editione1.1.4
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.
You have the idea. You understand the risks of venture capital and get why the incentives behind venture capital matter. You know how much money you need to operate your company for the next 12–24 months. You’ve mastered the differences between priced rounds, safes, and convertible notes. You’ve done your research and created a list of investors who you think would be interested in investing and whom you’re interested in working with. And you’ve designed your pitch deck.
important The material we lay out here isn’t just about getting meetings with investors. This is about getting meetings in a manner that sets you up to succeed. The tools and knowledge we share will also be useful far beyond reaching out to investors, as they are the same tools and knowledge you will use to find great talent to join your team and customers to buy—and love—what you’re selling.
There is a lot to think about during this stage of outreach, like, how do you get introduced to VCs? What kinds of emails are appropriate to send? Once you’ve connected to an investor on your target list, should you email your pitch? How do you get invited to pitch in person? Is that how it works? How do you schedule meetings? When should you schedule them for? And that needling question that will follow you no matter how far you get: What if no one says yes? In this section, we’ll cover all of these questions and more.
Once you’ve assembled your target list of investors and created a concise, compelling pitch deck, you’re ready to start connecting with investors in order to get a meeting. But what if you don’t have direct inroads to anyone on your target list? The early stages of your outreach may be focused on connecting with people—usually investors or other founders—who can introduce you to an investor on your target list.
While it is possible for founders to cold email investors—and some investors are beginning to embrace the cold email as a way to level the playing field for first-time founders, which we will discuss in a little bit—the vast majority of deals are still made through connections. If someone an investor trusts trusts you, it can help you stand out from the crowd. Just don’t pay for an intro.*
Outreach comes easy to some people. For many, growing your VC network—maybe from seed—is going to feel scary. You’re going to resent feeling on the outside. You’re going to wish you’d got started a bit earlier. You’re probably going to doubt yourself, and you might feel like you’re on a tiny island and everyone else is having a venture capital party you weren’t invited to. Navigating networks of people to get the meetings that’ll get your company money is the game you’re playing, and if it feels like you’re playing on hard mode, that’s OK. That’s how a lot of first-time founders feel. It will get easier, but you’re going to have to practice.
It may not seem like it, but many successful entrepreneurs did not have pre-existing networks when they moved to Silicon Valley or started their first companies. Building your network will take research, hard work, occasional discomfort, and a lot of meetings, but everyone has to start somewhere. Many people in the startup and venture capital industry are willing to go out of their way to be helpful to newcomers, so don’t be afraid to ask.
If you’re just getting started in the startup world, we encourage you to study the principles we’ve laid out in our appendix on networking principles. Remember, growing a network isn’t just about, well, networking to get close to investors. Think of it as building a community of people who have been where you are now, who can answer questions, help you practice pitching, let you know what you might expect from certain firms or individuals, and so much more. Eventually, you’ll be the one able to help a first-time founder meet their first investor, and you’ll be damn happy to do it. (In the appendix, we also discuss the importance of mentorship and strategies for finding a great mentor; when you’re not feeling confident, a mentor acts as an advocate and sponsor and will help you learn to pitch yourself to yourself.)
Networking principles apply to building a VC network as well as a peer group of founders, who can be invaluable allies in this process and who are often the gateway to investors. We’ll focus on three strategies specific to getting connected to investors on your target list: using social media, reaching out to other founders, and making it easy for your connections to help you out.
More resources for networking as an underrepresented founder are included in the section on privilege and access.
Before moving on to more creative approaches, check LinkedIn to see if you have any second-degree connections in common with investors on your target list. Asking these mutual connections for an introduction is your low-hanging fruit. If you don’t have any second-degree connections in common, look for third-degree connections. In this case, you can ask the person you know to introduce you to the person who knows the investor. This is less direct and more work, but it’s a start. An email or a quick conversation with this third-degree connection can be a good route to an investor. If you don’t have any second- or third-degree connections in common with any of the investors on your list, never fear—all is not lost.
One way to build trust and connect with investors online can be to follow and interact with them on Twitter. The ecosystem of VCs and founders who use Twitter is notoriously active. Follow every investor on your target list who has a profile on Twitter. A lot of relationships in the startup world are built on Twitter. If you’re not a Twitter power-user, this will sound strange, but Twitter is an absolute goldmine for building relationships with benevolent strangers. It can also be a den of snakes, but fortunately you can choose who you follow and engage with. Familiarize yourself with bloggers and regular Twitter users from the community. Plenty of these individuals are willing and known to respond to questions from those looking to learn about how to raise venture capital.
caution This isn’t a license to harass or bother people, though. If you follow an investor who’s on your target list, respond to their tweets. Ask clarifying questions. Suggest relevant information. Be generally helpful. But don’t be a gadfly. If the investor finds your comments insightful, they may follow you back. At that point, you will be able to send them a direct message, which presents a delicate opportunity. If you are professional and succinct in your request, you may be able to wrangle a coffee meeting out of a direct message (DM).
