"What I Worked On: Lessons in Prestige, Startups, and Learning from Mistakes at Y Combinator and NASA"

"What I Worked On: Lessons in Prestige, Startups, and Learning from Mistakes at Y Combinator and NASA"

In my journey as an entrepreneur and investor, I've had the opportunity to work on various projects and learn valuable lessons along the way. One of the most important lessons I've learned is that the low end often eats the high end. It's better to be the "entry level" option, even if it means less prestige, because if you're not, someone else will be and will squash you against the ceiling. This realization has guided my approach in both Viaweb and Y Combinator.

Prestige can be a dangerous sign. When something is prestigious, it often means that many people are already pursuing it. Instead, I've found that working on things that aren't prestigious can lead to discovering something real and having the right motives. It's not that unprestigious work is inherently good, but being drawn to it can be a sign that you're on the right track and not following the common path.

One of my tricks for writing essays has always been giving talks. The prospect of standing in front of a group of people and sharing valuable information has always spurred my imagination. This is why when the Harvard Computer Society asked me to give a talk on starting a startup, I jumped at the opportunity. I believed that by sharing our mistakes and experiences, others could avoid the same pitfalls.

Creating a community of like-minded individuals is important for founders. At Y Combinator, we established a community by using a building in Cambridge as our headquarters. We would have dinner together once a week and invite experts to share their insights. Being part of a batch of startups solved the problem of isolation and allowed founders to connect with others who understood their challenges.

In my experience with Y Combinator, the problems of each batch of startups became our problems. This engagement and variety made the work incredibly fulfilling. It was a unique way to learn about startups and gain valuable insights in a short period of time.

A valuable lesson I learned from Kevin Hale is that no one works harder than the boss. As a leader, your level of dedication sets the upper bound for the rest of the team. This realization motivated me to work harder to ensure the success of Y Combinator.

Attention is a zero-sum game. If you choose to work on a project that is not the best or most suitable for you, it gets in the way of another project that could be more impactful. As I reached the age of 50, I began to understand the opportunity cost of wasting time on less meaningful pursuits.

Moving on to my experience at NASA, I discovered that the success of their projects is a result of the knowledge and collaboration of thousands of brilliant individuals. Knowledge management plays a crucial role in their work. It is about better applying collective knowledge to individual problems and creating systems to share and reflect on what is known best.

Social media has the potential to enhance learning and collaboration, but the strength of relationships matters. Developing strong ties with people is essential to getting rapid and trustworthy answers, enhancing thinking, and accelerating results. It is important to facilitate different kinds of relationships, both online and offline, to foster innovation and solve complex problems.

Learning in public can be challenging, but it is worth it. By sharing what you know and don't know, you give others the opportunity to contribute their specific knowledge and help you. This can save time and money and lead to better outcomes. The feedback, support, and improvements that result from learning in public outweigh the initial difficulties.

In conclusion, my journey in both the startup world and NASA has taught me valuable lessons about prestige, learning from mistakes, and the power of collaboration. To summarize these lessons, here are three actionable pieces of advice:

• 1. Embrace the low end: Don't be afraid to pursue opportunities that may not be prestigious. They can lead to real discoveries and the right motives.

• 2. Foster strong relationships: Whether through social media or offline connections, develop strong ties with others to enhance learning, innovation, and problem-solving.

• 3. Learn in public: Share what you know and don't know. By opening yourself up to feedback and contributions from others, you can save time, money, and improve outcomes.

By implementing these pieces of advice, you can navigate the complexities of the entrepreneurial world and continue to learn and grow in your endeavors.