This Guide is for anyone who writes, edits, or otherwise contributes to a Holloway Guide. It is intended to ensure consistency, accuracy, and brand voice of all Holloway Guides and related content.
To assemble and publish reliable knowledge from experts for all to learn from and build on. You can read more here.
We write for an audience that is 100% intelligent and also 100% naive about the topic at hand.
Our editorial principles are:
To offer helpful guidance
…with long-term value
…that is trustworthy
…and accessible.
Our aspiration in writing Guides is that they be both deep and engaging. Technical and accessible. We want to earn respect from both experts and beginners. The voice and tone we use are critical to striking this balance.
At Holloway, we’ve paced the halls of many a company large and small in our readers’ shoes—we know that modern work is fraught with endless choices and the tool of record for navigating those choices (searching Google) yields questionable results at best. The Holloway voice is that of a trusted friend sitting across from our reader over coffee. The trusted friend of our reader has years of experience, but is not an “expert” removed from our reader by multiple degrees and decades of experience. While the trusted friend harnesses the knowledge of experts, they are perhaps only two or three years ahead of the reader. They can remember what it is that motivates the reader and what scares them; they understand the anxieties with which the reader approaches a topic or problem; they get that a reader might be urgently trying to figure out some course of action, but they also know the reader would love to delve into all the nuances of a topic, given the time.
Our voice wants to converse, not just drop information into the vessel of a reader. That’s not what you do to friends! But our friends really, really want to move from a 2 or 3 on Tim Urban’s Scale for understanding complex ideas to a 7 or 8—someone who doesn’t just reiterate popular opinion but can answer expert questions and reconcile contradictory thoughts about the idea. Because that’s how they can have better conversations. And they know we can help them with that. With a conversational, trustworthy voice and a fervor for research, we prefer clarity over flowery descriptions, and accuracy over easy answers. We use humor where it can help make our readers feel comfortable with a difficult topic; humor can help people feel like a topic is approachable, like the writing is for them, and like they are part of the conversation.
Here it is broken down:
Rigor. Be accurate, precise, logical, and clear. Avoid oversimplification or glossing over details. Readers come to us often after failing to find trustworthy, comprehensive coverage of something complex. Save the fluff for sandwiches.
Respect. Always respect the reader’s intelligence. Don’t avoid conflicts or messy topics. It’s tempting to hide messy or confusing details from readers, but we must not underestimate people’s ability to manage information when it is supplied well. When there is controversy, give an overview of perspectives, reference the key people or resources on different sides, and give rationale and context. We do offer advice when we strongly believe that readers might be supplied with advice that is bad for them elsewhere.
Clarity. Provide clarity around complex material. Give expert opinions and dispel common confusions. The ability to learn has little to do with how much exposure someone has had to a particular topic in the past. Without oversimplifying details or writing for short attention spans, we aim to intrigue visitors by giving them a clear sense of what we’re going to offer, so that they know if they stick around and keep reading, they’re going to learn something of value.
Directness. Speak directly to the reader. Be genuine.
Warmth. Be empathetic and encouraging. We never tell readers they should already know something, or assume that they come from a particular place, are of a particular age, or have a particular background or level of experience. In fact, we never use the phrase “you should.” We speak to people’s anxieties. We are never thoughtless when using humor, which we do sparingly. Poorly or thoughtlessly executed, “jokes” can alienate, anger, and even do harm. When calling out bad behavior, we always punch up, not down.
Principles of voice will remain true across Guides, articles, social media, and blog posts, while the tone might change depending on the medium and/or audience—whether we’re writing or editing for a Guide, a blog post, an email to customers, or social media. The emotional and mental states of people engaging with these different platforms can vary; while the voice of friendly rigor is the same across all Holloway output, casual humor and slang make more sense on Twitter than they do in a Guide, and personal opinions make a lot more sense in a newsletter than they do in a blog post. We use first-person plural in all our publications and across social media, with the exception of newsletters, which are written by individuals, and definitions, which adopt a more formal tone and do not use the first or second person.
In general, we adhere to the Chicago Manual of Style. Here’s a few key high-level points to consider across all aspects of our content.
We create guides, not books. Avoid any wording along these lines, including:
Book. We prefer Guide wherever possible. Capitalize when using in or as shorthand for an existing title (The Guide to Remote Work), and lowercase when discussing guides in general ("Holloway publishes guides on…")
Chapter. Use section instead.
Edition. This may vary based on context, but likely either version or revision would apply here.
Use active voice. Grammar Girl sums it up best.
Confront jargon. We’re not saying don’t use it, but call it out, and explain its purpose and put it in context.
Be positive and helpful. Except when you clearly shouldn’t. Calling out harmful, negative, pitfall-ridden territory sometimes requires speaking less softly.
Here are a few helpful reminders that should be checked thoroughly for consistency:
An important thing to know about the common comma that can save you loads of agonizing: It’s used to separate, rather than connect. If you’re trying to connect two separate thoughts, you mean to use a semicolon, an em dash, or a colon. This is a useful way to tell if you’re comma splicing, or using a comma to separate two pieces that can stand on their own (otherwise known as independent clauses). Use commas when:
Separating coordinate adjectives, aka, adjectives that cannot be separated by the word _and_, as in: “What a beautiful, thoughtful piece of writing.” “Yes, it is thoughtful and beautiful, how wise.”
Separating the final item in a list. Yep, Holloway uses the Oxford comma! That means that when making a list, put a comma between and and the final item, as in: “Bird, bees, and overwhelming loneliness”
Use them when:
Introducing a list of bullet points or steps (always)
Extrapolating on a point you just made (sometimes)
Introducing a question (sometimes)
Use them when:
Separating the items, which themselves have internal punctuation, in a list, or where using commas in a list would make it hard to follow
There are three types of dashes, the hyphen, the en dash, and the em dash. Most people are familiar with hyphens, but they are often overused. En dashes are mostly structural, and em dashes often present significant challenges. Here’s how we use them:
Hyphen (-) This single, small dash is used to combine words—two or more—that make up a compound adjective, like “well-respected” or “holier-than-thou.” Hyphens do not have spaces around them. Hyphens are also used to combine a prefix with a pronoun, as in “un-American,” but not in regular nouns like “untenable.” You do not need to use a hyphen when the compound adjective you’re looking at ends in –ly, as in “a fascinatingly written article,” nor when the compound adjective follows the noun, as in “the article was well written.” However, “a well-written article” is correct, because the compound adjective precedes the noun. Some compound adjectives, like when they contain more than one verb, will always have a hyphen: “the dish was carry-out” and “a carry-out dish” are both correct.
