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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.
There’s no two ways about it: if you want to successfully raise venture capital, you have to devote a significant amount of time to practicing your pitch. You could send an email today and get a call tomorrow that an investor wants to meet. Do not go in unprepared.
A big part of the purpose of rehearsing is that it gives you flexibility. You will be interrupted in a pitch meeting. Hear us: you won’t make it to all of your slides! But if you know the material frontward and backward, you can move around within that material depending on the reactions in the room and the questions you get asked. Improv classes won’t help here. There is nothing more valuable you can take with you into a pitch meeting than preparation.
Build an outline. Starting with an outline, make sure the beats of your story are right. Digressions and extra detail can be tempting when speaking, and the outline—which should be a little more detailed than the talking points on the slides—will help you move swiftly through the presentation. As we said above, we suggest splitting up the outline into four modules, which can also help with flexibility: pain point and solution, founder and team, data, and getting to market.
Locate signposts. Come up with turns of phrase that have really resonated with people while you’ve talked about your mission or company. Peg those linguistic diamonds to different parts of the outline and try to remember them word for word (but don’t freak out if you don’t get to deliver one). This can help you keep track of where you are.
The first step is to spend some time practicing alone. When you practice in front of others, you’re adding a layer of complexity and emotional overhead that’s not going to help you until you have the material itself down cold.
You don’t have to do this in front of a mirror, though you can if it helps. Your job is to get through the entire deck ten times. The first few times you try, you’re going to have some false starts, you’re going to get to the second slide and forget what’s next. Messing up a bunch of times is part of this process! Staring at the blinking cursor of your mind does not mean you’ve already failed—it means you’re practicing so you don’t fail in front of others. So once you’ve gotten through the entire thing once, do it nine more times.
The purpose of practicing in front of an audience is to do a SWOT analysis: figuring out your pitch’s strengths and weaknesses, opportunities to improve it, and threats that could sink your pitch. If you prefer, you can tell your audience that their job is to point out any plot holes in the story you’re telling.
But who should you practice in front of?
We recommend moving outward in concentric circles until you’ve covered your bases. You started with yourself—you’re the center. Now you want to bring in a little group of people who love you. Maybe they don’t know anything about your product, but they are fully invested in you. These people are going to help you with your confidence. They’re going to tell you you’re great, and maybe remind you not to talk so loudly. This is your chance to start practicing in front of an audience, which can inspire odd behaviors that maybe weren’t present when you were alone. Are you suddenly shouting? Why are your hands not moving? Are they normally like that? But your friends will also tell you what you’re doing right, and knowing what’s working is just as important as knowing what to change. This is a really important step—don’t discount the power of being pumped up by your friends.
caution Pitching friends is important, but be careful about the advice on your content that you get from people unfamiliar with the pitching process or with your field. Pitching a novice can help to a degree because you will have to pitch all kinds of people in the future. But for the purposes of preparing a pitch for investors, your goal is to sell equity in a business, not to create a marketing tool to sell a product or service. If you’re getting feedback on the marketing potential of your pitch it can be distracting.
Once your confidence has been bolstered, widen the circle a bit. Bring in some professional contacts who may be familiar with the market or investors you’ll be pitching to. These people are going to start asking the tough questions, and poking holes in your structure and logic. Adjust your material in response to their feedback.
Finally, it’s time for the big guns to blow holes right through your story: mentors, advisors, and, most importantly, other founders. The most valuable advice you get will be from people who have pitched before, who can tell you what it feels like and what to expect, and enact some of the attitudes of the investors they have known. If you’ve already received friends and family or angel investments, you can call those investors in, too.
You might think that practicing in front of VCs is a good idea, and if you are friendly with some investors you certainly can bring them on. But their advice to you should only go so far. Every VC has their own styles and opinions and preferences, and what works for one will not necessarily work for someone else—especially someone at a different firm or who works in a different sector.
If you don’t know any founders or VCs, check out our tips on getting connected in Getting the Meeting, and general networking strategies and principles in Appendix A: Networking and Mentorship. You can even find a local business professional, at the very least. Clarity.fm is a good tool to find experts and get in touch to practice your pitch. You can also consider finding an organization that helps founders practice their pitch and hook up with mentors who can help, like Female Founders Office Hours, or The Founder Forge in Chicago. (Search “founder office hours” and your city.)
