36 hours in my Silicon Valley

The NYT travel section featured Silicon Valley in its “36 hours in…” column recently, and wow did the article make us sound duller than dirt. It was a combination of stuff no one ever does (hanging out in Los Gatos boutiques??!), factually incorrect statements (Antonio’s Nut House is anything but “low-key” according to the police blotter), and ideas that are right but for the wrong reasons (Friday afternoon at the Rosewood bar is allegedly “cougar happy hour”, the VCs are getting pitched but not the way the NYT thinks). But the piece did get me thinking that maybe I should write down some of the things my out-of-town guests like to do when they visit.

First off, there’s no way you want to stay all the way out in Santa Clara unless you’re at a convention there; also neg the Rosewood unless you’re on a fatty expense account and love the idea of being in the middle of nowhere next to the freeway. Dinah’s in Palo Alto is the spot: it’s historic, centrally located just off a bike route, and includes a rather upscale tiki bar called Trader Vic’s with pupu platters and zombies in case you need a handy refuge.

After you check in on Friday afternoon, I’d personally start on University Avenue in Palo Alto to see some entrepreneurs right away. Head straight to the University Coffee Cafe (the sign just says University Cafe, but everyone adds the “Coffee”), where you want to sit next to a table of two men — one of them preferably nerdy-looking and/or saying “value proposition” a lot. Note how shiny are the eyes of the entrepreneur… although whether the glaze is optimism or desperation is never quite clear. The coffee is nothing special here, the floor is unsettlingly tilted, and the reserved seating policy is baffling… but it probably has a higher density of entrepreneur-funder meetings than any other place in the world.

After that, you’ll need a drink. Cougar Happy Hour at the Rosewood actually sounds mighty entertaining, so I’d head up there for a fancy cocktail before returning to California Ave for dinner. If you’re feeling flush, two ex-Nobu chefs serve excellent sushi at Jin Sho; or Palo Alto Sol offers yummy “cocina poblana” (food in the style of Puebla, Mexico). Antonio’s Nut House on a Friday night will be filled with Facebookers and grad students, giving you the opportunity to marvel firsthand at Silicon Valley’s infatuation with youth and novelty. I would not personally eat anything there, or drink anything without wiping down the lip of the glass, or use the bathroom if at all possible.

On Saturday morning you will definitely want to see redwoods. The best spot in my opinion is Purisima Creek Redwoods in Woodside, the town where all the venture capitalists live (VPs prefer Los Altos, while CTOs for some reason lurk in Portola Valley). Eat breakfast at Buck’s, to get the full flavor of Woodside’s old-California small-town facade; then CAREFULLY thread your way up Woodside Road to Highway 35 (Skyline). On Saturday mornings this road belongs to packs of road cyclists, because Silicon Valley is the capital of the sport. A lot of these guys put more miles on their bikes every year than you do your car, and they don’t even necessarily commute or race… they just love hammering up the hills.

The awesome thing about Purisima Creek Redwoods is that you can hike for hours… or visitors of any age and ability can simply enjoy the deliciously scented Redwood Trail. Sequoia Sempervirens, the Coast Redwood, can be identified by a flat needle with a groove down the center; and the cones are only about the size of a nut. At the right times of year, this forest is filled with naughty mushroom-hunting Russian immigrants who seek out delicious fungi in blithe disregard of your silly American laws.

One oddball tip for finding Saturday afternoon activities in Silicon Valley is to check the calendar of the Silicon Valley Bicycle Coalition. Their members (I am one) provide “bike valet parking” at Stanford football games, art festivals, and other major happenings along the “Caltrain corridor”. If you like to ride bikes, you can rent or borrow a bike easily and use the newish “bike directions” feature on Google Maps to tap into the network of bike lanes and trails in the area. Even if you don’t feel like mingling with the masses at an art festival, you can easily pedal over to a bookstore — Rasputin in Mountain View for used, or Kepler’s in Menlo Park for new — and pleasantly while away the afternoon.

No one can possibly say they have visited Silicon Valley without gorging on Indian food. My visitors always enjoy the South Indian specialties called vada (savory chickpea donuts) and dosa (paper-thin crepes) at Udupi Palace in Sunnyvale, where the food is delicious, super cheap, vegetarian, filling, and probably different from the Indian food you can get at home. Before dinner, I like to take my friends to watch the sun set over the decades-old apricot trees at the Sunnyvale heritage orchard. Before it was called Silicon Valley, this area was known as the Valley of Heart’s Delight, and it was a famous fruit-growing region… of which this small plot of Blenheim apricots is the last vestige. If you are extra-eco, you might also enjoy a quick trip to nearby Full Circle Farm, an 11-acre working CSA on the grounds of a public middle school.

