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    • The Benefits and Freedom of Bootstrapping for Successful EntrepreneursBootstrapping allows entrepreneurs to prioritize profits, have more freedom and flexibility, and eliminate the pressure to constantly seek funding, leading to a more fulfilling work experience.

      Bootstrapping can be a viable and rewarding alternative to the traditional venture route of raising money from investors. The success story of 37signals, with its profitable business for 24 years and over 100,000 paying customers, showcases the benefits of bootstrapping. By focusing on making money and prioritizing profits, entrepreneurs can develop the fundamental skill needed to run a successful business. This approach allows for more freedom and flexibility, as there are no investors or boards to answer to. Moreover, bootstrapping can lead to a more fulfilling and enjoyable work experience, as it eliminates the pressure to constantly seek funding and achieve unrealistic growth. Ultimately, the key to building a successful business lies in exploring all the different options available, including the possibility of bootstrapping.

    • The Value of Bootstrapping and Efficiency in Building a Sustainable BusinessNot every founder or industry needs to pursue venture funding and rapid growth. Bootstrapping and focusing on efficiency can lead to long-term profitability and success, aligning with the unique needs of the business.

      Building a venture-backed business may not be the best path for every founder or every industry. While raising money and growing as quickly as possible may seem like the conventional route to success, it may not be the most profitable or sustainable approach. For businesses like software companies that have low upfront costs and high-profit margins, bootstrapping and focusing on efficiency rather than rapid growth can lead to long-term profitability. Instead of succumbing to the pressure of going big and chasing unicorn status, founders should consider finding their own niche and identifying a sustainable path to success that aligns with the unique needs and nature of their business.

    • Staying Small and Focused: Basecamp's Recipe for SuccessBy prioritizing simplicity, small teams, and profitability, Basecamp avoids complexity, supports its target customers effectively, and builds a high-quality user experience without unnecessary expenses.

      Basecamp's success lies in its intentional decision to stay small and focused. By not pursuing enterprise customers and maintaining a simple pricing structure, they avoid the complexity and support costs that come with catering to a wide range of companies. Instead, they offer one product with unlimited users, allowing them to prioritize building a high-quality and user-friendly experience. Their small team size enables efficient decision-making and quick feature development, avoiding the pitfalls of large-scale projects and unnecessary expenses. Basecamp believes in the power of constraints, simplicity, and small teams, which not only keep them honest but also allow them to effectively serve their target customer base of small businesses. Their approach rejects the notion that success requires massive scale and emphasizes the importance of profitability and individual gain.

    • Success through enjoyment, value, and infinite gamesSuccess is not just about profitability, but also about finding joy in what you do, valuing what feels right, and focusing on building something meaningful for the long term.

      Success, for Jason Fried and his company, is about wanting to do something again. If they enjoy it, find it worthwhile, and would gladly repeat the experience, then it is considered successful. Profitability is also important, but it is not the sole focus. They don't analyze each product's profitability individually, but rather look at their collective profit. They value what feels right and the decent thing to do, rather than solely relying on data or financial goals. They have no plans for external investments, going public, or selling the business because they find joy in playing an infinite game, such as building great relationships and a company they want to continue working at forever.

    • The Challenges of Staying in BusinessBuilding a successful business requires dedication, hard work, and a genuine passion for what you're doing. It's about enduring plateaus, competition, and market changes while staying committed to your craft.

      Entrepreneurship is a job in itself. While it may seem glamorous to start a business, the real challenge lies in staying in business and enduring the ups and downs that come with it. Starting a business is easy, but staying in business requires dedication, hard work, and a genuine passion for what you're doing. It's about enduring moments of plateaus and navigating through competition and changes in the market. Building a successful business is a long-term commitment, and it's important to focus on what you truly enjoy and want to keep doing for as long as possible. So, let's celebrate the "stay ups" – those who are in it for the long haul and are dedicated to their craft.

    • Jason Fried's Journey: Reflections on Challenges and Rediscovered EnergyRegularly assessing our motivation and passion in our work is crucial for success and growth. Being self-aware allows us to identify missed opportunities and explore different approaches.

      After being in the business for almost 25 years, Jason Fried has experienced both excitement and doubts about continuing his journey. Despite the challenges and the longing for the early days, he currently feels a surge of energy from the business. However, he remains conscious of how his energy levels fluctuate over time. He ponders what someone else would do if they had the chance to run the company, believing that they would focus more on growth and tap into missed opportunities. This curiosity about a different approach is always in the back of his mind. Overall, Jason's experience teaches us the importance of self-awareness and regularly assessing our motivation and passion for what we do.

    • Finding Success on Your Own TermsFocusing on your current work and finding contentment in it, rather than constantly seeking new opportunities, can lead to a more sustainable and satisfying business journey. Understand your personality, product, and goals to choose the right path for your success.

      There are different paths to success in business, and not every company needs to pursue the traditional venture scale route. Jason Fried emphasizes the importance of focusing on what you're currently doing and finding satisfaction in that, rather than constantly chasing new opportunities. He acknowledges that while there may be missed opportunities and potential for growth, he is content with running his business in a more relaxed and sustainable manner. Fried recognizes that the majority of businesses operate in a similar way, without large amounts of funding or the pressure to build billion-dollar companies. It's essential to understand your own personality, product, and goals when deciding which path is best for your business.

    • Challenging the "go big or go home" mentality in businessSuccess in business doesn't always mean rapid growth and unicorn status. It's about finding sustainable ways to build a profitable business that aligns with your goals and values.

      There are different paths to success in the business world. While many in the industry push for rapid growth and unicorn status, Jason Fried's perspective challenges this notion. He believes that there are numerous opportunities for businesses to thrive without chasing the "go big or go home" mentality. Instead, he advocates for optionality and finding sustainable ways to build a successful business. Fried emphasizes the importance of considering all the different positions a company can land in, rather than focusing solely on the limited slots available for massive ventures. By embracing a mindset that aligns with their goals and values, entrepreneurs can create profitable and fulfilling businesses without conforming to a one-size-fits-all approach.

    • Shape Up: A Six-Week Cycle for Efficient Product DevelopmentBy setting a fixed six-week budget for individual features and keeping teams small, 37signals' Shape Up framework maximizes productivity and ensures projects stay on track, with flexibility for adjustments and abandonment when necessary.

      37signals has developed a unique framework called Shape Up for building products. At the core of this approach is the concept of a six-week cycle. Instead of estimating how long a project will take, they set an appetite of six weeks as their budget for any individual feature. This prevents projects from dragging on indefinitely. Additionally, they keep teams small, consisting of just a designer and engineer, to maximize productivity. The team is given autonomy to figure out the simplest and most effective way to complete the work within the allocated time frame. This approach relies on continuous communication and flexibility, allowing for adjustments and trade-offs along the way. Ultimately, if a project cannot be completed within the six-week period, it is often abandoned to maintain the integrity of the system.

    • Managing long-running projects and avoiding employee burnout.Setting clear time limits, prioritizing work, and gradually introducing new methods can help businesses avoid demoralizing projects and retain their employees.

