The comprehensive fundraising handbook for startup founders.

With input from over 60 entrepreneurs, investors, and legal experts, this in-depth resource is your companion as an entrepreneur. Filled with practical pitching advice, term sheet details, real-world scenarios, and pitfalls to avoid.

  • 310-page online book
  • 778+links and references
  • Digital access to this title in the Holloway Reader
  • Downloadable PDF for personal offline use
Length: 310 pages
Edition: e1.1.4
Last Updated: 2023-09-15
Language: English
ISBN (Holloway.com):
978-1-952120-01-5
ISBN (print):
978-1-952120-21-3
Founders shouldnโ€™t have to figure fundraising out the hard way when they can learn from those who have already been through the process. The Holloway Guide to Raising Venture Capital is full of practical advice that will be helpful to any entrepreneur.Brad Feld(Foundry Group)

Everyone should have access to expert knowledge.

Venture capital is a powerful tool for entrepreneurshipโ€”one that can help overcome some of the numerous challenges of starting and scaling a new business. But the path of deciding if, when, and how to raise early-stage venture capital is navigated most easily by those with past experience, insider knowledge, and the right connections. Itโ€™s notoriously easy for founders to take wrong turns in their path to successfully finance a company.

The lead author of this Guide, Andy Sparks, raised $17M for his last startupโ€”having failed to secure any funding for his first company. Heโ€™d moved to Silicon Valley without a network, and spent the next four years piecing together how fundraising works, from hundreds of conversations, countless hours of internet searches, and multiple $900 sessions with lawyers.

Learning how to fundraise doesnโ€™t have to be so painfulโ€”or so costly. Anyone aspiring to build a company should have access to the experiences and knowledge of those who have gone before. Weโ€™ve pulled together 40 expertsโ€”lawyers, founders, and investorsโ€”to build a practical Guide that helps founders approach the process with confidence.

Reviews

Rafael Corrales
Background Capital
I wish this resource had existed back when I was a CEO raising money from VCs. In my work today as a seed investor, I share with my portfolio founders a lot of the knowledge gathered in this Guide. Now that this definitive resource exists, I'm going to send it to every founder I work with!
Tyler Tringas
Earnest Capital
Raising venture capital is a huge decision for founders. I highly recommend this Holloway Guideโ€”it dives deep into how to raise, but also gives an honest assessment of why founders should or shouldnโ€™t raise VC and the alternative paths for building companies.
Sean Byrnes
CEO at Outlier and former CTO at Flurry
Venture funding of startups is a secretive process that has typically required insider knowledge to navigate well. This new Holloway Guide pulls back the curtain and shares everything you need to know as a new founder raising money for the first time. I wish I had access to this kind of knowledge when I was getting started; it would have saved me years of hard lessons.
Zach Klempf
CEO, Selly Automotive
Holloway has taken a thoughtful, non-biased approach putting together this comprehensive Guide to raising venture capital. Rather than being a mile wide and an inch deep like other material out there, they have focused on context and quality.
Ryan Hoover
founder of ProductHunt and investor at Weekend Fund
We need more startups. But many never get the funding they need to fulfill their true potential. This Guide is designed to empower founders with the insights and strategies to find investors that share the same convictions as the founders themselves.
Jared Erondu
Earnest Capital
Holloway has brought a digestible and actionable first-class experience to a very intimidating topic. The clarity that this Guide offers will leave you with answers, not headaches. If you plan on raising, I can confidently say that this is the only resource you need to read.

Table of Contents

Part I
The Landscape
Assessing Whether to Raise
Determining When to Raise
Bias and Discrimination in Fundraising
Part II
Financing
Choosing a Financing Structure
Part III
Sourcing and Pitching
Designing Your Pitch
Getting the Meeting
Investor Meetings
Part IV
Term Sheets
Essential Terms
Other Terms
Sample Term Sheets
After the Term Sheet
Appendices
Appendix A: Networking and Mentorship
Appendix B: Returns, Management Fees, and Carried Interest
Appendix C: Example Fundraising Pitch Decks
Disclaimer
Though itโ€™s getting better, venture capital has traditionally been a fairly closed, blackbox field. This Guide democratizes and demystifies the VC ecosystem, which is an important step toward building a more diverse and inclusive industry.Lindsay Knight(Chicago Ventures)

Researched, written, and edited by experts.

Written by practitioners. Edited by professionals.

