Stage · 15 of 84 articles

Series B+ fundraising, from people who have done it

By Series B and beyond, fundraising becomes a metrics and momentum business. These articles cover growth-stage dynamics: how later-stage investors evaluate efficiency, board and preference complexity, and raising when the easy narrative is gone.

First Round Review·2017 ·25 min read

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.

Fundraising StrategyStorytellingSeries AHow-To
Read the breakdown
Heidi Roizen (Tumblr)·May 2015 ·15 min read

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.

Term SheetsValuation & DilutionSeries B+Horror Story
Read the breakdown
Above the Crowd·April 2016 ·30 min read

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.

Valuation & DilutionTerm SheetsSeries B+Contrarian View
Read the breakdown
Feld Thoughts·August 2005 ·10 min read

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.

Term SheetsValuation & DilutionSeedHow-To
Read the breakdown
Kwokchain-adjacent Substack (Not Boring in Public)·April 2021 ·20 min read

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.

Fundraising StrategyValuation & DilutionSeries B+Teardown
Read the breakdown
Founder Collective·2016 ·12 min read

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.

Valuation & DilutionFundraising StrategySeries B+Data & Benchmarks
Read the breakdown
Elad Gil's blog·March 2011 ·8 min read

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.

Raise ReadinessFundraising StrategySeedHow-To
Read the breakdown
Medium·January 2018 ·10 min read

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.

Pitch DeckStorytellingSeries B+Firsthand Story
Read the breakdown
Holloway·2019 ·300 min read

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.

Fundraising StrategyTerm SheetsPre-SeedHow-To
Read the breakdown
Newcomer·July 2025 ·20 min read

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.

Fundraising StrategyValuation & DilutionSeries B+Interview
Read the breakdown
tomtunguz.com·2016 ·30 min read

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.

Fundraising StrategyValuation & DilutionSeedHow-To
Read the breakdown
tomtunguz.com·2015 ·6 min read

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.

Raise ReadinessFundraising StrategySeries B+Data & Benchmarks
Read the breakdown
The Angel VC·November 2018 ·8 min read

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.

Fundraising EthicsTerm SheetsSeries AContrarian View
Read the breakdown
Bessemer Venture Partners ·60 min read

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.

DiligenceInvestor ResearchSeries ACase Study
Read the breakdown
Front blog·January 2020 ·10 min read

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.

Pitch DeckStorytellingSeries B+Firsthand Story
Read the breakdown