      It is important to avoid long-running projects that never seem to end. These types of projects can be demoralizing and lead to employees wanting to leave their jobs. To prevent this, it is crucial to set clear time limits and prioritize work accordingly. By adopting an approach that focuses on fixed effort and expected impact, businesses can ensure that projects are manageable and have clear endpoints. Making promises about timelines can often lead to disappointment, so it is better to avoid making promises altogether. While changing the way a company works can be challenging, it is possible to gradually introduce new methods by starting with low criticality projects.

    • Starting small and building confidence in adopting a new way of working.Begin with low-stakes projects, take breaks to reflect and explore, and trust your instincts for effective decision-making.

      It's important to start with low-stakes projects when adopting a new way of working. By picking things that don't matter much if you make mistakes or aren't successful, you can practice and improve without fear of negative consequences. This approach allows you to build confidence and skills before applying the new method to more critical tasks. Trying something new on something highly important right away can be overwhelming and may discourage future attempts if it doesn't go well. By gradually introducing the new way of working and taking the pressure off, you create space for growth and learning. It's also essential to have periods of rest and rejuvenation after intense work cycles, allowing for reflection and exploration of other tasks. Balancing different types of work and avoiding continuous sprints can lead to better overall productivity and creativity. Finally, trusting your instincts and relying on gut feelings can be an effective decision-making approach, even if it's not easily quantifiable or operationalized.

    • The Importance of Intuition in Decision-MakingDecision-making involves more than just data and numbers; intuition and gut feelings also play a significant role. Trusting and acknowledging these instincts can lead to valuable and effective decision-making.

      Decision-making is not solely based on data or numbers. Jason Fried emphasizes that intuition and gut feelings play a significant role in making judgment calls. While data can be a factor, human decision-makers bring their knowledge, experiences, and thousands of other influencing factors to the table. Companies, when hiring executives, prioritize judgment and experience over the ability to analyze spreadsheets. It's important to recognize that decision-making is a complex process that goes beyond quantifiable data. Trusting one's intuition and gut feelings, even if they can't be fully explained, is valuable. Jason Fried encourages giving credit to intuition and the absorbing capacity of our minds, acknowledging the fascinating nature of decision-making. By demonstrating this approach, leaders can create an environment that allows teammates to make decisions based on their instincts too.

    • Trusting instincts and diverse perspectives for better decision-making.Incorporating gut instincts and diverse perspectives in decision-making can lead to improved outcomes and foster creativity and innovation within a team.

      Making decisions based on how something feels rather than relying solely on data or certainty can lead to better outcomes. Jason Fried emphasizes the importance of trusting your instincts and understanding the perspectives of team members when making product-related decisions. He highlights the value of hiring individuals with diverse experiences and preferences, as their unique insights can contribute to a well-rounded perspective. Additionally, Fried discusses the significance of the interview process, where candidates are given a project to complete and their instincts and gut reactions are observed. This approach allows for a deeper understanding of a candidate's thought process and how they generate ideas in a time-constrained situation. Ultimately, this emphasis on gut instincts and the experience-driven decision-making process can foster creativity and innovation within a team.

    • The value of intuition, execution, and creativity in hiringBalance is key when hiring; look for candidates who possess a strong gut instinct, can execute well, and bring creativity to the team.

      When hiring people, it's important to look for individuals who have a good gut instinct and can think on their feet. Having a bunch of ideas is not enough if someone can't execute them well and focus on the right things. On the other hand, someone who can create clear, clever designs and execute them properly, while also having the ability to riff and explore different possibilities, is what makes a valuable addition to a team. Playfulness and creativity are crucial in product development, and a rigid and boring approach won't work in every company. Additionally, trying to make drastic changes too quickly can lead to failure. It's important to find the right balance and give ideas time to develop effectively.

    • The Importance of Momentum and Incremental Changes in BusinessMaking slow and adaptable changes, focusing on individual teams or divisions, is more effective than rushing into drastic changes, especially in software work.

      Making big changes too quickly can often lead to failure. Jason Fried emphasizes the importance of momentum and the difficulty of turning an entire organization's direction overnight. He compares it to the physical world, where the more massive an object, the more energy it takes to change its course. This is why big companies often move slowly. Additionally, Fried notes that most businesses are failures, and the ones that succeed are outliers. Trying to analyze failures and pinpoint the exact reasons can be futile, as there are numerous variables and influences involved, especially in software work. Therefore, it is crucial to avoid rushing into drastic changes and instead focus on implementing smaller, adaptable adjustments that work for individual teams or divisions.

    • Embracing Change and Innovation in BusinessJason Fried emphasizes the importance of embracing change and innovation in business, even if it means winding down previous products and making fundamental shifts in mindset. Designing life and business intentionally, making decisions based on what feels right and brings happiness, is the healthiest and most honest way to run a business.

      Jason Fried and his company, Basecamp, made a significant shift in their approach to business. They originally focused on doing one thing really well, but eventually felt a desire to create and innovate more. They embraced the idea of being makers and decided to develop new products and ideas. This change required them to wind down their previous products and even change the name of the company. Jason Fried emphasizes that he often disagrees with himself on smaller decisions, but this shift in mindset was a major fundamental change. He believes in designing his life and business intentionally, without a long-term plan, and instead focuses on making decisions every six weeks based on what feels right and makes him happy. This approach, he believes, is the healthiest and most honest way to run a business.

    • Planning and Independence: Keys to Success in BusinessStay present, avoid extensive long-term planning, maintain independence, and focus on creating unique and alternative perspectives for success in a crowded market.

      Planning too far into the future can lead to uncertainty and unhappiness. Jason Fried emphasizes that the further out you plan, the less you truly know about the decisions you're making. By the time you reach that point, you may find that you want to do something else or that your initial plans were wrong. The idea of staying closer to the present moment is highlighted as the best approach. Additionally, Fried underscores the importance of maintaining independence in business. The decision to not raise money and remain in control allows for freedom and the ability to do what you truly want. Having expectations is viewed as a matter of pride and caring about the work, rather than fixating on specific outcomes. Ultimately, the focus should be on creating something unique, providing alternative perspectives, and offering a different way forward in an overcrowded market.

    • Shifting from competition to creation: Emphasizing pride and value in your work.Instead of focusing on beating others, prioritize creating something great and valuable, leading to a more positive and fulfilling approach to business.

      Jason Fried emphasizes the importance of being proud of your work and the value it brings instead of focusing on conquering markets or destroying the competition. Many businesses use war metaphors, which Fried finds depressing and counterproductive. Instead, he encourages a perspective that is more additive and alternative, where the goal is to make something great and exist rather than solely focusing on beating others. This shift in mindset changes the way you think about your work, emphasizing pride, excitement, and a spirit of creation. Fried believes that going into business with a mindset of destruction can lead to a negative and dark place. So, focusing on making something great is a more positive and fulfilling approach.

    • Staying Small and Cutting Costs for Business SuccessBy controlling costs, simplifying processes, and embracing the worst-case scenario, businesses can maintain flexibility, efficiency, and confidently navigate challenges.

      Businesses should aim to stay small and keep their costs low for as long as possible. While you can't control market conditions, competition, or the economy, you have full control over your own costs. By minimizing expenses and doing as much of the work yourself, you can maintain flexibility and avoid the financial burden of hiring additional staff too soon. Additionally, it's important to keep things simple and avoid unnecessary complications. Complexity can quickly lead to inefficiencies and difficulties that are hard to undo. Finally, embracing negative visualization and being at peace with the worst-case scenario can help you move forward with confidence and make informed decisions.

