Starting out as an entrepreneur, I once tried to hire an engineer who was so engrossed in the brain-teasers we had given him that he never noticed my nose had begun gushing blood in the middle of our interview (I had actually walked into a wall while gesturing wildly to my partner and mouthing “Let’s hire this freaking guy!!!”).

But since then, I’ve come to learn that there is something far, far worse than people who aren’t Math Olympians. There are people who don’t do the right thing, or care about others. No matter how hard somebody works, if his values are messed up, he’s useless to us. In fact, worse than useless: he screws up the whole company’s reputation.

So Redfin is taking a more balanced approach to the talent-at-any-cost mentality that drives most startups, by emphasizing values too. Starting today, Terrell Owens couldn’t get a job here. This isn’t an easy change for me; I still spend four days every fall rifling through the Stanford computer science resume book looking for the 25 highest GPAs so I can beg them to work for us (Rebecca Illowsky, you made the wrong choice!). But what I like about values-based hiring is this: anyone can have the right values. It’s just that many don’t.

The choice is yours.

Lots of people work for just a paycheck, doing only what is expected of them, with none of the gumption to understand what’s really going on and to make things better. They view any form of idealism with suspicion or embarrassment, and they try so hard to be official and corporate that they can’t have a good time. Many call themselves professionals, but never profess to put their clients’ — or anyone’s — interests ahead of their own.

We want to avoid hiring those people. Which will be tricky, as Redfin has begun to grow very quickly, hiring agents in every market we serve.

So a few weeks ago, Redfin pulled together folks from across the company — agents, field agents, engineers, executives, product managers, even customers — to talk about what we valued in one another. And then we talked about how we’d act if that’s what we really valued. Here’s what we came up with:

Julie Brown and Ann Rhoades, who built the customer-service organizations at Southwest and JetBlue, flew out from New Mexico to help us get through our spats and funks.

The fur really flew. We put in stuff like caring and balanced that would never have occurred to an Ahab like me, even though I could have cried hearing colleagues say how far from those values we had sometimes strayed. We stuck with idealistic terms like mission-driven despite some concerns that it was kind of a wussy value for a company that needs to turn a profit (giving people something to believe in is the only sustainable way to turn a profit).

We ditched scrappy at the last second because it reminded people of either a cartoon dog or a drunken runt who starts a fight.

And we tried to avoid the usual corporate baloney, though anything that just hangs on the wall sooner or later starts to smell that way. The only way to keep it fresh is to call out the values every day, guiding how we hire, pay and promote folks within Redfin, how we build our website and serve our customers.

Hopefully, you’ll keep us honest. If a website feature isn’t beautiful, if it isn’t does make you smile, if we aren’t completely transparent with data, call us on it. If we don’t put the customer first, and rally to get the job all the way done, scream it from the rooftops (or maybe just send us an email). The reason we published our values is so we can be accountable for upholding them. That, and to hear what you think of ‘em too… have at it!

Thanks to all the customers and employees who helped us work this out. And thanks to Janelle Saylor for suggesting this Liberace photo to personify our headline values of Wow and Fire (or was it Genuine)?

1. “Once you have a deal under your belt — whether it’s a $3M deal, a $30M deal, or a $300M deal, you are bankable.  People will bet on you again.” Ideas, not capital, are scarce. Selling a good company so that one you haven’t even thought of yet will be bankable — that is madness. Aaron Patzer — and anyone else in his position — was bankable well before he sold his company.

2. “And for the young entrepreneur — particularly those under 30 who’ve never done it before — the single best thing you can do to ensure your future success is TO GET A DEAL DONE.” Saying it is especially good for young entrepreneurs to sell their company is especially wrong. Entrepreneurs “who’ve never done it before” don’t need a farm system, or training wheels, or a practice run. Almost every great company (Amazon, Apple, Dell, Ebay, Google, Microsoft, Oracle, Yahoo!, PayPal, Facebook) was started by someone 30 or under. Your best idea usually comes before you’re 30.  Your ability to take risks is highest before you’re 30. In my experience, second-timers have a higher success rate because they are pragmatic and savvy about building a company for an exit, but the magnitude of success is highest among first-timers. If first-timers don’t create public companies, nobody will.

