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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.