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If you do date two women at the same time, give each a present: a small bottle of the SAME perfume.

(Just passing on some advice from a smart guy I worked with)

I'm going to kill this whole post. It got taken over by the metaphor used in it.

Just shows how powerful the attraction of lightweight stuff is. One of the big problems on a user voted news site is to keep out the kind of frivolous crap that would otherwise float to the top because it's easy to upvote and everyone has an opinion about it. An actual post about dating would be offtopic for precisely this reason. But as the comments on this thread show, people's interest in fluff is so great that even if you're merely using a fluff point to explain something more solid, the fluff aspect of it will tend to take over.

Paul, thanks, please do. This has gotten out of hand.

Or better yet: don't give gifts at all, until you're in a long-term relationship.

(Yes, seriously.)

Well then one will smell the others perfume. You have to initialize both the variables to be the same.

:-)

(I get the Whoosh award for today.)

The intent of gifting the same perfume is so that you won't get caught when your gfs use their olfactory lobes.

What are the chances that they will wear the same perfume if they purchased independently?

of course, most adult women probably have more than one bottle of perfume, and they probably wouldn't wear it every single time they would be with the person in question, unless they really liked the scent. I think I have around five I use frequently and even more stashed, sometimes I'll just stick with one and other times I'll layer a couple of perfumes. Depends on the mood I'm in that day, as well as the weather and occasion.

the better advice, if you can get away with it: be truthful. some people are open to open relationships and maybe even polyamory. having been in a position where I was the "other girl" (love makes one do funny things), the whole being secretive and sneaking around thing, as well as the ensuing fights, was painful..and the other woman doesn't even know the whole story still.

- sniff sniff Is that Elizabeth Dior No. 5 on your shirt?

- Yes, I love it when you wear that perfume I gave you.

- I know. So I ran out of it a month ago.

- Uhhh, I havn't had time to do my laundry lately.

It is not clear to me whether you should date lots of girls, or just know lots of girls who you could date if your current relationship falls apart.

I think I agree when it comes to clients and investors, but in terms of major technical (or business-plan type) components, once you have multiple avenues you'll need more resources, more planning, and it seems like you'll inevitably lose focus.

Date lots of women but only marry one?

Yeah, this advice definitely applies more to the business side than the tech side. Business is people, and people are unpredictable and driven by emotion.

On the tech side, you want to stay lean and mean.

It is not clear to me whether you should date lots of girls, or just know lots of girls who you could date if your current relationship falls apart.

I'm pretty sure his use of the word "date" means "going on dates with", not "be in a relationship with". Having 2+ girlfriends is a bad idea, especially if you're starting a company.

I didn't come up with this, but it works:

--

An architect, an artist and an engineer were discussing whether it was better to spend time with the wife or a mistress.

The architect said he enjoyed time with his wife, building a solid foundation for an enduring relationship.

The artist said he enjoyed time with his mistress, because of the passion and mystery he found there.

The engineer said, "I like both."

"Both?"

Engineer: "Yeah. If you have a wife and a mistress, they will each assume you are spending time with the other woman, and you can go to the lab and get some work done!

Personally I believe in focus...you succeed by doing that one thing really really well. If you spread yourself in 10 different directions, you'll have ten different mediocre paths to mediocrity. Why? Because while you split your time between 10 different options, 10 different people will be spending 100% of their time, on each option.

Better to focus 110% on one thing...fail quickly(if its destined for failure), and go do something else.

as far as actual dating is concerned...who has the time really? If you were in a relationship before you started working on your startup, sure you might still keep it up(provided the woman is extremely understanding). But if you are just starting the whole process and are also focused on your startup...when do you even have the time to date?

I've always done what you outline. It works great for me, and I like having many fingers in many pies, but I'm pretty convinced it only works because of my personality.

Would Google, Microsoft or Apple be where they are now if the founders had decided to work on several things at once? All reasonably single minded people involved there who threw their all into their respective companies.

I'm never going to found a 8 or 9 figure revenue company because I don't want to be that focused or that single minded. Fine for me, but the people who do want that option are probably best off not dating more than one girl, right?

I've always done this too, to good effect, but I think there's an important distinction that the writer didn't point out. When you're playing the field and gathering options, date many girls. But once you've found a good one, settle down and focus on it, er...her. ;-)

When I'm hunting for a job, I try to always have at least 2, preferably 3 possibilities (when I've tried 4, though, I dropped all the balls and didn't get hired by any of them). But once I'm hired - or once I've got a promising startup idea - I drop the others and concentrate on the job to do. Otherwise, I can't get any work done. Multitasking is incredibly inefficient.

