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    An inside look at Figma’s unique GTM motion | Claire Butler (first GTM hire)

    Building love for your product among customers is essential as it leads to advocacy and enables the expansion of your customer base.

    enSeptember 07, 2023

    About this Episode

    Brought to you by Vanta—Automate compliance. Simplify security | Mixpanel—Event analytics that everyone can trust, use, and afford | AssemblyAI—Production-ready AI models to transcribe and understand speech

    Claire Butler was Figma’s first GTM hire and their 10th employee. She led Figma’s early GTM strategy from stealth through monetization. She also helped the team through the journey to find product-market fit and built the team that drove Figma’s unique bottom-up growth motion. Eight years later, as Senior Director of Marketing, she continues to lead Figma’s bottom-up growth motion, along with community, events, social, advocacy, and Figma for education. In this episode, we discuss:

    • An in-depth look at Figma’s bottom-up GTM motion

    • Why you need to start with individual contributors (ICs) loving your product

    • How to spread adoption within the organization

    • How “designer advocates” have played a critical role in Figma’s growth

    • The freemium strategy that drove massive growth for Figma

    • How to leverage product champions

    • When to leave stealth

    • Early-stage metrics, and why they are often unreliable

    • Advice for people looking to join a startup

    Find the full transcript at: https://www.lennyspodcast.com/an-inside-look-at-figmas-unique-gtm-motion-claire-butler-first-gtm-hire/#transcript

    Where to find Claire Butler:

    • Twitter/X: https://twitter.com/clairetbutler

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

    Where to find Lenny:

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

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

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

    In this episode, we cover:

    (00:00) Claire’s background

    (03:47) The huge branding decision that Claire made on day one at Figma

    (07:45) The most stressful memory of early days at Figma

    (09:55) Advice for people looking to join a startup

    (12:55) What a bottom-up go-to-market motion is

    (17:12) Figma’s unique approach to bottom-up GTM

    (18:52) Figma’s launch out of stealth 

    (23:01) Signals vs. hard metrics in the early days 

    (24:50) How Figma won over Microsoft

    (30:08) How to win over ICs

    (32:00) How to establish credibility

    (37:38) Customer obsession in action

    (41:11) Why getting users to love your product is so vital

    (44:01) How Figma used Twitter as its primary channel in the early days

    (49:06) Transparency and authenticity

    (49:52) GTM tactics at scale

    (52:09) “Little big updates” at Figma

    (54:16) Figma’s acquisition, and why it was one of the hardest days of Claire’s career

    (57:10) Figma’s core values

    (58:06) The Config conference

    (1:00:21) Spreading your product within the organization

    (1:02:09) The pricing tiers at Figma

    (1:07:35) The role of designer advocates

    (1:10:57) Design systems

    (1:16:12) Leveraging internal champions

    (1:17:53) Accelerating spread at scale

    (1:19:14) What types of companies are a good fit for bottom-up GTM

    (1:24:16) A summary of the bottom-up GTM model

    (1:25:27) Lightning round

    Referenced:

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

    • John Lilly on LinkedIn: https://www.linkedin.com/in/johnlilly/

    • Ivan Zhao on LinkedIn: https://www.linkedin.com/in/ivanhzhao/

    • Xamarin: https://dotnet.microsoft.com/en-us/apps/xamarin

    • Josef Müller-Brockmann: https://en.wikipedia.org/wiki/Josef_M%C3%BCller-Brockmann

    • Datadog: https://www.datadoghq.com/

    • Coda: https://coda.io/

    • Oren’s Hummus on Instagram: https://www.instagram.com/orenshummus/

    • Intercom: https://www.intercom.com/

    • How Coda builds product: https://www.lennysnewsletter.com/p/how-coda-builds-product

    • Dylan Field on Twitter: https://twitter.com/zoink

    • Dylan’s tweet: https://twitter.com/zoink/status/1566566649712431105

    • Little Big Updates: https://www.figma.com/blog/little-big-updates-august-2022/

    • Sho Kuwamoto on Twitter: https://twitter.com/skuwamoto

    • Kris Rasmussen on Twitter: https://twitter.com/kris_rasmussen

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

    • Tom Lowry on LinkedIn: https://www.linkedin.com/in/thomaslowry

    Atomic Design: https://atomicdesign.bradfrost.com/

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

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

    Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity: https://www.amazon.com/Radical-Candor-Revised-Kick-Ass-Humanity/dp/1250235375

