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What being hopelessly single taught me about pitching tech celebs (geekwire.com)
184 points by iseff on Nov 6, 2011 | hide | past | web | favorite | 48 comments



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.


This is a tough thing for founders. I was in this situation earlier this year after I won a ticket to Google I/O. One of the events was a Google Ventures mixer, which turned out to be a "speed-dating" event. I was excited to meet Joe Kraus, who gave my favorite Startup School speech ever, but what to do in this format? Launch into a cooked-up pitch? But I wanted to talk to Joe, not use him for target practice based on his job. But wasn't that kind of what I was expected to do? Still, what a borderline-presumptuous missionary tack to take with someone I respect. But wouldn't I get over that knowing teammates were counting on me to get us funding any way we could?

At last, I decided to skip the pitch, chatted very pleasantly with Joe, got some great advice and his card. In retrospect, that was really about as much as I should expect in a five-minute sit-down. He seems twice as much of a great guy as I thought he was. The pitch can wait until the next time we cross paths or it's been a lot better tested. But I better recognize now how awkward these situations can get.


Probably the optimal plan would be to engage the investor and let them draw the idea out of you by asking questions. Not just because this is less aggressive, but because it's more efficient. Preformulated pitches are usually so bad that it makes my head ache trying to figure out what the company does. If I could just ask questions I could probably narrow it down pretty rapidly.


The 'What do you do' question almost always comes up. Or the 'what are you working on?' question. That's when you can say your few words about what you do and what you are working on. If the other person is interested they might ask a question. You say something like:

"I'm a app/web developer who just finished contracting at the fastest growing company in the world making apps for fortune 100s and am now working on a start up doing Travel Guide-Apps."

Their eyes may glaze over half way through your "I'm a web developer..." at which point you notice this and drop it, ask them what they do, or ask them some other question.

Anyway, I guess that is basic 101 conversation techniques.

A fun game I used to play with friends in bars/clubs was introducing someone else. My friend would pretend to be a french student new to the city and I was introducing them around. Got into some very funny conversations with people... especially when they realized what the game was.


I think you could seriously improve your 'What do you do' answer. If you'd simply said "I develop travel guide apps" you probably wouldn't get any eye-glazing and in all likelihood it might even lead to an interesting conversation about traveling and favorite destinations. Don't brag about how awesome you are and don't get into details about who you work for or how awesome they are. Simply state in as high-level terms as possible actual real world problem you are solving, and don't worry if your short answer isn't technically correct. If they care you can clear up any confusion when they ask for more details.


Thanks for the comment, Paul. Blog posts are funny, b/c you have to boil down a bunch of complex ideas into something people can grok while skimming. I actually don't like the word "pitch" or think of myself as someone who really pitches things very well at all. But it does describe sharing your ideas with other people, capturing it in a single word. A more accurate description would be "sharing your vision" or something similar.

If there's one thing I've learned over the years (whether meeting new startup people or trying to get a date) it's been the "don't be a douchebag" rule. Treat people like people. The best "pitch" is actually not a pitch. It's authentic, where you're talking to someone who you honestly believe will be interested in what you're doing, and you're sharing something you're sincerely excited about.

The last person you want to be is one of the "Jersey shore meatheads" trying to dry hump some poor woman out on the dance floor (to harken back to my earlier analogy). :)


It is actually how most of the world works: you tend to remember people you meet in person (versus those who cold email or call you), and as long as the pitch is not canned or scripted (people who do this well can be very conversational about how they describe it), it can lead to a follow-up meeting and further discussion.


I'm curious as to how often this happens (in person). Is this a weekly occurrence?


Just take a look at the TechCrunch Disrupt conf videos with pg and other VCs. They get pitched constantly when it's totally out of context and inappropriate, eg when they're on mic to ask a question or participate in some contest. Granted this was a startup event, but you could tell that these people would pitch like this at any opportunity they see upon recognizing a VC.


In your case the "pitch" would be an intelligent conversation. The traditional pitch wouldn't be a pitch because it's ineffective. The article only talks about anxiety but the importance of iteration is in there (he got the first number after 4 or 5 tries) and I'm sure his pitch was more natural than your typical "deer running towards headlights" kamikaze pitch.


I think part of YC:s success is that you take applications online. One doesn't need a lot of networking and pitching skills to get into YC, just a great team, ambition and some kind of idea. That means you get startups that other investors will never see.


