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    How to speak more confidently and persuasively | Matt Abrahams (professor, podcast host, author, speaker)

    Effective communication involves authentic interest, self-expression, and giving constructive feedback to build genuine connections

    enMarch 31, 2024

    About this Episode

    Matt Abrahams is a renowned communication expert, with decades of teaching, coaching, and consulting experience. At Stanford University, he teaches a business school class on strategic communication. Beyond academia, he’s a sought-after keynote speaker and consultant, guiding presenters from IPO road shows to prestigious platforms like TED, the World Economic Forum, and the United Nations. His acclaimed podcast, Think Fast, Talk Smart, garners millions of listeners, and his book, Think Faster, Talk Smarter, equips speakers with practical skills for impromptu success. With a previous bestseller, Speaking Up Without Freaking Out, Matt has empowered countless individuals to speak confidently and authentically. In our conversation, we discuss:

    • The concept of “daring to be dull”

    • The power of visualization to desensitize oneself to speaking situations

    • Managing negative self-talk

    • The WHAT structure for delivering toasts (why we are here, how you are connected, anecdote, thanks)

    • The ADD structure for Q&As (answer, detailed example, describe relevance)

    • Breathing techniques to reduce anxiety, such as the double exhale

    • Concrete speaking structures like What? So What? Now What? and the Four I’s (information, impact, invitation, implications)

    • Much more

    Brought to you by:

    Sprig—Build a product people love

    Dovetail—Bring your customer into every decision

    Coda—Meet the evolution of docs

    Find the transcript and references at: https://www.lennysnewsletter.com/p/how-to-speak-more-confidently-and

    Where to find Matt Abrahams:

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

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

    • Website: https://mattabrahams.com/

    • Podcast: https://open.spotify.com/show/6ll0MwobDt1JW9gYaOONEo

    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

    (04:50) Techniques for managing anxiety in public speaking

    (10:57) Dare to be dull

    (13:40) Reframing anxiety as excitement

    (16:08) Using mantras to boost confidence

    (18:45) Managing negative self-talk

    (20:03) Normalizing speaking anxiety

    (23:12) Using conversation as a communication technique

    (24:52) Using the double-exhale breathing technique

    (28:29) Getting present-oriented

    (29:46) Using tongue twisters

    (33:34) Broad advice for speaking on the spot

    (38:35) The PREP structure

    (38:59) The What? So What? Now What? structure

    (42:10) Toastmasters and improv

    (45:31) Getting better at small talk

    (51:05) The importance of sharing back

    (52:33) Giving feedback

    (56:31) Improving toasts and tributes

    (01:02:57) Mastering Q&A sessions

    (01:07:25) Apologizing effectively

    (01:09:29) Closing thoughts

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

    Lenny may be an investor in the companies discussed.



