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    88. Asking the uncomfortable questions, w/ Michael Seibel, Y Combinator

    enJune 29, 2021
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    Podcast Summary

    • The Importance of Timing Your Decisions in StartupsBefore making a decision, ask yourself if it needs to be made immediately or if waiting can provide a better, multivariable solution. Asking uncomfortable questions and seeking advice from the right people can lead to success.

      Founders should ask themselves if a decision needs to be made right now or if they can wait. As Michael Seibel, managing director of Y Combinator, explains, many problems are multivariable and don't require immediate decisions. In fact, asking the uncomfortable, self-searching questions that may feel contrary to the norms of startup life is essential for success. Reid Hoffman, co-founder of LinkedIn, emphasizes the importance of asking the right questions to the right people and acting on the answer, even if it seems irrational. This lesson can be learned from a classic samurai adventure Shōgun, where the smarter of the two main characters always finds a way to introduce a third, often better option by just waiting.

    • The Power of Asking Difficult Questions in EntrepreneurshipSuccessful entrepreneurship requires asking the right questions, even if they are difficult. Learn from Michael Seibel's skill of asking counterintuitive questions to delve into motivations and assumptions. Shortcut solutions don't work in business.

      Asking the right questions is essential for successful entrepreneurship. While Choose Your Own Adventure books allowed readers to avoid consequences by flipping ahead to a desired ending, there are no shortcuts in business. Michael Seibel, co-founder of Justin.tv and Twitch and a partner at Y Combinator, learned the power of asking difficult questions in high school debates. This led him to question the value of the school tracking system and ultimately helped him succeed at Yale and in his career. Aspiring entrepreneurs can learn from Michael's skill of asking counterintuitive questions to get to the heart of motivations and assumptions.

    • Justin Kan's Startup Journey: Starting with Personal ProblemsIdentifying personal problems and asking oneself the right question can lead to drive and success in entrepreneurship. Like Justin Kan, founders should start companies to solve personal problems and find a mission with limitless possibilities.

      The story of Justin Kan and his startup journey highlights the importance of identifying personal problems as a starting point for entrepreneurship. While starting a company was not considered cool or rational in 2005, Kan and his friend Emmett Shear took a chance and applied to Y Combinator with their calendar app Kiko. Despite Kiko being crushed by Google Calendar, Kan's next pitch - livestreaming his day-to-day life on Justin.tv - led to the invention of a platform that allowed himself to become an influencer. YC always tells founders to start companies to solve personal problems, and asking oneself this question can lead to a mission with limitless drive.

    • Importance of Asking Critical Questions When Starting a CompanyDon't overlook important questions such as the sustainability and scalability of your product when starting a company. Always be proactive in asking the big questions to ensure future success.

      Michael Seibel helped his friends start a company and became the CEO of Justin.tv at the age of 23. However, when an investor pointed out that their product was not sustainable, they had to ask themselves the important question, "Will this continue to work and scale down the road?" It's easy to overlook critical questions when starting a company, but it's crucial to consider not only how something is working now, but also how it will work in the future. Gideon Yu's assessment of their product served as a wake-up call and reminder to always be proactive in asking the big questions.

    • The Power of Asking the Right People for HelpBuilding a strong network is important for short-term survival. Talk to users instead of just investors. Justin.tv's mistake was asking investors for advice instead of users. Focus on what inspires users for success.

      Building a strong network around your company is essential, especially when you're focused on short-term survival. When asking questions, it's important to find the right people to ask for help. Investors and customers operate in very different habitats, and while investors may have resources, they can fall short when it comes to understanding what users want. Therefore, talking to users is crucial. Justin.tv made the classic error of asking investors which idea would work instead of talking to users. However, Gideon Yu's advice prompted the team to take another look at what their users were energized by. As a result, the Justin.tv team split their focus on two new products that eventually led to the success of Twitch and SocialCam.

    • The Importance of Asking the Right Questions in BusinessBy understanding the motivations behind a decision, entrepreneurs can make better decisions and stay true to their mission. It's important to look at multiple viewpoints and ask deeper questions.

      Asking the right question is crucial in making important decisions, especially in business. Not looking at a situation from multiple viewpoints and understanding a range of motivations can cause one to miss out on opportunities. Michael Seibel and Bing Gordon's conversation highlights the importance of asking deeper questions to fully understand the motivations behind a decision. In the case of SocialCam, Seibel realized that his mission wasn't focused on video and that it was time to sell. Asking the right question can lead to better outcomes and enable entrepreneurs to stay true to their mission.

    • The Value of Struggling with Existential Questions in Personal and Professional GrowthEmbrace and learn from the difficult questions and challenges in life, as they define who we are as humans and drive personal and professional growth beyond what measurable metrics can show.

      Effective people thrive on work and challenges, even if it means getting "punched in the face." Michael Seibel, the CEO of Y Combinator's startup accelerator program, sees himself as a therapist for the founders he works with, helping them ask the right questions to prompt changes in thinking. However, the answers to these questions are not always numerical or measurable. Philosophers argue that hard choices based on competing values are what make us human and define who we are. Therefore, struggling with existential questions is a gift, an intrinsic part of being human. As Picasso once said, "computers are useless. They can only give you answers."

    • Michael Seibel on the Truths and Lies for EntrepreneursFocus on product-market fit, not just company building. Beware of the false notion that money, employees, or smart investors will solve problems. Irrational motivation, such as working with a friend, is necessary for successful entrepreneurship.

      Michael Seibel of Y-Combinator helps struggling entrepreneurs focus on the right things versus the wrong things. He warns against three classic lies and half-truths that kill YC companies: believing money, employees, or smart investors will solve problems. Instead, entrepreneurs should worry about product-market fit, not company building. YC is not just about advice and fundraising; the ultimate goal is to help startups make money. The pandemic has allowed YC to innovate, and changes include virtual engagement, more diversity, and international reach. Every founder must ask themselves the existentially uncomfortable question: should I be a founder? Seibel believes an irrational motivation is necessary, and it can come from different sources, such as working with a friend.

    • Finding Motivation and Preparing for Failure as a FounderBefore starting a company, identify your personal motivation and prepare for the possibility of failure. Seek feedback from smart individuals to determine whether your idea is worth pursuing. Keep making good decisions by examining your motivations.

      When starting a company, it's important to identify your deep source of personal motivation that will keep you going through tough times. This motivation may stem from irrational ties, such as working with a best friend, solving a problem in your community or running away from something. Founders need to understand that their business may not work and should prepare themselves that success may be lower than expected. Seeking feedback from the smartest people you know will help determine whether your idea is worth pursuing before you invest a lot of time and energy into it. Keep making irrationally good decisions by constantly asking questions and examining your motivations.

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