“Raising venture capital is just like dating” 

Inspiration comes from the strangest things. Last week I was having a conversation with Joanna Van Vleck, founder of a rockin’ new company called The Trunk Club. It’s the States’ hottest new Web 2.0 business: an online  clothes shop for men with expert style advice thrown in. It’s catching on like wildfire. With this rapid growth and notoriety comes a need for risk capital of the best kind – venture capital. And you wouldn’t believe how similar the venture capital process is to another risky enterprise: dating.

I am probably one of the 37 straight men in the world that actually enjoys shopping. For most men it’s nothing but a huge hassle. However I will say this: as my schedule ever increases and every minute of my day is becoming more and more precious, I contemplate becoming a Trunk Club member myself.

Anyways, I’m about five minutes into a call with Joanna, talking about her business and raising finance and she goes, “I can’t tell you how many similarities I see between the VC process and initial dating.”

I had to think about that for a moment. I actually wrote it down, I even think my brain short-circuited for a moment because that was in fact the absolute greatest analogy I have ever heard about Venture Capital, EVER.  Holey hole in a donut, Batman! She’d nailed it straight on the head.

To read why venture finance is like dating, read Matthew Crowe’s column.

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