Investors were hesitant to back DoorDash because, although we had strong numbers, it wasn't clear that we would emerge as the largest player in the market.

During the early days, we ran experiments to confirm that consumers would pay for DoorDash's service, which gave us confidence in our business model despite initial doubts from investors.

In 2016, 2017, and 2018, I struggled to raise capital despite positive internal metrics, which made it one of the most difficult periods for DoorDash.

Despite initial investor reluctance due to past failures in grocery delivery, we eventually closed a seed round with an investor who believed in us.

The first demo day for DoorDash was not successful, and we struggled to raise funds, putting the company at risk of going out of business.

Our initial idea for DoorDash came from observing a macaroon store owner who had turned down numerous delivery orders, which highlighted a significant market opportunity.

DoorDash founders initially handled all deliveries themselves to ensure customer satisfaction and build relationships with users and restaurants.

The founders of DoorDash learned valuable insights by personally delivering food, which helped them understand the challenges of the business.

Raising funds for a fast-growing business is easier, but the hardest round for Discord was the Series A, where many investors doubted the potential of the gaming chat app.