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

    🔑 Key Takeaways

    • Visualize and prepare for presentations to reduce anxiety, focus on connection rather than perfection, and practice communication skills for career growth
    • Visualization techniques, such as mental imagery and deep breathing, can help manage anxiety and improve spontaneity in public speaking. Instead of focusing on negative thoughts, imagine yourself in the speaking environment interacting positively with the audience.
    • Visualization and calming techniques can help reduce anxiety and improve performance during public speaking engagements. Focus on getting the task done rather than striving for perfection to reduce cognitive load and connect better with the audience.
    • Changing how we perceive anxiety during speaking engagements can improve performance by labeling symptoms as signs of excitement, boosting confidence and focusing on positive aspects.
    • Creating a personal mantra can help combat self-deprecating thoughts, boost confidence, and focus on value brought to the table. Personifying inner critic and seeking help can also improve communication skills and build confidence.
    • Sharing experiences and applying techniques like reframing, asking questions, and distracting the audience can help manage anxiety and improve communication skills.
    • Deep belly breathing and focusing on the present moment can help reduce anxiety and improve performance. Most anxiety occurs before speaking, and managing that initial minute can make a big difference. Our body's feelings influence our mind's thoughts, so managing our physical state can have a profound impact on our overall well-being.
    • The 4-7-8 breathing technique and tongue twisters are effective methods to help manage anxiety by staying present. Tongue twisters also warm up the voice for better communication.
    • Preparation and practice are key to effective spontaneous speaking. Use a simple framework to structure your thoughts and provide clear, concise messages that resonate with your audience.
    • Use problem-solution-benefit or what-so-what-now-what structures to make communication clear, logical, and memorable. Problem-solution-benefit presents a problem, solution, and benefit, while what-so-what-now-what asks what, so what, and now what to establish context, explain significance, and outline next steps.
    • Regularly practice, reflect, and seek feedback to improve communication skills. Join organizations, take classes, and apply learnings for growth.
    • Balance disclosure, be interested, match levels, encourage sharing, and shift responses for successful conversations.
    • Effective communication involves authentic interest, self-expression, and giving constructive feedback to build genuine connections
    • When giving feedback, level-set the topic, share impact, make an invitation, and discuss implications for productive collaboration.
    • Use the acronym WHAT (Why, Connection, Anecdote, Gratitude) to structure a successful toast or tribute. Keep it brief, emotional, and authentic.
    • Use genuine emotion, anecdotes, and stories in public speaking. During Q&A sessions, view questions as opportunities for learning and expansion.
    • Answer questions using ADD structure: Answer, Detailed example, Description. Apologize effectively using AAA structure: Acknowledge, Appreciate, Amends. These structures ensure clear and complete communication.
    • Improve communication skills by taking the first step, showing empathy, and dedicating time to practice. Learn from experts like Matt Abrahams through his resources and connections.

    📝 Podcast Summary

    Improve public speaking through visualization, preparation, and connection

    Effective communication, especially in public speaking, can be improved through various techniques. Visualization and preparation are crucial for reducing anxiety and performing well on the spot. Additionally, focusing on connection rather than perfection can help calm nerves and allocate resources for success. Matt Abrahams, a professor at Stanford University and host of the Think Fast, Talk Smart podcast, emphasizes the importance of communication skills in various aspects of our careers. To improve, consider practicing these techniques and consider attending events like Dovetail's Insight Out conference for valuable insights. Remember, becoming a better communicator can be a game changer in your professional growth.

    Visualization for Confidence-Building and Desensitization

    Effective public speaking, whether prepared or on the spot, can be enhanced through various techniques to manage anxiety and improve spontaneity. Visualization is a powerful tool for desensitization and confidence-building. Instead of visualizing the audience naked, imagine yourself in the speaking environment, interacting with the audience. This technique, based on research from the University of Oregon, allows for greater control over the speaking event and can be practiced through deep breathing and mental imagery. Additionally, virtual reality tools can also serve to desensitize and prepare speakers for real-life situations. These techniques, along with others discussed, can significantly improve public speaking experiences.

    Visualize and prepare for public speaking engagements

    Visualization and preparation techniques, such as calming yourself and "daring to be dull," can help reduce anxiety and improve performance during public speaking engagements. Visualization, which involves mentally rehearsing the event, can desensitize you to the experience and give you a sense of agency. Calming techniques, like focusing on your breath, can help distance you from the stress and anxiety. "Daring to be dull" means focusing on getting the task done rather than striving for perfection, which can help reduce the cognitive load and allow for better connection with the audience. These techniques, which can be practiced in a virtual environment or in person, can be particularly valuable for those giving presentations or talks, such as TEDx speakers.

    Reframing anxiety as excitement

    Our mindset plays a significant role in effective communication. By changing the way we perceive anxiety during speaking engagements, we can improve our performance. Instead of viewing anxiety symptoms negatively, we should label them as signs of excitement. This cognitive reframing technique, as researched by Alison Wood Brooks, can help us relax and communicate better. Additionally, having a positive mantra like "I value to add" can boost our confidence and focus on the positive aspects of the communication opportunity. So, in essence, the way we think about communication situations can greatly impact our success.

