What being hopelessly single taught me about pitching tech celebs

Maybe my case is unusual because YC takes applications online, but I don't like it when people walk up to me and "pitch" me by reciting some preformulated speech about their startup. I can almost never understand what they're talking about. And it makes me feel like a target, in much the same way it probably does to women when guys walk up to them and recite preformulated pickup lines.

The unit of conversation with a "tech celeb" need not be a pitch. I'd suggest trying an ordinary conversation instead. I don't know about other people, but it would definitely work better with me.

Coming from the point of view of somebody who gets pitched daily...

I can barely distinguish them from each other.

Sure, I'll give you my card with contact info, but it doesn't mean I will be interested when I get the email.

Yes, you did more than most people and had the balls to approach me. Great. But that won't fix a mediocre product or a product I'm not interested in. I'll just end up ignoring your email.

I look for cues, such as who is funding you, your background and whether you got an introduction from somebody I trust. These things are my filters to finding the stories and startups that matter.

Beyond that, I agree with PG: I prefer ordinary conversations. Again, the people I know and find genuinely interesting are more likely to catch my attention when the time comes to pitch me.

So hypothetically if you have a very busy person who is mobbed by a lot of cold pitches, they might have a bit of pitch fatigue and assume that anybody cold pitching them is likely about as good a fit as the average cold pitcher, which is to say "total waste of my time." That very busy, selective individual probably has friends who are less mobbed by pitchers. Those friends might even be flattered to hear from you. Pitch them, with the goal of convincing them your startup/story/invitation to dinner and a movie/etc is so attractive that it is worth giving a warm intro to their friend. A warm intro in the Valley appears to be frequently a short two-sentence email: this is how I know X, here's why he's valuable to you, you guys take it from here.

This is how the real world works, over and over again.

I, too, used to suck at approaching women at bars (I still do!). Rather than polishing up my pickup game, I adopted a different strategy: be interesting. Go to fun parties. Throw some fun parties. Become known as a cool person to hang out with, which results in more invitations to more parties. Create your own momentum.

I suppose the tech-industry corollary here is to do some agenda-free networking, and build up an agenda-free network. You may have a hidden agenda, and that's fine, but push it to the way back of your mind for now. You need to spend time building up a circle. Where to start? If you're in the Bay Area and working on a startup or a personal project, I'm sure you know at least 5 or 10 other folks in the same boat. Start getting together. Set up a weekly dinner or drinks. Start finding out about other peoples' dinners and drinks. Socialize and be interesting. Help other people without any expectation that they will help you.

This is a slow game, played over a longer term than many people are comfortable with. But it's a more organic way to meet and "pitch" people. I'd much rather find a way to become friendly with Big Investor X than find a perfect 30-second pitch for a chance encounter with Big Investor X. I can always pitch a friend, after all, if a bit down the line.

"But none of my friends is interesting / knows anybody cool / has any different friends outside our group."

Time to diversify your social circle, then. Reach out and connect people from different stages of your life: childhood friends, college friends, work buddies from former and current jobs, interest-group friends, and so forth. Go to mixers and meet new people, too.

All of this may sound patently obvious to some folks here, and if you're among those folks, awesome. Just know that this stuff didn't occur naturally to me, and I bet a fair number of people are built similarly. I'd always struggled with the apparent phoniness and strain of "networking," until I learned why: I was trying to compress a long-term process into short-term transactions. It felt unnatural because it was unnatural. I was always approaching people out of the blue and asking for something. That's not a winning strategy for becoming liked and getting helped. You've got to be doing things for others before expecting others to do things for you.

Here is my email address so I can escape this painful conversation. It will be much easier to ignore your email.

My title is literally Chief Handshaker at FreshBooks. I wheel and deal for a living.

When walking up to people randomly, I find it is immensely helpful to be genuinely interested in people. They will often pay you back the favour by being genuinely interested in you afterwards.

To be honest, I do what I do because I love people. They are endlessly interesting. I don't do it to build my Twitter follower count.

If you walk up pitching they will just turtle and get rid of you. Have faith they will ask you about you in due course.

From the comments here, I infer, VCs probably don't like being pitched unsolicited. Girls don't like being hit on. I have never pitched a VC, so i am basically theorizing here. The trick is not in approaching them, but approaching them in a way which does not activate their natural defense mechanism. If you come across as interesting the girls will give you attention. Its better to lower their defenses with an approach that they don't expect.

Great article.

The first thing I do when mentoring noob entrepreneurs/founders is ask them about their networks.

"How are you growing it?"

"Who are your mentors?"

"Who are your mentees?"

"Who are the big-wigs in your network?"

I have found, much to my surprise, given that I'm a "black belt ninja networker type" (apparently;per the article) that people haven't really given much thought to these questions.

They know (or get the sense) that having a strong network is important but they've never really worked on building it.

This article provides some good insight on how to build your network. Specifically it makes it clear that in order to build your network you MUST NOT BE SHY.

It also makes it clear that it's work.

As I like to say: "Building your network requires, well, that you build your network."

I remember meeting Mike Arrington at TechCrunch Disrupt, and he said that he "hates being pitched to [unsolicited], I'll probably think its a bad idea. I thought twitter was a bad idea.." Not sure how that changes with CrunchFund.

My guess is that some Angels/VCs are way more approachable than others.

The price tag is key: if I'd pay someone ten dollars to make my pitch...

Ten bucks? Whether its a phone number I want or a pitch I'm making, ten bucks is way low. And if I'd pay a hundred for either, clearly I ought to suck it up and get in there ans get what I want.

Put a price on it. Makes you realize when you are just being a little bitch.

"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."

This applies to so many different areas of life that it should just be made a rule, if it isn't already.

getting good at "game" has led to improvements in almost every other aspect of my life, including pitching.

it's a tough thing to accept, but you outlined it pretty well. most things don't just happen. nobody believes it's the time, place, moment and right person to "risk" being declined, ignored or laughed at. and that's so wrong. people who succeed, typically, tend to be a bit more open than others. everything else is an excuse to hope for pure chance or being discovered. and in all reality, try it with beers, go to a bar, hit on a random girl, just to get started again. it will be really, really tough at first.

I agree overcoming "approach anxiety" is key to just about any goal that requires someone else to be attracted to you in one way or another - dating, investing, friendship, ordering a drink in a crowded bar, ....

However, the key to ultimate success in all of these is that the person needs to like you and respect you. Girls don't like guys that approach them and rattle off about how funny they are, how much money they make, and what a great lover they are. Girls respect guys who are confident and layered, not guys who throw all their cards on the table in a 30 second pitch in a desperate attempt to be liked. Bartenders will first serve patient, confident, respectful customers, not eager, aggressive douchebags flashing twenties and snapping fingers.

Not being a super-experienced investor or fundraiser, I'll leave the translation to investment pitches up to others, but I have a mixed reaction to this post. For most people, the hardest part of reaching out to others is shutting down the the internal chatter that talks them out of opening the door. How you conduct yourself afterwards though, is also incredibly important.

I suspect investors as a class try to grit their teeth and discount awkwardness and narcissism in the hopes of finding the next Mark Zuckerberg, however I also think being a genuine and likable person - which for the most part means genuinely liking other people - is a great path to a good relationship in this and any other circumstance.

Awesome! Not only is this good business advice for me but it also gave me some dating pointers which I, as a newly single, rusty, guy, probably needs. Thanks.