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.
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.
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 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.
Front Series A Deck
Collin publishes the actual deck Front used to raise its $10M Series A, slide by slide, with commentary on what worked. Later viewed over 2 million times and followed by her Series B, C, and D decks.
How I raised a $5.1M seed as a first-time, female, solo founder for a biotech moonshot
Halioua details exactly how she raised $5.1M pre-product for a dog-longevity biotech as a solo, first-time, female founder: building the narrative for a moonshot, sequencing investors, and handling deep-tech skepticism.
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.
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.
My Startup Failed and This is What It Feels Like
Durkin founded 99dresses at 18, got into YC, lost her co-founders, and watched committed funding fall through at the worst moment, killing the company. An emotionally raw account of a collapsed round, visa pressure, and winding down.
Dear White Venture Capitalists: If you're reading this, it's (almost!) too late.
The viral 2015 essay, written while Hamilton was broke and pitching her fund, calling out venture's failure to fund underrepresented founders. It directly led to her first LP check and the founding of Backstage Capital.
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.
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.
Raising a seed round 101
Aggregates advice from founders and investors who have collectively seen 1,000+ seed raises, organized as a step-by-step process with benchmarks for round size, dilution, timeline, and meeting counts.
What I Wish I Knew About Fundraising as a First-Time Founder
A former a16z partner turned founder describes how different fundraising looks from the founder's chair: what she got wrong despite knowing the investor side, and the gap between VC theory and founder practice.
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.
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.
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.
The Anti-Portfolio: Honoring the companies we missed
Bessemer's famous public list of the legendary companies it passed on, with self-deprecating explanations ('friend rented her garage to Google's founders; David asked how he could leave the house without going near it').
How to Develop Your Fundraising Strategy
Suster's process playbook: qualify investors like a sales pipeline, research partners not firms, sequence your best prospects after warm-up meetings, and manage the raise like an enterprise deal.
Ban Warm Introductions!
Johnson's much-debated argument that the warm-intro requirement is not just exclusionary but bad investing: it selects for network proximity over merit, and firms serious about returns should build open top-of-funnel instead.
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 Rise of the Solo Capitalists
Named and documented the solo-capitalist phenomenon: individual investors raising nine-figure funds and winning competitive rounds against firms, and what founders gain and lose by taking their money.
How to Convince Investors
Graham on the substance of persuasion: convince yourself first, be a domain expert, and make the truth about your startup legible rather than performing confidence you don't have.
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.
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.
The Fatal Pinch
Defines the default-dead trap: moderate growth, months of runway, and an assumption investors will save you. Explains why bridge rounds usually don't come and what to do instead (cut costs or grow into default-alive).
Black Swan Farming
Graham explains power-law returns from the investor side: the best ideas look like bad ideas, YC's returns come from a handful of companies, and even professionals can't reliably pick winners at the time of investment.
How to Present to Investors
Practical demo-day-era advice on presenting: explain what you do in the first sentence, show a demo, and optimize for being understood rather than impressive.
I Know Everybody Told You to Send Your Fund-Raising Decks as a Link. Here's Why You Should Just Send the Deck
Suster argues against DocSend-style gated links from the receiving end: friction kills investor attention, deck-tracking paranoia is misplaced, and your deck's job is to travel inside the partnership without you.
How to Pitch Your Company
Seibel's formulaic, repeatable pitch structure: a two-sentence company description anyone can repeat, traction, unique insight, market size, and the ask, with examples of each done well and badly.
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 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.
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.
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.
SparkToro Year 3 Retrospective: Investor Payback, Systemic Challenges, and V2 on the Way
Three years after the unusual angel round, Fishkin reports real numbers: profit-sharing distributions actually paid to investors, growth against plan, and honest assessment of the model's tradeoffs.
How I Raised My $11.5M VC Fund
Yin documents raising Hustle Fund I with funnel numbers: hundreds of LP conversations, conversion rates, and tactics. Fundraising for a fund mirrors a startup raise, and she shows the whole pipeline including the rejections.
