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    How to ask the right questions, project confidence, and win over skeptics | Paige Costello (Asana, Intercom, Intuit)

    Effective leaders are authentic and transparent, openly discussing challenges and vulnerabilities. They focus on skills and experiences rather than specific roles or companies, fostering a positive environment and being passionate about problem-solving.

    enJuly 09, 2023

    About this Episode

    Brought to you by Brave—The independent, global search index you can use to power your search or AI app | Attio—The powerful, flexible CRM for fast-growing startups | Round—The private network built by tech leaders for tech leaders

    Paige Costello is a beloved product leader with a reputation as a remarkable coach and mentor. She is currently the Head of Core Product at Asana, where she leads the group responsible for Asana’s web, desktop, and mobile apps. Prior to that role, she served as the Director of Product at Intercom and, before that, as a Group PM at Intuit, where she kickstarted her product career through their renowned APM program. In today’s episode, we discuss:

    • The unique product development process at Asana and how it’s evolved

    • The double-diamond framework

    • Conscious leadership training, and why every Asana employee learns it

    • How to demonstrate confidence and earn trust from skeptics

    • Why curiosity and openness may be the most important PM competencies

    • How to give feedback using impact statements

    Find the full transcript at: https://www.lennyspodcast.com/how-to-ask-the-right-questions-project-confidence-and-win-over-skeptics-paige-costello-asana-intercom-intuit/#transcript

    Where to find Paige Costello:

    • Twitter: https://twitter.com/paigenow

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

    Where to find Lenny:

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

    • Twitter: https://twitter.com/lennysan

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

    In this episode, we cover:

    (00:00) Paige’s background

    (04:38) What Paige is responsible for at Asana

    (06:04) The evolution of Asana’s product development process

    (09:10) Planning frequency

    (11:26) Examples of areas and metric tracking at Asana

    (12:46) The double-diamond process and how it’s applied at Asana

    (16:53) Asana’s office-centric hybrid work culture and the future of WFH

    (21:45) How to garner trust and win over skeptics

    (24:45) Why you should befriend researchers

    (26:17) How to exude confidence

    (29:03) The 3Es framework

    (33:43) Advice for early-career PMs

    (38:43) Paige’s latest pillars strategy

    (40:05) AI at Asana

    (41:50) Lessons from Paige’s time at Intuit

    (45:53) Challenges new PMs face

    (48:55) Challenges Paige has faced in her career

    (52:39) Paige’s skill-focused career philosophy

    (55:43) Lightning round

    Referenced:

    • Use This Equation to Determine, Diagnose, and Repair Trust: https://review.firstround.com/use-this-equation-to-determine-diagnose-and-repair-trust

    • About conscious leadership at Asana: https://wavelength.asana.com/workstyle-simple-shift/

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

    • Intuit: https://www.intuit.com/

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

    The Blind Assassin: https://www.amazon.com/Blind-Assassin-Novel-Margaret-Atwood/dp/0385720955

    The Alchemist: https://www.amazon.com/Alchemist-Paulo-Coelho/dp/0062315005

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

    Fire of Love on Disney+: https://www.disneyplus.com/movies/fire-of-love/1hC7erRfsl3B

    • Poe: https://poe.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

    🔑 Key Takeaways

    • Understanding customers, competitors, and numbers while adopting a mindset shift from scarcity thinking to exploring alternative options is crucial for young product managers to gain trust and succeed.
    • Asana's updated planning process focuses on accountability, adaptability, and shorter planning cycles, allowing for better alignment and increased confidence in the immediate future.
    • Asana emphasizes team-focused improvement and customer value through metrics and a data-driven decision-making process.
    • Asana's phased approach to product development and hybrid work model prioritize collaboration, flexibility, and maintaining mental health, resulting in increased productivity and positive team dynamics.
    • Understanding your productivity patterns, identifying your chronotype, and gaining expertise in your field are essential for success in remote work. Building trust through authenticity and customer focus is equally important.
    • Building trust and effective communication requires vulnerability, active engagement, and empathy. By understanding customers' needs and behaviors, asking questions, and actively participating, trust and collaboration can be fostered.
    • Constantly seeking opportunities to expand knowledge and skills, embracing open conversation and debate, and considering the bigger picture are vital for personal and leadership growth.
    • Being aware of our mindset and embracing technological transformations are crucial for effective decision-making and staying competitive in today's rapidly evolving world.
    • By prioritizing prototyping, customer centricity, and effective communication, product development teams can create better products, address customer problems, and drive impactful growth and success.
    • New product managers should focus on asking questions, seeking feedback, and solving problems instead of trying to be the expert in the room. By staying present, having fun, and learning from mistakes, they can naturally advance in their career.
    • Effective leaders are authentic and transparent, openly discussing challenges and vulnerabilities. They focus on skills and experiences rather than specific roles or companies, fostering a positive environment and being passionate about problem-solving.
    • By establishing clear ownership and accountability, teams can improve efficiency, connectivity, and ultimately, the execution of product development tasks.
    • Conduct a maximum of three reviews, prioritize decision notes, assign pre-read tasks, and utilize Asana's features to improve teamwork and productivity. Consider the potential of AI to enhance efficiency and alignment.

    📝 Podcast Summary

    Building trust and mindset shift for young product managers

    Building trust and winning over skeptics as a young person in a room is possible by bringing insight and knowledge. Paige emphasizes the importance of understanding the customer, market, competitors, numbers, and product. She also highlights the mindset shift needed for new product managers, moving from scarcity thinking to exploring alternative options and different paths. By challenging oneself to consider "How might the opposite be true?", one can feel more relaxed and open to multiple possibilities. The conversation also provides insights into Paige's role at Asana as a product lead and the focus on creating clarity for individuals, teams, and organizations. Additionally, it touches upon the evolution of Asana's product development process and the changes in strategy and planning over the years.

    Asana's Revised Planning Process: Introducing "Area Perspective" and Shifting to Six-Month Planning Cycles.

    Asana has made significant changes to their planning process, particularly in terms of altitudes and time horizons. They have introduced an intermediary layer called "area perspective" to create more agency and accountability for teams focused on specific target customers and problems. This nested structure includes pillars, areas, and working teams, each with their own metrics and goals. They have shifted from planning annually to planning every six months for a rolling 12 month period. This allows for greater confidence in the immediate future and better alignment between go-to-market and product planning. The frequent reflection and ability to pivot quickly reduces churn and thrash, making the best use of the teams. Quarterly plans and sprints are not heavily emphasized, as teams prioritize success and iterative, prototyping-based approaches over strict timelines. Overall, Asana acknowledges the need for flexibility and adaptation in their planning process.

    Asana's strategic approach to team improvement and customer-focused decision-making.

    Asana has a detailed six-month plan for each team, ensuring that they focus on specific areas of improvement and set metrics to measure success. One example of an area is the Coordinate team, responsible for making sure that the collaboration features in Asana function effectively. The metrics they care about include weekly active users and healthy project use, indicating that the company prioritizes providing real value to its users. Additionally, the conversation reveals that Asana follows a process called the Double Diamond Process, which involves going broad and then narrowing down to define problems and solutions. This process helps the company make data-driven and customer-targeted decisions, ensuring that their product thinking is effective and focused on solving customer problems.

    Asana's Phased Approach to Product Development and Hybrid Work Model for Collaboration and Flexibility

    Asana follows a phased approach to product development, starting with a kickoff and direction selection, followed by going broad on different concepts, design concept review, product specs, and a full experience review before launch. The reviews and discussions happen both in person and asynchronously, depending on the complexity and ambiguity of the solution. In terms of work-from-home policy, Asana adopted an office-centric hybrid format, where employees work in the office on specific days and work from home on others. This approach allows for collaboration and quick decision-making while providing flexibility and maintaining mental health by fostering social relationships and casual discussions. Overall, creating a balance between in-person and remote work has proved beneficial for productivity and team dynamics at Asana.

