How Practicing Pickup Helped Us Win Startup Weekend

I just got back from Startup Weekend (here in Wrocław!) and my team won the Audience Award for Best Startup. Our startup was a mobile app based off this Free Idea called TripHunt.

This was the inaugural Startup Weekend in Wrocław – and my first Startup Weekend as well – so I had no idea what to expect. More than that, I was scared to attend. What I’ve learned from pickup helped a lot.

What people (read: women) don’t understand about pickup is that it’s about much more than getting in anybody’s pants. It’s about improving social skills that carry over to all aspects of life.

I get it though. You see the phrase “pickup women” and you get a tight, maybe nauseous, feeling in your stomach. I used to as well because it is true there are quite a lot of guys who do it in a manipulative way.

The counter-argument is that we’re all manipulative in relationships. If you don’t believe so then you’re not being honest with yourself. If you ever don’t call a guy/girl back or ignore them or try to make them jealous you’re being manipulative. The examples of manipulation you and I engage in could fill a book and if you think back over the last several days you can come up with at least one example of how you manipulated someone.

In my last month in the U.S. I got dozens of phone numbers and experienced over 100 one-time interactions with women (running the gamut from just a short conversation to spending hours together). The biggest thing I learned from all this is both depressing and enlightening. Many women are flakes. I can’t currently think of a more spinelessly weak quality in a human being than flakiness.

Interestingly enough, in media (particularly movies and TV), men are usually portrayed as flakes. “He said he’d call. Why won’t he call?!” And maybe this is true. From my particular point of view I don’t see it. I know lots of great dudes that any woman would be lucky to have. Dudes who mostly get ignored or passed over for more “exciting,” but ultimately, wrong guys. The veritable Mr. Wrong.

I would put the flakes vs non-flakes ratio at about 10 to 1, but there are a lot of variables here. Was the initial interaction very short? Was the chemistry palpable? Sometimes a very short interaction clicks. And sometimes a very long interaction doesn’t (even if you think it does). There are far too many questions and situations to put a valid number on it beyond my own experience.

OK, so that’s depressing, but there is an upside. There is always an upside. Not all women are flakes. Not by any means. And I’ve met a couple nice girls here.

But what this all means, as a single guy, is you need to meet an incredibly large amount of women to meet the good ones. (Flakes = not good ones.) Then you need to meet a lot of good ones to find the few you will actually get along with over a period of time. If you’re not naturally extroverted, and not naturally socially skilled, this is tough to take in. You either settle for whoever comes along (the norm for many girls and guys) or you wallow in singledom.

Three 6 Mafia’s Oscar-winning song “It’s Hard Out Here For A Pimp” may have been onto something, but the proper noun is incorrect. It’s hard out here for a nice guy. It’s not that nice guys finish last. It’s that nice guys don’t even enter the race.

Happily, there is a solution: learn social skills such as pickup.

Pickup doesn’t have a very good reputation and some of it may be due to preconceived notions.

More than that, the issue is that if you have a problem with pickup you likely lack empathy.

Empathy, as you know, is the ability to recognize the feelings of what other living creatures are feeling. The phrase, “Try walking a mile in their shoes” is based on empathy. When I get an e-mail asking me, “Do you hate women or something?” it’s because the sender lacks empathy.

I’ve also received a lot of e-mails asking, “when are you going to update us on pickup?” I won’t write about it often because, truth be told, there’s not much to say that hasn’t been said before. I talk to a lot of women. I get rejected a lot. Sometimes I don’t. Sometimes it’s incredibly disheartening and depressing. Sometimes it’s not (such as the examples I haven’t shared). My best option is to write about this topic in more of a “life lesson” style such as what I’m doing right now as opposed to writing about specific interactions.

Which brings me back to Startup Weekend and how pickup helped me help my team win the Audience Award for Best Startup.

1) Improved Solo Social Skills

When I first heard about Startup Weekend Wrocław I was very excited, but then I got scared and didn’t register immediately. “I don’t know anybody who will be there. I’m not good at making new friends. This might be an incredibly lonely weekend.” Because lonely to me is not being by myself. Lonely to me is being in a large group and not connecting with a single person while everybody around me is having the time of their lives. I often enjoy solo social activities (such as movies), but activities where you need to interact with people can be quite lonely without social skills.