En dash (–) For our purposes, en dashes are used for two things:
Tip: If you use a Mac, the en dash can be typed as ⌥-
Em dash (—) The em dash is a favorite punctuation at Holloway, because it’s primarily emotional. In most cases, an em dash can be replaced by a comma clause or a set of parentheses and technically the sentence will be correct. But each of these options represents a different emotional register. While a comma clause indicates a piece of information that can be considered equal to the rest of the information in a sentence, and a parenthetical usually contains supplemental, surprising, clarifying, or detracting information, the em dash is used to separate—that’s right—the information in a sentence that you definitely want the reader to notice. They are used to mark a shift in tone or to mark off important information you don’t want anyone to miss. They’re also better to use than a comma in the case that your sentence already has a great deal of commas. We use the em dash a lot at Holloway because it tends to bring a conversational tone to complex constructions containing a lot of information. You’ll notice em dashes throughout this text—you can refer to these if you get confused!
There should never be spaces around an em dash.
Another note on parentheses: they cannot correct the damage of a run-on sentence.
Tip: If you use a Mac, the em dash can be typed as ⇧⌥-
Note: In British written English, the en dash does the work of the em dash, which is hardly used outside the U.S. We just like things bigger here.
Our main use of brackets is to provide or clarify information within a quote that doesn’t appear in the original quote. Say Cynthia is a really cool dancer, and is participating in a dance contest later this month. Angelica wants to tell you (on the record) something about Cynthia: “She will win.” When it turns out that the article you’re writing has more to do with Angelica and in fact you aren’t even mentioning Cynthia’s dance ability, but still want to include Angelica’s line about her, because it just says so much about who Angelica really is, you might do this: “She will win [the dance competition].” Got it?
Note: brackets are also used heavily in Markdown format, such as to format links, but the reader never sees them.
Use them in company names (AT&T) and names of law firms. Do not use them otherwise in text, headings, or section titles.
There is no need to include nonbreaking spaces in ellipses. Holloway’s editorial tool transforms a typed ellipsis into the Unicode ellipsis character.
This refers to normal text, like this, that is neither italicized nor boldfaced. Also known as upright text.
Italics are used for many things, including:
To emphasize or stress certain words or phrases. Italics used for emphasis can often change the meaning of a sentence, and mimic patterns in speech. For example, “Timmy, don’t marry her,” might mean something different than, “Timmy, don’t marry her.”
Book titles
Names of blogs
Newspapers, magazines, and periodicals
Foreign words or phrases
Names of ships
danger If a phrase is italicized, only the punctuation that the phrase contains should be italicized. If a colon or semicolon or comma separates the italicized phrase from further roman text, do not leave it italicized!
We also use italics in the following ways:
When referring to an example of a word rather than a word in context, e.g. “When someone says dilution, what they often mean is…”
People often put examples of words in quotation marks, but this can be confusing if a text already includes quoted material, and it also tends to look quite bulky.
Sometimes, however, it might be more appropriate to put a reference to a word in quotation marks, particularly when referring to the use of jargon.
When quoting within a quote, use single quote marks, like, “He said, ‘I love you,’ but I could hear the air quotes.” Colons and semicolons go outside quotation marks. If the punctuation applies to the quote, put it inside; if it doesn’t, put it outside. We also use quotation marks to offset the following:
Poems
Short stories
Essays
Articles
Boldface is used only in definitions, because they serve a specific function in the product. We’ll explain more in the section on definitions.
Do not use underlining. It’s a typewriter habit and not supported in Markdown or the Holloway Reader. (The Holloway Reader does use underline styling to indicate web links.)
Specific paragraphs (or bulleted items) can be tagged with emoji that express a special meaning. These trigger formatting rules in our product that help call out the type of content visually. The set is extensible but includes:
🔹 Important and often overlooked tip
:danger: Serious warning or danger (where risks or costs are significant)
🔸 A caution, limitation, disadvantage, or quirk
🌪 Controversial topic where informed opinion varies significantly
☝️ Common confusion or misunderstanding, such as confusing terminology
∑ Technical point (arcane or academic and not essential)
📰 New or recent developments
🚧 Expansion or improvement needed (please help!)
These emoji appear at the beginning of a block (“chunk,” usually a paragraph, but sometimes at the top of a bulleted list) of text, never within it. Put a space between the emoji and the first word of the chunk.
Paid and login emoji, as well as media type emoji, do appear in-line, preceding linked text. They should be placed after the first parenthesis containing linked text, with no space between emoji and linked text.
💰 May require payment to read
🔑 May require an account to read
Media types
📈 Slide deck or infographic
🎥 Video
📖 Book or e-book
🎧 Audio or podcast
📥 PDF or form or download
🔨 Interactive online tool
Headings come at different levels: part, section (formerly know as chapter), sub-section, and so on. We refer to these as H1, H2, and H3. These correspond to HTML levels (that is, the actual codes used on websites) as well as Markdown levels (one, two, or more # signs).
H1 = # = part
H2 = ## = main sections
H3 = ### = sub-sections
H4 = #### = sub-sub-sections
In H1 and H2 level, capitalize each word (excluding articles and conjunctions)
At H3 or deeper, do not capitalize after the first word in section headings
We do not want heading levels deeper than H4.
For headings and titles, spell out “and” rather than use an ampersand.
Do not use boldface in headings.
Do not use links in headings.
Italics may be used in headings rarely, such as for titles or foreign words.
Make your headings descriptive and informative (not “Other Ideas”)
Do not have repeated headings across sections (not “Further Reading” in multiple headings)
These are headings which are at the head of a paragraph (not H2 or H3). We often use them to guide the eye where a main heading is excessive, or to label each paragraph in a bulleted list of items.