    Maximizing Productivity and Building Trust in Remote Work Environments

    Understanding your own productivity patterns and leveraging them effectively can have a significant impact on your work. Remote working days can be more impactful for deep work compared to days spent in the office. Identifying your chronotype, whether you are a morning person or not, can help in scheduling important tasks during the time of day when you have the most headspace. Additionally, building trust and winning over skeptics can be accomplished by bringing valuable insights and knowledge to the table. By being the person in the room who understands customers, the market, competitors, and product intricacies, you can establish credibility and create curiosity among others. Doing the work, spending time with customers, and developing authenticity are crucial factors in winning trust.

    Fostering Trust and Effective Communication through Vulnerability and Engagement

    Building trust and effective communication require vulnerability and active engagement. It's important to understand the needs and behaviors of customers, rather than assuming that one's own perspective is representative of the entire customer base. By asking questions and listening to insights, the nature of conversations can be changed, fostering trust and collaboration. Confidence is not about being assertive all the time, but about being willing to ask questions and admit when one doesn't know something. Real confidence is conveyed through open communication, body language, and actively participating in meetings. Leading and teaching by example, through repetition and experience, can be more successful in mentoring and coaching others compared to simply giving instructions. By embodying the desired behaviors, others are more likely to remember and internalize them.

    The importance of being a learner in various contexts and its impact on personal growth and development.

    Being a learner in various contexts, such as education, experience, and exposure, can greatly contribute to personal growth and development. Paige Costello emphasizes the importance of being present and analytical, as well as actively seeking opportunities to expand knowledge and skills. She exemplifies this by running meetings in a way that encourages open conversation and debate, while prioritizing the experience of everyone involved. Additionally, she shares an insightful piece of advice she received during a high-stakes product review, which highlights the importance of answering the underlying questions and considering the bigger picture. Paige also offers advice to others, including not self-selecting based on perceived limitations and encouraging a balanced approach of thinking big and shipping small. Ultimately, a combination of experience, exposure, and education can lead to conscious and effective leadership.

    The Impact of Mindset on Decision-Making and Embracing Technological Transformations

    It is important to be aware of our mindset and how it impacts our decision-making process. The concept of being "above the line" or "below the line" highlights the difference between being open to learning and being focused on winning or being right. Understanding our personal head space and being mindful of how we operate in that space can greatly influence our interactions and decision-making. Additionally, challenging ourselves with the question "How might the opposite be true?" can help us break free from a scarcity mindset and explore alternative options. This conversation also emphasizes the significance of embracing technological transformations, such as AI, and allocating resources for exploration and prototyping to stay on the cutting edge and effectively serve customers.

    The Importance of Prototyping, Customer Centricity, and Communication in Product Development

    A key factor in successful product development is the ability to quickly prototype and test ideas. By bypassing lengthy planning processes and going straight to prototyping, teams can gain valuable insights and discover opportunities that they may have overlooked otherwise. This approach allows for faster iteration and validation of ideas, leading to the creation of better products. Additionally, it's crucial to prioritize customer centricity and gather insights by observing and understanding how customers interact with a product. By embracing customer feedback and basing decisions on their needs and pain points, teams can create products that truly address customer problems and deliver value. Effective communication and feedback delivery are also essential skills for managers to foster growth and success within their teams. Soft skills like giving feedback and effective communication are just as important, if not more, than technical skills in driving impactful product development.

    Embracing curiosity and openness: the key to success for new product managers

    New product managers often feel the pressure to be all-knowing and confident, leading to a mindset of advocacy rather than inquiry. This mindset can hinder collaboration and inhibit growth. It is important for new PMs to embrace curiosity and openness, allowing for a more successful experience. Instead of trying to be the expert in the room, they should focus on asking clarifying questions and seeking feedback. Additionally, PMs should not let ambition consume them, but rather find enjoyment in their job and focus on solving problems. By staying present, having fun, and producing positive outcomes, opportunities for promotion and advancement will naturally arise. Mistakes will be made along the way, but taking ownership and learning from them is crucial. One common misstep is striking a balance between giving guidance and micromanaging. Developing techniques to manage this, such as writing down thoughts before meetings and allowing others to speak first, can be beneficial.

    The Importance of Authenticity and Transparency in Leadership

    Effective leadership requires being authentic and transparent, even when delivering bad news or addressing problems. Paige Costello shares her experience of being perceived as inauthentic because she focused on highlighting the positive aspects and didn't openly address the challenges. She emphasizes the importance of being "real" with oneself and others, showing vulnerabilities, and openly discussing the incomplete or imperfect aspects of a project. Additionally, when planning one's career path, Paige advises focusing on skills and experiences rather than specific roles or companies. She highlights the significance of a steep learning curve, a positive environment that fosters growth and support, and being passionate about the problem being solved. Being intentional and present in the current career journey is essential, rather than solely looking towards the future.

    Streamlining the Review and Approval Process: Creating Agency and Pace in Product Development

    Being intentional and proactive about structuring the product development process can have a significant impact on a team's ability to execute. Paige Costello shares how her team implemented changes to streamline the review and approval process, clearly defining roles and responsibilities. By setting limits on the number of reviewers and approvals, they created more agency and pace within the working teams. This approach reduced the need for excessive reviews and daisy chains of approvals, allowing for faster decision-making and progress. The key lesson here is that establishing clear ownership and accountability can improve efficiency and enable better connectivity within the team, leading to more effective execution of product development tasks.

    Maximizing Meeting Efficiency and Collaboration with Asana

    A maximum of three reviews should be conducted on a piece of work where only one person is blocking its progress. Meetings with more than 10 people should prioritize decision notes and remove unnecessary participants. Asana can be effectively used to manage meetings and assign pre-read tasks using the multi-assign feature in subtasks. Live note-taking in a task allows for the easy conversion of important points into subtasks, ensuring that action items are not overlooked. Asana's features can be utilized to build and run teams efficiently. AI has the potential to shape the future of software for knowledge workers, and feedback on how AI can enhance efficiency and alignment in Asana would be valuable.

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    Kenneth Berger coaches startup leaders on how to prevent burnout, advocate for their desired lifestyle, and make a meaningful impact on the world. He’s spent more than 20 years in the tech industry, is a former founder backed by top investors, and was the first product manager at Slack. Kenneth’s core mission is to help startup leaders change the world by learning to ask for what they want, living with integrity, and building genuine relationships even with the people they find most challenging. Currently he is writing a book, Ask for What You Want, in which he aims to share his actionable strategies for creating change in the world. In our conversation, we explore:

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    • Three steps to effectively ask for what you want

    • Challenges that arise when people struggle to ask for what they want

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    Where to find Kenneth Berger:

    • X: https://twitter.com/kberger

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

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

    • Website: https://kberger.com/

    Where to find Lenny:

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

    • X: https://twitter.com/lennysan

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

    In this episode, we cover:

    (00:00) Kenneth’s background

    (04:31) The importance of asking for what you want

    (06:36) Challenges that arise when people struggle to ask for what they want

    (08:09) A personal example of failing to ask for what you want

    (09:17) Signs this is a skill you need to work on

    (10:49) How to get better at knowing what you want

    (15:28) Why hearing “no” is a normal part of the process

    (17:29) Getting a “yes” vs. a “hell yes”

    (19:20) Step 1: Articulate what you want

    (24:07) Doing an integrity check

    (26:56) Step 2: Ask for what you want intentionally

    (30:45) Understanding your influence

    (34:48) Using complaints as inspiration

    (36:24) Internal family systems

    (38:00) Giving feedback

    (41:24) Step 3: Accept the response

    (45:22) Kenneth’s experience of being fired three times from Slack

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    (01:05:52) Lightning round

    Referenced:

    • Joining as the first product manager: https://www.lennysnewsletter.com/p/joining-as-the-first-product-manager

    • Internal Family Systems: https://ifs-institute.com/

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

    • Leaders in Tech: https://leadersintech.org/

    • The Three Realities Framework | The 15% Rule | Feedback Guidelines: https://www.lennysnewsletter.com/p/build-robust-relationships-carole-robin

    • T-group weekends at Stanford: https://www.gsb.stanford.edu/experience/learning/leadership/interpersonal-dynamics/facilitation-training-program/intro-tgroup

    • DBT skill DEAR MAN: https://www.therapistaid.com/therapy-worksheet/dbt-dear-man

    • Dialectical behavior therapy (DBT): https://my.clevelandclinic.org/health/treatments/22838-dialectical-behavior-therapy-dbt

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

    • Stewart Butterfield on LinkedIn: https://www.linkedin.com/in/butterfield/

    • How to fire people with grace, work through fear, and nurture innovation | Matt Mochary (CEO coach): https://www.lennysnewsletter.com/p/how-to-fire-people-with-grace-work

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

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

    • Jonny Miller’s Nervous System Mastery course: https://nsmastery.com/lenny

    • Managing nerves, anxiety, and burnout | Jonny Miller (Nervous System Mastery): https://www.lennysnewsletter.com/p/managing-nerves-anxiety-and-burnout

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

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

    Living on Netflix: https://www.netflix.com/title/81582076

    • Wimbledon tennis: https://www.wimbledon.com

    • Wenshan Baozhong tea: https://redblossomtea.com/products/wenshan-baozhong?variant=31629962820

    • Tea From Taiwan: https://www.teafromtaiwan.com/

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    Lenny may be an investor in the companies discussed.