Then I remembered that nearly every new social situation is like going up to a random girl on the street and trying to get her number. First off, it’s fun, energizing, and the action is not very difficult (walk and say words). And second, I know I won’t connect with everybody anyway so the goal is to meet the few people I connect with.

I obviously wouldn’t have been on the winning team if I didn’t attend. I have the social skills I’ve developed through pickup to thank for pushing me to register.

2) Improved Public Speaking Skills

Prior to this past weekend I hadn’t done any public speaking since September of 2010, nearly 2 years ago. That was in front of maybe 40 people (including a handful of friends) and I stumbled, fumbled, and looked like a fool.

But I actually wasn’t nervous about speaking in front of the ~200 people at Startup Weekend.

Pickup gave me the skills to speak confidently in front of strangers and the reason is simple. One of the biggest sticking points with guys learning pickup is, “But what about the people around her? What will they think?” When practicing pickup you’re essentially doing public speaking, albeit on a smaller stage.

The truth is people won’t think about what you’re doing. If anything, guys will be envious that you are able to easily approach girls, and girls will be envious of the girl you’re talking to. But mostly nobody cares and they won’t be paying attention to you. People are too caught up in their own worlds and that leaves you free to live in your own world.

In a situation like Startup Weekend lots of people are focusing just on you when you’re speaking, but practicing pickup has desensitized me to rejection. It still stings to get rejected, but I’m able deal with it better. Which brings me to …

3) Constructive Use of Adrenaline

The way Startup Weekend works is, if you have an idea, you pitch it on Day 1, people vote, and, if you get enough votes, you’ll form a team to build your project. That first pitch is 60 seconds and not all ideas move on. But if your idea moves on you will have to present your completed (or incomplete) project to judges and the rest of the audience at the end of Day 3. This is a longer pitch. Ours were limited to 4 minutes (+ 3 minutes for Q&A).

When it was time to gather in the auditorium at UNESCO World Heritage Site Hala Stulecia I was very tired due to lack of sleep, lack of food (no vegan food on premises and no time to go out for food meant I was starving most of the weekend), and general mental exhaustion. I was sitting there in the auditorium with heavy eyelids and I was afraid the sleepiness would show in my presentation. Well, there is nothing I can think of that naturally wakes me up like practicing pickup.

My mission was to quickly find the prettiest girl at the event (I had briefly spoken to her on Day 1) and try to get her number. She was talking to a guy when I found her. Whatever. I approached and in less than 30 seconds got rejected (very pleasantly, apologetically even), but I had the shot of adrenaline I needed.

Pickup helped me “win” Startup Weekend before voting even began.

Winning an actual award was icing on the cake. And, let’s be honest, winning an actual award at something like this isn’t all about social skills. If it wasn’t for my talented team I would have had nothing to present. They worked their asses off to refine, design, and demo our idea. We got so much great feedback that centered around, “the fact that you had a video demo of your app blew me away!” We had a feeling that would be the case, hence hustling to get a video demo together.

This is already at 1,600 words so maybe I’ll write specifically about Startup Weekend another time.

Until then thanks to my team, the Startup Weekend organizers, and all the girls who pretend to like me. ;)

10 Responses to How Practicing Pickup Helped Us Win Startup Weekend

  1. Karol,

    Congrats on the award win, but more congrats on the successful implementation of your cool idea!

    Thanks for everything you write.

  2. Every time I read about you essentially feeling the fear but doing it anyway, it renews my resolve to do the same. As a teen and young adult I had a lot of self confidence and had a lot of social interactions. I don’t know what changed as I aged, but I am not the person I used to be. Thanks for the reminder, to just get out there and talk to people!

    • I think maybe this is normal. As we get older and establish routines we lose some of our positive youthful tendencies. You’re welcome for the reminder.

  3. I tried picking up a girl at a Startup. Yyyt fr t cfterdffsddegWeekend and got. U rf. ejected, too! Unfortun * h. asdsttffx yt rrt. Stely, it wa s df at the end of the. Fweeke,3$nd, so that ad ygygi. C y ren. Yra3aline was. n’t optimally used, but I wa s still proud of mdybhyself.

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