I invested in Twitter after Evan Williams returned money to investors from his failed startup, Odio, showing his integrity and commitment to his investors.

Gary Vaynerchuk once told me he invests in the founder, not just the product, highlighting the importance of the story behind the people involved.

After being encouraged by founders like Drew Houston and Sam Altman, I applied to Y Combinator, despite my initial hesitation about giving up equity.

At Y Combinator, I was inspired by the ambitious mindset of other founders, which contrasted sharply with the skepticism we faced before. It motivated me to fully commit to making Watsi a reality.

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.

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.

Investors were supportive when I decided to pivot from our game store after realizing it wasn't worth the investment, showing their confidence in our ability to figure things out.

I was inspired by innovators like Elon Musk, which led me to pursue investing as an angel investor, focusing on companies that can impact millions of lives.

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