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

    Be fundamentally different, not incrementally better | Jag Duggal (Nubank, Facebook, Google, Quantcast)

    Be fundamentally different, not incrementally better | Jag Duggal (Nubank, Facebook, Google, Quantcast)

    Jag Duggal is chief product officer at Nubank, a decacorn neobank founded in Brazil. It’s valued at over $30 billion, is bigger than Coinbase, Robinhood, Affirm, and SoFi combined, has 100 million customers (more than Bank of America!) while only operating in three countries in Latin America, and 80% to 90% of its growth comes through word of mouth. Prior to Nubank, Jag was a director of product management at Facebook, a senior vice president at Quantcast, and a product leader at Google. In our conversation, we discuss:

    • How Nubank builds a fanatical user base

    • Tactics for driving word-of-mouth growth

    • Measuring customer love through the Sean Ellis score

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    • Nubank’s vision for an AI-powered banking future

    Brought to you by:

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

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    Where to find Jag Duggal:

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

    Where to find Lenny:

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

    • X: https://twitter.com/lennysan

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

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    Referenced:

    • Nubank: https://nubank.com.br/en/

    • Coinbase: https://www.coinbase.com/

    • Robinhood: https://www.robinhood.com/

    • SoFi: https://www.sofi.com/

    • Affirm: https://www.affirm.com/

    • Lemonade: https://www.lemfi.com/

    • Bank of America: https://www.bankofamerica.com/

    • Nubank achieves a world record with more than 7 million people participating in NuBolão in one month: https://building.nubank.com.br/nubank-achieves-world-record-with-nubolao

    • Nu México carries out first financial transaction 20 meters under the depth of the sea: https://www.bnamericas.com/en/news/nu-mexico-carries-out-first-financial-transaction-20-meters-under-the-depth-of-the-sea

    • David Vélez on LinkedIn: https://www.linkedin.com/in/david-v%C3%A9lez-1004875

    • Cristina Junqueira on LinkedIn: https://www.linkedin.com/in/crisjunqueira

    • Edward Wible on LinkedIn: https://www.linkedin.com/in/adamedwardwible

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

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

    • Nubank’s real foundation: our culture and values: https://building.nubank.com.br/nubank-culture-and-values/

    • Working Backwards Press Release Template and Example: https://www.linkedin.com/pulse/working-backwards-press-release-template-example-ian-mcallister/

    • Sean Ellis test: https://productcoalition.com/using-sean-ellis-test-for-measuring-your-product-market-fit-c8ac98053c2c

    • How to know if you’ve got product-market fit: https://www.lennysnewsletter.com/p/how-to-know-if-youve-got-productmarket

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

    • Ultravioleta: Nubank expands its premium card offer and adds new features on the product’s first anniversary: https://international.nubank.com.br/company/ultravioleta-nubank-expands-its-premium-card-offer-and-adds-new-features-on-the-products-first-anniversary/

    • Jeff Bezos: Amazon and Blue Origin | Lex Fridman Podcast #405: https://www.youtube.com/watch?v=DcWqzZ3I2cY

    • The Innovation Method Behind Swiffer Madness: https://www.fastcompany.com/3006797/innovation-method-behind-swiffer-madness

    • Kevin Systrom on LinkedIn: https://www.linkedin.com/in/kevinsystrom/

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

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

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

    • How to become a category pirate | Christopher Lochhead (author of Play Bigger, Niche Down, Category Pirates, more): https://www.lennysnewsletter.com/p/how-to-become-a-category-pirate-christopher

    Play Bigger: How Pirates, Dreamers, and Innovators Create and Dominate Markets: https://www.amazon.com/Play-Bigger-Dreamers-Innovators-Dominate/dp/0062407619

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

    • A framework for finding product-market fit | Todd Jackson (First Round Capital): https://www.lennysnewsletter.com/p/a-framework-for-finding-product-market

    • Citi: https://www.citi.com/

    • Santander Bank: https://www.santanderbank.com/

    • Fidji Sumo on LinkedIn: https://www.linkedin.com/in/fidjisimo/

    • Harvard Kennedy School: https://www.hks.harvard.edu/

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    • Coldplay—“Lost+” ft. Jay-Z: https://www.youtube.com/watch?v=PkCDRm_YRFg

    • Google Buys DoubleClick for $3.1 Billion: https://www.nytimes.com/2007/04/14/technology/14DoubleClick.html

    • Real-time bidding: https://support.google.com/authorizedbuyers/answer/6136272

    From Third World to First: The Singapore Story: 1965-2000: https://www.amazon.com/Third-World-First-Singapore-1965-2000/dp/0060197765/

    The Gilded Age on HBO: https://www.hbo.com/the-gilded-age

    • Lomi: https://lomi.com/

    • Nubank careers: https://international.nubank.com.br/careers/

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

    Lenny may be an investor in the companies discussed.



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

    A framework for PM skill development | Vikrama Dhiman (Gojek)

    A framework for PM skill development | Vikrama Dhiman (Gojek)

    Vikrama Dhiman heads all things product at Gojek, including product management, design, program management, and research, across Indonesia, Singapore and India. He has over 16 years of experience building internet products, consults with Fortune 500 companies, and is among the most well-known and respected product leaders in all of Asia. In our conversation, we discuss:

    • The most common traits among successful product managers

    • The 3 W’s framework for PM career growth

    • The Four A’s of leveling up in product management

    • The right way to push back as a PM

    • Common pitfalls that stall PM careers

    • Vikrama’s advice for transitioning into product management

    • Why intent alone is not enough

    Brought to you by:

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    Find the transcript at: https://www.lennysnewsletter.com/p/a-framework-for-pm-skill-development

    Where to find Vikrama Dhiman:

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

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

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

    Where to find Lenny:

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

    • X: https://twitter.com/lennysan

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

    In this episode, we cover:

    (00:00) Vikrama’s background

    (03:56) Three common traits among great PMs

    (07:09) The first W: What you produce

    (15:40) The second W: What you bring to the table

    (18:58) The third W: What’s your operating model?

