How to Pitch to Boys With Money

With the number of women in venture capital at just four percent, pitching to get VC funding means learning how to play to a male audience.

VC Fest, which takes place four times a year in the heart of Manhattan’s Tech Hub near Google’s office, is, to say the least, a very big deal. The fest invites hot young entrepreneurs to venues such as City Winery to pitch to venture capitalists looking to fund new businesses or provide second-round funding to young companies that are hitting their growth targets. Business owners must take to the stage with headset, microphone, slides, lights, and in no more than 12 minutes, they must present a business idea and make a big ask for big money to secure the future of their enterprise. Big deal, indeed.

The audience is usually comprised of boys with money. That’s the VC crowd for you; only about four percent of women are in VC financing. At City Winery, for example, 120 men with money sat in judgment of the pitches, which can ratchet up the nerves of female presenters.

Yellow Bird Health, an incubator for startups, takes an active role in supporting and prepping young entrepreneurs to take the stage in front of the VC men. But the Yellow Bird team is all male. Most of the entrepreneurs going to them for preparation are male. The male entrepreneurs who present to the “boys” may already feel a kinship with the audience. After all, they look the same. They dress the same.

But what happens when Robin Hyde, a female entrepreneur with a brilliant new business called Health Jump, comes to Yellow Bird for support? Their all-male team is not quite sure how to coach her, even though they think they can. She’s certainly smart enough to know that when she takes the stage, she’s not in familiar territory and it may even be unfriendly territory. Understandably, that makes her nervous. Her knees feel like they might buckle. Also, she’s not so comfortable using a headset, slides, and lights. Given that I have expertise as a conference producer and presentation coach, she called me for help.

I met Robin at our studio and watched her deliver her Health Jump pitch. As soon as I heard her, I knew we had to put some “female” language back into her male-edited script. But as Robin rehearsed again, I detected a fear that was not about her script or her ask. It wasn’t about the lights, or the headset either. It actually wasn’t even about her opening line and assuring she had it down cold. She was unsure if her company would appeal to “the boys.”

She also didn’t know what to wear on stage. She didn’t know how to be memorable without being provocative. And she wasn’t sure if she’d be able to fend off any disruptive Q/A from the boys who wanted to challenge her business plan.

I was not about to let Robin’s fears derail her. This is what I told her.

Hey Robin, you’re a really smart girl. In fact, smart enough to create and develop a very cool company called Health Jump. You’re also a very experienced manager who spent six years running a huge division with a well-known pharmaceutical company and juggled more responsibilities than most. Getting on the City Winery stage is just one more exciting business challenge that has nothing to do with gender, yours or that of your audience. So focus on strategy and how you can tackle the challenge.

Here’s your game plan:

Reset Your Mindset: With a strong sound idea for a company, one that can scale and be a good investment, you should proudly take it to the stage. Anyone who doesn’t “get it” is stupid. Or arrogant. If it’s really an exciting idea that changes lives or people’s health, not only will it thrill the audience, but there’s a chance some will fight over funding you. What’s your mindset? “They’re sure lucky I’m giving them a chance to get in on this investment at such an early stage.”

Think Performance: When you appear on stage, remember it’s a performance. Always. No second-guessing on this. Make sure you’ve checked out the staging ahead of time. Ask for what you need to make you comfortable, whether that be a chair to sit on or a podium to stand. Or whatever. Ask for a quick tech run so that you know the backstage crew won’t let you down. And understand that what you wear is about enhancing your performance and not about being a woman. Don’t confuse the two. If you are Health Jump, maybe you should appear in workout garb, whether that be spandex or boxing clothes. If an outfit or a hot look “plays the boys” a little, that’s their issue. You are delivering a brand impression, and what you choose to wear should enhance that brand. It’s not really about you, personally. What’s your thinking? “My outfit gives me the power to sell this business idea.”

Control the Experience: Selling a business idea and asking for money requires grabbing the attention of the investor. Being memorable can require delivering the unexpected or being offbeat, so long as you control the experience. The best example of this comes from a well-known female business owner who, many years ago, was trying to launch a very sexy lingerie company. (Not divulging the name!) Some of her featured items were rather “naughty” or suggestive. She had to figure out how to grab attention—and funding—from the “boys” in the room and be remembered as a presenter of a serious business opportunity. But at the same time, she had to make sure they didn’t “diss” her or laugh her out of the room. What was her strategy? Before the VC presentation, she put a pair of red lace panties on each seat. No one forgot her. Or her business.

If you’ve done your prep work and you believe in your business idea, then you can ignore, or even laugh at, a question that’s meant to challenge your confidence or insult you. Anyone who tries to be disruptive or pushy basically enjoys hearing his own voice. And you surely don’t want him as an investor. Some VCs find power and pleasure in asking questions that show how smart they are. Let them! If the question is truly smart, your job is to learn from it. If it’s not in your wheelhouse, say so. If the men intimidate you, then you may not be ready to present. Rethink your timing. What’s your mindset? “I need smart partners and investors who want this business to succeed. I’ll be ready to show them how.”

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