What being hopelessly single taught me about pitching tech Celebs

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.

  • http://twitter.com/hello_emily hello_emily

    Compliments on a fantastic article - I’m not single or a tech entrepreneur, although I am a serial networking event lurker, and it rings true for many situations I find myself in.

  • http://twitter.com/RedRussak ‘Red’ Russak

    What about advice for red belts? Where are we supposed to scroll? ;) 

    • Anonymous

      Ha, you’re a black belt with Red flair for sure. No doubt you could teach us all a thing or two ;)

  • Cascadefreeheeler

    Good stuff. I need to remind myself of this time after time.

  • http://twitter.com/arianna Arianna O’Dell

    This is a really great article and so true. While in Spain I’ve had to this for networking and to just make friends. One night I just said eff it, walked up to people in a bar, and then just said “I want to know people here.” Worked. Or as you said “”Step 1: Just walk the hell over and introduce yourself.”

    • Anonymous

      Your problem of meeting new people as you party and build startups in Spain is a problem I would love to have! :) 

  • http://www.facebook.com/profile.php?id=94500172 Kyle Kesterson

    Haha so true! During the pre to mid Giant Thinkwell era (pre-TechStars to post funding), I frequently resorted to just whipping out the iPad and blinding them with bright colors, drippy tentacles and dirty diapers (corollary: having my work speak for me). One thing to keep in mind, if it’s not something that just comes naturally, is people will respond more to passion and enthusiasm than a half to even fully baked idea. Chances are that due to inebriation, distraction or whatever else is going on in those high energy situations, you probably won’t be able to even articulate your vision so crystal clear that gets the other excited and leaves an impression, more so that you come off as the kind of person that would awesome to just be around and even work with. 

    One thing I learned during TechStars is that EVERY TIME you are out talking to people, whether it be an obvious networking event, standing in line for a sandwich or talking to your friend’s barber**, you are marketing yourself and your product. Keep the energy high and positive. You never know which random conversation could open up the next door.

    Great article Donald!

    ** = A friend’s barber got us an introduction to John Stamos for Raising Uncle Jesse

    • Anonymous

      Thanks man! You’re definitely the archetype of what this looks like when done well (and seemingly effortlessly). And +1 on being sober. While I love to let loose and party, I walked up to both Hammer and Rose stone cold sober. Luckily I had packed extra pairs of underwear on those trips…

  • http://knudge.me Tam Le

    This makes a lot of sense.  I don’t know why I never made the connection between pitching/networking and trying-to-date before.

    One other thing I’d like to point out – in both the bar scene and perhaps the VC scene – at any given bar there will always be the one person attracting most of the attention.  I like to ignore said person, and instead find the low key person that’s hanging out in the corner being bored.  You’ll be surprised at the number and types of people you’ll meet this way.  

  • http://procause.com/ matthewhughes

    “But with each rejection, beliefs #1 and #2 became less false.”

    I think the more you pitch your idea the more you believe in it.

    Being rejected can almost be reassuring.

  • http://www.funkmeyers.com Otis Funkmeyer

    really nice article

  • http://www.funkmeyers.com Otis Funkmeyer

    really nice article

  • http://www.twosides.co Jono Lee

    Great article! I conjured up the courage to pitch Ashton Kutcher at Startup School. Even though he seemed to like what I was doing (http://www.twosides.co) and asked for my info, I forgot to ask for his. An extremely dumb mistake on my part!

    • Anonymous

      Jono – I just checked out twosides.com and it looks awesome. Also, that split suit/shorts outfit is amazing. That’s what one friend of mine would call “pull networking” (vs push). :)

      • http://www.twosides.co Jono Lee

        Haha that’s true, I definitely got a lot more “So what do you do?” inquiries that day than usual. Thanks for checking out TwoSides, and good luck with Giant Thinkwell!

      • http://www.twosides.co Jono Lee

        Haha that’s true, I definitely got a lot more “So what do you do?” inquiries that day than usual. Thanks for checking out TwoSides, and good luck with Giant Thinkwell!

