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Updated September 15, 2023You’re reading an excerpt of The Holloway Guide to Raising Venture Capital, a book by Andy Sparks and over 55 other contributors. A current and comprehensive resource for entrepreneurs, with technical detail, practical knowledge, real-world scenarios, and pitfalls to avoid. Purchase the book to support the author and the ad-free Holloway reading experience. You get instant digital access, over 770 links and references, commentary and future updates, and a high-quality PDF download.
In this section, we’ll explore strategies for structuring a compelling email, and important pitfalls to avoid. We’ll also cover a question a lot of founders struggle to answer and around which there’s a lot of disagreement: whether you should send your pitch deck in an introductory email. Finally, we’ll cover how to schedule meetings easily.
Everything we lay out here will make your emails or DMs stand out when emailing investors. And of course, the same strategies can be used when building connections to get introduced to investors and when communicating with potential team members and customers.
Most founders just want someone to tell them exactly what their first email should look like, and we sympathize. We do suggest taking a look at some email templates like these from entrepreneur Alejandro Cremades to get a sense of ideal length and structure, but if you copy and paste email templates from around the web, your messages are going to look like everyone else’s. Here we provide a few guidelines for building a great email, but remember to be concise, sincere, personal, and use your real voice to make your email stand out. Most importantly, focus on your audience. Think of all the information you collect when creating a target list of investors as a tool to increase the chances of an investor seeing you as a trustworthy individual who is working on something compelling.
These tips apply to cold emails as well as emails sent through a connection:
Subject line. Make it compelling and clear. Investors can get hundreds of emails a week, and the only guarantee you have is that they’ll see your subject line. The purpose of the subject line is to get someone to open the email. The purpose of the email is to be glad they did. The best way to get an investor’s attention right away is to hit them with any traction you might have.
If you’re raising a Series A or beyond, you can title the subject of an email to an investor something like, “Growing revenue 100%+ YoY; $5M ARR,“ and they’ll open it. If you don’t yet have any traction, think about how you can present value to investors in just a few words. You don’t want your subject line to be “Request for Meeting,” as Founder Collective director Joseph Flaherty writes in “How to Write Better Cold Emails to VCs.” As he puts it, “Don’t ask for a meeting; present info that will make the recipient ask you for one.”
With no traction to present, you might introduce your company and describe the space you’re working in, and include how much you’re looking to raise and what round you’re raising. “Introducing X Co, raising $750K seed to support 3D-printed medical supplies.” This might sound like a lot—and keep it as short as humanly possible—but including those specifics can signal to investors that you’ve done your research and aren’t just cold emailing a bunch of firms you know nothing about. If this email was sent to a firm that writes $750K checks to early-stage companies working in health and technology, you might get yourself a reply.
That 3D-printing company example above is 75 characters. Flaherty reminds us that, including pre-header text, you might get 90 characters total to pitch an investor. Be brutal here when deciding what’s really worth including.
Greeting. Say hello! You want to greet a specific person in your opening, and first names are fine—“Hi, Angela.” If you’ve been introduced to an investor by one of your connections, thank the connector after you say hello, and let them know you’re moving them to Bcc.
If you’re cold emailing, don’t just send an email to all the investors at a firm. And don’t leave it at “Hello.” That’ll be a sign that to the recipient that you’re sending identical emails to a whole slew of investors.
Introduce your company. Whether you choose to send your pitch deck to investors via email or not, you’ll have to come up with a one- to two-sentence version of your company’s story that you can use to hook investors in your outreach emails, over coffee, or when you meet someone at a networking event. In the context of the pitch deck, this is sometimes referred to as your “thesis”; you can also think of it as your value proposition or elevator pitch. (You can also read this post by Alex Iskold for more on introducing your company to investors.)
But remember to keep it short! In the early days of a company, it’s hard to explain what you’re doing and what you’re looking for, and that often leads founders to send emails that are five paragraphs long. Try to get your pitch and ask down to a few lines. If you’ve tried, but can’t, try again until you can.
Focus on the problem, not the solution. At the Series A and beyond, your company will be judged on whether you’ve reached product-market fit. Investors will look at numbers for proof. In the early days, you’re a couple of people with an idea. Focus on the size of the problem you’re trying to solve. Convince the investor this problem must be solved and that you’re the team to solve it. How you solve it is likely to evolve as you get new users and customers. Proving you’ve identified a big problem and you’re a highly adaptable team is usually a better strategy than focusing on the intricate details of how you plan to solve it. This might look something like, “Student loan debt has risen to a record $1.6T in the United States and 66% of graduates say they regret their college education, most because of the debt they incurred.”