3. “Playing well sometimes means you take a single or a double instead of getting thrown out trying to steal home.” This talk of “swinging for the fences” and “striking out” or “getting thrown out at home” seems like a scare tactic. The difference between software and baseball is that you can swing for the fences and miss, and then just go back to second base. With the exception of Pointcast in 1997, which startup has gotten to the point where a lucrative acquisition is possible, decided to try building the business further, only to discover that there is no longer an exit at all? The company I co-founded, Plumtree Software, turned down seven acquisition offers before going public and accepting our eighth offer. What once made it hard for young people to hold out was their need for cash, but now most successful companies give the founders an opportunity to sell part of their stake early.

4. “Why is it that no one seems to think switching jobs every 3-5 years is a bad thing, but somehow think that selling your business to someone who really wants it and will grow it isn’t terrific?” Selling your business and switching jobs are totally different; anyone who has started a company knows that; you know that.  The idea that every entrepreneur is a serial entrepreneur, who can think of a new startup as easily as getting a gallon of milk from the store or finding a job at Kinkos, is a fiction we use to persuade ourselves that we’ll easily get another shot at greatness. It isn’t that simple. Ask Max Levchin, who seems to have gone through a Great Night of the Soul before founding a maker of Facebook applications, Slide. Just ask Aaron Patzer in five years. I don’t know Aaron and certainly wouldn’t want to bet against him, but if he makes as much money or has as much fun building his next startup as he did this one, he will have beaten some major odds. If I had been his adviser, I’d have helped him do whatever he wants — just as you did — but I also would have told him to keep having fun if he still believed in Mint. I think entrepreneurs need to hear that, too (for the record, I love Redfin as much as Plumtree, and Redfin may get bigger than Plumtree too, but this was a lucky break).

5. “More transactions of any kind or size help improve overall startup ecosystem health.” It is an interesting argument that small-scale transactions create liquidity and transparency, but surely public companies do that best. More to the point, Google, Microsoft and Amazon can’t buy every startup, particularly since many of their recent acquisitions haven’t been accretive. Without new venture-backed companies maturing into public companies, the total amount of capital available to fund innovation will decrease.

And the rest I agree with. It is outrageous baloney that anyone pressured Aaron Patzer to sell Mint. And there are plenty of startups that should sell when they can, for reasons both rational and admirable. But telling young entrepreneurs that they’re not ready to be a Jedi yet, just because they’re young — that just isn’t the Dave I know and love…

Update: a comment notes that the original Jason Fried essay never said that Aaron Patzer was pressured or forced into selling Mint. Jason just said that there’s an environment that made it easier for Aaron Patzer to sell, a point to which I am at least sympathetic. Jason, I just read your essay more carefully, and see that this comment is correct.  If you read what we’ve written earlier on the topic, you’ll see that we agree even more than I had originally realized.

For any aspiring entrepreneur, Urban Spoon’s advice is a lot more actionable and realistic than the recently celebrated keynote at the Seattle 2.0 awards. Glen Kelman’s talk should come with a warning label: if you are listening to an entrepreneur give advice for 20 minutes and he’s talked about raising money and valuations but never mentioned making a profit, look out! In his talk, Glen assumes “sooner or later you are going to have to raise money” because, unlike Urban Spoon, he’s not thinking about living off the money his product makes or holding his spending as low as it can go the way Urban Spoon did.

I agree that Urbanspoon’s advice is more actionable and realistic; I wasn’t trying in the keynote to tell people what to do so much as express how we’ve all felt from time to time. Folks in the audience like Jonathan Sposato and Kelly Smith don’t want to hear from me how to run their businesses, especially not at an awards dinner.

The truth is that neither Adam nor I wrote or spoke much explicitly about how to turn a profit. But I did try to talk about profits from the start, saying that all our anxieties as entrepreneurs turn on whether we can make money. Later, I  encouraged entrepreneurs to build a product good enough that customers would pay for it and to focus on a meaningful problem as a means to profits rather than the other way around. Both Adam and I described working 18 hours a day in a crumby office for no or low pay as being the essential characteristic of life at a startup.