    (20:36) Three traits that make you a great PM to work with

    (21:49) How to improve the quality and quantity of your outputs

    (23:26) The art of the pushback

    (26:55) Common factors that impede career growth

    (33:39) Vikrama’s personal reflections

    (39:33) Choosing which skill(s) to focus on developing

    (46:28) The ambiguity of the PM role

    (51:47) The 8 axis for PM growth

    (56:57) Contrarian corner: Why intent alone is not enough

    (59:30) Lightning round

    Referenced:

    • Taxi mafias, cash vaults, and 100% MoM growth: The story behind Southeast Asia’s biggest startup | Kevin Aluwi (Gojek): https://www.lennysnewsletter.com/p/taxi-mafias-cash-vaults-and-100-mom

    • How to scrappily hire for, measure, and unlock growth | Crystal Widjaja, Gojek and Kumu: https://www.lennysnewsletter.com/p/how-to-hire-for-measure-and-unlock

    • Gojek: https://www.gojek.com/en-id

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

    • Oracle: https://www.oracle.com/

    • Crystal Widjaja on LinkedIn: https://www.linkedin.com/in/crystalwidjaja

    • Raditya Wibowo: https://www.linkedin.com/in/raditya-wibowo-a0845436/?originalSubdomain=id

    • Sidu Ponnappa on LinkedIn: https://www.linkedin.com/in/sidup

    • Leveraging mentors to uplevel your career | Jules Walter (YouTube, Slack): https://www.lennysnewsletter.com/p/leveraging-mentors-to-uplevel-your

    • Kevin Aluwi on LinkedIn: https://www.linkedin.com/in/kaluwi/

    • Workday: https://www.workday.com/

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

    Small Data: The Tiny Clues That Uncover Huge Trends: https://www.amazon.com/Small-Data-Clues-Uncover-Trends/dp/1250080681

    Originals: How Non-Conformists Move the World: https://www.amazon.com/Originals-How-Non-Conformists-Move-World/dp/014312885X

    Thinking, Fast and Slow: https://www.amazon.com/Thinking-Fast-Slow-Daniel-Kahneman/dp/0374533555

    Miss Congeniality on Prime Video: https://www.amazon.com/Miss-Congeniality-Sandra-Bullock/dp/B002R5HQDK

    Schitt’s Creek on Prime Video: https://www.amazon.com/Schitts-Creek/dp/B083LDRW9F

    • DramaBox: https://www.dramaboxapp.com/

    Am I Overthinking This?: Over-Answering Life’s Questions in 101 Charts: https://www.amazon.com/Am-Overthinking-This-Over-answering-questions/dp/1452175861/

    Crazy Rich Asians on Prime Video: https://www.amazon.com/Crazy-Rich-Asians-Constance-Wu/dp/B07JGJFXBF

    • 9 Best Hawker Centers in Singapore—and What to Eat There: https://www.afar.com/magazine/best-hawker-centers-in-singapore-and-what-to-eat-there

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

    Lenny may be an investor in the companies discussed.



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

    Business strategy with Hamilton Helmer (author of 7 Powers)

    Business strategy with Hamilton Helmer (author of 7 Powers)

    Hamilton Helmer is one of the world’s leading experts on business strategy and the author of the seminal book 7 Powers: The Foundations of Business Strategy, which provides a comprehensive framework for understanding what it really takes to achieve and sustain a competitive advantage. With more than three decades of experience in the strategic consulting industry, Hamilton has advised over 200 companies—from burgeoning startups to Fortune 100 giants—on how to identify, build, and leverage their unique strategic powers. In our conversation, we discuss:

    • Potential sources of power that startups should develop from an early stage

    • Common misconceptions among companies about the types of power they possess

    • How power relates to strategy

    • The difference between a moat and a power

    • Practical strategies for non-leaders to leverage insights about power and strategy in their work

    • AI’s impact on competitive advantages and barriers to entry

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    Find the transcript and references at: https://www.lennysnewsletter.com/p/business-strategy-with-hamilton-helmer

    Where to find Hamilton Helmer:

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

    • LinkedIn: https://www.linkedin.com/in/hamilton-helmer-42983/

    • Website: https://7powers.com/

    Where to find Lenny:

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

    • X: https://twitter.com/lennysan

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

    In this episode, we cover:

    (00:00) Hamilton’s background

    (04:08) When power becomes important

    (08:24) How strategy relates to power

    (12:09) How power informs strategy

    (14:46) The sequence of powers

    (21:13) Common misconceptions

    (24:39) Network effects vs. network economies

    (26:58) Uber’s success

    (29:16) Moats vs. powers

    (31:12) Strategies for non-leaders to leverage power and strategy

    (37:51) Advice on how to become a strategic thinker

    (39:27) AI’s impact on the seven powers

    (45:43) Why moving fast is not a power

    (50:24) Three things that create value in a company

    (51:16) The debt trajectory of the U.S.

    (56:35) Optimism for the future

    (59:25) Lightning round

    Referenced:

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

    • John von Neumann: https://en.wikipedia.org/wiki/John_von_Neumann

    • Pearl Harbor: https://www.history.com/topics/world-war-ii/pearl-harbor

    • Where the Japanese Went Wrong at Pearl Harbor: https://pearlharbor.org/blog/where-japanese-went-wrong-pearl-harbor/

    • The ‘7 Powers’ of business success—from one of Netflix’s early investors: https://www.qualitycompounders.com.au/post/the-7-powers-of-business-success-from-one-of-netflix-s-early-investors

    • 7 Powers: Foundations of Business Strategy (Key Takeaways): https://www.linkedin.com/pulse/7-powers-foundations-business-strategy-key-takeaways-nikita-maloo/

    • Strategy Capital: https://strategycapital.com/

    • Warren Buffett: https://www.forbes.com/profile/warren-buffett/

    • Charlie Munger: https://www.forbes.com/profile/charles-munger/

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

    • Bill Gates reveals why Warren Buffett was an invaluable source of support during the stormiest period of his career: https://www.businessinsider.com/bill-gates-interview-warren-buffett-support-microsoft-antitrust-lawsuit-2019-6

    •  Billionaire Warren Buffett’s Secret Love Affair With Castles, Revealed: https://www.thestreet.com/opinion/billionaire-warren-buffett-s-secret-love-affair-with-castles-revealed-14290973

    • Netflix didn’t kill Blockbuster—how Netflix almost lost the movie rental wars: https://www.cnbc.com/2020/09/22/how-netflix-almost-lost-the-movie-rental-wars-to-blockbuster.html

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

    • What Is Strategy?: https://hbr.org/1996/11/what-is-strategy

    • TSMC: https://www.tsmc.com/english

    • Toyota Production System: https://en.wikipedia.org/wiki/Toyota_Production_System

    • America will be left with ‘severe, irreversible scars’ if national debt goes unchecked. Now, a blockbuster report warns the bill is higher than believed, hitting $141T by 2054: https://fortune.com/2024/04/01/america-social-economic-scars-us-debt-gomes-price/

    • Ben S. Bernanke: https://www.federalreservehistory.org/people/ben-s-bernanke

    • Forty-four of 50 U.S. states worsen inequality with ‘upside-down’ taxes: https://www.theguardian.com/us-news/2024/jan/10/states-wealth-inequality-taxes

    • Joseph A. Schumpeter: https://en.wikipedia.org/wiki/Joseph_Schumpeter

    Theory of Economic Development: https://www.amazon.com/Theory-Economic-Development-Science-Classics/dp/0878556982

    The Road to Reality: A Complete Guide to the Laws of the Universe: https://www.amazon.com/Road-Reality-Complete-Guide-Universe/dp/0679776311

    The Gene: An Intimate History: https://www.amazon.com/Gene-Intimate-History-Siddhartha-Mukherjee/dp/147673352X

    American Fiction on Prime Video: https://www.amazon.com/American-Fiction-Jeffrey-Wright/dp/B0CQKR72NX

    • Farahan Sarouk rugs: https://nazmiyalantiquerugs.com/persian-sarouk-farahan-rugs/

    • Rory Sutherland on LinkedIn: https://www.linkedin.com/in/rorysutherland

    • Ogilvy: https://www.ogilvy.com/

    • Clint Eastwood quote: https://www.brainyquote.com/quotes/clint_eastwood_168005

    • Winston Churchill: https://en.wikipedia.org/wiki/Winston_Churchill

    Michelangelo, God’s Architect: The Story of His Final Years and Greatest Masterpiece: https://www.amazon.com/Michelangelo-Gods-Architect-Greatest-Masterpiece/dp/0691195498

    The Last Judgment: https://en.wikipedia.org/wiki/The_Last_Judgment_(Michelangelo)

    • Theodore Roosevelt: https://www.whitehouse.gov/about-the-white-house/presidents/theodore-roosevelt/

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

    Lenny may be an investor in the companies discussed.



