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    Podcast Summary

    • Challenging the Default Path to Create a Fulfilling LifeBy being aware of societal expectations and consciously choosing our own priorities, we can create a more balanced life that aligns with our true values.

      The default path is deeply ingrained in our society and often goes unquestioned. It is the predetermined script we feel compelled to follow, such as going to college, getting a good job, and following a set timeline for success. Stepping off this path can be challenging because it triggers insecurities in others who are still on it. However, being conscious of the default path and its implicit contracts is essential. It's not necessary to completely abandon the default path, but rather to be aware of the trade-offs and consciously choose our own priorities. By remixing our path and constantly reevaluating our goals and desires, we can create a more fulfilling and balanced life that aligns with our true values.

    • Embracing Uncertainty and Abundance in Work LifeThe pathless path encourages us to embrace uncertainty, experiment, and actively search for work that brings us fulfillment, making our career journey an endless discovery.

      The concept of the pathless path is about shifting away from the default and embracing discomfort and uncertainty in our work lives. It encourages us to navigate through a sense of abundance and have faith that things will be okay, even though we might not know what comes next. This approach is applicable to various situations, from those who are pursuing a creative path or freelancing to individuals seeking a reinjection of aliveness in their careers. The key is to develop a relationship with uncertainty and experiment more, while embracing the shared ethic of possibility, opportunity, and optimism. Ultimately, the goal is not just to find a job or make money, but to actively and consciously search for the work we want to keep doing, making it an endless journey of discovery.

    • Designing a Life Around Enjoyable WorkPrioritizing our own happiness and fulfillment can lead to finding meaningful work without sacrificing everything. Finding ways to do what we love and being protective of that can create space for new possibilities.

      Work doesn't have to be something we dread or tolerate. Paul Miller's experience shows that it's possible to design a life around work that we actually enjoy. Instead of viewing work as a necessary trade-off of our time, we can find ways to do what we love and be protective of that. Taking a 3-month sabbatical or even just an afternoon to reconnect with ourselves and explore new possibilities can be incredibly valuable. We often make excuses about why we can't prioritize our own happiness and fulfillment, but if we truly make it a main priority, we can find ways to create the space and opportunity for meaningful work without risking everything.

    • The Benefits of Taking a SabbaticalTaking a break from work can help individuals reconnect with themselves, gain deeper understanding of their motivations, and lead to unexpected opportunities and personal growth. Employers should prioritize the well-being and fulfillment of their workforce.

      Taking a sabbatical or extended time off from work can have profound benefits. It allows individuals to reconnect with themselves and explore what truly brings them alive. By creating space and delving into their relationship with work, people can gain a deeper understanding of their motivations and aspirations beyond just financial reasons. This process often leads to unexpected opportunities and personal growth. While some may fear that offering sabbaticals may result in employees leaving, it is essential for employers to interrogate their own insecurities around work and consider the well-being and fulfillment of their workforce. Ultimately, taking time off to unwind and explore can lead to greater clarity, creativity, and overall career satisfaction.

    • Exploring new paths and finding fulfillment through remote work.Remote work offers the freedom to pursue personal aspirations and the opportunity to discover new paths towards joy, fulfillment, and even higher income and long-term success.

      Remote work has opened up opportunities for people to become the person they want to be. Many individuals leave companies because they don't see a path to fulfill their personal aspirations. To discover a potential new path, it is important to get creative and explore different activities that bring joy and fulfillment. Engaging in exercises like reaching out to experts or individuals ahead on a similar path can provide valuable insights and guidance. These conversations can lead to various possibilities, such as starting a new business, shifting careers, or even reinventing oneself. The advancements in tools and technology, like ChatGpt, further enable flexible work and make it easier to pursue alternative paths. Contrary to common belief, following one's passion often leads to higher income and long-term success.

    • Embracing Exploration and Self-Discovery for a Fulfilling LifeLowering living costs and prioritizing self-discovery can lead to a more fulfilling life, and taking a leap in pursuing passions can be a valuable gift from one's past self.

      Optimizing for exploration and self-discovery can lead to a more fulfilling and delightful life. Paul Miller chose to lower his cost of living and prioritize getting to know himself again, which initially resulted in lower income. However, he eventually found a path that allowed him to make more money while still enjoying every day with his family. To create space for exploration, there are various options like moving abroad, selling possessions, applying for grants or loans, and turning a current job into a contract job for more flexibility. Additionally, setting a budget or creating agreements for how much money to invest in personal growth can help shift perspectives and overcome societal judgment. Ultimately, taking a leap in pursuing one's passions and finding fulfillment can be a valuable gift from one's past self.

