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When Total Failure is the Key to Runaway Success: Insider Stories From Tech’s Biggest Names

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How YouTube, Twitter, and Groupon Really Got Started

You hear stories of successful billionaire tech entrepreneurs, but do you really know the inside story of how some of the tech industry’s biggest names got started? Believe it or not, some of the biggest success stories came from a very rocky (if not, downright failed) start. Read on to find out the dramatic pivots (and rebrands, thank goodness) of some of the sites you use everyday!

YouTube, formerly known as Tune In Hook Up

You read that name correctly. Before morphing into video sharing site YouTube, the founders worked on a video-dating site called Tune In Hook Up. Supposedly inspired by HotOrNot.com, the site did not get a lot of traction and soon fizzled.

The idea for the video sharing site we know today came from the founders frustration at not being able to find footage online of Janet Jackson’s infamous “wardrobe malfunction.” They quickly changed course and decided to make a general interest video uploading site, and voila! Only 2 years in, YouTube was acquired by Google for nearly $1.7 billion, and users today upload more than 35 hours of video to the site every minute!

Groupon, formerly known as The Point

Andrew Mason dropped out of the University of Chicago in 2006 to found a company called The Point, a social network designed to get groups of people together to solve problems. The site connected users in Chicago, but didn’t really grow beyond the second city. As the management team explored ways to sustain the company, a particular group using The Point piqued their interest: someone had formed a group to round up several people who wanted to buy the same thing to try to get a group discount.

When Lehman Brothers filed for bankruptcy and the economy crashed, Mason and the leadership team decided to do something bigger with this “group-buying” idea.

Mason decided to add some game mechanics to the deals, stuff like deals would only be available for one day, and each deal had to have some critical mass threshold before anyone would get the deal, and released it. Unless you have been under a rock for the past few years, you no doubt know the rest of this story. Mason soon abandoned The Point and turned his focus full time to Groupon. Within 2 years, the company had grown to 5,000 employees (it has more than twice that today) and peaked at a $1.2 billion valuation after it’s initial public offering!

Twitter, formerly know as Odeo (you know, the podcasting company!)

A small team in Silicon Valley was hard at work creating a podcasting platform. An engineer on the team had created a product that allowed you to call a phone number to leave a message, and it would turn your message into an MP3 hosted on the Internet. Useful, right?

The team turned the technology and interest behind that product into a company called Odeo, a platform to create, record and share podcasts. Soon after the Odeo product was created, sh*t hit the fan. Apple announced the launch of iTunes, and the founders of Odeo knew their business was DOA. Evan “Ev” Williams, the CEO of Odeo, directed his employees to start brainstorming new ideas for products. The company even hosted internal “hackathons” with the company broken up into groups. One team created a system where you could send a text to a number and it would be broadcasted out to all of your friends. The idea stuck, and Twttr (since evolved to “Twitter”) was born. 

 This piece was written by Leslie Zaikis and is reprinted by permission.

Image credit: CC by Don McCullough

About the author: Skillcrush

Skillcrush, your ‘how to get started guide to tech.’ You know that mastering technology is key to future success. Increase your tech know-how in collaborative online classes with real-live instructors there to help.

  • Bill

    Very inspiring and it will make any founder take a strong look at the value of a pivot if things are not taking off. Having the innovative spirit coupled with a great team seem to be of great value in the startup community.

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