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

    This will make you a better decision maker | Annie Duke (author of “Thinking in Bets” and “Quit”, former pro poker player)

    This will make you a better decision maker | Annie Duke (author of “Thinking in Bets” and “Quit”, former pro poker player)

    Annie Duke is a former professional poker player, a decision-making expert, and a special partner at First Round Capital. She is the author of Thinking in Bets (a national bestseller) and Quit: The Power of Knowing When to Walk Away and the co-founder of the Alliance for Decision Education, a nonprofit whose mission is to improve lives by empowering students through decision skills education. In our conversation, we cover:

    • What Annie learned from the late Daniel Kahneman

    • The power of pre-mortems and “kill criteria”

    • The relationship between money and happiness

    • The power of “mental time travel”

    • The nominal group technique for better decision quality

    • How First Round Capital improved their decision-making process

    • Many tactical decision-making frameworks

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    Find the transcript at: https://www.lennysnewsletter.com/p/making-better-decisions-annie-duke

    Where to find Annie Duke:

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

    • LinkedIn: https://www.linkedin.com/in/annie-duke/

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

    • Substack: https://www.annieduke.com/substack/

    Where to find Lenny:

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

    • X: https://twitter.com/lennysan

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

    In this episode, we cover:

    (00:00) Annie’s background

    (03:53) Lessons from Daniel Kahneman: humility, curiosity, and open-mindedness

    (09:15) The importance of unconditional love in parenting

    (15:15) Mental time travel and “nevertheless”

    (20:06) The extent of improvement possible in decision-making 

    (24:54) Independent brainstorming for better decisions

    (35:36) Making sure people feel heard

    (42:41) The “3Ds” framework to make better decisions

    (44:49) Decision quality

    (55:46) Improving decision-making at First Round Capital

    (01:05:05) Using pre-mortems and kill criteria

    (01:10:15) Making explicit what’s implicit

    (01:10:55) The challenges of quitting and knowing when to walk away

    (01:19:23) Where to find Annie

    Referenced:

    • Daniel Kahneman, Who Plumbed the Psychology of Economics, Dies at 90: https://www.nytimes.com/2024/03/27/business/daniel-kahneman-dead.html

    • Adversarial collaboration: https://en.wikipedia.org/wiki/Adversarial_collaboration

    • Does more money correlate with greater happiness?: https://penntoday.upenn.edu/news/does-more-money-correlate-greater-happiness-Penn-Princeton-research#

    • Income and emotional well-being: A conflict resolved: https://pubmed.ncbi.nlm.nih.gov/36857342/

    • Strategic decisions: When can you trust your gut?: https://www.mckinsey.com/capabilities/strategy-and-corporate-finance/our-insights/strategic-decisions-when-can-you-trust-your-gut

    • Cass Sunstein on X: https://twitter.com/CassSunstein

    • Dr. Becky on Instagram: https://www.instagram.com/drbeckyatgoodinside

    • A framework for finding product-market fit | Todd Jackson (First Round Capital): https://www.lennysnewsletter.com/p/a-framework-for-finding-product-market

    • First Round Capital: https://firstround.com/

    • Brett Berson on X: https://twitter.com/brettberson

    • Renegade Partners: https://www.renegadepartners.com/

    • Renata Quintini on X: https://twitter.com/rquintini

    • Roseanne Wincek on X: https://twitter.com/imthemusic

    • Josh Kopelman on X: https://twitter.com/joshk

    • Bill Trenchard on X: https://twitter.com/btrenchard

    • Linnea Gandhi on X: https://twitter.com/linneagandhi

    • Maurice Schweitzer on X: https://twitter.com/me_schweitzer

    • Problems with premortems: https://sjdm.org/presentations/2021-Poster-Gandhi-Linnea-debiasing-premortem-selfserving~.pdf

    • Create a Solid Plan on How to Fail Big This Year: https://www.forbes.com/sites/forbesfinancecouncil/2020/02/07/create-a-solid-plan-on-how-to-fail-big-this-year/

    Quit: The Power of Knowing When to Walk Away: https://www.amazon.com/Quit-Power-Knowing-When-Walk/dp/0593422996/

    • Richard Thaler on X: https://twitter.com/R_Thaler

    • Stewart Butterfield on X: https://twitter.com/stewart

    • Glitch: https://en.wikipedia.org/wiki/Glitch_(video_game)

    • How the Founder of Slack & Flickr Turned Colossal Failures into Billion-Dollar Companies: https://medium.com/swlh/how-the-founder-of-slack-flickr-turned-failures-into-million-and-billion-dollar-companies-7bcaf0d35d66

    • The Most Fascinating Profile You’ll Ever Read About a Guy and His Boring Startup: https://www.wired.com/2014/08/the-most-fascinating-profile-youll-ever-read-about-a-guy-and-his-boring-startup/

    • The Alliance for Decision Education: https://alliancefordecisioneducation.org/

    • Make Better Decisions course on Maven: https://maven.com/annie-duke/make-better-decisions

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

    Lenny may be an investor in the companies discussed.



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

    Twitter’s former Head of Product opens up: being fired, meeting Elon, changing stagnant culture, building consumer product, more | Kayvon Beykpour

    Twitter’s former Head of Product opens up: being fired, meeting Elon, changing stagnant culture, building consumer product, more | Kayvon Beykpour

    Kayvon Beykpour was the longest-serving head of product at Twitter and was GM of Twitter’s consumer division until the platform was acquired by Elon Musk. He originally joined Twitter in 2015 through the acquisition of his company, Periscope, the largest live video streaming platform at the time. Periscope pioneered technology that inspired Instagram Live, TikTok Live, Facebook Live, and other social networks’ expansion into video streaming. In our conversation, we discuss:

    • The story of being let go from Twitter after Elon’s acquisition

    • How he turned Twitter’s stagnant culture around

    • Kayvon’s thoughts on the limitations of frameworks like Jobs to Be Done

    • Why Periscope failed

    • Advice for building consumer products

    • When to copy, when to innovate

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    Find the transcript at: https://www.lennysnewsletter.com/p/twitters-former-head-of-product-kayvon-beykpour

    Where to find Kayvon Beykpour:

    • X: https://twitter.com/kayvz

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

    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) Kayvon’s background

    (04:31) Getting Elon up to speed at Twitter

    (11:34) The story of being let go from Twitter after Elon’s acquisition

    (21:09) Changing the product culture at Twitter

    (29:44) Building the “hide replies” feature

    (32:02) Sacred crows, taking bold bets, and reigniting growth

    (34:28) Aquihires and their impact

    (42:40) Tips for successful acquisitions and staffing

    (47:00) The limitations of frameworks like JTBD

    (53:20) Signs you’ve gone too far with a framework

    (57:44) Lessons from building Periscope

    (01:00:41) Reasons why Periscope failed

    (01:07:24) The challenges of implementing video at Twitter

    (01:12:05) Copying ideas in good taste

    (01:17:58) How to get better at building consumer products

    (01:19:51) What Kayvon is building

    (01:20:31) Lightning round

    Referenced:

    • Lessons on building product sense, navigating AI, optimizing the first mile, and making it through the messy middle | Scott Belsky (Adobe, Behance): https://www.lennyspodcast.com/lessons-on-building-product-sense-navigating-ai-optimizing-the-first-mile-and-making-it-through-t/

    • What it’s like to sell your startup for ~$120 million before it’s even launched: Meet Twitter’s new prized possession, Periscope: https://www.businessinsider.com/what-is-periscope-and-why-twitter-bought-it-2015-3

    • Walter Isaacson on LinkedIn: https://www.linkedin.com/in/walter-isaacson-b8b81520/

    • Elon Musk on X: https://twitter.com/elonmusk

    • Parag Agrawal on LinkedIn: https://www.linkedin.com/in/parag-agrawal-5a14742a/

    • Jack Dorsey on LinkedIn: https://www.linkedin.com/in/jack-dorsey-a43b07242/

    • Blackboard: https://en.wikipedia.org/wiki/Blackboard_Inc.