After parking back at Dinah’s, walk over to Dan Brown’s Sports Lounge to meet the forgotten townies of Palo Alto — the restaurant managers, schoolteachers, bookkeepers, and carpenters who constitute the “normal” part of the population. On a Saturday night you’re unlikely to run into very many high-tech workers here… but you can get quite the education on the middle-class squeeze in a part of the world where the median income is in the six figures. Or you can just enjoy a shot and a beer, televised sports (hockey season is the best because you can see how successful the Sharks have been at bringing their icy sport to the area), and a little dancing.

Sunday morning means dim sum brunch. The best place to go is Cupertino, one of the increasing number of high-achieving California towns run by Asian immigrants. The mayor of Cupertino is Chinese-American, as is the entire city council and most of the residents. Unsurprisingly, the Cupertino school district is so renowned that houses located within its borders command a substantial premium over those in neighboring Sunnyvale. You want to get to Joy Luck in Cupertino Village before it opens at 10AM, and be sure to get the pan-fried shrimp and chive dumplings. Afterwards, a little stroll through Ranch 99 supermarket next door is always fun and reinforces how much Asian immigration there has been to this area.

If you have time left, the NYT’s suggestion of a quick visit to the Mountain View farmers market is definitely a good one. Unlike most such markets, this one operates year-round although there are more vendors in mid-summer. The quality and variety of fruits, veggies, meats and prepared foods are pretty dazzling, especially considering that every little town in Silicon Valley has a farmers market like this. Take special note of the Asian vegetables, and the amazing variety of baby greens — and pick up a picnic lunch for your plane ride home, after your weekend in Troutgirl’s Silicon Valley.

Game culture and engineering culture

I’ve never liked games. I didn’t get into D&D or Pacman as a teenager; bridge and poker put me to sleep about the time most people feel they’re just getting warmed up; I lack the reflexes for video games, even really slow ones like Wii Bowling or Sim City; and I can’t even imagine learning the rules to Settlers of Catan (although it always amuses me to hear players muttering things like “I must have sheep!”). On the two occasions I’ve forced myself to gamble in Vegas — on the nickel slots, no less — the experience was duller than life itself.

It’s probably the area in which I am the least engineer-like, and I’ve always been somewhat self-conscious about it. A shared love of games is embedded in engineering culture to the extent that people have become completely lazy and herd-thinkily unquestioning about it. Programming classes are almost invariably taught using games as the use case of choice. The vast majority of job interviews in Silicon Valley feature “brain teasers” that are supposed to measure your “raw horsepower” by means that are even more bullshit than the GREs. After hours, game nights are one of the most common social events in the Valley. Even my beloved Rands in Repose, in most matters the most reasonable and insightful of men, unhesitatingly defines nerds as those who most love toys and puzzles. I wonder how many non-gamers — who I’m guessing are mostly chicks — see this type of stereotype perpetuated over and over before deciding engineering must not be for them.

I really struggled with this “deficiency” for a long time, until finally it occurred to me: it’s not GAMES per se that define an engineer. I think a more general formulation might be that engineers are drawn to meaningless technical challenges with lots of rules and/or quantitative data (e.g. “scores”) to geek out on — and by that standard, I am easily in the fold. It’s just that interviewers don’t think to ask whether you’ve undertaken bizarre chick tasks like designing knitted garments using mathematical principles, planning long trips while optimizing over multiple variables, calculating the gear ratio when converting your bike to a fixie, or embarking on Iron-Chef style challenges to maximize the amount of nutrition per calorie for a given menu.

My point isn’t that games are bad, but that they’re limited and inevitably exclusionary and quite likely somewhat gendered. What if you, as an interviewer, had to expand your notion of “general interest” domains? What if you just weren’t allowed to ask puzzle questions? What if you were specifically enjoined to judge candidates’ interests by their real-world applicability — in which case trip planning would come in miles ahead of Grand Theft Auto or WoW for most of us? How would engineering be different?

Huge hidden audiences

I was at knitting camp (yes, knitting camp) last month when I learned something staggering. I’d estimate the average age of the ladies to be near 50 years old; and almost all of them listened to podcasts all the time. There was a brisk trade in tips for how to find, download, and enjoy podcasts from all over the web, for those few who weren’t already hooked on the habit.

