As a founder, I constantly face trade-offs, debating different ideas and assumptions, which can lead to mistakes, such as underestimating the difficulty of replacing established hotel systems.

Engaging in hard questions before a project starts enables us to ship something successful later.

When discussing creative processes with tech founders, using analogies related to development can help bridge understanding.

Talking to an overly optimistic founder can initially be exciting, but as the conversation continues, you may become confused about their lack of tangible progress or insights.

A single impactful conversation with an advisor can provide insights that general principles from books cannot, especially in nuanced environments.

During prototyping, we make trade-offs, such as sacrificing battery life for desired functionalities, which requires careful decision-making.

It's beneficial to have a nuanced understanding of how hard it is to build something successful. Sometimes, underestimating the difficulty can be helpful, but be cautious of flipping into a negative mindset when challenges arise.

If the project is doable with existing technology, we can reach a conclusion about what's possible to build in just a few sessions.

Asking someone for advice can change the dynamic of the conversation, leading to richer and more detailed information from them.