Startup Foundations Bundle

Five essential guides for early startups, written by entrepreneurs with decades of experience. Comprehensive, practical, and filled with insights from top startup leaders.

$275 value
$195$165
VIP code HLWY30 applied
Written by professionals who have worked at dozens of top companies...
Invaluable—it gives you the kind of insight and wisdom that is usually only found through hard earned experience, right at your fingertips.Adam Jacob(Co-Founder of Chef, on Technical Recruiting and Hiring)

Your Early Startup Survival Guides

In the early days of your startup, every decision counts. Fundraising. Equity. Hiring. Sales. Culture. The choices you make today will determine the outcome of your company—of your success or failure.

Where will you turn for advice when it matters most?

The Startup Foundations Bundle includes five essential guides for navigating the most challenging parts of building a new business:

  • Raising Venture Capital by Andy Sparks
  • Equity Compensation by Joe Wallin and Joshua Levy
  • Technical Recruiting and Hiring by Osman (Ozzie) Osman
  • Founding Sales by Pete Kazanjy
  • Remote Work by Katie Wilde and Juan Pablo Buriticá

Each guide includes the collective wisdom of dozens of entrepreneurs with decades of experience, from dozens of startups and successful companies like Buffer, Stripe, Facebook, Dropbox, Google, and Quora, as well as top venture funds and law firms. They are as comprehensive as they are practical, helping you make better decisions that set your company up for success. Get lifetime access to each online book, future updates, bookmarks, highlighting, commentary, and all other digital resources included with the title.

Featured Reviews

Founders shouldn’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, on Raising Venture Capital)
This is the first thing I share when someone is thinking about their equity compensation.
Ryley Reynolds (Thrive Capital, on Equity Compensation)
Without a doubt, this guide is the best resource I’ve read on technical hiring, by a substantial margin.
KELLAN ELLIOTT-MCCREA (Dropbox, formerly Blink Health, Etsy, on Technical Recruiting and Hiring)
Predictable Revenue introduced the world to scalable outbound sales. But it won’t work without a solid foundation. Founding Sales helps founders and other first-time sellers go from a dead stop to first gear in sales (the hardest part). Time after time first time founders and sellers try to sell and grow sales too fast, leading to failure. Founding Sales gets you started, building that foundation first so you’re prepared to scale later.
AARON ROSS (author, Predictable Revenue, on Founding Sales)
Everyone has written a guide on remote work—but no one has done so as diligently and comprehensively as Holloway. They’ve spoken to everyone who knows about remote work, and do not shy away from what’s tough or complex.
JOB VAN DER VOORT (CEO, Remote, on Remote Work)

Raising Venture Capital

What’s Inside

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

Equity Compensation

What’s Inside

Introduction
Scope
Who May Find This Useful
A Note on Fairness
Roadmap
How This Guide Is Organized
When to Turn Elsewhere
Seeking Professional Advice
Equity Compensation Basics
Growth and Risk
Compensation and Equity
The Goals of Equity Compensation
Fundamentals of Stock Corporations
Stock and Shares
Public and Private Companies
Governance
IPOs
Sales and Liquidity
Startups and Growth
Startups
Fundraising, Growth, and Dilution
Dilution Illustrations
Stages of a Startup
The Option Pool
Counting Shares
Classes of Stock
How Equity Is Granted
Restricted Stock Awards
Stock Options
Vesting and Cliffs
How Options Expire
Kinds of Stock Options
Early Exercise
Restricted Stock Units
Using Promissory Notes to Buy Stock
Less Common Types of Equity
Tax Basics
Kinds of Income
Federal Taxes
State Taxes
Taxes on Equity Compensation
83(b) Elections
409A Valuations
Taxes on ISOs and NSOs
The AMT Trap
Stock Awards vs. ISOs vs. NSOs
Taxes on RSUs
Tax Comparison Table
Tax Dangers
Plans and Scenarios
Evaluating Equity Compensation
What Is Private Stock Worth?
Can You Sell Private Stock?
Stock Option Scenarios
Summary of Dangers
Offers and Negotiations
Why Negotiation Matters
Equal Treatment
General Expectations
Offers
Offers From Startups
Questions Candidates Can Ask
Typical Employee Equity Levels
Typical Startup Advisor Equity Levels
Negotiation Tips
Offer and Negotiation Dangers
Documents and Agreements
Further Reading
General Resources
Considerations for Founders
Considerations for Candidates and Employees
Types of Equity Compensation
Taxes
Vesting and Expiration of Stock Options
Negotiation
Forms and Tools
Disclaimer
Credits
Please Help!
License

