Why Pickup Artists Make Good Entrepreneurs – But not Vice Versa

A few of the people on my Heroes tab  (a list mostly composed of self made entrepreneurs) got to where they are through the Pickup Artist (PUA) community. People like Tynan and Mark Manson explicitly walked that path, but many of the others have skirted close, even if they were not ever ‘full time’ pickup artists (like Maneesh Sethi having lived with Papa from The Game and Michael Ellsberg, who almost wrote an ebook aggregating interviews with the best PUAs).

This is no coincidence – the lifehacking mindset that comes with pickup fits well with ‘anything to get it done’ mindset of an entrepreneur. However, I believe that a PUA perception of the world is intrinsically poisonous, while the latter can be applied healthily towards any pursuit. Here’s the similarities I see between the two, and why I condemn the PUA mindset.

Both embrace repeated failures

Pickup artists recognize that you have to fail at picking up a woman in order to understand what to do in order to succeed. It’s not uncommon for them to approach over a hundred women in one day and only get a few numbers, but hey, then you got some numbers and a whole lot of practice. There’s all sorts of self enforced rules they espouse to facilitate this, like requiring you to talk to a girl within five seconds of thinking about it, so as not to psyche yourself out. Or demanding at least twenty approaches per establishment, in order to overcome the nervousness and learn from each approach.

Similarly, entrepreneurs regard failures as valuable learning experiences that they can use to fuel their next endeavor. While they would probably like to succeed on their first business ventures, it is not uncommon for most successful founders to have several burning wrecks in the past before she got to where she is now. Accordingly, the community applauds ‘failing forward’, making Little Bets that don’t always work out, and acting in moments of doubt, just like the doubt inherent in approaching a stranger. Thomas Edison’s ‘You haven’t failed, you’ve just found 1000 ways that don’t work.” applies to both mindsets.

Both require false confidence bordering on arrogance

Walking up to a stranger and immediately presenting yourself as a possible partner puts your personality, appearance, and ‘manhood’ on the line, and is thus incredibly difficult to do without believing in your own worth. This is what draws many men to the PUAs – they promise to quell this self doubt and restore self confidence. There’s all sorts of ways to do this – I remember in The Game Mystery would have his disciples run around their living room giving each other high fives and shouting in order to build up adrenaline and testosterone for a night out of approaches. To become a PUA you must believe in yourself, which is a worthy goal, but sometimes leads to a false swagger that can be inimical to authentic relationships.

Likewise, for an entrepreneur to throw himself into a venture, he must believe in himself, his team, and his idea completely – there can be no room for doubt. Of course, his idea is not always valid, and nobody is perfect, so he must develop a sort of warped reality to get him through the naysayers as he throws his entire waking life at an idea. This confidence must be all-encompassing, or else his doubt will poison his decision making effectiveness. Likewise, this shield of arrogance that could ruin him if it hides the business weaknesses in his venture.

Both demand the dedication of a monk and the memorization of a nerd

PUAs memorize different opening lines, study other artists’ stories of their nights out, and familiarize themselves with all sorts of pickup workshops, books, and pedagogy. It’s no academic subject, but it is a discipline just like any other with rules to be learned and facts to be known. Many PUAs contend that you must devote yourself entirely to the ‘art’ or you will fail – so long hours hitting the books are required for entry.

Entrepreneurs must be knowledgable as well, but their ventures can fall into many different industries and thus their body of knowledge is more varied than studying the few thousand ways other men have endeavored to approach women. They have to know about industry current events happening, be familiar with the technical aspects of their product, and know how to sell themselves with their idea in pitches and branding. Hence all the books and school courses on how to be an entrepreneur (although the best way to learn is to start something yourself). You don’t have to be a scholar, but you have to know your stuff.

