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It’s fashionable these days to talk about a startup as a rollercoaster, with ups and downs, flips and flame-outs,  twists and turns. There’s some truth to that, and even more drama and glamor.

But roller coaster rides last five minutes, not five years. And as any venture capitalist will tell you, the average holding period for a successful early-stage investment is now approaching seven years.

It’s a new problem. Whereas the 90’s generation of startups either went public before the bubble burst or died trying, this generation is now entering an awkward adolescence: generating revenues, growing fast, still privately held.Allie Howard

Many entrepreneurs didn’t expect to still be at it: in the many, many lists of heroic traits an entrepreneur is supposed to have, no one includes endurance. Yet in my experience, the most common reason startups end is not because they run out of cash but because the entrepreneur runs out of gas.

Even so, some dispute that endurance is desirable, let alone important. When an entrepreneur leaves her own company, we’re supposed to nod sagely and say that this is the natural way of things, that she is better suited to starting companies than building them.

This may be true of entrepreneurs at many companies but not at the greatest ones: Microsoft for 32 years under Bill Gates, Apple for 35 off-and-on years under Steve Jobs, Oracle for 34 years under Larry Ellison, Amazon for 17 years under Jeff Bezos, Google for 15 years with Larry Page and Sergey Brin, now Facebook for 7 years under Mark Zuckerberg.

We rightfully celebrate these entrepreneurs as geniuses but I feel sure that what they value most about themselves by now is their endurance. Compared to the many talents with which they were born, endurance is the only trait these entrepreneurs have had to earn. “I can’t go on like this,” they tell themselves each year. “I’ll go on.”

In the age of the long startup, this endurance has become even more important, especially for entrepreneurs less talented than Larry Page or Bill Gates. The only plaque I have from my years at the company I co-founded, Plumtree, isn’t our IPO tombstone — I threw it out in my last move — but a cheesy piece of lucite we gave everyone on her fifth-year anniversary.Bryan Selner

The five-year award is a tradition we’re starting this week at Redfin, in recognition of our first five-year veterans, Allie Howard and Bryan Selner. Allie and Bryan are, as Redfin’s Fernando Ferrufino likes to say, the Original Gangstas who made Redfin into their own thing, which has in turn become our thing.

Without Allie, Redfin would be much, much less fierce, in its advocacy for its clients, in its intolerance for mediocrity, in its bad-ass attitude generally. Without Bryan, Redfin would be less exacting, less thorough, less thoughtful, less pragmatic, less team-oriented, less goofy and nerdy.

But what have Allie and Bryan gotten out of Redfin? It’s a serious thing to walk into a startup on a lark and come out years older; and in an age of secondary stock sales and recruiting revolving doors, it’s more unusual too.

The simple answer to this question is, I think, love. Love is a strong word, but I find myself using it more often as the days pile up at Redfin, to describe the brilliant people around here who have stuck together through ups and downs. It gives a thickness to our life at work.

The other reason Allie and Bryan are here is because they believe in what we’re doing. What people fear most in their careers is the absence of any arc or substance, which leaves us to float in the air like that mesmerizing piece of garbage in American Beauty – moved by forces we don’t understand, hardly able to keep going.

Compare that heart-breaking aimlessness to the intensity of Mark Zuckerberg in The Social Network. I just loved watching him alone, plugged into his laptop, listening on headphones to the film’s minor-key soundtrack. You feel an almost pelagic sense of peacefulness and then that midnight blooming of creativity which give sudden weight to our lives; it’s one thing the whole sordid soap opera really got right about startups.

And it’s a good place for Mark to be, right there, thinking. There have been many, many nights where Redfin has been, for me, the same kind of good long groove: the place where I belong, the work I should be doing, the thing I believe in.

And it can be hard to get your groove back, or to find a new groove. When I read about a Google rapid-response team running around with billions in money and stock to throw at anyone who threatens to leave, I think the real problem there must be meaning, not money. If you have to pay someone $50 million to stay at a job, it’s time to start over with a new team, and probably a new mission too. This is exactly what Larry Page is now trying to do.

But if you’ve still got something to believe in and live for — a work project that will be a multi-billion-dollar force for good in the world or, more personally, a life that sits at the center of a family — the only problem is leaving not staying. Gabriel Garcia Marquez wrote about this on the final page of Love in the Time of Cholera, which I still remember, 20 years on, as if I just read it:

The Captain looked at Fermina Diaz and saw on her eyelashes the first glimmer of wintry frost. Then he looked at Florentino Aziza, his invincible power, his intrepid love,  and he was overwhelmed by the belated suspicion that it is life, more than death, that has no limits.

“And how long do you think we can keep up this goddamn coming and going?” he asked.

Florentino Aziza had kept his answer ready for fifty-three years, seven months, and eleven days and nights.

“Forever,” he said.

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Chief Executive Officer

Glenn is the CEO of Redfin. Prior to joining Redfin, he was a co-founder of Plumtree Software, a Sequoia-backed, publicly traded company that created the enterprise portal software market. Glenn was raised in Seattle and graduated from the University of California, Berkeley. Redfin is a full-service real estate brokerage that uses modern technology to make clients smarter and faster. For more information about working with a Redfin real estate agent to buy or sell a home, visit our Why Redfin page.

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