Remote Work

What’s Inside

Part I
Foundations
Remote Work Benefits
Remote Work Myths and Pitfalls
Practices of Successful Remote Teams
Remote Company Culture
Part II
Working Together When Apart
Key Channels and Tools for Remote Communication
Remote Collaboration Ground Rules
Staying Aligned Across Remote Teams
Remote Team Agreements and Protocols
Making Decisions Remotely
Remote Meetings
Handling Urgent Issues Across Remote Teams
Part III
Managing Distributed Teams
Compensation for Remote Employees
Onboarding Remote Employees
Remote Team Integration
Remote One-on-One Meetings
Goal Setting and Feedback for Remote Teams
Morale, Mental Health, and Burnout in Remote Teams
Sharing Difficult News with Remote Teams
Part IV
Being A Successful Remote Worker
Key Strategies for Remote Working
Skills for Successful Remote Work
Setting Up Your Remote Office
Being Professional When Working From Home
Personal Health for Remote Workers
Part V
Legal, Tax, and Operational Concerns
Hiring Remote U.S. Employees
Hiring Remote International Employees
Appendices
The Ultimate Remote Work Tools Landscape
Disclaimer

Technical Recruiting and Hiring

What’s Inside

Part I
Foundations
Do You Need to Hire?
Principles
Cast of Characters
Overview of the Hiring Funnel
Part II
Diversity and Inclusion
What Is D&I?
D&I in Hiring
D&I Myths and Pitfalls
Improving D&I in the Hiring Process
Part III
Internal Alignment
Defining Roles
Setting Levels and Titles
Compensation
Hiring Plans
Job Descriptions
Part IV
Connecting With Candidates
How To Read a Resume
Candidate Sources
First Conversations
Part V
Interviewing
Conducting Interviews
Preparing Interviewers
Technical Interview Formats
Technical Interview Questions
Nontechnical Interviewing
Best Practices for Interviewers
Evaluating Interviews
Legal Considerations for Interviewers
Part VI
After the Interviews
Checking References
Making a Decision
Extending an Offer
Appendices
Appendix A: Decision-Making
Appendix B: Communicating Your Brand
Appendix C: D&I Reading List
Appendix D: Tools and Products
Disclaimer

Founding Sales

What’s Inside

Part I
Foundations
Sales Narrative and Product Marketing Basics
Early-Stage Sales Materials Basics
Part II
From Lead to Sale
Prospect Outreach and Demo Appointment Setting
Early Inbound Lead Capture and Response
Sales Pitches For Startup Founders
Down Funnel Selling
Part III
Customer Success
Mechanisms for Customer Success
Support Sites and Asynchronous Support Materials
Learning From Your Customer Success Team
Customer Success Role Specialization
Part IV
Scaling Sales at Your Startup
High-Impact Sales Hiring
High-Impact Sales Onboarding and Training
Conclusion: Where Do You Go From Here?

