How to Raise Money
Paul Graham's definitive essay on early-stage fundraising, distilled from watching hundreds of YC companies raise. Covers why fundraising feels harder than it is, breadth-first search weighted by expected value, getting to yes/no fast, and the dangers of raising too much or letting fundraising drag on.
The Fundraising Wisdom That Helped Our Founders Raise $18B in Follow-On Capital
First Round distills lessons from over 1,000 rounds raised by its portfolio into a tactical playbook for follow-on fundraising: narrative construction, running a tight process, benchmarking traps, and partner-meeting dynamics.
On the Road to Recap: Why the Unicorn Financing Market Just Became Dangerous… For All Involved
Gurley's landmark analysis of the late-stage unicorn financing market: how dirty term sheets, valuation obsession, and the incentives of every player (founders, VCs, LPs, bankers) set up companies for painful recaps. Written at the top of the 2015-16 cycle and vindicated repeatedly since.
Invest in Lines, Not Dots
Suster's most famous mental model: every founder-investor interaction is a dot, and investors gain conviction from the line those dots draw over time. Argues founders should meet investors months before raising and show progress against stated plans.
A Fundraising Survival Guide
Graham on the emotional reality of raising: why fundraising is demoralizing by design, why investors herd and stall, and how to keep morale and the company alive through the process. Written mid-financial-crisis.
Postmortem of a Venture-backed Startup
The CEO of Sonar (millions of downloads, ~$2M raised) explains the company's death: chasing engagement over growth, a failed nine-month attempt to sell rather than cut costs, and how investor incentives shaped the endgame. Read by over a million people.
How to Raise Investment
The Monzo and GoCardless founder (later YC partner) condenses raising ~$400M across six years into a practical guide: sequencing angels before VCs, running a tight process, and why business quality dominates fundraising tactics.
Black Swan Seed Rounds
Altman observes that the best investments he's made were rounds nobody else wanted, and the hottest, most oversubscribed seed rounds mostly produced mediocre outcomes. Explains why consensus and quality are inversely correlated at seed.
The Non-Obvious Guide to Fundraising
A 4x founder turned VC lays out what actually drives fundraising outcomes beneath the standard advice: psychology, sequencing, the 'ladder of proof', and how VCs really talk about deals internally.
The Problem with Taking Seed Money from Big VCs
Dixon's classic warning about signaling risk: when a large multi-stage VC seeds you and then declines to lead your A, the market reads it as a kiss of death, regardless of your actual progress.
Playing Different Games
The essay that explained the 2021 Tiger Global phenomenon: how deployment velocity, price insensitivity, and low-friction terms let some funds play an entirely different game, and what that means for founders choosing among capital providers.
High Resolution Fundraising
Argues for rolling closes on convertible instruments instead of monolithic rounds: take committed money immediately, reward early conviction with better terms, and dissolve the herd-waiting equilibrium among seed investors.
Process and Leverage in Fundraising
Seibel on the mechanics of leverage: investors respond to scarcity and competition, so batch your meetings, create parallel processes, and never negotiate from a single-bidder position.
How to Raise a Series A
Distilled from YC's Series A program data: how A rounds actually happen, why 'we'll preempt you' conversations mislead founders, benchmark metrics, and running a deliberate A process instead of drifting into one.
The Post YC Slump
Altman on the pattern where startups treat closing a round as the achievement, coast afterward, and die: fundraising success is a lagging indicator that buys time, nothing more.
Front Series B Deck
The actual deck behind Front's $66M Sequoia-led Series B, published with commentary on how the narrative evolved from the Series A and what growth evidence carried the round.
Fundraising 101: I'm currently in NY! *Buys Flight to NY*
A young founder's candid, funny account of the performative side of fundraising: manufacturing 'I happen to be in town' moments, reading investor signals, and the theater everyone pretends isn't happening.
Some Thoughts on Seed Investing
Wilson candidly reviews USV's own seed investing record and explains how a multi-stage firm actually thinks about seed checks, follow-ons, and the reserved-capital math behind them.
The Hardest Round to Raise for Startups
Data analysis showing Series B is statistically the hardest round: seed enthusiasm has faded, growth-stage proof isn't in yet, and the company is valued on early scaling evidence alone.
Second Seed Rounds: How They Impact a Startup's Ability to Raise a Series A
Quantifies the second-seed phenomenon: how common repeat seed rounds are and what they do, statistically, to a company's Series A odds and terms.
It's All Pre-Series A Now
The leading pre-seed investor argues stage labels below Series A have lost meaning: everything before the A is one continuous proving period, and founders should plan capital and milestones accordingly.
Out of the picture: why the world's best photo startup is going out of business (Everpix)
The definitive reported account of Everpix's death: a beloved product with paying users that ran out of runway mid-raise; the founders later open-sourced their pitch decks, metrics, and investor pipeline. A masterclass in how good products die from failed fundraises.
Mattermark Has Raised $2M in Our Second Seed Round
Morrill explains publicly why Mattermark took a $2M second seed instead of the Series A she'd been pitching: two years of nonstop fundraising, a bridge from a customer-investor, and the honest math of raising below your hopes.
Are VCs Still Investing? The state of fundraising in the spring of 2020
Written inside the COVID shock: a VC candidly reports what his firm and peers were actually doing (versus saying) about new deals, and advises founders on raising into a frozen market.
Front Series C Deck
The third installment in Collin's published-deck series: the actual deck behind Front's $59M Series C, showing how a growth-stage narrative differs from the A and B stories she'd already published.