When I broke this rule (first 9 months of my startup's existence), it turned out badly. I somehow managed to avoid getting fired and seem to have gotten a decent recommendation, but I had to throw away all the startup code I'd written part-time (it sucked) and my job was a lot more stressful and less successful than it otherwise would've been.

To extend the dating analogy - a couple of my friends have tried the whole poly thing, having serious relationships in triples. It always ends in tears and/or broken friendships. It's just not possible to devote that much attention to multiple startups...er, girls.

> I like having many fingers in many pies,

I wouldn't point this out on here, but given the context of the article it's too hard to resist.

Is there any reason to believe that the founders of Microsoft, Google, etc did not have other side projects ? And that if one of those projects had succeeded, they would never mention the others, because pretty much everything writen by or about them is various forms of corporate propaganda ?

If anyone would know the answer to that, it would probably be Stephen Levy, I respect his books on the history of the tech industry a lot.

They did have other side-projects - Bill Gates and Paul Allen did the course scheduling for their high school, and they had a consulting contract for software to control traffic lights, and they each took part-time jobs at Altair before Microsoft took off. However, except for the Altair/Microsoft split (where they were working on very closely-related projects), they worked on them sequentially, finishing one before they did the next.

My guess would be that either:

1) They had side projects outside of the company that we never hear about because they ended up being orders of magnitude less than their respective companies

or

2) They had "side projects", but everything they did was under the umbrella of the company. Things like the Google Appliance; Microsoft's many lines of products besides the big ones(it was years before DOS/Windows came out) etc.

Of course the founders of Microsoft and Google had other projects: the college degree programs they dropped out of.

Corollary: apply basic sales pipeline management techniques to everything (fundraising, customer acquisition, pr, market discovery, etc). The only place this gets dicey is in product development. Products are like girls you're starting to get serious with. For any significant product with a small team, you can only really devote detailed attention to one. On the bright side, your customers will help you decide which girl you should be spending the most time with.

Damn, wish I could go back and edit this post to make it more clear.

I am talking about BUSINESS here: meetings with VC, clients, etc. Not actual dating. I repeat, not actual dating.

When it comes to dating, stick to ONE GIRL AT A TIME.

But when it comes to getting your STARTUP IDEA off the ground, have multiple paths to success. Don't put all your eggs in one basket, otherwise you will be desperate for that basket to work out, and 9 times out of 10, it won't.

Apparently, the consensus is that your original advice is more correct. I think it's accurate enough because both take some effort to pull off.

From what I can see of startups, the really appropriate analogy is to pursue the same strategies as a stereotypical gold-digging "hot" chick. Keep up a glamorous appearance above all else, even if you're poor and living in a tiny space. Go to lots of parties and try to get people to talk about you. Have alliances with girls in the same situation, and "friend mode" advisors who enjoy the vicarious thrill of being near you. In one-on-one encounters, you have to have a great demo, even if it doesn't "scale" (there's no chance you would be able or willing to do that all night or every night). Use a succession of sugar daddies to pay the bills until some old rich chump who wants to look and feel young again proposes.

There are some common flaws that also need to be fixed if you take this route of action:

1) Get rid of your Facebook account. Or, setup the privacy so that your wall doesn't exist and the two girlfriends are unable to comment on the same photos of you.

2) Have a primary cell phone and a secondary phone. Give your primary girlfriend your primary cell, give the secondary/tertiary/etc'iary girlfriends the secondary number

3) I used to know a lot more, because in high school I really wanted to date 3 or 4 girls at a time (and I could, but friends talked me out of it). I had a full list of things, but I have forgotten the smaller items.

I call bullshit.

I don't know how old you are. I'm about to turn 29 years old shortly. And I dated multiple women for the last 10 years. The most I got to was dating 4 different women at the same time.

It didn't work for me. And it took me 10 years to actually figure out why this was.

Dating multiple women requires a certain level of emotional detachment that makes it difficult to actually make a relationship work.

And if you're trying to imply this is how startups work too, I'll quote Bjarne Stroustrup for you: "Proof by analogy is fraud."

This advice works well in the very early stages of a startup, but focus is needed once you have done your "market research." To continue the analogy, you should not date more than one girl once you are going steady.

If you want to read more about this shifting from a broad to a narrow focus, I highly recommend Crossing the Chasm by Geoffrey Moore.

http://www.amazon.com/Crossing-Chasm-Marketing-High-Tech-Mai...

I understand the wisdom of this advice, but I can never bring myself to do it. Feels like betrayal. I guess I'm just too traditional for my own good.

Just be honest.

