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A 'When Harry Met Sally' Relationship

Kim shares her thoughts on Dwight (and what to do on a date).

By Kim Taylor Nov 20, 2012, 3:09 PM ET

This was my favorite episode yet! There is drama both personally and professionally. We deal with underwater mortgages, sexism, biological clocks, and some gay line dancing for good measure! We also introduce America to a new phenomenon known as "date cheating."

I start my morning at my apartment and I’m contemplating my conversation with my CEO. I’ve devoted two years of my life to someone else’s company and made them a lot of money, why would I not devote two years of my life to my own company?

Lunch with Ethan

So I sit down for lunch with my friend Ethan. He was the founder of a company called Redbeacon that recently sold to Home Depot this year and someone whose opinion I value.

Advantages? I tell him I’m not married, no children, no mortgage, and no debt. Which in my world is an advantage. I’m definitely at a point in my life where I am able to take a risk, with far less at stake than those who have additional responsibilities. Ethan jokes that I didn’t let life get in the way of my career. I don’t think it’s a choice, and you have to have one or the other. Sheryl Sandberg, the COO of Facebook (and Mark Zuckerberg’s number two) probably addresses this issue best championing that women in the workplace shouldn’t "leave before they leave" in her famous Ted talk.

The world is changing, as are gender roles. Women are increasingly going to be the breadwinners in their families. Men are contributing more at home. A lot of start-ups are beginning to address this. Why can a man get their shoes shined at work but women can’t get manicures? A new startup in New York, Manicube, is a great example of how the workplace is evolving to accommodate working women. This is just the tip of the iceberg. More great things are always happening in the tech world.

Certain people may have full on meltdowns over their biological clocks. I decided that I would never force life decisions based on my age or a forced sense of urgency by what others were doing around me. So I’m happily 30 and single. Ethan tells me I need a technical co-founder. I do not look pleased and clearly will not be entering the World Series of Poker anytime soon. According to prominent venture capitalist Dave McClure great start-ups should start with a hacker, a hustler, and a designer.

We never discuss what it is I want to build. San Francisco and Silicon Valley are engineering driven cultures where we glorify engineers and everyone must have a technical co-founder. The business I plan to build is based more upon curation and editorial, so I pass on this advice. NastyGal is a great example of start-up without a technical co-founder. They built a massive business that started simply as an eBay store in 2006 but they understood their demographic better than far more sophisticated start-ups around them. They still do.

"I understand how to make money."

This is a bit of an obnoxious comment. I do that. However something start-ups are often criticized for is creating apps and companies without a prayer of having a revenue model. My background was being the person responsible for revenue and making sure we are profitable, so I’m not planning on having that problem. Call me old school, but I was always taught that businesses are supposed to make money.

At the end of lunch I mention that it’s important to get a lot of advice. It’s also important to know when to throw some of that advice “out the f-cking window.” No one knows your vision and your business as well as you do. Trust your gut.

"Dwight went to Berkeley. His friends lived in trees. I'm easing him into society."

You’ll see me head to dinner with my close friend and entrepreneur, Dwight Crow, in Palo Alto. There are certain people you can always unapologetically be yourself around. He is that person for me. We are always a two person party.Being as close as we are, I feel it is my duty to give him sh-t on what he should have done differently if we were on a date (should I be so lucky):

- Order the wine. He passed the menu to me to order. Take charge!
- Ask your date if she's ready to order.
- Let her order first.
- Don't order your entree at the same time as your drinks. This will also help to pace the kitchen so they don't bring out your entree at the same time as your appetizer.

Yes, I offered to pay. I picked the restaurant and it was probably out of his price range at the time and was planning to anyway. Yes, he called me bootylicious. High praise that I thought was only meant for Beyonce. He may also have a little crush on me.

At this moment in time I was making a decision about what direction I wanted my life and career to go in. Did I want stability, a steady paycheck, a new car or a world of unknown with no income and high risk?

Dwight and I have what some might call a “When Harry Met Sally” relationship. Dwight grew up without a television and when someone recently asked how he felt about our “When Harry Met Sally” relationship, he responded he has never met Harry or Sally and dreams in SQL (a programming language). What's not to love?

Thanks so much for tuning every Monday at 10/9c on Bravo to watch Start-Ups: Silicon Valley! Follow me on Twitter (@kimmytaylor) and subscribe on Facebook (www.facebook.com/kimtaylor10).

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