Life on a Short Street

On the empty sidewalk opposite my house, I was toodling along on my bike recently — and yes, I was also talking on a cell phone with my brother — when I heard a driver yell, “HEY BUDDY, WHY DON’T YOU WATCH WHERE YOU’RE GOING?”

Before even looking up, I responded: “WHY DON’T YOU GO F*** YOURSELF?” Then I saw my neighbor, still so stunned he hadn’t quite erased the jolly, just-joking expression from his face, sitting behind the wheel.

My wife later reminded me that since our street diverts cars one block to the north and two to the south, I didn’t even have to look up to know that the only possible target for my bizarre spasm of aggression was someone I’d see every week for the next decade.

When you think about it, your whole life is like that street, much shorter than you once imagined, almost entirely populated by people you’ll meet over and over again.

But for a long time, I didn’t think about it. Until I was 15, my twin brother and I began every fall term by apologizing to our assembled friends for the way we were the year before, as if the coming year could make everyone forget the fleas we occasionally picked up from our dogs, or our tendency to yank on one another’s headgear in tussles.

It wasn’t until I was a hiring manager who called job applicants’ references that I considered how long people would remember all the ways you act up as an adult. I began to reflect on my greatest hits. It was like hearing your own voice on an answering machine, except instead of taking 30 seconds it seemed to take 30 years.

I now see amazing job candidates, some better qualified to run a business than I am, dismissed with the slightest gesture by some dude we dug up from LinkedIn. “Can you send us a few thoughts about working with Jerry?” we ask in a note. The message back makes the rest a formality: “Can I call you instead?”

When you’re younger, you never wonder what would be said about you in such a phone call. The whole world is a vast frontier, a life without consequences. You rage through it like an instinctive animal. If you think you’re good at something, especially at a software start-up, you let everyone know it.

But then you get to the end of the street and have to double back again.

The Shitake Hits the Fan

There has been over the past 18 months a Cambrian explosion of startup life, many incubated by angels and seed funds. And now the process of natural selection is beginning again.

I got back from the Valley Thursday and what I gathered from the people there is the same as what I’ve heard here: that many seed companies are having a hard time raising money.

Yes, second rounds are always hard, after you’ve built the product but before it has made much money. The difference is that today’s first-round investors are angels and seed funds, which sometimes aren’t even set up to participate in many follow-on rounds.

What’s made that worse is the market is becoming more cautious around post-seed deals. Everyone criticized the Wall Street Journal’s Pui-Wing Tam for being the first to notice a cash-crunch for seed-stage companies seeking follow-on rounds, but I think she nailed it.

Some early-stage entrepreneurs are now clawing at the walls, begging supporters for money and time. Many investors never promised more money or much time. The premise of some seed investments, especially from larger funds, is “optionality.”

Rather than making a serious commitment to a handful of seed-stage companies, larger funds are buying the right from many startups to lead a later round in the hope that one or two of them catches on with consumers.

One reason for this is that consumer internet investing has become a hit-driven business. Who could pick the next Twitter? When the question is one of tickling consumers’ fickle fancy, rather than a rational process of evaluating technology, it’s a crapshoot. So some investors play at the dollar tables, and roll the dice all night long.

This approach has led to the creation of more new businesses over the past 24 months than the Valley has likely ever seen. It has given entrepreneurs a shot at success many never would have otherwise gotten.

And some don’t need any more capital or advice beyond a seed round of financing. But I did, especially when I was first starting out.

I co-founded a company, Plumtree, that raised seed capital from Sequoia. Kirill, Joe and I closed the round, walked out to an ATM to check our balance, and began laughing hysterically.

Things went downhill from there. A co-founder left. Nobody bought the product. And we ran out of money. I felt like I was digging deeper and deeper into a hopelessly dark mine, looking for gold.

Then Pierre Lamond, the Sequoia partner on the deal, began working out of our office, acting as the virtual CEO.  Pierre made a point of being there the day one of his other companies went public. We looked at a news photo of all the smiling people, who seemed to be living in a gated community, on a planet I would never visit. Then Pierre said “that company was once even more screwed up than you are.”