    • The Importance of Bootstrapping in Developing Money-Making SkillsBootstrapping forces entrepreneurs to be efficient, profitable, and deliberate in decision-making, leading to sustainability and long-term success. Relying on venture capital funding can result in careless spending and a lack of discipline.

      Bootstrapping, or starting a business without external funding, teaches entrepreneurs the fundamental skill of making money. It forces them to be efficient, profitable, and deliberate in their decision-making. On the other hand, relying on venture capital funding can lead to sloppiness and a lack of discipline, as there is no immediate need to generate profit. With an abundance of money, businesses may become careless in their spending and focus more on growth without considering the sustainability of their actions. Bootstrapping allows entrepreneurs to gain valuable practice in the art of making money, honing their skills and increasing their chances of long-term success. It also requires finding investors who align with this approach and prioritize thoughtful, sustainable growth over quick expansion.

    • Embracing Constraints: A Path to Innovation and SuccessConstraints drive creativity and strategic thinking, leading to success. The story of Peter Rahal starting RXBAR highlights the value of focused action and the current climate emphasizes the importance of financial sustainability.

      Having constraints can be beneficial for businesses. When you have unlimited resources and loads of money, you tend to lack the motivation and drive to innovate and find solutions. Constraints force you to think creatively and strategically in order to overcome challenges and achieve success. This is demonstrated by the story of Peter Rahal, who started RXBAR and was advised by his father to sell 1,000 bars before seeking further investment. The advice cuts through the noise and encourages focused action. Additionally, the current economic climate is highlighting the importance of being scrappy and financially sustainable. It's not about aiming for massive growth or getting more funding, but rather focusing on creating great products, keeping costs in check, and generating profits.

    • Introducing Once: The Solution to Subscription Fatigue in Software-as-a-Service (SaaS) Products.Basecamp's Once product line offers affordable non-SaaS alternatives to address the issue of constantly paying for the same software, providing a new approach to meeting customer needs in the business software industry.

      Subscription fatigue has become a downside of using software-as-a-service (SaaS) products. While SaaS has been the dominant model for the past decade, it involves continuously paying for the same software without receiving frequent updates or new features. Basecamp, a company led by Jason Fried, aims to address this issue by launching a product line called Once. Once offers non-SaaS products that users can download, install, and pay for just once, eliminating recurring fees. By identifying commodities in the market that charge luxury prices, Basecamp can create high-quality, essential alternatives at a fraction of the cost, providing a solution for those seeking affordable software options. This concept challenges the status quo of subscription-based business software and offers a new approach to meeting customer needs.

    • Introducing Once: A Simplified and Customizable Chat Tool by Basecamp.Once allows users to pay once, install on their servers, and customize the tool to their needs, offering 90% of chat tool functionalities in a simpler way.

      Basecamp is relaunching Campfire under the Once brand. With this new tool, users will have the option to pay for it once, install it on their own servers, and run it. It will offer 90% of the features and functionalities of other chat tools, but in a simpler and easier way. The Once products can complement existing tools, providing a backup system or a secure chat for specific groups. Additionally, users will have access to the code, allowing them to modify and customize the tool to their needs. Basecamp aims to create universal software, accessible to people worldwide, with translations available in various languages. This venture into new realms and ideas brings excitement and creativity to the company.

    • An Alternative to SaaS: Software Ownership and Control for Individuals and Small BusinessesThis new software approach allows individuals and small businesses to own and control their software, offering convenience, affordability, and enhanced security for highly sensitive environments.

      This new software approach aims to provide an alternative to the popular Software-as-a-Service (SaaS) model. While SaaS offers convenience and hassle-free maintenance, this new approach allows users to buy the software outright rather than renting it. The intention is to cater to the needs of individuals and small businesses who may prefer ownership and control over their software. The pricing will be set at a point where it becomes a no-brainer for potential buyers to add this software to their toolkit, even if they continue to use other platforms. Additionally, this new approach enables the software to be used in highly secure, air-gapped environments, opening up possibilities for research facilities and organizations with strict security requirements.

    • Embracing Simplicity and Scrappiness for Business SuccessSuccess in business can be achieved by keeping things simple and focusing on profitability, rather than relying on external factors such as raising money or becoming a big company.

      Simplicity and scrappiness are key to success in business. Jason Fried emphasizes the importance of not complicating things unnecessarily and keeping them simple. He believes that progress can be made with just a few people and that significant work can be accomplished in short time frames. Fried suggests that being a profitable business and finding customers who are willing to pay for your product or service are attainable goals. He argues against the idea that raising money and becoming a big company will make things easier, pointing out the expectations and limitations that come with those actions. Overall, Fried advocates for a simplified and scrappy approach to business, highlighting the potential for success without unnecessary complications.

    • Unleashing the Creativity WithinEmbrace your ingenuity and resourcefulness to find solutions, even with limited resources. Let inspiration strike to create unique and functional objects that fulfill your needs.

      Ingenuity and resourcefulness are admirable traits. The book "Home-made: Contemporary Russian Folk Artifacts" showcases how people creatively make things they need when they don't have access to purchasing them. From making a spoon with a hole to blow bubbles or crafting a TV antenna out of forks, these examples demonstrate the power of the human brain to find solutions. This spirit of scrappiness is not only seen in the book but also in jailhouse creations and tools. It highlights the beauty of using limited resources to fulfill needs. This takeaway aligns with Jason Fried's appreciation for handmade objects and his admiration for those who can think outside the box.

    • The Value of Staying Connected to our Work and Trusting Intuition.Stay connected to the core of our work, avoid unnecessary abstractions, and trust our instincts in decision-making for better choices.

      Staying connected to the work we do, whether in business or in life, has a lot of value. Jason Fried compares modern cars with automatic transmissions to large businesses that have multiple layers of abstractions and disconnect. He finds beauty in the directness and simplicity of driving an old, manual car that is harder, noisier, and bumpier. This parallel reminds us of the importance of staying connected to the core of our work and avoiding unnecessary abstractions. Additionally, Fried emphasizes the need to worry less and embrace gut instincts and intuition in decision-making. Celebrating intuition in business is often overlooked, but these innate senses can guide us to make better choices. So, the big takeaway is to prioritize staying connected to our work and trusting our instincts.

    • Trusting our instincts and embracing our lack of expertise can lead to innovation and fresh perspectives.Sometimes, not knowing how others do things and relying on our intuition can be an advantage, inspiring confidence and allowing us to approach problems differently. Additionally, supporting others through word of mouth can greatly contribute to their growth.

      Trusting our gut and following our instincts can lead to great things, even if we don't have all the knowledge or experience. Jason Fried's conversation with Charlie Munger revealed that innovation often happens when we don't know how others do things and rely on our intuition instead. When we lack evidence, examples, or a set list of instructions, we're forced to rely on our feelings and creativity. This insight gave Fried confidence and hope, inspiring him to continue following his gut. It's a reminder that sometimes, our lack of expertise can actually be an advantage, allowing us to approach problems from a fresh perspective. Moreover, if we believe in what someone is doing, sharing their work through word of mouth can significantly support their growth.