The good: dating multiple girls eliminates frustration, they can nag/cheat/leave all they want, you don't have to care. The bad: danger is multiplied by N. Psycho ex-boyfriends, STDs, pregnancies, suicide attempts, calls to your relatives... Dating many girls is a great way of life where the highs more than compensate for the lows - but please be careful.

However, as would be the case with dating more than one girl, don't spread yourself too thin. If you start dating 10 people, and try to keep up a working relationship with all of them, you might find it hard to ever get any relationship to last very long. Feel free to pick up more than one, but make sure you give ample attention to each.

Talking about YC doesn't so much bother me, but dating advice albeit business related makes me wonder if this thread has 'jumped the shark'.

Still, I laughed. Dating more than 1 girl is especially applicable in SV although not empirically advised.

Is there more than one girl in SV? ;)

Good point and the 1 girl there is... she's taken.

I agree with this. Dating multiple girls improves your judgment, so when you want to settle down you'll often make the right choice. You won't get "oneitist" and fall for the wrong type of girl.

It's also a big confidence boost too.

Same advice applies to girls...

Not unless they're dating nerdy startup guys.

The analogy you're making reminds me of the quote, "VCs are like women: they only want you if others do."

You're absolutely correct that, before a deal is sealed (signed term sheet, or relationship) in either arena, it makes sense not only to keep open as many options as possible, but also to seek out more open options. Your "game" will failbox if you only have one prospect, because this person has an incredible amount of power over you. Of course, eventually, you have to take the plunge and commit to one.

However, the analogy between women and funding is pretty weak. The most obvious difference is that sources of funding are pretty much interchangeable, and it's utterly necessary to get some sort of funding, so it makes sense to jump on the first reasonable offer. Women, on the other hand, are decidedly not interchangeable, while there's no need to be in a relationship, so it makes sense to be picky and hold out for an exceptionally good match.

"sources of funding are pretty much interchangeable"

I'd agree to a point... thefunded.com exists for a reason. :)

True, and just as bad women can fuck up your life, bad investors can ruin your company. I guess the difference relevant to my point is that between the average and the exceptional. It makes sense to take funding from a source of average reputation and prestige, if the terms are good, rather than holding out for Sequoia. In dating, the "average" match isn't very good, and it makes a lot of sense to hold out for the mind-blowing awesome woman.

If you just wait for the mind-blowing-awesome-woman, you will never have any.

That's fine, because a mediocre or bad relationship is costly in comparison to what little it provides. Being single doesn't ensure loneliness, and being married doesn't imply the lack thereof.

There are plenty of hedonic studies that show that married people are neither happier nor less happy, as a group, than singles, and that people with children are actually less happy when the children are young (which makes sense; young kids are annoying). This is often taken to indicate that romantic relationships have no bearing on personal happiness. That's wrong, actually. The average is flat, but individual people shift around (up, or down) a great deal.

"Expectancy" in getting married, however, is about zero. If you settle out of some desire to be married for its own sake, it's probably negative.

it does? really? are there any? (mind-blowing awesome women)

Yes. I met one recently. She's beautiful, not demanding, and gives me falafels whenever I want.

Falafel store girl is mind blowingly awesome in every way.

Maybe one day I'll even have a conversation with her. But that's unlikely, I'm too shy.

Give it a shot. You've nothing to lose.

If you're afraid of risking rejection and failure, then what are you doing on a startup board?

Mind blowingly awesome falafels are even rarer than mind blowingly awesome women. Mind blowingly awesome falafels within 5 blocks of my office?

I can live with other women, but not with other falafels.

If she rejects you romantically, you can still go in and buy falafels. Unless you're 4 sigma of fail and get hit with a restraining order, that is.

That puts my odds of losing the falafels at 25%.

But maybe if I can get her fired, then I can ask her out...

Yes, but they're rare and you usually have to steal them. (By which I mean lure them out of mediocre relationships; nothing Borat-style.)

Foreign countries are also a good idea. You won't believe it until you see it.

"Steal" someone, and all you get is someone who is easily stolen.

Find a single girl, and all you get is someone nobody else wants.

The above is flamingly, almost disgustingly, false, and I said it only to illustrate a sweeping stereotype. What you say is generally correct, but I wouldn't apply it in all cases. Anyway, by "steal", I don't mean that you should actively damage the relationship. That's evil and also quite pathetic. I mean that you become friends with the girl and wait for the relationship to find its end, which it will if the girl likes you better than her current boyfriend-- and while there are very, very few compelling women who are available and unattached, there are a hell of a lot of them dating loser men.

I generally agree with you in principle. And it's not a good thing that the vast majority of attractive women are unavailable. It's much better if you can find a shy, quirky girl who happens, against all odds, to be single and available, but while this is the gold standard, it's incredibly uncommon.

Date more than one girl.