I clung to that statement through Plumtree’s early days, and returned to it again when Dave and I were working out of an apartment trying to figure out how to make Redfin work .

To find a new lead investor to join Sequoia on Plumtree’s board, Pierre drove me all over Palo Alto and Menlo Park in his car. It was the first time I’d visited the Promised Land of the Valley itself, and it was nice to see it through his windshield.

I cherished the conversations we had on those trips: about how Pierre founded National Semiconductor, or built the Cray supercomputer. He asked me what I enjoyed doing outside of Plumtree and I said “reading.” He saw what a little stress-monkey I was and said I should spend a few minutes reading a book every night; it’s advice I still try to follow.

At each stop, Pierre promised he would work closely with the new investor on Plumtree, and possibly on other deals too. I was then released by my nervous handler to perform in the conference room like a zoo animal on The Tonight Show.

You may think it wasn’t really a fiasco, but one detail should suffice to convince you it was: at one point, I lugged a full-sized server around because we couldn’t get the product to work on a laptop, or over the web. I tried to get the server going under the table before the partner came into the room but sooner or later he  always asked, “What is that humming?” It was the sound of a thousand memory leaks spinning up the disk drive and every other internal gizmo into a panic.

That anyone gave us money was a miracle. But once we get the money, we prospered, eventually becoming one of only two technology companies to go public in 2002. I wondered why Sequoia went to such great lengths to get Plumtree funded when it would have been easier to write off the few hundred thousand dollars invested in our company.

And the simple answer was that Sequoia cared about its reputation and stood by its companies. Someone later told me that a Sequoia partner liked to say, “We don’t want you staggering around, with your fly down and a drink in your hand, telling the whole world ‘We’re a Sequoia company.’”

If Sequoia hadn’t saved us, I would have decided that my startup fling was folly. Plumtree would have just disappeared, and everyone would have thought it was a terrible idea. Redfin wouldn’t have the executives it has now, and neither would AdMob, Xoom, Atlassian, Zendesk, Piazza, The Climate Corporation or any of the other companies now being led, in part or in total, by Plumtree people.

It seems a shame to me that few of today’s seed-stage entrepreneurs will get the same support we did. I promise you, we were even more screwed up than you are.

The Age of Revenues

I was talking to a friend in Silicon Valley last night who told me about a consumer Internet startup that is generating tens of millions of dollars in revenue, with eye-popping year-over-year growth. What was striking about the conversation wasn’t the revenue itself, but that I’d never heard of the company it came from. This has happened half a dozen times in the past month.

What that means is that there are more Internet startups with massive revenue growth than I can keep track of, and I can keep track of quite a few. It means that when TechCrunch’s Sarah Lacy argues that high-revenue startups like Zynga and Facebook operate in a completely different universe than the rest of Silicon Valley, she isn’t completely right.

We heard the same argument from plenty of folks when we wondered what Mint would be worth now: that the increase in valuations of Zynga and Facebook are totally unrelated to those of earlier-stage startups, because only a few venture-backed Internet companies are generating serious revenues.

What I’m seeing instead is different: yes Zynga and Facebook are in the major leagues, but there is a very healthy farm system with plenty of prospects moving up through the ranks. This is why the broad-based increase in valuations isn’t just  inflation, but the result of Internet startups’ getting much, much better at generating revenue.

What happened? First, at the end of 2008 startups finally stopped listening to the most misinterpreted — and sometimes just wrong — advice in the Internet’s history: Chris Anderson’s insistence, just as Apple opened the iTunes store to software and venture funding hit the skids, that everything on the Internet be free.

To be sure, the idea of a free trial application is a good one, but many entrepreneurs became squeamish about ever asking consumers to get out their wallets. Music was Mr. Anderson’s primary example of a good that consumers would stop buying, but now Pandora, the company with the temerity to charge for music, is going public.