    Dare to Lead: Brave Work. Tough Conversations. Whole Hearts: https://www.amazon.com/Dare-Lead-Brave-Conversations-Hearts/dp/0399592520

    100 Foot Wave on HBO: https://www.hbo.com/100-foot-wave

    Atomic Habits: An Easy & Proven Way to Build Good Habits & Break Bad Ones: https://www.amazon.com/Atomic-Habits-James-Clear-audiobook/dp/B07RFSSYBH

    • Noah Weiss on Lenny’s Podcast: https://www.lennyspodcast.com/the-10-traits-of-great-pms-how-ai-will-impact-your-product-and-slacks-product-development-process/

    • How to create an exceptional coverage plan for your parental leave (Tamara Hinckley): https://www.lennysnewsletter.com/p/how-to-create-an-exceptional-coverage

    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

    • Addressing customer concerns and maintaining strong relationships requires dedication and a problem-solving attitude, even in the face of unforeseen obstacles.
    • Taking ownership, making decisive actions, and balancing strategic decisions with mundane tasks are crucial in the early days of a startup. Seeking guidance and validation is also important for success.
    • Trust your intuition and seek validation from those who have faith in your decision to make successful career choices.
    • Figma's bottom-up strategy, focusing on individual designers and their advocacy, has allowed them to achieve revenue growth without a sales team and utilize their free tier to generate sales leads.
    • Figma's success can be attributed to their commitment to improving their design tool for individual contributors, recognizing that even small updates can make a significant impact.
    • Emotional reactions and positive feedback from potential customers can be a strong indicator of a product's readiness for launch, even if metrics may not always provide reliable insights in the early stages.
    • Metrics alone cannot determine product market fit. It requires finding signal through anecdotal evidence, speaking to users, and employing organic growth tactics within organizations.
    • Identifying and leveraging internal champions can drive the spread and adoption of a product within an organization, while persistence and seizing opportunities are essential for gathering feedback and connecting with potential users.
    • To successfully engage with designers, focus on showcasing technical feats, sharing decision-making processes, and providing in-depth technical content that appeals to their interests.
    • Figma's success in building credibility came from their commitment to providing valuable information, involving their audience, and prioritizing quality over quantity in their content creation and promotion.
    • Building love for your product among customers is essential as it leads to advocacy and enables the expansion of your customer base.
    • Building a successful product goes beyond acquiring users. By connecting with potential users where they already are and cultivating a sense of passion, you can foster growth and success.
    • By actively engaging with users, sharing best practices, and gathering feedback, businesses can build a strong presence on Twitter, attract followers, and gain trust from their audience.
    • Building relationships with advocates can drive adoption, maintain authenticity, and involve users in the product development process, despite the challenges of scaling and a high volume of bug requests.
    • Figma prioritizes user experience by addressing small issues, launching annual updates, sharing postmortems, and communicating directly with users, fostering strong relationships and product enhancement.
    • Figma's commitment to transparency and open communication with users has proven to be effective in building trust and maintaining a strong connection. By prioritizing listening, fixing bugs, and responding directly to feedback, Figma creates a valuable and practical user experience.
    • By allowing users to easily sign up for a free account and share their work within organizations, Figma gained user trust and advocacy, leading to significant growth.
    • Figma offers different tiers catering to different user needs, with a continuous process of feature selection and pricing structure. Their unique approach of charging only for editors and allowing unlimited viewers drives adoption and expands their reach within organizations.
    • Designer advocates play a crucial role in sales by effectively communicating product benefits, bridging the gap between customers and the product team, and increasing the likelihood of closing deals.
    • Design systems improve efficiency, consistency, and collaboration by providing predefined components that can be easily reused, leading to time and resource savings and ensuring consistency across teams and projects.
    • In order for a product to be successfully adopted within an organization, it is important to provide value to individual contributors, cultivate relationships with internal champions, and support their growth to build credibility and achieve widespread adoption.
    • Consider factors like target audience, existing community, and potential challenges when scaling a sales team and incorporating new methods for growth.
    • Building a culture of collaboration requires strong leadership, trust in intuition, focus on credibility and transparent relationships, and strategic efforts to spread and support the product within the organization.
    • By embracing consistent pressure and steady progress, we can achieve long-term success and fulfillment in all aspects of life.
    • Figma offers versatility beyond traditional design projects, enabling users to gather ideas, create mood boards, and effectively communicate during the renovation process. Seeking support and advice from others is crucial for success.