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.


I look for cues, such as who is funding you

Someone has to go first, no? Why do you trust rival VCs more than your own judgement?


Either I'm mistaken, or you do not know who you are answering to.

Mystalic is an editor at Mashable, not a VC. Therefore, when asking "who's funding you" he's not looking for rival VCs, but as he said, for cues. That does not, however, really invalidate your point of him making is own judgement instead of filtering by VCs.


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.


This also works in the dating game where you approach indirectly by striking up a conversation with the less attractive friend.


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


Similarly, whenever anyone cold calls me or knocks on my door to sell me services I don't want I ask for a brochure to "read over" later.


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.


I guess the question for those of us who aren't inherently interested in people is how do we build such an interest, curiosity, and love for everyone? You can't just read Be Here Now and suddenly be enlightened and feel one with the world.

(The question is not exactly directed at you since you seem to naturally have such an interest.)


I used to be a curmudgeon until my early 20s, wondering how everyone could be so dumb. Then, enlightenment! I learnt I didn't know everything.

I am just curious. Everyone acts rationally from their point of view. Why do people do what they do? What makes them successful? Failures? What is their take on living? Most people are passionate about something, so tell me about it. I'll learn something new.

I spent a lot of time learning how to actively listen, not just wait for an opportunity to jump into a conversation with my own immature opinions. (I have many.) I am not afraid to ask dumb questions in an effort to learn. I have no fear that people will think I am stupid. Actually, asking questions makes you look like a genius.

Caveat: There are some people who lack the spark of life. I don't spend time with them.


I love this response.

1. Listening, really listening, is really hard. Start by trying to listen to those you seem to have an issue(s) with! Really try to have an open mind and see things from an alternate perspective. Surely, you must have some level of interest in people you see. Why did he decide to get 1000 piercings? Why is s/he homeless? What drives this person to wear a suit every single day? .... Look at the things that you judge, and try to find answers that may not be so obvious as to why they are the way they are.

2. "I learnt I didn't know everything" -- this is pure and simple, but if my own experience has any relevance, it won't click with a number of people. I was smart enough to know that I didn't know everything when I was pretty young. But somehow, I really didn't "get it" -- I thought I was open minded, but I really wasn't. It wasn't until life beat me up pretty good that I finally "think" I get it. At least I hope I get it, and I feel like I do. Which leads to...

3. "Everyone acts rationally from their point of view" -- It took a very, very long time for me to understand this point. It took a lot of humility, pain and suffering to really open up my mind to why people do what they do. I believe MOST people make choices with good intentions. From the outside, it might be hard to understand those intentions. The challenge, or for me, the interest, comes in understanding the perspective that drove a particular decision. This goes back to "two sides to every story" -- and I've seen enough stories to know that both sides have strong convictions that they are correct and right. If you aren't fundamentally interested in people, then try to get interested in figuring out why they do what they do, especially when it is at odds with your own bias.


Most people are passionate about something, so tell me about it.

That's my sticking point: in situations referred to, the person in question all too often isn't prone to discussing what he _want_ to discuss, but what his fans do. How to, as a random face wandering up as so many do, can one elicit some fragment of "say, what do _you_ want to talk about or do?"

The nuance struck me when meeting (as just another face in the room) Steve Reich and Philip Glass. During a talk, Reich lamented that everyone wanted to gush over his early works, which he made clear he viewed as immature - not bad, but something he has moved far beyond. Able to stand nearby someone's hallway chat with Glass, I was struck by how _much_ the two had to talk about, how the other person wasn't anyone the great composer knew, and how I had absolutely nothing to offer/initiate in conversation despite a desire to do so and an ability to work a conversation well _once_it_started_ on some point - but alas I had no point to start on.

To wit: when opportune, I want to say to great/famous person X "so, what might _you_ want to talk about?" but such phrasing is inane.


A few years ago my mother helped organize a literature festival and at the closing banquet was seated next to a famous author with several critically acclaimed bestsellers to his name. My mother introduced herself and added "I have to admit I've never actually read any of your books". "Excellent!" the author replied, "that means we can talk about something else". And they spent the entire evening having a really great conversation about all manners of topics. My mother said she could really tell how excited he was to get a chance actually talk about something other than his books.