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

    Dylan Field live at Config: Intuition, simplicity, and the future of design

    Dylan Field live at Config: Intuition, simplicity, and the future of design

    Dylan Field is the co-founder and CEO of Figma, the collaborative design platform that has revolutionized how product teams work. In my first-ever live podcast, recorded at Figma Config, Dylan and I dig into:

    • How intuition and product taste drive Dylan’s decision-making

    • The challenge of keeping things simple

    • Dylan’s thoughts on the future of product management

    • Lessons from Figma’s early days

    • How Figma built their initial user base

    • Dylan’s journey from intern to CEO of a 1,000+-person company

    • The future of design tools and AI

    Brought to you by:

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

    Anvil—The fastest way to build software for documents

    User Testing—Human understanding. Human experiences.

    Find the transcript at: https://www.lennysnewsletter.com/p/dylan-field-live-at-config

    Where to find Dylan Field:

    • X: https://x.com/zoink?lang=en

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

    Where to find Lenny:

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

    • X: https://twitter.com/lennysan

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

    In this episode, we cover:

    (00:00) Introduction

    (01:11) Welcoming Dylan Field

    (02:36) Highlights and surprises from Config

    (06:58) The philosophy of design

    (08:01) Raccoon feet and muffin hands

    (09:57) Building and refining intuition and product taste

    (12:50) How to influence leadership

    (16:14) The role of product managers

    (21:12) The future of product management

    (22:20) The importance of simplicity in design

    (26:10) The long road to Figma’s launch

    (27:44) Advice for aspiring entrepreneurs

    (29:07) Knowing when it’s time to ship

    (30:39) Early user acquisition strategies

    (35:50) Spotting trends and future innovations

    (39:20) Reflections on leadership and growth

    (43:16) Lightning round

    Referenced:

    • Mihika Kapoor on LinkedIn: https://www.linkedin.com/in/mihikakapoor/

    • Rick Rubin on the Creative Act—60 Minutes: https://www.youtube.com/watch?v=sE1teB5bN-w

    • Figma pages: https://help.figma.com/hc/en-us/articles/360038511293-Create-and-manage-pages

    • Leading through uncertainty: A design-led company—Brian Chesky (Config 2023): https://www.youtube.com/watch?v=Dkfijg7s76o

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

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

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

    • 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

    • Nadia Singer on LinkedIn: https://www.linkedin.com/in/nadiasinger/

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

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

    • Tim Van Damme on LinkedIn: https://www.linkedin.com/in/tim-van-damme-maxvoltar/

    • Coda: https://coda.io/

    • Shishir Mehrotra on LinkedIn: https://www.linkedin.com/in/shishirmehrotra/

    • Websim: https://websim.ai/

    • eToys.com commercial (from Dylan’s childhood acting career): https://www.youtube.com/watch?v=k3Y92aCmmbU

    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 social radar: Y Combinator’s secret weapon | Jessica Livingston (co-founder of Y Combinator, author, podcast host)

    The social radar: Y Combinator’s secret weapon | Jessica Livingston (co-founder of Y Combinator, author, podcast host)

    Jessica Livingston is a co-founder of Y Combinator, the first and most successful startup accelerator. Y Combinator has funded over 5,000 companies, 200 of which are now unicorns, including Airbnb, Dropbox, DoorDash, Stripe, Coinbase, and Reddit. Jessica played a crucial role in YC’s early success, when she was nicknamed the “social radar” because of her uncanny ability to quickly evaluate people—an essential skill when investing in early-stage startups. She’s also the host of the popular podcast The Social Radars, where she interviews billion-dollar-startup founders, and the author of the acclaimed book Founders at Work, which captures the origin stories of some of today’s most interesting companies. In our conversation, we discuss:

    • How Jessica gained the affectionate title of the “social radar”

    • Why defensive founders are a red flag

    • How to develop your social radar

    • What she looks for in founders during YC interviews

    • How YC’s early inexperience in angel investing led to the batch model

    • Her favorite stories from interviews with Airbnb, Rippling, and more

    • Lessons learned from hosting her own podcast

    • Much more

    Brought to you by:

    Enterpret—Transform customer feedback into product growth

    Anvil—The fastest way to build software for documents

    Vanta—Automate compliance. Simplify security

    Find the transcript at: https://www.lennysnewsletter.com/p/the-social-radar-jessica-livingston

    Where to find Jessica Livingston:

    • X: https://x.com/jesslivingston

    • LinkedIn: https://www.linkedin.com/in/jessicalivingston1/

    • Podcast: https://www.thesocialradars.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) Jessica’s background

    (02:42) Thoughts on being under-recognized

    (07:52) Jessica’s superpower: the social radar

    (15:11) Evaluating founders: key traits and red flags

    (21:00) The Airbnb story: a lesson in hustle and determination

    (25:57) A YC success story

    (28:26) The importance of earnestness

    (32:45) Confidence vs. defensiveness

    (34:43) Commitment and co-founder disputes

    (37:46) Relentless resourcefulness

    (40:00) Jessica’s social radar: origins and insights

    (43:24) Honing her social radar skills

    (45:44) Conviction and scams: a Y Combinator story

    (46:50) The interview process: challenges and insights

    (48:20) Operationalizing founder evaluation

    (49:38) Advice for building social radar skills

    (52:08) The “Reading the Mind in the Eyes” quiz

    (55:19) Jessica’s podcast: The Social Radars

    (01:00:34) Lessons from podcasting and interviewing

    (01:09:58) Lightning round

    Referenced:

    • Paul Graham’s post about Jessica: https://paulgraham.com/jessica.html

    • Paul Graham on X: https://x.com/paulg

    • Robert Tappan Morris: https://en.wikipedia.org/wiki/Robert_Tappan_Morris

    • Trevor Blackwell on X: https://x.com/tlbtlbtlb

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

    • “The Founders” examines the rise and legend of PayPal: https://www.economist.com/culture/2022/02/19/the-founders-examines-the-rise-and-legend-of-paypal

    • Patrick Collison on X: https://x.com/patrickc

    • John Collison on X: https://x.com/collision

    • Brian Chesky on LinkedIn: https://www.linkedin.com/in/brianchesky/

    • Nate Blecharczyk on LinkedIn: https://www.linkedin.com/in/blecharczyk/

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

    • 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/

    • Parker Conrad on LinkedIn: https://www.linkedin.com/in/parkerconrad/

    • Zenefits: https://connect.trinet.com/hr-platform

    • Goat: https://www.goat.com/

    • Eddy Lu on LinkedIn: https://www.linkedin.com/in/eddylu/

    • Drew Houston on LinkedIn: https://www.linkedin.com/in/drewhouston/

    • Arash Ferdowsi on LinkedIn: https://www.linkedin.com/in/arashferdowsi/

    • Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director): https://www.lennysnewsletter.com/p/lessons-from-1000-yc-startups

    •Bitcoin launderer pleads guilty, admits to massive Bitfinex hack: https://www.cnbc.com/2023/08/03/new-york-man-admits-being-original-bitfinex-hacker-during-guilty-plea-in-dc-to-bitcoin-money-laundering.html

    • Paul Graham’s tweet with the facial recognition test: https://x.com/paulg/status/1782875262855663691