As we’ve argued many, many times before, as early as 2008, a whole new generation of entrepreneurs has learned from Steve Jobs to ask consumers to pay, early and often, for mobile applications like Angry Birds, or virtual goods in Farmville, or actual goods like clothes, textbooks and baby gear:

Startups have turned to the most direct way to get money: from their users. And consumers are ready to buy, buying software fast-food style on the iPhone, and shelling out for premium subscriptions on sites like Picnik and Animoto.

The change has been good, for startups and for the consumers buying their software, the quality of which has improved immeasurably over the past few years. Now, most of the companies that got serious about generating revenues are growing like crazy. It isn’t too stuck-up to call this change a new Internet era.

The first era was the 1990′s Age of Eyeballs, when every website sought to get as many visitors as possible, without regard for the cost of gaining each visitor or the revenues each generated.  The second was the mid-2000′s Age of Acquisition, when Paul Graham encouraged most entrepreneurs to build websites as features of a larger product, and the goal was to get bought by Google or some lesser light. Since big, unsustainable startups had failed in 1990s, small became  beautiful.

Now we are in The Age of Revenues, in which many Internet startups are maturing into big companies with big revenues. We’ll see more companies invest in large tele-sales operations — the whale-hunting salesmen are mostly relics, as small transactions have flourished like plankton — and we’ll see more companies grow, with more accretive acquisitions at much higher prices. And though there will undoubtedly be more ups and downs, we’ll see more public offerings too.

With great revenues come great power: a new generation of Internet titans. After years of insisting that the Internet had matured, nobody now believes that in two years the only Web behemoths will be Microsoft, Google and Yahoo. In fact, folks have begun to doubt that any of those three will rule the Internet the way they once did.

It’s an amazing turn-about. 2008 year wasn’t, as Sequoia claimed, the death of good times, but the birth of a new, long-lived era of broad and massive revenue growth. The new school of financiers at Sequoia were right about the global economy, which is still a disaster zone outside of Silicon Valley. They were just wrong about how entrepreneurs would react to it.

Friendship and Solitude

Have you read the wonderful, deeply counter-cultural lecture on solitude and leadership delivered by William Deresiewicz in spring 2010 to the West Point plebe class? I just found it via David Brooks, and can hardly recommend it enough.

Part of what makes the lecture seem so important is the audience hearing it. West Point students are the kind of people who could have gone to Wall Street or started a company two years out of school but instead will soon find themselves face down in the dirt of Afghanistan on Christmas day, scared and cold, leading people they’ve just met, under circumstances that would overwhelm folks like me.

But mostly, I love the essay because the old professor gives the plebes such strange and good advice. In the plainest terms, the lecture captures everything I’ve been feeling about these charming hoop-jumping robots Redfin has been interviewing at top-flight schools this fall  – smarter, more polished people than I am who’ve never had a goofy moment of pure curiosity, who never blew stuff up for fun or were allowed to make terrible mistakes, who never screwed up their transcript or their resume just to see what it would feel like to stop pleasing everyone else.

Interviewing such poised job applicants, I kept thinking this fall of Wagner’s complaint about Mendelssohn, who was more precocious even than Mozart and more lyrical: that he never lost control of himself. Drawing on decades of grooming Ivy League students, Deresiewicz argues that this control is crucial to being successful in society, but not to being a leader. His students are always thinking of how to get to the next step, but always on someone else’s stairway:

So I began to wonder, as I taught at Yale, what leadership really consists of. My students, like you, were energetic, accomplished, smart, and often ferociously ambitious, but was that enough to make them leaders? Most of them, as much as I liked and even admired them, certainly didn’t seem to me like  leaders. Does being a leader, I wondered, just mean being accomplished, being successful? Does getting straight As make you a leader? I didn’t think so. Great heart surgeons or great novelists or great shortstops may be terrific at what they do, but that doesn’t mean they’re leaders. Leadership and aptitude, leadership and achievement, leadership and even ex­cellence have to be different things, otherwise the concept of leadership has no meaning. And it seemed to me that that had to be especially true of the kind of excellence I saw in the students around me.

