Airbnb CEO Brian Chesky talks with Jason Calacanis about the company's early days: living off credit cards, the cereal-box hustle, and the wave of investor rejections at a $1.5M valuation before YC and Sequoia came in. Strong sections on what rejection taught him about conviction.
The canonical fundraising-rejection story told firsthand by the founder, with specifics (names, numbers, emails) rather than legend.
This video was created by This Week in Startups and features Brian Chesky. We summarize and link with attribution; all rights belong to the creator.
Watch on YouTube →
12 min
Brian Chesky reads an actual rejection letter Airbnb received from an investor, then unpacks what the rejections got wrong and how the founders kept going.
1h 6m
Canva co-founder Melanie Perkins recounts pitching for three years and being rejected by more than 100 investors before closing Canva's first round, including how she reworked the pitch around each objection. She details the kitesurfing-with-investors period in Silicon Valley and how rejection shaped the company's strategy.
58 min
Hustle Fund GP Elizabeth Yin takes live pitches from real founders and gives unfiltered feedback in real time, explaining her actual investment thought process as she reacts to each pitch.