    • Embracing Change: A pathway to unexpected growth and creativityTaking risks, stepping out of comfort zones, and embracing change can lead to growth and creativity. Fear of failure often holds us back, but most regrets come from not taking action. Taking breaks and exploring new interests can enhance the creative process. Gradually finding a new path is more effective than an all-or-nothing leap.

      Taking risks and embracing change can lead to unexpected creativity and growth. When people step out of their comfort zones and bet on themselves, they often tap into their ingenuity and resourcefulness. Fear of failure often holds us back, but in reality, most regrets come from not taking action rather than from making mistakes. It's important to remember that creativity can't be forced and that taking breaks or engaging in unrelated activities can actually enhance the creative process. Additionally, finding a new path doesn't have to be an all-or-nothing leap. It's often a gradual process of exploring new interests, experimenting with different projects, and eliminating risks along the way.

    • Discovering Your Energy Sources and Overcoming Fears for Personal GrowthPay attention to activities that energize or drain you, and use this self-awareness to make informed decisions. Overcoming insecurities and reframing the cost of inaction can lead to unexpected paths and personal growth.

      It is crucial to pay close attention to what gives you energy and what saps your energy. By analyzing how different activities make you feel, you can determine what truly energizes you and what drains you. This self-awareness allows you to make informed decisions about how to spend your time and pursue your goals. It may lead you to unexpected paths, as seen in Lenny's case, where he discovered his love for writing instead of consulting or starting a company. Overcoming fears is also an essential part of the process. Reframing the cost of inaction can help you overcome insecurities and take necessary steps towards personal growth and success.

    • Embracing Fears and Embracing New Experiences on Your Path to PassionAcknowledge and accept fears, embrace new experiences, and learn from each one to discover your true passion and avoid creating unfulfilling jobs for yourself.

      Fears and worries are inevitable along the path of pursuing your passion. Whether it's financial concerns or existential anxieties, these fears don't simply disappear. The key is to acknowledge and accept them rather than trying to ignore or solve them through conventional means like getting a job. Dancing with your fears and accepting that they will be a part of your life is crucial. Additionally, it's important to be comfortable with trying new things and being open to failure. Finding the right path often involves experimentation and learning from each experience. By shipping, quitting, and learning, you can discover what truly energizes you and avoid creating jobs for yourself that you don't enjoy.

    • Focus on what brings fulfillment and leverage time effectively to enhance productivity and satisfaction.Pay attention to activities that give you energy and enjoyment, create systems for flexible and asynchronous work, and periodically reassess and reinvent yourself for continued growth and avoid getting stuck in maintenance mode.

      It's crucial to pay attention to what gives you energy and what you genuinely enjoy. Creating jobs or tasks for yourself that you dislike or have no passion for can be draining and counterproductive. Lenny and Paul highlight the importance of focusing on activities that bring you fulfillment and leveraging your time effectively. Building a life with flexibility and creating systems that allow for asynchronous work can enhance productivity and satisfaction. However, it's essential to periodically reassess and reinvent yourself to avoid getting stuck in maintenance mode. This commitment to constant reinvention requires a willingness to reflect, eliminate unnecessary tasks, and delegate or outsource responsibilities.

    • Embracing the Gig Economy: The Future of WorkEmbrace unconventional work arrangements and explore new paths for a more fulfilling career, despite the challenges and uncertainties that may come along the way. Seek resources and insights from others on similar journeys.

      The future of work is becoming increasingly gigafied and unconventional. The growth in alternative work arrangements and the gig economy is reshaping how companies operate and how people find employment. This means that the traditional path of full-time employment may not be the only option anymore. It's important to realize that taking the pathless path might be difficult and uncertain, but it can also be worth it. Exploring unconventional paths and finding something more fulfilling requires a mindset shift and the willingness to try new things. Seeking out resources like books, podcasts, and conversations with people on interesting paths can provide valuable insights and inspiration for those considering this journey.

    • Prioritizing Fulfillment and Passion over External SuccessTrue satisfaction and fulfillment in life come from being connected to our purpose and finding intrinsic enjoyment and connection in what we do, rather than chasing achievements and external markers of success.