The essay argues that what a leader really needs is solitude — the kind you feel when completely absorbed in a creative project, or on a long car ride through an empty place. For me that solitude has come most intensely running up a mountain, all alone in winter, with darkness coming and the snow falling as thick as the air itself, running until I’ve thought through what to do with my life or decided how I really feel about God, running so far that I’ve started to get scared about making it back alive. Deresiewicz worries this solitude is being drowned out by modern life:

“Your own reality—for yourself, not for others.” Thinking for yourself means finding yourself, finding your own reality. Here’s the other problem with Facebook and Twitter and even The New York Times. When you expose yourself to those things, especially in the constant way that people do now—older people as well as younger people—you are continuously bombarding yourself with a stream of other people’s thoughts. You are marinating yourself in the conventional wisdom. In other people’s reality: for others, not for yourself. You are creating a cacophony in which it is impossible to hear your own voice, whether it’s yourself you’re thinking about or anything else.

What I love most about the essay is that it talks about  how the solitude that a leader needs — that anyone needs — is not incompatible with friendship, especially the friendship of one person, someone you know well enough to welcome into your solitude:

Introspection means talking to yourself, and one of the best ways of talking to yourself is by talking to another person. One other person you can trust, one other person to whom you can unfold your soul. One other person you feel safe enough with to allow you to acknowledge things—to acknowledge things to yourself—that you otherwise can’t. Doubts you aren’t supposed to have, questions you aren’t supposed to ask. Feelings or opinions that would get you laughed at by the group or reprimanded by the authorities… Instead of having one or two true friends that we can sit and talk to for three hours at a time, we have 968 “friends” that we never actually talk to; instead we just bounce one-line messages off them a hundred times a day. This is not friendship, this is distraction.

I was lucky to grow up always having a friend like this: until we left one another for college my twin brother and I lived in our own country, unassailable and determined. The French describe a newly married couple as, “alone, just the two of them,” a phrase that perfectly describes the feeling we’ve had together.

Over time, I’ve been lucky enough to make new friends like that, but lately not so much. I don’t know if I’ve gotten too old, or too busy — I’ve often just felt that I’m no longer gooey, that my identity has sadly hardened to the point where it can hardly accommodate the shape of a new personality. But Deresiewicz’s beautiful lecture convinced me that there are, at least, a few more kindred spirits out there, for all of us.

Headphone Culture

I just toured a startup the other day and what struck me while making the rounds was the fundamental sameness of the startup vibe: a handsome group of slack-jawed folks drowning out their ADD with 80-decibels of music.

Startup offices are supposed to have the buzz a newsroom once had, but often are sort of hushed, like a law firm. The floor plan can be open but only because everyone now has a thousand MP3s to pipe through their headphones. The environment is transparent — we can see what one another is doing — without necessarily being collaborative. It’s a little bit like the panopticon a philosopher once imagined would replace our prisons.

And it’s weird, and maybe perfect too. If a 1980s office-worker emerged from a time machine and walked around a typical office, he might be surprised at many things: gym-hardened 25-year-olds riding elevators to the second floor, the presence of computers on everyone’s desk, casual dress, Costco muffins but no ashtrays, the occasional ping pong table.

But what would surprise him most might be the popularity of DJ-sized headphones, worn by everyone from the lowest-level employee to the CEO. The time-traveler might feel about headphones the way we would if we learned that future office-workers will all wear goggles, so that they never see anything except what is on their computer screens.

Don’t we come to an office so we can work together?

I do, but then I don headphones to isolate myself. We have all seen offices with thousands of people like me — the size of a new country, with its own silent language and customs.

I catch myself deferring face-to-face discussion in favor of online chats and email — the growth of IM and the sales figures for headphones probably line up very nicely – just so I can finish listening to a song. I do this even though I can’t concentrate while listening to music unless I listen to the same songs over and over again. I do this even when, as is usually the case, I am wearing headphones without listening to music at all, just to block out background noise.

