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MC Hammer
Kevin Rose

Disclaimer: If you’re already the black belt ninja networker type, skip to the end and share your tips. If you’re still a white belt, I hope you find this useful…

I will pitch anything to anyone, just about anywhere. Recently, I’ve managed to pitch both MC Hammer and Kevin Rose on different projects. Both settings were crowded and inopportune. I wasn’t prepared and they weren’t expecting me. In spite of that, both guys listened, showed interest, and offered their contact info for a follow-up.

You can do this too. And guess what? You don’t need a slide deck. You don’t need a meeting. You don’t need a “Demo Day.” You don’t even need to be sober. You just need to be in roughly the same place at the same time. How does it work?

Walk over

Pitch them

Ask for their contact info

If it’s really this simple, why is everyone so bad at it? I think it’s because people practice the wrong things.

Donald DeSantis

People practice their pitch ad nauseam but never practice walking over to strangers and striking up a conversation. The result? They go to a conference with a solid pitch and then wait for someone to come say hello. (Hint: It probably won’t be someone like Dave McClure or Michael Arrington.)

After suffering from that pattern for years, I learned a new approach in the most unexpected venue.

Step 1: Just walk the hell over and introduce yourself

Am I an extrovert by nature? No. Did I get pitch grooming at TechStars? No. Do I have some fortuitous chemical imbalance? No fortuitous ones, regrettably…

I learned to walk over and strike up conversations in the most forbidding and merciless training ground known to man. I learned by getting phone numbers from attractive strangers at bars.

Years ago, before I met my incredible wife, I was hopelessly single. My “game” consisted of going to bars and hoping women would come strike up a conversation with me. They never did. (This was my “meet women” strategy for an embarrassingly long time by the way.)

One evening, while sending magical “talk to me” vibes around the bar, I was struck by a profound (if obvious) realization. If I wanted a stranger’s phone number, I would have to walk across the bar and ask her for it. While this was clarifying in its simplicity, I was devastated. Why? Because I held a few beliefs about what it takes to get a phone number from a beautiful stranger.

You had to:

Be a great dancer (tech corollary: slick demo/pitch)

Surround yourself with a coterie of other attractive women (tech corollary: a coterie of other investors or “cool kids”)

Have charm like Hugh Grant, with a face like Jude Law (tech corollary: Have charm like Hugh Grant, with a face like Jude Law)

A face like Jude Law's doesn't hurt when pitching

I was/am a horrible dancer. My coterie consisted of equally love-starved guys wearing mustard stained t-shirts. I have questionable “charm” and have never been mistaken for Jude Law.

Discouraged, but undeterred, I outlined a new set of beliefs:

1) I have nothing to lose.

2) Rejection? Ridicule? No sweat. I am built to handle that.

3) Even though #1 and #2 are totally false, I’m foolish enough to do it anyway.

Number three is the only one I really believed at the outset – that I truly am foolish enough to throw myself to the wolves. Fortunately, it was the most important belief.

I didn’t get the first phone number I asked for, nor the second. In fact, the first number probably came somewhere between tries five and ten. But with each rejection, beliefs #1 and #2 became less false. I also become much more comfortable at getting a conversation rolling. Mastery through repetition.

So you’re ready to pitch Ashton Kutcher and Will.i.Am at SXSW, right? Probably not. If you’re anything like me, you’ll talk yourself out of it with completely reasonable excuses:

1) My pitch isn’t solid (corollary: I’m not a good dancer)

2) They’re already swarmed (corollary: They’re surrounded by Jersey Shore meatheads)

3) The product isn’t ready to share (corollary: I have a huge zit on my nose tonight)

4) I have to go to the bathroom (corollary: I have to go to the bathroom)

In fairness, influencers are typically swarmed and you probably will have to pee. But there’s an effective test that keeps me honest: “If I could pay some badass person $10 to deliver an enthusiastic pitch of my product and ask for that influencer’s contact info, would I cough up the $10 bucks?”

When the answer to that question is yes (it usually is), it’s a pretty good sign that my reasoning is bogus. What you do at this point is up to you. I try to cue up “Eye of the Tiger” in my head, cinch up my Depends, and put on my game face.

Step 2: Pitch baby, pitch

There are lots of great articles on pitching. My advice is simple:

Keep it short.

Humor is risky, but can work wonders.

Have your app/website/mockups already cued up on your phone in case they want to see your product. Don’t make them wait for it to load.

Step 3: You actually have to ask for their contact info

You still gotta ask for their contact info. Don’t wait for them to offer it up unprompted. When in doubt, try something like this:

“We’re moving fast, and I’d love to keep you posted on our progress. What’s the best way to do that?”

Done. If they deflect, you can make the call about whether to press harder. Most of the time it pays to be gracious and move on.

Final thoughts

The thing people struggle with most when pitching isn’t the pitch itself. It’s gathering the chutzpah to walk over to some industry star and introduce themselves.

When I’m feeling timid, I remind myself that no one’s going to walk over to some attractive stranger at a bar and tell them how interesting I am.

No one’s going to walk over to Ron Conway and tell him how brilliant I am. Those things are my responsibility despite my half-baked pitch, my mustard-covered comrades, the zit on my nose.

Practice and repetition are what’s worked for me. I’m sure it can work for you too. But it all starts with starting – walking up to someone important without losing your nerves and throwing up all over them. Getting the contact info is second order importance for the first few. Focus on keeping your lunch down.

While this has worked for me, I definitely don’t know everything. So what’s worked for you? What stories do you have on reaching out to tech celebs and industry shakers?

Donald DeSantis works at Seattle startup Giant Thinkwell. You can follow him on Twitter @donalddesantis.

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