      Chasing external success and extrinsic outcomes may not bring true satisfaction and fulfillment in life. Paul Miller emphasizes the importance of coming alive and being connected to what one is doing. He believes that personal energy and intrinsic motivation are more valuable than achievements and prestige. This mindset guided his decision to reject a book deal that didn't align with his sense of purpose and authenticity. Additionally, when it comes to podcasting, Paul advises against pursuing it solely for monetary gain. Instead, he suggests finding intrinsic enjoyment and connection in the conversations and format of the podcast. Ultimately, the key lesson is to prioritize personal fulfillment and passion over external markers of success.

    • Embrace the potential and push the boundaries of podcasts and newslettersTake action, share your passion, and deliver valuable content to make a difference in the world of podcasts and newsletters.

      The world of podcasts and newsletters offers great opportunities for creativity and connection. Despite concerns about there being too many podcasts and newsletters, there is always room for improvement and adding value. By delivering more useful, valuable, and interesting content, you can capture people's attention and make a difference. The creative act of podcasting or producing a newsletter can be meaningful in itself, regardless of financial gain. Just start and do it for yourself, and you may find that others also find it interesting and valuable. Remember that the best ideas often come from simply taking action and sharing your passion. So, embrace the potential of podcasts and newsletters, and keep pushing the boundaries of what is possible.

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

    Lessons from a two-time unicorn builder, 50-time startup advisor, and 20-time company board member | Uri Levine (co-founder of Waze)

    Lessons from a two-time unicorn builder, 50-time startup advisor, and 20-time company board member | Uri Levine (co-founder of Waze)

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

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

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

    • Why firing is more important than hiring

    • How Waze iterated to achieve product-market fit

    • Tactics for telling a compelling story when fundraising

    • Much more

    Brought to you by:

    Vanta—Automate compliance. Simplify security

    Mercury—The powerful and intuitive way for ambitious companies to bank

    LinkedIn Ads—Reach professionals and drive results for your business

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

    Where to find Uri Levine:

    • X: https://twitter.com/urilevine1

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

    • Website: https://urilevine.com/

    Where to find Lenny:

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

    • X: https://twitter.com/lennysan

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

    In this episode, we cover:

    (00:00) Uri’s background

    (02:50) Falling in love with the problem

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

    (10:54) The importance of passion

    (12:06) A pivot example

    (14:01) Where to find startup ideas

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

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

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

    (39:53) Fundraising tips

    (48:02) How to make your presentations stronger

    (50:32) A wild fundraising story

    (53:46) Firing and hiring

    (59:50) The 30-day test

    (01:04:12) Understanding users

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

    (01:15:36) Lightning round

    Referenced:

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

    • Waze: https://www.waze.com/

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

    • Pontera: https://pontera.com/

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

    Lenny may be an investor in the companies discussed.



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

    Inside Canva: Coaches not managers, giving away your Legos, and running profitably | Cameron Adams (co-founder and CPO)

    Inside Canva: Coaches not managers, giving away your Legos, and running profitably | Cameron Adams (co-founder and CPO)

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

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

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

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

    • Insights into Canva’s SEO growth strategy

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

    • Stories from the early days

    Brought to you by:

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

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

    Vanta—Automate compliance. Simplify security.

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

    Where to find Cameron Adams:

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

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

    • Website: https://themaninblue.com/

    Where to find Lenny:

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

    • X: https://twitter.com/lennysan

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

    In this episode, we cover:

    (00:00) Cameron’s background

    (02:00) Reflecting on the success of Canva

    (04:50) Reflecting on hard times

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

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

    (13:56) What makes Canva unique

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

    (21:44) Why Canva has no managers

    (24:29) Product management at Canva

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

    (30:37) Why they spent a year building their MVP before launch

    (33:49) Advice for building an MVP

    (41:23) Canva’s onboarding transformation

    (44:25) Canva’s SEO strategy

    (50:37) The success of Canva’s freemium strategy

    (54:24) Integrating AI into Canva’s product

    (01:01:50) Where to find Cameron

    Referenced:

    • Canva: https://www.canva.com/

    • Melanie Perkins on LinkedIn: https://www.linkedin.com/in/melanieperkins

    • Cliff Obrecht on LinkedIn: https://www.linkedin.com/in/cliff-obrecht-79ba9920

    • Jennie Rogerson, Head of People, LinkedIn post about “season opener” events: https://www.linkedin.com/posts/jennierogerson_season-opener-is-one-of-my-favourite-events-activity-7006815614556135424-73bD/

    Game of Thrones on HBO: https://www.hbo.com/game-of-thrones

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

    • ‘Give Away Your Legos’ and Other Commandments for Scaling Startups: https://review.firstround.com/give-away-your-legos-and-other-commandments-for-scaling-startups/

