The Holloway Modern Work Library

An extensive and carefully curated set of resources for entrepreneurs, employees, and investors.


Updated December 16, 2019
Original Author
Andy Sparks
Courtney Nash
Haley S. Anderson
Contribution and Review
Tom Eisenmann (Harvard Business School)
Brian Weisberg (Tidelift)
Luke Thomas (FridayHQ)
Nadia Eghbal (Protocol Labs)
Dasha Maggio (Felicis Ventures)

Startup Boards

To create this Holloway Syllabus, we put in more than 20 hours of research and worked with Tom Eisenmann from Harvard Business School and Brian Weisberg from Tidelift to pull together and vet great resources. We believe this is the most comprehensive and authoritative list (over 100 resources!) to help you master the ins and outs of startup boards.


Despite the good intentions and great experience in the room, the painful truth is that precious time and energy is frequently squandered by directors and startup CEOs.Jon Callaghan*

A great board will help founders discern the difference between decisions that can kill the company like a snakebite and those that merely look like snakes, but are just piles of rope that can be untangled. A bad board will be a snake itself. The trouble is, even repeat founders have little experience with boards. Fewer have experience with well-run boards. Investors often have the benefit of sitting on multiple boards and hold positional power relative to founders, who rely on the nebulous, everything-but-guaranteed necessities of networking, mentorship, and luck in finding a helpful investor. More often than not, when faced with a crisis or question, they Google it.

We’ve organized the content in this Syllabus to help you move from a 1 to a 2 or a 5 to a 6 on the Urban scale, Wait But Why creator Tim Urban’s metric to measure expertise (1 is “never heard of the idea”; 10 is “world’s leading expert”). This Holloway Syllabus provides readers a list of resources that cover startup board basics (“what is a board?”) to complex, on-the-ground challenges (“how do I set up different committees as my board grows?”), and everything in between.

Startup Boards 101

What is a board?

A board of directors (board or BOD) is a group of people who oversee an organization, including by guiding and supervising the organization’s officers, and have legal obligations to act in the organization’s best interest. For a corporate board of directors, this includes ensuring that the company serves the best interests of its shareholders. All corporations are legally required to have a board of directors. The board typically consists of a mix of individuals representing different interests. An inside director is any founder, executive, or individual investor on the board. An outside director is not an employee of or existing investor in the company, and they are recruited to the board to provide specific expertise. Individuals on the board are referred to as board members. A board member is said to have a board seat at the company.*

When a company incorporates, the board is usually made up only of one, some, or all of its founders. Under Delaware corporate law, boards have the authority to control the day-to-day matters in a company. You should always defer to your legal counsel when determining what decisions need a board vote, but in our section on protective provisions, we cover the decisions that almost always require a board vote.*

It’s rare for an investor to negotiate a board seat at the seed stage unless they’re writing a large check ($750K+). Boards of directors usually meet quarterly for meetings that can be as long as three hours; they’re a big commitment, and investors usually don’t want to sit on too many boards. But at some point beyond the seed stage, you’ll have to give up board seats to investors, and that means you’ll need the support of any investors with a board seat when making major decisions.*

What does a board do?

When a startup forms a board of directors, the primary role of the board is to make key strategic and operational decisions for the company. The board typically holds regular three- to four-hour board meetings. These are often held quarterly or every six weeks; when a company is young they could be held monthly. In these meetings, the board discusses progress, goals, challenges, key hires, and all sorts of operational issues. A board meeting is used to align the operations with the interests of the investors and founders. While board meetings are often viewed as a tool for investor oversight, they are very much also about entrepreneurs seeking the board’s counsel and advice.*

Do I need a board?

Board Composition

Structure and roles

Putting together a board

Should you grant board observer seats?

When to add directors or grant board seats

Sitting on other boards

Board Meetings

Preparing for a board meeting

The board package

Board meetings

Board and Investor Communication

Board communication

Investor updates

Resources for Startup Boards





Case studies

B2B Sales

To create this Holloway Syllabus, we put in more than 40 hours of research and worked with Tom Eisenmann from Harvard Business School to pull together and vet great resources (Tom credits Frank Cespedes at HBS for helping him). We believe this is the most comprehensive and authoritative list (over 100 resources!) to help you master the ins and outs of B2B sales.


