in/jeffholden/

    • Travis Kalanick on X: https://x.com/travisk

    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.



    Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

    The ultimate guide to performance marketing | Timothy Davis (Shopify)

    The ultimate guide to performance marketing | Timothy Davis (Shopify)

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

    • When and how to start investing in performance marketing

    • Common mistakes companies make with paid ads

    • How to build and structure a performance marketing team

    • How to get your creatives performing better

    • Strategies for optimizing workflows and team efficiency

    • How AI will change performance marketing

    • Much more

    Brought to you by:

    BuildBetter—AI for product teams

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

    Where to find Timothy Davis:

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

    Where to find Lenny:

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

    • X: https://twitter.com/lennysan

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

    In this episode, we cover:

    (00:00) Timothy’s background 

    (02:31) Understanding performance marketing 

    (06:31) The importance of paid search 

    (08:39) Identifying growth potential 

    (09:54) Case studies: Hairstory and Ipsy 

    (12:22) Experimenting with new platforms 

    (18:57) Choosing the right platforms 

    (20:23) LinkedIn for B2B marketing 

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

    (33:33) Common mistakes in performance marketing 

    (37:41) Working with agencies and consultants 

    (40:36) Hiring for performance marketing 

    (47:33) Metrics that matter 

    (54:43) Competitor analysis and CPC insights 

    (56:15) Custom reports and data visualization

    (56:38) Understanding impression and click share 

    (59:10) True competition metrics 

    (01:02:14) Attribution and incrementality 

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

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

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

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

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

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

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

    (01:37:16) Lightning round 

    Referenced:

    • Shopify: https://www.shopify.com/

    • What Is Performance Marketing?: https://www.shopify.com/blog/performance-marketing

    • Google AI: https://ai.google/

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

    • Eventbrite: https://www.eventbrite.com/

    • Booking.com: https://www.booking.com/

    • Credit Karma: https://www.creditkarma.com/

    • Hairstory: https://hairstory.com/

    • Google Display Network: https://www.semrush.com/blog/google-display-network/

    • SoftLayer Becomes Part of IBM’s SmartCloud: https://www.datacenterknowledge.com/deals/softlayer-becomes-part-of-ibm-s-smartcloud

    • Coca-Cola Freestyle: https://www.coca-colafreestyle.com/

    • Monday.com: https://monday.com/

    • How to sell your ideas and rise within your company | Casey Winters, Eventbrite: https://www.lennysnewsletter.com/p/how-to-sell-your-ideas-and-rise-within

    • Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub): https://www.lennysnewsletter.com/p/thinking-beyond-frameworks-casey

    The Signal and the Noise: Why So Many Predictions Fail—But Some Don’t: https://www.amazon.com/Signal-Noise-Many-Predictions-Fail-but/dp/0143125087

    • Courtney Wenneborg on LinkedIn: https://www.linkedin.com/in/cwenneborg/

    • PPC Hero: https://www.ppchero.com/

    • Another Deep Dive into Auction Insights, by Jacob Brown: https://www.ppchero.com/another-deep-dive-into-auction-insights/

    •Multitouch: https://multitouch.app/

    • What is time decay attribution?: https://growthmethod.com/what-is-time-decay-attribution/

    • Linear: https://linear.app/

    • Consumer Heterogeneity and Paid Search Effectiveness: A Large-Scale Field Experiment: https://faculty.haas.berkeley.edu/stadelis/BNT_ECMA_rev.pdf

    • ADT: https://www.adt.com/

    • Shopify Bursts: https://focus.business/blog/shopify-bursts/

    The First 90 Days: Proven Strategies for Getting Up to Speed Faster and Smarter: https://www.amazon.com/First-90-Days-Strategies-Expanded/dp/1422188612

    • Kat Nguyen on Shopify: https://www.linkedin.com/in/katngy/

    • Dollar Shave Club ad: https://www.youtube.com/watch?v=ZUG9qYTJMsI

    The Daily Stoic: 366 Meditations on Wisdom, Perseverance, and the Art of Living: https://www.amazon.com/Daily-Stoic-Meditations-Wisdom-Perseverance/dp/0735211736

