I made a significant mistake by not investing in Facebook when I had the chance, which taught me to recognize exceptional founders without overanalyzing.

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 was the first investor in Android and played a role in the early days of Dropbox, emphasizing the importance of relationships in investing.

I made mistakes in the fundraising process, including not meeting enough investors and assuming a deal was done before it actually was.

In one of my worst investor meetings, I was kept waiting for hours by an investor known for making founders wait, which set a negative tone for the meeting.

The biggest mistake in WonderCo's history was not doing venture investments from 2016 to 2020, missing opportunities with talented founders from Dropbox.

My best personal investments were a third of my net worth in Facebook at an $8 billion valuation, which allowed me to transition to Dropbox.

This investor's behavior felt like a power play, and ultimately, he did not invest, making the experience even more frustrating.

During investor meetings, we faced challenges, including one investor leaving mid-pitch, which highlighted our lack of readiness.