Every raise runs through a wall of nos. Founders who heard a hundred rejections and investors who deliver them explain what rejection means and how to convert objections into a sharper pitch.
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.
1h 9m
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.
26 min
YC partners share real investor horror stories from their founder days and from companies they've advised: exploding term sheets, tranched deals gone wrong, investors behaving badly after wiring, and how founders should protect themselves.
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.
47 min
Ex-YC founder Diego Rojas (Shieldbase AI) shares fundraising lessons across YC and post-YC rounds, including what worked in investor conversations for an AI startup and what he'd do differently.
51 min
Stitch Fix founder Katrina Lake at Stanford ETL on building the company through investor skepticism about women's retail, raising less than peers, and going public anyway.
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.
9 min
Angel investor Alicia Syrett catalogs the real reasons angels and VCs say no — most of which founders never hear — drawn from hundreds of her own pitch meetings.
7 min
YC founders confess their actual fundraising mistakes: optimizing for valuation, taking bad money, serial meetings, and misreading investor interest.
33 min
Founders at YC's Female Founders Conference compare fundraising experiences: rejection patterns, investor bias, and tactics that worked, with disagreement between panelists on the right approach.
36 min
At TechCrunch Disrupt 2024, VCs give live unrehearsed feedback on audience members' actual pitch decks, disagreeing with each other about what works.
49 min
Startup Grind panel on overcoming bias while fundraising as an underrepresented founder, with firsthand accounts of coded feedback and the workarounds that got checks written.
58 min
Startup Grind London panel on the snakes and ladders of fundraising: founders trade stories of near-misses, lucky breaks, and process disasters with investor commentary.