    • Minimum viable product (MVP): https://www.productboard.com/glossary/minimum-viable-product-mvp

    • Canva’s SEO Strategy Is Elite: https://thegrowthplaybook.substack.com/p/canvas-seo-strategy-is-elite

    • The SEO Strategy That Led Canva to a $40 Billion Valuation: https://www.youtube.com/watch?v=INyGKt6LAqM

    • Andrianes Pinantoan on LinkedIn: https://www.linkedin.com/in/andrianes/

    • Canva Create: https://www.canva.com/canva-create/

    Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email 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 surprising truth about what closes deals: Insights from 2.5m sales conversations | Matt Dixon (author of The Challenger Sale and The JOLT Effect)

    The surprising truth about what closes deals: Insights from 2.5m sales conversations | Matt Dixon (author of The Challenger Sale and The JOLT Effect)

    Matt Dixon is one of the world’s foremost experts in sales and the author of The Challenger Sale, which sold over a million copies worldwide and was a #1 Amazon and Wall Street Journal bestseller. His most recent book, The JOLT Effect, focuses on overcoming customer indecision—one of the biggest challenges to closing deals. Outside of writing, Matt co-founded DCM Insights, a boutique consultancy helping organizations understand customer behavior, and is a frequent contributor to the Harvard Business Review, with more than 20 print and online articles to his credit. In our conversation, we discuss:

    • Why 40% to 60% of qualified sales opportunities are lost due to customer indecision

    • Why dialing up FOMO doesn’t work, and what to do instead

    • The “pings and echoes” technique to catch issues early

    • The JOLT method for overcoming indecision

    • Key lessons from The Challenger Sale

    • Practical examples of how to apply these principles to close more deals

    Brought to you by:

    Enterpret—Transform customer feedback into product growth

    Webflow—The web experience platform

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

    Find the transcript at: https://www.lennysnewsletter.com/p/close-more-deals-matt-dixon

    Where to find Matt Dixon:

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

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

    Where to find Lenny:

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

    • X: https://twitter.com/lennysan

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

    In this episode, we cover:

    (00:00) Matt’s background

    (01:57) The research behind Matt’s books

    (06:08) Insights from The JOLT Effect

    (10:15) FOMO vs. FOMU

    (18:18) An example of selling software

    (26:04) The JOLT method Step 1: Judge their level of indecision

    (29:41) The “pings and echoes” technique

    (34:49) Step 2: Offer a recommendation

    (38:36) Step 3: Limit the exploration

    (41:43) Step 4: Take risk off the table

    (45:58) When to hit the pause button with a customer

    (47:27) Insights from The Challenger Sale

    (49:07) An example of a challenger sale

    (55:23) Where to find Matt

    Referenced:

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

    The Challenger Sale: Taking Control of the Customer Conversation: https://www.amazon.com/Challenger-Sale-Control-Customer-Conversation/dp/0670922854

    The JOLT Effect: How High Performers Overcome Customer Indecision: https://www.amazon.com/JOLT-Effect-Performers-Overcome-Indecision/dp/0593538102

    • Gartner acquires CEB: https://www.gartner.com/en/about/acquisitions/history/ceb-acquisition

    Tiger King on Netflix: https://www.netflix.com/title/81115994

    • Why sourdough went viral: https://www.economist.com/1843/2020/08/04/why-sourdough-went-viral

    • Neil Rackham: https://en.wikipedia.org/wiki/Neil_Rackham

    • Status quo bias in decision-making: https://en.wikipedia.org/wiki/Status_quo_bias

    • Omission bias: https://thedecisionlab.com/biases/omission-bias

    • Gartner Magic Quadrant & Critical Capabilities: https://www.gartner.com/en/research/magic-quadrant

    • Dunning-Kruger effect: https://en.wikipedia.org/wiki/Dunning%E2%80%93Kruger_effect

    • Stop Losing Sales to Customer Indecision: https://hbr.org/2022/06/stop-losing-sales-to-customer-indecision

    • Dentsply Sirona: https://www.dentsplysirona.com/

    • “We happy?” Briefcase scene from Tarantino’s Pulp Fiction: https://www.youtube.com/watch?v=FGchDuOpbhE

    • Nupro Freedom Cordless Prophy System: https://www.dentsplysirona.com/en-us/discover/discover-by-category/preventive/hygiene-handpieces.html

    Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email 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 frameworks for growing your product, career, and impact | Bangaly Kaba (YouTube, Instagram, Facebook, Instacart)

