200 First Dates


gp055767-245x300I’m not a VC. I’m barely an investor. I’m a wanna be. I fall in love easily. I believe too naively. I don’t see hurdles I see a fun rubrik’s cube. I like taking the leap of faith because that’s what we are taught to do – go “change the world,” they all told me (I also like to spread the blame). Despite the fact that most leaps end somewhere at the bottom of the chasm, the junkie in me gets back up again and look for the next most impossible cliff – rinse & repeat.

So this muckerlab thing . . . . is different – making binary decisions instead of sitting in the other side of the table, trying to convince someone else that nothing is impossible. I’m sure I will become calloused, jaded, and be able to say “no” in 50 different way real soon. Right now though, I feel like I’m 18 again, starting to date for the first time (yes, I’m a late bloomer): awkward, brash, insecure, excited, insensitive, unsure, too easily seduced. After about 200 “first dates” with entrepreneurs, the meetings are starting to blend into one another. Typically, they all seem to follow the same 5 or 6 patterns . . . .

“Say Anything . . . ” His/her reputation precedes him/her. I know PG has called him/her twice already. Hell, even the real VC’s are sniffing around. I get there 10 min early – he/she is late and I check my email four times to make sure I’m not at the wrong place. The entrepreneur looks good in jeans. For the length of the meeting, I pretty much nod my head and smile eagerly the whole time. I try to convince the entrepreneur I can introduce him to Larry Page and the Pope – and both will take him on a ski strip on their private jets – most likely together. He/she gets up and leaves and casually mentions that he/she needs to run to a meeting with Sequoia. I stay seated slumped . . . wondering what brand of jeans he/she was wearing.

“I’m Too Sexy . . “ – I’ve found that pair of jeans on Hautelook. I took this meeting because Joe from referred the entrepreneur to me. The idea sounded stupid on paper and even more asinine in person. It’s a mash up of all the hottest topics on Techcrunch except 6 month ago. I try to smile absently – I wish I know if Jeremy Lin lowered his assist to turn over ratio last night. The entrepreneur drones on about being the leader in the collaborative daily deal sourcing space. It was a “no” before I meet him/her – I listen for some nugget of information that will allow me to make up an excuse to say “its me, not you” – no engineer? unrealistic valuation? missing teeth?

“Ghost” – The powerpoint stayed on the first page. We started brainstorming on his/her strategy and product roadmap. We are both up on the whiteboard scribbling away. Unchained Melody plays in the background. I could see the future now. Billions of dollars, ringing the bell at NYSE, cover of ESPN Magazine, 2 kids, a dog and white picket fences. We both ignore our next appointment – 2 hours later still talking. We started with a hand shake and left with a fist pump and a hug.

Will: “Gee, what do you want to do tonight?
EntrepreneurBot: “The same thing we do every night, Will—try to take over the world!”

“The Graduate” – The handshake was firm. Screw jeans, corduroys are the new black. The market is huge he/she tells me – I couldn’t get a word in. The entrepreneur speaks in fast staccato voice occasionally punctuated with hand gestures. He/she moves on to the team, demos the product, and tells me the litany of fortune 500 companies that is ALMOST piloting their product. He/she then tells me about all the people we both know, praises me for being the most insightful person they’ve spoken to, and my deep knowledge of cold fusion. I forgot to ask about the company’s engagement metrics, their pricing model, the stratospheric valuation, the fact their CTO seems to be based in Moldova. Doesn’t matter – if he/she can seduce me, he/she can convince anyone. The Newtonian law of physics doesn’t apply – we are now into quantum physics. I strap on, close my eyes, and wait for the rocketship to count down to zero.

“Dazed & Confused” – I don’t get it. Everyone told me this is the next big thing. I still don’t get it. I don’t know why anyone would buy this – but apparently they are – 20,000 units and counting. I hate the idea, the founder (ugly jeans), the color of the website. But every slide has a graph going up to the right. Every number ends in a B. I still don’t get it. I must be the stupidest guy in . . . . Santa Monica?. . . or worse . . . old, over the hill, a dinosaur whom time has past by. Before the entrepreneur figures out how uncool I am, I tweet out how I think I just found the next Google . . Instagram.

“10 Things I Hate About You” – Erik told me I HAVE to meet them, I was skeptical. The powerpoint was barely decipherable, the emails was in all caps, they had no idea what Instagram was (how unhip), and they never worked at Google or Facebook. Even their domain name pissed me off. BUT . . . the founder was persistent. He/she didn’t know how to use powerpoint because he/she rather be coding (I feel ashamed). The entrepreneur knows more about the technology and problem than anyone else. This is a diamond in the rough – a “makeover project.” Nerds can look good in jeans too. Its like discovering Skype in the caves of Estonia. . . I’m not just going to be super rich – people will actually think I’m smart too. Muahahahah.




arrow GO BACK