    • Keith Coleman on X: https://twitter.com/kcoleman

    • Esther Crawford on LinkedIn: https://www.linkedin.com/in/esthercrawford/

    • Twitter acquires Chroma Labs: https://tech.hindustantimes.com/tech/news/twitter-acquires-chroma-labs-story-aqvcRPAoYXqXJuAbefA6cN.html

    • John Barnett on LinkedIn: https://www.linkedin.com/in/johnbarnettt/

    • Jobs to Be Done framework: https://jobs-to-be-done.com/jobs-to-be-done-a-framework-for-customer-needs-c883cbf61c90

    • Hot takes and techno-optimism from tech’s top power couple: https://www.lennyspodcast.com/hot-takes-and-techno-optimism-from-techs-top-power-couple-sriram-and-aarthi/

    • Nike Is Unveiling the Kobe 11 Tomorrow Using Periscope: https://sneakernews.com/2015/12/13/nike-is-unveiling-the-kobe-11-tomorrow-using-periscope/

    • Chris Sacca’s website: https://chrissacca.com/

    • Facebook Live: https://www.facebook.com/formedia/tools/facebook-live

    • Kevin Hart on X: https://twitter.com/KevinHart4real

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

    • Vine: https://en.wikipedia.org/wiki/Vine_(service)

    • Paul Davison on LinkedIn: https://www.linkedin.com/in/davison/

    • Rohan Seth on LinkedIn: https://www.linkedin.com/in/rohanseth/

    Cryptonomicon: https://www.amazon.com/Cryptonomicon-Neal-Stephenson/dp/0380788624

    Reamde: https://www.amazon.com/Reamde-Novel-Neal-Stephenson-ebook/dp/B004XVN0WW

    The Name of the Wind: https://www.amazon.com/Name-Wind-Kingkiller-Chronicle-Book-ebook/dp/B0010SKUYM

    Star Trek official site: https://www.startrek.com/

    Dune: part 2: https://www.dunemovie.com/

    Oppenheimer on Peacock: https://www.peacocktv.com/stream-movies/oppenheimer

    • Tokyo Vice on Max: https://www.max.com/shows/tokyo-vice/e7d93204-7f98-4e62-ab52-6c1da053f942

    Devs on Hulu: https://www.fxnetworks.com/shows/devs

    • Nick Offerman on X: https://twitter.com/nick_offerman

    3 Body Problem on Netflix: https://www.netflix.com/title/81024821

    • Perplexity AI: https://www.perplexity.ai/

    • Particle: https://www.particle.news/

    • Crokinole board game: https://boardgamegeek.com/boardgame/521/crokinole

    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 build deeper, more robust relationships | Carole Robin (Stanford GSB professor, “Touchy Feely”)

    How to build deeper, more robust relationships | Carole Robin (Stanford GSB professor, “Touchy Feely”)

    Carole Robin spent over 20 years teaching the Stanford Graduate School of Business course Interpersonal Dynamics, affectionately known as “Touchy Feely.” After leaving Stanford, she founded a nonprofit called Leaders in Tech, which applies the Touchy Feely principles to help Silicon Valley executives build their leadership and interpersonal skills. Carole co-authored the popular book Connect: Building Exceptional Relationships with Family, Friends, and Colleagues, which shares key insights from her decades of teaching these courses. In our conversation, we discuss:

    • The benefits of building robust relationships, in life and work

    • The 15% rule, and how it will help you build better relationships

    • The power of vulnerability

    • Examples of how to practice vulnerability

    • Why mental models you build early in life hold you back later

    • The “three realities” and “the net”

    • The art of inquiry

    • Practical tips for avoiding defensiveness when getting feedback

    • The impact of long Covid on Carole’s life

    Brought to you by:

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    Find the transcript at: https://www.lennysnewsletter.com/p/build-robust-relationships-carole-robin

    Where to find Carole Robin:

    • LinkedIn: https://www.linkedin.com/in/carole-robin/

    • Email: carolerobinllc@gmail.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) Carole’s background

    (05:17) The importance of building robust relationships

    (10:20) The “Touchy Feely” course at Stanford

    (13:29) An example of the in-class experience

    (17:19) Leaders in Tech: developing interpersonal competence

    (21:36) Progressive disclosure and the 15% rule

    (24:28) Appropriate disclosure

    (26:52) The power of vulnerability

    (34:57) Admitting mistakes and sharing feelings

    (37:08) Understanding mental models

    (42:57) The “three realities” framework

    (53:52) The power of feedback and personal change

    (58:47) The art of inquiry

    (01:03:27) How to get better at giving feedback

    (01:07:47) Exercises and continued learning

    (01:10:49) “Advice hinders relationships”

    (01:16:49) Failure corner: AFOG

    (01:20:30) Takeaways

    (01:21:51) Lessons from long Covid

    Referenced:

    • How to Build Better Relationships: https://www.gsb.stanford.edu/insights/how-build-better-relationships

    Connect: Building Exceptional Relationships with Family, Friends, and Colleagues: https://www.amazon.com/Connect-Building-Exceptional-Relationships-Colleagues-ebook/dp/B0894279WZ

    • Leaders in Tech: https://leadersintech.org/

    • Leaders in Tech Fellows: https://leadersintech.org/learnaboutfellows

    • Steve Jobs: https://www.forbes.com/profile/steve-jobs/

    • Sheryl Sandberg on X: https://twitter.com/sherylsandberg

    • Ursula Burns: https://www.forbes.com/profile/ursula-burns/

    • Application for Leaders in Tech: https://leadersintech.org/programs-and-applications

    • Vygotsky’s Zone of Proximal Development and Scaffolding Theory: https://www.simplypsychology.org/zone-of-proximal-development.html

    • The Best Leaders Aren’t Afraid to Be Vulnerable: https://hbr.org/2022/07/the-best-leaders-arent-afraid-of-being-vulnerable

    • The Surprising Benefits of Admitting Mistakes: 5 Ways to Build Intellectual Humility: https://www.forbes.com/sites/tracybrower/2021/12/29/the-surprising-benefits-of-admitting-mistakes-5-ways-to-build-intellectual-humility/

    • How to Build Conflict Skills—The Pinch/Crunch Model: https://www.forbes.com/sites/hannahart/2023/12/15/how-to-build-conflict-skills-the-pinchcrunch-model/

    • Slides mentioned (The Three Realities Framework | The 15% Rule | Feedback Guidelines): https://pen-name.notion.site/Carole-Robin-4-25-5d47d38a620e4636966d31f4bf3c7d00?pvs=4

    Mindset: The New Psychology of Success: https://www.amazon.com/Mindset-Psychology-Carol-S-Dweck/dp/0345472322

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

    • Long COVID: major findings, mechanisms and recommendations: https://www.nature.com/articles/s41579-022-00846-2

    • Leadership, acceptance, and self-management: my journey with long COVID: https://www.linkedin.com/pulse/leadership-acceptance-self-management-my-journey-long-carole-robin/

    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

    Vision, conviction, and hype: How to build 0 to 1 inside a company | Mihika Kapoor (Product at Figma)

    Vision, conviction, and hype: How to build 0 to 1 inside a company | Mihika Kapoor (Product at Figma)

    Mihika Kapoor is a design-engineer-PM hybrid at Figma, where she was an early PM on FigJam and is now spearheading development on a new product at the company that’s coming out this June. She’s known as the go-to person at Figma for leading new 0-to-1 products, and, as you’ll hear in our conversation, beloved by everyone she works with. Her background includes founding Design Nation, a national nonprofit focused on democratizing design education for undergraduates; spearheading product launches at Meta; and community building within the NYC AI startup scene. In our conversation, we discuss:

    • How to effectively take ideas from 0 to 1 at larger companies

    • How to craft a compelling vision

    • The importance of vulnerability and feedback

    • The role of intuition and product sense in making decisions

    • How to practically communicate your vision

    • How to balance collaboration and strong opinions

    • Advice for building a strong team culture

    • Pivoting with grace and enthusiasm

    • The current AI revolution and its impact on PM

    Brought to you by:

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    Find the transcript at: https://www.lennysnewsletter.com/p/vision-conviction-hype-mihika-kapoor

    Where to find Mihika Kapoor:

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

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

    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) Mihika’s background

    (04:29) Core attributes of great product managers

    (07:34) Crafting a compelling vision

    (12:12) The vision behind FigJam 

    (18:25) Delivering a vision without design or engineering skills

    (21:52) Creating momentum

    (26:36) The importance of strong conviction

    (27:45) Direct communication

    (32:48) Building hype

    (42:20) Immersing yourself in user insights

    (47:16) Operationalizing user insights  

    (50:33) Caring deeply about what you build

    (54:01) Finding passion in your work

    (57:00) Building a strong culture

    (01:07:07) Pivoting with grace and enthusiasm

    (01:11:48) Design Nation

    (01:13:15) Mihika’s weaknesses

    (01:16:07) Building new products at larger companies

    (01:20:50) Coming up with a great idea

    (01:22:49) The key to going from 0 to 1

    (01:26:47) Spreading the idea across the company

    (01:29:15) Closing thoughts

    (01:32:11) Lightning round

    Referenced:

    • Figma: https://www.figma.com/

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

    The Medici Effect: What Elephants and Epidemics Can Teach Us About Innovation: https://www.amazon.com/Medici-Effect-Preface-Discussion-Guide/dp/1633692949

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

    • Cognition: https://www.cognition-labs.com/

    • Devin: https://www.cognition-labs.com/introducing-devin

    • David Hoang on LinkedIn: https://www.linkedin.com/in/dhoang2/

    • Replit: https://replit.com/

    • The Making of Maker Week at Figma: https://www.figma.com/blog/the-making-of-maker-week/

    • Yuhki Yamashita on LinkedIn: https://www.linkedin.com/in/yuhki/

    • Jeff Bezos’ Simple Decision-Making Framework Will Give You Clarity, Conviction, and Courage: https://medium.com/illumination/jeff-bezos-simple-decision-making-framework-will-give-you-clarity-conviction-and-courage-adf8d0183625

    • Alice Ching on LinkedIn: https://www.linkedin.com/in/aliceching/

    • Karl Jiang on LinkedIn: https://www.linkedin.com/in/karl-jiang-4a07424/

    • Kris Rasmussen on LinkedIn: https://www.linkedin.com/in/kristopherrasmussen/

    • Config: https://config.figma.com/

    • Dev Mode: https://www.figma.com/dev-mode/

    • Asana: https://asana.com/

    • Julie Zhuo on LinkedIn: https://www.linkedin.com/in/julie-zhuo/

    • StrengthsFinder test: https://www.gyfted.me/personality-quiz/strengthsfinder-test-free

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

    • Vishal Shah on LinkedIn: https://www.linkedin.com/in/vishalnshah/

    Design Disruptors: https://www.invisionapp.com/films/design-disruptors

    • Daniel Burka on LinkedIn: https://www.linkedin.com/in/dburka/

    • Jamie Myrold on LinkedIn: https://www.linkedin.com/in/jamiemyrold/

    • Design Nation: https://dn.businesstoday.org/

    • Stuart Weitzman on X: https://twitter.com/StuartWeitzman

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

    • Building a long and meaningful career | Nikhyl Singhal (Meta, Google): https://www.lennyspodcast.com/building-a-long-and-meaningful-career-nikhyl-singhal-meta-google/

    • Jambot: https://www.figma.com/community/widget/1274481464484630971/jambot

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

    Harry Potter series: https://www.amazon.com/Harry-Potter-Paperback-Box-Books/dp/0545162076

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

    Creativity, Inc.: Overcoming the Unseen Forces That Stand in the Way of True Inspiration: https://www.amazon.com/Creativity-Inc-Expanded-Overcoming-Inspiration/dp/0593594649

    The Overstory: https://www.amazon.com/Overstory-Novel-Richard-Powers/dp/039335668X

    Severance on AppleTV+: https://tv.apple.com/us/show/severance/umc.cmc.1srk2goyh2q2zdxcx605w8vtx

    Dune on Max: https://www.max.com/movies/dune/e7dc7b3a-a494-4ef1-8107-f4308aa6bbf7

    Dune: Part 2: https://www.dunemovie.com/

    • Arc browser: https://arc.net/

    • Pika: https://pika.art/home

    • The power of recognition: Why you should celebrate your employees | Josh Miller: https://www.lennyspodcast.com/videos/the-power-of-recognition-why-you-should-celebrate-your-employees-josh-miller/

    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 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director)

    Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director)

    Dalton Caldwell is Managing Director and Group Partner at Y Combinator. Prior to YC, he was the co-founder and CEO of imeem (acquired by MySpace in 2009) and the co-founder and CEO of App.net. During his time at YC, he’s advised more than 35 YC unicorns, including DoorDash, Amplitude, Webflow, and Retool, and has worked across 21 different YC batches. He’s also racked up more than 6,500 office hours with founders. In our conversation, we discuss:

    • Why founders need to adopt the mindset “Just don’t die”

    • The most common reason startups fail

    • When to pivot, and characteristics of a good pivot

    • The concept of “tar pit ideas” and examples of bad startup ideas

    • Why investors say no to startups

    • The importance of market size in investment decisions

    • The pitfalls of founders over-delegating

    • Effective ways to talk to customers

    • 20 ideas Dalton is looking to fund

    Brought to you by:

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    Find the transcript at: https://www.lennysnewsletter.com/p/lessons-from-1000-yc-startups

    Where to find Dalton Caldwell:

    • X: https://twitter.com/daltonc

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

    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) Dalton’s background

    (04:41) The value of simple advice

    (07:04) Dalton’s advice: “Just don’t die”

    (08:39) Knowing when to stop

    (11:45) Deciding to pivot

    (14:26) Characteristics of a good pivot

    (17:53) Knowing when to pivot

    (19:03) Zip’s journey and finding a market

    (21:22) Why Dalton says to “Move towards the mountains and the desert”

    (23:45) Tar pit ideas

    (26:49) Understanding why investors say no

    (29:14) The importance of market size

    (32:16) Avoiding over-delegation and hiring senior people too early

    (36:43) Why startups fail

    (40:30) Effectively talking to customers

    (45:17) Examples of startups hustling to talk to customers

    (48:01) Patterns of successful startups

    (52:05) YC’s Request for Startups

    (55:37) Early days of Silicon Valley

    (01:05:33) Contrarian corner: growth hacking for early startups

    (01:09:28) Failure corner

    (01:11:15) Closing thoughts

    (01:12:22) Lightning round

    Referenced:

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

    • Tiger Woods’s website: https://tigerwoods.com/

    • Co-Founder Mistakes That Kill Companies & How to Avoid Them: https://www.youtube.com/watch?v=dlfjs_eEEzs

    • Daniel Alberson’s LinkedIn post about Y Combinator: https://www.linkedin.com/posts/alberson_i-left-my-dream-job-as-a-product-manager-activity-7089677882431533056-jJ9H

    • Companies in Y Combinator W17 Batch: https://www.ycdb.co/batch/w17

    • Brex: https://www.brex.com/

    • Retool: https://retool.com/

    • Segment: https://segment.com/

    • Mixpanel: https://mixpanel.com/

    • Whatnot: https://www.whatnot.com/

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

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

    • Rujul Zaparde on LinkedIn: https://www.linkedin.com/in/rujulz/

    • Zip: https://ziphq.com/

    • Lu Cheng on LinkedIn: https://www.linkedin.com/in/lu-cheng-973b7830/

    • Avoid these tempting startup tar pit ideas: https://www.ycombinator.com/library/Ij-avoid-these-tempting-startup-tarpit-ideas

    • Airbnb acquires Localmind to create crowdsourced advice about neighborhoods: https://skift.com/2012/12/13/airbnb-acquires-localmind-to-create-crowdsourced-advice-about-neighborhoods/

    • Foursquare: https://foursquare.com/

    • Razorpay: https://razorpay.com/

    • Total Addressable Market: https://www.productplan.com/glossary/total-addressable-market/

    • Lenny Bogdonoff on LinkedIn: https://www.linkedin.com/in/rememberlenny/

    • Milk Video: https://milkvideo.com/

    • Lessons from working with 600+ YC startups | Gustaf Alströmer (Y Combinator, Airbnb): https://www.lennyspodcast.com/lessons-from-working-with-600-yc-startups-gustaf-alstromer-y-combinator-airbnb/