This tactic may be the latest twist on Virginia Woolf’s insistence on having a room of one’s own. At work I often think of her advice to keep windows open and doors closed: a way to see and feel the world while still preserving your own creative space. Now the office sights and sounds come to us via IM windows and email messages, popping up in a manageable corner of our computer screens rather than standing in our office doorways, demanding our full attention.

Sometimes, it’s good to avoid a face-to-face conversation. When I get back to my desk from a face-to-face conversation, I have to take a few moments to re-orient myself to the three-ring circus running on my computer, and I have to queue up my music all over again. The person I interrupted has the same challenge.

But usually, a conversation is essential. Whenever I disagree with someone, I try to do so in person because we end up reaching a fruitful compromise much more quickly. And whenever I need to collaborate on an idea, I get more energy from being in the same room with someone. I work at Redfin because I love the people here, and noticed I’m happier when I actually get to talk to them.

So whenever I think that maybe I should go chat with someone — I slowly take off my headphones — but never decide to email them instead. And whenever I’ve tried — a dozen times at least — to give up my headphones entirely, I lose control of my perimeter, and get less done.  Modern life will give us more and more ways to enter that isolated yet connected state, with open windows and closed doors. Our only challenge is not to spend too much time there.

The Story of My Life

When we think about what makes a life good or bad, we tend to focus on the key events: a small envelope on the counter, a basketball that rolls around the rim before falling in, the cold of a doorknob before you walk out.

After offering career advice to a young Redfinner last Thursday, Greylock’s James Slavet told me he should focus less on what you do, and more on how to think about it.

Conversations with James can have the commotion and intensity of a car wreck: there’s a lot going on that you have to pay attention to. Somewhere between noticing that Jamaicans acknowledge one another by saying “Maximum Respect” and an anecdote about “offensive” financing — not just offensive as in, “we don’t need the money” but offensive as in “that’s really offensive” — James mentioned that people are happier when they have a narrative for making sense of their lives.

I seized upon this tiny observation. I used to wonder why the circumstances of my life had hardly changed, yet I’ve been happier about them now than I’ve ever been. And I think the reason has been that I can fit those circumstances into a story.

At first, the story rationalized decisions I had already made. Now the story helps me make better decisions. Some people’s story is that they like helping others. Others live for their families, speak truth to power, experience as many new sights and sounds as possible, or imagine themselves as pirates. Making up a story to explain why you do things is a good idea for two reasons.

First of all, it makes sense of things, so your life doesn’t feel totally random. It’s easy to despair over having to read “Goodnight, Gorilla” for the 83rd time, or spending five hours tracking down one bug, but less so if you know that your children are what’s important, or if you’ve dedicated your life to the perfectionism of true craftsmanship.

And most important, a story makes sense of changes, in a way that can sustain you through a difficult transition. A story after all isn’t a painting; it wouldn’t have a plot if its hero didn’t change: Raskolnikov confesses, Rocky believes in himself again, Madame Flaubert falls in love, Francis Macomber stands his ground, Darth Vader turns on the emperor, Holden Caulfield comes home, Huck kneels before Jim.

At some point in my 30s, I decided that my story is that I like being creative, not  in a lonely artistic way — which is something I’ve tried with bad results — but in a social, productive way. The change from a romantic ideal of the lonely artist to something more humble and collective has made me much happier.

The change began a week before I started at Redfin, in Vermont, when I ran into someone who, I had been told, published the modern Great Canadian Novel. I’d never heard of it, and still can’t remember its name.

But I remember the writer, a gentle man with a long beard. He said he started only with a very precise idea of how he wanted people to feel at the novel’s climax, when a village had congregated around a winter bonfire. He talked about it as if it were a state function, where he could allow himself to get lost in the twists and turns of plot and character so long as he arrived at that bonfire, and how it made people feel.