Reading with Holloway

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Reallyenjoyinghowwell-writtenandinformativethe@hollowayguidesare.Finishedthe“GuidetoTechnicalRecruitingandHiring”and“EquityCompensation”andIcantotallyrecommendthem.
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About the Authors
Andy Sparks
The Holloway Guide to Raising Venture Capital
Andy Sparks is an executive coach to startup leaders, a writer, and an entrepreneur. He is the former CEO of Holloway, a digital book publisher, and the former COO of Mattermark, a business analytics and database company used by venture capitalists to source deals. In his career as an entrepreneur, he raised more than $20M in venture capital. Andy felt it was important to write this book after having moved to Silicon Valley from Ohio without a network, as he pieced together how fundraising works from hundreds of conversations, hours of internet searches, multiple $900 sessions with lawyers, and a slew of other books. He hopes his writing can give founders the tools to make decisions that are good for their businesses, their teams, and themselves.
Joshua Levy
The Holloway Guide to Equity Compensation
Joshua Levy is co-founder of Holloway, a digital publishing startup. He has authored and edited online works in business and engineering that have reached over a million readers. Josh has built software and led technical teams in Silicon Valley for 15 years at BloomReach, Cuil, Viv Labs (sold to Samsung), and SRI (on the technology that led to Siri). His interests include typography and design, knowledge and collaboration systems, AI, web search, cloud infrastructure, and open source.
Joe Wallin
The Holloway Guide to Equity Compensation
Joe Wallin is a Seattle-based corporate lawyer who represents startups, investors and lenders in startups, founders, and executives. Joe has been working in the early-stage company space since the late 1990s. He is a member of the Angel Capital Association’s public policy advisory council, where he is actively involved in trying to make the law better for investors and founders. Joe has written for The Wall Street Journal, PandoDaily, GeekWire, and Xconomy, and blogs at The Startup Law Blog.
Katie Wilde
The Holloway Guide to Remote Work
Katie Wilde is VP of Engineering for Buffer, a globally remote company with 90 teammates in 19 countries.
Juan Pablo Buriticá
The Holloway Guide to Remote Work
Juan Pablo Buriticá is a software engineering leader who has built and led distributed teams for over a decade. He leads the LatAm Engineering organization at Stripe, focused on building financial infrastructure in the region. Juan Pablo has built high-performing software engineering organizations by emphasizing Open Source software values, technical excellence, trust, and empathy. He has also organized more than 10 software engineering conferences in the U.S. and Latin America, founded multiple JavaScript meetups, and led the growth of Colombia’s JavaScript community, now one of the largest Spanish-speaking JavaScript communities in the world. He is originally from Bogotá, Colombia and lives in New York City.
Osman (Ozzie) Osman
The Holloway Guide to Technical Recruiting and Hiring
Osman (Ozzie) Osman is co-founder and head of engineering at Monarch Money. He has built products and engineering teams at companies including Quora and Google. Ozzie has also started two companies that have been acquired, and advised dozens of other startups. He is the lead author of the Holloway Guide to Technical Recruiting and Hiring.
Pete Kazanjy
Founding Sales
Pete Kazanjy is a serial founder, and seasoned early stage SaaS executive, advisor, and investor. Pete founded TalentBin, a category-defining talent search engine and recruiting CRM, which exited to Monster Worldwide in early 2014. Pete currently is the founder of Atrium, a proactive sales performance analysis solution. At TalentBin, Pete went from product and product marketing founder generalist, to first sales rep, first sales manager, first VP of Sales, all the way to leading new product sales for 600+ sales reps at Monster worldwide. Pete also founded and runs the canonical invite-only nationwide sales operations and management peer education community Modern Sales, featuring 13,000+ members from a who’s who of sales operations, enablement, management, and leadership from 5k+ leading sales organization’s. Additionally, Pete is a well known expert in early stage go-to-market and “founder selling”—helping organizations figure out their early critical positioning and selling activities. He has done substantial speaking and writing on the topic, including being a frequent contributor to First Round Review and Saleshacker, and advises a number of enterprise software companies on establishing and optimizing their sales and success motions.

