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 )