    📝 Podcast Summary

    Going the Extra Mile for Customer Satisfaction

    Early successes can come with unexpected challenges. When Figma secured Coda as their first user, they were ecstatic. However, a technical issue with Philippe's MacBook threatened to derail the partnership. Despite finding no problem with the servers, Dylan had to personally drive down to Palo Alto to fix the issue and ensure the product could be used. This anecdote highlights the importance of going the extra mile to address customer concerns and maintain strong relationships. Even when faced with unforeseen obstacles, Figma was committed to delivering a working solution. This demonstrates the dedication and problem-solving attitude that contributed to their success in becoming a leading product in the industry.

    Early Days at Figma: The Blend of Strategy and Hands-On Tasks

    The early days at Figma were characterized by a combination of high-level strategic decisions and practical tasks. Claire Butler recalls how she played a role in the decision to change the name of the product to Figma and how quickly things moved. This highlights the importance of taking ownership and making decisive actions. Additionally, she shares the memory of having to carry bags of ice for a meetup, emphasizing the need for individuals to handle both strategic and mundane tasks in a startup environment. Furthermore, Claire discusses the challenges she faced when launching Figma out of stealth, particularly the lack of support and limited confidence in decision-making. This signifies the difficulty of being the sole marketer and go-to-market person in a startup, underscoring the importance of finding reliable sources of guidance and validation.

    Trusting intuition and seeking validation for successful career choices.

    When faced with a decision to join a company or pursue a new venture, it is important to trust your intuition and believe in the idea. Claire Butler's decision to join Figma early on was influenced by her logical understanding of the company's premise and how it clicked with her personal experiences as a marketer. Additionally, the social proof from people she trusted, such as Dylan and investors like Danny Rimer and John Lilly, played a role in her decision-making process. This highlights the significance of seeking validation from individuals who have faith in the company or venture. Ultimately, combining belief in the idea with the support and trust of others can lead to successful career choices and opportunities.

    Figma's Unique Approach: Empowering Individual Contributors for Organic Growth

    Figma's go-to-market motion is centered around a unique bottom-up approach. Figma focuses on individual contributors, particularly designers, who use their tool extensively and build a strong relationship with the product, company, and brand. These individual contributors become advocates within their communities, spreading the product and eventually driving revenue from larger companies. Figma's motion is different from the traditional top-down approach seen in many SaaS companies, where the focus is on executive buyers. By prioritizing the satisfaction and adoption of practitioners, Figma has been able to achieve efficient and self-serve revenue growth without a sales team for the first three years. Additionally, Figma's free tier plays a crucial role in generating sales and marketing qualified leads.

    Figma's success: Prioritizing user needs and focusing on tool functionality.

    Figma's success in the bottom-up go-to-market approach can be attributed to their obsession with the quality and craft of their design tool. Figma understands the significance of even small updates that improve the workflow for individual contributors who spend countless hours using the tool. They prioritize the needs and preferences of their users, recognizing that a simple change like reducing one click can make a huge difference for a designer. While collaboration and expansion are important aspects of their product, Figma's core focus remains on the tool itself and ensuring it works well. This dedication to the editor and its functionality sets them apart from other companies in the market. Additionally, the decision to come out of stealth and launch was driven by a need for momentum and motivation after years of quiet development.

    The importance of product-market fit and customer feedback in determining the success of a product launch.

    Product market fit is crucial for a successful launch. Claire Butler and her team at Figma wanted to get out of stealth mode but needed to ensure that their product would be successful. The core differentiator for Figma was its multiplayer feature, which was still being developed. Despite not having all the key features ready, Claire wanted to gauge public interest and sought feedback from designers. She found confidence in knowing that designers were excited and willing to try the tool, even if they may not have been ready to use it as a team. This emotional reaction and pull from potential customers gave her the assurance that Figma was ready to launch. In the early stages, metrics may not always provide reliable insights into product success.

    The Importance of Finding Signal and Organic Growth in Achieving Product Market Fit

    Metrics alone cannot determine product market fit. Claire emphasizes that optimizing small metrics, such as a 5% improvement in email conversions, does not necessarily indicate if a product is working or not. Instead, she highlights the importance of finding signal, such as anecdotal evidence and speaking to users who genuinely love the product. Lenny further solidifies this point by outlining the step-by-step process of achieving product market fit, which includes getting companies to use the product, ensuring continued usage, and eventually securing payment. The conversation also highlights the bottoms-up model and the scrappy tactics employed by the Figma team, including reaching out to Microsoft through personal connections. Overall, identifying product market fit requires a combination of intuition, feedback, and organic growth within organizations.