    Managing Negative Self-talk for Effective Communication

    Managing negative self-talk is crucial for effective communication. We often engage in self-deprecating thoughts that can hinder our performance and increase anxiety. To combat this, creating a personal mantra can help boost confidence and focus on the value we bring to the table. Mantras can be simple and personal, such as "I've got this," "I'm prepared," or "Last time this went well." Personifying the inner critic and giving it a name, like "Jim," can also help rationalize negative thoughts. Remembering that others experience anxiety and that seeking help and advice can be beneficial are also essential reminders. Overall, recognizing the power of self-talk and implementing strategies to manage it can significantly improve communication skills and build confidence.

    Recognizing and managing anxiety in speaking situations

    Recognizing and normalizing anxiety in speaking situations can help reduce the pressure and make us feel less alone. Even when we see confident speakers, they may still experience nervousness. Sharing experiences and applying techniques, such as reframing the situation as a conversation or asking questions of the audience, can help manage anxiety and make us feel more comfortable. It's important to remember that developing effective communication skills is a process, not a binary state. Distracting the audience through techniques like asking questions or showing relevant videos can also help alleviate anxiety and make presentations feel more conversational. By acknowledging and addressing anxiety, we can all work towards feeling more comfortable and effective in our communication.

    Managing our physical state for mental peace

    Our physical state significantly impacts our mental state, and focusing on techniques to manage our body can help reduce anxiety and improve our overall performance. One such technique is deep belly breathing, specifically a double exhale. This involves taking a full inhale, then sneaking in a little extra air and exhaling twice as long as the inhale. This not only physiologically reduces stress but also helps us be more focused and present in the moment, rather than catastrophizing about the future. Another interesting finding is that most people experience the greatest anxiety right before speaking, so finding ways to get through that initial minute can make a big difference. Additionally, research shows that our neurons transmit information from our body to our brain much more frequently than the other way around, meaning our body's feelings influence our mind's thoughts. Therefore, managing our physical state can have a profound impact on our mental and emotional well-being.

    Managing Anxiety: Staying Present

    There are various techniques to help manage anxiety, and staying present is an effective method. The guest shared her experience with the 4-7-8 breathing technique and recommended getting present oriented through tongue twisters as another helpful method. Tongue twisters not only help in focusing on the present moment but also warm up the voice, which is essential for effective communication. Additionally, the guest mentioned that swearing can help reduce anxiety by releasing neurochemicals, although it's not recommended to do so in public. Overall, the discussion emphasized the importance of mindfulness and staying present in managing anxiety and improving communication skills.

    Improve Spontaneous Speaking with Preparation and Practice

    Effective spontaneous speaking, whether it's giving a toast, doing Q&A, or engaging in small talk, can be improved with preparation and practice. According to the expert, we often underestimate the importance of spontaneous communication and feel that we either have a natural talent for it or not. However, with the right mindset and approach, we can enhance our ability to speak on the spot. The expert suggests that preparation is key to being spontaneous. Just like athletes and musicians, communication requires practice and preparation to perform well in the moment. The expert also emphasizes the importance of focusing on structure and messaging when crafting spontaneous responses. Instead of just listing information, we should aim to provide a clear and concise message that resonates with our audience. To structure our thoughts effectively, we can follow a simple framework. Begin by acknowledging the situation and the audience, then provide your main point, and finally, offer a call to action or next steps. By following this structure, we can ensure that our message is clear, concise, and impactful. In summary, with the right mindset, preparation, and structure, we can all improve our ability to speak effectively on the spot. Whether it's giving a toast, answering questions, or engaging in small talk, these techniques can help us communicate confidently and clearly in any situation.

    Problem-Solution-Benefit and What-So-What-Now-What: Effective Communication Structures

    Our brains are not naturally wired for creating or remembering lists, but rather for stories and logical connections. To effectively communicate, it's essential to use structures that help us connect ideas and make our points clear and memorable. Two such structures discussed are the problem-solution-benefit and what-so-what-now-what. The problem-solution-benefit structure is a familiar one from advertising, where a problem is presented, followed by a solution, and the resulting benefit. This structure provides a logical flow and helps to make a compelling argument. The what-so-what-now-what structure is another effective communication tool. It consists of three questions: what, so what, and now what. The first question establishes the context and the facts, the second question explains why they matter, and the third question outlines the next steps. By using these structures, we can make our communication more effective and memorable, especially when we're under pressure or need to convey complex ideas quickly. Additionally, giving each structure a catchy name can help us remember them more easily.