Original Author
Andy Sparks
Contributing Authors
Rachel Jepsen
Contribution and Review
Josรฉ Ancer (Egan Nelson LLP)
Michael Brown (Fenwick & West)
Brad Feld (Foundry Group)
Chris Field (Clerky)
Eric Friedman (Building the Machine)
Alexander Graebe (HyperTrack)
Chris Harvey (Harvey Esquire)
Lindsay Knight (Chicago Ventures)
Craig Montuori (Global EIR)
Danielle Morrill (GitLab)
Leo Polovets (Susa Ventures)
Camille Ricketts (First Round, Notion)
Joe Sadusky (The Wordsmith)
Santosh Sankar (Dynamo Venture Capital)
Aaron Schwartz (Passport Shipping)
Tess Townsend (Journalists in Classrooms)
Tyler Tringas (Earnest Capital)
Joe Wallin (Carney Bradley Spellman)
Eugene Wan (The Engine)
Darby Wong (Clerky)
Production
Haley Anderson โ€” Research and Definitions
Hope Hackett โ€” Swiss Army knife
Nathaniel Hemminger โ€” Production
Rachel Jepsen โ€” Editor
Joshua Levy โ€” Editor and Production
Sakhi MacMillan โ€” Copyeditor
Courtney Nash โ€” Editor
Dmitriy Kharchenko โ€” Graphics
Leigh Taylor โ€” Graphics
And 28 more

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  • 310-page online book
  • 778+links and references
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We believe in a reading experience that goes beyond paper or e-books. Reading on Holloway means a distraction-free, interactive format to help you find what you need, when you need it, in your browser. Digital access means access to additional digital resources, future updates, curated commentary from experts and readers, and features like search and bookmarks.

Screenshot of the guide on phone and laptop

Definitions of Key Terms

โ€‹Definitionโ€‹ Product-market fit (product/market fit or PMF) refers to the notion that there is a point at which a given market responds so positively to a companyโ€™s product that the product โ€œfitsโ€ the marketโ€™s needs. A precise point at which โ€œfitโ€ has been achieved does not exist. Instead, product-market fit represents a continuum of traction that ranges from absolute clarity that a company does not have product-market fit to maybe they have product-market fit to experts disagree whether they have product-market fit all the way to itโ€™s beyond all doubt they have product-market fit.

Powerful Search Features

ESCBack
Definitions
Shadow preferred stock
Preferred stock
Sections
Preferred stock vs. common stock
Guide
Assessing Whether to Raise
usually means agreeing to protective provisions for preferred stockholders or giving up a board seat

Pitfalls and Confusions Explained

โ€‹dangerโ€‹๏ธ๏ธ Even if youโ€™ve negotiated a cap on the portion of your investorsโ€™ legal fees youโ€™re responsible for covering, your counselโ€™s fees can get out of control if you arenโ€™t careful. If your lawyers are arguing about anything meaningful, you should tell them to bring it to you before it goes back and forth between different legal teams more than once.

โ€‹confusionโ€‹ Not everyone has embraced the pre-seed term, which some consider overly specific and constraining. Until recently, a companyโ€™s earliest institutional investors were simply called seed stage firms. Some firms that consider themselves seed-stage will invest pre-product, all the way up to the last check before a Series A round.

โ€‹controversyโ€‹ A warm intro from a close friend or colleague never hurts.* But not everyone agrees you need to be close with the person making the intro. So long as the introduction is credible, it can be a good start, even if itโ€™s not necessarily an endorsement.*

Visual Presentations

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The Holloway Guide to VC is an incredibly well-curated resource thatโ€™s easily searchable and is heavily grounded in first principles. I wish Iโ€™d had this guide when trying to raise VC money for my first startup!Kiren Srinivasan(Holberton School)

Why pay for an online book?

At Holloway, we imagine a place on the web where depth, quality, and high-value writing are the norm. A place where expertsโ€™ ideas are accessible to anyone. Where thoughtful, inclusive, and well-written resources win over quick takes, self-promoting blog posts, and content marketing.

We believe you, the reader, know the difference. Itโ€™s the 2020s. You recognize sites riddled with ads and clickbait headlines. Deep and comprehensive resources take expertise, time, and money to build. By buying access to this title, youโ€™re supporting a place online that makes longform reading a pleasureโ€”and allowing us to pay authors, contributors, engineers, and editors who build and improve them. Holloway is a new and powerful way to publish. We hope youโ€™ll join us on the journey.

Does this sound like you?

  • I just got off the phone with my lawyer about my term sheet, and still feel confused about what participating preferred and full ratchet mean. I wish this stuff were just written down.
  • Whatโ€™s the difference between a managing director, partner, venture partner, principal, associate, or an analyst in a VC firm? Who should I be talking to?
  • We arenโ€™t in a standard tech hub like Silicon Valley or New York City, and donโ€™t know any investors. Where do we even start?
  • Iโ€™ve read blog posts about founders deciding against raising venture capital. How do I know whether raising venture capital is a good idea for my business?

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