    • SmartLess podcast: https://www.smartless.com

    • Jason Bateman on X: https://x.com/batemanjason

    • Will Arnett on X: https://x.com/arnettwill

    • Sean Hayes on X: https://x.com/seanhayes

    • The Social Radars with Tony Xu, Co-Founder & CEO of DoorDash: https://www.ycombinator.com/library/Ja-tony-xu-co-founder-ceo-of-doordash

    • The Social Radars with Brian Chesky: https://www.ycombinator.com/library/JW-brian-chesky-co-founder-ceo-of-airbnb

    • The Social Radars with Patrick and John Collison: https://www.ycombinator.com/library/Kx-patrick-john-collison-co-founders-of-stripe

    • The Social Radars with Brian Armstrong: https://www.ycombinator.com/library/K3-brian-armstrong-co-founder-and-ceo-of-coinbase

    • The Social Radars with Emmett Shear: https://www.ycombinator.com/library/KM-emmett-shear-co-founder-of-twitch

    • The Social Radars with Paul Graham: https://www.ycombinator.com/library/JV-paul-graham-co-founder-of-y-combinator-and-viaweb

    • The Social Radars with Adora Cheung: https://www.ycombinator.com/library/L0-adora-cheung-co-founder-of-homejoy-instalab

    Founders at Work: Stories of Startups’ Early Days: https://www.amazon.com/Founders-Work-Stories-Startups-Early/dp/1430210788

    • Startup School: https://www.startupschool.org/

    • The Social Radars with Parker Conrad: https://www.ycombinator.com/library/Ky-parker-conrad-founder-of-zenefits-rippling

    • Rippling: https://www.rippling.com/

    Carry on, Jeeves: https://www.amazon.com/Carry-Jeeves-Dover-Thrift-Editions/dp/0486848957

    Very Good, Jeeves: https://www.amazon.com/Very-Good-Jeeves-Wooster-Book-ebook/dp/B0051GST06

    Right Ho, Jeeves: https://www.amazon.com/Right-Ho-Jeeves-P-Wodehouse-ebook/dp/B083FFDNHN/

    Life: https://www.amazon.com/Life-Keith-Richards-ebook/dp/B003UBTX72/

    My Name Is Barbra: https://www.amazon.com/My-Name-Barbra-Streisand/dp/0525429522

    Clarkson’s Farm on Prime: https://www.amazon.com/Clarksons-Farm-Season-1/dp/B095RHJ52R

    Schitt’s Creek on Hulu: https://www.hulu.com/series/schitts-creek-a2e7a946-9652-48a8-884b-3ea7ea4de273

    Yellowstone on Peacock: https://www.peacocktv.com/stream-tv/yellowstone

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

    • Justin Kan on LinkedIn: https://www.linkedin.com/in/justinkan/

    • Alexis Ohanian on X: https://x.com/alexisohanian

    • Steve Huffman on LinkedIn: https://www.linkedin.com/in/shuffman56/

    • Breaking News: Condé Nast/Wired Acquires Reddit: https://techcrunch.com/2006/10/31/breaking-news-conde-nastwired-acquires-reddit/

    • Charles River Venture: https://www.crv.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

    Making an impact through authenticity and curiosity | Ami Vora (CPO at Faire, ex-WhatsApp, FB, IG)

    Making an impact through authenticity and curiosity | Ami Vora (CPO at Faire, ex-WhatsApp, FB, IG)

    Ami Vora is the Chief Product Officer of Faire, which connects independent retailers and brands around the world. Before Faire, Ami spent over 15 years at Meta, including as VP of Product and Design for WhatsApp (2B+ users), VP of Product for Facebook’s ads system (now $130B of annual revenue), and director at Instagram. She began her career working on developer tools at Microsoft. In our conversation, we discuss:

    • Why execution eats strategy for breakfast

    • Using metaphor to rally teams around one shared goal

    • How to build cross-functional relationships

    • “Dinosaur brain,” “Toddler soccer,” and the “hill climbing” metaphors

    • A tactic for handling disagreement

    • Tips for working well with product-minded founders as a product leader

    • The story of Ami’s incredible 15-year journey from temp to VP at Meta

    • Much more

    Brought to you by:

    Sidebar—Accelerate your career by surrounding yourself with extraordinary peers.

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    User Testing—Human understanding. Human experiences.

    Find the transcript at: https://www.lennysnewsletter.com/p/authenticity-and-curiosity-ami-vora

    Where to find Ami Vora:

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

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

    Where to find Lenny:

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

    • X: https://twitter.com/lennysan

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

    In this episode, we cover:

    (00:00) Ami’s background

    (02:00) The myth of perfection in success

    (07:55) Emotionally connecting with the job

    (09:55) Embracing curiosity in moments of challenge

    (13:16) Thinking in feedback loops

    (17:17) The “dinosaur brain” metaphor in product reviews

    (20:20) Strategies for conducting effective product reviews

    (26:33) Using metaphors and imagery to communicate your vision

    (29:35) The power of having a shared narrative

    (31:55) WhatsApp: an example of metaphor in action

    (34:44) Emulating people that inspire you

    (36:19) WhatsApp video calling

    (37:35) Why execution is greater than strategy

    (41:36) Time allotment for strategy vs. execution

    (45:10) How to become a better strategic thinker

    (47:59) The intricacies of implementing feedback

    (51:53) Being a female leader in tech

    (55:13) Advice for young women in tech

    (56:07) Setting goals and aligning incentives

    (01:01:40) Acknowledging hard truths

    (01:05:46) Lessons from transitioning to Faire

    (01:08:40) The importance of a good CPO/CEO relationship

    (01:11:17) Vetting heads of product and maintaining customer focus

    (01:12:40) How Ami went from intern to leading major products at Meta

    (01:14:53) The one thing you should do to be successful in product

    (01:17:25) Lightning round

    Referenced:

    • Faire: https://www.faire.com/

    • Making Meta | Andrew “Boz” Bosworth (CTO): https://www.lennysnewsletter.com/p/making-meta-andrew-boz-bosworth-cto

    •  Community Wisdom: AMA with Dan Hockenmaier + Facilitating a roadmap session, structuring product teams, navigating an acquisition, companies not needing PMs anymore, and much more: https://www.lennysnewsletter.com/p/making-meta-andrew-boz-bosworth-cto

    • Developing a growth model + marketplace growth strategy | Dan Hockenmaier (Faire, Thumbtack, Reforge): https://www.lennysnewsletter.com/p/developing-a-growth-model-marketplace

    • Dan Hockenmaier’s website: https://www.danhock.com/

    • On Reviews: https://boz.com/articles/reviews

    • Finding a global optimum always feels like a hill climb: https://www.linkedin.com/posts/amvora_finding-a-global-optimum-always-feels-like-activity-7074776143882588161-jhyy/

    • Dolores Park: https://sfrecpark.org/892/Mission-Dolores-Park

    • Rob Goldman on LinkedIn: https://www.linkedin.com/in/robgoldman/

    • Execution eats strategy for breakfast, but execution without strategy leads to burnout: https://rationalpm.substack.com/p/execution-eats-strategy-for-breakfast

    • The goal of a “strategy” is to change our own team’s behavior: https://amivora.substack.com/p/the-goal-of-a-strategy-is-to-change

