Gary Vaynerchuk wears many hats: social media impresario, wunderkind of the conference circuit, businessman, and of course, investor. Looking to pitch him, or someone else of his magnitude? Here are some things that you should keep in mind:

#1: Do Your Homework.

First thing's first: if you're going to pitch Gary Vee as he's affectionately called, come prepared. There are so many resources out there that have information on angel investors and their investments, yet there are still some who opt not to do the legwork. "I'm stunned by how many people don't do homework," says Vaynerchuk, who I had the pleasure of sitting down with at the recent Dublin Tech Summit. As one example of not doing your homework: Vaynerchuk has actually had people come in and pitch him something that he already has two investments in.

Not only is it important to keep in mind the projects that any investor has already put money into, but it's also crucial to be aware of what he or she said and done in the past. As Vaynerchuk puts it, "Pay attention to what I'm doing. Influencer marketing, that's going to get my attention. Facebook long-form video, that's going to get my attention. When I say VR is 20 years away, on stage, how are you coming to me and saying, 'Okay, I'm building a consumer VR thing that's going to come out next year'?"

A successful pitch isn't just about how good your product is, it's also about convincing the other people in the room that you need them and value their expertise. It's hard for them to feel valued if you haven't even bothered to read up on them beforehand. In this day and age, where so much information is available on the internet, it seems almost comical not to take advantage of those vast resources.

#2: Be Empathetic.

Be aware of what the investor is thinking about. This second piece of advice goes hand-in-hand with the first -- after all, it's difficult to know what the investor wants without doing any research. If you're not sure what the person on the other side of the table really needs, it becomes an uphill battle to find the opening that will convince them to bankroll your project.

For Vaynerchuk, "the most empathetic investors and operators win, because they're good salespeople, because they think about what the other person is thinking about." All too often, people focus too much on the merits of the product, and not enough on the person they need to sell it to.

#3: Be Practical.

Vaynerchuk says that many of the pitches he hears "lack practicality." People come to him with business plans that count on the future economic climate being as rosy as it is today, which is impossible. Not only that, but he says that the success of entrepreneurs such as Mark Zuckerberg has caused completely changed what people think of as success: ten years ago, most young people thought of investment banking, Wall Street, and consulting as the pathways to success; now, people want to start the next Facebook or AirBnB.

For Vaynerchuk, young people have "course-corrected from being built as a good student, a great manager, a great thinker, an operator, to somebody who needs to be completely creative, chaotic, and has a stomach for adversity and change at a rapid pace." This change in mindset has created a generation of entrepreneurs with a more selfish approach to doing business. Vaynerchuk says that his advice for "hustler entrepreneurs like [himself]" is for them to "be self aware." He adds, "You're not a genious. You're a hard worker. You'll push it through, you'll find an angle."

#4: Skip the Buzzwords.

One recent trend that has proved to be especially irritating to Vaynerchuk is the constant use of buzzwords in pitches. "I can only sit through so many, "I'm going to be the Airbnb of, I'm going to be the Uber of...," he remarks. "The same stuff that would've worked in 1954, and the same stuff that would've worked in 1837, that's what I believe in. I'm old school like that." Like other investors, he is focused on the fundamentals, not the flash.

#5: Don't Fake the Funk.

Speaking of flash: don't try to play games with the people who are thinking of giving you money. Vaynerchuk says, "The only people you're going to trick are losing players, so you're not going to want them on their side anyway."

The key to winning him over, he says, is self-awareness. Don't feel as though you have to answer a question just because it's been asked. Sometimes it's better to be honest about your shortcomings, and acknowledge that you don't have the know-how or expertise yet. Vaynerchuk says that he prefers those who are forthright and admit their weaknesses to those who prevaricate and give a non-answer.

Ultimately, you're trying to build a meaningful relationship with someone who has the resources and expertise you need. If you're not honest about your shortcomings, or you try to avoid answering the hard questions, the only person you're going to hurt is yourself.

#6: Accept that You are the Product.

You're not just pitching a product -- you're also pitching yourself. Vaynerchuk admits that he's "betting on the jockey a lot of times"; in other words, the product itself is less important than the person who pitched it.

One of those jockeys was Casey Neistat, the YouTuber whose company Gary had invested in (and which was recently acquired by CNN). Vaynerchuk says that betting on Neistat was easy because of his ability and expertise, and that ultimately it was Neistat who came up with the strategy that made Vaynerchuk's investment worthwhile. Investing in people who are already established in their field and already have a gameplan makes Vaynerchuk's job a lot easier. "It's hard enough to get a victory," he says, "which is why it's very good to bet on a jockey."

#7: Don't Expect Him to Run the Business for You.

"I'm not interested in micromanaging," Vaynerchuk says. If he's asked to, he'll give advice to his startups. But otherwise, he maintains, he "won't impose [his] will on another entrepreneur." Why? Because it's your baby, not his.


Now that you've read the above, you're one step closer to successfully pitching Gary, or someone else at his level. Think you have what it takes?

Published on: Mar 14, 2017
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