The Single Most Important Choice You Will Ever Make

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[ex cfo during the dot com period late nineties...]
The single most important choice you will ever have to really make is the person you marry. She can make you or break you. Don't pay attention to the pop psychology bull. No other investment can be anywhere as significant. And you don't just "get lucky"...A good choice takes hard work, patience, intelligence and serious due diligence, and it will take balls. If you're gun shy, slow, or a sheep you could lose very, very badly. There are no good girls, or bad girls. Love is the toughest market you will ever have to work in. All the hard work you have put into your lives so far, pale in comparison to the work you have to put into the choice of your mate.

It's not that different from the silicon valley venture investor and a new start-up. Think in terms of aligned interests. When you're desperate for money, any investor will do, but you really should be careful with who you hop into bed with because the wrong choice can make life a living hell. Even in the best of cases, the VC -start up relationship is wrought with turmoil, betrayal, conflicting information, sleepless nights, and nerve-wracked days. The day to day grind can just pulverize you and you will get no sympathy from your VC investors. You don't hit your targets, and you may be looking at a serious down round when you need cash again. Even if you hit pay dirt, it is often nasty.That's when you choose well. Let's not get into what happens you're going through an IPO...

This is how I would approach the subject if you're still fairly virgin and living in this business.You are working obscene hours. You're tired and spent. Every day you have to be on your toes, and display self control in the face of complete chaos. You make decent money even at the start, though it may not feel like it on the inside.Trust me, on the outside, you're making a fortune. You're potential is climbing and envious. You're even considered exotic and desirable. You're horny as hell. You're also a bit of dreamer and romantic. And you have some semblance of morality left in terms of what you may define as "family". Be honest with yourselves, you're a target... even for "good girls".

If you're down this path of even considering marriage or a serious relationship, think about these things as cold bloodily as you can:

1. Is she an asset? Does she become a force-multiplier in your life? or is she a liability?Is she helping you with the day-to day shit in your life.? Does she smile at you often? (most married women always seem so pissed off) Is she flexible with you? or... Is she more superficial than she should be? Remember that all the things you find "cute" in her will eventually drive you to drink.

2. Does she really understand what you're living through? I mean, does she experience what you have to put up with? Even if she comes from the business, or not, does she have a dry martini and caviar on toast waiting for you when you come home? Does she just let you sit there and vege out in you stupor as you recover from the bombardments of the day and the humiliating commute, or does she rag about stuff that has nothing to do with your work.

3. The most successful men do not have the most beautiful wives. They were smart enough to know that really beautiful women are usually lousy in the sack and way too high maintenance. They have average to attractive looking women who are smart, sympathetic, patient and supportive of their man. You won't need Viagra with them.

And like any investment with a high return profile, you have to be prepared to lose it all...stoop down and rebuild with worn out tools, never speak a word about your loss...

and children change all the rules....

Just my two cents...