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

    • Path to Power course outline: https://jeffreypfeffer.com/wp-content/uploads/2019/10/Pfeffer-OB377-Course-Outline-2018.pdf

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

    • Max Rhodes on LinkedIn: https://www.linkedin.com/in/max-rhodes/

    • Coupa Coffee: https://www.coupacafe.com/

    • Brandee Barker on LinkedIn: https://www.linkedin.com/in/brandeedbarker/

    Year of Yes: How to Dance It Out, Stand In the Sun and Be Your Own Person: https://www.amazon.com/Year-Yes-Dance-Stand-Person/dp/1476777128 

    • How to tell better stories | Matthew Dicks (Storyworthy): https://www.lennyspodcast.com/how-to-tell-better-stories-matthew-dicks-storyworthy/

    • A life of yes: Matthew Dicks at TEDxSomerville: https://www.youtube.com/watch?v=F3TaQFcaMk4

    The Office on Peacock: https://www.peacocktv.com/stream-tv/the-office

    30 Rock on Peacock: https://www.peacocktv.com/watch-online/tv/30-rock/6240863759978157112

    • Dall-E-2: https://openai.com/index/dall-e-2/

    • ChatGPT: https://chatgpt.com

    • Fellow kettles: https://fellowproducts.com/products/stagg-ekg-electric-pour-over-kettle

    • TikTok’s “Roman Empire” Meme, Explained: https://www.forbes.com/sites/danidiplacido/2023/09/21/tiktoks-roman-empire-meme-explained/

    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

    Hard-won lessons building 0 to 1 inside Atlassian | Tanguy Crusson (Head of Jira Product Discovery)

    Hard-won lessons building 0 to 1 inside Atlassian | Tanguy Crusson (Head of Jira Product Discovery)

    Tanguy Crusson is the product lead for Jira Product Discovery at Atlassian. In his more than 10 years at the company, he has been instrumental in taking several new products from zero to one, including HipChat, Statuspage, and Jira Product Discovery. In this episode, we dive deep into the struggles of innovating and building new products inside a large company. Tanguy shares candid stories about what worked, what didn’t, and his many hard-won lessons learned about how to successfully build 0 to 1. We cover:

    • Why large companies with so many advantages still fail at creating new products

    • Lessons learned from building HipChat

    • How to avoid common pitfalls like competitive myopia and premature scaling

    • Lessons learned from the acquisition and integration of Statuspage

    • Insights from the success of Jira Product Discovery

    • Tactics for protecting your “ugly babies”

    • The power of “lighthouse users”

    • The importance of having a “why now”

    • Much more

    Brought to you by:

    Vanta—Automate compliance. Simplify security

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

    Coda—The all-in-one collaborative workspace

    Find the transcript at: https://www.lennysnewsletter.com/p/building-0-to-1-inside-atlassian-tanguy-crusson

    Where to find Tanguy Crusson:

    • X: https://x.com/tanguycrusson

    • LinkedIn: https://www.linkedin.com/in/tanguy-crusson-99832a

    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) Tanguy’s background

    (02:30) Tanguy’s journey at Atlassian

    (07:03) The challenges of innovating in large companies

    (10:42) Atlassian's high bar for excellence 

    (12:58) The HipChat story: successes, failures, and lessons learned

    (20:47) Lessons learned from building HipChat

    (33:49) Statuspage: a journey of perseverance

    (39:48) Acquisition challenges and lessons

    (47:22) Strategic decisions: build, buy, or partner?

    (48:17) Learning to articulate "why now"

    (54:08) A quick summary of lessons in this episode

    (55:40) The success and pain of launching Jira Product Discovery 

    (58:10) Incubating new products: the Point A program

    (01:00:13) Failure is the most likely outcome

    (01:04:15) Atlassian's four-phase approach to launching new products

    (01:09:20) Breaking rules without breaking trust

    (01:16:16) Early success and team autonomy

    (01:17:22) Innovating without disrupting existing customers

    (01:23:17) The Lighthouse Users program

    (01:30:00) Protecting and nurturing new ideas

    (01:36:14) Balancing innovation with personal well-being

    (01:38:17) A reminder to look after yourself

    (01:42:06) Lightning round

    Referenced:

    • Atlassian: https://www.atlassian.com/

    • HipChat: https://community.atlassian.com/t5/Hipchat/ct-p/hipchat

    • Stride: https://community.atlassian.com/t5/Stride/ct-p/stride

    • Statuspage: https://www.atlassian.com/software/statuspage

    • Opsgenie: https://www.atlassian.com/software/opsgenie

    • Jira Product Discovery: https://www.atlassian.com/software/jira/product-discovery

    • HipChat billboard: https://x.com/HubSpot/status/654696998126272512

    • Announcing our new partnership with Slack: https://www.atlassian.com/blog/announcements/new-atlassian-slack-partnership

    • Slack shows it’s worried about Microsoft Teams with a full-page newspaper ad: https://www.theverge.com/2016/11/2/13497766/slack-microsoft-teams-new-york-times-ad

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

    • Jira: https://www.atlassian.com/software/jira

    • Confluence: https://www.atlassian.com/software/confluence

    • PagerDuty: https://www.pagerduty.com/

    • New Relic: https://newrelic.com/

    • BigPanda: https://www.bigpanda.io/

    • Transparent Uptime: http://www.transparentuptime.com/

    • 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

    • Figma: https://www.figma.com/

    • Lessons from Atlassian: Launching new products, getting buy-in, and staying ahead of the competition | Megan Cook (head of product, Jira): https://www.lennysnewsletter.com/p/lessons-from-atlassian-launching

    • Noah Weiss on LinkedIn: https://www.linkedin.com/in/noahw/

    • Tanguy’s LinkedIn post about “lighthouse users”: https://www.linkedin.com/posts/tanguy-crusson-99832a_lighthouse-users-one-of-the-pm-techniques-activity-7176654510801502210-hWNi/

    • Pixar Chief: Protect Your ‘Ugly Babies’ (Your Unsightly Ideas): https://www.forbes.com/sites/andyboynton/2014/03/17/pixar-chief-protect-your-ugly-babies-your-unsightly-ideas/

    • Atlas: https://www.atlassian.com/software/atlas

    • Point A: https://www.atlassian.com/point-a

    • Scott Farquhar on LinkedIn: https://www.linkedin.com/in/scottfarquhar

    Who: A Method for Hiring: https://www.amazon.com/Who-Method-Hiring-HC-2008/dp/B004C79SRS/

    Hakim’s Odyssey: Book 1: From Syria to Turkey: https://www.amazon.com/Hakims-Odyssey-Book-Syria-Turkey/dp/1637790007

    Living with the Earth, Volume 1: Permaculture, Ecoculture: Inspired by Nature: https://www.amazon.com/Living-Earth-Gardeners-Permaculture-Ecoculture/dp/1856232603/

    • INRIA: https://en.wikipedia.org/wiki/French_Institute_for_Research_in_Computer_Science_and_Automation

    • How a Hydrofoil Works: https://web.mit.edu/2.972/www/reports/hydrofoil/hydrofoil.html

    • What Is Kitefoil or Foilboarding?: https://www.whenitswindy.com/wp/?page_id=534