    Great by Choice: Uncertainty, Chaos, and Luck—Why Some Thrive Despite Them All: https://www.amazon.com/Great-Choice-Uncertainty-Luck-Why-Despite/dp/0062120999

    X-Men ’97 on Disney+: https://www.disneyplus.com/series/x-men-97/vc1XIz90ZNH5

    RRR on Netflix: https://www.netflix.com/title/81476453

    The Playlist on Netflix: https://www.netflix.com/title/81186296

    Welcome to Wrexham on Hulu: https://www.hulu.com/series/welcome-to-wrexham-c6906d50-d06c-40d1-a57c-1885d9dc2fef

    The Billion Dollar Code on Netflix: https://www.netflix.com/title/81074012

    • Magic Mind: https://magicmind.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.



    Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

    5 essential questions to craft a winning strategy | Roger Martin (author, advisor, speaker)

    5 essential questions to craft a winning strategy | Roger Martin (author, advisor, speaker)

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

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

    • Why most companies get strategy wrong

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

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

    • How to think about differentiation vs. low cost

    • Shortcomings of current strategy education

    • Much more

    Brought to you by:

    Webflow—The web experience platform

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    Cycle—Your feedback hub, on autopilot

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

    Where to find Roger Martin:

    • X: https://x.com/RogerLMartin

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

    • Website: https://rogerlmartin.com/

    Where to find Lenny:

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

    • X: https://twitter.com/lennysan

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

    In this episode, we cover:

    (00:00) Roger’s background

    (02:20) The importance of strategy

    (07:00) Challenges in developing strategy

    (08:30) Critique of modern strategy education

    (14:00) Hamilton Helmer and Richard Rumelt

    (17:40) Defining strategy

    (19:12) The Strategy Choice Cascade

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

    (24:57) Examples of strategic success

    (30:49) Differentiation and moats

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

    (43:47) Customer-centric strategy

    (44:45) Defining the market and product

    (45:59) Value chain and distribution

    (48:28) Cost leadership vs. differentiation

    (53:16) Capabilities and management systems

    (57:14) Competitive advantage and market positioning

    (01:02:41) Counterpositioning and fault lines

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

    (01:14:11) Betterment over perfection

    (01:18:42) Final thoughts on strategy

    Referenced:

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

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

    • Figma: https://www.figma.com/

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

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

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

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

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

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

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

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

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

    • Lego: https://www.lego.com

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

    Lenny may be an investor in the companies discussed.



    Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

    What most people miss about marketing | Rory Sutherland (Vice Chairman of Ogilvy UK, author)

    What most people miss about marketing | Rory Sutherland (Vice Chairman of Ogilvy UK, author)

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

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

    • Why less functionality can sometimes be more valuable

    • The importance of fame in building successful brands

    • The importance of timing in product success

    • The concept of “most advanced, yet acceptable”

    • Why metrics-driven workplaces can be demotivating

    • Lots of real-world case studies

    • Much more

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

    Brought to you by:

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

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

    Where to find Rory Sutherland:

    • X: https://x.com/rorysutherland

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

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

    Where to find Lenny:

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

    • X: https://twitter.com/lennysan

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

    In this episode, we cover:

    (00:00) Rory’s background

    (02:37) The success and failure of products

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

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

    (12:29) The MAYA principle

    (15:50) How thinking irrationally can be advantageous

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

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

    (30:31) “Psycho-logical” thinking

    (31:45) The hare and the dog metaphor

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

    (49:21) The quirks of Google Glass

    (55:44) Survivorship bias

    (56:09) Balancing rational ideas with irrational ideas

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

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

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

    (01:23:35) Where to find Rory

    Referenced:

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

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

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

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

    • Ogilvy: https://www.ogilvy.com/

    • MCI: https://www.mci.world/

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

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

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

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

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

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

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

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

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

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

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

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

    • AO: https://ao.com/

    • Zappos: https://www.zappos.com/

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

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

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

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

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

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

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

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

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

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

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

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

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

    • reMarkable: https://remarkable.com/

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

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

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

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

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

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

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

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

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

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

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

    • Nudgestock: https://nudgestock.com/

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

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

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

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

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

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

    • PwC: https://www.pwc.com

    • Ryanair: https://www.ryanair.com

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

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

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

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

    Lenny may be an investor in the companies discussed.



    Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

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