Boldface inline headings. Avoid inline headings that are plain roman.
Do not boldface the colon, but do maintain other formatting (like italics) with all other punctuation (like exclamation points or quotation marks).
We prefer to use inline headings on paragraphs or most (or all) items in a bulleted list, but not only one or two items in a bulleted list.
Italics should be used when referencing book titles; the names of blogs; article titles; newspapers, magazines, and periodicals.
We do not italicize blog post titles.
We also use italics specific to Holloway in the following ways:
When referring to an example of a word rather than a word in context, e.g. “When someone says dilution, what they often mean is…”
People often put examples of words in quotation marks, but this can be confusing if a text already includes quoted material, and it also tends to look quite bulky.
Use boldface when you really want to offset something important or surprising. It can actually be helpful to do this as you write, because it can alert us to product features and graphic design opportunities we might employ.
Boldface has specific rules in Definitions.
Key statements: It’s also fine to boldface key statements and phrases that guide the eye.
We follow AP style for quoting people in the context of a sentence or paragraph.
Direct quotations
Put quotes around someone’s words you’re quoting in a sentence. According to Rachel Jepsen, “Crackers are like ice. Always get more.”
Conversation
Use the :>: blockquote character to style entire conversations:
Klein: There are many practices in VC that are inherently biased. So this notion of a ‘warm intro,’ and we’ve seen many a famous VC make public statements about ‘if you can’t figure out how to get a warm intro to me…’
Eric Johnson: Screw you, right?
Klein: Yeah, ‘screw you. We don’t want to talk to you.’ Well…
Johnson: You can see that’s very obvious how that would limit the pool of people?
Punctuation
Periods and commas always go within quotation marks.
Dashes, semicolons, question marks and exclamation points go within quotation marks when they apply to the quoted material only. They go outside quotation marks when they apply to the whole sentence.
When you want to highlight a quote to stand out, often at the start of a section or paragraph, use the 🅀 emoji. Be sure to leave a space after the quote, followed by an em-dash and the person’s name:
Famous remarks are very seldom quoted correctly.Simeon Strunsky*
The internet is full of unattributed, un-cited quotes. Don’t add to the noise. We aim for every quote that we include to inspire but also inform. Cite your source, using a footnote whenever possible.
Lists are extremely important to the flow and readability of Guides. We use two types of lists, bullet and numbered.
Use numbered lists only when laying out steps that should be taken in order.
Use bullets judiciously. Key pieces of content that fit together in a narrative way are good as paragraphs.
Bullets and sub-bullets are encouraged whenever there is a laundry list of items, or three or more items fit together in a natural way, or the list may expand in the future via contributions. But they should not be overdone or many levels deep. If you’re writing a paragraph of text followed by another, they likely shouldn’t be bullets.
If the paragraph before the list ends in a colon and the list is an itemization:
start each point with a lowercase letter
don’t punctuate the end of the line
but finish the last piece in the list with a full stop.
If there is no preceding colon, the bullets should each represent a different, separable piece of relevant information that can stand apart from others in the list and still be understood. It may happen that a colon precedes a list of items that are separable and stand-alone.
If your bullet points stand alone, use a capital letter to start each one, and a full stop to end each one.
If every item of a bulleted list has a small inline heading (with a colon), boldface all of them, e.g.:
First item: This is the first example.
Second item: This is the second one.
Third item: This is the third.
Exception: No need to bold lists of subjects under examination, eg. “Hire 1:; Hire 2:”, even if each example is followed by a colon, and especially if the explanatory text contains bolded text like numbers.
Inline links are links that appear within sentences, attached to appropriate words or phrases in the sentence called “linked text” or “anchor text.” This is in opposition to, say, a list of links we might provide in a section like Further Reading.
There are two types of inline links, internal (within a post or Guide, or to another Holloway resource) and external (elsewhere on the web).
Some formatting is the same for both internal and external links:
We refer the most descriptive and logical set of words as anchor text that give a clue to the linked page or linked internal section.
Given that, we recommend shorter anchor text. Long, highlighted links (with mouseovers), especially more than five words or so, tend to be distracting and ugly.
Best practices for anchor text are also guided by how SEO works.
Do not include parentheses in the linked text. If linking to the title of something that has parentheses in it, try rewriting to avoid that construction entirely.
If you are linking to the full name of a book, newspaper or magazine article, include quotes in the link per our citation guidelines. That said, do so judiciously, as this can clutter the text and look messy.
Multiple links should not appear directly next to each other. Except in the case of a list of items where an unlinked comma separates two sets of linked text, spread out multiple links so that they do not appear as one to the reader.
Do not include articles like “a” or “the” in the linked text unless they are part of a full title.
External links serve two main purposes and, depending on their usage, may require different formatting. We provide external links for recommended reading and for citation. In most cases, they are both and can be formatted using appropriate anchor text, described below.
Say less with a link, not more. Rather than citing a source from which the definition of the term stated was derived, this link acts as its own citation, moving a reader to the in-depth resource:
yes“Flat rounds are relatively rare.”
Use actionable words or phrases in a sentence if the action or assertion is the primary point. We prefer the verb or verb phrase over the object alone:
yes“Even if you’re busy, you can get started easily.”
Nouns can work too, optionally including the adjectives or other parts of the phrase, depending on length and clarity:
yesBest: “According to a 2014 New York Times article…”
yesStill good: “According to a 2014 New York Times article…”
In particular, avoid linking in a way that leads the reader to think you’re linking a specific noun:
✖️“Venture is defined by Merriam-Webster as…”
✖️“According to a 2014 New York Times article…”
Avoid using completely generic, self-descriptive anchor text that tells the reader to “read this” or “click here.”
yesAcceptable but not ideal: “For more details, read the full article.”
✖️“An article about this is here.”
✖️Please, never: “Click here to read more about…”
In some cases, links may not be recommended reading (because they are useful primarily as a source for a mentioned fact, but are not themselves recommended or elaborative in a useful way) but are present to provide a necessary citation. When a link is purely for citation, use the footnote option in GoogleDocs, linking it to the piece you wish to cite. Our software will turn this into the appropriate format in the product.