    Practice, Reflect, and Seek Feedback for Effective Communication

    Effective communication requires practice, reflection, and feedback. According to the speaker, putting the structure of a communication into your own words, dissecting others' communications, and repeating, reflecting, and seeking feedback are essential for improving your communication skills. This process not only helps you remember the material better but also takes your communication to the next level. To get the reps and gain awareness, the speaker recommends joining organizations like Toastmasters, taking continuing education classes at universities, and watching videos or reading books for inspiration. However, the key is to apply what you learn and practice communication regularly. The speaker also acknowledges that it takes effort and time but emphasizes that it's worth it for the significant impact it can have on your personal and professional growth.

    Effective communication through small talk and improvisation

    Effective communication, whether it's through small talk or improvisation, requires a balance of disclosure and an understanding of the dynamics of a conversation. Toastmasters, an affordable and accessible organization, can help individuals improve their communication skills, particularly through their focus on impromptu speaking. Rachel Greenwald, an academic and matchmaker, offers valuable advice for small talk: be interested, not interesting. The goal is to set the other person up for success and keep the conversation going. It's important to match levels of disclosure in a conversation, avoiding large discrepancies that can make the interaction feel awkward. Supportive responses, which encourage the other person to share more, are crucial in maintaining a successful conversation. Shifting responses, on the other hand, can steer the conversation in a new direction. By understanding these concepts and practicing them, individuals can enhance their communication skills and build stronger relationships.

    Maintaining a balance between supporting and shifting responses in conversations

    Effective communication, including small talk, requires a balance between supporting and shifting responses. Being interested in others and asking questions is crucial, but it's equally important to share about yourself. This balance helps build intimacy and immediacy in conversations. Unfortunately, we're not naturally taught these skills, making them a valuable superpower. Classic books like "How to Win Friends and Influence People" offer timeless advice, but authenticity is key. Avoid manipulation and focus on genuine connection. Remember, people appreciate hearing their own names and seeing smiles. However, be careful not to get so focused on these techniques that you forget to truly connect. The goal is to engage in meaningful conversations, not just go through the motions. Another important aspect of communication is giving feedback. When asked for opinions, be honest and specific, offering constructive suggestions for improvement. Remember, effective communication is a skill that can be learned and honed with practice.

    Structuring Feedback for Productivity

    Feedback is an opportunity for problem-solving and collaboration. Instead of seeing it as a one-sided criticism, invite the other person to join you in addressing the issue. Kim Scott's radical candor approach is valuable, but structuring feedback effectively can make it easier to digest and more productive. Two structures mentioned are the "what, so what, now what?" and the "Four Eyes" (information, impact, invitation, implications) methods. When giving feedback, ensure you level-set the topic, share the impact on you, make an invitation, and discuss the implications. For non-work situations, like giving a toast, the same principles apply. Practice and preparation are key to delivering effective and meaningful toasts.

    Guide for giving a successful toast or tribute

    Giving a successful toast or tribute involves clearly communicating why you're there, how you're connected, sharing anecdotes, and expressing gratitude. The acronym WHAT (Why are we here? How are you connected? Anecdote or story; Gratitude or thank you) can help guide the structure of your toast. The content of the tribute can be integrated into the why or anecdote sections. Remember, keep it brief to avoid lengthy and unwanted toasts. Testing your communication with others is also important to ensure the message resonates with your audience. Don't forget to be emotional and authentic in your delivery to make the toast memorable.