Now to be honest, I’m not sure I’ve ever sat through an entire podcast; and I’d always sort of considered them an intermediate stage on the road from blogging to vlogging, like mesohippus or Neanderthal man. But then I realized that this is only true for people like me who spend all day long in front of the computer on fast internet connections. It turns out that for a lot of women it’s far more convenient to enjoy podcasts while they drive, wait around during appointments, do chores, cook, or practice time-consuming crafts. I also sort of suspect that listening is a skill more women have learned to enjoy 🙂 — a lot of them, it turned out, were devoted fans of NPR and recorded books.

Now I found these ladies to be affluent, sophisticated, life-affirming, eager to try new things, and technically capable if motivated. I imagine that women beyond the “children living at home” years control an awful lot of the wealth in this country, and have a disproportionate effect on many political and cultural organizations. The vast majority of my new comrades though told me that they found a lot of the web sort of… not very relevant to their interests. They didn’t watch videos, they didn’t read blogs, they didn’t social network except specifically on one knitting site, they weren’t interested in gossip or celebrity or mothering or beauty or any of the traditionally “female” categories on the web.

This is all by way of saying that if I — a middle-aged female — can ignore this huge and affluent audience, I’m kinda thinking you might too. Certainly your VC is unlikely to push you towards an audience that represents his mom or maybe his first wife 😉 — he’d rather pretend to be a 25 year old boy forever. What other huge audiences are lying just outside our field of collective vision while we huddle around San Francisco Bay sending witty 140-character quips to each other 20 times a day? Maybe we better get out there and find out sometime.

Hating on female websites

This is not a diss of Mashable, cause they know I love them… but may I humbly submit that their list of top 10 social networking sites for women made me throw up in my mouth a little? Umm… do you not see a certain THEME in your choice of sites? Hint: if a woman is neither a mom, nor does she think lip gloss merits more than a 2-minute glance at the drugstore — or even if a woman IS a mom and loves lip gloss, but doesn’t define herself that way — there’s no place for her in your taxonomy of chick sites.

I’d say the Huffington Post offers a strong community of people interested in organizing politically around what are often trivialized as “family issues”. Personally I enjoy Jezebel’s snarky takedowns of media images of femininity, which are all the more powerful because the writers and commenters acknowledge their allure as well as their danger. Salon has a proud track record of keeping us informed about political and social news affecting women (especially valuable for non-US news) and highlighting developments in the feminist blogosphere. And if Etsy isn’t primarily a site for women, I don’t know why not… and a lot of them turn out to have some interesting stuff to say about the personal (having a happy life while not making a huge income) being the political (eliding the division between career and home by means of not buying into “normal” consumerism). Unfortunately I can’t say I’ve found the perfect community for hard-core career-minded women, especially those in “traditionally male” fields… but when it happens, I’ll be there.

More importantly, many social networking sites — Facebook, MySpace, even GaiaOnline and Piczo — are now de facto “female first”. Even if the number of registered users aren’t overwhelmingly women, the gentler sex tends to be far more expressive and engaged on these sites. This has enormous implications for the whole business of technology — because for the very first time in the entire history of Silicon Valley, our “cutting-edge customer” is not a white geeky guy buying something from a white geeky guy… but a young woman talking to other young women. Facebook and MySpace ARE women’s sites now… so how come the media keeps shoving us in the ghetto of iVillage or Yahoo’s putrid Shine?

Business model questions

Lately I’ve spoken on a lot of panels, and for some reason I always get asked: what is your business model? This is one of those questions that people think make them sound sophisticated and hard-nosed, when in fact it is a neon sign that the person is a n00b.

Basically there are only 3 business models that apply to consumer internet businesses:

1) Advertising
2) Commerce
3) Subscription

Seriously, that’s it. You can charge a relatively small number of people for the privilege of using your site; or you get a larger number of them to buy stuff that you’re selling; or you get them an even larger number to want to buy stuff that someone else is selling. It doesn’t take a genius to understand how this all works.

So what is it people really want to know? Do they want me to detail exactly how Facebook apps split revenue? Are they expressing fundamental skepticism about one of the standard business models (seems like most of the people who ask this question are suspicious of advertising in particular)? Are they seriously expecting me to whip out my revenue projections? Or it is just that the Web 2.0 blogs talk a lot about business models, and distant readers are picking up on that? Tell me what I’m missing here, because I feel like I’m not getting it.