Read with Holloway

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

Definition A job requisition (or job requisition form) is an internal company document a manager uses to formally request permission to fill a role or position. These documents are particularly useful for coordination and wider alignment at larger companies. For instance, the requisition might require approval (often from finance, HR, and upper management) to ensure sufficient space and funding are available for a new hire. Once the requisition receives the necessary approvals, it can serve as the starting point for a discussion between the hiring manager and their designated recruiter (for instance, at a role intake meeting).

Powerful Search Features

Screenshot of the search window

Pitfalls and Confusions Explained

danger️️ Wording in your job description can have unintended consequences in determining who applies. Attempts to make your roles sound more enticing can actually discourage people from applying. Researchers have found evidence that using gendered language contributes to an imbalanced pipeline of candidates; certain language can also discourage older candidates or candidates from marginalized communities from applying.

confusionPeople often confuse percentiles and percents, with serious consequences. When someone recommends compensating at the 75th percentile, they are talking about percentile rank, or paying at a rate that is greater than what 75% of companies pay for a role (in a given market, stage, et cetera). This is very different from paying 75% of what a fair market salary would be.

controversyThe “best” interview format for coding questions is a notoriously controversial topic. While many companies rely primarily on onsite, face-to-face coding interviews, a significant fraction of engineers consider “whiteboard coding” to be intimidating, stressful, and not predictive of job performance. On the other hand, alternatives like take-home tasks have drawbacks as well.

Visual Presentations

Get the Bundle

All Five Guides, Lifetime Access, One Price

The Holloway Startup Foundations Bundle

Five essential guides for early startups covering fundraising, equity, hiring, growth, culture, and sales. Comprehensive knowledge from top startups leaders.

Researched, written, and edited by experts.

Written by practitioners. Edited by professionals.

