Fishy thoughts

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?

If you have just been waiting for someone to suggest a Team in Training superstar to support, feel free to go here and pledge your support to my friend Erica and feel great. Thank you — really, I’m truly grateful.

If you don’t yet know about the fantastic work that Team in Training does, allow me to mention that since 1998 they have raised $850mm for leukemia, lymphoma, Hodkin’s disease, and myeloma research. It’s their 20th anniversary this year, and I think you’d feel awesome if you pledged right now.

I’m always amazed how many people’s lives have been affected by blood and lymph cancers. Leukemia is the most common childhood cancer, but an awful lot of adult are afflicted by lymphomas too. My mom was just telling me about a friend of hers whose 11-year old son died of leukemia. If you ever hope to have kids, it would be awfully propitious to join in the fight against blood cancers. More to the point, one of Renkoo’s team members is a survivor, so it’s a cause near to our heart.

Team in Training also helps train runners, cyclists, and triathletes to go further than they ever thought they could. My sponsored athlete, Erica, went from total novice to riding a century in just a few months. I’m too big a wimp to follow her achievement except in a vicarious way — but I salute and support her. I hope you can too.

I’m trying to gradually reduce the number of books I own, in part by the simple expedient of keeping track of what I’m reading. I use a site called Goodreads, which does an OK job of helping me maintain a reading life-list.

However, the site has mostly made me realize what an incredibly anti-social thing reading is at heart. Goodreads is billed as a social network, and I’m connected to a few friends on there… but the social aspect is so desperately awkward that I’m considering disconnecting from it altogether. I’m not at all sure that I want to have a social relationship with anyone at all based around books; and if I did, I’m REALLY not sure I’d want it to to be with people I know from other contexts.

For one thing, the overlap between my reading tastes and those of my friends is essentially nil. I can’t get enough of books about death and cooking, with only occasional forays into other fields. I imagine my friends find notifications of my endless mystery novels and food essays as tedious and unenlightening as I find their literary bestsellers and modern classics. It’s unfortunately rather rare to like someone better once you suss out their taste in reading, although of course it can be a notorious deal-breaker.

The intriguing bit is watching the disparate ways in which different people use the site. A not-insignificant number of casual users seem to think the point is to list all the books they’ve ever read. I’m sure there are a bunch like me, who just decided to keep a list from some arbitrary starting date, never looking backwards. A lot of the hard-core readers use their lists to keep track of the books they want to read aspirationally; I personally list the books I tried but failed to read, because I’m big on failure. Almost everyone seems to go along with the five-star rating feature, but I steadfastly refuse because I’ve come to believe that sort of thing cheapens the relationship between a reader and a book.

In a sense I already belong to a fairly big social network based on shared reading… alumni of the College of the University of Chicago. We’re the lucky few these days who were force-fed a small set of great books (I use the term unironically) which we can assume all the other members are familiar with. But let’s face it, this type of education is clearly an eccentricity and a shibboleth at this point, and I understand it’s been quite a bit eroded even there. When you meet a fellow Phoenix, it’s practically a secret-handshake situation… except, you know, with more embarrassment.

I am worried about something I never thought I would have to worry about: that the Perl hackers of the world might be fading away.

When I first started out in the business, everyone knew Perl because that’s pretty much all there was for making websites with; plus Perl was already pre-eminent in the operations space. You could use Perl for grungy sysadmin chores, whip out necessary tools like Bugzilla, and produce elaborate all-singing all-dancing public CGI scripts too… there was really no downside. It was so ubiquitous in the mid-90’s that we used to joke that when industrial society finally broke down, its very last gasp would be the final running of some Perl cronjob somewhere. Après Perl, le déluge.

But I think now people are having to specialize much earlier in their careers. Young devs don’t necessarily see the same bet-hedging value to learning Perl — heck, I’m sort of convinced young webdevs these days don’t see much point to learning anything about systems and their administration (whippersnappers, grump). Probably the young pups of today see much more value in Ruby on Rails than Perl. Today learning Perl is a CHOICE, and that choice is to definitely go down the ops/tools path rather than the public-facing dev path… like shell scripting, I guess.

Since every web operation of any size is ultimately held together under the covers by Perl scripts and duct tape, I’m wondering what it means for the industry to see the pool of junior Perl initiates shrink rather dramatically. Perhaps in 10 years Ruby will be the grungy sysadmin tool of choice?

I once wrote that there’s no vegetable I don’t like, but since then I’ve realized that sugar snap peas are teh suck. They’re slimy cooked and chalky raw. They’re a Frankenstein’s monster of the veggie world: some agronomist named Dr Lamborn bred them from a mutant green pea and a snow pea, specifically to look nicer and have straighter pods. After 10 years of marketing, the damn things have taken over the world of frozen foods. Oh, and they’re patented — every sugar snap pea in the world comes from seeds hybridized by the Syngenta company.

An old friend asked me recently why I had decided to become a programmer in the first place, and I started trotting out my standard canned answer… when I suddenly remembered a different story that I rarely share. Sure I love the web and social software is keen and I’ve met lots of brilliant people here and entrepreneurship is ever so much fun… but you know, my life would have been completely different if I’d had even a little bit of savoir faire when I was in my early 20’s. If I’d had the slightest clue how to get a job as a management consultant after college, I’d probably be wearing a skirt suit and dragging a big carry-on bag through O’Hare right now. But because I was too lame to know how to write a resume and go on job interviews, I ended up learning Linux instead.

