On meeting and pursuing.

March 13, 2007 — 8 Comments

I am awful at meeting new people. I withdraw inwardly, grow nervous and bite my tongue. Don’t get me wrong, the strategy serves me well at times. It’s an effective means of preventing youthful stupidity from shutting doors. But as I am quickly learning, that’s not going to cut it anymore.

At SXSW this weekend, I had to network for really the first serious time in my life. The first day was a wash, I walked up to people and lost my nerve. The nerdy creator of Techmeme–Gabe Riveria, a kid barely older than me who, honestly, I would have made fun of if I’d ever met at school–talked down to me like I was a child. I’m sure a few others put my card straight in the trash. But as the week progress, I began to hit my stride.

At a party outside the event, I was talking comfortably for the first time with someone, because they weren’t important to me. I ranted about Twitter–otherwise know as the cloud of dust preceding the horsemen of the internet apocalypse–when someone eavesdropping weighed in and disagreed.

Guy: “You just don’t understand the benefits of Twitter, it’s going to be huge.”

Me: “Are you from San Francisco?”

Guy: “Yes”

Me: “Do you play Second Life?”

Guy: “Yes.”

Me: “Then what the hell do you know? This is the problem with the tech community, they’re so insular, they don’t understand what normal people enjoy doing or how they live their lives. You are just wrong, my friend.”


From there, I had framed the terms of our relationship. I was the outsider who had perspective, and he was the slightly ignorant nerd. And accordingly, he had to impress me or I’d move on to someone who I respected. Indeed, he ended up being an important guy–and potentially a valuable Rudius contact–one who was trying to prove himself to me, instead of the other way around. Up to that point, in every single interaction I’d had there, I had been in his position, the timid little teenager bothering the somebodies.

I found my greatest success when I told myself that I could offer them as much as they, I. Even if it isn’t necessarily true, that perspective puts the two groups on equal footing. Even with Tucker, my initial pitch didn’t beg for a handout. My credentials and my ideas were stated boldly and up front. But my desire to learn was equally illustrated. That’s what so few of you understand–he didn’t take me on as a fucking charity case, but as an understudy who made his potential as clear as his work ethic.

These are notes I wrote to myself during the conference:

You cannot come to them as a 19 year begging a question. Demand a king’s ransom and you’ll be treated like a king. You need to be approachable–deserving of being approached, near them–as opposed to doing the approaching yourself. Don’t be timid, don’t grovel. You need firmness, confidence, assuredness.

You cannot, however, succumb to brashness. I may be 19 years old, but I am NOT 19. Self-control is key, do not–for a single second–believe your own charade. You fake it, until you make it. Acting important as you muster forces to become important. Think of Fastow’s banking strategy–shifting from account to account, emphasizing strength and covering up weakness. His fatal flaw was that he saw this as a sustainable practice, ethically and economically. No bullshit; this is only to compensate for the stacked deck.

I know nothing. Or at least a fraction of what I can potentially know. Do NOT allow this to go to my head. Remember to treat the uphill as declines and the downhill as inclines. Restraint, discipline, always. Rational conscious thought. They’ve served me well thus far, do not abandon them at the first tiny taste of success. If you do that here, it was all a farce, you really do become a novelty. That’s not to say it was a waste of course; all things become learning experiences. But do not spoil your early adopter’s advantage.

I think the key point is that no one pays notice to timid, especially the young and timid. Nor does anyone respect the bombastic, especially young ones. Like Aristotle’s spectrum dictates, excellence lies in the middle–in this case with confident coolness.

So as I’ve learned at SXSW, always appeal to a person’s desire to pursue. Make yourself the steal, even as you reach for their wallet. Project success and the prophecy will fulfill itself. Manifest your intended result in your current attitude and you paint an alluring portrait. Clearly this is a rather fungible idea that can be applies to all sorts of interaction. At the same time, never lose sight of “formlessness” and the fact that the strategy is DIRECTLY rooted in moderation.

Ryan Holiday

I'm a strategist for bestselling authors and billion dollar brands like American Apparel, Tucker Max and Robert Greene. My work has been used as case studies by Twitter, YouTube and Google and has been written about in AdAge, the New York Times, Gawker and Fast Company.

8 responses to On meeting and pursuing.

  1. It’s almost inexplicable how much you have it together at your age. I’m 26 and I just learned some crucial from you after reading one post after not checking your blog for several weeks. You are an inspiration. Your future’s bright, go buy some shades.

    Treating the uphill as declines and the downhill as inclines speaks volumes of your character and no one can take that from you. Keep it up.

  2. Thank you man. This is what I wrote down after running and reading The Mediations:

    As you race, it matters only have you behave on the hills. Downhill–did you resist brashness, exhibit more control and discipline here than on the straight-aways. Ignore your impulse and shorten your strides. Uphill–did you clench your jaw, look down once and then lift your gaze to stare directly in to its eyes. Races are won here and not there–where it’s hardest to speed up, not where it’s easiest.

  3. I agree completely with Jones. I just turned 24 and have really been going through very similar phases to Ryan over say the last 1-2yrs. Would have loved to have that insight/awareness at 19.

  4. What is the end game here? What future are you working toward?

  5. I have read most of your posts and to be honest I kinda of expected this to happen after you said you were going to SXSW. Funny thing though, the entire blog reminded me of that scene from Gladiator where Maximus and Promixo talk of Rome.

    Maximus: I will win the crowd, I will give them something they have never seen before.

    That reminds me, or atleast what I have read about you, that you’re able to take assignments and blow them out of the park. Kinda of like how Maximus takes a gladiator battle and converts it something he is used to, battles against the tribes in german. I could be way off and reading too much into your post but that is what I got from it.

  6. No you’re right and that’s funny because we were talkimg about that very line during the conference. I’ll post more about this later.

  7. I just Stumbled on this page. I’ve got two reactions:

    You appear to be starting from the perspective that you are engaging in social combat of some sort. No wonder you start by feeling inadequate and think that you have to puff yourself up to compete. You’re going to get much farther if you don’t play to win. You have far more to offer than your expertise and your experience. You don’t have to bullshit anyone. If you want to engage people and make connections, prepare questions ahead of time. Keep your mind open, it’s probably what got you where you already are.

    Your argument about Twitter reminded me of arguments I overheard in the early 90’s about the web and email, and in the 80’s about VCRs and CDs. The argument that geeks seem to like things that don’t ever catch on with regular people has been defeated too many times to mention. There are plenty of examples of geekdom that never caught on with popular culture, but there are plenty of examples that did. The other thing is that mass appeal is no longer the only measure of success.

  8. “You’re going to get much farther if you don’t play to win.”

    I would disagree with this–probably always. But I would agree that bullshitting isn’t a viable path either. But people have very inset responses to different seduction techniques. Knowing that you have obstacles in your way due to youth, why not exploit them?

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