Introducing Raise Millions
Launch post for Raise Millions, Hustle Fund's free book-length compilation of tactical fundraising guidance drawn from thousands of pre-seed pitches; the post links the full free resource.
How to De-Risk a Startup
Polovets enumerates the specific risks investors price (team, market, product, execution, financing) and concrete actions that retire each one, reframing fundraising as selling reduced risk at increasing prices.
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.
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.
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.
Financing Options for Startups (MBA Mondays)
The index post for Wilson's MBA Mondays series covering every startup financing option: friends and family, angels, convertible debt, venture debt, preferred rounds, and when each fits.
A (Brief) Anatomy of a Successful Seed Raise
DocSend's dataset of thousands of real fundraising decks quantifies the seed raise: how many meetings successful raises take, how long investors actually read decks, which slides funded decks include, and seasonal timing effects.
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.
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.
Here's the Advice I Give All of Our First Time Founders
A First Round partner's standing advice to new portfolio founders, including how to work with investors after the round closes and how to set up the next raise from day one of this one.
Founder Toolkit: How to raise your seed round from top VCs & Angels
A repeat founder and angel condenses his raising experience into a toolkit: list-building, sequencing angels and funds, materials, and close mechanics, with templates.
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.
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.
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.
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.
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.
For Fundraising, Seed is No Longer a Round, It's a Phase
Walk reframes seed as a multi-year, possibly multi-round phase of proving core value, not a single event, with implications for how founders should structure and sequence early capital.
A Question About Risk That Founders Forget to Ask VCs
A short, sharp diligence-reversal tactic: ask every prospective investor 'what's a risk you're more comfortable with than the average VC?' and use the answer to test fit and conviction.
Is It Fair To Tell Founders 'Just Execute And You'll Be Fine' When We Know It's Not A Level Playing Field?
A sitting VC interrogates his own industry's meritocracy narrative: standard fundraising advice assumes network access and pattern-matching benefits that underrepresented founders don't get, and he discusses what honest advice looks like instead.
What Are Pre-Seed Rounds & Why Do They Exist?
An early definition of the pre-seed round from one of the investors who named the category: what qualifies ($750K or less, pre-product), why the category emerged, and how it chains into institutional seed.
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 We Think About Pre-Seeds at NextView
The investor-side view of pre-seed construction: why NextView prefers small aligned syndicates over large party rounds at this stage, and what that means for founders assembling one.
Founders: Please don't allow anyone to screw your early backers
Janz describes later-stage investors pressuring founders to restructure or squeeze out early angels and seed funds, and argues founders must defend the people who took the earliest risk, both morally and reputationally.
The growing dissonance between two business models (SaaS and VC)
A SaaS-focused VC admits the venture model's power-law needs are increasingly mismatched with how most healthy SaaS companies actually grow, and explores what that means for founders choosing capital.
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.
Bessemer's Published Investment Memos (LinkedIn, Shopify, Pinterest, Twilio and more)
Bessemer publishes the actual internal investment recommendation memos behind its best deals, showing exactly how partners argued for LinkedIn, Shopify, Pinterest and others: the risks flagged, the numbers at the time, and the bet being made.
The Confidential YouTube Investment Memo by Sequoia
Sequoia's actual 2005 YouTube Series A memo, made public through the Viacom lawsuit: written when YouTube was two months old with no CEO and no business plan, it shows how a top firm underwrote a raw, risky deal.
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.
Who Gets Funded to Build in Africa? Lessons from a $7.3M Nigerian Seed Round
Uses a $7.3M seed round raised by an American founder for a Nigerian-market app to examine who global VC actually trusts to build in Africa, and what local founders face by comparison.
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.
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.
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.
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.
Dear SaaStr: What Are the Top Mistakes You See New Founders Make?
Lemkin's blunt list of first-founder mistakes, the fundraising ones foremost: assuming the next round is guaranteed, burning to a plan that requires it, and wasting months pitching the wrong investors.
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