But it’s one thing to send a cold DM that is brief and confident. It is something else to send the same message over email, LinkedIn, a Twitter DM request, and three other channels. The first is a determined attempt to get someone’s attention. The latter is at least overzealous and possibly harassment—not OK. If you’re verbose, overzealous, or rude, the investor will probably block you. It’s OK to follow an investor and sincerely engage with them on a social network like Twitter with the goal of getting a meeting, because it’s an honest attempt to build trust and make a connection. When drafting your outreach, whether it’s in an email or somewhere else, ask yourself how you’d feel if a stranger were to use the same tactics to get a meeting with you.
danger Earnest research and confident outreach do not mean walking into an investor’s office and demanding they meet with you. And it definitely does not mean finding someone’s address and showing up at their house with your pitch deck—that is an egregious breach of privacy that will make the person you’re looking to pitch feel unsafe.
If you’re struggling with confidence at this stage, sometimes it can be enough to hear that you are not the only founder who sometimes feels like they don’t belong—especially if you are underrepresented at venture capital firms, and underrepresented as a recipient of venture capital funding. First of all: you are not alone. Networking and speaking openly with other founders who have experienced similar struggles is a great way to build your confidence at this stage. And, if those founders have raised before, you can get specific advice about what attitudes and practices you can expect at a given firm or from an investor you’re hoping to meet with—and they may be able and willing to connect you to one of those investors.
Follow founders you admire and founders of companies in your industry on Twitter and LinkedIn. You can find most of their names by Googling [company name] + founder. Interact with these people. Reply to their tweets. Remember, other founders can often be your connection to investors. Build up a back-and-forth, and after a while ask them if they’d be willing to hop on the phone or get a cup of coffee.
If you have friends who work at venture-backed startups, they may be willing to introduce you to the founder of their company, who may be willing to help you learn the ropes and get connected.
If you don’t have friends in the venture world, fret not. Sending cold emails to founders who are one to four years ahead of you in their journey can yield surprising results. You may not get Patrick Collison from Stripe or Drew Houston from Dropbox to respond to your outreach, but someone who leads a ~30–50 person company (or smaller) is far more likely to read all of their emails and be willing to help someone out when they have the time. Many founders’ email addresses are firstname@domain.com. If that doesn’t work, try sending an email to founders@domain.com, as many entrepreneurs set up a “founders@” alias to communicate with investors and each other. You can also try Hunter, a resource for finding company email patterns.
important Emailing founders can be a great move if an investor on your target list invested in their company. Don’t lead with an email with a subject like “Can you introduce me to Naval Ravikant?” Try something softer like, “Green entrepreneur looking to build a network.” Many people are willing to help, but they usually want to talk or meet before spending social capital introducing you to people they know.
Many notable investors, founders, and operators are more than willing to answer an email or request if you have a well-stated and thoughtful question that they are genuinely equipped to handle. By building a rapport over time, you can end up with a network. Going out to build a network just to get ahead is not the right approach—getting advice and helping others will leave you with a network as a benefit.
Still, so much of networking is asking people for favors and actually getting them to complete the favor. It is OK to ask for help—do it! In the startup community, you can expect to find a lot of that. But don’t forget that asking for things means asking people to put in work on your behalf—time, energy, money.
In his blog post, “Make it easy to say yes,” Noah Kagan reminds us that it’s “much easier for the other person to help when they see you’ve made a solid investment already.” Here’s what you need to know:
Be specific. Ask for what you need and explain why. Don’t be vague in the hopes that the person will make an offer to help you with exactly what you’re looking for. If the person you’re asking for help can’t figure out what their role is supposed to be, it’s going to create more work for them to go back and forth with you until they can pull it out. But specificity does not mean over-explaining. You also want to keep it short. You can (and should) include a line like, “Please let me know if there’s any more information I can provide.”
Be complimentary. It never hurts to pump the person up a little. Are they uniquely positioned to help you because they’ve been really successful at X in the past? Do you completely trust their opinion and ability because so-and-so in your circle speaks highly of them? Maybe you read a recent blog post of theirs that blew you out of the water. Let them know.