Tell them why. Another critical question you can answer in your first email is why you are doing this. Your mission and vision statements and company story can help here, but shorten them to one or two sentences. This is a great way to communicate to investors the vision of the company and what motivates the founders. “Student debt nearly kept me from starting a company in the first place. We believe it should be easier for everyone to pay off student loans, so the world doesn’t miss out on anyone’s potential.”
Tell them what you’re looking for. If you didn’t include it in your subject line, let investors know what round you’re raising and how much you are trying to raise to reach your next milestone.
Make your value clear. Finally, include anything that can let the investor see the value of talking with you further. If you have a lot of followers or testimonials from customers, growth stats or any revenue, or any mentions in the press, share those. But don’t share everything. Make sure they’re impressive and keep them brief. You can also include a link to your company website or marketing page, telling investors what they can find there.
Make a clear request. Your request (sometimes referred to as a “call to action” or “CTA”) should be extremely clear and have a clear way to answer.
For the email to get the first meeting, you’ll write something like this: “I’d love to get together whether at your office or over coffee and share what we’re up to and tell you what we’re building.”
importantSometimes it’s helpful to reach out to an investor ahead of being ready to fundraise and tell them you’re “thinking of fundraising in the next three to six months” and interested in getting their advice on how to approach it.
Sign off. Remember, you are offering investors something that they can’t get anywhere else. You don’t have to sign off with a super conciliatory message, like, “Thank you so much and I’m REALLY sorry for bothering you.” Simply say, “Best” (or whatever simple message you prefer), and your name. Don’t forget to include your phone number and any social media links you might use in your signature.
danger There are several things you should avoid when emailing investors. Take a pass through these to make sure you’ll steer clear of any obvious missteps.
Don’t be vague. It might seem like the less specific you are about how much you’re trying to raise, the more people will respond to you. Not so. If an investor writes $750K checks, and you don’t share whether you’re trying to raise $500K or $2M or $5M, they won’t be able to determine whether they’re a good fit as an investor or not. They’ll also assume that you haven’t done your research—on them or to determine milestones—and won’t take you as seriously.
Don’t write a lengthy email. There’s a lot to fit in your first email to an investor, but you need to make it as short as possible. Pro tip: make your first draft as long as you want, making sure you’ve hit all the key points, then try and trim it down to half the starting length. Until you want to scream, “I can’t possibly make it any shorter,” keep shortening it.
Avoid buzzwords. Buzzwords can make your emails look generic at best and, at worst, like spam. They signal a lack of depth and thoughtfulness, and, if you look closely, it’s hard to tell just what they really mean. Investors want to know that you’ve put enough thought into your company that you can describe it in your own words. What are we talking about, you ask…?
“Do you have a hard stop at the end of the hour? If we zoom out to 10,000 feet, we’re in the early stages of building our MVP and our GTM for our hyper-local social mobile consumer app. Our early experiments indicate we have signs of buy-in from key decision-makers in our beachhead market. Not only that, we have a team of rockstars ready to join just as soon as we get funded. Our proprietary machine learning algorithm will do the heavy lifting and growth-hack our way to product-market fit. The mission critical profit centers are the low hanging fruit.”
Sorry you had to go through that. But you are guilty of this, guaranteed. Unfortunately, using buzzwords is one of the easiest ways to destroy your credibility quickly, by signaling a lack of sophistication and understanding of your subject matter. If your draft investor email looks anything like the preceding paragraph, try the Feynman technique, which forces you to use less and less confusing language in an effort to explain things in their simplest terms. Try explaining what your company does to someone with no connection to the startup world. Another method to rid yourself of buzzwords is to tell your friends you’re trying to rid yourself of buzzwords—but beware: you may be in for a rude awakening.
Don’t mention other investors. Don’t share which other investors are interested in your company, because investors chat, and if you’re inflating the sense of interest it could make them not want to invest. Alternatively, they might partner up, which would decrease competition and leave you with less leverage.* However, writing, “We’ve taken a few meetings and are hoping to find a great fit with our first venture capital investment” can build scarcity without setting you up.