I wondered as he said it if I would ever be able to capture a feeling like that. But I knew I could help build the bonfire. Even today at Redfin, I feel unsure of every product decision we make or financial metric we measure, but am very clear on what the company should feel like when we succeed. This is why I believe our deepest innovation isn’t our search site, or our home-buying service, but the company itself, which in ways large or small, can be a different collection of people than you’re likely to find every day, where everyone has ideas, and everyone can be a leader.

I want to be a part of that, and to do so, I’ve had to change: becoming more supportive and less in-your-face, more cautious about my own opinions and more receptive to others. I still have a long ways to go, but it’s the change that I’m proud of, not just the result that it has had. The change used to be painful because what I loved wasn’t my story, but the image of myself as I’d been my whole life before the story began.

Now I know some will say the story is beside the point, just the music that is playing in our heads while we do our little dance in the office and at home. But it’s easier to dance when there’s a song to make sense of it all. And there is nothing either good or bad but thinking makes it so.

Celebrity or Entrepreneur?

I was just reading Chris Dixon’s notes on starting your first company, and noticed that five of his eleven recommendations focus on becoming a social-media player: reading “all tech blogs every day,” starting to blog and tweet yourself, cultivating advisors in part to “build your credibility,” searching Google for your own name, and going “to all good startup events and talking to everyone.”

Chris’s argument for participating in your industry’s conversation is indisputable. But I’ve begun to worry that the risk for most entrepreneurs just now starting out is that they’ll spend far too much time worrying what the world thinks, and not enough building products or listening to customers.

Just reading the blogs that Chris recommends by name would, on Friday, have encompassed 134 posts, totaling some 60,000 words. This is nearly the length of Catcher in the Rye, a comparison that makes me sad just thinking about it. Even skimming the articles would take an hour. Writing your own takes longer.

I know that I’m hardly one to complain. I love contributing to this blog, and believe that communicating directly with the public is, more than ever, an essential CEO skill. But not before you have a product.

For someone just starting out, the celebrity culture now forming around entrepreneurs with thousands of Twitter followers is a sideshow. Almost anybody who works hard enough at social media can become the Weird Al Yankovic of the Internet, the kind of B-lister who hangs at the Playboy Mansion on a Tuesday afternoon, playing poker with people in bikinis.

But each five-minute interruption costs you 15 minutes of work, and building a product is a lot of work. So my advice is to take Chris’s advice, but ship first. What’s beautiful and precious about the opening six months of a startup is that you get to spend all your time in the garage, not upstairs entertaining guests.

Even after that, if your product takes off, you’ll have to say no more often than yes. In the past year, I’ve been invited to speak to the Singapore government (no), at the Hard Rock cafe (no), the island of Alcratraz (no), Yale University (yes), the New York Forum (yes), with a group of Parisian startups (no), and a rabbi’s Jewish gathering (yes), all about entrepreneurship.

Each invitation is an honor, but I mostly resist the urge. I read only two blogs regularly, TechCrunch and AVC, and often go days without consulting either one. I began contributing to this blog twice a week in 2006, but only after we launched our service, and only as a hobby. I have never once thought I should spend more time on it. Whenever I take time out to write a post, I nervously reflect on Coco Chanel’s insistence that there is time for work, and time for love — which leaves no other time.

Of course, making time for blogging can benefit your business: it helps you think through problems, it sustains what is weird and wonderful about your culture, it promotes your company. It has done all of this for Redfin. And Chris’s blog has done even more for Hunch. But Chris isn’t a first-time entrepreneur: his A-list following grew out of his first company, and his current company already has a fantastic service; he also has the rare ability to write well while remaining completely engaged, operationally and technically.

The risk that any other CEO faces with social media is that she’ll end up like Russell Hammond, the groupie-hounded rock star from Almost Famous who lost his way.  When William finally gets to interview him at the end of the movie, the teen-aged journalist asks only one question: “What do you love about music?” Russell sits up, turns the chair around, and leans in. “To begin with,” he says shyly, pausing and then smiling, “everything.”