  • http://twitter.com/meanJim Jimmy Lee

    I like this article a lot, not because of how well written it is but because I can relate to this. If you’re going to learn to be a good salesman / or learn to pitch. You have to be ready to fail and get better, and accept that’s just part of the fun.

  • http://www.matthewshobe.com mshobe

    Best thing I’ve read for entrepreneurs to internalize since FAKE GRIMLOCK’s “Minimum Viable Personality” guest post on A VC. Well played, Donald.

    One other ‘corollary’ I’ll add to the general courage-building process required to walk up to some luminary and lay your pitch on him/her: taking advantage of customer support channels. If someone notable or just plain interesting registers for your product, asks for help with an issue, or offers a feature suggestion, be sure to reach out to them and find out why they’ve taken notice of your work and what you might do to get them more involved in your development/feedback cycle. a) they’ll probably be delighted to get a response, since so many companies still fail to engage 1:1; b) even if they don’t have anything to say/offer now, there’s always later. Sometimes, someone who isn’t a known quantity today will become a major one for you tomorrow – and they’ll remember your extra attention.

  • http://pulse.yahoo.com/_JGVLKJIQZQO27YBT6EGNRRLBQI Crash

    I’ve always been a numbers guy and people should always take rejection well. You should have the mindset that every time you get rejected, it just means you’re closer to someone giving you a shot and saying “yes”.

  • Dan J Mckee

    This article has little to do with pitching, it’s about having the guts to go up and say hello. I doubt your pitches with Rose or Hammer will go anywhere, but like you said, nothing lost and nothing gained. Essentially you’re playing a numbers game, which is absolutely better than doing nothing, but overall probably not the smartest way to pitch.

  • Tgowland

    Great article Donald!

  • Anonymous

    Depending on the person’s level of celebrity or perceived self-importance, it can sometimes be hard to break through and get their true attention. Some of the more effective impromptu pitches for cash that I’ve seen involved having an already created product and basically forcing them to check it out. Because “celebs” get pitched a lot, being able to cite some stats that indicate a high level of interest among people (reducing their risk) are also valuable. If you can quote some positive traffic stats for example or positive Facebook stats (a lot of startups use the companies listed at http://www.buyfacebookfansreviews.com to launch with more Facebook fans) you might be able to get their attention a bit more. But depending on what type of product you are building, you can often get profitable without relying on outside cash or investors. The true value of tech celebs are the connections you need to get media attention because so many of these media entities get so many pitches every day you need some personal attention to break through that barrier: but sometimes you just don’t need it if you create a solid business model that doesn’t rely on these types of breakthroughs.

  • http://theblakefirm.com Austin Business Lawyer

    This is great advice.  I’d extend the dating analogy further to say that people often talk about themselves too much when “getting to know” someone else.  Corollary: People place too much emphasis on their own idea/invention/business.  Instead, reach out to what is important to an investor: the pain/need/problem that your idea/invention/business solves.  Emphasize this pain/need/problem — it’s what’s truly interesting, or not interesting to an investor.  If you don’t connect with an interest or desire in your date/investor, it doesn’t matter how great you or your product are, you’re not getting to second base.

  • http://twitter.com/RazoGT RazoGT

    It’s so true, I couldn’t agree more with you Donald. At the end of the day, “sack it up” and get at it.  Hell, you are only going to get better at closing the more you do it.

  • http://twitter.com/grmeyer Greg Meyer

    Great article! I’d add one suggestion once you get contact info -> offer one thing that you are going to do to follow up, set a time for it, and actually do it.

  • http://twitter.com/golikebright LikeBright

    This is a fantastic article! I love it. Donald, you should be writing for the LikeBright blog …

  • https://illuminateme.posterous.com/ MaX Song

    Fantastic article Donald, this confirms something that I’ve been
    thinking about for a while, the difference, or therefore lack of, of PUA
    and networking. Both are you trying to sell yourself or an idea you
    have to other people, in hopes of building connections. Just so happens
    that the latter can help you with the former.