Adding on to Josh’s critique, Brad Hefta-Gaub wrote that he agreed with Josh that too much attention has been paid to my (see comment from Brad) a “go big or go home” approach.

Here’s where I want to set the record straight. I have nothing but the highest respect for boot-strapped startups. They’ve done what Redfin tried but failed to do, which is get to profits without spending other people’s money. 

So why do folks think I feel otherwise? I can only assume that this beef began with a blog post I wrote last September, called Honey, I Shrunk the Startups. That essay took issue with two venture capitalists, Fred Wilson and Rob Monster, for arguing that the same big ideas we funded ten years ago for millions could now be launched for $100,000 or even $25,000, because of lower hardware costs and reusable software components.

I just didn’t see how $500-million venture funds can generate meaningful returns from 30 or 40 companies with $5 million exits, a problem which Fred himself has recently written extensively about. And I still worry that some big ideas — which will always take talent and time — have been cut down to size for lack of funds.

But the venture capital industry’s problems aren’t Urbanspoon’s problems. What I said about VCs’ need to get a big return on a few of their deals doesn’t apply to Urbanspoon.

And my preference for big ideas isn’t the same as a preference for big companies. Picnik, in my view is a big idea; can you imagine how hard it is to build Photoshop on the Web? Urbanspoon is a big idea, competing against entrenched competitors like Yelp and CitySearch. Both companies are small.

Given a choice, we would all prefer a startup with a big idea rather than a small idea. We would also all prefer one that spends less rather than more money to develop that idea. But a big idea that can be built for very little money isn’t always easy to come by.

So some of us pick  narrowly focused startups we can build on a dime, while others focus on big ideas that also take a lot of money. My argument has always been that there should be room for both, not just the small idea. As I said in the original post:

Trading college-girl gossip or graphing rock-band popularity is cool but we also need entrepreneurs willing to spend the time and money to f*** with the order of things.

And again a paragraph down:

Of course, some businesses don’t need a lot of money to get big. Others are happy to remain small. But there are big ideas that take time and money…

And a third time at the end:

The (TechCrunch50)  judges may argue over which contestant is the most clever or polished, but for those of you scoring at home, there’s room on the card for another column. Which startup is most likely to f*** with the order of things? We need a few of those too.

So I am not arguing that all startups should be big, or that big startups are better, only that we need startups with ideas large and small. The same Procrustean bed that stretched every startup in the ’90’s to be bigger is now scrunching some ambitious startups down. Big isn’t always better. But smaller isn’t always better either. VC-backed deals are best for some companies; boot-strapped companies are best for others. Arguing for one or the other is just silly.

The only startup I am arguing against is the venture-funded company built to self-destruct in 18 months, which never seeks to generate a profit because its only hope is to get bought before it has to. As I said in the original essay, these days, “most entrepreneurs don’t even aspire to build a self-sustaining business.” Given this emphasis, I’m not sure why Josh says I’m “not thinking about living off the money [my] product makes or holding [my] spending as low as it can go.”

Redfin is not a venture-bloated bully looking down its nose at other little startups. We aren’t looking down our nose at anybody. We’re fighting to get profitable and serve our customers well. We look at all the great startups in Seattle and we try to learn from everyone. Already this morning here at Redfin, we were all abuzz about what we could learn from Adam’s essay.

Of all the venture-funded companies to characterize as a goliath, Redfin must be the last choice. We started as a bootstrapped company with the first map-based real estate search and no money when we suddenly found ourselves staring down the barrel of two new map-based search companies run by terrifyingly brilliant people that would ultimately raise $120 million from Accel, Benchmark, Sequoia and a handful of hedge funds.

We’ve raised a sixth of that, even though our model is less capital-efficient: only Redfin has to hire actual customer service personnel in every city we serve. Maybe others think it was dumb for us to have chosen this, or just plain too expensive, but it was the only way we thought we could really change the game.

Who knows whether Redfin will succeed. I think everyone would agree though that there’s a need to make big bets and small bets, and that Seattle will be better off when a decade from now one of today’s startups becomes a company like Microsoft, Real or Amazon, one that can buy other startup companies too. That’s still worth shooting for.