Cross referencing (linking to material that appears in another place within the Guide) is important to the internal discoverability of our content. We call these internal links or “anchor links” (not to be confused with “anchor text”), and they help direct readers to further information on a component of a topic that might be mentioned elsewhere in a Guide.
Linking to internal text is different from linking to external text. If there is a section called “Hello There!” we link to it in markdown [like this](#hello-there). Make sure to follow each of these directions:
Lowercase the text.
Remove everything that is not a letter, number, space, or hyphen (how Unicode is handled).
Change spaces to hyphens.
If a section title is not unique (this is very rare!), add “-1”, “-2”, “-3”, etc. to the link to make it unique.
Rather than link a secondary occurrence of a term to its defining occurrence using an internal link, remember that the mouseover feature will render most links to internal definitions unnecessary. (See Definitions below.)
An internal link should be used when more context is needed or in the case that a reader may want to jump to another section for the answer to a specific question. Use forward links when:
Gesturing to topics covered next, like a roadmap.
Mentioning things that are technically related but were not appropriate to cover. For example, a parenthetical note mentioning how something relates to a topic covered in depth later.
When working in Google Docs, to reference another section within the Guide, simply put a section symbol (§) before the text you want to link. When the document lands, we will manually add in the links using markdown internal linking conventions.
We read and reference a vast amount of information. Where we don’t intend to link to a source for a reader to visit and read, we can cite it instead. Citation has to main uses:
Fair use: To give credit to copyrighted material
To cite facts or statements others have made, like most classic citations
In general, we prefer placing an at the beginning of a link when you are simply including the link as the citation.
You can also format in the Google doc as a normal footnote, for when you want to cite something that is more than a link, such as:
A book, journal, or magazine article
Information you obtained from a direct conversation that is not published anywhere you can point to.
Attribution of a quote
The vast majority of the time, a footnote style citation will simply point to a link: https://www.holloway.com/g/venture-capital
Anything other than that will typically follow this MLA-based general format:
Author Last, First Name. Title of container Other contributors. Version/Edition (if applicable)., Publisher, date, location (if applicable), page number.
Book
Talk
Quoting from an interview (conducted by Holloway)
Quoting from a source, anonymous
A magazine article or something behind a paywall (rare)
Quoting someone from the article:
Just citing the article:
Note: You can also include a link in any of the above citation formats, such as:
Include an acronym (something that can be used as a word, like HUD or FIFA) or initialism (what can’t be pronounced as a word, like FCC or ASPCA) in parentheses following the first full usage of the phrase or title. After that, repeat the full version if enough space in the text has gone by that a person paying a reasonable amount of attention could have forgotten what the acronym stands for. Generally, repeat the full phrase or title if it hasn’t been used in 1,000 words. The exception is any acronyms or initialisms that appear as part of a defining occurrence, meaning they will get mouseovers throughout the Guide and so do not need to be spelled out outside of the defining occurrence.
In definitions, acronyms and initialisms should generally be included as alternate terms, rather than as a defined term in a joint definition.
yeslimited partner agreements: “Limited partner agreements (or LPAs) are contracts that venture firms sign with their limited partners.”
no limited partner agreements, LPAs: “Limited partner agreements are contracts that venture firms sign with their limited partners. These contracts are frequently referred to by their initialism, LPAs.”
However, if a term is primarily referred to by its acronym or initialism and rarely by its full name, the acronym or initialism may be included as a defined term in a joint definition.
yes KISS, keep it simple security: “KISS, which stands for ‘keep it simple security,’ is a free legal document resource for founders and investors provided by the accelerator 500 Startups.”
As a general rule, numbers one through ten should be written out; 11 and up should be numerals. Do not spell out a range, use numerals instead, as in “Create a list of 5–10 people.”
Note: You may see exceptions to this, such as “We’ve seen this happen ten to twenty times.” We don’t yet have a hard and fast rule for this, so if you see it, call it out and we’ll figure out the right usage.
Also, an en dash—not a hyphen—is used to show a range of numbers, as in “9–20.”
If you’re only using numbers below 10, write it out, as in “one through three” or “one to three.”
Money should always be numerical, as in $3M. (Do not spell out to 3 million.)
Never spell out percentages, use the % sign. Percentage ranges should always prefer an en dash, as in 5–10%, with the single % sign at the end. Plus signs and approximate symbols are fine, as in $300M+ or ~$300M.
Thanks to the UNC Writing Center for help with this section.
If you can summarize the data in a figure or table in one to two sentences, do so. If your data are more numerous, providing a figure or table for representation can be helpful and keep text from getting cluttered with numbers.
A table is a columned list of raw data, numbers of text, and is not designed to show the relationship between any variable. Tables should be:
Numbered
Centered on the page and set apart from the text.
Titled, where the title appears on top of the table (Do not rename it if it already has a name.)
Figures are maps, graphs, charts, drawings, or photos. These are what you use when you’re trying to share a conclusion about your data in the form of relationships between variables. Figures should be:
Numbered (e.g. “Figure 1”)
Centered on the page and set apart from the text.
Captioned, with the caption appearing below the figure.
Tip: Keep track of ideas for tables and figures while writing, and share these ideas with your editor. They can work with the engineering team to help produce these.
Definitions are a unique aspect of Holloway Guides and writing, and have their own guidelines, format, and style. They add structure and rigor to the editorial process. They also power features of the Holloway Reader experience, including:
Search results
Mouseovers
Glossary pages
Our goal is to write definitions that are high quality, constantly expanding, and make all of these things possible from the same source content.
The defining block is the one paragraph that introduces a definition. It should include one to three (or so) sentences that define the term for the lay reader. The defining block is arguably one of the hardest things to write because it should be thorough, precise, and brief. For more information on the defining block’s contents, see Elements of a definition below.
Following a defining block, a Guide can have elaborative text (or follow-on chunks) that gives additional context or information about the term that was defined or about its context or placement within that Guide. Elaborative text is specific to a single Guide.