    The role of internal champions in product success and adoption

    Internal champions play a crucial role in the success and spread of a product within an organization. In the case of Figma, these internal champions were responsible for starting the adoption process and spreading the use of the product to other individuals and teams. By analyzing Node graphs that visualized the spread of Figma within different organizations, the company was able to identify these champions and their influence in driving adoption. Understanding the power of these champions became a key insight in Figma's go-to-market strategy. Additionally, the conversation highlights the importance of persistence and leveraging every opportunity, such as chance encounters in shared rides, to connect with potential users and gather feedback.

    Building credibility and engaging with a technical audience through transparency and user involvement.

    Building credibility, involving users in product development, establishing a long-term relationship, and being transparent are crucial strategies for successfully engaging with a technical audience. In the early days, Claire learned that designers don't want to be marketed to, and traditional product marketing methods don't work. Instead, designers are interested in technical features and understanding how they can use them. To build authenticity and credibility, Figma focused on showcasing the technical feats of their tool and sharing their design team's decision-making process. They provided technical content that gained interest and went viral, and delved into the deep details of their product decisions. Understanding the audience's level of understanding and avoiding basic explanations also played a role in establishing credibility.

    Building Trust Through High-Quality Content and Customer Engagement

    Building credibility and gaining customer trust can be achieved by producing high-quality content and engaging with customers directly. Figma's success in technical content stemmed from their commitment to providing valuable information through blog posts and actively involving their target audience in the product development process. By hiring a designer advocate to work alongside the marketing team, Figma was able to represent the users' interests and bridge the gap between design and engineering. This approach not only strengthened their go-to-market strategy but also facilitated continuous improvement to meet customer needs. Furthermore, Figma's emphasis on quality over quantity in their content creation and strategic promotion through platforms like Hacker News and Twitter further enhanced their reputation and drew attention to their innovative ideas.

    The importance of building strong customer relationships for business success.

    Building strong relationships with your customers, especially in the early days, is crucial for success. Claire Butler emphasizes the importance of listening to feedback and focusing on getting one person to use and love your product. She shares a story about their first user, Coda, and how they went above and beyond, driving to their office and fixing technical issues just to ensure they could use the product. This hands-on approach and personalized support helped build credibility and a strong relationship with their customers. As the company grew, they implemented tools like Intercom to continue engaging with users and addressing their needs. Building love for your product among customers is essential because it leads to advocacy and enables the expansion of your customer base.

    Cultivating Passion and Love for Your Product to Drive Success

    Building a successful product requires more than just acquiring users. To transform users into champions and achieve scalability, it is crucial to cultivate a sense of passion and love for the product. Simply using the product is not enough to inspire others to advocate for it. This means going beyond traditional marketing channels and finding ways to connect with potential users where they already are. In the early stages, it may be necessary to reach out to users instead of expecting them to come to you. By identifying existing communities and platforms that align with your target audience, you can establish credibility, build relationships, and ultimately foster the growth and success of your product.

    Leveraging Twitter for Business Success

    Building a strong presence on Twitter and utilizing it as a platform for networking and engagement can be extremely valuable for a business. Figma, a design tool, successfully utilized Twitter to connect with influencers, share best practices, and gather feedback from the design community. They focused their efforts on Twitter as their primary channel and used a tool developed by one of their engineers to identify influencers and understand their network of followers. By actively engaging with users, answering questions, and sharing technical content, Figma built a highly engaged community on Twitter. This approach allowed them to passively attract followers and build trust over time, ultimately leading to confident and loyal users. The key to their success was placing a personal face behind the brand and prioritizing feedback as a means of improvement.

    The Importance of Building Relationships and Maintaining Transparency with Users

    Building relationships with users and maintaining transparency and authenticity are crucial at all stages of company growth. In the early days, being transparent with users and establishing personal connections comes naturally. However, as the company scales, it becomes harder to maintain that level of interaction with a larger user base. Despite the challenges, it is important to continue being honest, human, and transparent with users. Building relationships with advocates who are passionate users and technical experts can help drive adoption and maintain authenticity. These advocates play a key role in providing feedback, pitching the company, and building credibility. Additionally, the conversation highlights the importance of involving users in the product development process, even with a high volume of bug requests and the need to focus on new feature development.