Many thanks to all the folks who showered kind words on the keynote. And thanks to Josh Petersen for giving us a reason to set the record straight.

When I first got involved in raising money for my last employer, Plumtree, I looked at a venture capitalist the way Wiley E. Coyote looked at the Roadrunner, as a mirage of drumsticks and chicken wings, garnished with a sprig of parsley. Assessing an investor for his advisory ability seemed like asking about a heart surgeon’s personality before getting a triple bypass; it was hard to think beyond the cash we needed for our survival.

Ten years later, raising money for Redfin has often still been a gambit — our last effort was in 2007, and it wasn’t as easy as we thought it would be — but what made it easier was that we had convinced ourselves we really were evaluating each investor too.

Of course, it isn’t always possible to choose your investors. Beggars can’t be choosers, and all of us unprofitable companies are beggars. But my point is that approaching money-raising as a choice actually makes you a better beggar. Nobody likes being sold to, but everybody likes being chosen.

I still read tweets and blogs about how to make a VC moan with pleasure or lose his mind or do whatever he is supposed to do, but a VC relationship is more of a marriage than a one-night stand. Yes, you need a mission statement that fits on the back of a business card, a snapshot of your financials and the blue-bottle magic of an insanely great demo — which I have to admit should have the intensity, the lack of antecedent, the awkardness and brevity of teenage sex.

But after that it seems obvious that you just want to have a conversation about the business. PowerPoint, an evil system of command and control that turns one person into an unstoppable bore and the rest of us into zombies, is responsible for billions of dollars in lost valuations.

And if you aren’t asking as many questions as the investors are, you can fall into becoming a performing monkey, skimpering down Sand Hill Road from one meeting to the next with the same song and dance. Ideally, raising money is more like traveling to alien planets in a densely clustered solar system, where you encounter very smart creatures who have no idea what your world is like, but ask you questions that make you wish it were better.

It has been so long since Redfin has raised money that I worry we’ve lost touch with an important source of ideas and information. I still remember the questions from last time: why doesn’t Redfin charge users for premium access? Have you looked at how Yelp encourages users to compliment one another’s reviews? Why aren’t you offering mortgages? I try to answer every question with “yes,” “no,” a number, or “I don’t know.” For the best questions, the answer is usually “I don’t know.”

But you also need to have questions of your own. Here are some of my faves:

1. How do you see our market changing over the next few years? Your investor has to develop her own ideas about your business sooner or later. At this early stage, this question is mostly an IQ test.
2. When times have gotten tough for your portfolio companies, how have you helped them out? Anybody can get lucky with an investment that takes off like a rocket; all you have to do is hang on for dear life. A VC’s true measure is how she gets all her other companies pointed in the right direction.
3. Who are your favorite entrepreneurs? Some people genuinely like entrepreneurs, notwithstanding their volatility and constant intellectual jousting. Most people fake it. If the investors’ fave five is composed of people she hasn’t worked with, she’s faking it.

It’s a fun process. Yes, when really smart people get to know everything about you in a very workmanlike way and then pass by the dozen, it becomes a self-esteem destruction machine. But mostly, it’s fun. Every entrepreneur I know secretly loves the WSoP-stakes game of raising money: the marbled lobbies and green courtyards, the bountiful assistants bearing glasses of ice-water are so much nicer than our grubby little offices.

What I don’t understand is why entrepreneurs only love venture capitalists until they give us money. As someone who always hated rich people and people in authority, I remember as a younger co-founder being shocked at how the grown-ups at Plumtree spoke respectfully of our board. I kept waiting for them to take off the rubber masks of their own faces and say, “just kidding, we hate them too.” So maybe now you’re waiting for me take off my rubber mask.

But back then, I just wanted to build good software and market it straight down the world’s throat. Now that I feel responsibility for other parts of the business, I need more help. This fall, despondent about our layoff, I really needed help.

Sooner or later, you will too. You’ll feel all alone in whatever you’re trying to do, and you’ll need advice. If you’re really in a jam, you won’t even be able to ask normal people for advice, because the situation is so bad you don’t want anyone to know about it. Your friends will listen to your better-than-it-really-is situation assessment while browsing the web or yelling at their kids, and then tell you what you want to hear: that the situation is better than it really is, that your board is wrong and you are right. If you already know what to do and just haven’t done it yet, this feels great. If not, it makes you feel more alone.

