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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.
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.