One of the biggest mistakes I made was relying too much on venture capitalists' advice instead of trusting my own vision.

I regret not investing in Airbnb when I had the chance; I was focused on my own startup and missed the opportunity to meet with them before they signed with Sequoia. If you move slowly in investing, you're likely to face adverse selection; companies that take too long to engage may not be the best opportunities.

I learned that sometimes ignorance can lead to unique strengths, as our inexperience in angel investing led to the successful batch funding model at Y Combinator.

I learned a lot from my first startup, especially about what not to do, like playing startup without having product-market fit.

I found that I prefer running a company over being on the sidelines as an investor; many founders miss this realization when they start investing.

I missed out on investing in Dropbox because I canceled a meeting with Drew, which was poor investor behavior and cost me a significant opportunity.

I made the mistake of comparing my startup to competitors who had already raised money, which led to unrealistic expectations about my own fundraising efforts.

In moments of self-doubt, I learned that many successful entrepreneurs faced similar challenges and grew by making mistakes and learning from them.

After getting into Y Combinator, we made early-stage mistakes by hiring without proper culture fit vetting and dreaming too big without focusing on execution.