After leaving Scribd, I immediately discussed new ideas with Paul Graham, and we decided to apply to Y Combinator again, even though we didn't have a product yet. I co-founded a subscription billing service called PipePay, but we didn't want to compete directly with Stripe, which was doing really well at the time.

Back in 2006, Y Combinator provided a fixed amount of $6,000 per person, which was significantly less than what startups receive today, but it was enough for us to survive while building Scribd.

Dropbox has evolved from merely storing files to facilitating team collaboration, highlighting the importance of sharing over just storage. It started as a file-sharing service, but I recognized early on that the role of files in people's lives was changing, especially with the rise of platforms like iTunes and Netflix.

Initially, we faced challenges with our website as users preferred YouTube over our platform, leading us to pivot our strategy based on user feedback.

I believed YouTube could become the destination for user-generated video on the internet. They had a spectacular team, and the product was delightful and easy to use, which led to Sequoia Capital backing YouTube's first financing.

The early challenges for Dropbox included maintaining growth and transitioning from a prototype to a fully functioning company after our initial success with the demo video. We need to focus on acquiring users daily to grow our product.

We realized that if PayPal failed, it would create a massive loss of over $200 million in venture capital, so we decided to pitch our best ideas to each other, including an early version of LinkedIn.

Our initial idea was to create a suite of applications for law firms, but we pivoted to a marketing application for all businesses.

We expanded Dropbox's focus beyond just file storage to include private photo sharing and team collaboration, acknowledging that files were evolving in their importance.