    Unorthodox frameworks for growing your product, career, and impact | Bangaly Kaba (YouTube, Instagram, Facebook, Instacart)

    Bangaly Kaba was an early growth PM at Facebook, head of growth at Instagram, and VP of Product at Instacart and is currently Director of Product at YouTube overseeing a global team working on creator monetization. Bangaly has also been a growth advisor to dozens of companies, including Twitter, on the board of multiple companies, and is an active angel investor. In our conversation, we discuss:

    • A simple framework for choosing where to work and what to work on

    • The importance of “understand work”

    • The “adjacent users” theory and how it can help you drive growth

    • Advice for coaching product managers

    • Invaluable lessons from his time at Instagram, Facebook, and YouTube

    • Much more

    Brought to you by:

    Uizard—AI-powered prototyping for visionary product leaders

    Mercury—The powerful and intuitive way for ambitious companies to bank

    Vanta—Automate compliance. Simplify security.

    Find the transcript and references at: https://www.lennysnewsletter.com/p/frameworks-for-growing-your-career-bangaly-kaba

    Where to find Bangaly Kaba:

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

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

    • Instagram: https://www.instagram.com/iambangaly/

    Where to find Lenny:

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

    • X: https://twitter.com/lennysan

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

    In this episode, we cover:

    (00:00) Bangaly’s background

    (06:31) Choosing where to work and what to work on

    (08:39) The impact factor

    (10:53) Evaluating the environment

    (15:53) The manager component

    (18:27) The skills part of the equation

    (23:49) Advice on finding a mentor

    (25:42) The power of “understand work”

    (31:17) Operationalizing understand work

    (37:55) Balancing understand work

    (41:25) Managing complex change

    (45:26) Effective management of product managers

    (51:35) The role of product managers as coaches and team leaders

    (54:52) Driving growth through flywheels and value proposition

    (01:03:14) Understanding adjacent users

    (01:08:41) The role of partnerships and SEO in Instagram’s early growth

    (01:16:08) The secret behind Instagram’s growth

    (01:25:37) Lessons from Facebook

    (01:29:15) Failure corner

    (01:31:58) Lightning round

    Referenced:

    • Impact = Environment x Skills: How to Make Career Decisions: https://www.reforge.com/blog/how-to-make-career-decisions

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

    • Casey Winters’s blog: https://caseyaccidental.com/

    • Ben Thompson’s newsletter: https://stratechery.com/about/

    • Elena Verna on how B2B growth is changing, product-led growth, product-led sales, why you should go freemium not trial, what features to make free, and much more: https://www.lennysnewsletter.com/p/elena-verna-on-why-every-company

    • George Lee on LinkedIn: https://www.linkedin.com/in/geolee/

    • Bangaly Kaba: The Path to 1 Billion: Lessons Learned from Growing Instagram—CXL LIVE 2018: https://www.youtube.com/watch?v=L9ZHlb6kj_E

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

    • Bloom’s taxonomy: https://en.wikipedia.org/wiki/Bloom%27s_taxonomy

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

    • Mike Krieger on LinkedIn: https://www.linkedin.com/in/mikekrieger/

    • LeBron James: https://en.wikipedia.org/wiki/LeBron_James

    • Kobe Bryant: https://en.wikipedia.org/wiki/Kobe_Bryant

    •  Mike Krzyzewski: https://en.wikipedia.org/wiki/Mike_Krzyzewski

    • John Calipari: https://en.wikipedia.org/wiki/John_Calipari

    • Stripe: https://stripe.com/

    • Chief: https://chief.com/

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

    • The Adjacent User: https://brianbalfour.com/quick-takes/the-adjacent-user

    • How the biggest consumer apps got their first 1,000 users: https://www.lennysnewsletter.com/p/how-the-biggest-consumer-apps-got

    • Alex Zhu on LinkedIn: https://www.linkedin.com/in/keepsilence/

    • From Brush to Canvas with Alex Zhu of Musical.ly: https://www.youtube.com/watch?v=ey15v81pwII

    • Selena Gomez on Instagram: https://www.instagram.com/selenagomez/

    • Kim Kardashian on Instagram: https://www.instagram.com/kimkardashian/

    • Rob Andrews on LinkedIn: https://www.linkedin.com/in/robby-andrews-64669720/

    • Instagram’s growth speeds up as it hits 700 million users: https://techcrunch.com/2017/04/26/instagram-700-million-users/

    Range: Why Generalists Triumph in a Specialized World: https://www.amazon.com/Range-Generalists-Triumph-Specialized-World/dp/0735214484

    Deep Work: Rules for Focused Success in a Distracted World: https://www.amazon.com/Deep-Work-Focused-Success-Distracted/dp/1455586692

    Start at the End: How to Build Products That Create Change: https://www.amazon.com/Start-End-Products-Create-Change/dp/0525534423

    • Flighty app: https://www.flightyapp.com/

    • Adam Grant on Instagram: https://www.instagram.com/adamgrant/

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

    Lenny may be an investor in the companies discussed.