Preparing to answer questions is extremely important. This is how you stress test your deck. You can start thinking about this as you ready your deck and outline, but make sure you continue to respond to questions and iterate on your presentation as you involve others. Here are a few tips:
Write down the questions that would scare you most to be asked in a meeting. People are reluctant to do this, but it’s an important step. Chances are, you will get asked those questions, so prepare answers in advance. Remember, your answer can be, “I don’t know yet, but here’s how I plan to get signal on that.” When you start rehearsing in front of an audience, assign members of your rehearsal audience these questions to interrupt you with so you can practice answering them.
important The benefit of rehearsing in front of people who know something about your topic is that they can ask relevant questions. But the single most common question you will be asked in a pitch meeting doesn’t take any special expertise to ask: “How do you know that?”
When answering, “How do you know that?” don’t get defensive. It’s not good enough to say, “Well, I’ve experienced it,” or “I’ve met so many people who have experienced this.” The best answers will be tied to data, even if it’s limited data. Maybe you’re still working off qualitative data from some end users. Well, how many people did you talk to? How many people do you still plan to talk to? Any kind of data can help you here.
You should go through your talking points and determine whether you can answer “How do you know that?” for every claim you make, and at any stage you can have your practice audience poke you with this, too. It’s the number one stress test of your deck.
According to one expert Silicon Valley storyteller we spoke with, “80% of your success at this is going to be because of your energy, and 20% is going to be because of the content. The way you make these people feel is going to be much more important than what you make them think.”
In Getting the Meeting, we’ll talk a lot more on the subject of confidence and get into a few things you can do to show investors that you’re 100% devoted to the success of your project and believe that it will succeed. Here, we’ll share a few tips for displaying confidence that are specific to delivering your pitch in an investor meeting.
First of all, your presentation is a performance, not a lecture. As part of your practice sessions, ask for feedback on your delivery as well as on the content. Try to assess your liabilities when it comes to projecting confidence in advance, and then begin to problem-solve. If you are having trouble displaying confidence, treat it like a problem to solve rather than a personal failure. If your audience are perceiving foibles in your presentation during rehearsal, know that these are problems that have a solution.
caution Don’t say, “I’m just the kind of person who does X, and I’m not going to be able to do Y.” Even if you’re a serious introvert, if you have a command of the material so that you can focus on things besides what comes in the next slide, then you’re in better shape to work on projecting confidence and on your presentation skills.
Do you vary your cadence and vocal quality, or is everything a slow or fast monotone? Modulation—a range in inflection—in speech represents the opposite of tension: it displays an ease that will show your audience you’re confident in the material and totally prepared.
Are your hands pressed against the table or your arms crossed? Loosen up. Gesturing while talking shows a command of the space and will come across as confident to investors.
Are your shoulders square, or you hunched over, looking like you’re hiding from something? Investors are looking for founders who won’t bend under pressure and scrutiny from the public, the media, and their customers.
Consider a public speaking course if presenting isn’t comfortable for you. Alternatively, improv is also a popular training tool for public speakers—getting over being embarrassed can be a valuable skill. Improv won’t help you present a better pitch deck—that’s in the design, preparation, and rehearsal. But if just being in front of people isn’t your strong suit, practicing at failing can help.
important Of course, the best way to display confidence is to be really, really confident in what you’re saying. During your practice sessions, pay attention to any parts of the presentation where you don’t have 100% confidence in what you’re saying. Remember the cardinal question: “How do you know that?” Rethink, reword, and rework the content until it’s all true for you.
It’s one thing to tell investors what your product does. “It has this benefit and that benefit and does this thing that’s never been done before!” But telling investors about what you’re offering means relying a lot—maybe too much—on their subjective imaginations. Showing them the product is where you get to bring them into the world you imagine.
Just as pitching verbally is a skill you’ll need outside of convincing investors to invest, you will demo your product to other people as well—potential hires, customers, reporters, the general public. Nailing your product demo is time well spent.