How to Approach VCs Like a Pickup Artist


primaryphoto - flckr

Picture this: you are in the middle of a startup conference filled with VCs with deep pockets that you desperately need to reach into. You hype yourself up, doing mental jumping jacks. Before you know it, you are sweating more than a coked up Rob Ford.

Soon the hype turns into self-sabotaging doubt. You run through all the irrational reasons of why you shouldn’t approach that investor.

You decide that your startup dreams aren’t worth pursuing and determine that entertaining such notions was foolish.

Sound familiar? It should. I’ve seen far too many entrepreneurs either not approach potential investors at all or crash and burn when they do.

The advent of startup conferences like TechCrunch Disrupt have forced entrepreneurs into a situation where they have to cold-approach investors.

A few years back, I grudgingly became a PUA (Pickup Artist—think of Neil Strauss’ “The Game”) at my friends’ behest.

Like most men hearing about a new technique of bedding beautiful women, I was skeptical. But with an open mind, I dove right in, learning a few important lessons in the process.

I soon discovered these techniques could also be used in a powerful way when it came to business.

One of the first things I learned was how to always approach women with confidence. For entrepreneurs, this is no different.

Almost all the founders who approach me seem afraid, like I was some VC boogeyman. To be brutally honest, most VCs are like boogeymen with the added unpleasantness of a huge ego. But this is precisely why you need to develop the swagger of a thousand men.

In truth, VCs love the high they get from being pitched to, even if they know their time is being wasted—there is something inherently ambrosial about it. This is the reason it can be difficult to pitch to them; they always have the upper hand and feed off of the ego trip.

VCs also have a “shitty entrepreneur defense shield” (in the PUA world, it’s what’s known as a “shield”). Women built this defense to ward off any would-be suitors they deem inadequate. VCs developed their own version to deflect the endless mediocrity headed their way.

So how do you make first contact? How do you prevent severely attention-deficit VCs like me from falling into a comatic trance where I begin to picture you in your underwear to keep from drifting off?

An indirect approach is best.

If your target VC is chatting in a group, ignore him and approach the other individuals in that group first.

Start by making a funny observation or anything that starts a dialogue. Sometimes you don’t even need to dive right into your pitch, but instead, establish rapport and good conversation. The goal is to make everyone in the group feel important except the VC.

The reasoning behind this is quite simple: anytime an entrepreneur approaches a VC, there is a predetermined level of value. The entrepreneur has little to no value because he or she is the one who needs something that only the VC can provide. In fact, you are giving up almost all of your value before you even approach!

But by acknowledging the others in the group, you preserve your value while the ignored VC stands there listening to your awesome startup wondering if he/she will ever get a chance to take part in the conversation.

If you successfully regale the others with stories of your startup and how it’s going to change the world, the target VC will eventually take the bait.

Continue to maintain your value with an “I don’t need you” attitude. But don’t get too cocky. When the VC’s value is equal to yours, you have to lose the bravado and start closing the deal.

“If they have advantage, entice them; if they are confused, take them, if they are substantial, prepare for them, if they are strong, avoid them, if they are angry, disturb them, if they are humble, make them haughty, if they are relaxed, toil them, if they are united, separate them.” – Sun Tzu

Using an indirect approach also has another huge advantage: it helps eliminate approach anxiety. After all, you have nothing to lose by talking with others in the VC’s group, because you want nothing from them .

Approaching with confidence is just one obstacle you will have to traverse; the really hard part is what you do after you get a VC’s attention.

Continuing with the PUA theme: another important concept I learned was “how to DHV.” This common PUA term stands for “demonstrations of higher value.

For example, if you approached a woman at the bar successfully, your next task would be to demonstrate value in order to keep the ball rolling. If there is no incentive for the woman to continue to invest in the interaction, attention dries up, and she either gets bored or rejects you completely.

Keeping the interest alive can be done in many ways.

Through social proof—show the VC right away that your startup has the attention of other suitors.

Poke fun at the VC. If you can come up with a funny and lighthearted jest at the VC’s expense, you might get him or her laughing. Laughter is always a good way to break down my shield…ahem, “VC barrier” and be more receptive to your pitch. For example, “I love your tie…I think it would look better on me though!”

Tell an emotionally charged and engaging story right away. One of the first things I ask when conversing with a potential investee is, “What problem are you trying to solve?” In most cases, I get long-winded spiels filled with technical jargon—not cool! Just tell me a good story about how and why you came up with the idea. Maybe you were on the crapper one day, and a moment of inspiration came over you. Or you had an accident that gave you an idea.

Whatever you do, avoid long-winded pitches. You’d have better luck just coming up to me and saying “Gimme all yo’ money!”

So far you’ve managed to approach the VC indirectly and confidently demonstrated value; now what?

Body language and tonality: these are crucial. You might think your pitch is the most important thing, but having the right body language is the key to really selling it. After all, most communication is done non-verbally.

Always approach with a smile. Doing so telegraphs your emotional state to the group and serves to disarm them.

Never tap people on the shoulder to get their attention—it startles them too much.

Keep your hands out of your pockets or behind your back. Being more jittery than a crack addict shows too much nervousness; so stand with the poise of a soldier. And most importantly, be animated. I don’t want to feel like I am hearing a pitch from HAL 9000.


Move your hands and arms as you speak (like the stereotypical “Italian talk” but toned down slightly). It lends more gravitas to your dialogue, and listeners become more engaged.

Talk with passion. Have pregnant pauses in your dialogue from time to time, because this adds more drama and emotion. Plus, it has the added benefit of helping you eliminate filler words like “so” or “you know” at the end of your sentences.

Speak slower than usual. I cannot emphasize enough how important it is to speak slowly. Not only does it produce a hypnotic effect, you actually use less material in your pitch and force yourself to state the most salient points.

You should also maintain a fair amount of eye contact.

Lastly, use kino. Kino (short for kinesthetic) is another PUA term used to describe the act of touching someone in order to build comfort. Think of why we shake hands: it is a way to establish that you are friendly and not a threat. Sometimes a light pat on the arms of the person you are speaking with is enough to gain the desired effect.

Just remember this: VCs need you as much as you need them. Level the playing field by becoming a man/woman of value. Find your swagger. Be memorable. Be insatiable. Let the world know why you are the best entrepreneur out there.

Reprinted by permission.

Image credit: CC by Jirka Matousek

The opinions and views expressed at or through this website are the opinions of the designated authors and do not reflect the opinions or views of AlleyWatch.

About the author: Jay Deng

Jay Deng is an angel investor and venture capitalist. He invested in two companies whose exits topped $800 million. He is also the CEO and founder of Diva For Less.

You are seconds away from signing up for the hottest list in New York Tech!

Join the millions and keep up with the stories shaping entrepreneurship. Sign up today.