The Next Big Thing You Missed: Why the Most Ambitious of Tech Startups Should Fail Slowly

Venture capitalists advise startups to "fail fast," but that's 180 degrees wrong, says Pinboard founder Maciej Ceglowski, who urges entrepreneurs to "fail fast."
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In Silicon Valley, the conventional wisdom is that startups should “fail fast.” New companies should build their product as quickly as possible and if it isn't immediately successful, the thinking goes, they should just as quickly give up on the idea and "pivot" to a new one.

But Maciej Ceglowski doesn't buy the conventional wisdom. "I'd compare people who follow the 'fail fast' ethos to fishermen who throw their hook in the water once and leave if they don't get a bite immediately," he tells WIRED. Success is so often a matter of opinion, and even if we can all agree on what's successful and what isn't, we can't always achieve it in the short term. Those who fail fast may be throwing away some of the tech world's best ideas, and that's why Ceglowski believes that the most ambitious of startups should "fail slowly."

Ceglowski, the founder of a startup called Pinboard, wants to revive the notion that there's value in persistence, that you should stick to your own unique path no matter what the naysayers say -- investors, users, and Silicon Valley pundits very much included. "I’ve always been a proponent of failing really, really slowly," Ceglowski said during a talk this fall at the XOXO conference in Portland, Oregon. "Success doesn’t come labeled in any way to distinguish it from failure."

This is true not only in the fast-paced world of tech startups, but in all walks of life. Ceglowski's fail-slowly crusade began when the former freelance and Yahoo developer was studying Henry David Thoreau. The 19th century ecologist and nature writer didn't sell many books during his lifetime, but he's now considered one the finest of American writers.

Yes, Ceglowski says, there's at least one situation where success is rather easy to define. If you're only interested in making money, all you have to do is look at your latest income statements. But outside of the banking world, quick financial success is rare. Even the most cash-hungry Silicon Valley capitalist knows that profits can take years to surface in the technology game. That’s why venture finance exists in the first place. But the bigger point here is that money shouldn't be your only goal.

Ceglowski's push for slower failures is part of a broader public fight the Pinboard founder is waging against the Silicon Valley status quo. Pinboard, a company that helps you bookmark stuff on the web, is the embodiment of his iconoclastic approach. It’s a tiny company started in 2009 by its sole employee, not a juggernaut powered by a large team and supported by big investors. It charges users instead of giving away web services for free. And its ambitions are modest. The aim is to support Ceglowski, who made $181,000 last year off the company.

He may sound like a unique case. But nowadays, computing power and software is so readily available over the internet, anyone can follow his lead. Failing slowly is that much more possible if you can build something from open source software and hoist it onto Amazon's cloud computing service. You can launch a company with your own two hands -- and some pocket change for web infrastructure.

Being your own boss -- with your own income stream from paying users -- means there are no venture capitalists clamoring for quick success that can pave the way for an IPO. Ceglowski likens this sort of independence to Thoreau’s two years working as a bean farmer and living in a small house he built on a 14-acre lot in Concord, Massachusetts. Yes, you may fail. But you should give your idea every chance of succeeding.

Earlier this year, Ceglowski launched the Pinboard Co-Prosperity Cloud, a "fund" that allocated $37 to six winners, including a home-gardening site, a marketplace for home-baked goods, and a forecasting tool for sailors. The idea was that advice, endorsement, and publicity are all you really need to launch a web business if you’re careful with your money -- and spend it slowly.

Ceglowski may be the world’s cheapest venture capitalist, but his parsimony feeds what he considers a vital message for today’s young crop of tech entrepreneurs: Your life and ideas are far more valuable than the money you’re chasing.

"You only get a couple of chances to work on something for a really long time," Ceglowski said at XOXO. "You can pick what it is, but once you pick it, don’t abandon it lightly. Your life is not that long, and there’s no substitute for working on something and devoting a lot of time to it -- even if it doesn’t bring you success that you recognize."