Entrepreneurs! Fancy a hot date?

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.

The VC process is exactly like dating. This woman should get some kind of fricken award or something! It’s so true! So, all week I went on my merry way with this thought in the back of my head “VC is like dating… How can I turn that into something…VC is like dating… Hmm…" and then POOF! As fate would have it, Ms. Magic herself (Joanna) gives me yet more inspiration on the topic.

She sent me a few examples of what the venture capital process has been like for her:

– On courting (meeting the friends): there have been times they have sent their interns round to our place, they sucked and it made me think badly of the firm.

– Awkward conversations about whether we are "official or not".

– The oddness of asking if you are getting intimate with another person.(Because until you are official, it shouldn’t really matter)

– The getting "naked" in front of the VC in terms of financials, business processes, and documents.

– “By the time I say, ‘yes’ to this firm, I will feel as if we really have dated and are officially making this ‘commitment’ to each other.”  

What this entrepreneur doesn’t know yet is that this “commitment” is probably more like a marriage.  For better or worse, till death do you part.

Speaking from experience in both dating and venture capital, all you can do is give it your best. Years may go by, there will inevitably be ups and downs, but if it’s really meant to be then everything will work out better than initially anticipated.

I can’t take credit for this great analogy, but will say this: if there are entrepreneurs that are ready to start “dating” Huckleberry, the very first step is to ask me out.

The real question is, are you ready to get “naked”?

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