This is why it’s a good idea to at least try to choose your VCs, instead of just begging to be chosen by them. I almost didn’t write anything about recruiting and choosing VCs because I am so bad at talking to them — at a climactic meeting with an entire firm a few years ago, I opened the presentation by asking if the firm had ever made any Seattle investments, whereupon a senior partner gently reminded me that he was the first venture capitalist to invest in Microsoft — but the one real lesson I’ve been able to glean from the whole experience is that being a better chooser makes you a better beggar.

(photo credit: D.James | Darren J. Ryan)

Which made me wonder how private we really are. You can hide from the Wall Street Journal but not from the hundreds of tech and real estate blogs that covered Redfin last week. One big difference between Web 1.0 and Web 2.0 is that this time, the meltdown will be blogged.

That kind of attention can lead startups to dither like publicly traded companies before making hard decisions. And it has prompted some startups to turn against blogs just for covering the news.

Connections with Other Little Companies, Everywhere
But Redfin has no complaints. Blogs brought us our first customers and our best ideas. Most important for the lonely types who tend to go off on their own to make software, blogs connected us to other little companies everywhere.

Sure, eWeek or CNET covered startups before, but it was blogs like TechCrunch and GigaOM – with their fits of idealism and jadedness, of accessibility and remoteness, of cleverness and heart, their sense of “we” and “they” — that first made us feel cool.

When Redfin announced our layoffs, we expected all that to turn against us. But there was only empathy for the company and, most important, for the people who had to leave the company.

To all the folks who blogged or commented on our setback, thanks for your even-handedness. Redfinners past and present have never needed your support more, or expected it less.

The End of Cool
The only thing that we lost in having blogs write about our troubles is our cool: the cool of startups that never struggle, that show up on all the “hot” lists, that always seem to be having a ball, that don’t have a care in the world.

That’s ok. Startups haven’t always tried to be cool. Today, the blogosphere has created its own celebrities, mixing Michael Arrington with Ashton Kutcher, MySpace with Paris Hilton.

But my first startup job was about as far from cool as you could get, a reunion of all the people at the desolate end of the high-school cafeteria. We rented U-Hauls to drive our own pop-up booth to a trade-show. At big client meetings, we wore debate-tournament-era suits.

Even starting a company that went public was never really cool in the way it’s usually portrayed: it meant walking through rivers of my friends’ blood, and working on silly little things all night, and caring too much, and becoming a jerk and becoming humble again, and it meant joy that arrives without your noticing it, and love and above all things — not a flash of brilliance or a dramatic strategic decision — endurance.

And that is the one trait that characterizes Redfin, endurance. This was a business run out of an apartment, by people working for free. We created a real service when it was fashionable to be all virtual. We have changed the game rather than play the game. And now we offer a service so valuable to so many people – and so much better than what they have come to expect — that I believe we will always endure.

The Only True Currency
It seems like the blogs — which are typically written by compulsive people late at night in their bedrooms, for reasons they can barely explain — are best equipped to understand what we are going through: setbacks and endurance, passion and hardship, being cool and not being cool, working for love and scrapping for money.

As Lester Bangs explains in “Almost Famous,” the “only true currency in this bankrupt world is what you share with someone else when you’re uncool.” This impulse is what drives blogs and startups alike. That bloggers have reached out to us now, when we have never felt less cool, is the truest currency there could be between us.

(Photocredit: Philipp Klinger on Flickr)

Unlike other startups, our industry’s recession started a year ago, when home prices first plunged.

Since then, we’ve fought like starving animals, and with some success: while industry-wide transaction volumes dropped 33%, we grew revenues by nearly 50%. Traffic grew more than 300%.

Even a month ago, we were raising 2009 revenue projections. All our markets, now including Chicago, contributed profits.

But the past few weeks have seen a major reversal. As the stock market wiped out prospective down-payments, tours and offers dropped 30%. Transactions that were done came undone. October will still be pretty good, then we’re headed for a big dip.