  • https://illuminateme.posterous.com/ MaX Song

    Fantastic article Donald, this confirms something that I’ve been
    thinking about for a while, the difference, or therefore lack of, of PUA
    and networking. Both are you trying to sell yourself or an idea you
    have to other people, in hopes of building connections. Just so happens
    that the latter can help you with the former.

  • http://twitter.com/vjtorres11 Victor J. Torres

    Wow, you really hit the nail on the head of the “mechanisms” or excuses I’ve become totally accustomed to using. I’m pretty sure these things are just another case of “practice makes perfect.” It’s a matter of convincing yourself to just wing it and give it a chance.

  • http://twitter.com/vjtorres11 Victor J. Torres

    Wow, you really hit the nail on the head of the “mechanisms” or excuses I’ve become totally accustomed to using. I’m pretty sure these things are just another case of “practice makes perfect.” It’s a matter of convincing yourself to just wing it and give it a chance.

  • http://twitter.com/laurenkmcleod Lauren McLeod

    Bahaha! I love your last point of advice, “it all starts with starting – walking up to someone important without losing your nerves and throwing up all over them.” Very true, I find a glass of wine usually helps to loosen up those knee joints.

  • http://twitter.com/laurenkmcleod Lauren McLeod

    Bahaha! I love your last point of advice, “it all starts with starting – walking up to someone important without losing your nerves and throwing up all over them.” Very true, I find a glass of wine usually helps to loosen up those knee joints.

  • http://twitter.com/laurenkmcleod Lauren McLeod

    Bahaha! I love your last point of advice, “it all starts with starting – walking up to someone important without losing your nerves and throwing up all over them.” Very true, I find a glass of wine usually helps to loosen up those knee joints.

  • http://www.venturehuntli.com Christopher Erckert

    I like to close with. “Does that sound of interest to you, or someone you know? wait for response. If positive, “What is the best way I can keep you in the loop of my progress”. If negative. “Thanks for your time, is there anyone or any type of venture you are seeking? Just let me know the best way to forward such information along.”

    But Donald is right, you need to let the fear of rejection go to them and chat it up.

  • http://www.thorholt.com/ Thor Holt

    As a used to be a social invertebrate & now not so much > here’s what worked for me. 
    1) Remember, “If I don’t ASK they can’t say YES” 
    2) Have a crazy hippy parent who named you Thor (any God names will do) 
    3) Ask for discount “because..” Whatever, just use ‘because’ OK, and do this everywhere, you’ll grow BIG brass balls that way and have flirtatious fun. I’ve had discounts(& freebies) on butternut squash in grocery stores, car repair bills, clothes, lattes…. 
    And hey, don’t be so precious about looking like a fool. Get over yourself! ;)

  • Farhad Tarapore

    Walking over and introducing yourself is fine. But what after that? I find it absolutely impossible to do small-talk or chit-chat. It becomes more like an interview with one person asking questions and other one responding. After 5 minutes it becomes totally awkward and boring.
    The bottom line is you really can’t pitch anything if you are NOT genuinely interested in the other person. Either that, or you’ve got to be really good at faking interest.

  • http://twitter.com/_huntr David Hunt

    ‘Top Blagger’ : a term used to in those situations where ‘winging it’ doesn’t even come close to describing how you managed to get through a pitch…. 

  • http://twitter.com/TiklMeCorp TiklMe

    Excellent article … I actually built a FaceBook game called TiklMe to make flirting less terrifying.  Anyhow, great points … I’ll have them in mind when spreading the word about TiklMe!

  • http://twitter.com/TiklMeCorp TiklMe

    Excellent article … I actually built a FaceBook game called TiklMe to make flirting less terrifying.  Anyhow, great points … I’ll have them in mind when spreading the word about TiklMe!