Both push you towards writing

As PUAs become known in the community they invariably start to teach what they have learned to the masses of losers they rose up out of  – for a price of course. Almost any name brand PUA has workshops, books, and tapes available for sale on their personal site, and some of them make a living entirely off of this material. I would guess that this happens because their study of pickup takes up so much of their life that they want to monetize it by teaching what they have learned to others. It all comes off as rather smarmy, however – look at any pickup site plastered with ads full of supermodels and promises to help you “sleep with any woman you see within hours”.

Meanwhile, any successful entrepreneur has books written about them (if not by them), and many who tried and failed have written about the experience in one way or another. From Paul Graham to Joseph Walla to Daniel Tenner, founder blogs, books, and journals are everywhere. The monetization rhetoric here is obvious – as an entrepreneur, of course they will try to turn their experience into a business.

But they are not the same

Since the two pursuits have so many habits and mindsets in common, it’s no wonder that many PUAs become entrepreneurs, although the reverse transformation is not as common. I believe this is because the pickup mindset is fundamentally misogynistic and limiting – unless it was what introduced you to lifehacking you aren’t going to embrace it from an existing position of success. While there are plenty of pickup techniques that normal men can use, once you start calling yourself a ‘pickup artist’ rather than just using a technique you read about online, you’ve crossed a line.

This is because at its core, pickup is about making people like you who wouldn’t otherwise. (Read: pretty women) It’s great that these men can find inner confidence and girlfriends from pickup, but think about it – they are changing their  personalities in order to appeal to random women at the bar. And they’re just doing it for the sex. Sure, they’ll end up with a steady girlfriend after enough attempts, but that’s not why they started pickup – just look at the way they talk in the forums and the ad copy used.

And they’ll never find a wife that way – because they’re using carnival tricks and deceptive techniques in order to garner these womens’ attention. You’ll never attract someone that way who likes you as much as someone attracted to the authentic you. Otherwise she is being attracted to a charade you are putting on, not the real you. Look at how many pickup artists have found their perfect life partner and settled down with her: None (that I’ve heard of). The smart ones have moved on to writing and other pursuits post pickup, while the rest continue peddling their workshops and techniques while rotating through a never ending parade of unfulfilling relationships and sexcapades. (Or try to build a  ‘mens’ rights’ site)

This is because the PUA mindset views women as nothing more than a challenge – rather than a human being. Their philosophy  deconstructs women into archetypes in order to succeed, losing their humanity in the process. Plus, they’re meeting these women mostly in bars and nightclubs, (often on weekddays, in order to have more practice time) which is a self selecting subset of the public; it’s not indicative of all women. Plus, they tend to view ‘no’ as a sign that they botched their approach, instead of a sign that she actually isn’t interested. Sometimes it’s true that a ‘no’ isn’t absolute, but obviously, internalizing that worldview is a dangerous path.

Entrepreneurship doesn’t come with any of these specific shortcomings, since it is focused on successful business endeavors rather that on getting with women. Leaning how to market a product, pitch yourself, and achieve product/market fit are all useful skills to bring to the rest of your life without an accompanying chauvinist undertone. Whereas if you go vice versa, you’ll have to unlearn some internalizations if you want to have fulfilling romantic relationships. Yet they are both very empowering philosophies.

Weekly Review #23

If you read one article this week, make it TechCrunch’s amazingly huge and comprehensive article on the San Francisco tech gentrification controversy. Author Kim Mai breaks down the issue’s parts, history, and underlying causes so methodically that you really can’t have a meaningful conversation with anyone about this issue without reading this article. She offers actionable plans toward solution for every party involved here, and concludes that while tech is a good scapegoat for the problem (and a contributor) it is not the only culprit. Read and learn.

Women consistently underestimate themselves despite equal or greater achievements than men. Good example of the inherent differences between the sexes that makes universal equal opportunities difficult. I remember Sheryl Sandberg’s Lean In book having good tips on how to address this.

Kevin Dewalt offers a step by step guide to turning your blog into a book with minimum hassle. Make writing a book easier, too, if all you have to do is focus on one post at a time. If you can write consistently, you can write a book. And you should write a book!

