Sending a Confident Message

You’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.

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.

​important​Remember, 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.