Don’t be selfish. Yes, many people in the startup community are eager to help others. But you are not entitled to other people’s time or to a connection. Don’t use language like “I need,” or anything that sounds like “It’s really important that you do this for me.” Don’t demand anything, and be sensitive of their time even if you’re running on a deadline.
The double opt-in introduction. This strategy is for the person making the connection for you, but it’s good for you to know, because with a forwardable introduction email (below), you can help. The double opt-in introduction is a mouthful but pretty straightforward. When you ask someone for an introduction, that person should double check that the person you want to meet is actually interested in being introduced. If they say yes, your contact is free to make the connection. People are busy and this is a gesture of respect. So in the future if someone asks you to connect them to another person, you’ll want to check and see if that person is interested and if they have the time.
The forwardable introduction email. The forwardable introduction email is a way to maximize your chances of success with double opt-in introductions and make it easy for the people you’re asking for help to say yes. This is a big one.
The problem with most double opt-in introduction requests is that they create work for the person connecting the two parties. To check whether the person you want to meet is interested, they have to write an email that lays out why you want to be connected and why they should speak with you. For most people, writing an email about someone else’s career and positive characteristics isn’t the biggest priority in the work day. As a result, doing so gets deprioritized and may never happen.
To get around this, when you’re asking for an introduction, you should write an email to the connector that they can simply forward to the person you’re asking to meet. This email should contain a bit about you and why you want to be introduced. This way, the connector can simply press “forward,” and add a short note along the lines of, “So-and-so is terrific; I think you should meet them.” It only takes a few seconds. If the person says they’re interested, then all the connector has to do is add you on a new reply on the same email thread and the connection is made.
important When you get this far, make sure to Bcc your connector when you thank them in your reply.
Say thank you. In addition to thanking the person and Bcc’ing them, it’s always nice to send them a follow-up email letting them know that the connection was successful and you really appreciate their involvement. If the connection turns out to be huge for you, you can even send a handwritten note or a small token of appreciation. When you’re the person being asked for help, what would you like to hear?
Love it or hate it, much of the venture capital industry depends on so-called warm introductions—that is, connecting with an investor via a third party who knows both of you. Many investors view a founder’s ability to wrangle up a set of warm introductions as an indication of how successful they will be at connecting with future hires and customers. The purpose of a warm introduction is to show an investor that someone out there is willing to put their own reputation on the line by introducing you. They’re vouching for you, and they’re taking the time to help you out.
controversy A warm intro from a close friend or colleague never hurts.* But not everyone agrees you need to be close with the person making the intro. So long as the introduction is credible, it can be a good start, even if it’s not necessarily an endorsement.*
But others, like Homebrew investor Hunter Walk, say that an introduction from someone who doesn’t really know you does not work in your favor. Better, Walk says, is a powerful cold email.* Yes, a well-worded and personalized cold email to an investor can yield success when you’re trying to raise a seed round.* Venture capitalist Arlan Hamilton has also spoken about the power in reading cold emails from founders—some VCs see it as a way to open the playing field to first-time founders who are underrepresented in venture capital networks. From her own experience, Hamilton offers advice on crafting the perfect cold email to investors.
Here’s a brief excerpt from a Recode interview by Eric Johnson with Freada Kapor Klein, of Kapor Capital, who explains why the cold email can benefit investors and founders alike:
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…”
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?
Klein: Completely. Your zip code isn’t close enough to mine. It’s completely biased, and it’s confusing accidents of birth with accomplishment.
Johnson: You’d get rid of the warm intro.
Klein: Get rid of the warm intro. What’s really interesting is we’ve gotten rid of the warm intro. People can send us their pitches directly over the website. We have invested in companies whose pitch decks come in over the website and none of us know anybody who could’ve introduced them to us. And they are businesses that meet our investment criteria.
Many firms who appreciate the power of the cold email will say so on their websites, or have a portal for cold submissions. Jane VC is one such firm actively campaigning for cold pitches from women founders.*
important If you go with a cold email, make sure you’ve done your research and tailor your pitch to the investor’s interests and preferred method of communication. Use all of the same strategies we lay out next for designing a great email. Like any email to investors, a cold email should be clear, concise, and complimentary, including:
A short introduction of yourself and your business.
Why recipient is a fit to help. Connect to them and show you have insight into their strengths and have done your research.
A clear request.
If you’re sending cold emails to investors, it’s still valuable to make connections and build your network! The founders, investors, and other players you connect with can help you find the right investors for you, and answer a lot of questions along the way.
