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.

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.

All you need is one investor to say yes; in 2018, when we raised our Series D, it became clear internally what was going to happen next for DoorDash.

Despite progress, raising Series A was challenging due to increased competition in the food startup space, and we faced another setback in securing funding.

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.

Raising a seed round is one of the hardest challenges for a founder due to limited data and traction, especially in a space with past failures like grocery delivery.

Companies like DoorDash understood the concepts of 'default alive' and 'burn rate,' which allowed them to manage their finances effectively even in challenging times.

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

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.