Jun’s Startup Life

I was lucky enough to engage in a phone conference with Penelope Trunk where she spoke about her 5 Rules of Blogging.  The rules were sound pieces of advice, and they perfectly match my 5 Rules of First Dates.  Here are the exact comparisons:

Rule #1: Keep it short

Blog posts should be kept to a maximum of 600-700 words.

First dates should start and end with one event.  A lot of men make the mistake of trying to drag on the first date forever. I don’t care if you’re having the time of your life, end the date on a high note so that you leave her wanting more.

Another common mistake is that you make your move too soon.  Unless all you want to do is sleep with her, making a move on the first date just shows that you’re looking for some ass rather than a real relationship.  If this girl means something to you, then you should wait.

Rule #2: Do something fresh

Don’t write the same old boring stuff.  What do you do if you can’t think of a fresh topic?  Check out what’s being talked about on the blogosphere and see if you disagree with anyone’s opinion.  The topic doesn’t necessarily have to be fresh; your different take on a saturated topic can be new to your readers.

Girls love it when you do something fun, exciting, and out of the ordinary.  Just because you’re taking her to dinner doesn’t mean that you can’t do something out of the ordinary.  You see, “out of the ordinary” is all relative.  Something ordinary for you can be extraordinary for her.  Take her to a restaurant she’s never been to, or better yet, take her on an adventure.  That’s what I did with my girlfriend.  I took her to a Brazilian restaurant and took her out skating across the UCLA campus.  It was perfect!  She had never before gone skating, and I took her on a little adventure.  Skating might be ordinary to many of you, but skating was extraordinary for Kim.

Rule #3: Personalize it!

Don’t just repeat a news story; write about YOUR opinions and how it affects you.  Better yet, what is the main theme of your blog?  You can tie everything you write about to the main theme of your blog.

A very common mistake guys make is that they let the girl do all of the talking.  A guy gets into this mode of asking 20 questions because for some reason we think that “girls love to talk.”  Yes, they do love to talk, but more than anything else, they love to be enlightened, entertained, or shown something new.  Talk about what’s important to you, tell personal stories, be charismatic, and most importantly, take control of the date.  Remember, this is your date (this is your blog), you control the tempo of the date and you control the conversations.  Show her that you are man enough to control her.

Rule #4: Establish a Community

Think about who you’re tailoring your blog post for.  If you’re targeting undergraduates, then speak directly to them.  If you’re targeting professionals who are tired of their work and are looking for some advice to make their lives better, then speak directly to them.  Know your target and write for them.

This part comes after the first date.  In order to build a strong relationship with her, you have to build a community around her friends.  You don’t necessarily have to like them, but you have to make them like you and be able to hold a conversation with them.  How do you get them to like you?  It’s actually much easier than people make it out to be.  Be genuine, friendly, and make an attempt to start the conversation.  Just like on your first date, you have to take control of the conversation and start telling your stories.  Everybody can listen, but YOU can engage your audience (her friends) with your stories.

Rule #5: Get an Editor/Wingman

An editor is crucial for having a high quality blog.  We may think that we’ve written a golden post, but our editor tells us the truth about what’s wrong with our posts and how we can make it better.

A Wingman is more than just someone who goes with you to a club to “pick up a girl.”  A Wingman is someone that you are confident in introducing your girlfriend to.  Remember, she is constantly looking if you have high value.  My Dad has always said, “Show me who you hang out with, and I’ll tell you who you are.” This has been one of the most powerful pieces of advice in my life.  Show her that you have “cool” friends, and she’ll think even more highly of you.  [When I write "cool," I mean someone who is fun to hang out with.  Maybe your wingman has a girlfriend who you guys can double date with, that is an ideal situation.]