As you begin reaching out to investors, how confident they perceive you to be is directly correlated to how successful you are at getting these crucial first meetings and ultimately delivering a pitch that investors can’t walk away from. Remember, at the early stages, investors are investing in you and your team more than in your idea or company. When it comes to pitching, whether it’s in an email trying to get a meeting, or over coffee, or in a conference room at a firm, investors need to believe you’ll move heaven and earth to turn your vision into reality.
While we can’t anticipate what the recipients of your emails or the rooms you walk into will be like, there are a few strategies for projecting confidence that can actually help you build real confidence in yourself, your company, and your ability to capture investor interest. Strategies for projecting the right amount of confidence are not a one-size-fits-all formula. But a few pieces of guidance to consider will help you figure out—along with a good amount of trial and error—what works best for you.
Nail your story. Getting a grip on the story you’re telling investors is one of the ways you can actually build your confidence—if you believe in the story, someone out there will too. Storytelling and confidence are a double helix of skills that, if mastered, can be used to emotionally hook investors on wanting to be a part of the future you’re creating. We help you build your company story in Designing Your Pitch.
It’s how you say it. While the “7%” rule (the idea, based on a somewhat dubious academic study from 1971 stating that those being pitched to only assign 7% of a pitch’s value to the actual words being said) is likely exaggerated, it’s still essential that founders be very careful in how they express themselves. Here are a couple of tips:
Be specific. “We are raising $3M on a $9M pre” is a lot better than “We’re raising somewhere between $3M and $5M on a $9M-ish pre.”
Ask for what you need. “We are booking first meetings for the week of October 22, second meetings the following week, partner meetings for the week after that, and we hope to have a term sheet before Thanksgiving. We prefer to take all meetings in the Chicago area in order to make the best use of our time by minimizing commutes.” This approach not only evokes a sense that your time is scarce, giving you leverage, but is a lot more effective than putting all responsibility on the investor by saying something like, “We’re planning to start fundraising in the next few weeks. When are you open for coffee?”
Be sincere. If you aren’t confident that you’ve chosen a big market and can pull together a great team to build a solution to that market’s problems, maybe you shouldn’t be raising money yet. The last thing you want to do is project a confidence that is ultimately insincere—it can come off as arrogance or bad acting. Look closely at the specific things that give you pause, and make a list. Literally, write these things down. If they’re not legitimate, you can start to work on putting aside your fear. If what is draining your confidence is actually something you can work at and improve, you’ll know where to start.
Prepare. The best way to appear genuinely confident is to be genuinely confident, and the best way to do that is to prepare. Reading this guide is a great way to start, so good work! You know why you’ve decided to raise in the first place, and you’ve nailed down the numbers you’re looking for and can explain their rationale. You can tell your company story and you’ve built your pitch deck.
importantRemember, you want to have a pitch deck prepared as soon as you begin reaching out to investors in earnest. Some of them may ask to see a version of your deck via email before they agree to take a meeting. If an investor does want to set a meeting with you, you need to have your deck ready to go—be neither cocky nor cavalier when it comes to the pitch deck. Investors can tell when a deck is sloppy and a founder hasn’t prepared. Throwing your deck together the night before a meeting is a pretty clear sign that you don’t care enough about your company and that you don’t respect investors’ time. Head back to Designing Your Pitch if you don’t have your deck together yet!
Due diligence. Preparation is also about due diligence—that is, doing the necessary research on your audience of potential investors. Luckily, you researched your audience when you created your target list of investors, so you’ll have something specific to say in every email, and you won’t be walking in blind to any meeting you might get. The best way to keep from being intimidated is to know as much as possible about the people you’re emailing and meeting with. They’re just people! They’ve had career highs and lows, they graduated from whatever college you might have some connection to, they’ve written stuff online you have an opinion about. Learning as much as possible about who these investors are can help you build a personal connection to them, which can radically reduce the discomfort you might feel sending them a cold email or walking into a meeting.
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.
For startup founders, the whole point of a first pitch meeting with venture capitalists is to secure a second one.Beck Bamberger, investor, Backstage Capital; founder, BAM Communications*
If you’re raising Series A or later, the process of meeting with investors and negotiating the terms of a deal are pretty well standardized. But for early-stage companies, it can be hard to know what to expect. A casual meeting with an investor might turn into a pitch meeting. You could meet with investors at one firm two or three times before making a formal pitch to the partners who guard the checkbook.
Once you’ve begun reaching out to investors with the goal of getting a meeting, things can move pretty quickly. Every founder–investor relationship is different, and early-stage investors can have wildly different approaches and practices when it comes to meeting with founders. This section is a general overview of what you can expect from your first few meetings with investors.