Original Author — Raising Venture Capital
Andy Sparks
Contributing Authors — Raising Venture Capital
Rachel Jepsen
Contribution and Review — Raising Venture Capital
José 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)
Original Authors — Equity Compensation
Joshua Levy (Holloway)
Joe Wallin (Carney Bradley Spellman)
Contributions and Review — Equity Compensation
José Ancer (Egan Nelson LLP)
Michael Brown (Fenwick & West)
George Grellas (Grellas Shah LLP)
Zach Holman
Chris McCann (Greylock Partners)
Leo Polovets (Susa Ventures)
Eric Tyson
Review — Equity Compensation
Soona Amhaz (Token Daily)
Praveen Boda (Innoviti Payment Solutions)
Zach Boerger (Drive Capital)
Kara Egan (Emergence Capital)
Tom Eisenmann (Harvard Business School)
Michael Fitzgerald (Submittable)
Daniel Gulati (Comcast Ventures)
Nikhil Gupta (HiDimensional)
Tammy Han (Emergence Capital)
Travis Hedge (Co-founder)
Ina Herlihy (Walmart)
Kelsey Hunter (Paloma)
Francis Jervis (Augrented)
Xuezhao Lan (Basis Set Ventures)
Tracy Lawrence (Chewse)
Kevin Lee (New Food CPG Co.)
Christina Li (Cisco)
Yijen Liu (Absorb)
Amit Mukherjee (New Enterprise Associates)
Pradeep Muthukrishnan (HiDimensional)
Jennifer Neundorfer (Jane VC)
Anthony Pompliano (Morgan Creek Digital)
John Sechrest (Seattle Angel Conference)
Shiju Thomas (Relay Hill Capital)
John Sechrest (Seattle Angel Conference)
Anita Umesh
Ryan Walsh (Splice)
Tiffany Zhong (ZebraIQ)
Lead Authors — Remote Work
Katie Wilde (Buffer)
Juan Pablo Buriticá (Stripe)
Contributing Authors — Remote Work
Haley S. Anderson (Just Security)
Paul Maplesden
Paul Millerd (Boundless)
Courtney Nash (Holloway)
Steph Smith (Integral Labs)
Contribution and Review — Remote Work
Greg Caplan (Remote Year)
Toni Cowan-Brown (Protocol)
Matthew Damm (Fenwick & West)
Ryn Daniels (HashiCorp)
Stephan Dohrn (Inside Out Coaching)
Rodolphe Dutel (Remotive.io)
Ben Erez
Laurel Farrer (Distribute Consulting)
Joe Giglio (Chief Remote Officer)
Bud Hennekes (A Boundless World)
Andreas Klinger (AngelList)
Morgan Legge (Convert)
Brenna Loury (Doist)
Darren Murph (GitLab)
Kristen Pavle (Ponder)
Dan Pupius (Range)
Hiten Shah (FYI)
Jonathan Siddharth (Turing)
Dave Smith (Packet)
Kevin Stewart
Luke Thomas (Friday)
Job van der Voort (Remote.com)
Kathleen Vignos (Twitter)
Judy Williams (The New Stack)
Jay Yuan (Turing)
Additional Thanks — Remote Work
Sophia Bernazzani (Owl Labs)
Darren Buckner (WorkFrom)
Frank Chen (Slack)
Matthew Gregory (Ockam.io)
Jody Grunden (Summit CPA Group)
Nathaniel Hemminger
Liam Martin (Running Remote)
Lauren Moon (Atlassian)
Jeff Morris, Jr. (Lambda School)
Oliver Starr (Turing)
Anita Umesh
Original Author — Technical Recruiting and Hiring
Osman (Ozzie) Osman (Monarch Money, formerly Quora and Google)
Contributing Authors — Technical Recruiting and Hiring
Aditya Agarwal (formerly CTO, Dropbox)
Alex Allain (Dropbox)
Jose Guardado (Alpha Talent)
Jennifer Kim (Inclusion at Work, formerly Lever)
Aline Lerner (Interviewing.io)
Joshua Levy (Holloway)
Viraj Mody (Convoy)
Kevin Morrill (formerly Mattermark)
Jason Wong (JWong Works)
Scott Woody (formerly Dropbox)
Contribution and Review — Technical Recruiting and Hiring
Laurie Barth (Gatsby)
Juan Pablo Buriticá (Splice)
Joe Cheung (Craft Ventures)
David Connors (Sequoia Capital)
Ryn Daniels (HashiCorp)
Tammy Han (Emergence Capital)
Robert Hatta (Drive Capital)
Zack Isaacson (Sweat Equity Ventures)
Kellan Elliott-McCrea (Dropbox)
Pradeep Muthukrishnan (TrustedFor)
Benjamin Reitzammer (Freelance CTO)
Aaron Saray (More Better Faster)
Dave Story (Next Level Leadership)
James Turnbull (Glitch)
Jon Volk (Unusual VC)
Sam Wholley (Riviera Partners)
Review — Technical Recruiting and Hiring
Dan Abel (Tes)
Bernard Liang (Door Dash)
Dobromir Montauk (Doxel.ai)
Greg Morris
Cosmin Nicolaescu (Brex)
Darshish Patel (Shopify)
Ashish Raina (Optimize Talent)
Dan Rummel (One Medical)
John Schmocker (Soma Talent)
Harj Taggar (Triplebyte)
Sherwin Wu (Opendoor)
Joe Isaacson (Facebook)
Jean-Denis Greze (Plaid)
Production
Haley AndersonResearch and definitions
Rachel AndrewEditor
Jennifer DurrantDesign
Carly GillisEditor
Hope HackettSwiss Army Knife
Vahe HovhannisyanGraphics
Rachel JepsenEditor
Dmitriy KharchenkoGraphics
Joshua LevyEditor
Sakhi MacMillanCopyeditor
Courtney NashEditor
J. Marlow SchamauderCopyeditor
Andy SparksEditor
Leigh TaylorGraphics
Nick StoverGraphics
Titus WormerPrint engineering

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