If you asked Chris the same question about technology, I bet he’d give the same answer.

Jim Flatley Wasn’t a Recliner

Every time I get on a plane, I think of Jim Flatley, the vice-president of sales at my old company, Plumtree Software. Corvette-driver, hair-gunker, suit-wearer, sausage-eater, Jim was about as different from me as a person could be. It took us many years to become friends.

And because Jim was so very good at sales, which I once assumed was the art of turning customers upside down and shaking every penny from their pockets, it took me years to notice how generous he was. The first day I did was on a flight we took together.

As soon as we were aloft, I reclined back in my seat. Jim looked over in horror. “You’re just going to recline like that, wide awake?” he said.
“Yep.” I said.
“What about when the meal comes?”
“Even then.”
He shook his head. So far as Jim was concerned, reclining was fine for grandmas from Tulsa on once-a-year Christmas trips. But business travelers didn’t do that to one another.

I was surprised that Jim was so meticulous about airline etiquette. Commercial flight tortured him. He must have been 6’5’’. He didn’t like to crease his jacket by stowing it overhead. Whenever he started a new notebook, he carefully transferred a photo of a Gulfstream jet from the old notebook to the new one. If he saw me looking at the jet, he’d tell me his goal was to buy one.
“Fractional?” I’d say.
“The whole thing!” he’d say.

Jim never brought up the reclining issue again, but it stayed with me. I stopped reclining when Jim was around, then stopped almost entirely even when he wasn’t. The last straw was when someone reclined on me, leaving me almost no room to use my computer.

I fretted about this situation for years before asking for a ruling. “I’ll allow it,” Jim said. His eyes twinkled, either because he was pleased at being consulted, or because he was in the position of granting an indulgence to a lesser, more-recumbent being. I wanted to ask which it was. But I was at an age when feeling silly stopped me from asking a lot of questions.

Years later, Jim got a job running sales for Seattle-based Verdiem. We went out for dinner with a few other old friends, and Jim proposed we start with cocktails. He asked for my order first, and I suggested the only drink I knew, a Cosmopolitan — there was a time when I thought this order was cosmopolitan. Jim’s face froze, then he ordered Cosmos for the whole table. They came in pink glasses.

A month later, Jim was dead at 50 of a massive heart attack. Everyone loved talking about Jim, and everyone talked about him that day. It was already all past tense: is became was, you became him.

But Jim’s still with me. Rising up from Boston this morning, someone reclined on me. In a cycle that will outlast us all, I reclined in turn. But that cold aluminum button in the armrest acted like an on switch for the projector in my mind that re-plays everything I love about Jim. It reminds me that taking whatever you can isn’t savvy, it’s just selfish. I hear Jim telling me that on every flight. I wish you all could too.

One in Five Facebook Employees Has No Imagination Whatsoever

Whoa! Shocking news, guys. An engineer left Google for Facebook. The great Lars Rasmussen, creator of Google Maps and Google Wave, quit Google Thursday to join Facebook. This has, admittedly, happened before. In June, Matthew Papakipos defected from Google’s Chrome team. In May, it was mobile guru Erick Tseng. Even Facebook’s chef, Josef Desimone, was recruited from Google.

In fact, someone over at Google must feel like the coach of Cuba’s national baseball team. Of the 2,174 current Facebook employees with a LinkedIn profile, 378 cited Google in their work history, or nearly 1 in 5.  What’s remarkable about their decision isn’t the aplomb of Facebook recruiting, but the lack of imagination of Facebook’s Google recruits.

What’s the point of leaving one unassailable Internet platform where all your friends work for another unassailable Internet platform where all your friends work? It’s like getting a divorce to marry your wife’s sister.

I know, because I’ve been the wife in that situation before. When a colleague at a startup joined a competitor, my old partner Kirill Sheynkman had a very different reaction from mine. The colleague’s defection seemed shockingly traitorous to me but to Kirill, it was much worse: it was boring.

