Fundraising is a head game as much as a spreadsheet game. Founders and investors here unpack the psychology on both sides of the table: fear, FOMO, confidence, and how investors actually decide.
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.
4 min
Tovala founder David Rabie recounts the moment his Series B fell apart, what it felt like, how the company survived, and how they eventually got funded anyway.
1h 0m
Backstage Capital's Arlan Hamilton on going from homeless to VC, her $5M crowdfunding raise for her own firm, and educating underestimated founders on how capital actually works.
47 min
A founder who failed 22 times before building a $2.5B company tells My First Million the full arc, including the fundraising dead-ends, near-bankruptcies, and the raise that finally worked.
8 min
Sendbird CEO John Kim on why most startup CEOs fail, drawing on his own near-death fundraising moments and what actually earned investor conviction.
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.
23 min
A female founder and her investor jointly recount going from seed to Series A during the pandemic: both sides of the same deal, including what the VC saw internally.
56 min
Chemistry's Mark Goldberg (ex-Index) on why decision-making is broken inside large VC firms: politics, consensus damage, and what that means for founders pitching them.
3 min
Bill Gurley argues venture capital is structurally a bad industry: excess capital, misaligned incentives, and what that means for founders taking money at peak prices.
1h 11m
Freestyle's Jenny Lefcourt on making non-consensus bets, avoiding hype-driven investing, and what founders misread about how seed VCs form conviction.
1h 7m
Mark Suster returns to TWiST on the ANGEL podcast: alignment between founders and investors, setting reality with your board, and raising in down markets.
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.
SaaStr session on six things no one tells you about raising a seed round: the emotional arc, ghosting, party-round pitfalls, and closing dynamics.
53 min
Stanford CS183F Startup School session on how to raise money and succeed long-term, connecting fundraising decisions to company outcomes years later.
9 min
NFX on why VCs now expect founders to move dramatically faster, and how speed itself became the core fundraising signal in the AI era.
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.
52 min
Stanford GSB's Building Momentum session on diversity in venture fundraising: data on funding gaps plus firsthand founder and investor accounts.
11 min
Slush fireside chat on the psychology of raising money: fear, rejection resilience, and the mental game of a raise, told through the speakers' own rounds.
18 min
Web Summit session on managing the investor-founder relationship after the round: boards, conflict, and keeping investors useful.
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.
29 min
Stella & Dot founder Jessica Herrin and Jenny Lefcourt — co-founders together in the 90s — compare notes across founder and investor seats on what raising money really takes.
1h 7m
YC co-founder Jessica Livingston on entrepreneurship through the venture lens: stories from early YC batches, what founders misread about investors, and how the best founders handled early fundraising.
Harry Stebbings interviewed about his own raises: building 20VC's funds from a bedroom podcast, being underestimated, and what pitching LPs taught him about pitching generally.
1h 30m
Long-form biography interview with Harry Stebbings on raising $800M in funds starting at 18: LP rejections, the grind, and specific fund-raise mechanics.