Don’t insult other startups. When trying to make your company stand out from any competitors, don’t bad-mouth other founders or startups in your space.
Don’t be rude. It’s one thing to build a sense of scarcity, but it’s quite another to directly tell investors that you don’t need them. It’s better to focus on the mutual benefits of a deal.
Don’t try to use reverse psychology. It’s definitely not funny to make your subject line, “You’re probably not good enough for this deal.”
Don’t ask for a non-disclosure agreement. Whether or not you’re sending a deck, do not ask for a non-disclosure agreement when emailing with investors. If there’s anything sensitive in your deck or pitch that you don’t want to share until you’re farther along, cut it out.
Don’t blame others. If you aren’t getting enthusiastic responses, you’re frequently getting ghosted, or you’re not getting any responses at all, it’s easy to blame others. Don’t. Many founders think they’re brilliant. Their ideas are going to change the world. They can see the future and they think anyone who can’t see what they see must be blind. To repeat, this kind of thinking is a mistake. If your outreach isn’t being met with any enthusiasm, it’s time to change your approach.
controversy Successful startup founders and investors do not agree on whether it’s a good idea or not to send your pitch deck, or some form of it, when initially reaching out to investors. Most concerns over sending a deck have to do with the way in which the deck represents your company and the likelihood that your deck will be forwarded to competitors.
Mark Suster advocates sending the deck. He encourages founders to think of their pitch deck as a marketing tool, like sales collateral. The pitch deck shouldn’t contain confidential information like product roadmaps or corporate secrets; it should be a compelling storytelling aid that makes it clear to an investor why your team is worth meeting with.
Alex Iskold and Charlie O’Donnell, however, caution founders against sending decks. If they hear your idea and don’t think it has promise, investors might ask for a deck so they can find some information in it to use as a gentler excuse not to take a meeting. Rather than saying, “Sorry, but you need to rethink everything,” they can open your deck, see that you’re pre-revenue, and say, “I see that you’re pre-revenue. Unfortunately, our firm does not invest in pre-revenue companies.”
Iskold also points out that sending a deck creates work for investors that you shouldn’t have to ask them to do. O’Donnell argues that founders should be able to convince someone their company is interesting in a few sentences or less, in the body of an email.
Both camps make good points. Instead of focusing on whether to send the deck or not, we recommend doing your best to create as little friction as possible for investors: Crisply communicate why your company is interesting, and make your own judgement calls over what to send each investor. Your goal should be to convince an investor to take a meeting without reading your pitch deck—but be willing to provide your pitch deck should they ask for it.
caution If you do send a pitch deck via email, expect materials you share with investors to get leaked to other investors, your competitors, and the press.* That doesn’t mean you shouldn’t tell investors what they need to know, but it does mean you want to be careful with how you share that information. You might, for example, send investors a less sensitive version of your pitch deck via email, but include additional slides when you actually present to them at their firm.
When an investor replies to your email inquiry with a willingness to meet, it’s time to schedule that meeting! A lot of people make scheduling unnecessarily hard, so use a formula. If you’re asking for a meeting with someone, you should always suggest at least three times you’re open for them to pick from. If none of those times work, you need to suggest three more.
Rinse and repeat until you’ve found a time that works for all parties. At that point, you need to send a calendar invite to hold the slot on everyone’s calendars. Calendar invites should always include the address of the meeting, your cell phone number, or the dial-in phone number if it’s a conference call. Give the meeting a title that will make sense to both (or all) participants, usually by mentioning names and whether it’s a call, coffee, or meal.
Good: “Ann > Joe,” “Breakfast Ann/Joe,” “Ann visit Acme Corp,” “Call: Ann and Joe”
Bad: “Ann,” “Coffee with Joe,” “Catch up,” “Coffee”
caution Over the last few years, more and more people use software products that auto-suggest open times for the person you’re trying to meet with. Be careful with this. It may sound irrational, but some people take offense when you send them a link with open times or ask them to schedule with a virtual assistant. It can feel impersonal and even intrusive. Take the high road and play it safe. If the meeting is important, schedule it yourself.
important It’s always a good idea, if possible, to schedule your first few meetings with investors who aren’t high on your target list. Once you’ve had a chance to practice pitching a few times, your chances are going to go way up. Don’t take your first meeting with the investor you care the most about.