I was impressed by Evan Williams' genuine concern for his investors after Odio went out of business, which made me eager to invest in his next venture, Twitter.

After Posterous was acquired by Twitter but ultimately shut down, I realized that my own actions and inactions contributed significantly to the startup's failure.

I was the first investor in Venmo and played a significant role in seeding Solana, which yielded almost a 2,000x return. The key to successful investing is finding ideas that others think are wrong but are actually right.

During a challenging fundraising round, I once offered to return investors' money because I believed in the long-term vision of Discord over short-term gains.

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

Integrity in business is crucial; I chose not to lead the investment in Facebook to maintain my integrity, even though it was a great opportunity.

In 2008, I struggled to raise funds for Twilio due to the global financial meltdown, and many investors dismissed our developer service idea as foolish.

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

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.