Two salespeople may see exactly the same characteristics in a customer, but the successful one will spot the characteristic that matters above all others and establish a sales strategy accordingly.Philip Delves Broughton, The Art of the Sale, p.32*

When you’re new to sales and ready to learn, where do you begin? Whether you’re a founder who needs to figure out how to make the business work, someone who thinks they might make a great salesperson, or an employee curious how the sales department affects the rest of the company, it can be a struggle just to get started. First of all, sales is a complex topic, lingo-heavy and full of acronyms. Even when it comes to the kinds of sales you could research, there’s subtopic after subtopic: inside sales, outside sales, channel sales, direct sales, enterprise sales, and on and on. Googling can get you nowhere when you don’t even know the right words to search for.

Our goal in creating this syllabus is help people with no to some knowledge on the subject of B2B sales familiarize themselves with common sales parlance, and learn key sales concepts and strategies.

A lot of the resources in this syllabus focus on software sales, but the principles and concepts are relevant to folks who sell all kinds of things, from hardware to services. We cover everything from the very basic (“What is B2B sales?”), to methodologies, hiring for sales positions, resources for joining sales communities, newsletters and podcasts, and more.

B2B Sales 101

What is B2B sales?

Do I need a B2B sales team?


Overview of the sales process

General sales tips

Sales strategy

Getting started

How sales organizations evolve

Choosing a sales model

Sales methodologies

Inside sales

Channel sales

Scaling sales

Managing conflict with sales and other functions

Specific sales tactics


Sales hiring

Hiring sales senior management—who and when to hire

Hiring, managing, and motivating sales teams

Resources for B2B Sales


Books on sales for sales people

Books on sales strategy

Books on sales methodologies

Books on sales for everybody


Newsletters and blogs


Case Studies

Remote Work

To create this Holloway Syllabus, we put in more than 30 hours of research and worked with over 20 people with a range of experience with remote work. We believe this is the most comprehensive and authoritative list (over 120 resources!) to help you master the ins and outs of remote work.


“Successfully working from home is a skill, just like programming, designing or writing. It takes time and commitment to develop that skill, and the traditional office culture doesn’t give us any reason to do that.”—Alex Turnbull, CEO of Groove*

Depending on who you ask, remote work is either the Future of Work, or a trend that’s mostly a time-sink for employers and boondoggle for their employees. It’s also not clear what exactly remote work is. Is it Mary in Accounting working from home a couple days a week, that startup that claims to have “no management levels or titles” and never opened a physical office, an old school conglomerate with offices all over the globe, or that “digital nomad” guy who set up his temporary workspace at an entire table in your neighborhood coffee shop? It’s all those things (and more), which can make it hard to get your arms around how to undertake and manage it as a business leader or manager, or how to find and succeed at a remote job as an employee.

Our goal in creating this syllabus was to help people with zero to some knowledge on the subject of remote work and distributed teams learn key concepts and strategies, and familiarize themselves with the benefits, pitfalls, and unexpected side-effects (like when remote employees in foreign countries have to be independent contractors).

A lot of the resources in this syllabus focus on the benefits and challenges for remote workers and the companies they work for, but the principles and concepts are relevant to anyone who is interested in better understanding what distributed teams mean for the future of work. We cover everything from the very basic (“What is remote work?”), to common pitfalls, suggested coping mechanisms for employees and best practices for companies, plus newsletters, podcasts, and more.

Remote Work 101

What Is Remote Work?

Is It Just Hype, Or A Real Thing?

The Great Productivity Debate

Research and Reports

Hiring and Managing Remote Teams

Building a Remote Culture

Collaboration, Communication, and Tools

Remote Work Pitfalls

Employment Laws, Taxation, Payroll, and International Considerations

Company Stories

So You Want to Work Remotely

Productivity and Office Setup




Digital collections


Interviews and talks


Company Culture

To create this Holloway Syllabus, we put in more than 40 hours of research and worked with Tom Eisenmann from Harvard Business School, Nadia Eghbal from Protocol Labs, and Dasha Maggio from Felicis Ventures to pull together and vet great resources. We believe this is the most comprehensive and authoritative list (over 230 resources!) to help you master the ins and outs of company culture.


"Culture is the tacit social order of an organization: It shapes attitudes and behaviors in wide-ranging and durable ways. Cultural norms define what is encouraged, discouraged, accepted, or rejected within a group. When properly aligned with personal values, drives, and needs, culture can unleash tremendous amounts of energy toward a shared purpose and foster an organization’s capacity to thrive." Boris Groysberg, Jeremiah Lee, Jesse Price, and J. Yo-Jud Cheng, The Culture Factor*

The concept of “company culture” often seems to be something between a buzzword, an enigma, and a feeling, so what is it really? Company culture is an expression of shared values, a reflection of leadership, the way colleagues relate to and treat one another, a sense of safety and belonging, a question of how a company reacts to the challenges it faces, and more. As demonstrated by the resources in Why does company culture matter? and the case studies in The Risks of Getting Culture Wrong, company culture can be a source of profitability and a reason excellent employees stay, or it can lead to wrongdoing, disaffection, and even criminal investigation.

