How to Win by Daniel Gross | Summary and Q&A

October 25, 2018
Y Combinator
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How to Win by Daniel Gross


Former YC founder and partner, Daniel Gross, discusses the mistakes startup founders often make and provides insights on staying healthy and focused while building a startup.

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Questions & Answers

Q: How does Daniel Gross describe the mentality of a startup founder?

Daniel Gross compares the mentality of a startup founder to that of an athlete competing at the Olympics, highlighting the difficulty and challenges they face.

Q: Why does Gross believe it's important for founders to work smart, not just hard?

Gross believes that focusing solely on working hard without working smart can lead to burnout and hinder success. He emphasizes the need for founders to prioritize their physical and mental well-being.

Q: According to Gross, what are some common mistakes that startup founders make when it comes to their own personal growth?

Gross identifies some common mistakes that founders make, including overworking without paying attention to their physical health, neglecting sleep, sacrificing nutrition, and failing to exercise their minds and bodies.

Q: What advice does Gross give for improving leadership skills as a startup founder?

Gross suggests moving from a first-person to a third-person perspective, developing a clear sense of values and ideals, and learning how to motivate and inspire others. He also encourages founders to create a positive work environment where employees can thrive.


In this video, Daniel Gross, former YC founder and partner, discusses the importance of maintaining mental and physical well-being as a startup founder. He highlights common mistakes that novice athletes tend to make while playing in the "Olympics" of startup life. Gross provides advice on sleep, food, exercise, mindset, and leadership, emphasizing the need for founders to invest in themselves and avoid working hard but not smart. He also explores different stages of adult development, focusing on the self-authoring and self-transforming minds as vital for becoming an inspiring leader.

Questions & Answers

Q: How does Daniel Gross describe startups for founders?

Gross compares startups to the Olympics, noting that being a founder is like being an athlete in one of the hardest games.

Q: Why do startup founders often make mistakes when it comes to their personal well-being?

Many first-time founders lack a mental model for what greatness looks like in terms of managing themselves due to a lack of experience working for respected managers or leaders.

Q: What are some common mistakes founders make regarding their sleep?

Founders often believe that working long hours and sacrificing sleep equals productivity, but Gross emphasizes the importance of quality sleep and optimizing one's sleep environment.

Q: How does Gross suggest founders optimize their sleep?

He advises being frugal in general but spending lavishly on sleep essentials, such as sleep masks. He also recommends avoiding using an alarm clock and considers resetting the natural sleep cycle using melatonin for software engineers.

Q: How does Gross advise founders to approach their diet and food choices?

Founders should focus on eating healthy foods and avoid junk food. Gross suggests that junk food should be eliminated from the workplace, promoting the consumption of healthy food to improve overall judgment and performance.

Q: What is Gross's advice on exercise for founders?

Gross believes that exercise is crucial for founders' physical and mental well-being. He suggests spending time outdoors or engaging in any form of exercise and celebrating small successes to create positive memories associated with physical activities.

Q: How can founders improve their leadership skills?

Gross recommends moving toward a self-authoring mindset, where founders have a consistent independent frame of mind and hold clear values, ideals, and personal goals. He also encourages thinking in systems, being genuinely curious about others, and embracing infinite games.

Q: How does Gross define the self-authoring mind and the self-transforming mind?

The self-authoring mind is characterized by having independent thoughts, clear values, and goals, as well as being accountable for one's emotions. The self-transforming mind constantly evolves and adapts by adopting ideas and ideologies from others, being curious, and thinking in systems.

Q: How can founders progress to the next stage of adult development?

Gross suggests evaluating one's own stage of development and aiming to ask genuinely interesting questions to better understand others and challenge oneself. He also highlights the importance of continuously learning, experimenting, and iterating.

Q: What advice does Gross have for founders in terms of improving themselves and their companies?

Founders should prioritize their mental and physical well-being, treat themselves like athletes, and avoid falling into the trap of working hard without working smart. Gross emphasizes the need to constantly learn, iterate, and surround oneself with peers in order to grow as a leader.


Daniel Gross advises startup founders to prioritize their mental and physical well-being in order to be successful. He highlights common mistakes, such as overworking without proper sleep and nutrition. Gross suggests optimizing sleep environments, eating healthy food, and engaging in regular exercise. Additionally, he emphasizes the importance of mindset and leadership development, encouraging founders to transition to self-authoring and self-transforming minds. Through continuous learning, iteration, and curiosity about others, founders can improve themselves and their company's success.

Summary & Key Takeaways

  • Daniel Gross compares being a startup founder to being an athlete at the Olympics and highlights the importance of avoiding common mistakes in order to succeed.

  • He emphasizes the need for founders to work smart, not just hard, and to prioritize their physical and mental health.

  • Gross discusses the significance of sleep, nutrition, exercise, and continuous learning for founders, as well as the importance of building strong leadership skills.

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