    • How the most successful B2B startups came up with their original idea: https://www.lennysnewsletter.com/p/how-the-most-successful-b2b-startups

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

    • Stripe: https://stripe.com/

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

    • John Collison on LinkedIn: https://www.linkedin.com/in/johnbcollison/

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

    • Grant LaFontaine on LinkedIn: https://www.linkedin.com/in/grantlafontaine/

    • Ryan Petersen on LinkedIn: https://www.linkedin.com/in/rpetersen/

    • 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/

    • YC’s latest Request for Startups: https://www.ycombinator.com/blog/ycs-latest-request-for-startups

    • ERPs: https://www.ycombinator.com/rfs#new-enterprise-resource-planning-software

    • Commercial open source companies: https://www.ycombinator.com/rfs#commercial-open-source-companies

    • New space companies: https://www.ycombinator.com/rfs#new-space-companies

    • A way to end cancer: https://www.ycombinator.com/rfs#a-way-to-end-cancer

    • Spatial computing: https://www.ycombinator.com/rfs#spatial-computing

    • New defense technology: https://www.ycombinator.com/rfs#new-defense-technology

    • Bringing manufacturing back to America: https://www.ycombinator.com/rfs#bring-manufacturing-back-to-america

    • Better enterprise glue: https://www.ycombinator.com/rfs#better-enterprise-glue

    • Small fine-tuned models, as an alternative to giant generic ones: https://www.ycombinator.com/rfs#small-finetuned-models-as-an-alternative-to-giant-generic-ones

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

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

    • Sean Parker on LinkedIn: https://www.linkedin.com/in/parkersean/

    • Owen Van Natta on LinkedIn: https://www.linkedin.com/in/owen-van-natta-444a7/

    • Marc Andreessen on X: https://twitter.com/pmarca

    • Picplz 1, Instagram 0 as VC firm Andreessen Horowitz chooses photo app rival: https://www.reuters.com/article/idUS2587232395/

    • Gustaf Alstromer—How to Get Users and Grow: https://www.youtube.com/watch?v=T9ikpoF2GH0

    Getting to Yes: Negotiating Agreement Without Giving In: https://www.amazon.com/Getting-Yes-Negotiating-Agreement-Without/dp/0143118757

    Founding Sales: The Early Stage Go-to-Market Handbook: https://www.amazon.com/Founding-Sales-Go-Market-Handbook-ebook/dp/B08PMK17Z1

    • Founder-led sales | Pete Kazanjy (Founding Sales, Atrium): https://www.lennyspodcast.com/founder-led-sales-pete-kazanjy-founding-sales-atrium/

    The Sopranos on HBO: https://www.hbo.com/the-sopranos

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

    Columbo on Prime Video: https://www.amazon.com/Columbo-Season-1/dp/B008SA89HA

    • Oura ring: https://ouraring.com/

    • Apple watch: https://www.apple.com/watch/

    • SiPhox: https://siphoxhealth.com/

    • Dalton & Michael on YouTube: https://www.youtube.com/playlist?list=PLQ-uHSnFig5Nd98Sc9I-kkc0ZWe8peRMC

    • How Future Billionaires Get Sh*t Done: https://www.youtube.com/watch?v=ephzgxgOjR0

    • The Student’s Guide to Becoming a Successful Startup Founder: https://www.youtube.com/watch?v=O5KCB2p6SB8

    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 GitLab way: Kindness, transparency, and short toes | David DeSanto (CPO)

    The GitLab way: Kindness, transparency, and short toes | David DeSanto (CPO)

    David DeSanto is the chief product officer of GitLab, which is the largest remote-only company in the world. They share many of their team meetings on YouTube, and they’ve grown from being an open-source code management product competing with GitHub to a multi-product platform that covers security, compliance, continuous integration, project management, and deployment tools, many of which are infused with AI magic. In our conversation, we discuss:

    • How GitLab operationalizes transparency

    • The philosophy behind recording and sharing team meetings on YouTube

    • Their extensive public employee handbook

    • GitLab’s core value of having “short toes”

    • Challenges and advice for doing remote work well

    • Strategies for ensuring effective communication in a remote work environment

    • GitLab’s breadth-over-depth strategy

    • The company’s unique approach to AI

    • The value of using humor in high-stakes conversations

    Brought to you by:

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    Find the transcript at: https://www.lennysnewsletter.com/p/the-gitlab-way

    Where to find David DeSanto:

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

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

    • Threads: https://www.threads.net/@david.the.beard

    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) David’s background

    (04:20) Maintaining an epic beard

    (05:29) Why GitLab publicly shares team meetings

    (09:49) The GitLab Handbook

    (11:30) GitLab’s issue tracker

    (14:29) How to successfully build a culture of transparency

    (18:11) Benefits of operating with transparency

    (19:55) The value of building in public

    (21:53) How GitLab implements their core value of kindness

    (25:16) What it means to have “short toes”

    (27:41) Other core values

    (32:16) Common reasons for not fitting in at GitLab

    (34:42) Advice for remote teams

    (42:04) Advice for getting into product

    (43:52) Advice for PMs who are struggling in a remote world

    (48:25) Specific tools that help with remote work

    (53:13) Time zones and remote work

    (57:18) Breadth-over-depth strategy

    (01:04:14) AI at GitLab

    (01:13:11) GitLab’s products and solutions

    (01:14:54) Lightning round

    Referenced:

    • GitLab: https://about.gitlab.com/

    • UX Showcase—David DeSanto introduction to UX team and AMA: https://www.youtube.com/watch?v=fEdsmnVKNj4

    • The GitLab Handbook: https://handbook.gitlab.com/

    • Sid Sijbrandij on LinkedIn: https://www.linkedin.com/in/sijbrandij/

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

    • GitLab issues: https://docs.gitlab.com/ee/user/project/issues/

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

    • GitLab values: https://handbook.gitlab.com/handbook/values

    • GitLab organizational structure: https://handbook.gitlab.com/handbook/company/structure

    • GitLab direction: https://about.gitlab.com/direction/

    • Dogfooding: A simple practice to help you build better products: https://medium.com/agileinsider/dogfooding-a-simple-practice-to-help-you-build-better-products-b5954af4d5f7

    • The ultimate guide to adding a PLG motion | Hila Qu (Reforge, GitLab): https://www.lennysnewsletter.com/p/the-ultimate-guide-to-adding-a-plg

    • 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

    • HubSpot: https://www.hubspot.com/

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

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

    • Open-core model: https://en.wikipedia.org/wiki/Open-core_model

    • GitLab Duo: https://about.gitlab.com/gitlab-duo/

    • GitLab Docs: https://docs.gitlab.com/

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

    • GitLab Acquires UnReview to Expand Its DevOps Platform with Machine Learning Capabilities: https://about.gitlab.com/press/releases/2021-06-02-gitlab-acquires-unreview-machine-learning-capabilities/

    Essentialism: The Disciplined Pursuit of Less: https://www.amazon.com/Essentialism-Disciplined-Pursuit-Greg-McKeown/dp/0804137382

    • The Mission Critical Core/Context Model for Product Managers: https://secretpmhandbook.com/the-mission-critical-corecontext-model-for-product-managers/

    The Devil’s Hour on AppleTV+: https://tv.apple.com/us/show/the-devils-hour/umc.cmc.3zw4tyzd4lvor5mwhujms63x3

    Glass Onion: A Knives Out Mystery on Netflix: https://www.netflix.com/title/81458416

    • Taylor Swift’s The Eras Tour on Prime Video: https://www.amazon.com/TAYLOR-SWIFT-ERAS-EXTENDED-VERSION/dp/B0CP99SN2B

    • The STAR method: https://capd.mit.edu/resources/the-star-method-for-behavioral-interviews/

    • Artifact News: https://artifact.news/

    • Superhuman: https://superhuman.com/

    • Arc browser: https://arc.net/

    • An inside look at how The Browser Company builds product: https://www.lennysnewsletter.com/p/competing-with-giants-an-inside-look

    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