This syllabus draws together resources that will help you learn about the many dimensions of company culture, as well as tips and tools that can help you build, change, and scale your own. While all of its sections could easily expand into their own deep dives, we have selected key resources that will give you the overview you need to grapple with the main concepts and controversies in each. If you work at a company, are thinking of starting a company, or even just interact with others, this syllabus is for you.

Company Culture 101


What is company culture?

Why does company culture matter?

Elements of Company Culture


What are company values?

How are values put into action?

Organizational structure

Why does structure matter?

What kind of structure should you have?

Good leadership

Leaders' impact on culture

Positive leadership qualities

Developing leaders




Communication roadblocks

Effective feedback loops

There’s a lot of good advice out there on how to give feedback effectively. We consider this a net positive. That said, readers may find it more daunting to read each and every one of these resources, and we suggest that you take a look through, focusing now on any that apply to particular situations in which you find yourself and returning to this list as you face new challenges or seek to grow.

Communicating about company culture

Trust and empathy


For more in-depth discussions on diversity and inclusion, check out the Holloway Guide to Raising Venture Capital ("Bias and Discrimination in Fundraising") and the Holloway Guide to Technical Recruiting and Hiring ("Part II: Diversity and Inclusion in Tech" and "Appendix B: Diversity and Inclusion Reading List").

Why inclusion matters

  • Tech Leavers Study — Kapor Center for Social Impact — Finds that “unfair treatment is the single largest driver of turnover affecting all groups, and most acutely affects underrepresented professionals.” Recommends that “diversity and inclusion initiatives can improve culture and reduce turnover—if they are done right.”
  • Delivering through diversity — Vivian Hunt, Lareina Yee, Sara Prince, and Sundiatu Dixon-Fyle (McKinsey & Company) — demonstrating that gender and ethnic diversity are clearly correlated with profitability
  • The one startup debt you can’t pay back — Phin Barnes — Describing the risks of diversity debt
  • loginDiversity Doesn’t Stick Without Inclusion — Laura Sherbin and Ripa Rashid

Building an inclusive culture

Tools for promoting inclusion

Goal setting

Meeting challenges

Managing conflict

Growing from mistakes

Building and Scaling Company Culture

Building a company culture

Scaling a company culture

Pitfalls in establishing and expanding company culture

Joiners and Leavers

Hiring and retaining

For more information on hiring for technical roles, take a look at the Holloway Guide to Technical Recruiting and Hiring.

Hiring for “culture fit”

Alternatives to “culture fit”


When and why to fire

How to fire

Replacing key leadership

Office Space

To open plan or not to open plan?

Company Culture and Distributed Teams

If you’re interested in distributed teams, check out Holloway’s Syllabus on Remote Work. The full Holloway Guide to Remote Work will publish in Spring 2020. To get an exclusive discount on the Guide, join our waitlist!

Remote teams

Working with contractors

The Risks of Getting Culture Wrong

Case study: GitHub

Case study: Uber

Case study: Volkswagen

Case study: Wells Fargo

🐉 Hic sunt dracones

We’ve included articles here that you might see cited for their takes on organizational culture. We’re sure the authors have the best intentions, but we’ve found their advice to be counterproductive. In particular, we recommend that readers think twice before asking colleagues or employees to work for equity only, at all hours, in explicitly non-diverse cultures, and so on. Such expectations can undermine an inclusive culture.

Further Resources

Reference cases


Books on collaboration and empathy

Books on leadership

Books on values


Free tools

Finding a Co-Founder

To create this Holloway Syllabus, we put in more than 30 hours of research to pull together and vet great resources. We believe this is the most comprehensive and authoritative list (over 90 resources!) to help you master the ins and outs of finding a startup co-founder.


Ideas can pivot and evolve as they grow, funding can always be found somewhere else, the market will always change with a never-ending supply of competitors. But the team that brings it all together forms the company’s DNA.Jonathan Chan, “The Ultimate Guide To Creating The Perfect Founding Team“*

Spoiler alert: Founding a company is demanding. You need not only the idea but an enormous range of skills to turn it into something real. Creating a successful startup requires almost unimaginable amounts of time. It demands drive and grit. It certainly causes stress, sometimes outright depression, and it can take a toll on your personal relationships. Do you really want to do it alone?

