I was chatting with my friend Ramit Sethi (or as I like to call him in front of the ladies, "New York Times Bestselling Author and Millionaire Ramit Sethi") when I realized something:
A lot of men in Silicon Valley (and on Hacker News and Reddit) understand how to pitch VCs and angel investors. It seems like a much smaller proportion feel comfortable courting women.
The funny thing is that many of the same principles apply! So here is one old married guy's gift to the dating world:
How to Date like an Entrepreneur
(Note that this advice is going to be male/heterosexual-centric; sorry, I've got to write what I know!)
1) Know your elevator pitch.
If someone says, "Tell me about yourself," you darn well better be able to launch into a clear, concise talk, not a rambling life story. Hit the key points (where you grew up, where you went to school, your career, your interests and activities) and then assess the reaction.
2) Know your audience.
Sadly, the ad hoc nature of dating means that you won't always be able to research people ahead of time. When you can, learn as much as you can--in today's social world, you can find out a lot. When you can't, make sure you focus on asking questions so you can learn about your date early on in the evening.
Alternately, if you're my friend Ben Casnocha, you can just check out her delicious feed and her Amazon wishlist!
3) Read body language.
Many entrepreneurs misread VCs because they focus on words rather than body language. Investors don't want to reject you too harshly--maybe they'll want in on the deal if someone else leads. Similarly, politeness dictates that women not tell you, "Not if you were the last non-zombie on the face of the Earth."
Body language is much more truthful. Does it seem like she actively leans in and wants to spend more time with you? Or are her eyes darting around the room looking for an escape route. As with VCs, someone who reads their email the whole time is indicating a lack of interest.
4) Know your objective.
In your first investor meeting, your objective is to spark enough interest to get a second meeting. Same for dating. Don't try to win her heart in the first 15 minutes. Just get her interested enough to see you again. And when the customer is sold, shut up and ask for the order.
5) Your attractiveness depends on competition.
Like VCs, women want to date a man other women find attractive. Ideally, other women come up to you and talk with you. This is where developing a wide set of relationships helps--even if a woman isn't interested in you romantically, if she pays attention to you, you will seem more attractive to other women.
Similarly, your attractiveness will depend on the available substitutes. Being one of the only men at a party is good. Attending your friend's male modeling agency holiday party is bad.
6) You only need one to say yes.
Ultimately, dating is like fundraising. It's a means to an end. All that matters is that you find the right person for a real relationship. Don't get caught up in the game; the real value comes from what you build, whether it's a business or a relationship.