Illustration by Mark Zingarelli
THE SERIAL DATER, 32
SHE WANTS TO CUDDLE; HE WANTS TO CODE
I first started dating tech guys back in high school. One of my first boyfriends built websites for local companies. Then I dated a guy who ran his own tech-support company in SoMa. After that, it was a startup founder. I started dating in tech because I’m attracted to smart, intelligent guys doing something creative in a nerdy way. They get caught up in their own world, but I actually like that, because it gives me a lot of freedom to have my own life. Being a woman in San Francisco, the tech dating scene is a gold mine: You go to a tech party, and without even trying it’s like you’re Miss America. A lot of the guys are shy and immature, and they approach girls like it’s a middle school dance. It’s kind of hilarious, but it’s exciting, since you never know who’s going to be the next Instagram guy.
Behind the scenes is interesting too. Guys will hide in their break room at work, shooting slingshots, throwing balls at each other, and playing Guitar Hero nonstop. At first it’s fun, but after a while it starts to feel like you’re dating a member of a frat house. The brothers don’t really care about you, but as long as you’re dating one of their own, they’ll be your friend.
Also, the sophomoric stuff continues in the bedroom. Their sex drives change, depending on what’s happening at work, more than with other guys’. If they’re about to launch something, it won’t matter if you’re walking around in lacy underwear—you still won’t get any attention. One guy I dated would make a beeline for his iPhone right after sex. There was no cuddling, just straight back to the screen.
THE VENTURE CASSANDRA, 42
EXPOSING THE VC HOUSE OF CARDS
I'm in a different part of the venture business than most VCs, because I work as a technology investor and executive. Rather than competing directly with other firms to be the first one in on an investment, I’m going to all the funds and investing behind them. So the upshot is, I have relationships with the majority of partners at the top equity firms. I know everybody. Which means that I get to see how the industry works on a macro level.
Now here’s the deal: People have this perception of venture capital as this very seductive, sexy, money-minting industry.
But in fact, the dirty little secret in venture is that almost no one actually makes any money. Everyone loses. If you’re going to take away a lesson from this interview, it’s this: Most people in venture lose money most of the time.
That’s a fact. Venture returns over the past decade have been zero to negative. All the money is being made amongst 8, 9, or 10 firms. That’s it. You wanna know how most venture firms stay alive? I’ll tell you: It’s all the management fee. Say you and I want to start a venture shop. We raise our first fund—100 million bucks. We take somewhere between a 2 to 2.5 percent management fee on that $100 million over a 10-year period. Come hell or high water, whether we’re making money or losing money, we’re taking a $2 million to $2.5 million management fee every single year. For a huge percentage of these venture shops, that’s their livelihood. And the pension funds, the universities, the family offices—all of these institutions that are participating in venture funds—have lost a lot of money.
Now, here’s what’s fascinating. You’re seeing this major shakeout in the venture business right now. You’ve got established funds that aren’t able to raise the needed capital for the next fund. You’re going to see some legacy firms either severely contract or go away altogether. Take Kleiner Perkins, one of the most venerable firms in the world. They’ve had a lot of issues recently, and I’m guessing their next fund will be a lot smaller than the current fund. So you’ll see a firm that has a $600 million fund, but their new fund will be more like $200 or $250 million. That means the firm is going to contract, and a lot of people who were partners are no longer going to be partners.
I guarantee you, the ones who are left standing aren’t necessarily the talent. Because the other dirty little secret of venture is that almost all the deals get sourced by young guys who don’t get a big portion of the management fees, because they didn’t found the firm. These young guys source the deals, and then it’s the older guys who take all the credit and all the carry—the money. So when this shakes out, the older guys are going to be left standing, and the younger guys—the talent—are going to be kicked to the curb.
One of the only venture models that works now is the founder model. Think about the pitch for Peter Thiel’s Founders Fund. It’s brilliant: We’ve founded companies successfully, so let us fund yours. So you, the young VC, with lots of connections but no carry, why would you go work for those investment banking–like guys on Sand Hill Road? Same thing with the entrepreneurs. Founders Fund, Andreessen Horowitz—they’ve done a really, really good job of appealing to the startup-founder mindset: Come work with us, because we’re engineering dorks too, and we’ve done it. And all these legacy firms are trying to get access to that circle, but they can’t. Entrepreneurs want to work with other entrepreneurs.
There’s even a paradigm shift in where the deals are getting done. It’s San Francisco, not San Jose or Menlo Park anymore; it’s not Mountain View; it’s not Cupertino. And it’s fascinating to watch. I mean, Peter Thiel doesn’t even go down to Sand Hill Road anymore—he thinks it’s a waste of time. Founders Fund is over here in the Presidio. And Benchmark Capital just opened a major office around Sixth and Market. It means that a lot of the young talent—and the companies they’re working for—want to be here. These guys don’t want to live down in suburbia. They want to hang out in restaurants, meet girls. Mark Pincus from Zynga or Kevin Systrom from Instagram would rather go to Park Tavern and eat some good food and order a nice bottle of wine. Play golf? Go to a country club? NFW. No way. These guys are made differently.
THE EXISTENTIAL CODER, 25
SHE'S NOT PROGRAMMING; SHE'S SCULPTING
It's so bizarre: All of my friends who are not in tech are barely scraping by, but if I were to look for a job right now, I'd find one in a week. There’s an extremely high demand for great coders. People are always trying to recruit me to work at their “brother’s awesome startup,” or some such, and fluffy job offers are a dime a dozen. They can’t abuse me at work the way other employees get abused, because they know I’ll walk away.
The fact is, I love it—coding is like being a sculptor. It’s magic—I’m making something out of nothing. When I’m in the zone, I’ll blink and it’s been five hours. I’m not thinking about anything else in the world. A professor once told me, “It’s like getting a degree in pyrotechnics 40 years after the invention of fire.” Also, it feels so relevant. I mean, everyone has a phone, and the world is running on applications that I help write.
But it’s not for everyone. You have to love getting lost in technical minutiae. And sometimes I feel like I’m drawing circles in the sand: Technology evolves so quickly that all the codes I’m writing now—all of my work—will be obsolete in a year. I have to look at it like an existential practice in impermanence.
THE DOG WALKER, 30
"I HAVE TO REMIND THEM THAT THEIR DOG IS NOT THEIR BABY.”
Because a lot of my tech clients are in their late 20s and early 30s, the dog's like a trial run to having a kid. But sometimes clients personify their dogs too much. One guy called me and said he thought his dog was depressed, but he didn’t want to take him to the vet because he was afraid of traumatizing him. I had to tell him that the dog is a dog, something my non-tech clients seem to realize.