Hence the layoff. Layoffs are painful for any company, but especially for a startup and especially, I think, for Redfin.

The Layoff & Redfin’s Values
That’s because Redfin folks have always been believers. We earn our salaries from 9 to 5 but everyone leaving today gave a lot more than that.

The company has always had a sense of mission – to change the real estate game in consumers favor, yes, but also to be an open, humane place to work. It may seem now like we are a business that cares only about profits.

We aren’t. The whole company has been dedicated to the idea that money is how businesses work, but not why.

We want to make money, yes — and not just a little — and we absolutely have to avoid running out of it, but we haven’t given up on our larger ambitions: to build a new kind of company for employees and consumers alike.

To Those Leaving
Even under great financial pressure, we have treated departing colleagues as generously as we could: less than we would have liked, but as much as we could possibly afford.

To those who left, I can only say thank you for all that you’ve done for Redfin, and I’m sorry. It wasn’t your fault that you had to leave, and we will do what we can to help you take your next step. We’ll miss you, and we wish you the best of luck.

What Next for Redfin?
And now, we have to answer the question the rest of Redfin is asking: is this the beginning of the end? No, I don’t think so.

We are one of the few startups to offer:

1. an essential service
2. directly to paying clients
3. that yields multi-million dollar revenues.

A real business used to be unfashionable, but now it’s indispensable.

The Best Website
The sky may be falling in financial markets but our competitive dynamics haven’t changed. We can become the #1 real estate search site because our data is better than the media sites’ and we think our engineers are better than other brokers’. We’re willing to share more data with the consumer than either one of them.

An Essential Service
Our value proposition isn’t entertainment; it’s to make a fundamental service better and cheaper. We offer an alternative to traditional brokers that customers want, and not in some namby-pamby nice-to-have way. Our market, even if it shrinks to half its recent size, would be $30 billion per year.

A Large Market…
That means we have plenty of room to grow. But we won’t grow without taking big chunks of market-share, which also means we’ll have to keep tinkering with our offering so it appeals to the mass market. We’ve been planning a change to our service for months, which we’ll launch in November.

But We Have to Change
Change is painful, but necessary. Late in Charles Darwin’s life, when he was busy rejecting the application of his principles to social policy, he explained that “it is not the strongest of the species that survives, nor the most intelligent… it is the one that is the most adaptable to change.”

It’s tempting to write Redfin off now precisely because we are adapting to the market. At my last startup, we adapted quickly, laying people off early in the dot-com bust. Many wrote us off. But in 2002 we completed one of only two high-tech public offerings that year.

Redfin’s whole business will struggle and fight and may yet fail. But the only way it is possible for us to succeed – and, even today, I believe we will – is if we adapt.

He’s taking a long-planned one-year sabbatical with his fiancee to travel around the world, and just wrote an eyewitness account of life at Redfin based on his nearly two years here. We rarely realize how the world perceives us so I was very interested to read it, particularly since Shahaf has always been thoughtful, candid and constructive.

Shahaf describes Redfin as a place full of passionate, hard-working people, heralds our customer-focus, complains that our benefits package should include a health club membership, notes that we get into silly arguments with one another, and also wants us to do more long-term planning. He talks about learning more and advancing his career much faster than at a big company, but also says he could work at a big company again. It’s entirely BS-free, and has given me a lot to think about ways we could improve.

In the end, Shahaf acknowledges that there is a “non-zero chance that Redfin won’t be there by the time I return from the trip.” Shahaf refers to this risk as “excitement,” which made me smile. It’s true that our company has to perform to grow into a self-sustaining company,  but that’s a good discipline. Business lately has been good and, as Shahaf notes, we’re operating in a huge market, and our customers love us. In the end, he manages to sound sober and optimistic at the same time, a trick many startup leaders struggle to master.

In a second post, Shahaf talked about what he’ll miss in his year away from Redfin’s culture, praising Dan Fabulich’s “incredibly high signal-to-noise ratio;” Chelsea Mitchell’s exuberant piercing, joyful laugh; Jamie DeMichele’s launch-day lab coats; Kevin Broveleit’s harrowing, heroic (and successful!) efforts to lose 20 pounds in seven days.