“You spend years working on database query tools, only to say ‘I’m sick of it, I quit’ and join a database query tools company,” Kirill said. “Where’s the imagination?” Forget the banality of evil, what galled Kirill was the evil of banality.

To someone at Google, perhaps the choice doesn’t seem banal because the two companies seem different: Google has its own dance studio, whereas Facebook only washes employee’s clothes. Google wants to become a dominant social network, and Facebook already is a dominant social network.  But to someone at a true startup, the two kind of look the same. Both will succeed without you.

Of course, Facebook is one of the few truly great Internet companies, and it’s easy to understand why anyone would want to work there. But if you’re going to leave the security of the world’s greatest software company, why not leave to try something hard, something raw, something completely different? A successful run at Google is the Silicon Valley equivalent of diplomatic immunity in Lethal Weapon 2:  every venture capitalist wants to give you money and any startup wants to hire you.

You could help someone who actually needs it, you could do something that hasn’t been done before. If you fail, you won’t be poor, and you won’t be unemployed long. I’ve heard Facebook is hiring.

(Update: some folks at Facebook have taken me to task for the tongue-in-cheek headline calling out their creativity. I’m sorry. I hadn’t meant that seriously. The people moving between Google and Facebook are obviously the gods of Silicon Valley, people who belong on bubble-gum trading cards. And just judging by its product you can tell that Facebook is a stunningly creative company.

I really, really love Facebook, and love Google, too. I just always hope that the best engineers at both places, when it’s their time to leave, do so to work at a tiny startup or to start their own company. Deciding otherwise is understandable of course: the pay at a newer company is speculative, the hours are maybe worse than Facebook’s, but it’s a different kind of fun, feeling like the whole place would keel over if you didn’t do your part.)

The Crazy Woman Speaks

On a Sunday transcontinental flight , I was stuck in a middle seat next to a woman reading a book filled with crazy conspiracy theories.

I minded my own business, thinking of a friend at Berkeley who once saw members of a cult walking down the street toward his house. Though heterosexual, he took off all his clothes, clasped the hand of his roommate and, when the missionaries knocked, invited them in for a religious debate. I imagined the argument I would have with my seat-mate in a situation like that, sipping tea naked on a couch, atomizing her world view.

While I was busy with that, the woman opened her laptop to view some paintings of flowers. Almost involuntarily, I mumbled something about how pretty they were. She mentioned that these powerful, emotional works had been painted by people with autism and dementia. She had dedicated her life, she said, to helping them paint.

Tears didn’t actually come to my eyes until a few minutes later, when I saw the pictures of the artists next to their paintings, smiling for what seemed like the first time in a long time, oblivious of the bleak institutional setting in the background. What prompted my seat-mate to help folks whom almost everyone else had given up on?

It was another reminder that people whom I disagree with are good people, and that they are as likely to be right as I am. This has been the essential humbling experience of life in my 30s, especially of my life running a startup. You see how many surprising shapes and sizes good people come in, and occasionally get zinged with how fallible you are.

Whereas my imaginary argument with my seat-mate had made me feel smug but still bad, my actual experience of her made me feel good. It’s an experience I’m lucky to have had, not just on the plane, but over and over again at work.

The reason most people have fixed opinions is that they get tired of never seeing them enacted, but I get to see my ideas in action every month at Redfin. We try out beloved website features & make hiring decisions, and discover they sometimes don’t work out. The rubber meets the road. The crazy woman speaks.

In this way, a startup turns you into both the lab rat struggling desperately to survive and the lab scientist standing back and measuring his performance. It gives you less patience with the ideologues telling you what the rat should have done.

If more people could see that the measurable, indisputable outcome of getting your way was sometimes disconcertingly bad — if reality could surprise you more with how often people you wrote off turn out to be your savior — we might stop listening to the smug partisans on talk radio, the outlandish political candidates in both parties, the outraged voices in our own heads.

And, stuck in the middle, we might get more out of our crowded, lonely flight across America.