The defining block may appear in multiple places:
Within more than one Guide
On mouseovers
On landing pages
In search results
Elaborative text may appear:
In individual Guides
On landing pages
In search results
Every defined term can have one or more alternate terms. These should introduce the reader to other ways the term is commonly referred to and might include an acronym or initialism of the term being defined, a shortened version, synonyms, or simply an alternate but relevant phrasing. These alternate terms directly follow the defined term in the defining occurrence chunk. They will be supported with mouseover definitions of the defined term if they appear in parentheses, in bold along with the parentheses.
Where there is only one alternate term, introduce an alternate phrase, synonym, or abbreviation with a bold “or”; no “or” is needed if showing an acronym or initialism. Where there are two alternate terms of any kind, simply place an “or” between the terms without any comma.
yes “A capitalization table (or cap table) is a table (often a spreadsheet or other official record) that…”
yes “Annual Percentage Rate (APR) is the total cost per year of borrowing money, including the interest rate, as well as any mortgage points, fees, charges to create the loan itself…”
yes “Angel investors (angels or individual investors) are wealthy individuals who invest their own money directly into companies.”
no “Angel investors (or angels or individual investors) are wealthy individuals who invest their own money directly into companies.”
no “Angel investors (angels, or individual investors) are wealthy individuals who invest their own money directly into companies.”
Sometimes a joint definition is a fine substitute if the words seem different enough.
yes “A founder or entrepreneur is an individual who started a company and now runs that company.”
An acronym or initialism may be presented in a joint definition, rather than as an alternate term, if the acronym or initialism is more commonly used than the full term.
yes KISS, keep it simple security: “KISS, which stands for ‘keep it simple security,’ is a free legal document resource for founders and investors provided by the accelerator 500 Startups.”
Often, only one term will be defined per chunk. But sometimes it makes the most sense to define two terms at once, in contrast or relation to each other. A 🄳 before a chunk that is defining two terms works the same way as with one term. The chunk as a whole, with both terms defined, will come up as a mouseover for either term throughout the text. We call these joint definitions.
If a reader invariably will need to understand both concepts at once (in both directions, meaning both definitions depend on each other), it’s best to have a joint definition. In this example, understanding the terms “shares” or “stock” is impossible without knowing about both.
Two types of joint definitions appear in Holloway Guides. In tiered joint definitions, one defined term can be identified as the primary term while the other terms are subsidiary.
In level joint definitions, no primary term can be identified.
An acronym or initialism may be presented in a joint definition if the acronym or initialism is more commonly used than the full term.
yes KISS, keep it simple security: “KISS, which stands for ‘keep it simple security,’ is a free legal document resource for founders and investors provided by the accelerator 500 Startups.”
The set of all terms, including joint definitions and alternate definitions, is a definition group. A defining block is a paragraph that defines every term in a definition group.
Mouseovers also allow you to visit the defining occurrence by clicking (or tapping) on the mouseover text itself. (What you just saw there is an example of a mouseover for the definition of the defining occurrence!) This is important because a reader is able to get the context of the defining occurrence if they need it. Users will be able to jump to the defining occurrence (and see its surrounding text) and then jump back to where they were (this may be a forward and back button in the browser, though the tooling may change down the road). Otherwise, a reader can simply remind themselves of the definition using the mouseover feature and move on with where they were in the text.
Mouseovers are helpful because sometimes structure dictates that a term be mentioned before being officially defined; other times, a term may not be mentioned again until a dozen pages after it was defined. A forward mouseover occurs over a term that precedes that term’s defining occurrence. A reverse mouseover refers to a defining occurrence from earlier in the text.
A mouseover refers to the definition of a term appearing as you hold your cursor over the term (desktop) or quick-tap the term (mobile) as it occurs throughout the text.
Mouseover matches will be for the longest matching phrase. For example, “ownership interest” would have a mouseover definition but “ownership” would not.
Some terms are formally defined but are so common (“company,” “property”), we configure them to have mouseovers disabled globally.
Sometimes mouseovers may not occur consistently if two different and related multi-word terms occur in context, such as in “public and private company” or “preferred and common stock.” In those instances, only “private company” and “common stock” would get mouseovers. In cases where a reader would expect both terms to have mouseovers, change them to be the complete terms, as in, “public company and private company” and “preferred stock and common stock.”
It’s not always obvious what should be defined as a term. Questions to ask:
Is this an established term with a precise meaning? Then it should be a formal definition. Some ways to tell:
Is the meaning agreed upon by experts? (Usually more than one.)
Is formality about the meaning helpful?
- That is, is it in actual use either by experts *or* in popular
non-expert usage?
- Could we build a definition landing page that people would find
authoritative?
- Would it make sense appearing in a glossary?
Is this a term in popular or expert usage without a precise meaning? Then it should be a conceptual definition. Some ways to tell:
You’d want to see this in the index of a book (or search results), even if the term doesn’t have a formal meaning.
Mouseovers would be helpful, even if the content is an informal definition.
If neither, it’s probably an idea to talk about, but not a formal definition.
Specific examples:
yes:
Anything defined in an existing reference, online or offline.
Any widely popular concept that appears in search results (even if it’s a bit confusing or not the expert-preferred term, we need to make a definition for it).
Anything experts would generally agree is a concept (even if the details are a little murky), it’s best if we do define it.
no:
The exact phrase isn’t found in books or Google results. In this case it’s likely a concept that might be emphasized as a section title or a boldfaced concept, but not a definition.
Things experts may not even agree is a thing.
Things that aren’t defined formally can still be discussed!
What do you do if something doesn’t make the cut but still “feels” like a term? Options:
Inline headings (typically boldfaced items before a list of bulleted items)
Incidental terms (italics), optionally with a link
Boldfaced phrase inside a paragraph to highlight a key idea or phrase
DefinitionThe defining block begins with the character, followed by defining text, which delivers the essential meaning of the term and introduces the term in boldface, with alternate terms as appropriate. In most cases, the defining text for each term should be contained within a single, grammatically appropriate sentence. In joint definitions, defining text should be provided for each term. In level joint definitions, preliminary defining text, which provides a shared definition for the two terms, should appear at the beginning of the defining block before the defining text for any individual term.
The paragraph continues with additional text, which fills in context, details, and other indispensable information that goes beyond the defining text but is still important enough to be mentioned right away.
