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.

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.

Dropbox's founders faced challenges in predicting their success early on because many others were working on similar solutions, highlighting the importance of execution.

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

The partnership came together when I realized my heart wasn't in venture capital; I wanted to build. I felt lost after leaving Dropbox, where I was part of a product that 400-500 million people were using.

The biggest mistake is being stingy with equity, which can lead to co-founders leaving when things get tough.

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

The error of omission, where investors fail to back successful companies, is a more significant risk in venture capital than the error of commission, where they invest in failing companies.

Founders mistakenly avoid markets with existing competitors, but these markets can indicate a real demand for solutions that existing products fail to address, as seen with Dropbox's success despite many competitors.