    Figma's Commitment to Quality and Transparency

    Figma places a strong emphasis on quality and improving the user experience. One way they achieve this is through their "quality weeks" with engineering, where engineers address small issues and annoyances reported by users. These updates are packaged together and launched as "little big updates" every year, which has become one of their most popular launches. Figma also values transparency, even when facing challenges or downtime. They choose to be open and accountable by sharing postmortems and taking full responsibility for any issues. Additionally, when making significant announcements, such as an acquisition, Figma prioritizes direct communication with their users, rather than hiding behind the brand. These practices demonstrate Figma's commitment to continually enhancing their product and maintaining strong relationships with their users.

    The Power of Transparency and Direct Communication in Building Trust

    Transparency and direct communication with users are crucial for success. Figma's approach of holding open public forums and being honest and transparent with their users has proven to be effective in building trust and maintaining a strong connection. Transparency is embedded in Figma's values, even though it may not be explicitly listed. They prioritize listening to users, fixing bugs, and responding directly to feedback. Additionally, Figma's Config conference is an example of how they listen to their users to create valuable content. By involving their users in the process, Figma not only provides technical content but also helps speakers grow their own profiles and become thought leaders. This focus on practicality and tangible outcomes resonates with users, similar to the approach taken in this podcast and newsletter.

    Removing Barriers for Success

    Making a product easy to try and share is crucial for its success and growth. Figma, a design tool, implemented strategies to allow users to easily sign up for a free account and create free teams to share their work within their organizations. They realized the importance of giving users time and confidence to try the tool before introducing payment. Initially, Figma had a paywall for collaboration, but they changed it to unlimited collaborators with limitations on the number of files. This decision significantly impacted Figma's metrics and allowed users to build advocacy and gain trust in the product before committing to payment. Removing barriers to trying and sharing the tool was a monumental decision that propelled Figma's growth engine.

    Pricing and Packaging: Key to Product Success and Growth

    Pricing and packaging decisions are crucial for the success and growth of a product. Figma, a design collaboration tool, offers different tiers to cater to different user needs. The free tier allows users to access basic features, while the pro tier requires a subscription but offers more advanced capabilities. The org tier is aimed at enterprise-level users and requires a sales conversation to upgrade. The decision of what features to offer in each tier and how to structure pricing is a continuous process influenced by the introduction of new features and customer feedback. Additionally, Figma's approach of charging only for editors and allowing unlimited viewers helps increase adoption and expand its reach within organizations.

    The value of designer advocates in sales and customer feedback

    Having designer advocates, like Tom, can be incredibly valuable for a company. These advocates are individuals who have a deep understanding and passion for the product, and they can effectively communicate its benefits to other designers. They play a crucial role in the sales process, as they can relate to the needs and challenges of potential customers on a technical level. These designer advocates bring credibility and expertise to the table, which can significantly increase the likelihood of closing deals. Additionally, they serve as a bridge between the product team and customers, synthesizing valuable feedback and providing important context. Building teams with such advocates can be a game-changer for companies looking to establish trust and effectively market their products to a technical audience.

    The Importance and Benefits of Design Systems

    Design systems are crucial for organizations to improve efficiency and consistency in product development. Design systems provide a library of predefined components, such as buttons, with specific styles and properties that can be easily reused by designers and developers. By utilizing design systems, organizations can avoid the need to recreate components from scratch, leading to time and resource savings. Furthermore, design systems ensure consistency across various teams and projects, eliminating discrepancies and confusion. While implementing design systems can be challenging, it is an investment that pays off by streamlining communication and collaboration between design and engineering teams. Figma's focus on design systems, as highlighted in their meetups, conferences, and marketing efforts, demonstrates the importance of this concept in driving organizational growth and upgrade opportunities.

    Value, Relationships, and Empowerment: Key Factors for Successful Product Adoption

    In order for a product to be successfully adopted within an organization, it must provide value to individual contributors (ICs) on their own. This is especially true for technical products, as ICs who deeply care about their craft are more likely to invest time and effort in learning and understanding the product. Additionally, cultivating and maintaining relationships with internal champions is crucial. These champions play a vital role in spreading the product and should be supported and empowered beyond just the tool itself. By helping these champions grow in their careers and amplifying their expertise, the organization can build credibility and create a positive feedback loop. As the company scales, it becomes essential to continue advocating for bottom-up adoption strategies alongside top-down initiatives.

    Scaling a sales team and implementing new strategies for growth.