Essential resources and sources should be included throughout the defining and additional text as appropriate. Include external links to highlight indispensable reading. Include footnotes to cite sources. However, we prefer not to use external links in the defining sentence, notably to other definitive sources (e.g. Wikipedia or Investopedia). Our definitions should be authoritative, complete, and stand on their own.
yes “The Safe currently includes four versions, which differ on valuation cap, discount, and convertible securities, plus an optional pro rata side letter.”
yes “In the context of venture capital term sheets, VCs are often majority shareholders while founders are minority shareholders.*”
DefinitionIt is very helpful to have the readily available to you! Bring up the emoji keyboard by pressing (control + command + space bar). Expand the keyboard by clicking the small box in the top right corner. Copy and paste the into the emoji search bar, then drag it into the “frequently used” section of your emoji keyboard. Now you can find it easily.
It’s worth explicitly considering—and if appropriate, deliberately omitting—each of the following elements in a definition. In general, all elements of each term should be presented before presenting the elements of the next term. The order of terms within the defining block should match the order in the definition’s title, with the primary term in a tiered joint definition always appearing first. Within each term, elements should appear in order of decreasing significance. The sequence of elements within a defining block often flows in the order listed below, but authors and editors may choose to diverge from this order as needed.
Preliminary defining text for a level joint definition: How are these terms related?
Term 1
Defining text: What is the essential meaning of this term? Include boldfaced term and alternates here.
Additional text: What other information is indispensable to a reader’s understanding of this term?
Descriptive usage notes: How and in what context is this thing used? E.g. “Companies generally create option pools before the first employees are hired.”
Confusions and disambiguations: Are there things this term is often mistaken for?
Contrast: How does this term differ from another defined term?
Consequences/Red Flags: Are there any major red flags that readers should be aware of in terms of how this term may affect them? E.g. “Full ratchet anti-dilution provisions benefit investors over founders because of the disparity they create between the values of common and preferred stock…”
Provenance: What is the source of this term? E.g. “Aaron Harris of Y Combinator coined the term in his 2018 post about process and leverage.”
The defining block is formal—clarity, precision, and accuracy are top priority. Each defining block should be able to stand alone as a piece of content. Loose commentary and jokes have no place in the defining block. Elaborative text in a Guide can be used for more informal commentary and illustrations.
Definitions should be the best brief definition available within the context of the Guide, and should include:
A brief, precise definition, close to what an encyclopedia or dictionary might give.
Abbreviations or synonyms.
Elaboration given context—either of a specific Guide or, if a global definition, of the general field in which the majority of Guides fall under. This is essential—what does the term mean specifically in the context of the topic under study?
Possible confusions or differentiations, including warnings not to confuse this term with others like it or the same term in different contexts.
Any definitive links, including authoritative sources that explore the term or its intricacies further, that correspond to this definition.
Optionally, any facts or examples that are so indispensable or helpful to understanding that they merit inclusion in the defining block.
Pitfalls to avoid in definitions, and to a more limited extent throughout the Guide, include:
Assumptions
Do not assume that the reader has any specialized knowledge of the Guide’s topic generally or the defined term specifically.
A definition should be legible according to its placement in the Guide, including what has come before it and what has not yet been covered, but also as a standalone piece of content.
For more on this, see Placement of Definitions in a Guide.
Circularity
When defining a term, do not use that term or a portion thereof in a manner that assumes a prior understanding of the term.
yes “The no-shop agreement (no-shop clause or no-shop provision) in a term sheet is a confidentiality agreement prohibiting founders from using the term sheet to solicit offers from other potential investors.”
no “The no-shop agreement (no-shop clause or no-shop provision) is a confidentiality agreement prohibiting founders from ‘shopping’ the term sheet around to other potential investors.”
An exception to this rule applies where a portion of the defined term is itself a defined term in the Guide.
Familiarity
Avoid first person.
Avoid the second person.
yes “Mortgage Insurance (MI) is a type of insurance that protects the lender if the borrower fails to make payments. It typically . . .”
no “Mortgage Insurance (MI) is a type of insurance that may protect the lender in case you fail to make payments.”
Hyperbole
Avoid language that exaggerates or should not be taken literally.
yes “Super angels are angel investors with a proven track record of successful investments as angels, but there is no agreed threshold distinguishing them from other angels.”
no “Super angels are extraordinarily active angel investors.”
Uncertainty
Avoid vague, uncertain, and imprecise language.
yes“The size of option pools varies, but typical sizes are 20% of the company’s stock for more established companies and 10% or 15% for earlier-stage companies.*”
no “A typical size for the option pool is 20% of the stock of the company, but, especially for earlier stage companies, the option pool can be 10%, 15%, or other sizes.”
yes “Mortgage Insurance (MI) is a type of insurance that protects the lender if the borrower fails to make payments. It typically . . .”
no “Mortgage Insurance (MI) is a type of insurance that may protect the lender in case you fail to make payments.”
yes“A board of directors (or BOD) is a group of people who oversee an organization 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.”
no “A board of directors (or BOD) is a group of people who have a legal obligation to oversee a corporation and ensure it serves the best interests of the shareholders.”
Avoid logical imprecision.
yes “An acquisition is when one company purchases more than 50 percent of another company.”
no “In an acquisition, one company purchases more than 50 percent of another company.” (Do other requirements need to be met for this to be an acquisition?)
yes“Dilution is when percentage ownership of each shareholder goes down as the number of outstanding shares goes up.”
no “Dilution occurs as the number of outstanding shares goes up and the percentage ownership of each shareholder goes down.” (Are other things occurring too? Does dilution itself mean more than this?)
Be sure to mention where provisions or clauses appear so that a reader engaging with a definition in the glossary or outside the Guide can still make sense of that definition.
yes“Anti-dilution provisions in a term sheet grant an investor . . .”
no “Anti-dilution provisions grant an investor . . .”
Verbosity
Keep the language in definitions as concise as possible without sacrificing essential information.
Do not “talk about the words.”
yes“X means Y.”
yes “X means Y in context C.”
yes “X means Y. It is often mistakenly confused with Z because . . .”
no “The word X means Y.”
no “X is a term that people use to mean Y.”
no “The term X broadly means Y when people are talking about C.”