Waitbutwhy continues their surprisingly informative content that’s packaged as easily sharable with a guide to picking a life partner. Basically, you need a good friend you’re comfortable with and determined to make marriage work.

Eddy Azar’s public notes on Michael Ellsberg’s The Education of Millionaires includes several meaty takeaways:

  • Marketing & sales are the core of any big change in the world. It’s the only way to make a
    difference or make money. It’s how you make things people want, and it’s how people see that
    they want what you’ve made. Every great figure throughout history, was a great marketer.
  • If people know your name before you meet them, you’re set for success. Decide what you want
    people to think when they hear your name, and then make it so.
  • The entrepreneur knows that the only true rules and laws are those of physics (and even those are
    bendable). Social rules, societal rules, ‘laws’, do not need to be heeded. They can be broken, bypassed,
    bent, or ignored depending on what would most help him to create the reality he wants. The world is not fixed and full of rules you must comply to. In fact, all those rules are simply things most people agree with. But, if you don’t want to be like most people, don’t worry about what most people think. Do what makes sense to you, and what your role models do.

Bigassmessage.com and its sister bigasspicture.com are fun simple toys that may come in helpful on a Facebook wall near you.

Passwords are obsolete – the only real way to have users sign in securely is to have them authenticate via email, as Heartbleed is proving firsthand. This post offers a review of why that is and how developers can build a better login page.

Weekly Review #17

Don’t sell your time for a living – it sucks. To avoid it, 1)Learn how to make something, 2)Connect with audience, and 3)Keep doing it to become good. Startups are a good way to do this communally.

  • “It always shocks me when people don’t really know how to make anything. Or haven’t ever tried. It’s something we’ve all done as kids – drawings, crafts, etc. – but somehow a very large number of professional workers find themselves in a state where they only know how to repackage other peoples’ work rather than doing anything themselves.”

Ira Glass on Creativity. Refers to the paradox of making something because you like the end result, but your initial efforts aren’t good enough to satisfy your own taste. You gotta keep at it.

  • “What nobody tells people who are beginners — and I really wish someone had told this to me . . . is that all of us who do creative work, we get into it because we have good taste. But there is this gap. For the first couple years you make stuff, and it’s just not that good. It’s trying to be good, it has potential, but it’s not.

    But your taste, the thing that got you into the game, is still killer. And your taste is why your work disappoints you. A lot of people never get past this phase. They quit. Most people I know who do interesting, creative work went through years of this. We know our work doesn’t have this special thing that we want it to have. We all go through this. And if you are just starting out or you are still in this phase, you gotta know it’s normal and the most important thing you can do is do a lot of work. Put yourself on a deadline so that every week you will finish one story.

    It is only by going through a volume of work that you will close that gap, and your work will be as good as your ambitions. And I took longer to figure out how to do this than anyone I’ve ever met. It’s gonna take awhile. It’s normal to take awhile. You’ve just gotta fight your way through.”

Lessons learned going through Y Combinator. Be comfortable doing anything. Avoid all distractions when starting a company. Don’t forget human contact. Listen to your customers and iterate. Set deadlines and measure progress. Nobody knows what they’re doing. Take advice, not too seriously. Enjoy yourself.

Midstage startups are the best first tech jobs for new grads. duh. Because your work will have direct impact, there’s no layers between you and the managers, the team will stick with you, your options will be gold, and people look highly at you.

Paul Graham notes that every city has a personality that will make you ambitious towards something. In NY, it’s money, in Silicon Valley, it’s power, in Paris, it’s style. This matters because where you live is either a force multiplier or dampener depending on what you’re doing.

  • Walk through your town at dusk and look through windows. What do you see? “The conversations you overhear tell you what sort of people you’re among”
  • “it helps most to be in a place where you can find peers and encouragement. You seem to be able to leave, if you want, once you’ve found both. The Impressionists show the typical pattern: they were born all over France (Pissarro was born in the Carribbean) and died all over France, but what defined them were the years they spent together in Paris.”