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

    Why not asking for what you want is holding you back | Kenneth Berger (exec coach, first PM at Slack)

    Why not asking for what you want is holding you back | Kenneth Berger (exec coach, first PM at Slack)

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

    • Why asking for what you want is so impactful

    • Three steps to effectively ask for what you want

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

    • Why hearing “no” is a normal part of the process

    • The “dream behind the complaint” technique for uncovering desires

    • Kenneth’s experience of being fired three times from Slack

    • How embracing fear and discomfort is key to getting what you want

    • Why discipline is overrated

    Brought to you by:

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    Find the transcript at: https://www.lennysnewsletter.com/p/ask-for-what-you-want-kenneth-berger

    Where to find Kenneth Berger:

    • X: https://twitter.com/kberger

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

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

    • Website: https://kberger.com/

    Where to find Lenny:

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

    • X: https://twitter.com/lennysan

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

    In this episode, we cover:

    (00:00) Kenneth’s background

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

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

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

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

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

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

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

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

    (24:07) Doing an integrity check

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

    (30:45) Understanding your influence

    (34:48) Using complaints as inspiration

    (36:24) Internal family systems

    (38:00) Giving feedback

    (41:24) Step 3: Accept the response

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

    (57:30) Advice on being the first PM at a company or startup

    (01:04:58) Contrarian corner: anti-discipline

    (01:05:52) Lightning round

    Referenced:

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

    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

    • The importance of strategic clarity

    • The role of category design in creating successful products

    • Why companies should strive to be “fundamentally different,” not “incrementally better”

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

    Brought to you by:

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    Find the transcript at: https://www.lennysnewsletter.com/p/be-fundamentally-different-jag-duggal

    Where to find Jag Duggal:

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

    Where to find Lenny:

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

    • X: https://twitter.com/lennysan

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

    In this episode, we cover:

    (00:00) Jag’s background

    (04:34) Nubank’s remarkable achievements

    (06:01) Nubank’s product development process

    (11:23) Nubank’s values

    (12:16) Building products people love fanatically

    (15:21) The Sean Ellis score

    (21:27) An example project using the Sean Ellis score

    (25:07) Picking up the phone and calling customers

    (28:20) The importance of starting small and iterating

    (30:42) Pushing back effectively

    (34:10) Uncovering pain points through customer research

    (37:53) An example of setting a clear hypothesis

    (42:01) Developing a strategy

    (52:16) “Be fundamentally different, not incrementally better”

    (53:10) Category design

    (57:37) Nubank’s founding story and goals for the future

    (01:00:46) Advice for adding new product lines

    (01:03:46) The future of fintech and banking

    (01:09:23) AI corner

    (01:12:34) Failure corner

    (01:20:24) Key takeaways

    (01:22:11) Lightning round

    Referenced:

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

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

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

    • SoFi: https://www.sofi.com/

    • Affirm: https://www.affirm.com/

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

    • Citi: https://www.citi.com/

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

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

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

    • Susan Wojcicki on LinkedIn: https://www.linkedin.com/in/susan-wojcicki-b136a99/

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

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

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

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

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

    • Lomi: https://lomi.com/

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

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

    Uizard—AI-powered prototyping for visionary product leaders

    Webflow—The web experience platform

    Coda—The all-in-one collaborative workspace

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

    Where to find Vikrama Dhiman:

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

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

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

    Where to find Lenny:

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

    • X: https://twitter.com/lennysan

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

    In this episode, we cover:

    (00:00) Vikrama’s background

    (03:56) Three common traits among great PMs

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

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

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

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

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

    (23:26) The art of the pushback

    (26:55) Common factors that impede career growth

    (33:39) Vikrama’s personal reflections

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

    (46:28) The ambiguity of the PM role

    (51:47) The 8 axis for PM growth

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

    (59:30) Lightning round

    Referenced:

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

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

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

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

    • Oracle: https://www.oracle.com/

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

    Brought to you by:

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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.



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    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

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