A great poet once talked about traveling to the four quarters of the world and, returning to the place where he started, really knowing it for the first time. But in Shahaf’s case, he already understands us pretty well. Thanks Shahaf, and bon voyage!

Which came as news to our chief technology officer, our Seattle-based engineering leaders, three star product managers and our hyper-productive lone marketing director, all of whom worked at Microsoft.

And it came as news to me, since I grew up in Redmond, adore Microsoft’s pass-the-bong video ads, and defend to the death the relevance of desktop applications (see comment 107). The first business book I ever read was Microsoft Secrets. My new favorite marketing campaign is Microsoft’s “I’m A PC” campaign. 

So it’s probably fair to say that no CEO from Silicon Valley has a higher opinion of Microsoft than I do. I learn from Microsoft every day. And I’m intensely grateful that so many Microsoft and Amazon folks have thrown their hat into the Redfin ring.

“This Was Discussed at the Highest Levels Within Microsoft”
The trouble started because of one line in a Redfin job description: You don’t need big money to do something big. Don’t apply if you’ve worked too long at Microsoft, Amazon or an agency.

“This was discussed,” one applicant explained over a slice of pizza at a mall food court, “at the highest levels within Microsoft.”

What kind of “pompous ass,” one angry Microsoft veteran asked us, would write this job description? The people at Microsoft and Amazon, he continued, “know exactly what it takes to run in a start up environment, we were doing it when whoever wrote this ridiculous JD [job description] was probably in diapers.”

Of course, I’m the pompous ass. We agree that 30 years ago, Microsoft could still fairly be called a startup, though by that time I had graduated to underwear.

We probably disagree over whether someone who has not worked in a startup for 30 years is still a startup-type of person. And we disagree too, over whether any disrespect was intended to Microsoft, a company more successful than we’ll likely ever be.

Different Horses for Different Courses
My point wasn’t that any 15-year veteran at Microsoft has less talent or skill than the driven maniacs who tend to thrive at Redfin. Microsoft is a gladiator academy for brainiacs. But no one can honestly tell me that marketing Windows is remotely similar to persuading someone to ditch her Realtor-friend and buy a house through a website. We have no no budget, no agencies, three people.

We have to win by delighting consumers, juicing the Google index, having Octopus sex with the blogosphere, fighting like a trapped squirrel, moving super-fast. There’s just no way a company the size of Microsoft or Amazon — or Google (after complaining that we never saw Google candidates, we have seen a few) or Apple — could remain as desperate and impatient and unrealistic as we are.

Plenty of Microsoft folks thrive at Redfin and other startups, but their point of departure is how different a startup is from Microsoft.

“How Long is Too Long?”
Our best employees left Microsoft because they were squirrels and octopuses, juicers and speed-freaks. Some had been there two years. Some five. Some longer. But none had been there “too long” which was supposed to mean past the point of being passionate about what they do.

When we wrote this job description, we’d interviewed plenty of Microsofties who talk about staying “too long.” They’d say Redfin is a way to rekindle their passion for software or business. It makes us feel like a red sports car, or an extramarital affair.

Of Microsoft, But Unlike Microsoft
The truth is that many of the people at Redfin are of Microsoft, but they all say Redfin’s not like Microsoft. Marcelo Calbucci explained the difference.

The way I think about it is that our left brain (analysis, discipline, brilliance) comes from Microsoft, and our right brain (speed-lust, techno-promiscuity, the Internet’s goofiness and freedom as a cult) comes from Silicon Valley; nearly half of Redfin engineering is based in San Francisco.

It’s a good balance. What we’ve learned from Microsoft employees has made us better in engineering, product management & HR, where Microsoft folks excel. In marketing, Microsoft has taught us how to think in different dimensions than just public relations, social networks or search engine optimization.

What Do You Think?
We thought we’d ask other startups what your experience has been hiring from Microsoft and Amazon? And we’d like to know what to do about the job description. If it has offended others, we’ll change it. If there are any folks from Microsoft or Amazon reading this blog, please, tell us what you think (and if you haven’t worked there “too long,” apply for a job!)

(Photocredit: sexy octopus, jrixunderwater; speed dog, WisDoc )