Do not provide extensive lists where more concise summarizing terms are available.
yes“Accredited investors are individuals or entities . . .”
no “Accredited investors are individuals, banks, corporations, or other institutions . . .”
In cases where terms are themselves confusing, and language and usage need to be discussed, the definition should have a confusion-tagged chunk in its elaborative text.
The full defined term must be boldfaced when it is introduced in the defining block. In the case of joint definitions, all defined terms must be boldfaced when introduced. The boldfaced term should appear near the front of the definition unless it is a subsidiary term in a tiered joint definition, in which case it should appear near the front of that term’s place in the definition block’s sequence. This makes mouseovers easier to digest, and emphasizes what term or terms are being defined.
Any alternates must be boldfaced, along with the parentheses that hold them. If “or” is part of the parenthetical, it too should be boldfaced.
yes “Burn rate (or burn) is the amount of money a company loses each month after accounting for any revenue.”
DefinitionDo not use emojis in definitions, except for at the beginning of the defining block for a standard definition or for a conceptual definition. If there is a quality about a particular definition that needs to be pointed out—a pitfall or confusion, say—make an emoji-tagged statement about that quality in the elaborative text.
If in a definition you are making use of other terms or concepts that themselves are formally defined elsewhere in the Guide, you can rely on mouseovers of those terms appearing in the definition you’re working on. A definition block should focus on defining one term or on two (or more) inextricable terms in a joint definition, relying on mouseovers for any further terms used to explain them.
A definition will never mouseover the same term already being defined, even if the text appears more than once.
In general we prefer singular nouns. But this isn’t a hard-and-fast rule. Do what makes the most sense and reflects current usage.
Product mouseovers will work either way on almost all singulars or plurals.
Definitions may include key, important facts or notes or examples if they’re relevant to most readers of the definition. But they shouldn’t include illustrative examples that are pedagogical or situational.
yes “The tax brackets in the United States as of 2018 are X%, Y%, Z% . . .” (These concretely specify the tax brackets. And they can be updated later as needed.)
no “For example, if George makes $80000, he pays $X in tax.” (This is a pure illustration not appropriate for a defining occurrence. It can go as subsequent Guide text.)
Because subjects of Guides are often related, it’s common that a term defined in one Guide will also appear in one or more other Guides, although follow-on chunks may differ.
When possible, globalize the defining block by making it reusable across all Guides, and readable as stand-alone content. To globalize a definition, the defining block should not utilize language that is specific to the content of any one Guide. It should not reference its place in any single Guide with phrases like, “Now that we’ve covered X, here’s Y.” If globalizing a definition is not possible, the defining block may differ from Guide to Guide.
Joint and singular definitions, however, should always be consistent. If we define stocks and shares together in the Guide to Equity Compensation, they must also be defined together in the Guide to Raising Venture Capital. If in Raising Venture Capital we define common stock and preferred stock separately, the terms should not be defined jointly as common and preferred stock in Equity Compensation.
The defining block should only be in one place. If the reader is already expected to understand a term, avoid re-stating a definition again in similar form a second place. The mouseover will be sufficient.
A Guide should be understandable if read front to back, even without mouseovers.
That is, even though mouseovers will add a lot of convenience, we’re not abandoning the editorial responsibility of organizing the definitions.
Structurally this is still like a book in key ways. Thinking about sequencing helps us organize material, have editorial discussions on organization much like a book, and source authors much like a book too—but with the convenience that a lot of language (like “see the section on X”) can be omitted.
Forward mouseovers should be used for convenience but not to dispel confusion.
Defining occurrences should be wherever they best fit common usage by the reader. To consider where a definition goes, ask: If a reader doesn’t understand X, what other things should they be reading about?
Everything should be made as simple as possible but no simpler.Albert Einstein (maybe?)
It turns out, no-one is entirely sure who said that. And that’s something we’re keenly aware of at Holloway. We thoroughly research our Guides (and cite every source)—comparing, debating, and when possible, reconciling differing or confounding perspectives. Inaccurate or unverified quotes, ideas, data, or conclusions are anathema to us.
This section is almost entirely from MailChimp’s guide.
People are at the core of what we do at Holloway. Readers, experts, interview subjects, writers, editors, engineers—our Guides rely heavily on all these people and many more. Anything we write should be respectful, compassionate, inclusive, and accurate.
Don’t reference a person’s age unless it’s relevant to what you’re writing. If it is relevant, include the person’s specific age, offset by commas.
Don’t refer to people using age-related descriptors like “young,” “old,” or “elderly.”
When writing about a person with disabilities, don’t use the words “suffer,” “victim,” or “handicapped.” “Handicapped parking” is OK.
Don’t call groups of people “guys.” Don’t call women “girls.”
Avoid gendered terms in favor of neutral alternatives, like “server” instead of “waitress” and “businessperson” instead of “businessman.”
Gender neutral pronouns: When referencing a real person, be certain that you are using that person’s preferred gender pronoun. You can often find this information on a person’s Twitter, personal homepage, or Wikipedia page.
When referring to a person who does not identify with the gender binary, and no personal preference is known or available, we prefer “they,” “them,” and “their” pronouns.
In a series of examples, make sure that not every example uses “he,” “him,” “his.” It is best to alternate between “he,” “she,” and “they” where clear.
Use the following words as modifiers, but never as nouns:
lesbian
gay
bisexual
transgender (never “transgendered”)
trans
queer
LGBT
Don’t use these words in reference to LGBT people or communities:
homosexual
lifestyle
preference
Don’t use “same-sex” marriage, unless the distinction is relevant to what you’re writing. (Avoid “gay marriage.”) Otherwise, it’s just “marriage.”
When writing about a person, use their communicated pronouns. When in doubt, just ask or use their name.
Use “deaf” as an adjective to describe a person with significant hearing loss. You can also use “partially deaf” or “hard of hearing.”
Don’t use hyphens when referring to someone with dual heritage or nationality. For example, use “Asian American” instead of “Asian-American.”
Don’t refer to a person’s medical condition unless it’s relevant to what you’re writing.
