How to Build a Unicorn From Scratch – and Walk Away with Nothing
A veteran VC and former founder walks through a fictional-but-realistic 'grim fairy tale' in which a founder builds a billion-dollar company and ends up with nothing, term by term: participating preferred, ratchets, guaranteed IPO returns, redemption rights.
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.
A Guide to Seed Fundraising
YC's comprehensive seed fundraising manual: when to raise, how much, SAFEs vs. priced rounds, meeting mechanics, negotiation, and closing documents, written by a YC partner for first-time founders.
Reflecting on My Failure to Build a Billion-Dollar Company
Lavingia raised $8M from top VCs at 19, failed to hit venture-scale growth, laid off 75% of his team after a failed Series B, and rebuilt Gumroad as a profitable, deliberately smaller company. A brutally honest account of what happens when you take venture money and land on the 'good but not billion-dollar' outcome.
We're Raising $3.5m in Funding: Here is the Valuation, Term Sheet and Why We're Doing It
Buffer publishes every detail of its $3.5M Series A: the valuation, the actual term sheet, investor list, ARR ($4.6M), and the unusual structure that let founders and early employees take secondary money. A landmark in fundraising transparency.
The Option Pool Shuffle
The classic teardown of how VCs quietly lower your effective valuation by putting the option pool in the pre-money. Includes the math and negotiation scripts to fight back.
SparkToro Raised a Very Unusual Round of Funding & We're Open-Sourcing Our Docs
After his bruising VC experience at Moz, Fishkin raised $1.3M from 35 angels under a novel structure allowing profit-sharing distributions instead of requiring a huge exit, and open-sourced the legal docs so others could copy it.
What Seed Financing Is For
Wilson's short, sharp definition: seed money is for building product and finding product-market fit, nothing else, and rounds sized or spent otherwise create broken cap tables and stranded companies.
Term Sheet Series Wrap Up
Index to Feld and Mendelson's 2005 series explaining every clause of a VC term sheet: liquidation preferences, anti-dilution, protective provisions, drag-along, and which terms actually matter. Later became the book Venture Deals.
Debt is Coming
Danco argues that recurring-revenue businesses funding predictable growth with dilutive equity is a historical accident, and predicts the rise of revenue-based and debt financing for startups. Sparked a wide industry debate.
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.
The Equity Equation
The 1/(1-n) rule: give up n% of your company only when the trade makes the remaining stake worth more than the whole was before. Applies the same math to investors, hires, and co-founders.
How to Raise a Seed Round
YC partner Aaron Harris's operational seed-raising manual: preparing materials, building the target list, running meetings in a compressed window, and closing with SAFEs.
Safe Financing Documents
The official home of the SAFE: current post-money SAFE documents, side letters, and YC's user guide explaining caps, discounts, and dilution math.
How Fundraising Stages Work
Plain-language breakdown of what pre-seed, seed, and A actually mean now, what each stage's investors expect, and how round sizes and expectations have drifted from the labels.
Overdosing on VC: Lessons from 71 IPOs
A seed VC analyzes 71 tech IPOs and finds no correlation between capital raised and outcome quality: the most efficient companies returned more per dollar than the most funded. Argues overcapitalization is a drug with real side effects.
How Funding Rounds Differ: Seed, Series A, Series B, and C
Gil maps what each round is actually evaluated on: seed buys the team and idea, A buys early product signal, B buys proof the machine works, C buys scaling economics, with implications for what to emphasize at each.
A Seed Round Manual for Founders: Strategies, Pitch Prep, Valuation, Traps, Tips and More
A founder who raised $1.5M+ across UK and US investors documents the whole process as a manual: what worked, the traps she fell into, and differences between London and Valley investor behavior.
How Much Funding Is Too Little? Too Much?
Part of Andreessen's legendary 2007 startup guide, written as a founder before a16z existed: how to size a raise against milestones and market windows, the pathologies of too little money and the subtler pathologies of too much.
Holloway Guide to Raising Venture Capital
A book-length, edited, citation-heavy reference on the entire venture fundraising process, from instruments and terms through negotiation and close, reviewed by dozens of practitioners.
My Conversation with Substack Co-Founders Chris Best & Hamish McKenzie Fresh Off Their $100 Million Funding Round
Newcomer interviews Substack's founders immediately after their $100M round at $1.1B: how the round came together after a rocky stretch (including a crowdfunded raise when VCs cooled), and how the narrative was rebuilt.
Reflecting on My Failure to Build a Billion-Dollar Company, Part 2
An analytical companion to Lavingia's essay: Baschez unpacks the structural reasons venture-backed Gumroad 'failed' at billion-dollar scale while succeeding as a business, examining how funding choices define what counts as success.
A Founder's Guide to Venture Capital & Startup Fundraising
Tunguz's index of his data-driven fundraising posts organized as a founder's guide: how VCs decide, round dynamics, valuation math, and negotiation, each backed by his analyses of actual funding data.
Which Fundraising Round Should You Skip?
With founders now raising 3-4 rounds before Series A, Go argues the total dilution math forces a choice: decide deliberately which round in the chain you'll skip, and shows how to reason about it.
How to raise a seed round (from a former VC turned founder)
A former VC who crossed to the founder side demystifies the seed process from both chairs: board seats, how much to raise, investor selection, and the parts of VC behavior that only make sense once you've sat in the partner meeting.
Getting Out of the Startup Rat Race
After raising a $500K seed and then nearly running out of money, Pigford describes negotiating with his investors to reset expectations and step off the venture growth track, with the actual numbers Baremetrics published all along.