So my career shift was motivated by desperation as well as fascination. Would I have pushed myself into a completely new career path so hard if I’d felt I had easier options available to me? And later would I have spent so much effort figuring out organizational dynamics if my coworkers had accepted my ideas right away? Without all those periods of unemployment, would I have had so many opportunities to learn new and different things? Would I have considered it a true necessity to take a good hard look at myself and the patterns I kept reiterating by my choices? I’m as fundamentally lazy and self-satisfied as the next person, if not more so, and therefore as loath to do painful and difficult things unless they seem necessary for survival.

Having learned so much from so many “bad” experiences, I find that I am now rather suspicious — or even pitying! — of people who seem to have never known failure, humiliation, and poverty. And yet, I find that now I spend a fair amount of energy trying to help others avoid the best of all teachers! I try to make time for pretty much anyone who needs help getting a job, thinking through their career options, learning about entrepreneurship — basically all the things I never got much help with when I could have used it.

I always used to wonder about the phenomenon of ostentatiously self-made parents with spoiled-rotten offspring (maybe because I was so worried about being one of the latter myself). I wondered how it could be possible for a fully-conscious adult to be utterly convinced that only hardship creates the character traits that lead to later success — but also to raise their kids in an environment where it was literally impossible for the whelps to taste any of that salutary hardship.

But now I feel like I can finally understand just a little of what it must be like. It is genuinely anxious-making to watch young people suffer and struggle and blunder around. Also it’s fatally easy to convince yourself that no one else needs as much bracing negativity as you yourself did, that they can learn the same lessons with one-third less suffering. It’s probably more correct however to assume that it’s a mean zero distribution… at least some of the young people you encounter would actually benefit from MORE hardship and misery than you enjoyed.

Most cities go to a tremendous amount of trouble and expense to figure out how to best serve the people with a public transit system that is both comprehensive and comprehensible. New York, London, Paris, Chicago… look at maps of their public transportation systems, and a clear picture emerges of easy routes between the popular parts of the cities in question. For any of these cities, you could print a credit-card sized map that would let visitors get around within a half mile of any point they’d be likely to want to visit.

Look at a map of San Francisco’s public transportation system, on the other hand, and… oh guess what, you can’t even really see the whole thing on one page because there are 4 different major providers (not including cablecars, ferries, and long-distance transport). And the four providers never meet in a single point, unlike the carefully planned nexuses such as the one underneath New York’s 42nd Street. And there is hardly a single route that is even remotely visually comprehensible to a normal person.

The transit map is notoriously unparseable, a jumbled mass of spaghetti with routes every block in the downtown area but only a few lines going to some of the most popular entertainment districts in the city. Take one of the most straightforward routes, the MUNI 38X bus aka “Geary Express”. For the entirety of its route through downtown San Francisco it doesn’t run on Geary or even the next street… instead it runs on Bush (3 blocks away) in one direction and Pine (4 blocks away) in the other. Meanwhile the 38 and 38L buses run on Geary! How the heck would any visitor or casual transit rider be able to figure this out?

It’s especially incredible because San Francisco as a city seems to be so strongly united in valuing green causes, the visual display of information, and anything that reduces traffic and parking problems. Half the people I know up there are Ralph Nader-loving, Critical Mass-participating, urban planning-hobbyist designers! I generally believe that people get the government they deserve, but it seems so incongruous to me that San Francisco ended up with such a horrible public transit system.

Somewhere in the last few years, I lost the ability to aspire to trivial procedural resolutions like “losing weight” or “saving money” or “getting organized” or even “helping others” — which I understand are always among the most popular goals. There are evidently a lot of people for whom those issues are tied to what they genuinely don’t like about themselves or the ways in which they hurt themselves… but I don’t think I’m one of them. If I knew I were going to die tomorrow, I wouldn’t give a second’s regret to how big my butt is or whether my socks are all sorted by color.

My current biggest regrets in life all have a root cause that I’m sure will astonish the masses: I’ve almost completely lost the will to say things that other people might not want to hear. The irony! For all those years Troutgirl would not be shut up by fair means or foul — the more indelibly cutting the remark, the better I was pleased with myself and damn the torpedoes — but now I find that my lips are sealed for almost everyone.

I imagine many of you are thinking, “Being less critical is a loss?” Well… yes it is and you’re completely one-sided if you don’t see it. In the past I have many times helped people make more money, deal with looming career disasters, solve relationship problems, write better books, and generally figure out what they wanted to do in life by exercising critical skills. You could certainly argue that acuity — the ability to identify and interpret a hidden factor, to sift the important thing out of the background trivia — is a big part of what makes a good manager or mentor.

Part of it is doubtless simple middle-aged ennui; and everyone knows how many times my big mouth has gotten me into big trouble. Furthermore, I have responsibilities now that more and more tightly constrain my ability to just blurt out whatever is on my mind. But the truth is that I’m not afraid or even tired — I’m just increasingly isolated. I’m perfectly aware that the less you express yourself, the less you can expect anyone to understand you… and yet I express myself less every passing year.

I guess I’m not really bringing this post in for a classic “My New Year’s Resolutions 2008″ type landing. This may all be by way of saying… you get older, you have more regrets that you can’t redeem by New Year’s day.

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.

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.