Angel investor and host of This Week in Startups, known for blunt takes on pitching and angel dynamics.
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.
Long-form conversation with Upfront Ventures' Mark Suster on how to pitch VCs, why he dislikes demo days, what separates the best founders, and how Series A decisions really get made inside a firm.
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.
Union Square Ventures' Fred Wilson in a long-form TWiST conversation on how USV picks investments, his views on founder-investor relationships, and stories from Twitter/Tumblr-era deals.
A longevity startup founder explains to TWiST why they raised in Japan instead of Silicon Valley: investor appetite differences, valuation trade-offs, and cross-border round mechanics.
Hustle Fund's Elizabeth Yin on her high-volume portfolio strategy, how tiny first checks change the founder-VC dynamic, and her outlook on seed fundraising.
Freestyle's Jenny Lefcourt on making non-consensus bets, avoiding hype-driven investing, and what founders misread about how seed VCs form conviction.
Jenny Lefcourt walks through her 'ultimate pitch' framework slide by slide, showing exactly what a seed VC wants in each part of the deck and the meeting.
Mark Suster returns to TWiST on the ANGEL podcast: alignment between founders and investors, setting reality with your board, and raising in down markets.
Wilson Sonsini partner Becki DeGraw walks TWiST through negotiating a term sheet: which terms actually matter, market norms, and where founders should spend negotiating capital.
TWiST legal-basics episode on board seats: why you effectively can't fire a VC from your board, and the cautionary situations that produces.
Jason Calacanis answers founder questions about raising a seed round in 2026: current check sizes, AI-market dynamics, accelerator math, and what he funds today.
Kruze Consulting's Scott Orn on writing investor updates that work: cadence, structure, the ask section, and how updates set up the next round.
Early TWiST legal-basics segment on raising from angels: convertible instruments, accreditation, and the paperwork of a first close.
Jason Calacanis explains how to cold-email angel investors in a way he'd actually answer, with the exact structure and signals he looks for.