Conversations are back and forth. They will make it obvious what they are passionate about by their answers. Start with easy questions. Talk to them about anything. Have you been to this kind of event a lot before? What did you think about the speakers? Be aware of what sparks them up.

I'm not trying to pitch people except when I am so I don't feel a lot of pressure to get people to instantly like me. I'd rather have a great conversation. The pitch comes after I know what their current needs are.


That's good advice, thanks!

It's hard but I'm trying to be genuinely curious about others. There's nothing worse than someone pretending to be interested, asking questions and then not really listening to the answers. I try to avoid being that person. One thing I try to remember is that everyone has something interesting to say if you push the right buttons.


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.


Things are complicated. Beware of the potential phonyness lurking there. "Instead of making a business offer, pretend to be friends long enough so that the other party will (maybe) want to make business with you."

Cool and all, but sometimes a pitch is just a pitch, and a fuck is just a fuck.

Also: personally I would never start a business with a friend I really cared about. Never. It's just like having a "friend with benefits": it can go perfectly or it can be hell on earth.


""Instead of making a business offer, pretend to be friends long enough so that the other party will (maybe) want to make business with you."

That's not what I'm saying. Rather, I'm talking about cultivating a network of friends in and around the business. If one of those friends happens to be an important person, great. If not, great.

It's possible to have a long-term agenda and not to be mercenarily seeking things from people along the way. In fact, the less you do the latter, the better. Ironically enough, you'll probably have an easier time getting help from people if you're not solely trying to get help from them.

To refer back to the girls-in-bars analogy: you'll have an easier time getting laid when you're not trying hard to get laid. When you're simply trying to have a good time and meet interesting people, getting laid is icing on the cake. It's not the goal, but when it comes along, it's a bonus.


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.


Maybe girls don't like being hit on by the wrong people, or in the wrong way. But ultimately they do want to be approached by the right guys, or they wouldn't keep on going to places like bars where one of the main selling points (unless it's a gay bar) is meeting people of the opposite sex.


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.


Agreed. While most people (incl. me) can benefit from moving outside their comfort zone and be more assertive, you still have to use judgement/discretion. It's a challenging line to tow. I've got it wrong at least as many times as I've got it right. I'd like to think that my instincts in this regard have improved over time.


i was working for MSFT a while ago, and at every conference i showed up, people totally started pitching me all the time (i wasn't in M&A, so why even?). i loved being approached and hear new ideas, but fact was, 9 out 10 things were incredibly sad and boring, produced by crazy folks. i mean, i feel bad for their passion and me not getting it, but a lot of things just were far from any success. and that made me lose interest in seconds, which brings me to the point that it was less about being approached (what's a minute or two), but more about hearing a lot of bad ideas. for a good idea? i'd listen an hour if I have the time.


And yet it is also fashionable to say ideas are worthless. so yeah, here's my great idea.


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."


Hi, I've been an HN lurker for a few months but finally signed up today just to inquire about mentors when I saw your comment. I am a complete beginner when it comes to startups. In fact, I happened to stumble into my niche rather accidentally. How do I go about finding great mentors or at least a group of like-minded people that I can learn from? If it helps, I'm currently located in NJ about 45 mins from NYC. I apologize in advance if this is a strange venue to ask this type of advice. Thanks!


I searched Bing for "New York Tech Startup Calendar" and got this:

http://startup-ventures.meetup.com/cities/us/ny/new_york/

Just start attending events, smiling, and introducing yourself to people. Make sure you are not shy about asking for what you are looking for. For example "I'm just figuring this startup thing out. I think I've got some great ideas but I don't have any mentors. If you know of any one I could talk to that would be great."

Good luck!


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.


Funny. I have recommended 'The Game' by Neil Strauss to more than one person for reasons beyond just meeting women. Learning how to start and manage a conversation are powerful tools.


I wonder how many "hacker players" hang out on HN? :)


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.


There seem to be an infinite number of parallels between 'the game' and networking in general. I worked for 4 years as a full-time dating coach, and many years before that trying to get my game up to scratch, and the benefits in contacts, in rapport building, in sales arenas, in any area where I need to present, are immeasurable.


>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.

The key is to understand that neither women, bartenders nor venture capitalists are homogenous hordes that can all be handled with the same neat little set of well-defined procedures that you read in a book or hear at a seminar.

Especially not women, what with them comprising half of the planet's population.


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.




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