    Effective communication with emotion

    Emotion plays a crucial role in effective communication, especially in situations where there is a strong connection to the audience. However, it's essential to ensure that the emotion is genuine and doesn't overshadow the message. In the case of public speaking, such as a eulogy or a toast, using anecdotes and stories to convey emotion is more impactful than simply expressing it directly. Additionally, during question-and-answer sessions, it's essential to view questions as opportunities for learning and expansion rather than threats. By answering questions cleanly and concisely, providing examples, and explaining the relevance or significance of the answers, communicators can add value and engage their audience effectively.

    Follow ADD or AAA structure for effective communication

    Effective communication involves providing a clear and complete answer. This can be achieved by following the ADD structure: Answer the question, provide a Detailed example, and Describe the relevance. When answering questions, it's important to not only provide an answer but also give a specific example that illustrates the relevance to the situation at hand. This helps to ensure that the audience fully understands the connection between the question and the response. Additionally, apologizing effectively requires acknowledging the behavior or offense, appreciating how it affected the other person, and making amends to prevent it from happening again. By following this AAA structure (Acknowledge, Appreciate, Amends), you can show that you take responsibility for your actions and are committed to making things right. When crafting responses to frequently asked questions, using the ADD or AAA structure can help ensure that all necessary information is conveyed in a clear and effective manner. This can lead to improved communication, increased understanding, and stronger relationships.

    Take the initiative, be gracious, and give it time for effective communication

    Effective communication is a skill that can be improved through initiative, grace, and compassion. Matt Abrahams, a communication expert, emphasizes the importance of taking the first step, showing empathy, and giving ample time to hone this skill. He encourages everyone to work on their communication abilities to not only find their voice but also share it with others. Matt's resources, including his podcast "Think Faster, Talk Smarter," his book by the same name, and his website madabrahams.com, offer valuable insights and tools for communication improvement. Connecting with Matt on LinkedIn is also an excellent opportunity for collaboration and learning. Remember, effective communication benefits not just the speaker but also the listener. So, take the initiative, be gracious, and give it time.

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    • 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

    A framework for finding product-market fit | Todd Jackson (First Round Capital)

    A framework for finding product-market fit | Todd Jackson (First Round Capital)

    Todd Jackson is a Partner at First Round Capital. Before moving into venture capital, he played a crucial role as VP of Product and Design at Dropbox, guiding the company until its IPO in 2018. Prior to Dropbox, Todd led product management for Twitter’s Content and Discovery teams after selling his startup, Cover, to Twitter in 2014. Before Cover, Todd oversaw product development for Facebook’s Newsfeed, Photos, and Groups. He kickstarted his career at Google as an associate product manager and eventually led product for Gmail, witnessing its growth from beta to 200 million users. In our conversation, we discuss:

    • Why product-market fit (PMF) matters

    • First Round Capital’s four-part PMF framework

    • Level one: Nascent product-market fit

    • Level two: Developing product-market fit

    • Level three: Strong product-market fit

    • Level four: Extreme product-market fit

    • Examples of companies at each level

    • How to know if you’re stuck at a level, and how to get unstuck

    • What to change if you’re stuck: persona, problem, promise, and product

    • The goals and challenges at each stage

    Brought to you by:

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    Find the full transcript at: https://www.lennysnewsletter.com/p/a-framework-for-finding-product-market

    Where to find Todd Jackson:

    • X: https://twitter.com/tjack

    • LinkedIn: https://www.linkedin.com/in/toddj0/

    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) Todd’s background

    (06:07) First Round Capital’s PMF framework

    (09:07) Why product-market fit is so important

    (11:02) Who can benefit from this framework

    (12:55) The product-market fit method

    (16:54) Broad overview of the framework

    (21:35) Level one: nascent product-market fit

    (33:16) The four P’s

    (39:13) Level two: developing product-market fit

    (49:13) Signs you’re stuck at level two, and what to do

    (55:12) Level three: strong product-market fit

    (01:00:17) Signs you’re stuck at level three, and what to do

    (01:02:22) Level four: extreme product-market fit

    (01:06:55) Rough timelines for each level

    (01:11:18) A quick recap of the framework

    (01:12:15) Diving deeper on the four P’s: what to do if you’re stuck

    (01:13:56) Dollar-driven discovery

    (01:25:11) Apply for the product-market-fit method program

    Referenced:

