Cloudflare's Worst VC Stories: The Sequoia Pass and the Andreessen Ambush
Cloudflare's CEO shares two of the company's worst fundraising stories: a Sequoia partner who passed because he didn't think a woman (co-founder Michelle Zatlyn) could lead a security infrastructure company, and an unprepared meet-and-greet with Marc Andreessen that turned out to be a full pitch. Posted during the June 2026 viral VC horror-story wave.
Objections & RejectionFundraising EthicsSeedThe GP Who Slept Through a $15M Series A Pitch
Isenberg describes pitching a $15M Series A at a top-3 VC firm while one of the general partners slept for 30+ minutes and everyone pretended not to notice. The post kicked off the June 2026 viral wave of founders sharing VC horror stories, drawing replies from Mark Pincus, Travis Kalanick, Matthew Prince, and others.
Investor MeetingsFundraising PsychologySeries AWhat Investors Will Ask You, and Why: Decoding the Fundraising Process
A former founder turned pre-seed VC (20,000+ pitches reviewed) explains the questions investors actually ask, and the underlying reason behind each one, so founders are never blindsided in meetings.
Investor MeetingsRaise ReadinessPre-SeedThe 10 Most Common Fundraising Mistakes (From Helping Founders Raise $5B)
Breslow frames fundraising as a game with learnable rules and lists the ten most common founder mistakes, including building investor relationships too late, over-long decks (VCs spend ~3 minutes on a deck), and taking rejection personally.
Fundraising StrategyPitch DeckAny Stage12 Questions Founders Should Ask VCs Before Taking Their Money
A Founder Collective GP flips the diligence table: twelve specific questions founders should ask potential investors (fund size, reserves, decision process, references) instead of only optimizing for getting to yes.
Investor ResearchInvestor MeetingsSeedPitching Zynga to a Sleeping Partner: 'Weekend at Bernie's Meets Silicon Valley'
Pincus recalls pitching Zynga in 2007, when no firm wanted to back the company, to a partner who fell asleep mid-pitch. Zynga went on to a multi-billion-dollar IPO.
Investor MeetingsObjections & RejectionSeedPitching a VC in His Parked Lexus: Kalanick's 2001 Hustle Story
Kalanick describes intercepting a VC who was fleeing his own office to avoid their 2001 meeting, then pitching him from the passenger seat of the investor's parked Lexus during the dot-com winter.
Investor MeetingsCold OutreachSeedTAM Is Overrated, Go-To-Market Pull Is Underrated
Yin argues investors over-index on TAM slides while founders under-argue market pull and go-to-market, and explains what she actually wants to see instead of a top-down market-size number.
StorytellingPitch DeckPre-SeedSleeping Partner, Scowling Partner, Term Sheet Anyway
Wessel, now a First Round partner, recalls a 2015 Series A pitch where one famous partner slept and another scowled throughout, then the firm sent a term sheet two hours after IC and was shocked she declined.
Investor MeetingsTerm SheetsSeries AHow VCs Should Behave in Pitches: Put Founders at Ease
A seed VC lists concrete behaviors investors should adopt in pitch meetings, pitch yourself first, show vulnerability, don't check your phone, acknowledging how stressful pitching is for founders.
Investor MeetingsFundraising PsychologyPre-Seed25 Traits of the Ideal Early-Stage VC
A crowdsourced-and-curated list of 25 best-practice traits for early-stage VCs, cc'ing prominent investors who debated it in replies; a useful rubric for founders scoring prospective investors.
Investor ResearchInvestor MeetingsPre-Seed20 High-Status Questions to Ask in VC Meetings
Frames fundraising as a status game and provides 20 specific questions founders can ask in VC meetings to signal selectivity and flip the chase dynamic.
Investor MeetingsMomentum & SignalingSeedHow to Run Board Meetings That Don't Waste Your Investors
From years of sitting in board rooms, an investor shares how first-time founders can run board meetings well: preparation, pre-reads, and engaging members strategically instead of presenting at them.
Investor UpdatesInvestor MeetingsSeed