    Scaling a sales team and implementing traditional methods and motions can be challenging as a company grows. It is important to protect the elements that have made the company successful while also incorporating new strategies. However, not every B2B SaaS company may be a good fit for this approach. It is beneficial if the target audience is technical and cares deeply about their tools. Having an existing community within the target audience and connection points within the organization can also help in the process. Additionally, it is necessary to consider the disadvantages and challenges of convincing users to switch to a new tool, such as in the case of Figma.

    Fostering collaboration and transforming design organizations through strong leadership and belief in the value of collaboration.

    Building a culture of collaboration within design organizations requires strong leadership and a belief in the value of collaboration. Initially, designers may resist the shift towards collaboration, preferring to work individually and present their work when ready. However, with the right executive and leader who believes in collaboration, the culture can be transformed. Trusting intuition and relying on signals rather than immediate metrics is crucial in this process. It is also essential to focus on building credibility, connecting with users, and fostering transparent relationships to make individual contributors love the product. To spread the product within the organization, it is necessary to make sharing and trying the product easy, involve designer advocates in the sales process, identify and target key drivers of adoption, and support and highlight champions.

    The Power of Consistent Pressure and Steady Progress

    Consistent pressure over time is more important than immediate accomplishments. Claire Butler shares her motto of not putting too much pressure on herself to achieve things immediately, but rather focusing on steady progress and not giving up. This mindset applies to various aspects of life, whether it's in her career or personal goals. It is a reminder to keep working towards our aspirations and not get discouraged by slow progress or setbacks. This motto aligns with the idea of having grit and perseverance, which can lead to long-term success and fulfillment. It is a valuable perspective to adopt, emphasizing the importance of staying dedicated and not giving up on our journey.

    Utilizing Figma for Home Renovation and Interior Design

    Figma, particularly FigJam, has unexpectedly become a valuable tool for home renovation and interior design projects. Claire Butler explains how she uses Figma to gather ideas from Pinterest and create mood boards, allowing her to effectively communicate with her partner during the renovation process. She also mentions drawing out rooms and modeling designs on the iPad using Figma. This demonstrates the versatility of Figma beyond traditional design projects. Additionally, the conversation touches on the topic of parenting while juggling a career, with Lenny offering helpful tips and resources. Overall, this highlights the importance of finding innovative ways to use tools like Figma and seeking support and advice from others in similar situations.

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    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:

    Sidebar—Accelerate your career by surrounding yourself with extraordinary peers

    Webflow—The web experience platform

    Vanta—Automate compliance. Simplify security

    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

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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:

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

    Where to find Vikrama Dhiman:

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

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

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

    Where to find Lenny:

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

    • X: https://twitter.com/lennysan

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

    In this episode, we cover:

    (00:00) Vikrama’s background

    (03:56) Three common traits among great PMs

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

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

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

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

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

    (23:26) The art of the pushback

    (26:55) Common factors that impede career growth

    (33:39) Vikrama’s personal reflections

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

    (46:28) The ambiguity of the PM role

    (51:47) The 8 axis for PM growth

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

    (59:30) Lightning round

    Referenced:

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

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

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

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

    • Oracle: https://www.oracle.com/

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

    Lenny may be an investor in the companies discussed.



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

    Business strategy with Hamilton Helmer (author of 7 Powers)

    Business strategy with Hamilton Helmer (author of 7 Powers)

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

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

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

    • How power relates to strategy

    • The difference between a moat and a power

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

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

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

    Where to find Hamilton Helmer:

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

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

    • Website: https://7powers.com/

    Where to find Lenny:

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

    • X: https://twitter.com/lennysan

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

    In this episode, we cover:

    (00:00) Hamilton’s background

    (04:08) When power becomes important

    (08:24) How strategy relates to power

    (12:09) How power informs strategy

    (14:46) The sequence of powers

    (21:13) Common misconceptions

    (24:39) Network effects vs. network economies

    (26:58) Uber’s success

    (29:16) Moats vs. powers

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

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

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

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

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

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

    (56:35) Optimism for the future

    (59:25) Lightning round

    Referenced:

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

    • Ogilvy: https://www.ogilvy.com/

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

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

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

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

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

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

    Lenny may be an investor in the companies discussed.



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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

    Brought to you by:

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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

    Brought to you by:

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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:

    Paragon—Ship every SaaS integration your customers want

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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:

    Orb—The flexible billing engine for modern pricing

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    Paragon—Ship every SaaS integration your customers want

    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