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

    • Twitter Acquires Cover: https://www.vox.com/2014/4/7/11625332/twitter-acquires-cover-an-android-mobile-startup

    • Dropbox: https://www.dropbox.com/

    • Rahul Vohra on LinkedIn: https://www.linkedin.com/in/rahulvohra/

    • How Superhuman Built an Engine to Find Product Market Fit: https://review.firstround.com/how-superhuman-built-an-engine-to-find-product-market-fit/

    • How to validate your startup idea: https://www.lennysnewsletter.com/p/validating-your-startup-idea

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

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

    • A guide for finding product-market fit in B2B: https://www.lennysnewsletter.com/p/finding-product-market-fit

    • Product-market fit method: http://pmf.firstround.com/

    • Stripe: https://stripe.com/

    • Plaid: https://plaid.com/

    • Paths to PMF: https://review.firstround.com/series/product-market-fit/

    • WeWork: https://www.wework.com/

    • Casper: https://casper.com/

    • Vanta: https://www.vanta.com/

    • Christina Cacioppo on LinkedIn: https://www.linkedin.com/in/ccacioppo/

    • Ramp: https://ramp.com/

    • Velocity over everything: How Ramp became the fastest-growing SaaS startup of all time | Geoff Charles (VP of Product): https://www.lennyspodcast.com/velocity-over-everything-how-ramp-became-the-fastest-growing-saas-startup-of-all-time-geoff-charl/

    • Jack Altman on LinkedIn: https://www.linkedin.com/in/jackealtman/

    • Lattice: https://lattice.com/

    • Zachary Perret on LinkedIn: https://www.linkedin.com/in/zperret/

    • Positioning: https://www.lennysnewsletter.com/p/positioning

    • Retool: https://retool.com/

    • David Hsu on LinkedIn: https://www.linkedin.com/in/dvdhsu/

    • Persona: https://withpersona.com/

    • Rick Song on LinkedIn: https://www.linkedin.com/in/rick-song-25198b24/

    • Lloyd Tabb on LinkedIn: https://www.linkedin.com/in/lloydtabb/

    • Looker: https://en.wikipedia.org/wiki/Looker_(company)

    • Jason Boehmig on LinkedIn: https://www.linkedin.com/in/jboehmig/

    • Ironclad: https://ironcladapp.com/

    • Lessons in leadership | Scaling an org and tactical management advice | Jack Altman (Lattice): https://www.youtube.com/watch?v=cZzXqf61mrQ

    • Filip Kaliszan on LinkedIn: https://www.linkedin.com/in/kaliszan/

    • Verkada: https://www.verkada.com/

    • Ali Ghodsi on LinkedIn: https://www.linkedin.com/in/alighodsi/

    • Databricks: https://www.databricks.com/

    • Stripe Radar: https://stripe.com/radar

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

    • Square Stand: https://squareup.com/shop/hardware/us/en/products/ipad-pos-stand-integrated-card-reader

    • Cash App: https://cash.app/

    • Square Checking: https://squareup.com/us/en/campaign/banking/checking

    • Square Loan: https://squareup.com/help/us/en/article/5654-get-started-with-square-capital

    • Casey Winters on LinkedIn: https://www.linkedin.com/in/caseywinters/

    • How to sell your ideas and rise within your company | Casey Winters, Eventbrite: https://www.lennyspodcast.com/how-to-sell-your-ideas-and-rise-within-your-company-casey-winters-eventbrite/

    • Josh Kopelman on LinkedIn: https://www.linkedin.com/in/jkopelman/

    • The art and science of pricing | Madhavan Ramanujam (Monetizing Innovation, Simon-Kucher): https://www.lennyspodcast.com/videos/the-art-and-science-of-pricing-madhavan-ramanujam-monetizing-innovation-simon-kucher/

    • Simon Kucher: https://www.simon-kucher.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.



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