If a reference to a person’s medical condition is warranted, use the same rules as writing about people with physical disabilities and emphasize the person first. Don’t call a person with a medical condition a “victim.”
Don’t refer to a person’s mental or cognitive condition unless it’s relevant to what you’re writing. Never assume that someone has a medical, mental, or cognitive condition.
Don’t describe a person as “mentally ill.” If a reference to a person’s mental or cognitive condition is warranted, use the same rules as writing about people with physical disabilities or medical conditions and emphasize the person first.
Use the adjective “blind” to describe a person who is unable to see. Use “low vision” to describe a person with limited vision.
Yeah, well, that’s just, like, your opinion, man.The Dude, The Big Lebowski
Not everyone agrees on the internet, but here’s how we handle these words at Holloway.
beta
checkbox
co-founder (not cofounder)
co-worker (not coworker)
double-click
drop-down (noun, adjective), drop down (verb)
ebook (not e-book)
e-commerce (the industry)
email (never hyphenate, never capitalize unless it begins a sentence)
e.g. means “exempli gratia,” or “for example.” I.e. means “id est,” or, “that is.” In general text we prefer “for example,” “like,” and “that is” or “as in” over the Latin, excepting in examples of data.
et cetera (if you really have to use it)
emoji (singular and plural)
front end (noun), front-end (adjective)
fundraise (not fund-raise)
Guide (always capitalize for any Holloway Guide)
hashtag
homepage
integrate
internet (never capitalize unless it begins a sentence)
KISS (When referring to the “Keep it simple…” acronym, often in relation to Y Combinator’s Safe)
login (noun, adjective), log in (verb)
non-profit (not nonprofit)
OK preferred over “okay,” except in dialogue
online (never capitalize unless it begins a sentence)
opt-in (noun, adjective) , opt in (verb)
pop-up (noun, adjective), pop up (verb)
P.S. (not PS or ps or p.s.)
Safe (Often referred to as SAFE, but Safe is correct in the context of convertible notes)
sexy We aim to avoid using this word whenever possible. It has no application to technology whatsoever. The only exception is when quoting someone else, but even then use judgement whether that quote should be included in anything we publish either.
signup (noun, adjective), sign up (verb)
startup (not start-up)
sync
toward(s): Adding the “s” to “toward” and “forward,” etc., is normal in Britain; in America the “s” is elided.
tweet, retweet
U.S. (over United States, usually)
username
URL
website
WiFi
Common mistakes, covered.
Use which when you’re providing information about a noun, use that when you’re pointing it out. E.g. “These rules, which I’m writing for you, are extremely helpful”; “That editor is remarkably arrogant.” This sounds simple, but ignoring this (oft-ignored) rule can lead to grave confusion.
It’s okay if this is hard, but it doesn’t have to be. Who refers to the main subject of a sentence, and whom refers to the thing being acted upon by the main verb; that thing is also known as the object. The easiest way to get this right is to use the substitution rule. If who can be substituted with he/she, it’s correct. Whom can be substituted only by him/her. Use the same rule when deciding between whoever and whomever. “Come and get it, whoever wants it.” “She wants it!” “Can I ever use whosoever?” Only if you’re singin’ Gospel.
Affect is a verb that means to influence, while effect is a noun, something that was influenced. (_Affect_ can be a noun, and effect can be a verb, but don’t worry about all that. Just remember that you almost always mean affect.)
Many people don’t know this, but there is a difference. Further refers to metaphorical or figurative distance; farther is literal. Toward and towards (and backward(s) and afterward(s) and forward(s)) Easy! Since Holloway is out of California, and California is in America, just don’t use the s. The British edition can use it.
E.g. means “exempli gratia,” or, “for example.” I.e. means “id est,” or, “that is.” These Guides shouldn’t be so stuffy that you find yourself using these. Try “for example,” “like,” and “that is” or “as in.” Et al. means “and others,” and is usually used in reference to the multiple authors of an academic article, as in, “Frankenstein, et al.” This may come up in your list of citations.
Yes. “But” and “and” are acceptable! The revolution has been won by rebel forces.
While these guides are professional and designed to be authoritative, they shouldn’t be stuffy. It’s okay to use contractions occasionally, particularly when breaking into a more informal tone in, say, a parenthetical or another type of aside.
This editor is a proponent of separating this common conjunction in the cases that it helps with emphasis. Think of the options here as a line of defense: Can not is serious (“You can not take heroin, Timmy!”), cannot is normal (“We regret to inform you that we cannot attend your wedding”), and can’t is casual (“Dogs are the best; they just can’t help it!”) Can not is also correct when the not is part of another phrase or construction, as in, “Dogs can not only wag their tails, they can dig holes, too!”
This one just about sticks in my craw, I tell you what! Into and in to are not interchangeable, and often professional writers don’t know the difference. You are going into the mystic. But you go into let your soul and spirit fly. In to is a shortened version of in order to. Now you know!
A site is a place, either physical or electronic. Cite is short for citation:
“This would make a mighty fine site for a sawmill,” said Brent. “Sure would,” said Macadamia. “Let me look up how to build one on the internet. What’s that How-To site called?” “Look up Holloway Guides. Just make sure you cite them in your book about this grand adventure!”
Data are plural, as in “These data suggest that people fight about grammar more on the internet than in person.” Data point and datum (though it is rarely used) both take a singular construction.
When referring to a specific season, as in, “The average investor check size in Spring 2019 was $400B,” capitalize the season. When referring to the mere idea of a season, as in, “I love fall, isn’t it romantic,” don’t.
Getting tech company names right can feel like an endless game of Whac-a-Mole (or is it WhackAMole?). Here’s where to look when you’re not sure, and please let us know any that we should add to this list!
Airbnb (not AirBnB or AirBnb)
AngelList (not Angel List)
Crunchbase (not Crunch base or CrunchBase)
ExtraCrunch (not Extra Crunch or Extracrunch)
PitchBook (not Pitchbook)
Product Hunt (not ProductHunt)
TechCrunch (not Tech Crunch or Techcrunch)
Techstars (not TechStars)
Y Combinator (not YCombinator)