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

    • Tanguy’s freediving stats: https://www.aidainternational.org/Athletes/Profile-00000000-0000-0000-0000-000000000a45

    • Perplexity: https://www.perplexity.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

    The paths to power: How to grow your influence and advance your career | Jeffrey Pfeffer (author of 7 Rules of Power, professor at Stanford GSB)

    The paths to power: How to grow your influence and advance your career | Jeffrey Pfeffer (author of 7 Rules of Power, professor at Stanford GSB)

    Jeffrey Pfeffer teaches the single most popular (and somewhat controversial) class at Stanford’s Graduate School of Business: The Paths to Power. He’s also the author of 16 books, including 7 Rules of Power: Surprising—But True—Advice on How to Get Things Done and Advance Your Career. He has taught at Harvard, the London Business School, and IESE and has written for publications like Fortune and the Washington Post. Recognized by the Academy of Management and listed in the Thinkers50 Hall of Fame, Jeffrey also serves on several corporate and nonprofit boards, bringing his expertise to global audiences through seminars and executive education. In our conversation, we discuss:

    • Jeffrey’s seven rules of power

    • How individuals can acquire and use power in business

    • Networking, and how to do it effectively

    • How to build a non-cringe personal brand

    • How to increase your influence to amplify your impact

    • Examples and stories of people building power

    • Tradeoffs and challenges that come with power

    Brought to you by:

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    Find the transcript at: https://www.lennysnewsletter.com/p/the-paths-to-power-jeffrey-pfeffer

    Where to find Jeffrey Pfeffer:

    • X: https://x.com/JeffreyPfeffer

    • LinkedIn: https://www.linkedin.com/in/jeffrey-pfeffer-57a01b6/

    • Website: https://jeffreypfeffer.com/

    • Podcast: https://jeffreypfeffer.com/pfeffer-on-power/

    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) Jeffrey’s background 

    (02:54) Understanding discomfort with power

    (04:56) Power skills for underrepresented groups

    (07:51) The popularity and challenges of Jeffrey’s class at Stanford

    (12:21) The seven rules of power

    (13:03) Success stories from his course

    (15:43) Building a personal brand

    (21:11) Getting out of your own way

    (26:04) Breaking the rules to gain power

    (30:34) Networking relentlessly

    (40:10) Why Jeffrey says to “pursue weak ties”

    (42:00) Using your power to build more power

    (44:34) The importance of appearance and body language

    (47:15) Mastering the art of presentation

    (55:12) Examples of homework assignments that Jeffrey gives students

    (59:11) People will forget how you acquired power

    (01:03:58) More good people need to have power

    (01:10:49) The price of power and autonomy

    (01:17:13) A homework assignment for you

    Referenced:

    • Gerald Ferris on LinkedIn: https://www.linkedin.com/in/gerald-r-ferris-5816b1b5/

    • Political Skill at Work: https://tarjomefa.com/wp-content/uploads/2015/10/4173-engilish.pdf

    • Laura Esserman, MD: https://cancer.ucsf.edu/people/esserman.laura

    • Taylor Swift’s website: https://www.taylorswift.com/

    • Matthew 7: https://www.biblegateway.com/passage/?search=Matthew%207&version=NIV

    • Mother Teresa quote: https://www.goodreads.com/quotes/2887-if-you-judge-people-you-have-no-time-to-love

    • Paths to Power course description: https://jeffreypfeffer.com/wp-content/uploads/2019/10/Pfeffer-OB377-Course-Outline-2018.pdf

    7 Rules of Power: https://jeffreypfeffer.com/books/7-rules-of-power/

    The Knowing-Doing Gap: https://jeffreypfeffer.com/books/the-knowing-doing-gap/

    • Derek Kan on LinkedIn: https://www.linkedin.com/in/derekkan/

    • Mitt Romney on X: https://x.com/mittromney

    • Elaine Chao’s website: https://www.elainechao.com/

    • Tony Hsieh: https://en.wikipedia.org/wiki/Tony_Hsieh

    • Zappos: https://www.zappos.com/

    • How I Did It: Zappos’s CEO on Going to Extremes for Customers: https://hbr.org/2010/07/how-i-did-it-zapposs-ceo-on-going-to-extremes-for-customers

    • McKinsey & Company: https://www.mckinsey.com/

    • Bain & Company: https://www.bain.com/

    • BCG: https://www.bcg.com/

    • Keith Ferrazzi’s website: https://www.keithferrazzi.com/

    • Deloitte: https://www2.deloitte.com/

    • Tristan Walker: https://www.linkedin.com/in/tristanwalker/

    • Foursquare: https://foursquare.com/

    • Laura Chau on LinkedIn: https://www.linkedin.com/in/laura-chau/

    • Canaan Partners: https://www.canaan.com/

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

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

    • Greylock: https://greylock.com/

    The Women Who Venture (WoVen) Podcast: https://www.canaan.com/woven/podcasts

    • Imposter syndrome: https://www.psychologytoday.com/us/basics/imposter-syndrome

    • Gary Loveman and Harrah’s Entertainment: https://www.gsb.stanford.edu/faculty-research/case-studies/gary-loveman-harrahs-entertainment

    • “If you need help, just ask”: Underestimating compliance with direct requests for help: https://www.gsb.stanford.edu/faculty-research/publications/if-you-need-help-just-ask-underestimating-compliance-direct-requests

    • Life story of Kathleen Frances Fowler: https://www.forevermissed.com/kathleenfowler/lifestory

    • Jason Calacanis on LinkedIn: https://www.linkedin.com/in/jasoncalacanis/

    • Jason Calacanis: A Case Study in Creating Resources: https://www.gsb.stanford.edu/faculty-research/case-studies/jason-calacanis-case-study-creating-resources

    You’re Invited: The Art and Science of Connection, Trust, and Belonging: https://www.amazon.com/Youre-Invited-Science-Cultivating-Influence/dp/0063030977

    • View from the Top: https://www.gsb.stanford.edu/experience/learning/guest-speakers/view-top

    • Omid Kordestani on LinkedIn: https://www.linkedin.com/in/omid-kordestani-46515151/

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

    •  Esther Wojcicki on LinkedIn:  https://www.linkedin.com/in/estherwojcicki/

    • Leanne Williams: https://med.stanford.edu/profiles/leanne-williams

    Precision Psychiatry: Using Neuroscience Insights to Inform Personally Tailored, Measurement-Based Care: https://www.amazon.com/Precision-Psychiatry-Neuroscience-Personally-Measurement-Based/dp/1615371583

    • Mark Granovetter on LinkedIn: https://www.linkedin.com/in/mark-granovetter-8161704/

    • The Strength of Weak Ties: https://snap.stanford.edu/class/cs224w-readings/granovetter73weakties.pdf

    Getting a Jobhttps://www.amazon.com/Getting-Job-Study-Contacts-Careers/dp/0226305813

    Acting with Power: https://www.amazon.com/Acting-Power-More-Powerful-Believe/dp/110190397X