The factors of entrepreneurship

One of the ways I know that we’re in a bubble is the frequency with which I am now meeting intelligent young men who sincerely and with every appearance of unselfconsciousness tell me that they want to be founders of startups as an alternative to joining the workforce and learning their trade. I had forgotten how often people said that in 1999, given that those same people spent the next 5 years strenuously decrying the irrationality of entrepreneurship. Just as every young man in the Bay Area secretly imagined himself as the next Marc Andreessen back in the first bubble, now all of them apparently look upon Mark Zuckerberg with envy.

I dunno if it’s a gender thing or an age thing or what… but I find it almost impossible to understand this mindset. Like my friend Naval Ravikant — a man steeped in entrepreneurship and considerably in love with it — says: if you just want to make a lot of money, go be an i-banker or something. I would never have founded a startup if I hadn’t felt compelled to do so, and there are a lot of days I wish I were a team lead again.

I was going to subject you to a big rant called “Paul Graham wants to sell your sweet young ass”, about how most of the people who are telling you to go off on your own are also financially interested in the phenomenon of selling teams of young engineers to big companies… but then I decided it might be more helpful if I just spoke from my own personal experience about the many, many, many assets — the so-called factors of production — you require before you can legitimately found a startup with any statistically-meaningful chance of success.

I should first say that success means different things to different people. If you’re 20 years old, you might be pleased as punch to build something and get a few hundred grand for it a few months later. And hey, as long as you don’t get all kinds of wacky expectations from the experience — if it’s just a way to get a condo and a nice car and a good job — then more power to you. Go forth and build Facebook apps as fast as you can! But I’m sort of assuming that all these guys I’m meeting are not that realistic — that their aspiration is more YouTube than Reddit — and that in fact they’re pretty much interested in what we call the “venture-backable business”. So please keep in mind that my comments are mostly applicable to the latter case rather than the former.

With that caveat, this is what I’d say would be the bare minimum you need before you can found a venture-backable startup:

* EITHER a substantial work history (e.g. you were a key contributor to a very well known product) OR hundreds of thousands of users of your product OR a serious computer science background (think PhD) with major patentage in the relevant area. If you don’t fall into at least one of these three buckets, it will be exceedingly difficult to get initial meetings with any funder much less convince them to invest.

* A core team. These days the initial team must be almost entirely engineers, and they must be willing to work on your product for essentially no money until the demo stage at least. Among other things, this proves that you have sufficient powers of persuasion or management or hypnosis that you can serve as an executive for a little while.

* Some source of “enough to live on” money for you and your core team for about six months. Without this, you are fatally at the mercy of funders and will be unlikely to get a deal on terms that will make you happy for very long. Actually without 6 months of cash, you probably won’t even be able to get through the funding process even if things go spectacularly well.

* Excellent communication skills, both written and verbal. Pitching is no joke — you will need every scrap of ability to convince others (often extremely skeptical others) of your vision. This is one of the most mysterious factors, because you often can’t tell how charismatic a founder really is after they have already been successful — by that point they’re completely hemmed in by legal issues and PR bunnies who prevent them from speaking their minds — but you should assume they had the ability to communicate their ideas effectively.

* A billion-dollar idea. You better be able to say how your total addressable market is multiple billions of dollars, and how your share is going to be at least $100 million a year, and how you’re going to IPO or sell for at least $1b. This is another mysterious factor, because often startups have to change strategies or get bought for a lot less than this before they can really execute on the vision to that level… but believe me, they wouldn’t have gotten VC money if someone early in the process didn’t think that they could be worth a billion dollars someday.

* Friends. Along the way you are going to need dozens if not hundreds of small favors from other people in the community: introductions, blind reference checks, recruiting help, etc. Silicon Valley is a small town, and it’s hard to even buy the necessary goods and services without being introduced to vendors by someone. Hopefully your karma piggy-bank is good and full.

* Mental and emotional equilibrium. This has actually been one of the hardest factors for me, and I suspect is the biggest barrier for most women. It’s so easy to lose perspective — the most common way is by being overconfident and overoptimistic, but it’s also possible to go the other way and give up — that I would say it’s the #1 reason early-stage startups fail.

OK, so this is just my personal opinion after almost 8 years of the startup life including 2 years of the founder life. But don’t say Troutgirl didn’t try to break it down for you… do the research for yourself and see how many of your exemplar companies did or did not fall into these categories. If you can’t command all of these factors of production, I would humbly suggest that you save yourself a lot of pain and instead find another team that DOES have most of the factors, and then sign on to that team as an early member.