As a kid, I put things into buckets to categorize them. I’m a mathematician, so this always made sense to me. I’d look at a horse, a donkey, and a mule and say, “Yup. Got it. File it in my memory bank.” Then my mother would point out a zebra, and my brain would implode. Thanks Mom.
But the point is that people like to classify things. Square, triangle, rhombus; kingdom, phylum, class; one fish, two fish, red fish, blue fish.
What’s fascinating is that people also like to classify other people. And there are no worse perpetrators than those in our respective startup ecosystems. I’m not faulting anyone. It comes naturally to us. But here’s the rub. There are two main constituencies in our world: investors and entrepreneurs. We often hear VCs talk about entrepreneurs in public forums. They regale us with their classification system, the entrepreneur phenotypes they look for (or avoid) in an investment. They create caricatures. They chuckle about the “used car salesman CEO,” the “unlikable savant co-founder,” the “arrogant rockstar,” the “dropout.”
It’s all in good fun, of course, and entrepreneurs are just as guilty. The difference is that VCs mock us in public while entrepreneurs usually bitch behind their backs.
What follows is a handy guide to VC classifications.
Name: Arrogantus the Bubblerider
Average Age: 57 ½
Sailboat: Two of them.
Common Characteristics: Checking his Blackberry every two seconds; non-payment of attention; platitude regurgitation.
Field Guide: All hail king silverback! He hit it big during the dotcom boom when his search engine company went public. It was amassing a whopping $20,000 in revenue year after year and most of it was his grandmother clicking on knitting ads at his behest. Now works for a mega-fund and proselytizes while simultaneously determining what he and his third wife Kitty will do in Nantucket this weekend. He’ll take calls during your pitch, writes emails, and then, if you’re lucky, offers a silly amount of money at an exorbitant valuation. Then he’ll fire you, and replace you with some other silverback dinner-buddy that used to run a division of Staples.
Name: Zany McWhackypants
Average Age: Like Keith Richards, these guys are ageless.
Sailboat: Try a Harley Davidson, bucko…
Common Characteristics: Guitar buying; guitar tuning; sky diving; going to Vegas; trying their hand at MMA; failing at MMA; being awesome; drinking soy milk.
Field Guide: They’re the ax men of VCs. Instrument-playing, kite-surfing, rock-climbing, joke-telling one-of-a-kinds. They probably live somewhere cool, like Aspen. Smart as hell and accessible. They try to answer every email because they feel it’s the right thing to do. You can strike gold here people. Some are amazing both in the boardroom and on the basketball court. Ask for a Miller-Analogy before taking a term sheet because some are certifiably insane. Like Mel Gibson//Charley Sheen bananas.
Name: Captain No Personality
Average Age: Perpetually 30
Sailboat: You think this hair gets sun-kissed on its own?
Common Characteristics: Head-nodding; feigned empathy; occasional trying of hipster language such as “Can you do me a solid, bro?”; the giving of Dap.
Field Guide: Tall, good-looking, football star former ivy-league athletes who could put a hummingbird to sleep in midair. They make the occasional bold statement, offer connections, try to be your buddy and rarely follow up on anything. They fly under the radar. Usually named Tad or Ted. Maybe Tate. I digress. Plain yogurt anyone?
Name: Sir Chattwick Yapster the Third
Average Age: How old are you? Wait, let me guess then you guess. No wait, let’s do a word association. No wait…hey, is that a squirrel? Squirrel!
Sailboat: Too windy, can’t hear them talk.
Common Characteristics: They never shut up.
Field Guide: They sound like flight of the bumblebee, except in words. Thirty seconds into your pitch they’ll tell you all about your business. Voted most likely to make you commit hari kiri within 25 minutes of meeting them. Also voted most likely to make you wear earplugs. Sit close to the window. You may need to use it.
Name: Pattern-matching Paul
Average Age: 27
Sailboat: I own some Sperry Topsiders, and I’ve been to Newport if that’s what you’re asking.
Common Characteristics: Buzz-word slinging; HBR article Cliff-Noting; mimicking of those around them; hanging of MBA diplomas on Walls; weekend pounding of craft beer.
Field Guide: Walk into their office and 10 minutes into the conversation, you snap out of a buzz-word induced haze and realize the shoe company he referred to has absolutely nothing to do with your software company, but he’s doing a damn fine job trying to convince you that there is a “comp” somewhere in there. Chews on pens a lot. Makes him look pensive. Also, cashmere sweaters. The ones with the suede elbows.
Name: The CIA Agent
Average Age: Mid-Forties
Sailboat: I live in a castle, have 20 cars, and my roof retracts over my indoor pool. What do you think?
Common Characteristics: God only knows, but he must have a personal “Q” from the Bond movies working for him, because everything he owns can turn into a robot.
Field Guide: You can’t reach him via email, you can’t reach him via cell, text, UPS, carrier pigeon or smoke signal. For all you know, he’s in Istanbul helping avoid the next nuclear crisis. Or perpetually at TedX. Even his assistant is mysterious. Better off just waiting until he contacts you. (Also known as “Where’s Waldo?”)
Those are a few stereotypes I have met on my entrepreneurial travels. (Also, after this post I’m probably never getting funded again, so please look out for me on Kickstarter.)
[Illustrations by Hallie Bateman]