    • Articles by Herminia Ibarra: https://herminiaibarra.com/articles/

    Kingdom of the Planet of the Ape: https://www.imdb.com/title/tt11389872/

    • Jim Collins’s website: https://www.jimcollins.com/

    • Dana Carney on LinkedIn: https://www.linkedin.com/in/danarosecarney/

    • Baba Shiv: https://www.gsb.stanford.edu/faculty-research/faculty/baba-shiv

    • Tony Hayward: https://en.wikipedia.org/wiki/Tony_Hayward

    • Lloyd Blankfein: https://en.wikipedia.org/wiki/Lloyd_Blankfein

    • Regis McKenna: https://en.wikipedia.org/wiki/Regis_McKenna

    • Jack Valenti: https://en.wikipedia.org/wiki/Jack_Valenti

    • Salman Rushdie quote: https://www.pinterest.com/pin/434175220328596286/

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

    • Carole Robin’s 15% rule: https://pen-name.notion.site/Carole-Robin-on-Lenny-s-Podcast-dc7159208e4242428f4b11ebc92285eb

    • Karlie Kloss on Instagram: https://www.instagram.com/karliekloss

    • Lindsey Graham’s website: https://www.lindseygraham.com/

    • Was Microsoft’s Empire Built on Stolen Code? We May Never Know: https://www.wired.com/2012/08/ms-dos-examined-for-thef/

    • Who’s who of Jeffrey Epstein’s powerful friends, associates and possible co-conspirators: https://www.cnn.com/2019/08/12/us/jeffrey-epstein-associates-possible-accomplices/index.html

    • Why Did Martha Stewart Go to Prison? A Look Back at Her 2004 Fraud Case: https://people.com/martha-stewart-fraud-case-prison-sentence-look-back-8550277

    • Dianne Feinstein: https://www.congress.gov/member/dianne-feinstein/F000062

    • Richard Blum: https://en.wikipedia.org/wiki/Richard_C._Blum

    • Athena Care Network: https://www.athenacarenetwork.org

    • James G. March: https://en.wikipedia.org/wiki/James_G._March

    • Satya Nadella on LinkedIn: https://www.linkedin.com/in/satyanadella/

    • Trump Organization fined $1.6 million for tax fraud: https://apnews.com/article/politics-legal-proceedings-new-york-city-donald-trump-manhattan-e2f1d01525dafb64be8738c8b4f32085

    • Rudy Giuliani: https://en.wikipedia.org/wiki/Rudy_Giuliani

    • Harvard president resigns amid claims of plagiarism and antisemitism backlash: https://www.theguardian.com/education/2024/jan/02/harvard-president-claudine-gay-resigns

    • Stanford president resigns after fallout from falsified data in his research: https://www.npr.org/2023/07/19/1188828810/stanford-university-president-resigns

    • Rudy Crew: https://en.wikipedia.org/wiki/Rudy_Crew

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

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

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

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

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

    • Why firing is more important than hiring

    • How Waze iterated to achieve product-market fit

    • Tactics for telling a compelling story when fundraising

    • Much more

    Brought to you by:

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

    Where to find Uri Levine:

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

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

    • Website: https://urilevine.com/

    Where to find Lenny:

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

    • X: https://twitter.com/lennysan

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

    In this episode, we cover:

    (00:00) Uri’s background

    (02:50) Falling in love with the problem

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

    (10:54) The importance of passion

    (12:06) A pivot example

    (14:01) Where to find startup ideas

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

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

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

    (39:53) Fundraising tips

    (48:02) How to make your presentations stronger

    (50:32) A wild fundraising story

    (53:46) Firing and hiring

    (59:50) The 30-day test

    (01:04:12) Understanding users

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

    (01:15:36) Lightning round

    Referenced:

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

    • Waze: https://www.waze.com/

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

    • Pontera: https://pontera.com/

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

    Lenny may be an investor in the companies discussed.



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

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

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

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

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

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

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

    • Insights into Canva’s SEO growth strategy

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

    • Stories from the early days

    Brought to you by:

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

    Where to find Cameron Adams:

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

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

    • Website: https://themaninblue.com/

    Where to find Lenny:

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

    • X: https://twitter.com/lennysan

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

    In this episode, we cover:

    (00:00) Cameron’s background

    (02:00) Reflecting on the success of Canva

    (04:50) Reflecting on hard times

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

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

    (13:56) What makes Canva unique

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

    (21:44) Why Canva has no managers

    (24:29) Product management at Canva

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

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

    (33:49) Advice for building an MVP

    (41:23) Canva’s onboarding transformation

    (44:25) Canva’s SEO strategy

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

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

    (01:01:50) Where to find Cameron

    Referenced:

    • Canva: https://www.canva.com/

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

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

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

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

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

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

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

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

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

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

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

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

    Lenny may be an investor in the companies discussed.



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

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

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

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

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

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

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

    • The JOLT method for overcoming indecision

    • Key lessons from The Challenger Sale

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

    Brought to you by:

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

    Where to find Matt Dixon:

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

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

    Where to find Lenny:

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

    • X: https://twitter.com/lennysan

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

    In this episode, we cover:

    (00:00) Matt’s background

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

    (06:08) Insights from The JOLT Effect

    (10:15) FOMO vs. FOMU

    (18:18) An example of selling software

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

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

    (34:49) Step 2: Offer a recommendation

    (38:36) Step 3: Limit the exploration

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

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

    (47:27) Insights from The Challenger Sale

    (49:07) An example of a challenger sale

    (55:23) Where to find Matt

    Referenced:

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

    Lenny may be an investor in the companies discussed.



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

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

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

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

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

    • The importance of “understand work”

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

    • Advice for coaching product managers

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

    • Much more

    Brought to you by:

    Uizard—AI-powered prototyping for visionary product leaders

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

    Vanta—Automate compliance. Simplify security.

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

    Where to find Bangaly Kaba:

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

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

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

    Where to find Lenny:

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

    • X: https://twitter.com/lennysan

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

    In this episode, we cover:

    (00:00) Bangaly’s background

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

    (08:39) The impact factor

    (10:53) Evaluating the environment

    (15:53) The manager component

    (18:27) The skills part of the equation

    (23:49) Advice on finding a mentor

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

    (31:17) Operationalizing understand work

    (37:55) Balancing understand work

    (41:25) Managing complex change

    (45:26) Effective management of product managers

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

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

    (01:03:14) Understanding adjacent users

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

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

    (01:25:37) Lessons from Facebook

    (01:29:15) Failure corner

    (01:31:58) Lightning round

    Referenced:

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

    • Stripe: https://stripe.com/

    • Chief: https://chief.com/

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

    Lenny may be an investor in the companies discussed.



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

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

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

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

    • Why asking for what you want is so impactful

    • Three steps to effectively ask for what you want

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

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

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

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

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

    • Why discipline is overrated

    Brought to you by:

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

    Where to find Kenneth Berger:

    • X: https://twitter.com/kberger

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

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

    • Website: https://kberger.com/

    Where to find Lenny:

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

    • X: https://twitter.com/lennysan

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

    In this episode, we cover:

    (00:00) Kenneth’s background

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

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

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

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

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

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

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

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

    (24:07) Doing an integrity check

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

    (30:45) Understanding your influence

    (34:48) Using complaints as inspiration

    (36:24) Internal family systems

    (38:00) Giving feedback

    (41:24) Step 3: Accept the response

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

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

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

    (01:05:52) Lightning round

    Referenced:

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

    Lenny may be an investor in the companies discussed.



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

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