For many, the answer is working with a co-founder. A co-founder can lessen the burden in many ways, but this arrangement has its own challenges. What makes someone the right person? Where do you find them? How many co-founders should you even have? When you’ve found your person, what details do you need to agree on? How do you avoid nasty disputes down the road? Should you have a co-founder at all? Read on for answers to these questions and more.

Co-Founding Overview

If you don’t read (or watch) anything else on the topic, take a look at these.

Are You Ready to Found a Startup?

Exercises for answering the question

What it takes

Do You Need a Co-Founder?

Not necessarily

Co-founder pros

Co-founder cons

How Many Co-Founders Do You Need?

Choosing the Right Co-Founder

General advice

Shared values and complementary skills


For non-technical founders

For technical founders

The Logistics of Finding a Co-Founder

Key Conversations

How do you split equity?


contribute Beyond the Usual Suspects

Many of the resources in this section were written by people from a similar privileged background. The challenges of finding a co-founder may be very different for people who face additional barriers, particularly those who have been historically barred access to certain networks. We are actively seeking to publish more perspectives on this topic; if you’d like to talk please reach out. And if we’ve missed anything major in this syllabus, we hope you’ll let us know!

Further Resources


  • bookHatching Twitter — Nick Bilton — A cautionary (and somewhat gossipy) tale about co-founder conflicts
  • bookCreativity, Inc. — Ed Catmull and Amy Wallace — Especially chapter 2, “Pixar is Born,” which tells the story of how the three Pixar co-founders found each other and decided to go into business
  • bookFounders at Work: Stories of Startups' Early Days — Jessica Livingston — Interviews with thirty-two founders of successful businesses, including many co-founders
  • bookCofounding the Right Way — Jana Nevrlka
  • bookThe Founder’s Dilemmas — Noam Wasserman — Tradeoffs founders confront when deciding when/with whom to found, how to split equity, how to divide roles, etc.

Interviews with co-founders

Communities for founders

Co-founder services and opportunities

Disclaimer: Holloway has not tested these services and cannot speak to their quality. But since you’re already here, we thought we could save you a Google search.

Joining a Startup

To create this Holloway Syllabus, we put in more than 40 hours of research to pull together and vet great resources. We believe this is the most comprehensive and authoritative list (over 90 resources!) to help you master the ins and outs of joining a startup.


Regardless of what stage startup you join, the choice should be just that—something which you chose, a deliberate selection based on criteria that you’re optimizing around and the potential of upside, not a perception about safety. You should be joining a startup because of your excitement about the role/situation, the company itself, and the opportunities ahead with the chance to change the world. David Beisel, “Start with When”*

Startups come in a lot of shapes and sizes, and stability and success are not at all guaranteed. The choice of which startup to take a job at can be the difference between a fulfilling period of growth, respect, teamwork, and even financial gain versus a period of crushing stress, interpersonal conflict, and failure. So how do you choose a startup to work for—and how do you know if the startup path is right for you?

The good news is that successful startup employees, founders, and scholars have done a lot of the foundational thinking for you when it comes to joining a startup. They’ve written and spoken about whether you should join a startup at all, and which one to join if you choose to do so. They’ve offered advice on getting hired and what to do after that. They’ve shared stories of their own successes and failures. And we’ve organized it here. While you can’t eliminate risk in your decision entirely, we believe it’s worth putting in a few hours of reading to make a better decision that’ll effect the next few years of your life, and even your whole career.

If you take that time and decide joining a startup isn’t for you, that’s one more data point you can now work with. And a lot of this knowledge will translate to decisions you have to make down the road. As Anand Chopra-McGowan points out, everyone can learn from startup employees—how they find their positions, how they adapt, how they manage their time, how they communicate with managers. This is a new way to think about your work, expand your skills, and decide what’s right for you.

Do You Want to Join a Startup?

Startup downsides

Founding vs joining

The decision making process

Which Startup Should You Join?

If you’re interested in thinking more deeply about the right company for you, we encourage you to check out the “Candidate-Company Fit” section of The Holloway Guide to Technical Recruiting and Hiring.

Getting Hired at a Startup



Negotiating Compensation

Succeeding Once You’re There

Dealing with uncertainty


Curiosity and self-learning

Management skills

Managing yourself

Managing up

Taking care of yourself

If you are experiencing anxiety, depression, or other signs of burnout, we hope you will reach out to a mental health professional. We have collected some resources below.

Further Resources


Podcast episodes

Blogs and newsletters

Job boards

There are tons of job boards while you’ll find listings for work at startups! If you’re just getting started, you might consider checking some of these out.

Mental health resources